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Rank #42 in Technology category


How I Built It

Updated 3 days ago

Rank #42 in Technology category

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A podcast about building things on the web

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A podcast about building things on the web

iTunes Ratings

83 Ratings
Average Ratings

Digging this podcast!

By rock phenom - Nov 10 2019
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Really well done show, with good solid advice, and Joe is a very helpful guy!

Great podcast for product builders

By RameshDon - Sep 18 2019
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Wish I had listened to this show earlier. Very actionable advice. Thanx

iTunes Ratings

83 Ratings
Average Ratings

Digging this podcast!

By rock phenom - Nov 10 2019
Read more
Really well done show, with good solid advice, and Joe is a very helpful guy!

Great podcast for product builders

By RameshDon - Sep 18 2019
Read more
Wish I had listened to this show earlier. Very actionable advice. Thanx
Cover image of How I Built It

How I Built It

Latest release on Jan 21, 2020

The Best Episodes Ranked Using User Listens

Updated by OwlTail 3 days ago

Rank #1: Episode 2: Rebecca Gill and DIY SEO Courses

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Rebecca and I talk about building an online course, the necessary dedication you need to be able to teach, and some great tools for setting up your own online course!

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The post Episode 2: Rebecca Gill and DIY SEO Courses appeared first on How I Built It.

Aug 30 2016



Rank #2: Episode 61: Morten Rand-Hendriksen & Teaching at Lynda

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Morten Rand-Hendriksen is an incredible developer and teacher who brings it all to his online courses. In this extra long Season 3 Finale, Morten and I run the gamut on topics, including courses, empathy, technology, WordPress, and more. I strongly recommend you give this one a good listen because it’s a great episode. Thanks so much for a great Season – see you in January!

Show Notes

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  • Liquid Web: Fast, Managed WordPress hosting whether your users are logged in or logged out. Get 50% off the first 2 months.

The post Episode 61: Morten Rand-Hendriksen & Teaching at Lynda appeared first on How I Built It.

Nov 28 2017



Rank #3: Mike McDerment and FreshBooks

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Mike McDerment is the founder of the incredibly popular accounting software FreshBooks. His story is an interesting one – where he started with an MVP and then built it up from there. His journey relatable, and I’m really excited to talk to him today.

Show Notes

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Intro: Hey, everybody. Welcome to Episode 110 of How I Built It. Today my guest is Mike McDermont of FreshBooks. I am so excited to talk to Mike because I have been using FreshBooks since 2008, or 2009. Something like that. Most of my adult freelance career outside of high school where I just used Excel. After a small journey away from FreshBooks to use QuickBooks online in 2018, like the prodigal son, I came back to FreshBooks missing what I once had. I am very excited to talk to Mike today about how he built up a company that I have been using for a third of my life, which is crazy. He offers of course fantastic advice on how he built the company, and how he is growing at a good pace with his customers now, trying not to grow too fast or anything like that. I just think that this is a fantastic conversation no matter what stage of business you’re at, because Mike has seen a lot of it at this point. I will get to the interview in a minute, but first of course we need to thank our sponsors.

Break: This season is brought to you by Plesk. Do you spend too much time doing server admin work, and not enough time building websites? Plesk helps you manage servers, websites, and customers in one dashboard. Helping you do those tasks up to 10 times faster than manually coding everything. As someone who just spent a bunch of time finding the right tools and automations to save myself time, I can tell you that Plesk is invaluable. You can try Plesk for free today at This episode is also brought to you by our friends at Castos. Castos is a podcast hosting platform built specifically for WordPress. They’re a Seriously Simple Podcasting plugin that lets you manage all of your episodes and podcast RSS feeds from your WordPress site, but have your files hosted on a dedicated media hosting platform. I love how the Castos team takes a common sense approach to their pricing, too. You can create as many episodes and podcasts as you want. You don’t have to worry about how much storage you’re using or silly bandwidth restrictions. If you’re like me and already have a ton of episodes from an old host, they’ve got you covered there, too. Castos will import all of your podcast content into their platform completely free of charge. It is just one click of a button. The Castos team has put together a special opportunity for listeners of this show. They’re giving away their most popular package, the YouTube republishing tier where they automatically convert your audio files into a video format and publish them to YouTube completely free, for one listener. For a chance to win tweet at me @jcasabona, and [@castoshq], and tell us why you think you should win this free year of Castos hosting. On February 1st, 2019 they’ll pick one winner to get this $340 package completely for free. Thanks so much to the Castos team for sponsoring today’s episode.

Joe Casabona: Hey, everybody. Welcome to another episode of How I Built It, the podcast that asks, “How did you build that?” Today my guest is Mike McDermont, founder and CEO of FreshBooks. Mike, how are you today?

Mike McDermont: I’m well. Thanks, Joe. Thanks for having me.

Joe: Thanks for coming on the show. I was saying in the preshow that I am a big fan of FreshBooks, I used you guys all the way back in like 2008 or 2009 or something like that. I’m excited to hear your story. Why don’t we start off with who you are and what you do?

Mike: I’m Mike McDermont, co-founder and CEO of FreshBooks. What we are is ridiculously easy to use invoicing and accounting software. 20 million people have used the software since we started, and what makes us different is we only build for folks who invoice their clients. We solve a whole bunch of billing problems in there, billing and accounting problems frankly. It’s available for desktop and cloud. If you invoice, you need FreshBooks.

Joe: Absolutely. I will say, I guess I’ll admit this to you on the air, but I used FreshBooks from like I said 2008 or something up until the beginning of this year, and I was like “I need something that can handle products,” because I’m moving mostly into the products business. So I moved to a competitor, and boy was that a mistake. I’m moving back to you guys at the beginning of next year and the next fiscal year. I’m just like, like you said, it’s ridiculously easy to use. Moving to your competitor I saw just how much easier FreshBooks is to use then what else is out there. So, I’ve seen the error of my ways and I’m moving back. I appreciate your software.

Mike: I am sorry for your trouble, but I am grateful for your support. We’ve actually done a lot in the last year that I think you’ll quite enjoy when you come back. So, we’re waiting for you. Thank you.

Joe: Awesome. I’m excited. This is fantastic. You have ridiculously easy invoicing software, and we were talking a little bit in the preshow so we’re going to talk about your accidental journey. Why is this called an “Accidental journey?”

Mike: The way we got started was I was running a small design agency helping small businesses build their websites and do internet marketing and logo design, all kinds of things. I was billing my clients using Word and Excel when I accidentally saved over an invoice, and I got super frustrated. I’d started building small web applications for my clients and figured maybe I should do that for myself. So, I built a simple thing and that became what is now FreshBooks.

Joe: Wow, that’s fantastic. We talk about this a lot on the show, for longtime listeners, I feel a lot of founders were solving a problem or scratching an itch that they had, and then it turns out that other people had this same problem. So you were using Word and Excel and you decided to build this for yourself, did you do any research into the feature set or what was out there? Can you give us a timeframe, we’re talking like 2006 or so, right?

Mike: Yeah, that’s that’s about right for time zones. A little over a decade ago. In terms of research, we took a very unassuming approach, so built the initial thing for myself, and then we did conduct structured research calling people up. You were in the basement, so I had surveys take people through “Why did you start looking for us? What would you call this thing?” Because we didn’t even know what to call it at that point, and then “If you had to describe it to someone else, how would you do that?” And then, “What else would you like?” That kind of thing. “What other pains can we help you solve?” Through a lot of customer service and through a lot of research we fleshed out what the product should be over time, and how to improve the offering we already had.

Joe: Gotcha. That’s great. So when you built this for yourself, were you immediately like, “This is something that I could charge for,” or what was the time between you built it, and started using it, and then you realized that this was a product that you could release?

Mike: About eight months after launch, about two years since we started it, we had like 10 paying customers. We started out, I think we had a business model applied to it, but I wouldn’t say we had things like pricing and packaging correct. The way we structured our packages basically meant a lot of people could use it for free. I don’t think that’s a bad thing. It worked out well. But we were basically trying to figure out, “What is the product? What features are necessary? Where do people see value and what do they want to pay for?” All those things were, we were groping our way through the darkness trying to figure out how to find a sustainable path forward.

Joe: Gotcha. Again, just talking about my personal relationship with FreshBooks, like I said I think I got on it around 2008-2009. More likely 2009, my friend told me about it and I think she had an affiliate link. Did you have like an affiliate program at that time, to help you grow?

Mike: Yeah. It’s interesting. We had a referral program where people get links inside their own accounts, yes. It worked a lot like an affiliate program where you can share a link with somebody and that would be– Effectively, short answer, yes.

Joe: Nice. So you mostly conducted interviews, customer service, you said after two years you had 10 paying customers. You have like, 10 million plus now. I’m just curious to learn what the jump was. You had 10 paying customers, what would you say is the moment everything clicked for you and you started to grow?

Mike: I get that question a lot. The simple answer is, I’m still looking for it. I think success is doing a million little things right when nobody’s looking, and then all of a sudden it turns into a thing. Maybe those are occasions where there’s this major turning point, but I’d say we just kept going. The biggest thing we did was we just kept going, we kept trying to improve, we kept trying to get to know our customer better and serve them better. Over time there’d be like, “We’ve got a new– We worked on our pricing and packaging,” or “We added a feature.” But it’s hard to really see major changes in the curve even when those events happened. It’s really about the direction and the continued progress, and trying to get better all the time. That was our story, at least. I’m sure other people have this blinding moment that it all changes direction, but that was not us.

Joe: That makes perfect sense. People in the podcasting space, especially– I started off a lot in the WordPress space here. They’re like, “How did you grow your show and how do you get so many downloads a month?” And I’m like, “I don’t know the one thing I did to make that happen. It was just consistency.” Like you said, “Just keep going with it and keep working with it.”

Mike: Yeah. Then sometimes if you’re putting things out there, at least in a consumer product like ours, or maybe your show. I can think of times when people would point a link to us, like the folks at 37 Signals pointed a link to how we handled a challenge that we had that they liked. All of a sudden all this traffic comes over and more people learn about you, so those kinds of things do happen. But 100 of those things happen, so it’s not just 1 thing.

Joe: That’s really cool, and that’s really interesting. I think that’s good advice or maybe encouraging words for people who are starting a product and they’re not seeing the out of control overnight growth that you hear about. Back in Season 1 I talked about how– Or, we talked about how the Olympics were going on, and  my guests and I talked about how you see the gold medalist at the Olympics but you don’t see the years and years of practice that they put before that to get to that point.

Mike: Or the three Olympic Games where they didn’t even medal.

Joe: Right.

Mike: There are– I think this is a terrible thing that’s always happened with the media and these companies, like there are the odd company who’ve done it the first time, but a lot of the really big successes and most of the companies that happened really really fast are people who are repeat entrepreneurs. If I started all over again, could I do it better, faster and cheaper? Maybe. Almost certainly I’d either fail faster or I’d make something as big or bigger faster, but that would have been based on all this experience I’ve been getting doing this.

Joe: That makes perfect sense. My first, again, my first podcast was not great. I learned a lot of lessons, and then I launched this one and I was able to apply those lessons. Much like you are able to apply what you’ve learned over the last 10 or so years, which is fantastic. That’s what people need to hear, because they think– I still think that sometimes, “I’m going to launch a thing and it’s going to be a huge success, and that’s going to be my boatload of cash that I know I need, or deserve, or whatever.” You said that, before we get to the title question I do want to ask one more about the research and building up FreshBooks. You said that you were running a design agency and then you launched FreshBooks, at what point did you decide that this was the thing that you wanted to focus on full time? Or did you basically say, “I’m not going to do client work anymore. I’m going to focus completely on this accounting, invoicing software.”

Mike: Pretty quickly I was excited about the product and got about 80% of my time there, but it was years for that last 20%. I had some employees in that business so I couldn’t abandon them, but what I found was if I spent 20% of my time doing the other thing I could make enough money for them and me, so that I could focus on this other thing. So there was pragmatic reasons. But then there eventually, after probably two and a bit years, I started firing my clients which meant trying to find them good homes, like somebody else who could take good care of them. But that was a progress. That’s the one side that’s nice about a client service business is you can wind things down gracefully over a period of time, if you like.

Break: This episode is brought to you by Pantheon. Starting a new project? Looking for a better hosting platform? Pantheon is an integrated set of tools to build, launch and run websites. Get high performance hosting for your WordPress sites, plus a comprehensive toolkit to supercharge your team and help you launch faster. On Pantheon, you get expert support from real developers, best in class security and the most innovative technology to host and manage your websites. You can sign up a new site in minutes with a free account, and you only pay when it goes live. That is my second favorite feature to Pantheon, only to the easy ability to create dev staging and live servers, and push to GitHub. It’s very easy to set those things up on Pantheon. You can head over to today to set up a free account and pay only when it goes live. Thanks so much to Pantheon for their support of this episode and this season of How I Built It.

Joe: For anybody who’s trying to move from client work to a product, do you think that’s maybe the the best piece of advice you can give? Or is there some other thing you took away from that experience?

Mike: Just know that it’s hard, and the learning curve is really steep. They’re very different kinds of businesses and business models, and things that make them go. I think client service is a great way– If you’ve built a successful client service business, it probably means you have great customer empathy and you understand being able to deliver and focus and execute. Organizing resources, and time. You need all that stuff to start a product company. But the thing about a product company is the way you market is different, and the way you build the product is different. The way you– Everything about it is is different. I think just recognizing that you’re carrying two– They’re just not the same, and being prepared for that learning curve. “I need to unlearn a bunch of stuff here because it’s just not the same game anymore.”

Joe: Yeah. I wish that we had this conversation a year ago, because over the last year I’ve learned that lesson. Though I don’t know if I would appreciate that advice as much as now that I’m on the other side of it, I say “I’m able to sell a $5,000 dollar or $10,000 dollar website to one person, but I can’t convince 50 people to buy my $100 dollar course,” because it is very different. That is for anybody who’s looking to– That’s just fantastic advice. Awesome. Thank you for that. Now I would love to get into the title question, and this is very exciting, because a lot of people that I’ve been talking to lately are the visionaries for the product and then they hired a development team. But in your case, you are the founder and you also built the product. So, how did you build version 1? Then when did you know, do you still do hands on code? Or when did you know it was time to start letting go of that?

Mike: The first thing I should do is come clean and say that makes me sound like I contributed more to the product than I probably did in the end. I did build the first version, I built a prototype to bill my clients. But it was pretty soon after that, like a couple months, that I met my co-founder and he has a doctorate in computer science. He started building things, and then I went to more of a design role. Product design, product management, and then I focused on also marketing and trying to get the business operational and organized, finding customers, all that stuff. There was a division there. I think that’s probably a little more in line with what you’re used to hearing, that visionary that’s more about what the product is and who the customer is, connecting those things to build the right stuff. That is ultimately the role I played. So, sorry. With that clarified the question was, what?

Joe: How did you build it?

Mike: With great customer empathy over a long period of time. Those are some of the key ingredients. I don’t know how technical you want to go when there’s so many ways to answer that question. Is it like, the awareness of your product in the market? Is it trying to figure out what to build? Is it– These are the technologies we chose to build on. How would you–? Sorry to break it down, but that’s a big question to me, I don’t know how to box it into something that I can answer.

Joe: Absolutely. Generally the answer I’ll give, because I’ve gotten this question before, is whatever you’re most comfortable with answering. But I am super curious with the prototype, what technologies specifically did you use? And then, as you grew, whatever you’re most comfortable answering there. Like, whatever you touched the most as FreshBooks became FreshBooks.

Mike: So, my role in growing it up. I think, for whatever it’s worth, [Lamp Stack] at the start. Ruby on Rails didn’t exist, so it was actually pre-2006 when we got started. We were building our own frameworks to do these things and then by the time that stuff came out we were pretty committed already, so Lamp Stack. I think it was MySQL, and I think they had just came out with version three. To back there. Anyway, with that my role again became product management, voice of the customer, and also marketing. Also we started, once we had a website up, and we generated a lot of traffic through SEO and online stuff, and we still do. That was my responsibility as well. But then as soon as we had people coming, then we started having people want to talk to us on the phone, so I did some of that. I did some customer service there and learned about our customers, asked them how they heard about us and constantly asking similar questions. Like, “How did you hear about us? What could be improved?” All that kind of thing to keep furthering my understanding of, “How do we improve? How do we win? How do we go further?” And then bringing that back to the rest the team, like “Here’s what we need to build.” I was pretty prescriptive about, “This is how I’d like it to be built,” as well. Those are always fun, and we had good healthy discussions about that stuff over the years.

Joe: Gotcha. This is really interesting to me, it’s something I’ve been hearing more and more lately, and I don’t know if it’s just because I’ve noticed it more or because it’s becoming more important advice. But having conversations with customers on the phone is something that I’ve been hearing a lot more lately. Maybe it’s that people around my age or younger have an aversion to phone calls, they would rather just do things with email, but it sounds like phone conversations were integral to understanding your product.

Mike: Yeah, our philosophy has always been about customer proximity. Like, “How do you get closer to the customer?” Not only email, not only phone, we were one of the first companies or maybe even the first to do customer service on Twitter.

Joe: Wow.

Mike: They said, “This is another channel to communicate with people, or Facebook, or what have you.” So that’s the orientation. It’s like, “I want to meet you where you live and serve you accordingly.” And all of them are good. Now what I will say is, if you went from email to phone to in-person, and we did do in-person we went to conferences and stuff too. I find that each medium has its own strengths and weaknesses as a research tool. E-mail you’re going to find out about a volume of problems, phone is good for getting some color on those problems, and if you meet people in person you’ll find out what it is that they want that goes beyond whatever you’re doing today. Those are harder. That gets harder. You just don’t get that in email, you might get a feature request but that’s not the same as “I think your platform should be doing this other–” just live face to face is a totally different ballgame. So, I’m a fan of all those mediums for appropriate reasons in each case.

Joe: That makes sense. I think, probably in person people are more likely to be like “You know you should do–” almost like it’s conversational. Did you find that people are less likely to complain to you? Like, not complain. But give negative feedback in-person?

Mike: Probably. But like, my whole thing is like, I’m always asking for what’s wrong. So let’s just take the drama out of that. Be like, “I know we can improve–” I’m always, if people say, one of the things I find frustrating and the thing about me is now I’ll go out and let’s say I give a talk somewhere. OK, we get off this podcast and you say “Mike, great job.” That’d be wonderful. Let’s hope we get there. And I’d say. “Thank you. Why was it great?” Because that’s when you’re live, people will tell you, and saying that. I’ll be like, “OK, great.” Now I can say, “Great. You told me something we did well. Next question is, what can we do better?” I’d do the same thing with this podcast. It’s like, “OK that’s great. That went well. Thank you for telling me that, but what could I have done better?” I think that’s the seeking to understand, and constantly improve. To me it’s a hallmark of– I’ve heard it of other entrepreneurs as well. There’s no, I’m not precious about this thing. I find that so long as we can have a civil dialogue, and you’re not yelling, then I think we can both learn a lot.

Joe: Yeah. That’s great to hear. Because especially as a creator, you get attached to the thing that you build, and if you want it to be the best version of what it is you you have to let go of that. You said, “I’m not precious about this.” I really like– Is that what you said? Precious? I really like that. Because it shows that you know it’s a tool that people use and you want it to be the best tool possible.

Mike: We talk about that a lot with even our design team here, it’s like a lot of designers will come from elsewhere and they’ll be like “This is how it’s done. It’s perfect.” We have a thing called critique, which is you cannot be precious in that room. The idea is, “Nobody’s trying to internalize feedback on work you’ve done as an attack, or as input to help you get to the next level and next better place,” and I’d much rather work with people who are oriented in the second way.

Joe: Yeah. That makes sense, because you’re not going to grow unless you learn how you can do things better. If you just think you make the best thing right out the gate, where are you going to go from there? So, cool. I love that. Let’s talk about, as we kind of wind down time here. It looks like we’re getting close to the half hour mark. I’ve personally seen FreshBooks evolve over the last ten or so years, so maybe we could talk about what are some of the big evolutions that you really liked in the product and what are your plans for the future?

Mike: OK. I think we’ve had a pretty consistent track record of improvement, and sometimes I’ll say the improvements are not as visible, but they are impactful. Because you get a lot of people using your software, sometimes a little workflow we can tune and improve things. My favorite days are when we’re launching stuff, like that’s just my favorite stuff. Favorite days in the office, and I think the big one for me would be “We’ve gone and built a new platform. We decided after all those years, I don’t know if you know this, we have a new version and new FreshBooks.” Seeing the rate at which that is changing and improving is very exciting to me. So we’re now benefiting from the first version was built on frameworks that we built at a time before standards for building companies like ours existed, and now we’re using ember and a bunch of other just more modern technologies. So we can move a lot quicker and deliver better experiences, and that’s been my experience, where we’re not only doing invoicing at this point. We now have, for those who don’t know, and sometimes we’ve had people say “You don’t do double ledger, or bank racks, we can’t use you for accounting. We’ve scaled beyond you.” And we say “Listen. You don’t need to know that stuff even exists in our software today, you don’t need to. But guess what? It’s there. And if you grow to the point where you actually care about that, it’s right there for you as opposed to imposing it on you.” So I’m excited about that too, because we’ve had a lot of customers over the years who are great customers who for one reason or another decided they needed to move on to the next thing. That’s a big thing that’s happened now, and I think what we want to do once we have that that bedrock, “We serve companies that invoice,” now by the way this is a positive development for you as you’re getting into more product stuff. We can help you track other payments and sources of income beyond just invoices, so that’s good. We’re really focused on solving billing problems in general, especially for businesses that send invoices, and we have this accounting bedrock that you can build on and grow. So I think the question is, “Now that accounting bedrock is there, how do we really help you focus on more of your billing issues?” That’ll be the direction of our efforts.

Joe: That’s really cool, and that’s something that especially freelancers or entrepreneurs or maybe solo entrepreneurs are your target audience, that’s something that a lot of people have problems with. Maybe they don’t think to bill on time, or they’re a little tepid about sending that reminder, like “You haven’t paid. It’s been 40 days and you haven’t paid the invoice.” Focusing on, and maybe I’ve misinterpreted what you said, but focusing on billing problems I think really helped your customer.

Mike: Absolutely. I just want everyone to know, what you just talked about is our bread and butter, and that’s that’s there and available today. If you use our product and you send an invoice, you can set things up in an automated way where 15 days later or 30 days later we will take care of you with a simple e-mail saying “This email is now 15 days since sent, will you please–?” We can even help you collect payment. So there’s a lot we do there, and we just see there’s a whole bunch of ways to make your life even better in and around issues pertaining to billing, and we’re excited about that.

Joe: That’s fantastic. Just to bring it back, that competitor that I’m on now does not do any of that. I looked for the automatic late fees, or the late payment reminders. They’re like, “You can do that through a third party.” And I’m like, “Why?” I don’t understand why I would have to pay extra for basic invoicing things, but in any caseb I’ll be happy when the calendar turns and I’m back on FreshBooks. I’m not just saying that because you are on the show, I literally said this to my wife like a couple of weeks ago. I just can’t wait. So, this has been great. I think there’s a lot of really good insight that folks can take away, especially moving from client services to products. We focused a lot there. But just also the customer empathy things that I think people need to hear more of. But I do need to ask you my favorite question, which is do you have any trade secrets for us?

Mike: Trade secrets. Here’s the thing, I think the way we do customer service. One thing I was thinking is “When you’re coming back don’t feel shy about phoning us.” I don’t know if you ever have, or e-mailing us, if that’s your preferred medium. We’re here to help and we even have some services we can help you with your bookkeeping, and move some data from one to the next, so you don’t have to take care of that if that’s interesting to you. Just FYI.

Joe: That is interesting to me.

Mike: Yeah, but then as trade secrets, I think the thing about FreshBooks that’s sort of uncanny and unparalleled is we really care about executing extraordinary experiences every day. That’s what we call it, that’s our mantra. We want to build simple user experiences that exceed people’s expectations, and we love helping people on the phone with a level of customer service that frankly most companies aspire to and talk about. But you know, they really don’t execute against. I think that is– I don’t know. But what I’ve come to realize is that’s a culture thing, and you don’t necessarily get it. You just don’t. That’s our, I don’t know if that’s our trade secret, I think our trade secret is that people really appreciate– Customer service just really matters, and it’s hard to do repeatedly over time at scale.

Joe: Absolutely. I think that is great. Especially because it’s a culture thing, because it does start within the company and making sure that the employees and the founders and everybody are on the same page, about how they feel about a certain thing. When they feel that they execute on it better, so if customer service is the most important thing within the company and the company culture, then you will have good customer service. Mike, thank you so much for your time I really appreciate it. Where can people find you?

Mike: Thanks, Joe. Great being here. If you want to learn a little more about us, or try FreshBooks for free, you can do that at

Outro: Thanks so much again to Mike for joining us. I want to repeat his trade secret, which is the way they do customer service. Don’t be shy about phoning them. They put a premium on good customer service, and between the conversation with Nathalie last week and some books I’ve been reading I think that this is incredibly key at building your own business. Especially for smaller businesses or freelancers, offering that close customer service is the thing that separates you and differentiates you from the larger companies, or the airlines, of the world. Who, for the most part, make it seem like they don’t really care about their customer. I want to repeat that and double down on it. To that end, my question of the week for you is going to be similar to last week. Which is, what can you do to improve your customer service? Or, what do you want to do to improve your customer service? Do you want to implement a ticketing system or do you want to offer phone support? I know that is something that I don’t necessarily want to do, but if my customers ask for it I would do it. It’s me just being me, email is better. I don’t have a support team. But what are you going to do to improve customer support? Let me know via e-mail at or on Twitter @jcasabona. I want to thank my sponsors once again, they are Plesk, Castos and Pantheon. You can find the show notes for this episode over at How I If you liked this episode, be sure to leave us a rating and a review on Apple podcast or wherever you listen to podcast, it really helps people discover the show. And until next time, get out there and build something.

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Feb 12 2019



Rank #4: Kirsten Bunch and Changing Careers

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Over the last 2 weeks, we discussed mental and physical health as it relates to freelancing and self-employment. To round out this trilogy of overall happiness in your career, I’m talking to Kirsten Bunch, who is a reinvention coach. She helps those folks who are mid-career but need a change. She offers some fantastic advice on how to determine if you’re ready for a chance, and the steps you should talk in order to figure out what to do for your next career move.

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Kirsten Bunch: I think the point is you don’t have to stay on the same path just because of some feeling of obligation, and also because you switch careers or because you start your own business maybe there’s– Definitely when you start your own business, there’s a period of time where you are not making a lot of money, but there’s still lots of ways to make money in this world. Switching careers doesn’t mean all of a sudden you’re not making any money.

Joe Casabona: That was Kirsten Bunch. Over the last two weeks, we discussed mental and physical health as it relates to freelancing and self-employment. To round out this trilogy of overall happiness in your career, I’m talking to Kirsten, who is a reinvention coach. She helps those folks who are mid-career but need a change. She offers some fantastic advice on how to determine if you’re ready for change and then the steps you should take in order to figure out what to do for your next career move. This is advice that can come to anybody at any walk of life, and you don’t need to be 10, 15, or 20 years into a career to determine you need a career change. We’ll get into this interview in a minute, but of course, first a word from our sponsors.

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Joe: Hey, everybody. Welcome to another episode of How I Built It, the podcast that asks, “How did you build that?” Today I’m excited to talk to my guest, Kirsten bunch. She is a reinvention coach and entrepreneur, and the topic we’re going to be discussing today is reinventing yourself and launching a new business if you feel stuck. Without further ado, Kirsten, how are you?

Kirsten: Hey. I’m really good, and I’m really good. I’m really happy to be here and have this conversation with you today.

Kirsten: Absolutely, thank you for joining me.

Joe: I’m excited because this is a pretty unique topic for the show, usually we’re talking about more concrete businesses ideas or services. But I think that especially in the space that my audience is in, the web development space, the WordPress space, a lot of people find their way to WordPress web development by feeling stuck. I’m excited to talk more high-level about this stuff. Why don’t we start off with who you are and what you do?

Kirsten: Yes. Like you said, I am a reinvention coach, and a strategist and entrepreneur. By the nature of that, I help people reinvent and refresh their careers. That can mean starting a business, a lot of my clients start businesses. It could also mean switching from one career to another. It also means passion projects sometimes, people who have clients who are writing books as a way to relaunch themselves or starting film festivals in their communities. Things like that. I find that most of my clients, typically my clients are around the mid-career point where they’re looking at what they’ve done and they’re looking at the next 20-25 years because that’s let’s face it, nobody is retiring at the age of 60 anymore. Thinking, “OK. What’s next for me? What am I going to do?”

Joe: Absolutely. First of all, I don’t know if I would have the ability to retire. I mean maybe I’m about halfway there, a little more than halfway there. Maybe I will want to retire. But I feel like I’d be pretty bored if I retired at 60 or 65. But you mentioned this in the pre-show discussion too, about passion projects, and I like that. Mostly because my career manifested itself out of a passion project. I was doing web development on the side, and it was a hobby, and I liked it. Then I made that my career basically from high school, I was doing that full time– Or, I was doing it while going to school, I should say. I like that too, and one other reason I like that is because I’ve heard from a lot of people in my outer circles that they don’t have a hobby. They basically work, and then they go back to work, and helping people find and pursue passion projects is important to me because I think that you should have other interests outside of your day job.

Kirsten: I think that’s true because I think– One of the things that I coach my clients on is not everybody’s ready to jump out of their career or jump out of their job, either for financial reasons or for identity purposes. I don’t recommend just quitting your job from one day to the next unless you’re prepared for what that means, and we could dig into what that means if you want. But one way to get your toes wet is to do a passion project. It’ll help you feel better about being in a job that maybe you’re not thrilled about, because you’ll have something else to think about, but it’s also a way– Like I said in the beginning, it’s a way to relaunch yourself. I’m working with a woman right now who in order to– She’s a celebrity stylist, and in order to relaunch herself and figure out where she’s headed next she felt the urge and felt the need to write her story. She’s writing a book about the vulnerability of beauty, and all this stuff. Cool stuff. It’s a way for her to take stock of where she’s been and who she is now and where she’s going.

Joe: I love that. That sounds cool. I think it flows very well into the next question that I had for you, which is “How do you know when you’re ready to make a career switch?”

Kirsten: I think if you’re uncomfortable with what you’re doing now, and that feeling of uncomfortable-ness isn’t going away, I think you need to examine that. That doesn’t mean you need a career switch necessarily, but it means that there’s something going on. I do a lot of speaking, and I always tell my audiences I have this whole story about my own reinvention, where I ignored the fact that I wasn’t happy in the career that I was in and I was moving from one job to the next and just doing the same thing. It’s like, what’s the saying– Doing the same thing over and over again and expect different results. So what I say is that you can distract yourself from the truth, but the truth isn’t going to go away. If you feel like that’s what you’re doing, is you’re distracting yourself from the truth, that you’re not in the right place. Then I would suggest getting some help to figure that out, and not panicking. Please don’t panic. It’s OK. It’s all going to be OK, and you’ll figure it out.

Joe: I think that’s great. Not necessarily career switches for me, but both times I decided to leave my current job they came after a longer period of “What am I doing? I feel like I’m not growing,” in one instance. I felt like I was falling behind. I felt like I was the person who knew the most, and I didn’t want to be that. I was 26. I didn’t want to be the most knowledgeable person at my company, because there’s so much more to learn there. Then in my previous job, my wife and I had just had our first child, and I was re-evaluating based on that, and the time I was spending at work versus with my family. But I like that if you’re uncomfortable with what you’re doing, you need to examine it and don’t ignore it. Moving forward in this interview, we talked about this in the -pre-show, creating the persona of somebody who is ready for that career switch. As I ask the next set of questions, maybe we can keep that person in mind. Someone comes to you, and they say “I’m ready for a career switch, I’m not quite sure where I want to go next. What do I do?” The follow-up question I always ask in this interview is, “What kind of research do you do?” So how would we figure out where to go from here?

Kirsten: Yeah, no, definitely. It’s a great question. A metaphor I like to use, and I stole this from my branding team, but a metaphor I like to use is “What car–?” If you think about cars and you think about “If you can be any car you want, what car are you now and what car do you want to become?” And it’s not “What car you want to buy,” but “What car do you want to be?” So when you think about the cars, and you think about the car you want to become, you want to think about things like the size of the car. Because that in your career represents community. Have you been working in a big company and you want to be on your own? You want some space, you want to be a solo solopreneur, and you want to explore what that is? Or have you been working on your own in a small business and you miss that bigger crowd around you? The car analogy is, “Do you want a mini or do you want to do you want an SUV? A big SUV or a van?” Then also your values come in. Do you want the gas guzzler in your career, do you want to work for something that’s not mission-focused per se, and you want to work for a big company that does something that maybe isn’t– Like do you want to work for a tobacco company, or something like that? Or do you– Is there something within your values that is pulling you, like you feel like “I want to do something about climate change.” Or “I want to do something about animals,” I don’t know, food systems. So with the car analogy, it’s “Do you want a gas guzzler or do you want a hybrid? Do you want an E-car? What are you looking for?” I think figuring out those two things, what are the values that you’re looking for in your career, your new career and what, how– Sorry, I’ve lost my train of thought. But how do you show up with– If you think about it in the sense of car, what does your car look like and what are the elements of that car? The features is the word I’m trying to find.

Joe: Absolutely. That makes perfect sense. Again thinking back to my own journey, I worked at a big university which is essentially like a Fortune 500 company without the bankroll. Then I went to a small team, and now I’m solo. I made those choices at various stages. Then I like the idea of “Do you want a gas guzzler versus an electric car?” Or “Do you want to work for a company maybe where you do a specific job, and you like doing that job, or do you want to work for someone that has a very clear mission that aligns with your views?” If you dig on what Ben and Jerry’s is doing, they have a very clear mission. Maybe that’s something that you would consider as well. I like that a lot.

Kirsten: Yeah. I think that the idea of being an entrepreneur or working for somebody else, do you want an automatic car do you want a stick shift or a standard car? Because if you’re an entrepreneur, it’s all on you. You’ve got to drive that, and you’ve got to pay attention to how you’re shifting and all of that. That’s not to say in automatic if you’re working for somebody else you don’t have to do it, but it’s a little bit more that somebody else is driving the ship and you’re steering your part of the job.

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Joe: The next question that I would have is, what am I going to do? I’ve been a web developer for 15 years, I’ve worked at– My old man worked at Verizon and before that Bell Atlantic or Ninex and Ma Bell, or whatever. He worked at the same company for his entire career. How do you figure out what to do next, as far as the actual doing the job?

Kirsten: The question I get a lot is, “How do I figure out my passion?” I’m not– Actually, I don’t know. I’m not a passion person. I’ve never really figured out my passion, and my passion has been trying new things if anything, that’s what my passion is. What I say to people is, instead of– “Forget about your passion. If you know what that is, awesome. Follow that. But don’t freak out if you’re just like, ‘I have no idea what that is.’ Follow your curiosity instead and follow the things that are catching your attention, and talk to people about them and read up and talk to people who are working in that space.” For me, my reinvention story was about becoming an entrepreneur and starting my own business. I had never done that, I didn’t– I don’t come from a family of entrepreneurs, my parents were school teachers, and I don’t know a lot of people who had their own business. I do now, and I know tons of people. But my curiosity was about “What would it be like to run my own business? What is that even about?” I think back of how naive I was a couple of years ago compared to where I am now, I’m still incredibly naive, but it can be a curiosity around a specific function, or it can be a curiosity around an issue, or something else.

Joe: I like that point a lot, follow your curiosity. It’s almost like your freshman year of college, taking a bunch of gen-ed classes to see which one you like the best before you determine your major, is what I thought there. I like that answer too, and it resonates with me in an interesting way because I knew from the age of 12 that I wanted to work with computers in some capacity. I was very lucky in knowing exactly what I wanted to do from a pretty early age. Before that, this is a little known fact, and I wanted to be a Catholic priest because I was an altar boy and that seemed like the next logical career move to an 11-year-old or a 12-year-old. But then I discovered computers and I felt like that was a lot more lucrative.

Kirsten: Yes, probably.

Joe: Follow your curiosity and figure out what’s catching your attention. I think that’s a nice takeaway.

Kirsten: You bring up a really good point about this idea of– This happens to a lot of people who are mid-career, that you’ve been on a path and I hear all the time “I’m just going to continue this because this is the way I’ve been going, and this is what I’ve worked so hard to get to.” We take time, we pay attention to our education, we build our skills, and we build our networks, and it’s a little disconcerting, or it’s a lot disconcerting if you get to a point where you’re just– It’s back to owning your truth, and you’re like “I don’t know if this is right for me anymore.” Something in your gut is telling you that it’s not right, but you’ve invested so much, so why not just continue on that path? The difference is now in this day and age, and we’re really the first generation– It’s true for men and women but particularly women, this is the first generation of those of us who are in our 40s and 50s where we have the luxury of time, and we have the luxury of technology and the way cultural norms around work– How they’ve shifted. We have the luxury to ask that question, “What else can I do?” And have a long enough runway to figure that out. Because we’re not, God-willing, we’re not dying at the age of– In our late 50s or early 60s anymore. A lot of us are living much longer. Like I said in the beginning, a lot of us want to be productive and engaged. The idea of retirement is just completely changing.

Joe: Right. The retirement age was determined based on the average lifespan. You retire, and then a few years later you’re probably not going to be alive anymore, and that’s not the case anymore. You retire at 65, and you could live another 25 years or 30 years. All of my wife’s grandparents are in their late 80s, which is not what it was like when they entered the workforce. I like that a lot. Then people who are mid-career and on a path generally want to stay on that path, and I think that’s absolutely true. Especially with the increasing cost of college, I spent over $100,000 dollars or whatever on a college degree, and now I’m not going to use that degree. That weighs on your mind a little bit.

Kirsten: Hopefully by the time you’re mid-career you’ve–

Joe: Yeah, that’s true.

Kirsten: But I know for people who are in school now, that might not be the case. They may be carrying that debt through for years and years and years. I think the point is you don’t have to stay on the same path just because of some feeling of obligation, and also because you switch careers or because you start your own business maybe there’s– Definitely when you start your own business, there’s a period of time where you are not making a lot of money, but there’s still lots of ways to make money in this world. Switching careers doesn’t mean all of a sudden you’re not making any money.

Joe: I think that’s– To drive that point home, before we get on to the title question, I read an article that I like that basically said “If you’re not willing to do something for three years, you shouldn’t think about it.” That falls in line with the idea that if you start your own business, you’re probably not going to make good money or replace your previous salary for about three years as you get up and running. You’re not immediately going to make what you are making at your old established job, so I like that. That’s stuck with me. I’m about to enter year three of my business, and things are going pretty well, not as well as I want them to be, but I’m also– I’m a millennial, so I don’t have any patience. I really like that, that change can be hard, but you shouldn’t stay on the same path because you have a feeling of obligation towards it. Or towards what you’re currently doing, I should say. Let’s get into the title question, and I have followed my curiosity. Let’s pick an example that you’ve mentioned before, let’s say I want to write a book. I’ll say a fiction book because I’ve written technical books. I want to write a work of fiction. How do I build my reinvented career or my reinvented passion project?

Kirsten: If it’s about writing a book, writing a fiction book, I don’t work with people who write fiction, so it’s a little bit of a difficult scenario. But let me talk it through. With writing a book, there are a lot of book coaches out there that can help you write your book. If you have no experience writing at all, I would say start with taking some courses where you’re writing within a group, and people are giving you feedback. I know Gotham– I forget what it’s called, but it’s like Gotham Writers or something like that in New York that has a lot of online courses, and they’re always really great. But I think the thing is that if you want to write you’ve got to write, and that’s like with anything. If you want to start a business, you’ve got to start a business. You’ve got to take action. That’s true– You could give me any scenario, and I would say, “Take action.” If you want to write, start writing. Stop talking about it, and I think there is a big– Don’t stop talking about it, but put action behind the talk. I think there’s a lot of people that are always like, talk talk talk. “I’m going to do this,” and 10 years later, you see the person and you’re like “Are you still talking about this, and you haven’t yet done it?” I think whatever it is that you want to do, follow your curiosity, and take action.

Joe: Nice. Don’t just talk about it, actually do something. If you want to write, you’ve got to write. I love that. I had a track coach– I was on the field part, I didn’t do much track, but I did the field part. Our track and field coach [Mr. Diebold], on the first day of practice, said to the runners, “If you want to run fast, you got to run fast.” Then to the shot putters, “If you want to throw far, you got to throw far.” I remember that, and I’m like, “I want to throw far.” I think that’s a great piece of advice, something that I’ve heard a lot, and going back to your initial point, start talking to people. Take some courses to set you on that path. Let’s speak a little bit more generally now, as far as reinventing goes. Take some courses, and is the first step figuring out your first step? Is the first step in reinventing your career, figuring out exactly what you need to do?

Kirsten: Yeah, no. Not necessarily, because some people don’t know. A lot of– Some people say “I know this doesn’t feel right, what I’m doing now, and I want to figure out what else I’m doing.” If I say to them, “Just start taking action or figure out your first step.” They’ll be like, “I don’t know what that is.” Then they’ll run around in a circle, and that’s–  You get dizzy. I think that one of those– As I said in the beginning, it’s like owning your truth. What is it that you’re experiencing now that doesn’t feel right to you? Looking at that, and it does help a lot to get some help by maybe there’s an HR person in your company that also has coaching skills that could help you talk that through. I think there’s a sense of vulnerability there, you have to be willing to own your truth and– I keep saying that, but in talking to people about it I wouldn’t go and announce it in the company newsletter that you’re seeking your next career necessarily, but if you have trusted people where you are, have a conversation about what it is you’re trying to figure out. Get some help thinking that through, what is it that doesn’t feel right? What is it that–? In some ways, it’s simple. A lot of us know what we want to do, we’re just afraid to admit it to ourselves because we think we’ll fail or we think it won’t work, or we think we don’t have what it takes. Or my favorite is we think we need to spend two years gathering every single piece of information and listening to every podcast and reading every book until we make any steps towards that direction at all. You’re not going to know if it’s right or not unless you at least start taking a little bit of action.

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Joe: In the context of doing things online as a software developer, “Iterate quickly” is “Do something, see if it works out, you can always adjust it later.” Right? This is not like building a skyscraper where we need to make sure all the plans are exactly right before we start building. This is more malleable than that. I’ll link to a previous guest, Scott Bollinger, that basically talked about that. “Launch as soon as you can, because you don’t want to spend two years throwing yourself into this thing and realizing that it’s not the right thing to do once you start doing it.”

Kirsten: Absolutely. I talk to people about having– People have college funds for their kids, they have retirement funds. I talk to people about having reinvention funds. The reality is because of the way, as we talked about because people are retiring later and because of the way we’re working now, the reality is that you’re probably going to reach a point in your career where you’re going to look to reinvent yourself. Whether that means starting a business or switching careers, isn’t it wonderful to have a fund that you can pull on so that you don’t have to be so stressed out about your reinvention? Because a lot of the times– You probably know this as an entrepreneur, it’s hard to know what to spend money on. That fear of, “I only have– I have no money because I didn’t plan for this. I don’t want to hire this web developer to help me,” or “I don’t want to hire this coach,” or “I don’t want to hire this bargaining person because I’m going to go into debt.” But if you have that reinvention fund, it makes it a little bit easier, and it makes it a little bit more– It takes the fear away a little bit.

Joe: Absolutely. Even as somebody who does run their own business, you should– I got some great advice from a friend Jen Bourne who said that you should have a rainy day fund. Take some part of the money you make every month and put it into a separate fund because you’ll probably have that feast and famine. There’ll be good times where money is coming in, and there’ll be slow times, so you need to manage that a little bit. So, “Have a reinvention fund.” I think it’s The Richest Man in Babylon, have you read that book?

Kirsten: No.

Joe: It’s about investing, but the lesson is really good. You take 10% of your income no matter what, and you put it somewhere. You take that, and you invest it in whatever you think you should. This was written a long time ago, so it talks about investing in a farm or whatever, but reinvention fund means you’re investing in yourself. You’re taking that 10% for your future self to help reinvent yourself.

Kirsten: Absolutely. Investing in yourself as one of– It’s a big thing. We’ll invest in our kids, and we’ll invest in our homes. But when it comes to investing in ourselves, a lot of people give a pause around that. They feel like, especially people in mid-career who are just like “I spent my money on my education,” right?

Joe: Right.

Kirsten: But the reality is that it doesn’t stop, the idea of– Sorry. Investing in yourself is lifelong. You’ve got to keep doing that.

Joe: Absolutely. As we wrap up, I will point to one more book that I think drives this home, especially for entrepreneurs. That’s Profit First, which talks about taking 5% of the money that you make there and just put it in a– That’s your bonus, otherwise you’re not getting anything out of the business. You’re working harder than you would in a full-time job, and you’re not getting anything from it, so as we record this I just used my Profit First money to buy this beautiful fountain pen that I wanted for a long time. It’s the Sailor Pro Gear, I don’t know if you’re into fountain pens, but it’s a very nice pen. I had the support of my wife to buy it, of course, but I feel like I’ve gotten something out of the business this quarter because it’s something I’ve wanted for a long time.

Kirsten: I love that. I think especially as new entrepreneurs we are– Gosh, the money thing is so hard. I love the fact of just buying yourself something nice even if it’s– go and have a spa day or buy yourself a nice pen, or whatever.

Joe: Yeah, exactly. Get something out of your business that you maybe wouldn’t get out of the full-time job, and along with that proper money management is important. I think your point about the reinvention fund and reading Profit First, manage your money, and that gives you freedom. I think that those are very good points to take away. Let’s– I usually like to ask you what your plans for the future are here, but we haven’t talked specifically about you that much. Why don’t we get an idea of what you would do for somebody, for our persona that we’ve created as far as guiding them, and what your plans for the future are?

Kirsten: Sure. I think I understand your question.

Joe: I threw like two or three in there.

Kirsten: OK.

Joe: It’s– What do you do currently and what do you hope to do in the near future?

Kirsten: Got it, yeah. Like I said, I’m a reinvention coach and strategist, and I help people figure out their next act. My book is called– I have a book that came out last year, it’s called Next Act: Give Back and it’s not about volunteering, it’s not about giving money. It’s really about how you give back to yourself, how you give back to the dreams that you had in college to do something that you wanted to do, and you got carried away on a career track that has been good or bad depending on your situation. But now it’s time to reassess what you’re doing, and for me, I continue to work with people who are at that point of their careers where they’re asking “What am I doing here and what else could I be doing, and what’s next?” That work isn’t going to change, because I absolutely love that work. This is what lights me up, and I get up excited, and I’m excited every day to work with my clients and see what they can do. For me, what I’m doing now is focusing on how to be a better business person, and how to learn how to be a better entrepreneur. “What do I need to learn?” Which is tons of stuff. I’m working with a branding agency right now to make my brand a little more polished, and I guess more official-looking. One of the things that I found when I started was that I was talking to too small of an audience. So I’ve expanded, and I’m working with a branding agent to expand who I’m talking to with my messaging. The future really is “How do I help more people, and how do I make more money helping more people?” Basically. That has to do with group programs, retreats, things like that. For me, everything has to be fun, otherwise, I don’t want to do it. I can’t force myself to do things that aren’t fun. So, that’s where I’m headed.

Joe: I like that a lot. “For me, everything has to be fun.” In both of our situations, we’re probably not just happy with the paycheck, I need to be fulfilled by my work, I want to be able to do things that I enjoy doing, and everything has to be fun. So, cool. As we wrap up here, I do like to ask my favorite question, which is, do you have any trade secrets for us? You’ve given us a lot of really great information so far, is there–? What’s maybe the one big takeaway that you want listeners to have?

Kirsten: I think the one thing, and I don’t know if it’s a trade secret, but the one thing that I have learned is that you can’t do everything by yourself and you’ve got to invest in your business. That may mean taking on debt, and if you’re a solopreneur that could mean borrowing money from people or having credit card debt, or there’s other ways to take on debt. But you are not going to grow unless you’re investing in yourself, and in what you’re trying to do. For a long time, I sat and didn’t want to spend any money, didn’t want to invest in myself. I tried to do it myself and what you were saying– There’s a lot of things that I’m good at, and there’s a lot of things I’m not good at. Like marketing, forget it. I have no idea what I’m doing most of the time. But you have to figure that out and own that. What are you good at, what are you not good at? Get help and stop trying to do it yourself, stop trying to bootstrap it as a badge of honor and invest in yourself. You can either– Money and time have an interesting relationship. You can either spend a lot of time, or you can spend some money and spend less time.

Joe: “Money and time have an interesting relationship.” I love that. When I was younger, I had so much time, and I would do everything. I had all the time and no money. Now that I am older and I have a family, time is the most valuable thing to me. I will happily spend $200 dollars if it saves me several hours, or whatever.

Kirsten: Yes, absolutely.

Joe: Yeah. I love that, “Invest in yourself. You can’t do everything by yourself, and you may need to take on a little bit of debt. That’s perfectly fine.” People who start brick and mortar businesses before the age of the internet had to go to the bank to get a loan to buy property. The idea is that they were investing in their future self to be able to pay off that debt and be in a better place, so I think that there’s an interesting look at debt today with the whole Total Money Makeover movement and no debt ever. Sometimes you need to invest in yourself, and that future investment will hopefully pay off if you do your due diligence. So Kirsten Bunch, thank you so much for joining me today. Where can people find you?

Kirsten: Thank you. This has been great. They can find me at my website, and it’s I’m also pretty active on LinkedIn, more than any of the other socials, although I am on all the others. You can find me with my name, pretty– Somewhat unusual name, although there are other Kirsten Bunch’s in the world. I have a blog that comes out weekly that’s called Changed the World In a Hot Flash that people seem to like. That’s something you could sign up for if you’re interested in connecting with me.

Joe: Awesome. I will link to all of those things and everything, especially the books, we talked about a lot of books today– That we talked about in the show notes over at Kirsten, thanks so much for joining me today. I appreciate it.

Kirsten: Thank you. This has been great. Thanks a lot, Joe.

Joe: Thanks so much to Kirsten for joining us today. Lots of takeaways. There are a lot of takeaways from her interview. She also gives a ton of advice in her trade secrets, and you can’t do everything by yourself. “There is a lot of things that I’m good at,” she said, “And a lot of things I’m not good at, and “That money and time have an interesting relationship.” I liked that one. She said you may need to take on debt, which we may differ on the philosophy of that. I try not to take on any debt if I possibly can, but the overall message here is invest in yourself. This is incredibly important. You need to invest in yourself and the tools that will help you become what you want to be. I think that part is incredibly important, and if you do need to take on a little bit of debt to get that education you need or the certification that you want, then so be it. The idea is that you should believe that that debt is an investment and you’ll be able to pay it back in a short amount of time. So definitely check out Kirsten and all of her fantastic resources, which will be linked in the show notes over at Thanks so much to our sponsors, Ahoy! Creator Courses and Pantheon. We would not be able to do the show without them. My question of the week for you is, “Have you ever felt like you needed to make a career change, and what did you do to mitigate that change?” Let me know on Twitter @jcasabona or via email at Thanks so much for listening. If you liked this episode, then please share it with somebody who you think will benefit from it, I would appreciate that. Until next time, get out there and build something.

The post Kirsten Bunch and Changing Careers appeared first on How I Built It.

Jul 23 2019



Rank #5: Jen Jamar and Marketing

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Jen Jamar is a marketing strategist who currently works for Modern Tribe. Jen really knows her stuff, which I loved because I learned a ton. And the best part? We talk about a strategy for marketing that won’t cost you thousands of dollars in Facebook Ads! In this episode we cover all sorts of stuff like Field of Dreams marketing, how to properly connect with people, and establishing your authority online.

Show Notes

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  • Jilt: The easiest way to recover abandoned shopping carts on WooCommerce, easy digital downloads, and Shopify.
  • Liquid Web: Fast, Managed WordPress hosting whether your users are logged in or logged out. Get 50% off the first 2 months.
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Intro: Hey everybody and welcome to another episode of How I Built It! Continuing our series on How You Build a Business, today I get to talk to Jen Jamar about Marketing Strategy. Jen really knows her stuff when it comes to this topic, which I loved because I learned a ton. And the best part? We talk about a strategy for marketing that won’t cost you thousands of dollars in Facebook Ads! We’ll get into that in a minute, but first, a word from our sponsors…

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And now…on with the show!

Joe: Hey, everybody. Welcome to another episode of How I Built It, the podcast that asks how did you build that?

Today I have a very special guest with me. We’re not talking about building a specific product, we’re talking about building a marketing plan, which is something, frankly, I don’t know anything about, so I’m really excited for my guest. I forgot to ask her how to pronounce her name. Is it Jen Jamar?

Jen: It is Jen Jamar.

Joe: Alright. Jen Jamar, how are you today?

Jen: I am fabulous, thank you for asking.

Joe: Excellent. Excellent. Why don’t you tell us a little bit about who you are and your background for what you’ll be talking about today?

Jen: Sure. I’m a marketing strategist over at Modern Tribe. We make the Events Calendar, event tickets, and a whole bunch of other event management plans. Got over eight million downloads, so there’s a good chance a lot of people listening have used one of our plugins before. I primarily work on our products team doing marketing. So that means when we’re launching a new product, when we’re trying to grow the downloads of our existing products, and newly, we’re launching some new Sass products and incubating some additional ones. We’re doing some marketing planning for that, as well.

I’m pretty active in the WordCamp community, speaking at WordCamp Minneapolis and a few others. I’ve gotten a good sense of some of the marketing challenges that plugin authors, theme authors, and even just general freelancers face with their business.

Joe: We kinda set this up because Modern Tribe did sponsor the show back in season three. We got to talking about marketing strategy, and I thought that this would be a good topic to talk about. I generally try to keep the show to a half hour, so we’re going to pack everything we possibly can in. If we go over, perhaps you can get more over on our Patreon page.

For now, let’s talk about this. This is my biggest problem. I take a very Field-of-Dreams approach to marketing. I always think I’ve built something good and, therefore, they will come. Let’s start with the first question, I’ve built it. How do I get them to come?

Jen: Oh, that’s a good one, and that comes a lot. I think a lot of times people build what they love or what they want themselves, and they don’t spend as much time thinking about why do other people need or want to use this? More specifically than that, what problem can my thing solve for them?

If you can figure out what problem your thing solves, and it probably won’t be the first one you think of, then you can start finding out who those people are, and you can start with your own network; just say, “Hey! Do you guys know anybody who has X problem that I can talk to and see, hey, what do they think about my product? Is it worth the money I’m charging? Or would they use it for free?,”

Joe: Nice. That’s great. A lot of people on the show have said that they scratch their own itch. So they’re solving a problem that specifically they have, but not everybody might have that problem. Let’s say I built an add-on for PowerPress, which is the podcasting plugin that I use. It does things like ad sponsor, like a sponsor, like a sponsor post type and a transcript post type, and stuff like that. I was scratching my own itch there.

I think I view this as a problem that other podcasters have, but you said talk to other people in the space. What do you think I should do? What’s my step one? I have the code on the repo. What’ll I do? Do I just give it to people and say, just tell me what you think? Do I ask them canned questions, or anything like that?

Jen: No. The first thing you do is go find a couple of those people and literally talk to them. You don’t have to spend days and days and days doing this kind of research, but one or two conversations are going to give you the right direction to go in. Talk to a couple of your podcaster friends and say, “Hey! I built this thing. Is it something that would be helpful to you?” That simple question. They’ll probably come back and say like, “Heck, yeah, but wait. Does it do this? Does it do that?”

That’s the different between whether you’re offering something for free, or whether you’re offering something as a premium product.

Joe: I thinThat’s great advice, because certain things might be valuable to everybody but not necessarily worth paying for. Some of these events features that will save people time and money, correct me if I’m wrong, those are the things where I say, “Hey! I’m solving this problem for you. This is a problem that I know you have, that I’m going to solve, and it’s going to save you X amount of time, or X amount of dollars.”

Jen: Yes. You can also scale this much bigger. Once you’ve talked to a couple people and they’re like, “Yeah, yeah, this is something that’s valuable to me. I run into it.” I generally think if more than two people have run into the problem, there’s probably a whole bunch more of them that I just don’t know where they’re at, and I need to find them.

That’s the next challenge of marketing. It’s not like, “Hey! Where do I jump in and start selling?” Or “Do I put it up for free and start giving the code away?” It’s how do I get in touch with these people and get in front of them? Because you can make the best product in the world. It can be the cheapest product in the world. If nobody that wants it finds it, you’re not going to have any sales or any downloads or anything like that.

This is where that whole, “Let me Google that for you” comes in handy. It sounds silly, but do some search terms for questions you think people would be asking that would have them land on your product. This isn’t really keyword research or podcast stuff, this is about finding like, hey, where’s the forums where people are talking about podcasting, in this instance?

Not just talking about like sponsoring a podcast, or necessarily the technical side of podcast, but the DIY’ers who are really going to need this type of technology to make their podcast go more smoothly; they might be just starting out. That’s the person you want to capture, because you don’t need to compete with all those people who offer a more comprehensive all-in-one solution.

Joe: And that makes a lot of sense. Those DIY’ers, I just recently heard this, I’m not going to make a page for this plugin that says “sponsors custom post type, transcripts custom post type.” People aren’t Googling that. They’re Googling the problem they have, and I’m trying to help them solve that problem.

So just like talking about all the fun technical stuff that I think is cool, isn’t probably the best marketing copy.

Jen: Not unless you’re marketing to people who are interested in the technical part. Like if you’ve got some way cool customizations you can do because of some technical piece you’ve written in there, great. Then write it as techy as you want. But if you’re writing it for people who are trying to avoid the techy stuff, because something like transcribing it automatically is a huge time-saver, or people who are trying to, like we said, the DIY’ers who don’t have a team behind them … I don’t know if you’ve ever tried to transcribe audio. I have. It’s a pain in the butt. It takes forever.

If you hire somebody, it gets really expensive, especially if you’re doing regular podcasts like you do. I wouldn’t want to incur that monthly fee. If you write a plugin or a code snippet or something that will do it for me, boom! Here. Take my money, because you just saved me several hours or X amount of money that I would’ve been spending elsewhere.

Write your page against that. Like, do you want to save two hours per episode in transcription time? Do you want your podcasts automatically transcribed? Are you repurposing your content elsewhere? We’ve got something that will transcribe it so you can turn it into a blog post on XYZ site. All of those things are things you’ll want to focus on.

Joe: So focus on solving problems, answering questions related to that problem, and then … So, you’re set. Let’s say we have our marketing page now. How do I get people to come to this marketing page? Are there good advertising channels? Or should I try things organically at first? What’s my first step for actually getting people to come to this page?

Jen: That depends on where you’re at and how much research you’ve done. If you know, like genuinely know, there’s a high demand for your product, go ahead and pay ads to get in front of those people, assuming you also know where those people are hanging out.

If you’re not sure, and you’re assuming there’s a high demand because you’ve talked to a couple people and they all said they want it, but it’s not a statistically significant sample yet, that’s where I prefer to not start, by spending money, because I don’t want to throw money away, especially if I’m kinda bootstrapping it and this is maybe more of a passion project that I’m trying to see will it take off into something? Like you said, you built it to solve your own itch.

Then I recommend doing some organic stuff, especially in the WordPress community. Like we’re all part of different WordPress groups and Slack channels and local meetups. So there’s ample opportunity to go in and talk to people and say, “Hey! I built this. Do you know somebody that I should be sharing this with?” Or “Do you know someone who might find it useful that you can share it with?”

It’s not so much about leveraging those connections just to promote your stuff, but it’s about figuring out where … Like getting advice on where they think you should spread the word. I know I get that all the time. I don’t remember what it was, but somebody was asking me recently about using a builder plugin. I’m like, “Hey! There’s this whole community on Facebook. This is a specific group you should go join.”

So when it’s your product that’s solving something, somebody’s going to say, like our podcast example, like, “Hey! There’s this whole user group of these podcasters, and I bet they would be interested. Why don’t you go ask their admin if you can share your link over there?” Now, boom! You’re getting some of that traffic. As you start to get more traffic, you can look at like where’s it coming from? Am I doing stuff on social that’s bringing people in? Am I starting to see Google traffic trickle in?

Based on the people who are interested in your product, you can even start building out specific landing pages, so then it does target different keyword traffic. Google AdWords used to be great for finding out keyword traffic volume, and it’s not anymore. If you want to get into that, buy your buddy who does SCO lunch, or plan to spend some money investing in some different software that’ll get you more accurate search results on that.

Joe: Cool. That’s great. I will link to Rebecca Gill’s episode of the podcast. She talks about all sorts of different tools like that. That’s really interesting. I find, at least for me, starting out, it’s very hard to understand who exactly my audience is, even with the podcast, I’ve been going for three seasons. This is season four. I have over 2,000 downloads per episode in this and that, and I don’t really understand the audience.

Recently, at the time of this recording, I got some advice to kind of install the Facebook Pixel to … And not do any advertising. Just kinda let it run to see what kind of people are visiting my site. Have you found that has been effective for you at Modern Tribe, or is there kind of another way that you prefer to understand your audience and who’s visiting your site?

Jen: That’s a great question. At Tribe, it’s a little different because we don’t necessarily have people visiting our site who are using our plugins. Since they’re available in the repo, they can download it from there and we don’t have any visibility to any of their information other than in addition to our download count and to our active install number.

In that sense, we don’t know who’s using our free plugin, but we do have an option where if people would like to, they can turn it on and off. They can display that this is powered by the Events Calendar, in which case, we can do some searches and gather some data about, okay, what types of sites now are running it? We still don’t have the information about the site admin themselves, or the person that downloaded it, but we’ve got a sense of what the site is about.

With our premium plugins, of course, we have all kinds of data, because their license key is active on a specific site, and they’ve given us data during purchase. With those, we do take a big chunk of that and say, “Hey, wow! We’ve got a whole bunch of churches running our plugins, or we’ve got a ton of higher ed running our plugins”.

Let’s say, maybe we need to design a landing page so that those people know which of our plugins are most useful for them, especially if they’re using one and it turns out that a couple others could make it an even better experience. It’s not just about selling them more stuff, it’s about giving the complete package so that they don’t have to look elsewhere.

Joe: That’s really interesting, especially what you said about the repo, because I’ve talked to a few plugin developers, and they’ve said that using the repo is great for exposure, but it sounds like it might not be the best thing if you want to build a kind of direct marketing plan. What’s your opinion on having a free plugin on the repo? Without getting you in trouble.

Jen: No, no, no. I think it’s great. I mean, that’s where we got our start with the Events Calendar. Because of that, it’s created a steady stream of users. The Events Calendar, to be clear, is on its own, a fully functioning piece of software. It is not something that is missing features or a light version.

Our Pro version, however, adds even more functionality. It adds in premium support and all those things. What we find is people are like, “Cool. I’ve got the Events Calendar. It does everything I need it to do, but wait. Now I want to do recurring events,” or “Now I’ve got support and I want like an answer right away. I don’t want to wait for like when there’s a pass on the dot-org repo support forms.”

So people kinda upgrade naturally. There’s that pattern, it’s called the premium model. Get them into free, they want to upgrade into one of your paid or add-on additional ones like front end of exhibition is our paid community events plugin. That’s not built-in.

To step back to somebody who’s starting out, it’s great, because you get your name up there. Look at how many other names are up there. If there are 80 different plugins with 80,000 downloads apiece, yours probably isn’t going to show that high. You’re probably better off still putting it there, because it doesn’t hurt, and then leveraging some of the other tools to get it shared in front of the audience.

Like say if WP Mayor will do a review. Check if there’s something newsworthy, head up WP Tavern and see if they’ll write something about it. There’s the WordPress weekly email newsletter. You can send it to them and say, “Hey! I just launched this new plugin. Will you give it a mention?” If they think it’s interesting, they’ll do that. You don’t have to pay for those things, you don’t have to do extra stuff.

To go back to the dot-org repo, the other piece of that is there are new things like the Freemius plugin that Vova Feldman created, that allow you to prompt your users when they install your plugin, if they’d like to share their contact information, or if they’d like to share data with you.

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I’d say the percentage that opt in varies, but it’s usually more than most people expect. You have to know your audience. When you’re starting out, you don’t know your audience, so it’s not going to hurt you necessarily, but if you have an established audience where you haven’t asked that before, they’re probably going to be like, “Wait. Why is this prompting me for this? Why are you suddenly changing gears? Are you selling us out?” Just be aware.

So if this is your first time launching something, great idea. If it’s your third, fourth, fifth product and you haven’t done it before, you need to be more thought … Still a great idea, but be more thoughtful about how you approach it.

Joe: So users will have like an expectation, right? If the people have downloaded a hundred thousand versions of other plugins I’ve had, and then this brand new one, I’m like, “Hey! Give me all your data,” they’re going to be like, “Why?” It’s a communication thing at that point, like, “Hey, I really want to get to know you better,” sort of thing.

Jen: Yeah. And it’s also I think just about transparency. One of the concerns with any of the data collection that I have, and I’m a marketer, so, it’s kind of a big deal when somebody on this side says it, is companies are selling our data. There’s big business in big data. I don’t want to do business with somebody who’s doing that. I won’t work for a company that does that, because even though it’s not against the law, it’s not unethical, it’s just not my particular brand of this is how we get ahead.

Joe: Yeah, absolutely. If somebody wants my data to make the thing I’m using better, especially if I’m using it for free. You gotta understand that there’s going to be some trade-off, but if they’re just selling it to third parties, like the product is not worth it for me, like you said.

Cool. We talked a bit about the organic stuff, about getting up and running. Some really good ideas to reach out to like WP Mayor and Tavern. I’ve been told like do guest blog posts, establish yourself as an authority to gain that kind of trust in the field where you want to be, but let’s say I am ready, I know the people I want to target for advertising. What channels do you think are most effective? Am I going to have to spend my life’s savings advertising?

Jen: You can. I don’t recommend it. If you’re already getting traffic to your site, you mentioned retargeting earlier, or installing a Facebook Pixel or Google Pixel. Retargeting can be extremely effective. So go ahead. What it’s going to do is it’s going to track where people are on your site, it’s going to allow you to serve up ads to them when they’re away from your site, and you can drill down and get really, really specific.

You can say, “I only want to show this ad if somebody added it to their cart and then abandoned the cart. I only want to show this ad if they viewed at least these three pages on my site, or if they got three-quarters of the way down this page. Now I’m going to show them an ad somewhere else.” Now that assumes you’re targeting an audience who doesn’t use a lot of ad blockers.

Joe: Sure.

Jen: Otherwise, you’re spending money to not show them things, and that’s not very effective.

Joe: Again, like if you’re targeting developers, it’s pretty fair to assume that developers are using ad blockers, and retargeting might not be as effective on them.

Jen: Right. Now, that said, developers still use social networks. They still use forums and things that, if you can adjust your display network settings that you could try to appear on those sites versus the general ones, it might still be worth it. It might still be something that … The ad blockers and the way Google does their ad programs are always evolving. We’re expecting to see some big shifts coming in the next year, but nobody really knows quite what that’s going to be. For now, though, it can be effective.

I also think doing some paid placement things, like Modern Tribe sponsored a podcast. We wanted to see what kind of results did we get. We had never done one before. We thought, “Hey. Joe’s a great guy, and How I Built It sounds like a good fit. Developers use our plugins, he’s talking to developers. Let’s give it a shot.”

There’s also, you can pay for sponsored posts on sites. You could actually pay for people to do reviews of your plugin. All of those pieces can come together in our different avenues. I wouldn’t go out and buy like a TV spot or a radio ad, necessarily.

One that I don’t hear come up as much, that I think is a smart way to do it, I see people like, “Should I sponsor WordCamp?” You should sponsor WordCamp if you want to get back to the community. If you’re trying to promote a plugin, maybe. It depends. Does your plugin appeal to the majority of the people there? Okay, cool. Are the majority of the people there not using your plugin already? Cool. Now it makes sense.

If your plugin only applies to like 20 people there, you just spent a thousand dollars plus to talk to 10 people. That’s not necessarily the best ROI.

On the other hand, there are meetups all over the place. Do you know how much it costs to buy pizza for 20 people?

Joe: Not a whole lot. 20 bucks. 30 bucks. Depends on where you are, right?

Jen: Yeah. Maybe a hundred bucks, depending on how … Maybe they’re really hungry. I don’t know.

Joe: Yeah, right.

Jen: Offer to go buy pizza. Ask for their feedback. Ask if you can give a demo. Like this is legitimate stuff. This is building relationships, and those people, like that’s how you’re starting to get that word of mouth advertising and, yeah, you paid for it, but you’re also just the cool guy who hooked them up with pizza this month.

Joe: Right. Right. That’s a lesson that I learned in college. If you want people to come to your events, offer free pizza. That’s how you get college kids to go anywhere.

Jen: Oh, yeah. That’s how you get people to move stuff, too, pizza and beer.

Joe: Right. Yeah. Exactly. Exactly. That’s fantastic. You mentioned several dozen things that I want to follow up on. I’m just gonna say right here, we’re like 20 minutes or so in. We are most likely going to go over. So we will have the regular episode, and then we will have the bonus super cool part over on I suspect, I’m not there yet, because this isn’t real time that I’m adding this spot, I suspect the conversation is going to be even more excellent over there.

I do want to get to how did you build your marketing strategy for the Events Calendar? That’s like the title question, but there are a few other things I want to parse out, and we’ll do that in the bonus.

That said, I guess a quick teaser. I want to ask you about the Google Pixel, ’cause I know there’s a Facebook one, and then talk a little bit more about like TV ad spots, the ROI of WordCamps, and things like that.

First, let’s get to the title question, how did you build it? And, in this case, how did you build it is, let’s say the marketing strategy for Modern Tribe that you most want to talk about, whether that’s the Events Calendar or something else.

Jen: Oh. I should’ve anticipated this question a little bit better. The Events Calendar was built because we were scratching our own itch. To be fair, I’ve been with Modern Tribe a little over two years. The Events Calendar has been around for like 10. We built it for a lot of our clients. We realized we were building similar things, and we were like, “Hey! Maybe we should put this together and package it as a plugin.”

Back then, there wasn’t really a marketing plan. Over the years, there hasn’t really been like a focused marketing plan in the sense of like I can go to an agency and ask, “What’s the marketing plan for XYZ brand,” and they’ll say, “Oh. It’s right here.” No, there wasn’t any of that.

We enjoyed a lot of kind of organic growth and organic marketing, and the dot-org repo played a large role in that. Then we have continued to release features that has kept us relevant and have kept people adding it. It’s been great.

We mentioned earlier the reliance on traffic and downloads from the repository, and the inability to get customer contact information from that. Well, we love WordPress and will always probably be in the dot-org repository. What we’re doing right now is more building a marketing plan that allows us to get users from different channels, and that’s not because we want to get away from the repository, it’s because people might not be searching there. When they’re searching there, they may not be searching for the keywords that are actually for things that we solve.

Jen: Since we do sell premium products, it’s also because we can mention those just a little bit like, “Hey, there are these extra extensions available in our dot-org plugin listing,” but we can’t really go into a lot of detail there.

Joe: Right. So, actually, just to be clear here, you’re listed on the repo. You don’t get user information, but you’re also not allowed to actively sell in the description or in forum posts, right? Like if I have a support question, you can’t say, “Hey, check out premium support over at the Modern Tribe,” right?

Jen: If you say, “Hey, you guys haven’t responded in three days. How come I’m not getting faster support?”, we can point you to say that we do a pass once or twice a week and offer light support for bug reports in the repo, but if you’re looking for faster support, we do offer premium support here.

Jen: We can’t just blatantly say, “Oh. Don’t use this support forum. Go use the premium support there.”

Joe: I see. Okay. That totally makes sense. Sorry to interrupt. You were looking at other channels for these reasons that you’re listing.

Jen: Yeah. So we’ve got a pretty extensive resource bace built within the We’ve got a knowledge base, we’ve got themer’s guides, extensions library of snippets you can have, because our support team was like, “Eh, this doesn’t need to be released as another plugin. We can just give you a snippet to install and fix. Go.”

There’s no place for them on the dot-org repository, so people don’t know necessarily when they download the Events Calendar that they have all these resources available to them.

Since we don’t have their contact information, other than that initial installation page when they first install the plugin, we can’t communicate that to them very well. I don’t know about you, but I always skip over that initial page tutorial if there’s a little user guide, pointing to the settings. I just skip, skip, skip. I’m sure I know how to figure this out.

Joe: Right. I just want to create events right now. Like that’s why I’m installing this.

Jen: Right. Exactly. So we want to create other channels to access those users, and also to get people to our site who might need, like I said, some of the premium functionality, and they wouldn’t otherwise find it, because the premium plugins aren’t listed in the repo. So we’re looking at things like I said, targeted landing pages; we are going to be doing a bigger content marketing push in 2018.

Another piece I think people don’t talk about when it comes to marketing is the amount of resources. People say, “Oh, there’s a bunch of stuff you can do for free, and there’s a bunch of stuff you can pay for.” Even when you’re doing paid stuff, if you’re going to spend a thousand bucks on Facebook ads, that’s not a net cost of a thousand dollars. That’s just the ad running cost.

There is, how much time are you spending to create those images? Are you hiring a designer to do that? Are you doing it yourself? Oh, do you know how to configure Facebook? Do you know how to install the Facebook Pixel? Do you know how to create custom audiences? How to create look-alike audiences? How to set up different … ? Like you can see. The list goes on and on and on. That’s just Facebook.

You can do this on LinkedIn, you can do this on Twitter. We’ve talked about the Google Display network. It gets pretty extensive, and the same thing on the free side. Okay, you can write a guest post. How much time do you spend writing content? Again, are you including images? How much time are you spending producing those? If you know what keywords you’re targeting, if you want a keyword target.

Then there’s just interacting with that site admin, or editorial manager who’s going to publish the content. Like they probably want to review it. There’s back and forth. There’s definitely a big time cost that comes with marketing, so you have to factor that in when you’re doing different things.

Right now, for 2017, content marketing wasn’t a big focus for the, because we’re putting a lot of energy towards a new product that we’re launching end of this year, early next. So all of that is happening behind the scenes.

Joe: Yeah, absolutely.

Jen: It’s separate from the Events Calendar and so you’re not seeing that reflected on the We’re also working on building up our marketing team. I’m sure by the time this airs, we’ll have a little bit more in place, but it’s the same thing with resource constraints.

We also, for us, marketing includes keeping our existing customers updated on new things that we’re working on, new things that we’re planning. In the past year, we’ve done things like … We did a big refresh of our community events plugin, so we want people to know, “Hey! We’ve been putting in this work for you. We didn’t forget about you. You don’t just buy it and it’s one-and-done. Like we continuously try to add value to it.”

Same thing. We did our rest API endpoints in the Events Calendar this past year, which was a big deal for people who want to extend it beyond WordPress.

Joe: Right. Right.

Jen: We need to give you that information, communicate it, and do the best job that we can. So juggling that is always a challenge, and it’s always a matter of finite resources at the end of the day.

Joe: I mean, as a one-man band here, that makes total sense to me. With the remaining minutes of the main interview before we get into the bonus round, I want to ask you two questions. One is the question that I end every show with, so we’ll get to that next, but if you are a one-man band with limited resources, could you give me like a top three, top five things that I should try to focus on if I want to sell my plugin?

Jen: Yeah. Talk to a couple of people to figure out if your plugin is purchase worthy, for lack of a better term, and try to figure out what price point they would buy it at yet. I think we all tend to jump to like, “Oh, I think I can sell it for 50,” and it turns out that people are only willing to pay 15, or “I’m just going to list it at 15 and see who buys it,” and people are really willing to pay 75. Don’t make those mistakes. It’s really hard to correct them down the road.

Joe: Right. Yeah. Especially a price increase is, there are tomes written about how hard it is to do that without annoying at least some people.

Jen: Mm-Hmm (affirmative). Make sure you can be found if people are looking for you. Then there’s two more pieces I’ll say are like part of the top things you should do. One is go out and find where people are asking questions, and answer them. Reddit, Facebook groups, like just search in quotes for your question, or variations of your question, and you will find like, literally, here’s where somebody asked it.

Be the person that answers. You don’t necessarily have to link back to your stuff, but if you keep appearing in these conversations, you’re going to gain some awareness as like, “Hey, that’s the guy to ask about this,” or the gal, in that case.

The other one is to let your friends and family and whomever know what you’re doing. To this day, my mom will say, “I don’t know what Jen does. She sits in front of a computer, and she doesn’t come visit me enough.” She can’t recommend me. Who knows who she might run into in her life that needs marketing strategy. She can’t recommend me, because she can’t say it.

If people around you don’t know what you’re doing, don’t know what this cool project is, they can’t recommend you to others, they can’t give you recommendations on how to connect with people. I think that’s like really, really baseline must do.

Joe: That’s fantastic. I’ve wondered if I’ve been like oversharing my work stuff too much on Facebook, but that definitely lets my friends and family know exactly what I’m doing and what I’m trying to hawk that week. That’s really great advice.

Before we get to the extended stuff, I’m going to ask you, do you have any trade secrets for us?

Jen: I don’t like to give them away.

Joe: Understandable.

Jen: Yes. I do. This is probably the biggest trade secret, that people are willing to give away free advice. Like if you tell me, “Hey, Jen. I’m stuck on this. Can I take you out to lunch and maybe get your advice on it?” I’ll say, “Sure. This week is busy. Why don’t we look two weeks out? Let’s put something on the calendar.”

If somebody asks me for a call, I do the same thing. I do virtual coffees with people all the time, and I’m not the only one. I even ask people, “Hey! I’m stuck on this. Can we meet, and would you mind giving me a couple tips?” The key there is to be really specific about what you’re looking for, and not just come out and ask somebody to do it for you.

Joe: Right.

Jen: I’ve had those people contact me, as well, and then I’m like, “Well, I’m really busy. I don’t think I can fit that in.”

Jen: If you’re just looking for a few things and you’re genuinely connecting, awesome. We’ve all been at that starting point. Find people who can give you the stepping stones to get you where you want to be.

Outro: Thanks again to Jen for joining me. Much like with Nicole last week, I was able to change up some of what I was doing thanks to Jen’s advice. While unfortunately we couldn’t connect for the second part of the interview, I think this episode is packed full of great, actionable stuff.

And Thanks again to our sponsors – make sure to check out Liquid Web for managed WordPress hosting. I use them on all of my important sites – they are that good! They are at They’ll give you 50% off your first 2 months just for being a listener! If you want to save your clients (or yourself) money through recovering abandoned carts, check out jilt. They are over at And finally, if you want to put a cherry on top of the e-commerce trifecta, there’s Checkout for WooCommerce. If Jilt brings back the people who leave, Checkout for WooCommerce is the tool that prevents people from leaving in the first place. I use it, and I love it. And you can get 10% off using the code BUILD at

For all of the show notes, head over to If you like the show, head over to Apple Podcasts and leaving us a rating and review. It helps people discover us! Finally, last week I published my brand-new Patreon page. It offers a lot better rewards, and great goals, and I’m really doubling down on it. So if you like the show and what to support it directly, head over to You can support the show for as little as $1/month.

Next Week, we’ll close out this series talking to my good friend Brad Williams about client relationships. Brad works with some big companies over at WebDevStudios, so he knows a thing or two. Make sure to tune in! And until next week, get out there and build something.

The post Jen Jamar and Marketing appeared first on How I Built It.

Mar 27 2018



Rank #6: Sherry Walling & Choosing Self Employment

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This is Part 1 of our mini series, “How You Build a Business”

In today’s episode, I get to talk to Dr. Sherry Walling. She’s kicking off our miniseries on how to build a business and she helps us answer a very important question: “Am I ready to start my own business?” Sherry is a fantastic person to talk to and a wealth of knowledge. We talk self-publishing, self-knowledge, podcasting, and much more.

Show Notes

Check out our Patreon!

Sponsored by:
  • Beaver Builder: A drag and drop page builder and a platform you can trust with your business. They do page building the WordPress way.
  • Jilt: The easiest way to recover abandoned shopping carts on WooCommerce, easy digital downloads, and Shopify.
  • Liquid Web: Fast, Managed WordPress hosting whether your users are logged in or logged out. Get 50% off the first 2 months.
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Intro: Hey everybody and welcome to another episode of How I Built It! In today’s episode, I get to talk to Dr. Sherry Walling. She’s kicking off our miniseries on how to build a business and she helps us answer a very important question: “Am I ready to start my own business?” Sherry is a fantastic person to talk to and a wealth of knowledge. We talk self-publishing, self-knowledge, podcasting, and much more. This is a great episode that we’re going to get into. But first, a word from our sponsors.

Sponsors: This season of How I Built It is brought to you by two fantastic sponsors. The first is Liquid Web. If you’re running a membership site, an online course, or even a real estate site on word press, you’ve likely already discovered many hosts that have optimized their platforms for a logged out experience, where they cash everything. Sites on their hardware are great for your sales and landing pages, but struggle when your users start logging in. At that point, your site is as slow as if you were on three dollar hosting. Liquid Web built their managed word press platform optimized for sites that want speed and performance, regardless of whether a customer is logged in or logged out. Trust me on this, I’ve tried it out and it’s fast, seriously fast. Now, with their single site plan, Liquid Web is a no-brainer for anyone whose site is actually part of their business, and not just a site promoting their business. Check out the rest of the features on their platform by visiting them at web. That’s web.

It’s also brought to you by Jilt. Jilt is the easiest way to recover abandoned shopping carts on woo commerce, easy digital downloads and Shopify. Your e-commerce clients could be leaving literally thousands of dollars on the table and here’s why. 70% of all shopping carts are abandoned prior to checkout. Yes, you heard that right, 70% of shoppers never make it to checkout. That’s why you need to introduce your clients to Jilt. Jilt uses proven recovery tactics to rescue that lost revenue. It’s an easy win that let’s you boost your clients revenue by as much as 15% and it only takes 15 minutes of your time to set up. Jilt fully integrates with woo commerce, EDD and Shopify. You can completely customize the recovery emails that Jilt sends, to match your clients branding using it’s powerful dragon drop editor. Or by digging into the HTML and CSS. Even better, Jilt’s fair pricing means your clients pay only for the customers they actually engage. You get to earn a cut of that through Jilt’s partner program. Whether you have clients that process one sale per month or 10,000 sales per month, be the hero and help them supercharge their revenue with Jilt. Check them out at That’s

And now…on with the show!

Joe: Hey, everybody, welcome to another episode of How I Built It, the podcast that asks how did you build that? Today my guest is Dr. Sherry Walling. Dr. Sherry, how are you today?

Sherry: I’m good. It’s a mouthful.

Joe: I know. I was like totally on autopilot, so it was like the first thing you say is the first name, so just say that. How are you doing today?

Sherry: I’m doing well. It’s like 30 degrees in Minneapolis, which is like summer vacation weather for us in the middle of winter. It’s been like negative 10, so 30 is like amazing.

Joe: Yeah. Being from the Northeast, I thought I had it pretty bad at like negative one, and then I look at what you guys are going through, so I was grateful to have one 60-degree day last week. I’m like it’s 65 degrees warmer than it’s been. It builds character, I think.

You are going to be talking to us today about mental health, in general, but you have a book coming out. I’m going to bleep the bad word, because I don’t want to throw the explicit warning on this. It’s Keeping Your Beep Together.

Sherry: The Entrepreneur’s Guide to Keeping Your Beep Together: How to run your business without letting it run you.

Joe: There you go. That’s the full name. I really wish I had that up and I had something else up on my other screen. I was kind of perusing the book before this interview, and there’s a lot of great stuff in there. Why don’t we start with who you are and what you do?

Sherry: I’m a clinical psychologist. I have a PhD in clinical psychology. I have traditionally done a lot of work with people who have really high intensity jobs, so I did a lot of my training with folks in the military, and then since built a practice working largely with physicians, attorneys, people who just have sort of high pressure, high stress work.

In the last couple of years, I’ve been doing a podcast with my husband Rob Walling, who’s a serial tech founder. He started a company called HitTail, a company called Drip, and a conference called MicroConf, so he’s like a techie guy.

A couple of years ago, three years ago, actually, we started a podcast together called Zen Founder, where we talk about the mental side, the family side of being an entrepreneur and try to share some good information that’s informed by science as well as our experience to help people’s lives be a little bit easier in the midst of starting and running a business.

Joe: Man, that’s fantastic. I’m so excited to have you on the show, because it’s unlike any guest I’ve really had. I usually talk to developers or entrepreneurs about the things that they’ve created, but mental health, I feel, is something that is being discussed a little bit more but still isn’t given the kind of center stage thought that it should.

I’m definitely going to link your podcast in the show notes. It’s a great show, and you guys cover a lot of … You guys get pretty personal on the show, too, right? It’s probably not easy doing a show like that.

Sherry: You know, it’s interesting. We started out not very personal. We started out a lot of 10 points to beat procrastination, kind of thing. The last year, really the last year-and-a-half, we’ve been through some really significant things in our family including the acquisition of Rob’s company that led us to the move from California to Minneapolis.

Some of the things that we went through as a family, I think, were just super relevant to the people that listen to this show. Then last January, my dad was diagnosed with cancer, so that became a thing that also shaped our lives, but had some impact on our businesses.

We didn’t set out to do a podcast that was about us, but I work with founders, I’m a consultant with founders, I’m a therapist for founders, so I know that those kinds of experiences in your family life definitely have an impact on your business. It just sort of made sense and was authentic for us to begin talking a little bit more about our family life and personal life in the context of what it meant for us as we both run businesses.

Joe: Yeah. Absolutely. You also, kind of in that same vein, you mentioned that you are a clinical psychologist for high stress work, right? I feel like, and, again, this is like all kind of stuff that is from personal experience, but I’ve gotten, you know, “You don’t have a real job. You work for yourself,” or “You’re a freelancer,” and stuff like that.

A lot of people who aren’t in it, kind of view self-employment or freelancing, especially, freelancing has the negative connotation as like easy. They don’t view it as high stress.

Sherry: Yeah. I feel like maybe those folks don’t know what it’s like to be responsible for your own paycheck.

Joe: Right. Especially like if you have kids. I just went full time self-employed in June. I had a three-month-old at home. I don’t know what I was thinking, but it’s working out so far, but it can get very stressful.

Sherry: Yeah. I think there are some really unique stresses that go along with being a freelance or being an entrepreneur, in that you do assume responsibility for the direction of your entire life. That includes the financial responsibility as well as all of the decisions weigh on you.

Again, lots of us have high intensity jobs and stressful jobs, but I think there’s something unique about the entrepreneurial life because it is such a solo enterprise, and you bear all of the weight on your own. Even if you have a spouse that’s all in, and even sometimes if you have a business partner, it’s a uniquely lonely enterprise, which I think from a mental health perspective, has some pretty significant challenges.

Joe: Yeah. Absolutely. You mentioned that before you did this, you were doing military. Is that right?

Sherry: Yeah. I worked in several different VA hospitals in Los Angeles and in Boston.

Joe: Got you. What was the transition like? Did you find it was completely different contexts? Or were there shockingly similar contexts between the two?

Sherry: I think that there are some similarities in the sense that a lot of people who’ve been in combat learn to operate at a level of elevation or a level of stress that feels normal to them, it becomes normal to them.

Seeing a very similar pattern in entrepreneurs who’ve maybe gone through the intensity of a big launch, if they’re in software, for example, and learn to operate at this level of stress, this level of go, go, go, go, go, go, go, and they forget what civilian life is like, or similar to people who are returning from combat, it feels sort of strange to be in civilian life after adjusting to the intensity of a combat zone.

It’s obviously not a perfect parallel, but there are certainly some parallels in the intensity, constant drive, constant rush, constant push that entrepreneurs can find themselves in without kind of this memory of how to live in a more relaxed sustainable way.

Joe: Yeah. Absolutely. Just to add a personal point onto that: I’ve been kind of self-employed in some way, shape, or form since high school. I’ve been full time, I’ve been moonlighting, and one of the big adjustments, and I’m still having trouble with this, is when I’m watching my daughter, like my wife is a night shift nurse, when I’m watching my daughter, I have a hard time not waiting for her to take a nap so I can go do some work, or when I have some downtime, do some work instead of watch TV.

It’s always, when am I going to have time to do that next thing that’s on my plate? Do all parents go through this? Probably not. A lot probably have like a nine-to-five, and they’re very good at separating their work life from their home life, but that’s a transition for me, and I don’t feel like I’m super high stress in my work, but that’s a transition that’s been kind of hard for me, so I can totally see what you’re saying and where you kind of went with the analogy.

Sherry: It’s a sense of being never off.

Joe: Right. Yeah. Exactly. Which could be very stressful. So you have this book that’s kind of the entrepreneur’s guide to making sure you are ready to be an entrepreneur. Again, I have the book in front of me. I was looking at the table of contents. The chapter that jumped out at me the most was chapter three, Self-Knowledge. Because one of the things that I’ll recommend to people who are saying I’m thinking about doing it, is you need to ask, are you ready? Have you thought about this? Is this even something that you want?

A lot of people say working for yourself is a coveted thing, but it’s not for everybody. We can kind of frame all of the questions around that chapter, but branch out as you’d like. First of all, what gave you the idea for the book?

Sherry: We’ve had the podcast. We just recorded episode 151. So there’s a lot of content that Rob and I have been talking about over the years, and that I’ve been talking about at conference presentations and things like that. We wanted to really create something where it was just easy and accessible, where people could get sort of like the take-home bullet points in a fast digestible way where they didn’t have to listen to a hundred and fifty hours of podcasts although, hey, we’re very entertaining.

It also, I think, is a way of just getting that information out there in a way that’s easily accessible. Then I also wanted to really expand, I think, the reach beyond folks who are dedicated podcast listeners. I think podcasting is an amazing medium. It’s been something that I have really enjoyed doing over the last few years, but certainly there’s a larger group of people who are going to pick up a book than will sit and listen to a podcast.

Joe: Nice. Absolutely. When you set out to do the book, did you get advice from anybody? Do you know a lot of published authors who gave you advice? Did you go through the proposal process of finding a publisher? Are you self-publishing? What was kind of the legwork before you set out to actually write the book?

Sherry: Thankfully, I know quite a few authors so was able to talk with them and kind of review the pros and cons of publishing in different ways. I also have a previous life as an academic. I was tenure-track faculty for three years, so a lot of my world has revolved around writing and publishing, mostly in academic journals, which is very different than what this book is, thankfully. It’s a little bit more entertaining.

We decided, and Rob is second author on the book, so we decided that we would self-publish primarily because it allowed us to retain a lot of control and some focus on building our audience, so that was a decision that we made really thinking about what the intention for the book was.

Joe: Got you. That makes sense. Well, first of all, getting published in an academic journal, I know, is not easy or exciting, because I did it in grad school. It’s like I can’t even go back and read this paper that I helped write because it’s so dry. It’s just like very, here are the facts.

Sherry: I would spend like 9 to 12 months writing a paper, especially after you conduct the research, you’ve run your stats, you do the whole process, and I would spend all of this time writing a paper, and maybe like 50 people would read it. I got published in some reasonable journals that have pretty good reach, but then I get on the podcast and after working at it for several years, thousands of people, for better or worse, listen to Rob and I talk every week.

So the reach and the impact in the community is so much greater, which is why I’m really grateful to have the medium, and hopefully now publish the book in a way that will have bigger reach than the 50 people who read my analysis of, I don’t know, combat-related PTSD.

Joe: Yeah. Absolutely. I will say that my paper, which was on, I think the title was Automated Congestion Detection Using Mobile GPS … It’s like traffic detection using phones. I know it was published like in 2008, before it was a thing that happened. I think one person cited my paper in their paper, and it was like I had a party about it. I’m like, “Yes!” Self-publishing is great.

I’ve also gone through the publishing process with a publisher, so that’s a very different thing, too. It’s like you have the proposal and a lot of back-and-forth, but for audience building, especially, I did that because the publisher had audience and was interested in the topic. You get some money up front, but I don’t know how much my audience grew because of it.

As far as self-publishing goes, before we really get into the topic, do you have like a game plan for it as far as, are you going to do print-on-demand? It is only going to be a PDF or an e-book, and things like that?

Sherry: Well, we’re doing a printed book, an audiobook, and the e-book. We’ve gone through Amazon’s CreateSpace, which is the most archaic piece of software that I’ve used since DOS-based e-mail in college. Sorry, Amazon, but your CreateSpace sucks.

Joe: Plus one on that.

Sherry: Yeah. I’m really, really, this is the best we have? Yeah, so we have the printed version, which I am looking at a proof right now. If feels good in my hands, I’ve gotta say. Then we’ll have the e-book. Then I recorded the audiobook, which I think for the podcast listeners who are used to listening to my voice, that will feel familiar and hoping that it’s not irritating to everyone who’s not used to listening to my voice.

Joe: Was it different narrating the book as opposed to actually doing the podcast? Do you have a more formal cadence to the audiobook? Or is it still that casual conversation? Just out of curiosity.

Sherry: I really worked hard for it to sound more casual, because I think audiobooks, especially when they are read by the author, if they’re read in a way that feels really rote and detached, I think something is really lost. There’s definitely some parts in the audiobook where I just sort of go on a tangent and riff a little bit, and I’m like, “Okay, audiobook listeners … ”

I’ve really wanted it to be more conversational. Again, we’ll see if that feels good to the listener once we get some feedback and reviews about it. I will tell you that I recorded the audiobook before we finalized the printed version of the book, and that was super valuable, because, of course, I’ve read it over and over, I wrote it, I’ve edited it, I’ve spent a lot of time with this material, but reading it out loud, there were just things that, “Oh, that came out funny,” or “That’s not what I meant,” so it was a really nice final process of editing the book, actually, to read it out loud, record the audiobook, and then go back and actually make some changes to the printed text, where it just didn’t sound right as I read it out loud.

Joe: I think that’s really great advice for any kind of long form writing, especially. Some advice I got from an English teacher in school was like, “Read it out loud and see how it sounds.” I did that with a newsletter I got, where somebody said, “This app has become my wife and I’s favorite,” and I’m like you did not read this out loud, because that’s not grammatically correct, and it sounds super weird. Like my wife and I’s? I think that’s great advice in general, because you really do get to see, or hear, how it sounds to the reader. That’s fantastic. Then another bonus of self-publishing is, you mentioned you’re going to get feedback from readers, listeners; you can iterate more quickly on a self-published book, right?

Sherry: Absolutely. I mean, I own the audio files. If people are like, “What happened to you in chapter five?”, I can go back and fix that. Or I can go back and make modifications that I feel like need to be made once the products have had some life to them.

Joe: Right. Right. On that same token, I’m very grateful for my publisher, but my book is three, almost four years old, at this point. If I want to make updates to it, they don’t want to do a version two, so now I have to go through getting the rights back so I can update and distribute it if I want to.

I’m very grateful for my publisher, and it’s Peachpit, and I learned how to make websites from Peachpit, so I’m honored that they published my book, but a few years down the line, especially with tech books, it’s out of date. Now this is another hurdle I have to go through if I want to put out the book again. Oh, yeah. Go ahead.

Sherry: I was going to say, I think if there’s a second or third book in my future, I would definitely consider going through a publisher just to have that experience. I also do swim in the academic circles still a little bit, and there is still a cache to being published by a publisher and having gone through that review process.

I don’t diminish that process at all. I think it’s really important, but I think for this one, we wanted to get this out to our scrappy podcast audience. So it feels good to have self-published this one and, again, I would totally consider going through a publisher the next round.

Joe: Totally. It comes down to like what you’ve been saying, it all depends on what you want. I will say having that book officially published is what helped, I feel, that helped me land my job at Crowd Favorite, or at least Karim, the CEO of Crowd Favorite and a good friend and my former boss, was very happy that I was able to publish that book, because it was something that we could tell clients.

There is a cache to being published, and it really all depends on what your goal is. If you’re going to iterate quickly, self-publishing is definitely the way to go.

We’re like 20 minutes into this conversation. Let’s talk about the subject matter. I’ll say, like, Sherry, you’re very easy to talk to, which is probably a great quality to have in a clinical psychologist, so this is why we’re 20 minutes in and we haven’t even talked about the book. So this is going to be a longer-than-normal episode.

Sherry: Soon I’m going to get you talking about your mother.

Joe: I know. I know. I’m an Italian, so I’m very attached to my mother, of course. Let’s talk about chapter three, Self Knowledge. Maybe you can give us like a quick overview of what that chapter covers and kind of your goal for writing that chapter. Does that sound good?

Sherry: Yeah. So really my goal was not to help people assess whether or not they’re ready to be an entrepreneur. I think my goal is generally to assume that lots of different kinds of people can be successful as an entrepreneur, especially if you have like a really clear sense of what your strengths and weaknesses are and know how to plan around them.

In this chapter, we talk about a couple of different continuums. One is introversion/extroversion, which lots of us talk about all the time. One that we talked about is growth mindset versus fixed mindset. The last one that we talk about is chaos versus rigidity.

We think about these continuums as different ways of kind of organizing a personality, and no matter if you are an introvert or an extrovert, or you tend toward the more rigid, or you tend toward the more chaotic, there’s a place for you in the entrepreneurial world, but being able to tell the truth about what you’re good at and what your liabilities are is really the point of self-knowledge.

Joe: I mean, that’s a huge step in being successful, like being a successful entrepreneur, like knowing … Like I know, for example, that I would like to be more rigid than I am, but I have like 14 notebooks on my desk right now with different notes in each of them. As long as I understand that that’s the way I work and at some point during my day I organize all of those into a single list or a group of notes, that’ll help me stay on track. I’ll focus less on I need to be more rigid and more on focusing on the core of my business. Is that accurate?

Sherry: Absolutely. I think those of us who tend to be more flexible and more kind of big-picture thinking, more outside the box, those are great entrepreneurial skills, but it does mean we probably need to support our business with either the help of a Type A person who can come in and sort of keep us going in the right direction at the right time, or there’s certainly software that can help supplement, too.

I know just in working with you in organizing the podcast, you use Calendly, you have notes that are set up, so you have this system that’s in place that helps you provide structure to people who come on your podcast as guests, so you don’t bear the burden of like remembering, “Oh, I need to tell Sherry that we record this way,” and “I need to do this,” and “I need to do that.”

As an out-of-the-box sort of more chaotic person, you’re not going to be good at those things, so you can create systems that do them for you.

Joe: Right. Right. That came about because my first few guests, I’m like, “Oh, yeah, I forgot to tell you this,” and I’m like I should stop forgetting to tell my guests things.

Moving to the personality stuff, I know a lot of … At least a lot of people in the WordPress space, which is where the core of my audience is, are introverts, either self-identified or otherwise. I am super duper extroverted. What kind of effects does that have on a business? What should somebody think about if they’re introverted versus extroverted?

Sherry: For people who tend to be extroverts, it’s such a great super power, especially as you’re in sales or marketing or just letting people know about what you’re passionate about and what you’re doing in your business, but it can provide sometimes some blind spots, particularly in listening and observing.

If you want to be an extrovert, or if you are an extrovert, rather, like you don’t struggle to fill space. You don’t struggle to facilitate or host a conversation, but it might be a little bit harder for you to listen well. Listening, of course, is super important in a business. You’ve gotta listen to your clients, you’ve gotta listen to feedback from people that work for you and with you.

If you are often the center stage person, it’s really helpful to be super intentional about getting feedback and really listening to that feedback well. I also think it can be easy to kind of neglect your inner life if you’re an extrovert. It’s not that extroverts aren’t deep people, they certainly can be, and they certainly are, but to really take time to think about like, how am I doing? What’s going well in my life? What’s my emotional life like these days? That self-reflection, internalization, can be a little bit more challenging for extroverts, but it’s still really important for them.

Joe: Got you. Well, I was nodding my head a lot during that, so I’m definitely relating to what you’re saying. As far as introverts go, first of all, I’ll say this: People often equate introversion with antisocial, but that’s not really the case, right?

Sherry: Psychologically speaking, those are super super different things. Antisocial is like, antisocial personality disorder, which is essentially someone who lacks the neurological capacity for empathy. Like they tend to be highly represented in the clinical, or like in the prison population. Don’t use antisocial when you mean not very socially oriented, because antisocial is a very different thing.

Joe: Got you. Awesome. I’m really glad you clarified that. I meant it more colloquially as in people tend to shy away from social events. Even that’s not necessarily the case for introverts. Introverts, I’m friends with many, whom I’ve met at conferences.

Sherry: Yeah. I was at this speakers dinner for Converted, which is, Lee Page hosted this Converted Conference, which is like heavy marketers. Ezra Firestone was there. Anyway, Derek Hepburn was there, Rob was the speaker, really like gregarious, on-stage people who you would think would be like the extroverted extroverts. As we went around the table and talked about this, like the vast majority of them identified as introverts.

Being an introvert has really nothing to do with how well you can hold a conversation or how well you can present on stage. Being an introvert has to do with how you restore your level of energy, and usually that’s sort of the way of recharging your personal batteries happens by yourself. Your inner world is important. The quality of what happens inside of you is of great interest and importance to you if you’re an introvert.

Joe: Got you. That makes sense. My wife, who is an introvert, and I differ in that way. She values her alone time. I told her the last time I went to WordCamp US I walked in, there were like 2000 people. I knew many of them. I was totally energized by that experience.

Sherry: Kid in a candy store.

Joe: Yeah, exactly. That’s fantastic. What other highlights from this chapter would you like to mention here? Again, we’re just kind of getting a taste of one chapter of a book, and I’m already really excited to read the rest of it, because I love everything you’re saying right now.

Sherry: I think the take home in this chapter is like … is really no matter how you’re built as a person, there are some super powers intrinsic in that. If you’re a really introverted person, you have some amazing skills in your ability to observe and read situations, because you’re not busy talking; you’re often busy watching. Understanding what super powers you have based on just who you are in the world is really great in terms of identifying and cultivating your own strengths.

Then we also want to tell the truth about the shadow side, or the liabilities that go along with being an introvert, for example, and the things that you might have to intentionally either make yourself do, or hire out, or plan around so that they don’t become weaknesses that damage your business.

Self-knowledge is just about self-reflection. What am I good at? What am I not good at? And really being honest with yourself, which is not always easy to do. I think some of us are just naturally pretty barricaded against that kind of honest self-assessment.

Joe: Yeah. Absolutely. That’s fantastic. I know we’re kind of coming up on time already, but there’s more I’d like to talk about. What’s your favorite part of the book, would you say?

Sherry: Oh, that’s like choosing a favorite child.

Joe: I know. This is like out of left field, too. I sent show notes, and I didn’t prep you for this question.

Sherry: No, that’s okay. There’s a chapter that is kind of a deep dive into mental health where we talk about depression. The chapter’s called Coming Undone. I feel pretty proud of that, because I do feel like it’s a unique voice that I offer to the entrepreneurial world that many other people can’t offer with the same quality and depth as somebody who’s spent years and years and years training as a psychologist.

I don’t know. I feel like lame saying this, but I’m proud of this book. There’s a lot of me in here, so I’m already sort of bolstering myself from the negative feedback that I know will come. That’s part of putting something out there in the world. Not everyone’s going to love it, and that’s okay, but this represents some hard work that I want to offer to the community, and I hope it’s helpful.

Joe: Absolutely. Maybe we can parcel that out a little bit. Before we started recording, I told you about an experience I had on the day of this recording, which was not based on any of my work at all. It was about a pretty strong opinion about sports fans from a particular area and all of the negativity I got from that, and that wasn’t even something that I was deeply attached to, but I felt it, because it came pretty hard.

So what advice do you have for somebody who’s totally putting themselves out there? If you work for somebody, you’re probably doing somebody else’s work, and while you might enjoy the work you’re doing, I’m not saying you don’t enjoy that work, but as an entrepreneur, it’s all you. It’s your idea, it’s your execution. How do you bolster yourself from the inevitable negative feedback that will come at you?

Sherry: I think we have to choose our spheres of deep feedback. Rob has read the book. He wrote it with me. If he has feedback, I’m going to listen. There are circle of friends, there’s a circle of other entrepreneurs who I share my ideas with, and whatever feedback they have say, positive or negative, I really listen.

Then there’s, like my Twitter followers, or people I’m with on Facebook, or people who have done consulting with me, and their perspective matters to me, but it’s at this other level on the concentric circles of my selfhood. They don’t get to have this direct route to my heart. I’m going to filter a little bit more.

So we have to kind of choose how much we let people in and be willing to dismiss feedback, or at least give it less weight from certain people.

I think the other thing that I am just talking to myself a lot about is that I did my best to provide something valuable. Again, not everyone’s going to like it, but I did my best to provide something valuable, so I’m just going to say that over and over to myself, especially when I’m confronted with negative feedback.

There are certainly things that could be better about the book, and I hope my next book is better. I hope my podcast continues to get better. I’m oriented towards growing, but I’m not going to spend a lot of time thinking about feedback that doesn’t help me grow.

Joe: I think that’s great advice, and kind of based on what you’re saying there, something that I told myself this morning as I’m reading all of these mean tweets is that tweet is a blip on that person’s radar. They’re going to make that comment and then move on with their life, and I should do the same. I should read it and move on.

If I think it’s going to be helpful to me, then I will take it, but kind of taking all of these five seconds or less that these people took to write the tweet to heart and really carry it with me, is not healthy and not helpful, either.

Sherry: Yeah. Your response shouldn’t be greater than the energy that was put into the feedback.

Joe: Man, I love that. That’s probably going to be the quote that I use to promote this episode.

Sherry: Quotable.

Joe: Awesome. As we come up to the end here, I want to ask … We talked a lot about the content of the book and the book writing process. Let’s look at post launch. What are your plans for the future of this book, of followup books, things like that? What are you going to do after the book comes out?

Sherry: After the book comes out, I hope I get the opportunity to talk about it a lot and share it with people. I’m trying to leave space in my life and world for some conference speaking and being on podcasts and hopefully talking about the book as much as people will be willing to listen.

Rob and I are also hatching a plan for a course that we’re going to do, a video course, that’s going to be related to family life, particularly how to keep peace with your significant other while you’re launching a business.

I’m working on writing the content for that right now and we’ll be recording in early February. I think we are wanting to work together to provide some things that are more accessible to people than, again, like hours of podcast content or coming to a conference or something like that.

Joe: That’s great. The course that you mentioned, is that based on … I know you’re doing these events called ZenTribes. I didn’t have this written down, but I’m ad libbing a little bit. One was specifically about being an entrepreneur and being the spouse of an entrepreneur, is that right?

Sherry: Right. We did a couples retreat in September with a group of folks where we really did a deep dive into how do you keep your relationship healthy under the stress of being an entrepreneur, which I think was one of the things that I found most valuable and am most proud of in terms of last year what I worked on.

Then we put together a ZenTribe for families that we call Founder Families, but to be honest, we never launched it, because we could never find a time when we could get people and their significant others together in a group. We were looking at evening times. People are busy, so that’s why the course seemed like a better way to do that. It’s kind of a do-it-yourself-at-home kind of course.

Joe: Got you. I know the last kind of one that you announced was bad timing for me. I had considered it, though, because the things that you talk about, the kind of camaraderie that you have with the other people in these groups is super valuable. Plus I know that you’re heavily involved with the Heskeths, and they’re like the parents that I want to grow up to be.

Sherry: They’re amazing.

Joe: I’ve told them that before, so they’re not hearing this for the first time. That sounds fantastic. For the last question, I know you gave us a lot of great advice, but do you have any trade secrets for us?

Sherry: I think the trade secret that I’ve been thinking about a lot for mental health is to play long ball, to really not get tangled in the day-to-day ups and downs, but to play long ball with your business and long ball with your life.

Joe: I like that. Have a bad day here, have a good day there, but over the long term … It’s like investing in stocks. You don’t want to live and die by a single day of trading. Cool. Very cool.

Well, Dr. Walling, thank you so much for your time today. I really appreciate it. Where can people find you?

Sherry: I’m at All the things that we are scheming and dreaming are there, and we love hearing from people who are thinking about mental health, so people can absolutely find us there. I’m via email.

Joe: Awesome. I will link all of that in the show notes for this episode, which you can find over at Sherry, thank you so much for your time. Thanks to everybody out there listening. Until next time, get out there and build something.

Outro: What a great conversation – thanks again to Sherry for joining me and for kicking off this series. Definitely check out here book. It’s in the show notes and it’s $3.99 on the Kindle.

And Thanks again to our sponsors – make sure to check out Liquid Web for managed WordPress hosting. I use them on all of my important sites – they are that good! They are at They’ll give you 50% off your first 2 months just for being a listener! If you want to save your clients (or yourself) money through recovering abandoned carts, check out jilt. They are over at And finally, if you want to build incredible websites at a fraction of the time and cost, check out Beaver Builder. I use it and I love it. They are over at

For all of the show notes, head over to If you like the show, head over to Apple Podcasts and leaving us a rating and review. It helps people discover us! Finally, last week I published my brand-new Patreon page. It offers a lot better rewards, and great goals, and I’m really doubling down on it. So if you like the show and what to support it directly, head over to You can support the show for as little as $1/month.

Continuing our series next week, I’m talking to Sara Dunn about niching down. She’s been very transparent about her process and I’m so excited to get her on the show to talk about the decision making process. Hopefully it will help you too.

The post Sherry Walling & Choosing Self Employment appeared first on How I Built It.

Feb 27 2018



Rank #7: Myke Hurley and Relay FM

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Myke Hurley is a well-known podcaster and founder of Relay FM. To kick off Season 6, he gives us some fantastic advice on starting shows, sponsors, and lots more. His story is incredibly interesting and I think it’s a great way to start this season and the new year.

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Intro: Hey, everybody. Welcome to season six of How I Built It. In episode 106, kicking off the year and this season is a person I’m a huge fan of, and that’s Myke Hurley from Relay FM. If you follow my blog, you’ll know that for the last two years my favorite podcast have been podcasts where he is a co-host, and indeed most of my favorite podcasts are podcasts from In this episode, he’s going to talk about starting a podcast network and podcasting in general. He gives us lots of great advice on how to figure out how to determine your podcast format and your topic, what your interests are and things like that. As a little bit of a bonus, I wasn’t going to ask him about this because it seems subjective, but he gives us fantastic advice on how to get sponsors for your podcast. He is someone that you should definitely listen to on this because that is primarily how Relay FM is supported. Without further ado, I’d love to introduce you to Myke Hurley. This is a great episode to kick off the year. But first, a word from our sponsors.

Break: This season is brought to you by Plesk. Do you spend too much time doing server admin work, and not enough time building websites? Plesk helps you manage servers, websites, and customers in one dashboard. Helping you do those tasks up to 10 times faster than manually coding everything. As someone who just spent a bunch of time finding the right tools and automations to save myself time, I can tell you that Plesk is invaluable. You can try Plesk for free today at This episode is also brought to you by our friends at Castos. Castos is a podcast hosting platform built specifically for WordPress. They’re a Seriously Simple Podcasting plugin that lets you manage all of your episodes and podcast RSS feeds from your WordPress site, but have your files hosted on a dedicated media hosting platform. I love how the Castos team takes a common sense approach to their pricing, too. You can create as many episodes and podcasts as you want. You don’t have to worry about how much storage you’re using or silly bandwidth restrictions. If you’re like me and already have a ton of episodes from an old host, they’ve got you covered there, too. Castos will import all of your podcast content into their platform completely free of charge. It is just one click of a button. The Castos team has put together a special opportunity for listeners of this show. They’re giving away their most popular package, the YouTube republishing tier where they automatically convert your audio files into a video format and publish them to YouTube completely free, for one listener. For a chance to win tweet at me @jcasabona, and [@castoshq], and tell us why you think you should win this free year of Castos hosting. On February 1st, 2019 they’ll pick one winner to get this $340 package completely for free. Thanks so much to the Castos team for sponsoring today’s episode.

Joe Casabona: Myke Hurley, founder of Relay FM. Myke, how are you today?

Myke Hurley: I’m very well, thank you for having me.

Joe: Thanks for coming on the show. I am a big fan of your work. I would say 50% of the podcasts I listen to are Relay FM podcasts, and I’m excited to talk about podcasting in general, and how you built this podcast network.

Myke: Thank you very much for subscribing to the shows, I appreciate it.

Joe: For all of you listening, if you haven’t heard anything from Relay FM, there’s a lot there for people if you’re into– Like Automation is a newer show that I’ve been a big fan of. Let’s start at the beginning, why don’t you tell people who you are and what you do?

Myke: I have two main jobs. The one that most people will see is that I am a podcast host, and I host many shows mostly around technology. But also creativity is another general theme, and video gaming, and stuff like that. They’re the three main areas that are the types of shows that I make. I make a show for everything that I care about, which is– That’s the podcaster’s problem. When you’ve been podcasting for close to ten years like I have, you end up amassing many shows based upon all the various things that you’re interested in. The other part of my job, which over time is becoming increasingly more time demanding, is running my company. I’m the co-founder of Relay FM, the podcast network of which my shows are a part of. My daily roles go between tackling issues that the people that we work with need sorted, and also the main part of my role is managing the advertising sales for the shows on our network.

Joe: You wear a bunch of hats. I like your podcaster’s dilemma, and I’m starting to feel the same way. I have this show about people building their products, and then I have another show that’s toolkits for web development. But I’ve thought, “Maybe I should start a podcast about–” Whatever other general interests I have.

Myke: It’s funny– It will get you.

Joe: I’m in a mastermind group, and my friends are like, “You need to do fewer things.” So I’m trying to keep that in mind. One of the shows you do host is The Pen Addict, and I’ve had Brad on this show before so I’ll link that in the show notes. [He was] talking about how he built Nock Co. But I want to ask you, and you said you’ve been doing this for ten years. What was your first podcast?

Myke: My first show was mostly focused– It was me and a friend, Terry. We had conversations on the phone quite frequently about the things that we were interested in. Apple technology and video gaming, stuff like that. So we started a show talking about those things, and we did a bunch of episodes, this was back in 2010. Just as the iPad was originally coming out, I remember that being the focus of our first few episodes. Then we had a couple of guests on the show because they were people that we were interested in who seemed to find the show, which was awesome. Then from there, this show ended up having a guest host every single week, and I got to meet a lot of interesting people that way. That show eventually morphed into becoming a full-on weekly interview show, which was called Command Space, when that show moved to the 5by5 network. That show then became Inquisitive on Relay FM, which had a few different lives of its own as well. That was a show that I did every single Wednesday for, and I don’t know six or seven years. I have since moved away from guest format shows, but that’s where it all started.

Joe: You’ve said this– This is so weird because I feel like I know you way better than you know me because I listen to a couple of your shows. I know you’ve said that interview shows are tough, and as somebody who does an interview show, I can definitely relate to that. The other shows that you have are pretty much you and a co-host, or two co-hosts talking about some topic.

Myke: They’re fixed panels, mostly talking about a specific interest field.

Joe: Gotcha. I’m assuming that that’s a lot easier for you now that you are dividing your time between being a podcast host and managing Relay FM.

Myke: Yeah. Because finding guests and booking guests can be difficult. That is a tricky endeavor. Also when you do shows with people who don’t have fixed setups, because they’re not recording every week or whatever, it can end up introducing various technical issues. Audio quality and stuff like that, so those episodes typically take longer to edit and to finalize and to master. But also as well, those shows they take a lot of preparation. I would prepare a lot. I do a lot of research on the hosts and all my guests, and we’ve put a lot of effort into that. Honestly, for me I’ve found that over time those sorts of shows became less feasible from a business perspective. I ended up moving to stuff that was easier, or more creatively fulfilling for me, which is the types of shows that I do now.

Joe: That makes sense, and I’ve definitely hit all of those stumbling points over the last couple of years of doing this show. That and also trying to get maybe a diverse lineup of guests, especially in the web development. There’s a lot of dudes, and I want to try to have more than just people who look and sound like me on the show.

Myke: That is a definite thing. That’s a thing that I would want to do, and we try to– With the hosts that we have on the network we try and have as much of a balance as we can. It’s something that we’re always trying to improve. But yes, that’s another challenge of working on these types of shows today.

Joe: Absolutely. The audio quality thing, I’ve always thought “Maybe I’ll buy a cheap microphone and mail it to my guests,” but that’s more trouble than it’s probably worth.

Myke: You could do that.

Joe: Really?

Myke: That is definitely a feasible thing. I know many shows that have done that kind of thing. I never have, but it is definitely an option.

Joe: Absolutely. And you mentioned that your shows were on 5by5, and it’s about five years ago now that you started Relay FM. What was that like? What was the decision-making process for that like?

Myke: Like, “Why did I decide I wanted to work on Relay FM?”

Joe: Exactly. And what factors did you weigh, because you worked a full-time job as well as podcasting before Relay FM?

Myke: In our beginning. It was a few months after Relay FM was founded that I was able to leave to do this full time. And that was part of the reason, and I felt like if I was in control of everything financially, it would make more sense, owning the company as well as being a host. But also I felt like I had done everything I had set out to do, like when I was running things on my own I had–  We started a small network called 70 Decibels which was transitioned into 5by5 in 2012, and that was a goal. That was a goal for me that when I set out I was like, “This is what I want to do. These are the people that I want to work with.” And I achieved it. I didn’t have anything to focus on, so I decided that the best way for me to be able to push myself and to be able to get to where I wanted to be, was to go out and do everything all over again. I spoke to Stephen Hackett, my co-founder because he was– We’d never arranged anything before with 70 Decibels. It was just my thing. Stephen was instrumental in helping me get everything set up, so I went to him, and I was like, “I have this idea. What do you think?” And he was like, “I was thinking of doing the exact same thing.” So we decided to– It just felt natural that we would do it together because we have complementing skills. He’s good at things. I’m good at things. Together we’re able to build a business out of it.

Joe: That’s fantastic, and that’s something important. I talked to a lot of people, and they’re like, it’s a mixed bag of “Don’t work with a co-founder, especially one that’s your friend.” And then there’s, “Co-founders are so important,” and it sounds like you’re in the latter camp. Because you both complement each other.

Myke: Yes. I understand why some people have those reservations, but a healthy balance can help. For example, me and Stephen separate our personal and business conversations. They don’t happen in the same place. Those two things never intertwine. We’re able to keep things pretty separated, and working together at a pretty high level, we have a lot on the line for five years, and it has not affected our friendship. I don’t know if we are unicorns in that, or maybe we just took extra steps that a lot of people don’t think about. But it’s been fine for us.

Joe: Absolutely. That’s great. If you are thinking about starting a company with a co-founder, Myke just offered some really good advice. Try to keep the personal and the professional things separate.

Myke: I can’t imagine how people would want to found companies on their own. That’s a lonely endeavor.

Joe: It’s tough. This podcast is the most personal interaction I get in being self-employed on the internet. If I was starting a big company, I would definitely want somebody else to bounce ideas off of. So, when you set out to start Relay FM what research did you do? Did you know the logistics of setting things up, or were there things that you had to look into for bringing podcasts together under an umbrella and setting up a website, and things like that?

Myke: I didn’t need to research, because I was already doing it. Relay FM didn’t start from nothing, and it started from four years of knowledge in the field. I knew how to make the shows, and I knew what a system needed. We ended up working– We licensed a product which we eventually bought out and changed the entire code base of to build our [CMS], our publishing platform. But that was a real important part for us, of being able to find someone that we could work with to give us the skeleton to be able to build the system that we now use. That was very important. But honestly, I was bringing to the role my own beliefs for how something like this should be done. So, I didn’t feel like research was needed because I had a very strong vision of what I wanted and Stephen had a very strong vision of what he wanted. We made our company based on those ideals, as opposed to being like “What is the best way to growth hack a podcast network?”

Joe: Absolutely. I like what you said there, and you said that you were bringing four years’ experience. Because I might be a little fuzzy on your relationship to 5by5, I know you had shows on 5by5. But were you a deeper– More deeply involved in that?

Myke: I was running a small network called 70 Decibels beforehand, and 70 Decibels was a company that was making small amounts of money, but it was making money. We had sponsorship arrangements and stuff like that. When we joined 5by5, we moved pretty much all of our shows there, and I maintained the relationship with the people that I brought in. I was helping to manage those people even within that network. I had a small– I had an idea of what it would take to run things, anyway. I was a host on the network  like everybody else, but I was also doing some logistics and administration for the people that I was working with, just so we could make sure that the responsibilities were split because it was bringing in a lot of new people at once and it seemed strange to change their main point of contact.

Joe: That makes sense. It’s almost like when Disney bought Pixar, John Lasseter was still at the helm and Ed Catmull will still at the helm for that company.

Myke: Sure. And also remember, [Slack] [inaudible].

Joe: Right.

Myke: There was no way for people to communicate with each other in the way that we think of it now.

Joe: Absolutely. That’s a super interesting point, too. I like what you said about this, because some of the best advice that I got out of college that I didn’t take immediately was, “If you want to start a company, get a job in the field and learn the ropes from somebody. Make the connections that you need to make under the umbrella of somebody who’s done it before.” It almost sounds like you did that with starting Relay FM. You had 70 Decibels, and then it was brought under the umbrella of 5by5, which is still a very successful podcast network.

Myke: Yeah. I had a sense of what I wanted, I learned from other people and then was able to combine that knowledge together into what I wanted to do for the future. So yes, I would agree. It’s difficult to start something from nothing.

Joe: Absolutely. So, you had a relationship with a bunch of hosts. You had a relationship with sponsors. I know a question that I get  frequently is, “How do I get sponsors for my podcast?” I won’t put you on the spot and ask you that advice because it’s hard. Right?

Myke: You can ask me if you want to ask me. You can ask me. I have an answer if you want it.

Joe: I would love to hear your answer. Because mine was very much like, “I knew people, and they trusted what I did, so they decided to sponsor my podcast at first.”

Myke: That’s a part of the answer. One of the things about getting advertising in the podcast industry today is that the podcast industry is growing and audiences are growing with it. When I started, if you had 1,000 listeners on a show you could quite easily get an advertiser. But now you’re looking at– You want to be in the– If you have one show you want to be in the multiple tens of thousands of downloads before a lot of the traditional advertisers that you hear on most podcasts will want to consider you. If you are part of a larger organization like Relay FM, like how we do it, we have shows that vary from thousands to hundreds of thousands of listeners. We’re able to sell things at a larger scale, like in packages. But if you are one individual with your one show you need to be in the tens of thousands of downloads range before a lot of the traditional podcast advertisers will want to consider you. Because it’s a lot of work for them to put something in, so they want to feel like they’re going to get a good return out of it. But that’s if you’re focusing on the traditional podcast advertiser, which you don’t need to. It’s not what I did. When I was starting out, I contacted small companies, like companies that I believed in and companies I thought, were interesting. To start with, initially, I was doing podcast advertising for next to nothing. Very small amounts of money so I could get used to it. So I knew what the relationship would be like, I knew I would understand how to work on a contract, I would understand how to write copy and deliver that copy. Because if you’re starting out you’re asking a lot for a larger company or for any company to give you a lot of money, so I was doing it as a way to help understand. Also, when I was then going after the larger advertisers for charging what I considered to be more fair amounts at that point, I had a body of work which included advertising which I could say “Look. You can go and listen, and this is what we do.” So, that’s my advice. Don’t go off the square space if it’s your first if you’ve never had ads before. Find a company that is small that relates to the topic that you’re doing and pitch to them.

Joe: That’s fantastic advice, and it makes a lot of sense. It’s almost like you’re not charging the advertiser for the learning curve of selling sponsorships. You’re selling them because–

Myke: Exactly. Because I would say, you’ve got to be effective. If you’re selling ads, you have to be effective for the company. They’re not giving you free money, and they want people to come to their product through you and your ability to tell their story. You need practice in that. It might be a good idea to work on a fair arrangement with a smaller company and then move on from there. That’s my advice.

Joe: That’s good advice. It shows that in your experience because something that you do very well is those live reads. And it’s not just like, “Do you need a new mattress? Get Casper.” It’s like, you tell Casper’s story and your story along with it, and how Casper relates to you.

Myke: Thank you. It’s something I do genuinely try very hard with. I don’t take our advertisers for granted. They are putting food on the table of my home and many others, and I want to try and always do the best job that I can. Plus it helps that we are very choosy about advertisers. We only take advertisement from companies that we believe in the products of. We don’t take advertisement for products and services that we don’t think are valuable. Sometimes we get to try the product, and sometimes we don’t. But if we don’t then, we’ll do a lot of research into understanding if it is a good product before we will go ahead and work with that company. It’s something that we take very seriously also because we know that every time we are doing an advertisement spot, any host is, it sounds like an implicit recommendation or endorsement from the person. Even if that person is not saying so. Even if that person is talking about objective statements, they never had the product, they’re just telling you what the features and benefits are. It always sounds like an endorsement because it’s something in our brains that’s wired that way. By the way, that’s why podcast advertising is so successful and so effective. Because we know that exists we won’t take advertisement from companies that our hosts aren’t willing to read.

Joe: That is a great philosophy, and you’re right. Podcasters are big influencers. Like I said earlier, I feel like even though we have never met and this is our first time talking that’s not a tweet,   I feel like I know you better because I listen to your shows.

Myke: You trust me.

Joe: Exactly.

Myke: You trust what I have to say, and I take that to be a very important thing. It’s part of what makes us successful. It’s because of the trust and the relationship that we have, so we don’t take that lightly.

Break: This episode is brought to you by Pantheon. Starting a new project? Looking for a better hosting platform? Pantheon is an integrated set of tools to build, launch and run websites. Get high performance hosting for your WordPress sites, plus a comprehensive toolkit to supercharge your team and help you launch faster. On Pantheon, you get expert support from real developers, best in class security and the most innovative technology to host and manage your websites. You can sign up a new site in minutes with a free account, and you only pay when it goes live. That is my second favorite feature to Pantheon, only to the easy ability to create dev staging and live servers, and push to GitHub. It’s very easy to set those things up on Pantheon. You can head over to today to set up a free account and pay only when it goes live. Thanks so much to Pantheon for their support of this episode and this season of How I Built It.

Joe: You and [Federico] have convinced me to try to do the iPad only lifestyle, at least when I’m traveling. I cheaped out on the 13 inch MacBook Pro with no touch bar, and it’s been very disappointing to me. I’m like, “I’m just going to try–” I got the 12.9 inch iPad Pro, the new one, and I’m like “I’m going to use this for travel through the rest of the year and see if I can do everything I need to do on it.”

Myke: I think it’s possible.

Joe: So, speaking of that trust– I think so too. The biggest thing for me is coding, but there are a few ways around it, and I’m not coding at the same level that I was two years ago. So I’m excited to give it a go, I have my first big trip in a couple weeks, and I’m going to leave the laptop home and bring the iPad. Cool,  we’re 20 minutes in, and I haven’t asked the title question, which is how did you build it? This network? This show focuses a lot on the technical aspects, so we talked about the philosophy and the logistics a little bit, but you mentioned that you licensed and then subsequently bought out your CMS. It’s safe to say that you’re not using one of the more common ones. A lot of WordPress users and developers listen to this show, and it sounds like you used maybe a custom build?

Myke: It is custom. Yes, it’s completely custom at this point. This is the funny thing, and looking at the technical parts of this, this is why I have a co-founder. Because I am not technical, but I have some basic knowledge. It’s a Rails app. That’s what I know. But we were looking around at some stuff, and there were some options that we could go down, but then we found this product which was great, and we worked with the developer of that product for a while, and they were unable to continue with the development. We were able to buy out the license and build on the code base ourselves. At this point, we’ve rebuilt everything just because it wasn’t necessarily built for the scale that we would end up moving towards in a bunch of different ways. Stephen is effectively the CTO of our company, and he manages that stack, and we have worked with multiple developers. We have a developer on retainer right now who we work through projects with, and we also have some behind the scenes stuff which is even more behind the scenes. Like how we manage our advertising inventory and stuff like that, again we have another program that we license from a friend and we’re now looking at how we could make advancements to that because one of the problems is there aren’t off the shelf tools to manage the type of thing that we’re doing at the scale that we’re at. We have to start with something, and then eventually we outgrow it, and we decided to make the decision a long time ago that we would invest financially into those tools, so if we’ve outgrown something, then we need to build something.

Joe: Gotcha. That makes a lot of sense. Because if you visit Relay FM, you’ve got this joint feed that is all of the most recent episodes, you have a live stream. You stream all or most of your shows live, and then you edit later, you have the advertisers, and then you also have memberships built into that. So somebody can sign up for a membership, and I suspect there’s– Are there secret feeds for members, or–?

Myke: There sure are.

Joe: So there’s a lot going on, and what you said about the importance of investing in this software because it’s running your company is something that a lot of people in the open source space, which is the WordPress space or if they’re part of the WordPress space, needs to hear. Because it’s a lot like Android and iOS. When I was on Android, I was like, “I’m not paying for an app,” because I could get something for free. And when I moved to iOS, I was like, “I’ll pay $70 OmniFocus because it helps me.” The latter is more important there. If this is how you make your money, then you need to invest in it.

Myke: I agree.

Joe: Cool. So, it’s a Rails app. What was the biggest challenge of building out the website for you or for your company?

Myke: It wasn’t initially, but it was soon after, which was scaling. Things grew for us quicker than we were expecting. Our system couldn’t handle it. Getting the right caching and stuff in place took some time, and there was some real– We had some real problems for a while. Every time an episode posted it brought down the website if the show was big enough. We had some real teething issues that we worked out, and we’re in a much better place for it. But that was probably the hardest time of the actual building of all of our technical stuff.

Joe: Gotcha. That’s a crummy problem to have, but it’s on the list of problems that shows that you are growing.

Myke: It’s a frustrating thing, but it’s a good problem. It’s good if you can have that problem. Unless things are really bad, like if it’s so bad that you have ten listeners, but it brings down the website. That’s not so much of a good problem. You know what I mean?

Joe: Yeah.

Myke: But we were in a situation where it was a good problem for us. We did not anticipate the way that things ended up going., but we got there in the end.

Joe: Gotcha. That’s a good thing to hear. If you can share this, I’d be curious to hear what you’re hosting set up is like. If you can answer that, like if you’re working with a hosting company, or–?

Myke: We work with Libsyn. Libsyn hosts the audio files for us. Our system is built in such a way that the audio can come from anywhere, so we are not reliant on one company. That was very important to us that we would not be reliant if somebody changed terms of service or had issues or we weren’t happy with them. We use Libsyn, Libsyn are the best in my opinion. Their interface is not so great, and their interface is really bad. Their publishing tools are very bad. If you want to make– OK, not very bad. They’re very good. They’re just out-of-date from a styling perspective, and there are some companies like Simplecast that do a better job of that, but they have their own problems. I recommend Libsyn. If you are building your own website, Libsyn is 100% the place that you should be hosting your audio. Because the stats are solid, their system is rock solid. We have never ever had an outage in five years with them. They are an incredibly technically rock solid company, but their publishing tools have– They could they could use a refresh. But it’s difficult, they focus their efforts in the technical side and honestly I wouldn’t want them to do it any other way. But there are various platforms available, and this is the one that we’ve chosen to use.

Joe: I’m in agreement. I host this show on Libsyn, and my other show is hosted on Blubrry because I wanted to try them out. But I consider Libsyn an audio-only host. Like, you have Simplecast which is everything, and you can publish episodes with show notes and all that on Libsyn, but I publish the file and move that over to WordPress because that’s how my site is built. So, I agree with you wholeheartedly. The fact that Stuff You Should Know, which is one of the– For a while at least they were using Libsyn, and that was a big boon for me for when I was trying to decide the audio host.

Myke: Yeah, a lot of those– There’s a bit of a consolidation around a platform called Megaphone right now, which is making a lot of promises that I’m intrigued to see if they can actually deliver on. They are a whole platform that we don’t need. We already have our platform, and we’re happy with it as it is.

Joe: I don’t want to go down this rabbit hole a little bit, but I was introduced to them at Podcast Movement over the summer, and it sounds like they are doing some interesting things. Talking about  automatic ad insertion, and–

Myke: Stuff that I’m not interested in.

Joe: Exactly. Cool. I had one more question for you, and I already know the answer to this, but do you edit your own shows or do you outsource that?

Myke: By and large I edit my own shows. We work with editors as well, Relay FM works of a couple of talented people who edit shows, but I edit my own shows.

Joe: Cool. That’s one thing that I knew I wanted to outsource in episode 3.

Myke: Why?

Joe: I was taking out [inaudible], and I’m like, “This is too much work for me.” That was part of it. I didn’t have enough chops to do it in the beginning, and I wanted to outsource it.

Myke: OK. I didn’t either, but I learned as well that I didn’t have the financial ability to be able to do anything different. But the reason that I edit most of my shows is I do believe that a lot of the show is contained in the edit and in the way that it is presented. Yes, that can 100% be handed to somebody else, but that’s not what I want to do for the majority of my stuff. And there are other things, some shows I edit for that reason because I want them to sound a specific way. For some shows, I want to be able to publish them as soon as possible, and the fastest way to get that done is if I do it, because I’m not working around anybody else’s schedule. I’m just working on my own.

Joe: That’s a good point. What do you use for editing?

Myke: Logic Pro.

Joe: Logic? OK. That’s the thing to use. I recently made a bad mistake and moved to a PC as my main work machine, and I’m not–

Myke: Adobe Audition is a very competent editing software, it’s just not the software I use. I use Adobe Audition for some other things, and I use it for volume leveling and noise reduction, stuff like that. But it is a very competent multitrack editor.

Joe: Yes. That is the case. Adobe Premier, I do a lot of video editing too, and Adobe Premiere is supposed to be the thing I’m using. I’m using Camtasia, and that’s a dumpster fire. But I’ve spent too much time trying to get parity between things I use on the Mac and then things I can use on the PC. OmniFocus is one of those things. There’s very little cross-platform tools that I like using on iOS, Mac OS and the PC, so it’s been a weird year long journey. But I’m going to buy an iMac Pro very soon to do all of that stuff. I was just curious as to what you use. I was using GarageBand originally, and now I’m using Audacity here because I don’t do too much editing, but maybe with the right tools and the fact that I know what I’m doing now I’ll give it another go.

Myke: It’s a skill to learn, it’s not easy, but it’s like anything. You can do it.

Joe: Thank you, I appreciate that vote of confidence. As we start to wrap up here, what are some of your plans for the future of Relay FM? Do you have any big things coming down the pike that you can talk about?

Myke: Not particularly. We are not currently working on any new shows actively, which is a rare thing for us. We have some stuff coming later next year, which just some changes to some stuff that exists already. Which is exciting. But for me, one of the big things that I’m focusing on right now is making sure that we have a sense of stability for the future, and how we are able to get to that position. That’s what I’m focusing on. We don’t have a ton of options, things have gone well for us. Luckily we’ve been seeing consistent growth of the company since its beginning, and it doesn’t seem to show any sign of slowing down, but we don’t have grand visions of trying to take over the podcasting industry or change it in any way. We’re comfortable of where we are right now and moving with the industry in the ways that we feel are necessary, but we’re quite lucky that our audience has a strong belief of how they want things to be presented to them. Which is similar to us, so we’re looking to stay the course for a while. We’ve always got projects, I always have projects that I’m working on, but I can’t have anything that is specifically ready to go or that I would even call something that’s going to happen in the next year. Things come and go. A lot of the stuff that we work on, a lot of the time when something it’s because a great idea happened two months before. Because we have the ability to make things happen if a project comes along, and it’s exciting to us, we will move it through until it’s completed. I don’t have anything going on right now, but that doesn’t mean that I won’t have something new in February. If that makes sense.

Joe: Absolutely. That makes sense. I like that. When you see something, it’s because a great idea happened two months before. That’s a solid pull-quote. Though I do need to ask you my favorite question, which is, do you have any trade secrets for us? Trade secrets in the sense that, any good advice around podcasting or running a podcast network?

Myke: I gave you my advertising tips, which is what most people that do this thing typically want. Outside of that, I don’t necessarily– I would say that I don’t think people need to do what I do now. I  don’t think that it is a necessity to start a podcast network. I feel like that was a trend and people [inaudible] networks, but I don’t necessarily think it’s something that you need to do. A lot of the resources that a network can provide can come from different areas now. There are companies that are set up that can try and help you of this where needed, and I don’t think that it’s worth– Counting out the independent podcast, I look at a show like a podcast I enjoy called Do by Friday. They are completely listener supported, and it seems to be a wonderful model for them. What I would suggest is, don’t necessarily base your idea of what you want your show to be on the shows that you already listen to. There are many different types of things you can do out in the world, and I would also recommend from a thematic perspective, from a topic perspective, to do the same. If you want to stand out, you have to stand out. That’s a tricky thing to do, but find the thing that makes you different and focus on it. If you can’t pinpoint the thing that makes you different, you’ve got to keep working on it.

Joe: I like that. There are a lot of good pieces of advice there. “Don’t base the idea of your show on the shows that you listen to,” and “If you want to stand out, you have to stand out.” That’s reminiscent of– I did track and field. Mostly the field part, I’m not built to run fast, but our track coach said “If you want to run fast, then you got to run fast.”

Myke: That’s good advice. I mean, it’s bad advice, but it’s good advice. You can’t do anything with that, but it’s good to hear.

Joe: Right. It’s like Nike’s Just Do It. Just do it. If you’re thinking about starting a show, then start it, and figure out the way that makes you stand out. Myke, I appreciate your time today. Where can people find you?

Myke: Couple of places. If you want to find me personally, I’m @imyke on Instagram and on Twitter. But I host many shows on Relay FM, and you go to to find those and all of the other wonderful podcasts that we have as part of our collective of shows.

Joe: Awesome. I will link all of those in the show notes. Myke, thanks again for your time today. I appreciate it.

Myke: Pleasure.

Outro: Thanks so much to Myke for joining us today. Again, I love all of the advice that he gave us. Things like how he started Relay FM and why he built the website he did, that’s always really interesting to me. And how he got comfortable with going after sponsors, and his approach to it. The thing he said that stuck out to me the most was, “I don’t take our advertisers for granted,” and “We only take ads from companies we believe in.” That’s so important. Because like Myke said, podcasters have a responsibility to their listeners because their listeners trust them. Myke and myself included, we don’t want to hawk anything that we don’t believe in. So, my question of the week for you is, are you going to start a podcast this year? And if so, what is it going to be about? I’d love to hear more about that. Feel free to reach out to me on Twitter, @jcasabona, or email me I want to once again thank our sponsors, Plesk, Castos and Pantheon. If you liked this episode, be sure to head over to Apple podcast and leave a rating and a review. When I last checked the show is in the top 25, it’s at 21 for technology podcast on iTunes, and that is absolutely thanks to you and your support. Thanks so much. I’m excited for 2019, and I have a lot of cool things in store, be sure to stick around. Of course, until next time, get out there and build something.

The post Myke Hurley and Relay FM appeared first on How I Built It.

Jan 15 2019



Rank #8: Episode 25: Bob Dunn & Blogging

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In this episode, Bob and I get back to WordPress basics and talk all about blogging! Bob talks about how he built his blog, using plugins (60+!), coming up with good content, and a lot more. This is an excellent episode for anyone who uses WordPress or wants to start a blog.

Show Notes

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The post Episode 25: Bob Dunn & Blogging appeared first on How I Built It.

Feb 28 2017



Rank #9: Jeremiah Smith and SimpleTiger

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Jeremiah Smith is founder of SimpleTiger, an SEO company that focuses on SaaS companies. This episode is going to kick off a miniseries about SEO and I’m happy that Jeremiah is starting it off. He offers so much incredible advice about SEO and life in general. I love his story, and I think you will too.

Show Notes

Check out my new show, Creator Toolkit and join our Facebook community. Question of the week: What’s the best piece of SEO advice you’ve ever gotten? Let me know on Twitter at @jcasabona or email me,

Sponsored by:
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Intro: Hey everybody and welcome to Episode 90(!!) of How I Built It. In today’s episode I get to talk to Jeremiah Smith, founder of SimpleTiger. This episode is going to kick off a miniseries about SEO and I’m happy that Jeremiah is starting it off. He offers so much incredible advice about SEO and life in general. I love his story, and I think you will too. We’ll get to all of that and more, but first…

Sponsors: Today’s episode is brought to you by Panethon, Traitware, and GravityView. You’ll hear about Pantheon and Traitware a little bit later.

You may have heard of Gravity Forms: it’s hands-down the best form plugin for WordPress websites. It’s amazing for collecting useful data.But what if you want to display those form submissions on your site? What if you want to users to be able to edit and update their submissions? That’s where the GravityView plugin comes in. GravityView lets you easily display and edit your data in a searchable directory with different layout options. It’s fully customizable by you or clients using the drag & drop UI, and it features tons of developer hooks. Don’t waste hours developing custom code for clients—you will have to support that code forever! Save yourself time and save your clients money by choosing GravityView for your next project.

Visit to learn more and enter HOWIBUILTIT on checkout for 15% off your purchase. GravityView comes with a 30-day money-back guarantee, so try it today! That’s And now, on with the show…

Joe Casabona: Hey everybody. Welcome to another episode of How I Built It, the podcast that asks, “How did you build that?” Today my guest is Jeremiah Smith of SimpleTiger. Jeremiah, how are you today?

Jeremiah Smith: I’m doing awesome. Thanks for having me on the show.

Joe: Thanks for being on the show. I really appreciate it. When you guys reached out, when your company reached out there were a few suggested topics. And I think we’re just going to talk about how you created a SimpleTiger today, is that right?

Jeremiah: Yes sir.

Joe: So why don’t we start off with who you are and what you do, and how you came up with the idea?

Jeremiah: Sure. My name is Jeremiah. I’ve been in the SEO industry now for about 12 years, and I pretty much discovered SimpleTiger. It was a marketing agency where I used to offer a whole bunch of different services. From building websites, to designing logos, to actually even printing business cards. I did everything. I thought I could do everything, at least. And I stumbled across Search Engine Optimization through building a website for a client. And after building their website, showing it to them, and they’re like, “This is awesome.” And then a day later they’re like, “OK. Can we get it in Google?”

And I just thought that it was filling out a web form and submitting it to Google, and then you’re done. But I didn’t even realize there’s a whole industry underneath that has so much to do with keeping your site to show up well on Google. So when I discovered that I was immediately like, “This is intriguing. I want to do this for this client. But I can’t really sell this yet.” But they agreed to have me do it as a full-time job for them so long as it worked.

That was their thing. They were just focused on results. And so I had this immediate desire to start learning SEO by doing it. But my goal was obviously to yield results for this client. So that’s when I dove in and it actually worked extremely well. Their company grew massively in a matter of six months and I was ecstatic. I couldn’t believe what I had just learned. And I knew that if I’d just done all of this by learning it, imagine if I knew how to do it and was able to do it for clients.

So I parlayed that into a career in SEO, and went to work for some big ad agencies, and really learned how the big boys do what I do now. That started this side business of SimpleTiger being focused on SEO and consulting, and just got rid of all the other junk I used to do. Building websites, designing logos, printing business cards. All that had to go. I wanted to focus on a SEO. So that is where SimpleTiger was born.

In those days though it was a consulting company, where I didn’t have the personnel to do campaigns for all these huge clients. So I just spent my time consulting them. And that was pretty much how it started.

Joe: Cool. Very cool. Learning by doing is something that I preach all the time. And I’ve said to people, to make them feel better, “You never learn something as well as if you break a client’s site and then have to fix it.” I have always learned the best that way, or at least the fastest.

So what was it like, learning by doing, as far as SEO goes? Because you don’t necessarily see results right away. If I write a line of code and it breaks, I see immediately that it breaks. But with SEO it’s a little bit of a longer game, right?

Jeremiah: Yeah it is. And that was a bit of a challenge. Now what’s awesome is when I was learning SEO, 2006 through 2007, that was the very beginning for me. So when I was learning, those days SEO was much easier than it is today. The tools at your disposal were really good. The stuff that Google gave you access to in regards to keyword data, and things like that, were fantastic. In those days you could you could change a title tag on the website and immediately start ranking better.

That’s totally different nowadays. It’s much harder to rank in Google nowadays. And so I actually was blessed to have that, because it was a good teacher. It allowed me to quickly learn things in those days. But you’re right. SEO does take a little while to take effect. And sometimes that can be a challenge especially when you’re trying to learn something.

So the hard part for me in those days is probably knowing exactly what to do. I didn’t have the experience to filter out what I was reading from what might work and what might not. Nowadays I have that experience and I can quickly tell what I need to do. But that was probably the hardest part in those early days.

Joe: Gotcha. That’s really interesting. That makes a lot of sense, and it was probably easier back then. Because I know when I made my first website I would get links and I would get e-mails all the time, “I’ll trade you link for a link.” And that was the strategy in 2003.

But I mean, 2006-2007 is when Twitter started and then a few years later it started to get big. And the Google algorithm changes quarterly. And because it changes so quickly, what kind of research do you do to stay on top of SEO? I know that there are some big names out there. Matt Cutts used to be a big name, and I think Danny Sullivan. I don’t know if he’s still doing that.

Jeremiah: Yeah. He’s still around. And I definitely recommend people follow Danny Sullivan. He actually left Search Engine Land and joined Google, which is really cool. So now we’ve got somebody who is really involved in the SEO community for a very long time on the inside at Google, which is awesome. I love that. Of course he’s limited with what he can talk about, but he does throw us a bone every now and then.

So I will say following him is a great idea. But if you really understand what Google’s “Why” is, why they exist. And you understand their ethos. If you’ve built a relationship with Google over time like I have, then you can to a large degree predict what they’re going to do. You don’t really need to follow all the news and hype so much.

And that’s one of the biggest filters for me, is I look at the commercial interest that Google has and everything they’re going to take a step in. Because Google’s not going to try to quit making money. They’re going to try to make more. We have to keep that in mind as they move and as they operate. And to a large degree what I’ve learned, and this is the big secret that’s not really a secret in the SEO community, but I want everyone to know about this because I think it’s important.

Be authentic with everything that you create. And if you’re always doing that, you’re doing it creatively and you are doing it prolifically, and you’re creating large pieces of content and several of them. And you’re consistent with that. You’re going to have a fantastic future in search, insofar as Google’s concerned. Because their algorithmic updates are looking for your kind of stuff to promote, and other kind of stuff to disappear.

They want a better index. They want better content to wrap their advertising around. They make more money off of that. So keep that in mind as you build things, and then that will help you predict what Google is going to do next.

Joe: Wow, that’s fantastic. It’s almost like if you want to run a TV ad, you’re going to want to run it either during the Super Bowl or a really popular show, and not just any old thing that some smaller network is putting out. Right?

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Jeremiah: Yeah, pretty much. It’s being creative about what you’re doing. But at the same time understanding that you’ve got to provide value at some level. And being creative is interesting because you bring up a great point. Super Bowl ads are your most creative ads all year, and they’re so exciting to watch. I love it. That’s my favorite part of the Super Bowl, actually. It’s awful.

But I remember that, not this past Super Bowl but the one before that. Miller bought a one second spot because a Super Bowl ad costs a hundred thousand dollars per second. And so they bought a one second spot and it was just a guy for the miller factory wearing a Miller shirt standing in the factory with all beer behind him, and he just goes “High life.” And that was it. It was just a one second thing. And it was it went viral, it was so huge. And that was the cheapest Super Bowl commercial of all time, proportionally speaking. That’s a guerrilla technique of being very creative in capturing your audience, who are very occupied.

And I thought that was cool. I really dig that. But when it comes to SEO, there’s a common misconception. And this is another thing that I try to teach and promulgate this throughout the web. But a lot of people compare SEO to advertising. And that’s the worst mistake you can make because it’s so different. If I were to really explain what a SEO is to you, insofar as what we do in Google, it would be reverse engineering another company’s intellectual property– Google– in order to leverage it to your business’ benefit. So it’s really strange. It’s not advertising.

Joe: Right. I mean, you can throw money at advertising reasonably, and eventually do well. If you have an unlimited amount of money for Google or Facebook ads, eventually you’ll start to convert. But SEO, you need to actually understand the problem that you’re trying to solve. I mean, “optimization” is in the acronym.

Jeremiah: Absolutely. And the funny thing for us has actually been, I would say the hardest challenge for me growing this business over time, has been pricing things appropriately. And the reason being that our inputs are pretty much the same almost no matter what client we work with, because there are certain things that have to happen every single time. Content has to happen. Links have to happen. Things like that. Of course there are more difficult industries than others, but we’ve niched down over time and we figured out our target market.

Because of that, everything looks the same. Almost every campaign we get into there are the nuances and the differences there, but because of that I can build a pricing model that works for what we do. But what’s crazy is what comes out the other end for the client is vastly different in regards to scale and in their industry. So with advertising, that’s not quite the case. Advertising’s got a flat fee for pretty much flat return.

Whereas with SEO, you can scale dramatically. Of course it might be expensive in the beginning when you’re spending $5,000 bucks a month and you’re not getting a lot of results out of it. But a year from now, you might have so much business coming from search that we’ve actually had some clients tell us we have to stop working with you for a little while. Because we’ve got to re-engineer parts of our company to handle the business we’re getting. And that just shows you what kind of power is in SEO.

Joe: Wow. And again it lays credibility to the fact that it’s a long game. I think a lot of people in general believe that the internet could be a get rich quick scheme. Like, “I’ll set up a site. I’ll start a Kickstarter, I’ll start making money. I’ll just SEO my site and I’ll start making money.” But it’s a game of patience.

And I fell into that trap too, when I started my online courses I was like, “I’ll release a course and people will buy it, because people want to learn this.” No, not at all. Why would somebody buy a product from me if they don’t know me? So that’s really interesting. I also like to ask if you’re the mastermind, if you get business advice from folks. And I do want to hear the answer to that question.

But I’m also interested in the discovery process for a client, because you come up with a pricing package, but you said the results could be so different. What kind of stuff do you look for? Do your clients know what they’re looking for when they first come in? Or do they just say, “I want to be number one in Google.” what’s it like?

Jeremiah: Good question. I love that question. I can go deeper on that. It took us a long time to develop the new process that we have for client intake, but this new process is fantastic. We do something in the very beginning that I recommend, pretty much any company that’s offering a service, even down to just building a website. Highly recommend you do. And it’s basically just an intro phase to a project. We call it an opportunity assessment.

With SEO, we’re going to assess your opportunity in regards to search. A lot of SEO companies out there do something similar, but they don’t do anything quite like we do. And there are few agencies that do. And what I see them do it works so well. So we jumped on board with this. The opportunity assessment allows us to check all the different areas that are going to impact them from a SEO perspective, and see how they stack up. Where their strengths and their weaknesses are.

Because what I don’t want to do is try to take some cookie cutter approach to every client and say, “You always need technical optimization. You always need new content. You always need links.” While that may be true that they will always need some amount of those, those proportions may vary dramatically. We’ll deal with some client websites where from a technical perspective, the thing’s built on WordPress, they’ve got all the right plugins, it loads really fast, it’s very clean and smooth. Good user interface.

They don’t really need any technical optimization. Let’s not sell them that. Let’s say, “A lot of companies do need technical optimization. But you guys check off that box, so we’re not going to invoice you for that. Moving on into content. You might need a little bit of content. But where you guys really need help is in your links area.” So we’re going to do a proposal that’s heavy on the links side of things, that’s medium on content and doesn’t include technical. But that’s our full suite.

The opportunity assessment allows us to see all that ahead of time. Now what’s different for us, and we have strong business reasons for doing this. We charge for the opportunity assessment, whereas a lot of companies do it for free. We used to do those for free. But what I found, and this is a nugget that I’m giving your listeners here. What I found is you’ll get a ton of tire kickers coming through and people that want to get this assessment for free. And Our assessment carries some value in it.

When we do that technical chunk, we list the top 10 things that could go wrong from a technical perspective and whether or not they’re wrong on the client’s site. And then we dive into some content strategy and we dive into some offsite strategy. We’re actually providing value in this. So first of all, we charge for that. But second of all it limits the amount of people who are trying to get this free opportunity assessment, down to the ones who are serious and they’re ready to invest in SEO.

And what’s crazy is we charge $200 bucks for our opportunity assessment, which is super-duper cheap compared to the $10,000 dollar Phase 1 project that we’re going to do next. But what that does is that warms them up with a buying relationship with us, and then when it comes to the proposal they’re so much more ready to continue working with us. Because we already feel like we’re engaged in a business relationship. So it works really well for that.

Joe: Very cool. I love that. Because you’re right. You do get a lot of tire kickers. It’s like the people who say, “Design me something, and if I like it I’ll pay for it.” Like, OK. “Give me a meal and if I like it, I’ll pay for the meal.”

Jeremiah: Right. You got all the time in the world.

Joe: Yeah, right. And $200 bucks, to be honest, is not a very high barrier. But it definitely weeds people out. My friend Erin Flynn recently changed her membership model. She used to have this free membership area that she decided that she was going to charge $12 dollars a year for. And what that did was weed out the trolls. The people who were just there, not providing value, being jerks to the community. And she immediately saw an increase in the community, because $12 dollars a year is not a lot of money.

If people answer one question that you post, you have that value. But the people who don’t want to spend any money and get all the free advice are the ones bringing the community down. When I was at Crowd Favorite we did the same thing with that, we charged for the discovery phase because we put real resources into it. We didn’t just look at the website and go, “I think you need this.”

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Jeremiah: Right. We noticed a couple of immediate things that happened after doing that. The first thing that happened was, first of all my sales were up. I spent probably about a third of the amount of time doing opportunity assessments, because now I don’t have a ton of people signing up for these free assessments.

The second thing was our close rate from opportunity assessments increased dramatically, from 20% to 70% to 80%. And it was like, “Heck yeah. Now we’re getting somewhere.” And then the third thing was what you just said. The quality of clientele that we started getting was fantastic, and the retention rates were so much better because we put them through a strict vetting process before we ever began a serious relationship with them. Figuring out all that stuff in the beginning, because SEO is quite frankly, and I hate to say it but It’s very complex.

There’s a lot to a good search engine optimization campaign. I’m not saying smoke and mirrors, I’m just saying there are a lot of things to it that need to be figured out ahead of time. And doing that allows us to figure out a lot of that, instead of just the right campaign for them. To where when we pitch that campaign, and we walk them through the parts that we’re recommending, it all just makes sense. And then they understand, they know, they learn something in the process and they’re ready to buy.

Joe: again, that’s fantastic. I keep saying the same thing over and over again. But you’re making a lot of really good points.

Jeremiah: Oh, good.

Joe: I just thought of a random question that you probably get a lot. This is maybe not usually what I ask, but it is very complex. We talk a lot about Google. Google is always the one that you’re optimizing for. Do you optimize for other search engines? Or is it basically, “I’ve optimized for Google, so I’m pretty much optimized for everything else.”

Jeremiah: Great question. I love this. Side note here, I’m actually teaching at the University of South Florida. I’m teaching senior level marketing students. I taught a class last night, it’s a nice three hour class to give them a deep dive into search engine optimization. And in that class, I got the same question. And I said, “When I’m teaching this stuff and when I’m working with clients, 99% of the time it’s Google. They are the 600 pound gorilla.

And in regards to general commercial web search purposes. But when we really take a step back, Search Engine Optimization is agnostic from a platform perspective. It will work in Amazon. It will work in the Apple iTunes store. If you’ve got a podcast, or you’ve got an app or a song, that kind of stuff. It will actually take effect there. Heck, even an eBay SEO works. So it’s amazing.

I’ve seen eBay stores do really well by having a good SEO strategy for the eBay platform. Everything that applies to Google in regards to how you optimize for Google, does not necessarily apply to Amazon or eBay, of course. Because in Amazon we’re not talking about websites anymore, we’re talking about listings or product listings that you’ve created, and stuff like that. So different rules to the game but the same concept still exists there. But to answer your question, yeah, what we do is primarily for Google.

Joe: Gotcha. Cool. Sweet, I mean we are more than halfway through, I can’t believe how fast this interview is going. And I haven’t gotten into the title question yet. So let’s do that. We’ve talked about SimpleTiger, we’ve talked a bit about strategy and things like that. But how did you build SimpleTiger?

Jeremiah: Oh man. That’s a fun story. I mentioned at the beginning there how I did SEO for the one client and then decided that was that was it for me. I wanted to do that full time. I cut out everything else and focused in on SEO, put that on my resume. Knew that at the time I couldn’t just build an agency out of nothing, I didn’t have anything. I didn’t know how to build an agency. I didn’t know how to run an agency, I didn’t even know how to work at an agency.

So I thought, “I need to go work in an agency and really see if this is it for me.” So I got a job at a huge agency in Atlanta called 360i. And I love those guys, to this day they’re fantastic. They’re huge movers and shakers in the enterprise SEO space. And all of my clients there were Fortune 500 companies. Every single one of them. They were just massive. And I got to see how SEO works on that grand scale. And I quickly learned, that everything is exactly the same for them as it was for that little tiny mom and pop shop that I got my start with. It’s just scaled up.

If it’s content that needs to be created, they create more content. If it’s links that need to be built, they build more links. But the same rules still apply. The same techniques still happen. So I got to learn that and then do that for a lot of huge clients, and while doing that I’ve built my consulting practice on nights and weekends. Just consulting smaller businesses that would never fit 360-I’s budget, that kind of thing.

And over time I just built a bit of notoriety in the community for that. And then eventually I decided to venture off on my own. This was right around 2008-2009 when the economy got really tough, advertising was the first to go. So there was all kinds of shuffling around. I got let go from 360i because We had a lot of SEO people there and everything.

And I was so, at the moment, checked out and checked in to my entrepreneurial idea of building my own thing that it was really a good boost for me. And I’m sure they could probably sense that too, that I was ready to go do something of my own. But they are a really sharp company. They move their people up really well and have a strong tight knit team.

So I left there to go work for another smaller agency, because I still didn’t feel quite ready. And that smaller agency, I brought them an SEO department, basically by building something that they didn’t have there and getting a bunch of clients on board. And that really was where I learned how to take nothing and build an agency out of it, But for someone else. So I had the security blanket of a daily income.

And then I finally hit that that final straw. “I’m totally done working for somebody else, I want to build my own thing. I really want to take SimpleTiger and turn it into an agency.” So I left that last agency there, went off on my own, and that was a little bit terrifying for a moment. But there was actually a deeper, longer term feeling of fear that stuck with me for quite a while. That it was all on me. And so I dove straight into consulting and just picking up consulting clients left and right.

In those days I didn’t have a process put together or anything. I was taking anything I could get, in terms of SEO consulting work. And I had some awesome projects, I had some terrible projects. But after a little while I realized I made really good money doing it, but I was working myself to death. I realized, I’m going to have to build a team. I need people who can help me actually produce results and do the SEO stuff, so I can go out and sell it.

And so I brought my brother on full time. He was interested in SEO at the time, and I taught him a little bit about it. He went to work for another agency for a while just like I did. That was my rite of passage for him. I was like, “You’ve got to go through this. It’ll be good for you. You’ll learn it, and then I’ll be able to afford to pay you to work here because then you could pull some weight.”

And that’s exactly what happened. He came in all beefed up ready to go. He knew how to do it. And so we joined forces and took SimpleTiger from a consultancy to an agency, and started hiring employees and actually building a team. And that’s how we got from there to where we are today. Now our evolution as a company since we started hiring a team has been really fun and exciting. Way easier, and sometimes a little painful, but way easier than just being the consultant doing my own thing by myself. I love having a team.

Joe: There are two things I want to parse out here. Right at the beginning of this story You gave an incredible piece of advice that I want to make sure it lands with the listeners and that’s when you said, “I needed to go work at an agency. I needed to get experience in the industry.” Which is very clairvoyant for a young entrepreneurial person, because I was in that very same situation.

I got a piece of advice from a family friend who said, “When you get out of college you need to get a job at a company and learn how they do things. And then you’ll be ready to go out on your own.” And I being the stubborn New York Italian male that I am, thought, “I know everything. I’ve been doing this since I was 14. What more could I possibly learn at 21?” It was super low risk because I was living at home, I was in grad school for a time.

And it wasn’t until I actually got my first real job that I actually learned, man. I should have listened to that family friend right off the bat. I put myself back maybe two years, or three years. For people who are coming out of college that have the entrepreneurial spirit, you hear about Snapchat and Facebook who get the billion dollar IPOs and they’re college dropouts or whatever. But for most of us, get that experience and make those connections.

Jeremiah: Absolutely.

Joe: And that’s the other question I wanted to ask you, is that you went to a smaller agency after 360i and built out their SEO department. Did you bring your clients with you, or did you start from scratch there?

Jeremiah: Started from scratch there. There’s a huge thing in the agency space, and I didn’t have any real strict non-competes or anything like that in those days. But there was definitely a respectful line, where it is just like, you don’t do that. And I didn’t want to hurt my name at all. I really wanted to keep my relationships with everyone at 360i fantastic. It was purely a logistical reason that I got let go during that whole downturn, and so I wanted to keep those relationships healthy.

Because later on they ended up sending me business. Because believe it or not, 360i’s minimum budgets are massive, and sometimes they’d have some really cool companies come through and they’d refer them over to me and I was able to build my agency based on my past agency relationships. So that was awesome. But I think that’s one big part of it.

What you just said though, about getting a job in the industry, and all that. That is so huge. Because that one year that I did that, I mean it was just one year that I worked at 360i. It wasn’t a really long time. But I learned so much in that one year, I learned several things that I needed to do for my SEO agency. And then I learned a few things that I would probably never do for my agency by working there. And it’s nothing against 360i.

It was just learning my style and figuring out what I wanted to do, and what I wanted to build, versus what there already was out there. And I decided I wanted to build a boutique agency that grows very small, very slowly, very steadily. Very small amount of people that yield massive results. Whereas 360i was not lean. They were huge, we had a ton of people. But we also offered a lot of services outside of SEO.

And I really just wanted to focus on search engine optimization, and also just wanted one niche category of clientele. Because I learned that’s a fantastic way to make money. And I’ve only practiced that over the past year or so and it’s really paying off. I recommend people out there pick a niche. I saw you had a previous podcast of niching down, and I think that’s so powerful. Not enough people do that. But that was something I couldn’t do at 360i.

We had so many huge clients and so many diverse industries, it just didn’t make sense. So I learned all kinds of stuff through that experience and that relationship. And I also learned how to just deal with massive companies, and how at the end of the day, they’re all the same. The numbers might be a little bit different but don’t let that kind of stuff sway you. Continue doing your job based on what you need to do. And you can move the needle for a company as big as NBC or E-Trade. You don’t really have to get bent out of shape over the fact that they’re huge, or anything that. Don’t let that scare you.

Joe: Wow. Great advice. And I will link to the Sarah Dunn episode of niching down. I think that is more excellent advice, especially in software engineering. We call that “domain knowledge.” We want to have domain knowledge of the software system we’re building so that we can build a better system. We understand the users, and our user’s users. Understanding the industry and having that domain knowledge allows you to offer a better service, because you come in knowing a little bit, or maybe a lot, about what your clients need right off the bat. And you can ask those questions that a generalist might not know to ask.

Jeremiah: Right. And that’ll definitely help you close that business well, but that will also help you market your business well. So if we’re talking about search engine optimization again, and it’s for your company and you’ve chosen a niche. Let’s say for example, you’re a software as a service company, and you’re building a piece of software that’s maybe a piece of invoicing software. But your invoicing software just so happens to work best for maybe other software companies, and that’s the niche that you’ve decided to go after.

Now let’s just imagine for a second that you didn’t decide to go after that niche. The keywords that you would write would be things like, “invoicing software.” And you get to compete with the Intuits of the world with QuickBooks and FreshBooks and Zero and all those big names. But if you are invoicing software for software companies, the game changes a little bit. Your key word targeting is going to be software-based or “Software-focused invoicing software,” or “Invoicing software for SaaS,” or something along those lines.

And now your key word pool’s a lot smaller and your target audience is a lot smaller, but they are much more likely to do business with you because of that level of targeting and because of that domain knowledge, like you’re talking about, that you have. I don’t want to go too deep into that. I know you have a separate episode all about niching down, but I would just like to also throw my two cents in that, “Yes, it is very valuable, and it works really well.” Highly recommend it.

Joe: Fantastic. So you told your story and it was a lot of transformation. And we’re totally coming up on time here. I do want to ask you what your plans for the future are. Is it keep an eye on the pulse of SEO? Is AMP going to affect the way you do things? What are your plans for the future?

Jeremiah: Good question. There’s so much about the future of SEO, and that was my finishing statement to my class last night at USF. That was the one thing they wanted to know. “You’ve taught us everything up to now, what’s going to happen in the future?” And that’s such a fun question for me to answer. Because I love theorizing about this stuff. But I will say in regards to SEO looking forward, there’s a bunch of stuff going on that I think your listeners might be interested in hearing a little bit about from someone experienced, like myself, on the subject.

Just so they don’t get swayed by a lot of the hype. And I want to clarify this. Voice search is a big thing that’s happening right now. People are concerned about what that means. People are using the Amazon device, which I can’t say her name right now. She’s listening, and she’ll start talking to me and ruin the whole thing. But there’s that, and then we’ve got the Google’s home device and stuff like that, that are always listening. And those devices, in regards to voice search, those devices are primarily going to help you answer simple questions that just have a very clear black and white answer to them.

They don’t have as much commercial intent capability yet that’s being leveraged. As people I think assume will dominate, I personally don’t think I’m going to be buying a whole lot of products through my Amazon device. That’s just me. But I prefer to look at some things and read a little bit about it, and then click the buy button. Something about that process, actually I literally enjoy doing. So I don’t want a break from that too much, and I think a lot of people are actually a lot more like that.

We have to keep in mind that voice is just an input method, like the keyboard and mouse. It’s just another way of entering in a search query. And then the result that you get, if it’s not going to be on a screen, if it’s going to be vocal then it’s got to make sense to come through that medium. So just keep that in mind. Don’t let the news and hype about voice search throw you off, that “SEO is going to die because voice search is going to take over.” No, there’s going to be a whole new level to it there.

And that’s what that means. It’s going to filter out a lot of the garbage search from what you want, most likely. That’s one part. Another part gets into artificial intelligence, which I don’t have time to go over there. But I wouldn’t worry about that either. Just refer to my first note on SEO which is just be authentic in what you create. Create really good stuff for humans.

Artificial intelligence will learn that and will keep up and you’ll be fine. So those are a couple of things about the future of search. Insofar as my agency is concerned, and growing SimpleTiger, again my goals are just to keep it a boutique agency and focus on delivering the best results for our clients that we can. I don’t have any plans to just blow it out of the water. Of course I do want to see massive growth. I don’t want to grow so fast that it’s a flash in the frying pan experience for us and we have to shut down. That’s something that I fear. So I would rather just grow steadily and healthfully and always be around. So those are my plans for the future.

Joe: I dig that, and I appreciate and I’m sure a lot of the listeners appreciate you not saying the bigger names for the At Home Smart Devices. Awesome. And we’ll leave with this, though I think you just gave us a bunch. Do you have any trade secrets for us?

Jeremiah: I would say a lot of your listeners are probably very tech savvy, and in that regard when we do SEO we break everything down into technical, content, and off site.

And off site usually means link building. Your audience is probably going to be strong on the technical side of things and doesn’t need to do much technical optimization. I’m just going to assume that right out. So because of that I would focus on the meat and potatoes of SEO, which really are building good quality content that’s very user specific, it’s very audience specific. It answers their pain points.

So build that content on your site, and then go get links to that content from other relevant sites. Whether those are blogs or publications on the web, or friends’ websites or whatever. Get links back to that content and you will perform well on SEO. I can guarantee it. That’s the best course of action. And that’s something that you should constantly be doing. I would try my best to plan out some content in advance so that when you start working at it, you don’t have to stop.

Google likes to see fresh content and you will to see it when you start realizing that every blog article you stack up, if it’s part of a plan, brings a new chunk of visitors to your site that are keyword targeted and ready to buy from you. So every time you stack one of those up you’re just compounding the amount of traffic and business you’re ultimately going to get. I’d recommend that your audience just focus on building content, and building links to that content and They’ll do well.

Joe: Focus on building content. Awesome. Now I like to end with that question, but I can’t leave this follow up on the table. Which is, is there some magic publishing schedule? Three blog posts a week? Do I need to blog daily? Or is it just consistent, Good stuff?

Jeremiah: Tim Fair said something fantastic a while back. He said, “What is better? The strict diet that you will not adhere to, or the less strict diet that you will adhere to?” And I love that advice. So come up with a schedule that is not so strict that you won’t adhere to it, but is strict enough that you can handle it. I think that’s fantastic. Now on the opposite end of that, people like Nick Eubanks who are colleagues of mine and have been in SEO forever.

They’ll post case studies where they spent months developing lots of high quality content without publishing any of it. And then one day they’ll publish a hundred articles all at once, and they’ll publish all this stuff. And this is tests that he’s doing in the SEO industry. And he’ll show going from zero to 100,000 monthly search visitors in the span of like a month, after launching the site with all this new content on it.

So Google’s very sharp. Google can quickly determine what’s going on. A lot of crazy things can happen in Google very fast. And he was testing the edges of that. So you’re not going to publish content too quick for Google, I’ll tell you that. When in doubt, if you can publish faster, if you can publish more, do it. But not at the sake or at the cost of quality.

Because that is a big algorithmic indicator, is quality content that people are really going to digest. So longer form articles that go deeper into subjects and provide lots of steps and how to’s, and have some rich media with images, and some video links and stuff like that. That’s going to do way better than a 500 word article on a subject. So keep that in mind too.

Joe: Great advice. I think I’m going to have to change my content strategy a little bit right after we get off this call. Jeremiah, thank you so much for joining me today. I really appreciate you taking the time.

Jeremiah: Awesome. I really enjoyed it and I appreciate the show. I love what you’re working on here, and I was just happy to be a part of it. So thank you.

Joe: Great. Thanks so much. And where can people find you?

Jeremiah: Sure. At You can also find me on Twitter. Twitter handles are @SimpleTiger, as well as myself, @JeremiahCSmith. So hit me up with any questions or anything, I’d be happy to answer questions for your audience anytime.

Outro: I’m so grateful that Jeremiah and I were connected because this interview helped me frame my content strategy, at a time where I needed it. His advice about needed to work in the industry first was some of the best advice I got in college, which I never took. I’m glad Jeremiah did, and I’m glad I eventually did.

And Thanks again to our sponsors Pantheon, Traitware, and GravityView. Their support is deeply appreciated.

The question of the week for you is what’s the best piece of SEO advice you’ve ever gotten? Let me know on Twitter at @jcasabona or email me,

For all of the show notes, head over to If you like the show, head over to Apple Podcasts and leaving us a rating and review. It helps people discover us! You can also join the Facebook community over at I want to build a strong community for this podcast, and Facebook is the place to do it. Finally, if you’re interested in the different tools and services I use to build websites, check out my new podcast, Creator Toolkit over at

And until next time, get out there and build something!

The post Jeremiah Smith and SimpleTiger appeared first on How I Built It.

Aug 21 2018



Rank #10: Exploring VC Funding with Nathan Beckord

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Nathan Beckord is the CEO of Founder Suite, a group of tools to help those seeking venture capital, as well as tools for venture capitalists. We talked all about how he built this after spending a decade helping startups raise their own VC. We also cover how to seek VC funding, and if business plans are even useful anymore. It’s a fun conversation in an area I’m only loosely familiar with – so I learned a lot. I think you will too!

Show Notes

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Joe: Hey everybody, as we gear up for 2020 I want to hear from you and the things that you’d like to see on this show. If you have a question, a comment, a topic, a guest, any kind of suggestion for How I Built It in 2020, let me know by going to HowIBuilt.It/Feedback. That’s HowIBuilt.It/Feedback if you would like to see something on this show in 2020. And now, on with the show.

Nathan Beckord: Put yourself in the shoes of an investor. People are coming at you all day long, 50 people a day knocking on your door, seeking money from you. Are you going to take someone seriously if it’s just an idea and they haven’t put any real either time, blood, sweat, effort, money into it? This guy’s not serious.

Joe: Nathan Beckord is the CEO of Founder Suite, a group of tools to help those seeking venture capital, as well as tools for venture capitalists. We talk all about how he built this after spending a decade helping startups raise their own VC funds. We also cover how to seek VC funding, and if business plans are even useful anymore. I had to write a business plan about 10 years ago, and it was not fun. I was not a big fan of it because it asked things like, what is your exit strategy? We talk about all of that, so this is a great conversation. It’s a fun conversation because it’s an area I’m only loosely familiar with, so I learned a lot, and I think you will too. We’ll get into all of that right after a word from our sponsors.

Joe: This episode is brought to you by our friends at Ahoy, the easiest way to increase customer engagement on your WordPress site. Install Ahoy, create a message box, configure where to display it, and start seeing conversions come in. You can create messages for cart abandonment, upsells and cross-sells, custom support, and so much more. Ahoy’s flexible conditions let you choose exactly where, and when you want your message to be displayed. I’ve recently installed it on my own WooCommerce site, and I’ve already seen increased engagement. And, I know this because of Ahoy’s powerful analytics and reporting. You will see ROI within days of installing Ahoy, if not sooner. That’s even more true for listeners of How I Built It.

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Joe: Hey everybody, and welcome to another episode of How I Built It, the podcast that asks, how did you build that? Today my guest is Nathan Beckord, he is the CEO of Nathan, how are you today?

Nathan Beckord: Very, very good. Thank you so much for having me.

Joe: Thanks for coming on the show. I’m excited to talk about this topic because it’s not something that I often talk about, but Founder Suite is basically software to help people get funding for their ideas. Is that about right?

Nathan Beckord: Yeah, that’s correct. It’s software for raising capital and managing investors, used by startups.

Joe: Awesome. I mean, did you come up with this idea because you were looking for funding, or because you were funding projects and you wanted a better way to do it? What was kind of the genesis of the idea for Founder Suite?

Nathan Beckord: Yeah, I spent 10 years or so as a consultant, kind of a CFO consultant working with startups, helping them raise capital. In doing that I built some stuff, like these elaborate spreadsheets in Excel that I’d use to help track and manage the investor pipeline, and things like that. It was kind of like, as a consultant I built some stuff. I’m like, “You know what? This could actually be a product that might have a broader audience, beyond just using it with my clients.” That’s really where the idea came from.

Joe: Oh, that’s great. So you basically have this internal tool that you built with spreadsheets, that you decided to productize. Now, for someone who has never gone through the process of getting any kind of funding, my dad gave me an initial investment of like $1,000 for my business. But, that was more of a symbolic thing. What is the process for getting funding like, just like a 10,000 foot overview to set the stage here?

Nathan Beckord: There’s two parts to that question, or two answers to the question. There are as many funding stories, and ways people raise money as there are startups in the universe. In other words, there’s kind of not really a right way, or people get it done in 1,000 different ways. But, in my strongly held belief, there is kind of a right way to do it.

Nathan Beckord: The right way to do it would be to first, spend a pretty good chunk of time, often 50 to 100 hours building a target list of investors. That’s tapping a lot of different databases, and sources out on the web, to build a list of 50 to 200 potential target investors, figuring out how to reach them if you have mutual connections. Doing the research, and then really getting out there and hustling, and trying to get some heat going for your deal. We call that running a process, where you’re really running a sales process for a period of X months, two to six months, where you’re really just taking this around to investors in your target list, getting them interested, keeping them up to date with what’s going on, and trying to get some competitive bidding situation going for your startup. That’s what we think about fundraising.

Joe: Gotcha. You said like 50 to 100 hours building a list of possible investors, that is probably a larger chunk … that’s more time than I expected to hear. But, then there’s like the rest of the preparation, right? I mean, it’s … I can just build some website thing that I think is a good idea, but then I don’t just show that to investors and say, “Hey, I built this, and you should give me money to keep building it.” Right? You need like a … How important is a business plan in the traditional sense?

Nathan Beckord: Yeah, I mean so that number of hours and research is a shock to people I think, because a lot of founders are like, “All right, I want to go raise money. I just start, get out there, and-”

Joe: Yeah.

Nathan Beckord: … “start hustling.” That research, but if you take the time to do that research and really build a nice funnel, we call it a pipeline or funnel of potential investors, everything goes faster once you’ve done that work. It’s, another thing we kind of refer back to a lot is fundraising is just like another sales process, right? Sales people build a pipeline of prospects, and they put in a lot of time building their sales funnel. We just want to do that same thing with fundraising.

Nathan Beckord: To your other question, I mean a business plan, it’s funny because when I was consulting years ago, everyone would write a detailed business plan, and these were actual physical-

Joe: Mm-hmm (affirmative).

Nathan Beckord: … written documents.

Joe: Yeah.

Nathan Beckord: 20 to 50 pages long. No one does that anymore. However, the stuff that used to go into these business plans, like announcements of your target market, and competitive situation, and your business model, how you are going to make money. All that stuff is still really important, and stuff you still need to know and be able to communicate to investors, right? But, the physical written plan, no one does that anymore. Fortunately.

Joe: Yeah. Right, absolutely. I said I’ve never gone for funding, but I did enter a business plan competition when I was a student. I just remember thinking, “Here’s the template you need to follow.” We placed third, so I guess it was like the third best idea, or maybe the third best business plan. I’m just like, “What’s my exit strategy? How much do I think I’m going to make in five years?” I felt like a lot of it was guess work, but it was my first kind of foray into this world. I guess I’m happy that people aren’t doing that anymore, but it is important to still know kind of who your competitors are, right? And, why you think this idea is profitable, right? I suspect that, that’s a very important part of actually getting funding, because the people who are investing want to see a return on their investment, either through what? A seller going public, is that-

Nathan Beckord: Right.

Joe: … okay, cool, cool. So the stage is set a little bit for kind of how you go about getting funding. If I were to signup for … First of all, the Founder Suite is for somebody who does want to raise funding, and come up with, and like find investors, right?

Nathan Beckord: Mm-hmm (affirmative), yeah.

Joe: What does that process look like, if I were to sign up today for that?

Nathan Beckord: Yeah, so we have five different tools within the platform, and they kind of match how fundraising actually happens. We have a database of investors, it’s like 40,000 funds, and about 100,000 angels, and high net worth individuals. Of course that is something you search on by industry, or location, or type, to help build that top of the funnel, right? To help build that target list, so that’s the database.

Nathan Beckord: Then, we have a CRM, which is like a Kanban Board style, where you have each investor is represented by a small card. And you’ve got stages on this board where it’s like new, research, contacted, pitched, due diligence, said yes, said no. You have this pipeline management tool so you’re kind of managing all these investors through the stages of fundraising. Then we have this investor update tool, which is really kind of to do this regular ongoing newsletters, right? Whether you’re building relationships with investors, or if you’re lucky enough and you raise some money, you’ve got to keep these investors up to date with what’s going on with your company and your business, so this is a very nice newsletter tool designed to do that. There’s a pitch deck hosting tool, one of the most common things. People don’t do business plans anymore, but you still need a pretty solid pitch deck, right?

Joe: Yeah.

Nathan Beckord: PowerPoint, PDF, this is a way to upload that into the Cloud, create a URL around that, which you can then send to investors, track which investors are looking at your pitch deck. And then, last but not least is a collection of like startup documents. Things like pitch decks, term sheets, cap tables, kind of the … these are Word files and Excel files, things that you need to get the deal done. We’re trying to create this end to end suite of tools, really to help you get this job done, which is a pretty painful job.

Joe: Yeah, I mean just like the idea of kind of going to people and asking them for money. That’s a big risk either way, but I mean making the process easier. It sounds like the process is easier for both you, and … for both the person seeking funds, and the investors, right? Because you have these kind of premade documents that I’m sure the investors probably like to use, or like to see so that they don’t have to spin their wheels or whatever.

Nathan Beckord: Absolutely. I mean, most … I don’t know what the, I’m making up this statistic. But, call it 99% of founders who are raising money, this is their first time doing it, right?

Joe: Mm-hmm (affirmative). Yeah, right, right.

Nathan Beckord: So, anything that helps them kind of learn the process faster, and reduces some of the friction, and complexity, and frustration, that’s what we’re all about. Yeah.

Joe: Yeah, that’s fantastic. The investor update tool was something that kind of jumped out to me as you were kind of explaining this, because you mentioned that it’s not necessarily just people who have already invested, it’s maybe people who expressed some sort of interest, right? Maybe they said, “You need to hit this milestone before we invest.” Is it something like that?

Nathan Beckord: Absolutely. That’s, you’re hitting the nail on the head. I kind of think of the investor update as two different tools. It’s one tool, but there’s sort of two different uses. One is, after you’ve raised money, you’ve got to keep your investors updated with what’s going on in the business. That’s just your fiduciary duty as an entrepreneur to do that, right? But, the other part is before raising money is, kind of the marketing side of things, right? You might have 100 investors on your target list, or your prospect list, and you want to be building a relationship with them, and kind of showing them that you’re a founder who can execute, and get things done, and you’re moving the needle. That has to play out over usually a period of time, right? That doesn’t happen in one month.

Joe: Mm-hmm (affirmative).

Nathan Beckord: That’s like, they want to watch you as an entrepreneur, and see how you’re making progress. That’s where the investor update tool really helps to kind of warm up those investor relationships, even before asking them for money. Really important like funding hack, if you want to call it that.

Joe: Yeah, yeah. They want to get to know you, right? I mean, if you’re selling a product online, it’s more likely somebody’s going to buy something from you if they know, like, and trust you. I’m sure that’s even more magnified when you’re asking somebody for several thousand, tens of thousands of dollars, whatever it is that you’re asking for, to fund your business.

Nathan Beckord: 100%. You hear people call fundraising like a marriage, you’re sort of getting married to these investors for the next five to 10 years of your life. You can’t really get rid of investors once they’ve invested in your company, they’re attached to you, and you’re attached to them. Building that relationship in advance is really super, super important.

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Joe: I’ve always wondered about this but I’ve never known who to ask, right? There’s the, as I mentioned before there’s like the exit plan, right? Where you either sell, or you go public. But, there’s also the dreaded third option, right? Which is your business fails. What happens, maybe if you can talk about this, what happens if say, you give me $10,000 to start a business, that’s a very … I assume that’s a rather low number. But, let’s say you give me $10,000 to start a business, and the business fails. Am I beholden to you at all for that $10,000, or is it like some assumed risk on the investors part?

Nathan Beckord: It’s assumed risk on the investors part, in most scenarios. I mean, there are exceptions. But, in most scenarios you’re buying equity in the business. And that business fails, that equity is now worthless. The only exceptions to that are, is if you structure it as like a loan, or debt.

Joe: Mm-hmm (affirmative).

Nathan Beckord: Sometimes creditors have a claim on the business, where if there’s any value remaining, like patents or something like that, or IP. In your case, a whole content catalog, maybe they’d have a claim to that, where they’d get that. But in general, it’s just the assumed risk of the business.

Joe: Yep.

Nathan Beckord: You fail, I fail as the investor, yeah.

Joe: Gotcha. I mean, which is why they want to get to know you over the course of several months before they want to invest in you, right?

Nathan Beckord: Totally, yeah.

Joe: Cool, so let’s get to the title question here, which is how did you build it? I know you have this experience, I’ve talked to more technical people, I come from a web development background. But, you can interpret this question however you’d like. Maybe from the business structuring side, or if you know the tech behind how the actual website was built, we could talk about that. You have free rein here.

Nathan Beckord: How did I build? As I mentioned in the beginning of this, I had some sort of predecessors to the software in the form of like Excel sheets, and things I kind of built. I am not a technical guy at all really. I’m a business guy, finance guy to be exact. It was actually very daunting like, “Okay, I’ve got this idea. How do I build this?” First, I spent maybe a month trying to find a technical co-founder, someone who would just signup with me, and build this for me, right? That really was useless, you know?

Joe: Yeah.

Nathan Beckord: If you’re a good engineer, coder, you don’t want to just take a gamble for equity on someone else’s idea.

Joe: Mm-hmm (affirmative).

Nathan Beckord: So I stopped looking for a technical co-founder, and hired a development shop actually, in Poland. I went to a meetup for like designers, and at the end they let you get up with a mic, open mic for 30 seconds, and make a little pitch. I’m like, “Looking for help building this idea I have,” and this guy in the audience is like, “Oh, we’ve got a development shop in Poland that can help you out with companies called Code Quest.”

Nathan Beckord: Still working with them five years later, and so really used them just to build an MVP of the product, which was like $30,000 or something, you know? Kind of out of my savings. And, used that to at least put something in the market, right? As a proof of concept, and then I would go do consulting work, get some money, take that money, put it back into the business to build out more features. It was really slow and painful process, because it’d like … nothing would happen for two months as I’m saving up money, and then I’d put some money into the business.

Nathan Beckord: Eventually we had sort of a … I laugh at it now when I look at it, but it was a working prototype or MVP, that then I was able to go around, and take to investors and say, “Here’s the vision, here’s some proof points, people are actually using this thing.” Eventually raised some money on ourselves, just a little under a million dollars, and used that to actually rebuild the platform, and hire some engineers, and actually build it. Like a proper, a proper-

Joe: Yeah.

Nathan Beckord: … version of the software, yeah.

Joe: Wow, so I have multiple questions here. I think I’m going to go in the order in which I think you can answer them maybe the most easily is what I’m guessing. You mentioned first that you used your own money before, to get a prototype built essentially, and then got investors. How important is it to investors to see that I, the one seeking funding, am willing to invest my own money into this business?

Nathan Beckord: It’s very important I think. Even if it’s not money, if it’s time-

Joe: Mm-hmm (affirmative).

Nathan Beckord: … effort, hustle, you know? I always like to answer this like, put yourself in the shoes of an investor. People are coming at you all day long, 50 people a day knocking on your door, seeking money from you, you know? Are you going to take someone seriously if it’s just an idea and they haven’t put any real either time, blood, sweat, effort, money into it, right? This guy’s not serious, right?

Joe: Mm-hmm (affirmative).

Nathan Beckord: Yeah, very important. You just got to show, versus tell, right? Show me what you’re doing, and I think that’s what it comes down to.

Joe: Yeah, I think that makes a lot of sense, right? Instead of saying like, “Hey, I think I have a good idea. Will you hand me money to do it?” Say like, “I believe in this enough to invest my own time, or my weekends,” if I’m working a full-time job or whatever, “To put time into this.” I think that’s really important. And then, the other thing you mentioned was that it was a slow process. I think that maybe there’s a good takeaway there, because I feel like a lot of people still feel the internet is kind of like a get rich quick playground, right? They hear like, “Oh, Facebook made like a bajillion dollars while Mark Zuckerberg was still at Harvard,” or whatever. Or like Google, like somebody just handed Google a check and didn’t expect like no deals or whatever.

Joe: But, I think that’s an important point. You know what you’re doing, you’re investing your money. And it’s probably going to take longer than you think it’s going to, if you want to do it right.

Nathan Beckord: Totally. A lot of times these overnight success stories that sound overnight, actually had a seven years of buildup before it, you know?

Joe: Yeah, yeah.

Nathan Beckord: Excuse me. And, surprising when people really dig into some of these businesses that are going public. Like, they’ve been around for 10 years or whatever, right? It’s not overnight. In those early days, especially if you’re not a technical … if you’re not the hacker who can code this away-

Joe: Mm-hmm (affirmative).

Nathan Beckord: … 14 hours a day, it’s just going to take longer, you know?

Joe: Yeah, absolutely. I like to think about the Olympics like that. People see the gold medalist, but they don’t see that the gold medalist has dedicated their entire life to getting to the point where they are now an Olympic gold medalist.

Nathan Beckord: Totally, yeah.

Joe: Yeah, I think that’s really interesting. And then what you just said eludes to the last question that I wanted to ask around this which is, what was it like being a non technical person working with an agency? I know a lot of technical people listen to this. I do a lot of client work with non technical people, I’m also in the education space so I try to be mindful of that. But, what was the communication like there?

Nathan Beckord: Mm-hmm (affirmative), yeah. Challenging for sure, it was … as a business person you have to I guess, suppress your ego, and eagerness a little bit.

Joe: Mm-hmm (affirmative).

Nathan Beckord: And, kind of learn how to talk about business ideas, and product ideas in a little bit more technical terms. I did have a product manager who was I guess sort of the intermediary between obviously the engineers and me, which was very helpful, right?

Joe: Mm-hmm (affirmative).

Nathan Beckord: I think there’s no way, if I had not had a project manager and I was just interfacing directly with the engineers, it would have been a mess. I will say one of the mistakes I made in the early days is just like, every feature idea that I have, I wanted to like build it in there, and not having that filter of a product manager was a mistake. Gosh, you just have to keep yourself away from messing up the app, you know?

Joe: Yeah, which is like … I mean, that’s I think the most important role of a project manager, right? Is they’re protecting you the client from making sure you don’t blow your budget, or you don’t try to put too much in at the same time to make it a bad app. They should also be protecting the dev team from what’s called scope creep, right?

Nathan Beckord: Yep.

Joe: I’ve worked with project managers who just liked saying yes to the client, and as a result the developers weren’t happy, and the client wasn’t happy. I think that’s an important role the project manager needs to play.

Nathan Beckord: Totally, yeah.

Joe: You mentioned, and so … I mean, you had a bunch of ideas, you were really excited about this. You were working with a project manager, so the project manager I suspect would talk to you, get the features, like the ideas that you had, and then essentially translate them to the development team? Is that about right?

Nathan Beckord: That’s right. The project manager, he and I would sit down, sometimes have a beer, sometimes in front of a whiteboard, and just kind of scope out stuff, and throw stuff up on the whiteboard. Then, he would take it, and I think at the time we were using Gira for this, and kind of turn them into development tickets. We’ve switched to Trello now for a lot of that work-

Joe: Yeah.

Nathan Beckord: … and, a different project manager. But yeah, that’s basically it. He would kind of take the ideas and put them into development tickets.

Joe: Cool, very cool. And then as far as testing goes, was it you doing most of the testing, and did you have other people testing as well?

Nathan Beckord: Yeah. Me, and the project manager, and probably needed to do more of that. I would say that was another maybe mistake, is we put things out to the live, into the universe probably before they were really ready. You’re kind of hoping your early users are patient with you.

Joe: Mm-hmm (affirmative).

Nathan Beckord: And, they’re not always, right? Yeah.

Joe: I mean, that’s really interesting and funny. I mean, it’s something that I feel like every developer, every person building something wants to do, they’ve tested something. I personally am very bad at testing, because I equate it to like building a chair, and then slamming that chair against the wall to see if it breaks. Like, you don’t want to break your chair.

Nathan Beckord: Yeah.

Joe: I can totally level with that.

Nathan Beckord: Not as sexy as building stuff, you know?

Joe: Yeah.

Nathan Beckord: Testing, [inaudible 00:27:10].

Joe: Yeah, exactly. But, it’s the stuff that the users are going to see, so it is important.

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Joe: Moving on actually to that next point, how did you get users? It sounds like it was mostly you in the beginning, you hired this development firm to do the development. Somebody had to do the marketing as well to get people on the platform.

Nathan Beckord: It was mostly me doing that, because I’m a little better at that than development I would say. But we, gosh, we did everything you can imagine. We did a lot of going around to these tech startup conferences like Launch Conference, TechCrunch Disrupt, and a handful of other ones. We’d get a demo table, get our laptop and monitor out there, get some cheap swag, some beer koozie’s or whatever, and kind of hustle on the trade room floor. We put on a couple events related to fundraising, where we’d find a WeWork Space or something, where we could have 100 people in a room, and we’d get a couple venture capitalists to come in as speakers, then we’d sell tickets to people, so we’d kind of build an audience, you know? Obviously for what we’re doing, by throwing on events.

Nathan Beckord: Started to do a little content marketing, and over time our marketing thing has become much more content marketing focused than event driven than it used to be. And then, just kind of reaching out to everyone I know on LinkedIn and other places, and kind of telling them what we’re up to. And usually having to ask like, “Can you introduce me to founders who might be raising money? Can you introduce me to accelerators who might find a use for this?” Things like that.

Joe: Yeah. Wow, that’s super interesting. Mostly the part where you would hold events, you would host events to try to get users. I know that actually, to pull back the curtain a little bit when you filled out the Calendly link, that was specifically mentioned, right? Building events and podcasts as part of a product platform. Can you expand on that part a little bit, and kind of how you realized, “Hey, we should host our own events,” to build an audience?

Nathan Beckord: Yeah, it’s actually a pretty … it was great. We haven’t done an event in a year unfortunately, but we do one called Funding 2.0, kind of the future of raising capital, having some nice grandiose title that intrigues people. But, in the early days it was a great growth hack, because you think about it, right? You maybe paw 500 bucks to get a space, you pay another 500 bucks for pizza and beer. Then, you get a couple speakers who are draws to audience, they’ll usually do it for free, right? Because they want to build their own brand. And then you sell tickets, right? You sell tickets on Eventbrite and stuff like this, and a couple of them, we actually made a couple thousand dollars on the events.

Joe: Wow.

Nathan Beckord: I think one, we made like five grand on something like that. It’s getting our name out there, it’s getting an audience. I think our biggest one might have even been like 300 people.

Joe: Wow.

Nathan Beckord: So you get 300 people in the room, captive audience. They’re there because they’re interested in venture capital, or raising capital. Obviously you’re moderating the sessions, so you’re introducing Founder Suite and what you do, so you’re kind of promoting there at the end. And, you also have their email addresses, because they signed up through Eventbrite. And, you make $5,000 on it, so it was-

Joe: Yeah.

Nathan Beckord: … Now, the caveat is it takes a crazy amount of actual time and effort-

Joe: Right.

Nathan Beckord: … to put on events. I’m making it sound much easier than it is. But, you know-

Joe: Yeah. You can’t just like find an event, and then the next day have it. Yeah.

Nathan Beckord: … Right. It takes a couple months of prepping and planning. And, you’re always worried the week beforehand that the room’s going to be empty, you know?

Joe: Yeah.

Nathan Beckord: It’s like, “Is anyone going to show up to this? Am I going to lose money on this?” It can be pretty stressful, but it can be pretty good too. Yeah.

Joe: Wow. Yeah, that’s fantastic. Especially Eventbrite’s a great tool, is another one where you could probably find an audience in an area pretty quickly. But, I think that’s a great idea, and it’s probably under utilized, especially in an increasingly remote world, right? When you said that you and your project manager would get together in front of a whiteboard I’m like, “You worked in the same room? [inaudible 00:33:25]?”

Nathan Beckord: Yeah.

Joe: I think that’s really interesting, and I think that’s a really cool idea. As we’re coming up on time here, you kind of mentioned Funding 2.0, and I’d love to talk about plans for the future. Not only of, but also of kind of venture capital in general, and getting investors. Because now there’s like, I mean there’s like Kickstarter and Indiegogo for example, I think those are probably a different animal. But, then there are also tools where you can get a bunch of, “Micro investors,” quote/unquote, right? But, they’re like actual angel investors. And the term, or the website is totally escaping my … the name is totally escaping me right now, but I know my friend used it to get funding for his startup.

Nathan Beckord: Hmm, was it a crowdfunding platform, or something else?

Joe: It wasn’t crowdfunding in the same sense as Kickstarter and Indiegogo, like I think there were actual investors on there making smaller investments. I really wish that I could remember the name of it, but-

Nathan Beckord: Well, there are-

Joe: … Yeah.

Nathan Beckord: … so you have, there are a number of sites out there. There’s, I can’t even think, there’s a bunch of them. Kickstarter and Indiegogo are interesting, right? They kind of pioneered the crowdfunding model, but it would usually be crowdfund like where you are basically pre-purchasing a consumer product, “I’ve got an idea for a new clock radio,” or whatever the thing is.

Joe: Mm-hmm (affirmative).

Nathan Beckord: Cooler with a radio built into it, or whatever. And you’re backing it, giving the company money, you’re getting the product before everyone else, and some other perks. A whole bunch of other sites have come on and done equity crowdfunding, which is probably what your friend was doing.

Joe: Mm-hmm (affirmative).

Nathan Beckord: Where, investors can buy small amounts of stock in a startup.

Joe: Yeah.

Nathan Beckord: That can work. I have thoughts on this. Equity crowdfunding can work if you’ve got one of two things, either something like really unique and novel. Again, I think one of those Kickstarter campaigns was like that cooler with a built in radio.

Joe: Right.

Nathan Beckord: Something that’s like really cool, and people are just fired up about it. Or, if you already have an audience that you can tap to invest in your business, right? Like you’ve got followers for your show. If you were going to crowdfund for your show, you might be able to tap that audience to invest. If you don’t have those two things, I don’t think equity crowdfunding is very compelling. A lot of these sites will sell you on this idea that you just come in, pay them 100 bucks, or 1,000 bucks, whatever it is, post up like a description of your business, and investors are going to flock to you. That doesn’t, that’s not reality. You kind of have to bring your own audience.

Joe: Yeah, that’s a really good point. That’s actually a lesson that I just learned, I went to like a Patreon workshop recently because I’m trying to build up the Patreon for my podcast and I thought just like, “Oh, I’ll post a page, people will pay five dollars a month.” I’m like, but I’m barely telling them about it, I am not giving them any benefits that are worth the five dollars a month, so I think you’re absolutely right about that. AngelList, is that one? That’s the name that just came to mind, where like-

Nathan Beckord: Yeah.

Joe: … Yes, okay.

Nathan Beckord: They’re one of the older, and probably larger equity type crowdfunding … I don’t even know if they call themselves that anymore. But yeah, they are in that category. We actually raised a little bit of money on AngelList, which was great. They’ve evolved a little bit since those days, I don’t know how long recently your friend did it. But, now they’re more helping facilitate syndicates, so if you’re an angel investor you can build out a syndicate, and do deals. I think that’s …

Joe: Gotcha.

Nathan Beckord: Yep.

Joe: Yep. Actually, that’s a really interesting kind of not necessarily reversal, but a direction change. I guess the root of my question is, and I think I probably know the answer to this already. Do you think that platforms like this are eventually going to replace our traditional investors? Actually, let me stop there because we’ve never actually defined types of investors, right? You have, I think they say that the first investors you should go for are friends, fools, and family. Is that right, yeah?

Nathan Beckord: Yeah, sure, right.

Joe: Then is it angel investors?

Nathan Beckord: Yeah, typically angels. Then beyond angels you might have seed funds-

Joe: Mm-hmm (affirmative).

Nathan Beckord: … seed venture funds, and then larger venture funds. Then, as you kind of get way later, you have your private equity firms. There are other entities around there like family offices, that’s usually like an investment team doing deals on behalf of like a wealthy family.

Joe: Mm-hmm (affirmative).

Nathan Beckord: There are some other types of investors out there too, yeah.

Joe: Gotcha. I mean, so do you think that these types of crowdfunded platforms could eventually replace the traditional investment models? Or, do you think that they’re pretty much here to stay because ideas are getting bigger, funding is such an integral part to a startup business?

Nathan Beckord: Yeah, the problem with some of these platforms is, I call it the adverse selection problem. Where, the neediest … so, it’s a marketplace, right?

Joe: Mm-hmm (affirmative).

Nathan Beckord: You’re trying to have startups on one side, and investors on the other. The neediest startups are the ones that often gravitate towards these platforms. Sometimes, kind of let’s be honest, the crappiest startups-

Joe: Yeah, right.

Nathan Beckord: … are the ones that are like, tried to raise money other ways, they can’t. So, they’re now flocking to these platforms. And on the other side of the coin, top tier investors already have so many good deals coming at them, that they don’t need to come to these platforms. In some ways there’s this adverse selection problem where, both sides, you’re sort of drawing in crappier companies, and crappier investors.

Joe: Yeah.

Nathan Beckord: I think that’s a hard thing to break out of sometimes, right? Because, really good startups, and really good investors don’t need these platforms. Yeah.

Joe: Yeah, right. That’s a good point. I mean like, I’m going to use the name that everybody recognizes, right? But, like Peter Thiel isn’t going to be on AngelList, or seed lead, or whatever, you know? Any of these websites, because he’s got plenty going on in his world. And then like you said, right? I mean, the Google story is so interesting to me because the founders were basically like, “We want money, but we don’t really want to give equity.” That worked for a little while, right? Where people just kind of cut them checks to be like, “All right, this is very revolutionary.” Right? They wouldn’t need to go to a website like this because their idea was so revolutionary.

Nathan Beckord: Yeah, right.

Joe: Awesome. Yeah, well Nathan, thanks so much for your time, I really appreciate it. I do need to ask my favorite question, which is do you have any trade secrets for us?

Nathan Beckord: Trade secrets? Oh, interesting. You know, I think that’s a good question. I think trying to figure out things to do for your business, to grow and market, that are scalable is the hardest thing to do, but what you’ve got to do. I’ll give an example of this, we were doing events, right? Events are awesome, but they’re actually pretty hard to scale beyond that say, 200 people. Once you go beyond like a 200 person event, you’ve got to get professional caterers, and you’re not just ordering pizza. You’ve got to-

Joe: Right, you need event insurance probably, a whole bunch of other stuff. Yeah.

Nathan Beckord: [crosstalk 00:41:25]. It’s so much stuff. It gets much harder-

Joe: Yeah.

Nathan Beckord: … once you get larger. Events are hard to scale. You’ve got to hire people to man the door, and all kinds of stuff, right? And so, how do you figure out ways to scale, that aren’t going to break the budget? I think like, I love your show, and we’ve got a show that’s a little in the same vein called How I Raised It. It’s a podcast-

Joe: Nice.

Nathan Beckord: … about how to raise capital, you know? And that’s been scaling, and that’s fun because it’s like, there’s not the limitations that you have with an event. Same content, same audience, but it’s a more scalable type of model, where it’s a podcast versus an event. I think that’s the trade secret is just like, always betting on how can I put my time and money into things that are scalable, basically.

Joe: Awesome, I love that. I will certainly link to that show, and then we could probably get like a little cycle going where you talk to people about how they raised it, and then I … send them over my way, and vise versa.

Nathan Beckord: How you built it, exactly.

Joe: Awesome, awesome. Thank you for the kind words, I really appreciate that. I’m going to link to the podcast, and to But, is there any other place that people can find you?

Nathan Beckord: That’s pretty much it. I mean, we’re moderately active on Twitter, but not very active, and it’s just @FoundersSuite on Twitter. We do have a pretty good YouTube channel, Founders Suite as well. And Facebook, we have a funding hacks group on Facebook. And then-

Joe: Nice.

Nathan Beckord: … Yeah, just the podcast, How I Raised It on the usual places, iTunes, and Spotify, and stuff like that. That’s about it, otherwise

Joe: Fantastic. I will link to those, and everything that we talked about in the show notes over at HowIBuilt.It. Nathan, thanks so much for joining me, I really appreciate it.

Nathan Beckord: Thank you so much for having me, I enjoyed it too. It was a fun chat.

Joe: Thanks so much to Nathan for joining us this week. I love his story, I love that he used his own money to build a minimum viable product, which he needed to get funding, right? I loved that, I loved that he said something that has been echoed since the very first episode of the show, overnight successes are not ever overnight. Then, we talked a little bit about his plans for the future, and his trade secret was trying to figure out things to do for your business to scale and grow is hard, but it’s extremely important. I’m going through this right now. There is a lot I want to accomplish in 2020, including taking my business to the next level, and planning all that is very difficult.

Joe: I said this, this morning as I record this. I said this morning that it’s an art form to be intentional, and I think that gets to the root of what Nathan was saying here. Thanks again for his time. Thanks again to our sponsors as well, they are Ahoy, Cloudways, and Pantheon. Definitely, definitely check them out. If you liked this episode be sure to like and subscribe in Apple Podcasts, or wherever you listen to podcasts.

Joe: Now, as we approach the end of season seven and I’m gearing up for season eight, I have some plans to be more intentional, and I want to hear from you. If there’s a topic that you are interested in, or a question that you have, you can go to HowIBuilt.It/Feedback. It is an extremely simple form, just your email address, and the feedback you have. The email address, just so I can write you back, and maybe get more information. But, I really want to hear from you as I gear up for 2020. Once again, that URL is HowIBuilt.It/Feedback. It will be in the show notes for this episode, which you can find over at HowIBuilt.It/146. Until next time, get out there and build something.

The post Exploring VC Funding with Nathan Beckord appeared first on How I Built It.

Nov 12 2019



Rank #11: Jennifer Bourn and Profitable Project Plan

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Jennifer Bourn is the founder of Bourn Creative and creator of the Profitable Project Plan. She’s also a freelancer who’s doing it right. She has worked out the perfect system to get and manage client projects; in this episode we’re going to talk all about how she built it.

Show Notes

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Intro: Hello everyone and welcome to episode 86 of How I Built It. In today’s episode I talk to Jennifer Bourn, founder of Bourn Creative and creator of the Profitable Project Plan. Jennifer is a freelancer who’s doing it right – she has worked out the perfect system to get and manage client projects, and we’re going to talk all about that came to be. I’m excite to get into it, but first, a word from our sponsors.

Sponsor: Today’s is brought to you by Pantheon and Creator Courses. You’ll hear all about Pantheon later in the show.

Creator Courses is a website dedicated to teaching you how to build on the web. Their catalog of courses is continually growing and it’s becoming the best place to learn how to build specific projects with task-based objectives. You will always learn by doing. Currently, you can learn how the new WordPress editor with their Introduction to Gutenberg course. Head over to, and use BUILDIT at checkout for 40%.

And now…on with the show.

Joe Casabona: Hey, everybody. Welcome to another episode of How I Built It, the podcast that asks, “How did you build that?” Today my guest is Jennifer Bourn. Jennifer, how are you?

Jennifer Bourn: I’m great, thanks.

Joe: Thanks for coming on the show. If you don’t know who Jennifer Bourn is, well, I’ll let her introduce herself, but she is a fantastic person. We’ve met up at multiple WordCamps and I’ve always enjoyed hanging out with her.

So, we’ll be talking about the Profitable Project Plan today. Jennifer, why don’t you tell us who you are and what you do?

Jennifer: My name is Jennifer Bourn and I am founding partner of Bourn Creative, A full-service design and development agency based out of Sacramento, California. We are celebrating our 13th year in business this year, so we’re really excited about that.

I also do a lot of freelance writing and I have my own site, where I am helping designers and developers run profitable businesses without sacrificing their health, their family, or their sanity.

Joe: That is always a good thing to hear, because a lot of freelancers sacrifice some or all of those things in order to make ends meet. I believe the whole idea behind the Profitable Project Plan is that we don’t have to, is that right?

Jennifer: That’s correct.

Joe: I should also include, I forgot to say this in the intro, but aside from all of this stuff that Jennifer Bourn does she also gave me two fantastic recommendations last October. One was how to manage my business, and we’ll probably talk about that a little bit, but the other was for these heated slippers that I subsequently got my wife for Christmas.

Jennifer: They’re the best things ever.

Joe: I just remembered that as you were talking, I’m like, “Well, I have to tell everybody.” I’ll link those in the show notes, because they’re great.

Jennifer: They’re the only shoes I wear all winter long. And Brian has to be like, “We’re going on a date night. Those shoes are not coming.” And then I’m sad, and I think, “Do I really want to go somewhere?”

Joe: Yeah, right? You’re ready to go with your heated slippers. So, I just wanted to include that, but that’s not what we’re here to talk about. We’re here to talk about how to make freelancers more profitable.

So, first of all, you’ve been doing this for 13 years. You are doing very well, it seems. And I’m glad to see the advice being passed on to other people. How did you come up with this idea?

Jennifer: Profitable Project Plan actually wasn’t an idea that I had that I then created, it was born from a need I had in my own business. I’ve been working as a designer for 20 years, but as an agency owner for 13.

I started freelancing, and for the first several years I was on my own and I was doing everything myself. If you’re listening and you’re a freelancer, or you’re in the early years of agency, you know what that’s like.

You’re wearing every single hat in the business, and you’re juggling admin, and the doing of the work you’re being hired to do, and if you focus on doing the work then you’re forgetting to follow up, and maybe you’re not closing some sales that you could have closed if you did better on the admin side, and if you focus on all the sales you run out of time to actually do the work, and then you don’t sleep and you’re cranky, and it’s a mess!

I got to that point in my business, and I’m like, “I can’t do this anymore. I need some help.” And everybody I talk to is like, “Hire a virtual assistant. You need to get an employee.” They’re telling me all these things, and I’m looking at this, and usually at that time you’re also undercharging.

So, I’m at this point in my business and I’m looking at this, and I’m like, “I can’t afford to hire a virtual assistant, or an admin person, or a project manager who’s non billable to absorb all the admin costs.” And I’m looking at virtual assistants or project managers or things that want $75, $85 dollars an hour, and I’m like, “I’m one person. I almost charge that.” Like, how would I even make that work?

It was just one of those things that I was really struggling with, and at the time I saw an ad for some software. It was like, “Double your sales!” And I’m like, “Yeah. Like I have any more hours to work in the day. That’s never going to happen.” And then I saw another ad for the same software that said “Replace an employee!” And I went, “What? What?! Wait.” This is revolutionary to me.

I started thinking about it, and the software was actually for e-mail marketing and things like that, but I focused on “Replace an Employee.” So I created a system in my business to automate every administrative thing I could automate. The communications and the hand-holding, and the education of my clients that was sucking all my time. I built it all into this software to automate it all so I didn’t have to hire somebody, and that software did the job of a full-time admin person for me.

It was amazing because it freed up my time so that I could spend more time on the stuff that really mattered with my clients. Making a really deep connection with my clients, and working on strategy, and the design, and the development, and creating a really amazing product, which is really what they’re paying you for. Not chasing down all the little to-do’s, and the education, and answering 2,500 questions. The system was taking care of that for me.

I started talking about this at WordCamps and at different events, and people would ask, “Can I buy that system from you?” And I would say, “No.” At this point, this is my secret sauce. Like, “No freakin’ way. I’ve spent hundreds of hours refining this. No way!”

But we finally got to a point with Bourn Creative where we’d moved upmarket enough that our clients have changed a little bit, and business is doing so good, and I think as you get older you get to a point in your life where it’s just not all about you anymore.

You start thinking about, like, “I’m pushing 40,” and I’m starting to think, “What kind of legacy do I want to leave, and what kind of impact do I want to have?” I want to be able to help other people, as we’ve been able to enjoy life to the fullest in these years because of the systems we’ve created.

I see people I know that are so talented not taking vacation, and not out there enjoying life. We started talking about it and I thought, “Ok. We’re going to put this out there. I’m going to package it up and sell it as a Profitable Project Plan, because I want to help other people enjoy their business more but enjoy life at the same time.”

Joe: Man that is– Well, there’s a lot of great stuff to unpack there. I mean, I’ve been freelancing for 15 years, more or less, full-time and not full-time. You get to a point where you have a finite amount of hours, but you don’t want to make a finite amount of money.

And so you need to fundamentally change something if you want to go to the next level, otherwise you might as well just work for somebody else. I mean, that’s the truth of the matter. And like you said, I think I’m making that move as well.

I want to move into products and teach people the stuff that I know, because it’s becoming more enjoyable for me. I’ve been teaching since college and I want to, not pass the torch, per-say. But I want to help people enjoy the things that I got to enjoy since high school, essentially.

So, the Profitable Project Plan– I will get that by the end of this show– is something that you built out of a need for yourself. That’s a common story on this podcast, and I’m sure with a lot of business owners. They find a need and they fill that need for themselves and they realize, “Hey, other people have this need.”

You also mentioned that you saw an ad for a system to replace an employee. Did you do other research when coming up with this plan? Is that software still integrated into your plan?

Jennifer: That’s a good question. The software at the time, it was late 2008 and it was Infusionsoft when they were brand stinkin’ new. I went to an all day event in February of 2009, I bought it and I implemented it right away. We used Infusionsoft to run Profitable Project Plan for years, but their engineering wasn’t keeping up with other third party products.

With the ability to integrate different products with each other, we started at one point evaluating, “Do we go with a mediocre all-in-one that isn’t really progressing with their engineering? Or do we ditch it, and we go with other options that are the best at what they do and then integrate it all together?” So we chose to do that in the late 2013, 2014-ish. Partly because my husband had cancer and we didn’t know.

Joe: I didn’t know that.

Jennifer: Brian had gallbladder cancer. And at the time, the mortality rate on that is like, once they find out you have gallbladder cancer you’re basically dead. But he was the silver bullet that they found early enough that it was OK, but at the time we didn’t know what our life would look like, or how much he’d be able to work.

So we were looking at trimming expenses like crazy and that was one of the decisions that helped us push that, because we were paying hundreds and hundreds of dollars a month for Infusionsoft. Then we moved over to other things that maybe total $100 bucks a month, and they do the exact same thing for us.

Sometimes making more money isn’t about pushing and making more sales, sometimes it’s about changing up what your expenses look like.

Joe: Yeah, absolutely. I mean, I just celebrated about a year of going out on my own, at the time of this recording, full-time. That was the first thing I did, I was like, “What am I paying for that I definitely don’t need?” And it’s like a double sided coin, or two sides of the same coin, maybe. “What can I pay for that will definitely make my job easier?”

I think so far this conversation has been, “How do we balance that?” Because you are willing to pay for software that will replace an employee, but you’re also not willing to just frivolously spend money to do that.

Jennifer: Exactly. I think that’s something to look at, is we made that decision to trim those expenses when our life was up in the air and we didn’t know what it would look like. But once he got the medical All-Clear and he was fine and we were ready to go, it’s not like we went back to all of a sudden, “Let’s buy all this software!”

It was like, “Wow, look! We can get by on so much less, we have two options now. We can either work less because we know the amount of money we need to make is less, and we can spend more time playing and having fun and enjoying life. Or, if we work more then we just make more, but we don’t have more time.” So, we chose the first.

Profitable Project Plan supports us in that, in that it’s a complete client management system, from sales call to post website launch follow-up.

Joe: Wow, that’s fantastic. Now we’re moving to the title question, which is, “How did you build it?” It’s interesting because I naturally don’t want you to give away the secret sauce, I want people to check out and buy by the Profitable Project Plan.

Maybe we can talk in generalities, how you made it to this point where you knew how to manage your business. Does that makes sense?

Jennifer: Sure.

Joe: Cool.

Jennifer: We’ll start with implementing Profitable Project Plan. All of the content for the course already existed because it’s the content I use in my own business every day. What I had a frustration with over many years of taking online courses, and enrolling in business coaching programs, and all of these things.

People would tell you all the success they had, but then give you a different version of it. You’d get some like, public, glossy version, but not the version they’re using behind the scenes. And it always drove me crazy. So I said, “If I ever am going to do this myself you’re going to get– everything that I use, you’re going to get what I use, no holds barred. The same thing.”

Profitable Project Plan includes the e-mails, the client education guides, the scripts. Everything that I use to work with my clients is included in that. So, we didn’t have to do a ton to develop content, but in terms of actually delivering the course obviously we use WordPress. We deliver it through MemberPress with Delightful Downloads, and we run Stripe as our payment, and AffiliateWP for our affiliate program. It’s really just that simple.

Joe: Nice. So, MemberPress, we did have Blair Williams on the show, I’ll make sure to link that in the show notes if you want to learn how that was built. Delightful Downloads is not something I’ve heard of before. Can you tell us a little bit about that?

Jennifer: Delightful Downloads assigns any downloadable media to a membership level. So, let’s say somebody in your program is like, “I’m going to send this link to this PDF to a friend of mine.” If they’re not logged in under that membership level, the link doesn’t work. You can only download it if you’re logged in at the approved membership level that you set.

It’s just a way to manage your downloads in the back-end, for your membership courses, or online courses, or anything like that.

Joe: Very cool. I’m definitely going to check that one out, because that sounds excellent. AffiliateWP, big fan of that one, Pippin has also been on the show. Then Stripe for payment, naturally. Because Stripe is the best.

Jennifer: Yeah, and to record all my videos I used Zoom Webinars, and then ScreenFlow to edit them all and get them all pushed up to my membership site.

Joe: Nice. I’m going to link to one of your blog posts about your whole set up. I read that, I loved it, I bought a bunch of stuff. Like that [gorilla case] thing?

Jennifer: Oh, yeah.

Joe: My recording area looks so much better because of that.

Jennifer: It’s so pretty back here.

Joe: Instead of a mess of wires, now everything looks great, everything is on its own power strip like you said. So, yeah. Definitely will link to that blog post as well.

You said that you use Zoom Webinars, are these live with the members?

Jennifer: Yes, I do. Profitable Project Plan is my flagship course, we run it twice a year and we run it live. It’s 12 weeks long, nine training sessions and three implementation weeks in case you missed something. You forgot to watch it one week, you got busy, you need to catch up or you’re trying to implement and you don’t want to fall behind.

The lessons are delivered live and there’s live Q and A every week. If you’ve got questions about contracts, or the sales call, or whatever we’re working on that week, there’s live Q and A so you can get your question answered while you’re taking action and getting things done.

The mini-courses that I’m working on, which I’ve launched one, and that’s Positioning E-Commerce Projects for Success, those are evergreen. Those are pre-recorded, you take it, you go, you’re done. Profitable Project Plan is live.

We kicked around the idea of doing an evergreen course, but all the feedback from students so far have been that they really like the interaction of live and being able to ask questions on the spot and exactly what we’re talking about. It doesn’t mean I won’t ever go evergreen, and mix in live Q and A’s, but right now we’re delivering the course live and I really like it that way.

Sponsor: This episode is brought to you by Pantheon. WordPress 5.0 and the new editor, Gutenberg, are coming. Are you prepared? Do you want to learn about the changes in advance? Pantheon has gathered resources to help you prepare including webinars and tutorials. Pantheon has also made it easy and free to try Gutenberg with your site before the official launch. Visit Let them how How I Built It sent you!

Joe: That’s great. First of all, it’s hugely valuable for the students. There are certain things that work well as evergreen, as you’ve pointed out, you’re doing evergreen stuff. My course on How to use Gutenberg is evergreen and most people like it that way. My forums for that course are dead because I answer all of the questions in the course. basically.

I also ran a coaching program about a year ago where live in-person was hugely valuable, because I would tell them something and then I’d get questions. I’m sure it’s also hugely valuable for you too, because now you’re hearing questions in real-time, what people are thinking about, you could probably see your students, maybe. Do they have their webcams on?

Jennifer: Not in webinars.

Joe: Gotcha, ok. I know that was always something that I appreciated in the classroom, is I could see student’s faces and tell when they’re confused. But the fact that they can ask questions as you’re talking is good feedback, so that’s very cool.

Jennifer: It’s nice because we can take those questions and roll it into the content for the next time, so we can answer those questions in advance. It actually goes on sale again very shortly, the next version of Profitable Project Plan starts August 7th. And we’ve rolled in questions that clients and our students have asked in the past sessions.

We’ve rolled in suggestions that they’ve made like, “You know that would be super awesome? If you could do this.” And sometimes it’s like, ‘No. There’s no way we’re doing that. That’s not even part of this course.” And sometimes it’s like, “That’s a really good idea. I can definitely do that.” So each time we run it we’re just continuing to improve.

Joe: Nice. That’s fantastic. I have one more question about that, because this is something that I usually struggle with, is I’m sure you have a at least somewhat global audience. If not, you at least have people in different time zones. How do you choose? Do you just say, “We’re recording at this time, this works best for me. If you can attend live, great. Otherwise you can hit the videos.” Or do you pick a time by committee?

Jennifer: It is the time before they pay. On the sales page you can get the schedule, and you know the time. So, if it works for you great, if it doesn’t work for you and you’re okay watching the recordings, you know that in advance before you enroll, before you sign up, before you pay.

I always hold my live classes on Tuesdays at noon. Noon Pacific time, 3:00 p.m. Eastern. For those in Australia it’s the afternoon. It seems to be that seems to be the most versatile time for most people. There’s just a few time zones where they’re like, “This is the middle of the night. I’ll watch the recording.” I also have a Facebook group connected with it too, so they can watch the recording and then pop questions in the Facebook group, and I can answer them there for them as well.

I’m a big fan, if you’re going to have a set time for your course, stick it on the sales page and let people know before they even get started. So if they aren’t available to do it live, then they can make that choice on whether or not the recordings is going to be right for them.

Joe: Great. That is excellent advice, I am going to write that down. I’m going to take that advice if and when I do another live thing. That’s fantastic.

We are getting close to time here, and there are a couple more questions I usually like to ask. The transformations– this is relatively new, launched with the last year?

Jennifer: I ran the first beta in summer of 2017.

Joe: Ok, cool.

Jennifer: This will be the third full course, the fourth if you count the beta.

Joe: Gotcha. Have you seen major transformations since you launched?

Jennifer: Transformations of the course itself.

Joe: Yeah, any big changes, or something you’re like, “I’m definitely going to do this for the first one,” and it didn’t really work in the beta, so you changed it.

Jennifer: In the first one, I just was like, “This date to this date works for me,” and I didn’t really put a lot of thinking into the how it would overlap with our vacations. I definitely learned over time, now we definitely assess our vacations. The last version of Profitable Project Plan I timed it so the Q and A weeks, the implementation weeks, were weeks that we were gone and traveling.

Because I can answer Q and A from the road. I did one from the hotel parking lot in Holbrook, Arizona when we were going to Petrified Forest National Park. Because when you’re not leading a training, and you’re just answering questions, there’s less pressure there.

I’ve definitely learned a little bit about scheduling, and the course itself has transformed a little bit, in that the first time I ran it, it was all talking head. It was me talking and teaching. Each time I run it I have been adding more slides, more examples, more things like that. I think to just switch it up visually a little bit, and provide some more interest so it’s just not my talking head all the time.

The course itself in terms of content is pretty rock solid. Each time we run it I take the advice, I always do a survey at the end and I look at, “Where can I improve and make this even better?” I never think that you should rest on your laurels and think, “This is good enough. I ran it once, I’m just going to run it over, and over, and over, and over.”

I think every time you run it you’ve got to look at, “How can I add some value to this?” Your students are the best place to figure that out, because they’re going to tell you, “You know what would be great? If you could add this.” Some of their suggestions are going to be really good and aren’t going to take you much time.

Joe: That’s great advice. That’s a recurring theme among the proper online teachers, I’ll say. Is that courses should not be passive income, because people are constantly learning from you. So I really, really like that. Are there any plans that you could share for the future of the Profitable Project Plan? The course, any evergreen courses or whatever?

Jennifer: We’re kicking around the idea of making the core content of Profitable Project Plan evergreen, and then doing a weekly live call so that people can join when it’s right for them. Right now, because we only run it two times a year, when sales close it’s a waiting list. We’ve got hundreds of people on a waiting list that are like, “When is this going to go for sale again?” And when I put it for sale, may not be when they’re ready, or financially when it works best for them, right?

I’m always of the opinion, “Make it as easy as possible for people to do business with you.” Make it as easy as possible for clients to say, “Yes.” And that goes for memberships and courses as well. So, we’re kicking around the idea of maybe turning that part of it, still doing live, but part of it evergreen. So that students can invest when it works best for them and not necessarily just when it works best for me.

Joe: Great. That sounds fantastic, we’ll definitely keep an eye on that. You mentioned that August 7th is the next time it goes on sale. So, I’ll make sure to–

Jennifer: It starts.

Joe: It starts.

Jennifer: Yes.

Joe: It starts August 7th, ok.

Jennifer: Yes.

Joe: Gotcha. I’ll make sure to have this out before enrollment closes, then. Because we want people to take it after hearing about how great it is.

Jennifer: Me also!

Joe: So, as we come up on our half hour, we’re doing great on time. I like to ask this question of all of my guests. Do you have any trade secrets for us?

Jennifer: That is a really, really good question. I think the biggest secret that’s really not a secret, is that it doesn’t have to be perfect to launch. I think there are a lot of people that have ideas on courses, and ideas of things that they want to create, and they want to do, and they never do it because it’s never everything they’ve ever dreamed of ever wanting it to be and totally perfect.

When I had the idea of doing Profitable Project Plan, I gathered up all the content that I created for my business and I ran a beta super cheap. I didn’t do it for free, because I don’t believe in giving away your sauce for free. But I ran a super cheap discounted beta, I got 40 people in that beta, and I ran it, and I just tested it the first time. They did a survey, and I got great feedback and improved it. And the second time, I did a survey and got great feedback and improved it.

That process has worked so well, that when I created the mini course of Positioning E-Commerce Products for Success, when I had that content originally I offered it as a bonus to my Profitable Project Plan students as a “Thank-you.” A surprise bonus at the end of the course. They got that free training if they filled out the survey and provided me a great testimonial.

I didn’t say great testimonial, I said, “Provided me honest feedback,” but luckily all their honest feedback was super awesome and I got great testimonials out of it. But I said, “If you fill out this survey and give me your honest feedback, I’d love to gift you with this free training.” I delivered the Positioning E-Commerce Training, and I recorded it, I sent it to, had a transcribed, and then that transcription became the base of the course that I created. Once I had the actual course created, then I sent an e-mail out to my list and I said, “I’m looking for beta testers.”

“If you want to take this course for free, e-mail me back.” I do that for my list as a thank you for being on my list. You’re gifting me with the opportunity to show up in your inbox, when I beta test stuff, you’re going to be the only people I ask. So, several people responded. I ran the course one more time to test it out with them in a beta, and they got to take the course for free. They filled out a survey, so I got to launch that course and that sales page from day one with some great testimonials, and I got to work out any of the kinks in that content before it actually went public.

So, you don’t have to wait until it’s perfect to get started. Do a beta, do a free training or a webinar, something to work out some of those content details, and then just keep making it better every single time that you do it.

Joe: Great advice. Absolutely great advice. I can’t add to it, so I’m just going to ask, where can people find you?

Jennifer: You can find me at That’s probably the best place that links to all my things.

Joe: Perfect. Jennifer Bourn, thanks so much for joining me today, I really appreciate it.

Jennifer: Thank you, this was fun!

Outro: I would encourage anyone who freelances to take a look at the Profitable Project Plan – not only to you get a great online course and resources – you get face time with the instructor, who’s fantastic.

And Thanks again to our sponsors Pantheon and Creator Courses. Definitely check them out. Both are teaching you all about Gutenberg and WordPress 5.0.

For all of the show notes, head over to If you like the show, head over to Apple Podcasts and leaving us a rating and review. It helps people discover us! You can also join the Facebook community over at I want to build a strong community for this podcast, and Facebook is the place to do it.

Thanks for joining me, and until next time, get out there and build something!

The post Jennifer Bourn and Profitable Project Plan appeared first on How I Built It.

Jul 24 2018



Rank #12: Sam Brodie & Selling Your Business

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Before Sam Brodie founded OffSprout, he successfully sold a niched business that focused on websites for lawyers. Sam generously shares his advice and experience with us, from niching down to how to properly keep your books. There’s tons of great advice in this episode, so make sure to listen to the whole thing!

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Apr 02 2019



Rank #13: Episode 30: Andy Stitt & WordPress for Non-Profits

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In this episode, Andy and I discuss some of the specific challenges and rewards of developing WordPress sites for non-profits, why empathy is so important, and why you should never say never when choosing the right tool for the job.

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The post Episode 30: Andy Stitt & WordPress for Non-Profits appeared first on How I Built It.

Apr 04 2017



Rank #14: Daniel Espinoza and Wearing Many Hats

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Daniel Espinoza is a man who wears many hats: agency owner, product seller, family man, and more. In the episode we get into how he manages keeping everything running smoothly. This is a fantastic conversation for anyone who wants to diversify what they do, without getting too overwhelmed.

Show Notes

Question of the week: Why haven’t you launched your plugin? Let me know on Twitter @jcasabona or Discuss with others over on the Facebook Group!

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Intro: Hey, everybody. Welcome to episode 103 of How I Built It. Today I’m talking to Daniel Espinoza, and he does a whole lot of stuff. He creates in depth and big e-commerce websites for clients, he sells his own plugins, and a lot more. He’s also a family man, which we’ll talk about. I appreciate all of the advice that Daniel was able to give us in this episode. He talks about things like building a lifestyle business, which is something that I’m trying to do. I want to balance life and family and running my own business, and I don’t want to be married to my job. I’m trying to build a business that supports the life I want to lead, and he talks a lot about that too. He also offers good advice about launching and a whole bunch of other things, so again I’m excited about this episode. I’m glad that Daniel was able to give me some of his time and advice because we are in– He’s maybe a couple of years ahead of the current situation that I’m in, and to look into the future a little bit was valuable for me.

We’ll get into all of that in a minute, and I do want to tell you that this episode is sponsored by Pantheon and by Creator Courses. On the day this episode comes out, we are looking at about a week until WordPress 5.0 and Gutenberg, so maybe it’s already out as you listen to this. There’s a lot of concern around what that means for developers and for our clients, and how we need to handle upgrades. I have a lot of courses available around that subject. I have a course that shows you how to use Gutenberg if you’re a user and you’re curious how the interface is going to change, and that’s very affordable. If you’re a freelancer I include that course in my Gutenberg for Freelancers course, but you will also learn how to work with your clients and create an upgrade plan and communicate these changes to them, so there’s that too. If you’re a theme developer, there’s a theming for Gutenberg course that I developed with my friend Zach Gordon. You can find all of those over at, and you can get a special discount by using the coupon code BUILDIT at checkout. Go ahead and check those out over at You’ll hear about Pantheon later on in the show. For now, let’s get started.

Joe Casabona: Daniel, how are you today?

Daniel Espinoza: I’m doing a great, Joe. I’m doing great. Thanks for asking.

Joe: Awesome. Thanks for coming on the show. Daniel and I, we hung out around each other. We have similar circles, and we got in touch because I was checking out one of his plugins, and then we got to talking about building a lifestyle business. That’s what we’re talking about today.

Daniel: Definitely.

Joe: Nice. Why don’t we start off with a little bit about who you are and what you do?

Daniel: Great. My name is Daniel Espinoza, and I work online mostly in the WooCommerce space. I have two businesses, and one is Grow Development which is a WooCommerce agency that focuses on mostly recently subscription sites. I help large subscription sites fine-tune their business, making sure that the subscriptions happen correctly and on time. They can do reporting, and they can add functionality, the wheels keep turning on these large subscription businesses. I also support all of ConvertKit’s WordPress plugins, so they’re another big client. I also have a more traditional WordPress plugin marketplace that came out of a previous life of being a WooThemes employee, and a plugin developer since before WooCommerce was WooCommerce.

I built for Jigoshop back in the day, and we went through that transition of becoming WooCommerce, and building plugins, and when AD had his Summer of Code where they wanted to get as many plugins written for a fledgling WooCommerce as possible, I helped, and I built like four or five payment gateways that summer. So from that, now I’m focusing on store owners who do subscriptions and helping them with their challenges. But the many hats is a real thing, and I have an inside joke with some Slack buddies of mine that I’m constantly switching hats throughout the day. From support tickets to a client meeting to writing code to figuring out what’s next for the agency, to doing marketing and making videos and blog posts. It’s fun. All of it is interesting work, and I do it from a spare bedroom in my house. It’s stuff that I’ve chosen to do, and I like doing.

Joe: That’s fantastic. We were talking a little bit before we started recording about the reasons why you decided to get into this line of work, and you mentioned Start with Why, which is one of my favorite books. It’s excellent, and I’ll link it in the show notes. It’s one I often recommend. Can you maybe talk about how reading that book changed your perspective on running a business? I know that’s a very Terry Gross NPR question, but it’s a good one to ask.

Daniel: Definitely. I read the book in 2014 or 2015, and I started my business– Before working online, I worked at a bank in an IT department. Khakis and business casual and cubicles. Then my wife had our first child, and she started staying home to care for our daughter, and that’s around the time in the late 2000s when Freelance Switch was going on and the four-hour work week came out, and ThemeForest was getting started. A lot of talk was happening about becoming a freelancer, so I thought “I can code. I can do this,” and I threw a couple of opportune meetings. I got a first client and then I quit my job, full of stars and dollar signs in my eyes and this was 2018. What else happened in 2018? Excuse me, in 2008.

That was the market crash of real estate and stuff. But I survived that, it was fine. When I read Start with Why it fine-tuned the reason and brought back the reason that I had started working for myself, and it was that I didn’t want to be stuck at a code deployment for a bank over a weekend. Literally staying there 24 hours, because these are ATMs that you’re deploying code to. I didn’t want to be stuck there if it wasn’t my choice just because I was an ancillary part of this large team, and I wanted to be with my family. I wanted to be with people I love and doing things that I  like, so enabling this lifestyle of freedom of location and freedom of choice, just freedom of choosing things that I want to do as opposed to having them put on me.

That’s what it was all about and my why, I succinctly put into a sentence in a blog post was, “My Why is to run a business that allows me to spend as much time with my family, traveling the world, and doing work that I love.” I’ve reached that point and gotten to do cool things online, hang out with my family, my kids are, and that’s a decision that came from wanting to travel. We haven’t traveled a lot in the last couple of years, but we’ve kept that decision because it fits the Why also. We don’t want to wake up at 6 AM to an alarm clock to get the kids to school. We love teaching them and doing homeschool-type stuff. The businesses are what help that to happen. They pay the checks, and they write the checks for our lifestyle.

Joe: That’s fantastic. You and I have similar reasoning, because I was working in an agency before I went out on my own about a year or so ago and the birth of my daughter was the impetus of that. The agency life was a good single lifestyle because I loved staying up super late and writing code and things like that. But now I want to spend time with my kid.

Daniel: They’re cute, right? You don’t want to leave them.

Joe: Exactly. I’m fortunate, much like you, that we have a babysitter who is here. I work from home so at lunchtime or if I’m not doing anything I’ll go downstairs and say hi to the kiddo and spend a few minutes with her. Very fortunate in that sense. But I also  that reasoning because a lot of people start a business thinking, “This is the best way to get rich.” Perhaps it is. We talk about the hockey stick growth, where it’s low, low, low, and then high but I don’t have any delusions of grandeur that I’m going to be a multimillionaire because I’m not working sixteen hours. I’m not doing the Gary V lifestyle. I’m working the eight to ten hours a day and then spending as much time as I can with my family. So I love that, and I just wanted you to say it on the show.

Daniel: Yeah, totally.

Joe: You also mentioned you’ve niched down to subscription sites, and you manage these plugins.

Daniel: Right.

Joe: I always like to ask, what research did you do in either developing a plugin or making the decision? I want to target that at your decision to do subscription sites because I know that there’s a lot of moving parts to subscription sites and it’s incredibly important to have somebody who understands them well. So, what was your decision-making process with that?

Daniel: The four year ago time, when you and I were networking around each other. I haven’t been to a WordCamp in over a year. The last one was local San Antonio, maybe 18 months ago I went to Atlanta. But I’ve stopped doing that, previously I was traveling for a lot of WordCamps and going to events that– What was it? The WooConferences and–

Joe: WooCon, PressNomics–

Daniel: PressNomics, thank you. Gosh. Totally blanked out on that. Through that, I met a lot of great people, and I don’t look down on doing that. It’s a great way to build your network and connect with people that are fun and building this WordPress economy. But I backed off on that, so through that, I got a lot of referrals for WordPress work and for WooCommerce work, for building plugins and for building sites. I don’t do themes because I’m not a front-end guy, and I’m okay with that in my soul. I have come to terms with that. But the projects, they chose me. The projects that kept coming back were these subscription sites. Understanding the ins and outs of the WooCommerce subscriptions plugin built by ProsPress. That code base is a level of difficulty or a level of challenge that is above and beyond a normal WooCommerce site. It’s a whole ecosystem unto itself, on top of WooCommerce on top of WordPress.

So being able to say, “I can do what you’re looking for, doing custom scheduling or whatever the business is wanting. I can do that fairly quickly for a good price.” People like that, and subscriptions folks, they have the holy grail of recurring revenue, and they can forecast out months of what their money will be. They have more money and more wiggle room to keep someone, a developer like myself or an agency on staff to handle the problems that they’re having. It’s not a one and done type project. I liked that aspect, and I like building the relationship with the store owner because they get to go off and focus on their product, they get to focus on their marketing, and we keep the site running smoothly. When they come to us, and they’re like, “OK. We’re ready to add a wish list functionality,” or, “We’re ready to add a refer a friend functionality.” I can say, “OK here’s our options on the pre-built plugin landscape, and then here’s if we put some custom code in. This is what it will look like.” Then they make their choice and boom we’re off. It’s a different dynamic than someone coming in the door and saying, “I want this site built.” And they have a price built in their head that they’re looking for, that $10  an hour type of thing.

Then educating that person into a project, and then serving them through the project and then trying to do a follow-up. It’s a whole different thing. We have we have a weekly call with the site owner, and we have ongoing conversations. They mentioned something we take note of, and a month later we’ll bring it back, and they’ll say, “I did want to work on that. We have a lull in other things, let’s work on that project now.”  It’s an ongoing relationship, and it suits my personality well to have those instead of the revolving door of projects, and so when I said “It chose me,” it was just that I had a couple of these and now this is what I look for. We have several sites that we serve, and I know who they are and what their business model looks like, so if somebody comes in looking for a theme, I say, “I’m glad you came. It’s nice to meet you, but you’re going to be better served going over here.”

Break: Today’s episode is brought to you by Pantheon. WordPress 5.0 and the new editor Gutenberg are coming. Are you prepared? Do you want to learn about the changes in advance? Pantheon has gathered resources to help you prepare, including webinars and tutorials. Pantheon also has made it easy and free to try Gutenberg with your site before the official launch. Visit Let them know that How I Built, It sent you. Now, back to the show.

Joe: Something you said about the $10 an hour website, people running subscription sites can immediately see the value in your work.

Daniel: Definitely.

Joe: If I’m making a brochure site for somebody, it’s hard to attach direct dollars to a brochure site. Because how many people are going to use the contact form, and then how many of those people are going to become paying customers? “You built me a subscription thing, and now I’m making even $1,000 in monthly recurring revenue. Great. I  now know how valuable you are to me. You’re at least $12,000 a year valuable.”

Daniel: If our fees are a percentage of that, we can say  “With a current site we have, our fees I can see are less than 10% of their monthly revenues. So I can say, “For the same fee structure we can grow your monthly revenue so that we can become an even smaller percentage and a smaller expense for your company, and build on top of that. We know we know how we built your site. We know where the problem points are. We can optimize your checkout, and we can speed up certain pages, we can fix your subscription renewals to run faster and take up less processing. Doing all of these things comes from an intimate knowledge of the site and the code, and how it’s built.

Joe: That’s brilliant. On that same token, mentioning percentages and stuff like that. I’ve quoted out e-commerce website, and somebody was  like “We’re going to have thirty thousand products on the website.” It was just pulling stuff from various APIs, and I quoted him at $20,000 or something. And he was like, “That’s a lot of money,” and I’m like, “That’s less than $1 a product. That’s like $1.50, or $0.75 a product or something like that.”

Daniel: What’s funny about that, I was going through my email from a decade ago when I started out, and I started out building e-commerce sites. My email had hit the threshold. It was at 80%, so I was like “This is ridiculous. Let me remove– What is taking up this space?”  I did a search for anything over five meg and back in 2008, 2009, 2010 I was getting emailed these Photoshop files for these e-commerce sites that I was building out a theme for. I had this string of emails of this site’s PSD, this site PSD. I was talking to my wife, and I was like, “I have so many of these files.” And she said, “Are any of those sites still online?” And I said, “I don’t think they are.”

And I searched for a couple, and they’re definitely online. So that’s also the difference, I felt bad. So much money and effort was put into the design of this site before it launched, and then it launched. Then how much effort was put into the building the customer base? The marketing, the long-term sustainability of the business? I grieved a little bit for that. I am sorry that they didn’t make it. But my customers now have revenue, they have a marketing plan, they have product-market fit, and they have all those buzzwords. They’re making money. I’m glad to be a part of that and help push that along and make it even bigger for them.

Joe: That’s fantastic. I’m enjoying this line of thinking. I didn’t prep you for this, but for the title question of how did you build it, maybe we could talk about things that you need to think about when building a subscription site. Would that be cool?

Daniel: Definitely.

Joe: Awesome. Let’s take a random subscription site. How did you build it?

Daniel: The stack that I mentioned, the WordPress WooCommerce, WooCommerce Subscriptions. The cost is only for WooCommerce Subscriptions on the plugin inside, just straight out of the box you can set that up. WooCommerce Subscriptions is maybe $199 for a year license. You can set that up, put a product on there that will recur monthly for whatever cost. $25, $50, $49 or whatever, and then start marketing that day one. If it’s access to a membership site or to a newsletter or something like that, that’s all it takes, and you’re in the door. After that then you can start, if you’re shipping a product then you have costs with fulfillment and actual production and cost of goods, then that goes from there. But having a website that will handle subscriptions for you, it’s a low barrier to entry.

Joe: Nice. Are there any particular themes that you like to work with, or are they generally custom developed themes?

Daniel: They are usually a child theme of Storefront which is built by the WooCommerce team. I have a couple of custom built themes, I would advise against custom built themes because they’re pain for future developers to maintain. On my sites, I use Array Themes, and then Storefront for other stuff. Shop Plugins, we’re switching. We started with a ThemeForest theme from Astoundify, and then we’re switching over to Array Themes checkout because it works well, the EDD. Yes, we are a WooCommerce plugin developer selling on EDD, which may sound funny but when we started Shop Plugins in 2014, it was the best solution for handling software licenses and a lot of the stuff that freemium and  Freemius and some of the other solutions that exist now that didn’t exist back then. EDD’s still going strong, so we’re glad to be– And we sold EDD plugins previously in a previous life, but it is still going strong, and that’s what we built that site with.

Joe: Nice. I’m a big fan of the folks over at EDD, and I just interviewed Vova Feldman recently about Freemius.

Daniel: It’s a great product. I built it into a plugin for a client, and it works well, and all the features. He can focus on adding features to that integration, and it’s taking off.

Joe: Absolutely. I’m thinking about selling a few of my own plugins, and I’m seriously considering Freemius because that’s not the main focus of my business, building online courses is. I would much rather– I’m happy to give them a higher percentage if I don’t have to worry about anything.

Daniel: That’s true.

Joe: Developers can easily fall into the trap of, “I can build this, so I’m going to build it myself.” But  I’ve matured in the last few years, maybe having a kid has helped. I don’t have time to do all of this stuff all the time.

Daniel: That’s right.

Joe: The other question I wanted to ask about the subscriptions, and this is a question that I personally get a lot when I’m coaching freelancers or something like that, is who pays for the WooCommerce subscriptions plugin? Do you have your client do that, or do you pay for it and then pass on the cost to them?

Daniel: The client pays for everything. They handle it, and it’s just a business expense for them. has a great feature where you can add another email address as a developer or an advocate or something, so when I log into, I have a little dropdown that has all my clients in there. I can switch over to their account and pull new versions because we don’t do automatic updates on sites, we have a workflow for pushing updates. I can pull new versions of code there as that customer. That’s a great feature for managing multiple client’s downloads. They pay for the license, but I get access.

Joe: That’s truly fantastic because I’ve certainly run into that. I had a client recently who was the designer for the site. So I was two people removed from the client, and he’s like “Can’t I just use your license?” I’m like, “No you cannot.”

Daniel: Because you’re going to forget it’s out there, and then following up. I inherited this site, or I had a customer come to me who was, but they were hurting, several of the things didn’t work on the site. It was a digital downloads type marketplace, and they’re still with me. In September I rebuilt their whole Amazon AWS site in Elastic Beanstalk, and it’s humming now. It’s running great. But we had to track down all of the licenses that the developer had, and they weren’t on a great relationship because there is outstanding payment and promises that weren’t kept, and all that. They ended up– They didn’t care. They wanted to move forward, they just cut clean, and then I had them repurchase what we needed through WooCommerce and give me access. I always tell them, “You own everything. It’s your AWS account. It’s your licenses. It’s your MailChimp account,” or whatever. I’m integrating, and then I leave. I have a document that lists what integrations are on it, but you have all the keys to the kingdom. It’s your site.

Joe: Absolutely. That’s why I said, “My God if I disappear one day then you’re out of luck. What if the client decides they don’t want this anymore but don’t tell anybody?” It’s better for the client to own things. On that same token,  I want to get philosophical again, which is not characteristic of me on the show. But you mentioned that we’re talking about having the clients buy all of the licenses, and generally they’re going to have one site, but a lot of the licensing for plugins and you sell plugins maybe your licensing is the same way. It’s based on the number of sites used, where it’s one site, five site, unlimited sites. How do you feel about that pricing? Do you think we’re evolving out of that type of pricing because more people are encouraging the clients? Or do you think that the developer license is still a  valuable thing for a lot of people?

Daniel: A developer license is valuable. On Shop Plugins I don’t have the feature of sharing licenses with your developer. If someone bought a plugin on Shop Plugins and they wanted to share it with a developer, they’d have to share credentials, login information. We don’t get a lot of requests for that feature, so we’re not going to build it. But we get a lot of purchases for, we have a one site license which might be $49, and then we have a two to five site license that is made possible through the software licenses plugin from EDD. We implemented it, which it’s a certain percentage higher than like 89. Maybe it’s not twice as much, but it’s a little bit less and incentivizes buying the higher price point and getting the extra licenses. A lot of clients, or excuse me, a lot of customers buying plugins who are agencies.

I don’t know what the numbers are off the top of my head, but they are using it on multiple sites. There definitely is a use case for that, and they’re matching that plugin on multiple projects. It’s up to them. It’s on them to maintain those licenses. I have had some support requests come in saying “I inherited this site. We think we have a license, but we’re not sure.” And I’ll do some searching and find the site and find the old invoice and say, “It was this person. Can you tell me their name?” And they’re like, “Yeah. It’s this person,  this designer who previously worked on it.” I can line it up, and I’m small enough to where I can do that type of legwork and then grant them the rest of that license. Or they buy another one, and they’re OK with that.

Break: Today’s episode is brought to you by Pantheon. WordPress 5.0 and the new editor Gutenberg are coming. Are you prepared? Do you want to learn about the changes in advance? Pantheon has gathered resources to help you prepare, including webinars and tutorials. Pantheon also has made it easy and free to try Gutenberg with your site before the official launch. Visit Let them know that How I Built, It sent you. Now, back to the show.

Joe: As we’re approaching the end of the show here, I do want to ask about the line that you’re straddling. We mentioned that you wear a lot of hats, and one thing that– The biggest barrier for me personally entering into the plugin product market is the fear of, “I’m just going to get slammed with support requests all the time.” How do you how do you manage that? You do seemingly very high level, and you have some high profile clients here. How do you manage that with managing your Shop Plugins website?

Daniel: Lately I’ve come to grips. Again, a little bit of reflection time. Come to grips with Shop Plugins is a side business. Just straight up revenue, Grow Development is the main focus with time. Dave Ramsey or other money people have talked about, “If you want to know where your priorities are look at your checkbook.” My priority with what’s paying me and what’s supporting our family is Grow Development. Shop Plugins is doing OK. It still makes money every month, and it’s still growing, but it gets a little a small percentage of my time because it is a side business. Having said that, this past couple months I’ve integrated my contractor team of developers into building stuff for Shop Plugins. One of the plugins we just launched was built 90% by one of my contractors. He would write code, and I’d review, we’d have a workflow going. I’d do design, and he would integrate that, and then we launched.

That has been different in that it’s a Shop Plugin plugin, but it’s built by a team, instead of one person. The original question of, how to straddle that, it gets the time it needs. If you launch a plugin and you’re inundated by support requests, that’s a good thing. Because what’s the worst thing that is going to happen? They want a refund. I just gave a refund right before we got on air. It’s not that big of a deal. Get over it. There will be another customer. And if you refund somebody, things don’t work out, and you’re in your– We have a 14-day return policy. We used to have 30 for the longest time, but 14 days is enough time to install it and see if it works for you. I don’t have people usually request after the window. They were inside of the window. They’ve tried it, and it didn’t work. It was our PDF watermark plugin. They were trying to do some type of secure PDF that our plugin couldn’t watermark. I was like, “No problem. You’re on a tight deadline. I don’t have time to look into this today. I’m going to go ahead and refund you. Thanks for being a customer, hope to see you again.” They might come back, and they might not. It’s not that big of a deal. But I’m not going to sink in a lot of time looking into this specific secure PDF format because it’s the only person that has asked me about it. If I get ten more, then that’s a big blinking light that maybe we should fix.

But mostly we don’t get slammed with support requests. Maybe a couple a day. Those are enough to be handled in the Slack time after because I have one client that takes up pretty much all of my daytime hours. Like you were mentioning working eight to ten hours,  they take all of my time. Then after that is when I do project management, code reviews, support requests and that type of stuff. It’s on a lesser, and it’s on a tired brain when some of these support requests get looked at. Some of them I can fix and build in or add a feature to help support them, like supporting the PDF invoices plugin, doing something that’s eventually going to help the plugin sell better if it has a better integration. But those one-off, “Does it work with this?” “No.” “Then I want a refund.” “That’s fine. Go about your day. It’s fine.” But yes, being if you do launch your plugins Joe, and you do get inundated with support requests, that’s a good thing because it means you’ve got a lot of sales. That’s a good place to be.

Joe: That’s awesome. That’s the pull quote for this episode. I love it. Cool. With the last few minutes we have, I do want to ask you two questions. What are your plans for the future? And, do you have any trade secrets for us?

Daniel: Plans for the future, continue serving subscriptions clients for Grow Development. Ship a couple more plugins at Shop Plugins. We have three in the queue that are waiting on me to review and to do the marketing copy for it to get them launched. The trade secret is actually related to that. The trade secret is just freaking launch. Get your stuff out there because there’s two things that are going to happen that you need. One is Google’s going to index it, and that indexing will pay off. Maybe not today, maybe not tomorrow, but maybe in 12 months. We saw that with Shop Plugins we would launch a plugin, and we launched in February 2015, and we saw when plugins got indexed. Then we saw a six-month window to when after we launched them that we started getting more organic traffic and sales to that plugin.

It was there. You could see when we put the landing page up and when traffic started flowing because we dialed in the marketing copy or whatever to get sales. That’s not going to happen, that process isn’t going to start until you hit publish, so hit publish. The other thing related to that is you’ll get feedback from people to ask questions on,  “It does that, but does it do this?” And if you start stacking up that customer feedback from people who are actually looking to spend money on your product, then that’s valuable. That’s gold. You can assimilate that into your process, maybe change your features, maybe tweak your marketing copy. Then it doubles down on itself. It compounds on more people looking for the same thing and finding your product, and they’re buying it. So, publish your stuff and get it out there. Start talking about it and having a dialogue, don’t do it in a vacuum.

Joe: That’s great. I have come into some extra time this week, so maybe I will launch my first plugin this week. Awesome. Daniel, thank you so much for your time. Where can people find you?

Daniel: Awesome. You’re welcome, Joe. I’m glad to be here. You can find me online at my website, and everyone tries to add a dot com or dot something onto it. It’s top-level domain for Grenada, but whatever, it was the shortest Daniel domain I could find. Then most places I’m @growdev,  short for Grow Development. But Twitter, Instagram, and YouTube I’m @growdev.

Joe: Awesome. I will be sure to link all of that in the show notes. Once again Daniel, thank you so much for your time. Awesome advice and thanks for getting a little bit philosophical with me today.

Daniel: Any time, Joe. Thanks for having me.

Outro: Thanks so much to Daniel for joining me today. I appreciate everything that he offered from the [just freaking launched] to the advice that, if you are inundated with support requests, that’s a good thing. It means that people are buying your plugin and that’s rarely a bad thing. Thank you again to Daniel, and thank you to our sponsors Creator Courses and Pantheon. They are both putting out great resources for Gutenberg and the impending WordPress 5.0 launch. My question of the week for you is, why haven’t you launched your plugin yet? Are you thinking about selling a plugin, and what are the stumbling blocks? I have a bunch that I haven’t sold yet. Maybe because of this episode I will, once I have a little bit of downtime to build up the shop or create a simple checkout process.

But anyway, what is keeping you from launching your first premium plugin? Let me know at or on Twitter @jcasabona. You can also head over to the How I Built It Facebook group and discuss these things with other listeners. You can find that over at If you liked this episode and are enjoying the show, you can go over to Apple podcasts and leave a rating and review. It helps people discover the show, and the show has seen great growth over this last year. I want to see that continued now and into 2019. For all of the show notes you can go to Once again, thank you so much for joining me. Until next time, get out there and build something.

The post Daniel Espinoza and Wearing Many Hats appeared first on How I Built It.

Nov 20 2018



Rank #15: Episode 35: Diane Kinney & Writing an eBook

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Diane Kinney is a WordPress Developer, Designer, and Marketer. And soon, she’ll be adding author to that biographical line. She and Carrie Dils are working on a book called Real World Freelancing that talks all about what it really takes to be a freelancer. In this episode, she and I talk all about the writing process, decisions for self-publishing, and more.

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The post Episode 35: Diane Kinney & Writing an eBook appeared first on How I Built It.

May 09 2017



Rank #16: Episode 16: Jackie D’Elia & What We Learned Podcasting, Part 1

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It’s the end of Season 1! In this 2-part episode, Jackie and I cover everything we’ve learned while starting a new podcast. In this part (part 1), we go over the ideas for each podcast, some early trial and error, pre- and post-production, tricks of the trade, and more.

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The post Episode 16: Jackie D’Elia & What We Learned Podcasting, Part 1 appeared first on How I Built It.

Dec 06 2016



Rank #17: 100: How I Built My Podcast

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I can’t believe we’ve reached episode 100! This episode is an introspective (retrospective?) on how I built How I Built It. I’ll go over the idea, what I’ve learned over 2 years of podcasting, some pretty sweet automation, and more. I want to everyone who’s listened, shared, came on, and sponsored the show. I wouldn’t have been able to get here without all of you!

Question of the week: Why haven’t you started your podcast? Let me know in the comments or at

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Sponsored by:
  • Creator Courses: Access every course, now and in the future, with a membership. Plus, get 15% off for listening.
  • Pantheon: Get ready for Gutenberg. Sign up for a FREE account today.
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Hey everybody. Welcome to episode 100 of How I Built It. In today’s episode, I don’t have a guest. This is a little bit new to me. This is just going to be me, talking to you about how I built this podcast. Over the last two and a half years I’ve gotten a lot of questions about how I put together the show, how I built the website, how I built my audience.

I’m going to run through the questions I normally ask, but it’s just going to be me answering them. I hope you like it. It’s a little bit of an introspective, or a retrospective maybe, for the hundredth episode. I’m excited to talk about this with you, the people who have made this show possible. Thank you so much for that.

Before we get started, I do want to tell you that the show is sponsored by Pantheon, our season-long sponsor. I will mention them again later in the show. I also want to tell you that I have launched a brand new course called Build Your Podcast Website in Three Days. I’m going to be talking a little bit about how I built How I Built It, but this course gets into the technical nitty gritty.

We talk about signing up for hosting and buying a domain, installing a platform for you to host your podcast, setting up Castos for audio and then submitting your show to the likes of iTunes and Spotify. I’m excited about the course, and you can get a special offer for the next seven days from the time this is released. That’s about early November.

You’ll get a special offer if you go to Definitely check that out. I’ll tell you again about Pantheon later in the show. Without further ado, let me tell you about how I built How I Built It.

Most of you know who I am and what I do, so we can skip that question. I am a front-end web developer, I’m an educator, but the podcast is what we’re talking about today. I came up with the idea for this show in maybe the late middle of 2016. I had just gone on my honeymoon, we were in Italy, and most of the websites had a .it domain. I thought that would be a cool domain name, but I didn’t have an idea attached to it. Fast forward to when I got home from my honeymoon, I realized that I wanted to revamp my online courses or the way I was doing education.

I was teaching at the University of Scranton, but I had just moved away from Scranton. I wanted to keep teaching, and I thought, “Maybe webinars would be a good way, or in person, classes might be a good way.” Neither of those worked out. Ultimately, I had to do online courses. I was having conversations with a lot of people on what I could do to position myself properly while also not competing with friends who were in the same space.

The conversations that I was having were so valuable that I thought, “Other people should be hearing this. Other people should be privy to the information that my friends and others are freely giving me.” So I decided to buy the domain and start the podcast with that in mind.

I bought the podcast domain through GoDaddy because I am a US citizen so I could not just full-out buy an .it domain. They have a brokerage program, so that’s how I got the domain, and then I decided to start the show that way. That’s how I came up the idea. As far as research goes, I’m not great at researching. I’ve probably said this a lot throughout the years, but I did want to make sure I did this right.

First of all, I wanted to make sure that there was not another show out there already doing this. And at the time, there wasn’t. About three months later there would be, and I’m just considering that validation of my own idea.

But I did look in iTunes to see what kind of podcasts were covering this sort of topic, and I was going to stick in the WordPress space, so I limited my search a little bit to maybe business and technology. Business, technology and WordPress and there wasn’t something out there. So I thought, “OK. This is good. I’m not going to have the exact same show as somebody else.”

Then I researched how I would put this together. Naturally, I would use WordPress because I’ve been using WordPress forever. I have a custom theme that I built called Parsec, and I figured I could modify that to do the podcast things that I wanted to do. But it was my friend Jackie D’Elia who is a graphic and web designer and a Genesis developer, and she has a podcast called Rethink.FM. She was on season 1 of the show, and she asked me, we were in a mastermind together and she asked me, “Where are you hosting your audio?”

And I was like, “I was going to host it in WordPress. Just upload the audio files.” She goes, “You probably shouldn’t do that. I’m going to host mine with LibSyn, and you should look into separate audio hosts for a few reasons.” So I dove into researching that. And I thought, “How many people are using a separate audio host?” It turns out most of the podcasts I listen to used LibSyn for a bunch of reasons.

If you’re using a separate audio host, iTunes I learned, pulls the audio from that host. They don’t download your show and serve it up through their servers. You want a good rock solid host for your MP3s. These other services, LibSyn, Castos and whatever else is out there, also provide analytics. So you get download numbers, and where your show is being downloaded from geographically, and what app, and you get other information about analytics for your show. That turned out to be important and here’s why.

When I first started the show, I thought I would use this to cross promote my online courses, so I wasn’t going to accept sponsors. But then somebody wanted to sponsor the show, and I thought, “I’m not going to turn away money, but I’m going to change the scope a little bit. Now, this show is going to be sponsored.” So I got lucky in that regard, but I’m glad that I did that initial research because if I had just uploaded the MP3s to the WordPress directory, it would have been a burden on my host.

The original host I was using, the show was already burdensome, and I wouldn’t have the statistics for my pitch deck which has now evolved to send to sponsors. I wouldn’t know how many people were downloading the show except for maybe my Google analytics. I’m glad I did that research, and I’m glad Jackie said something about that.

I also researched the gear. I had this Samson Meteor– I think it’s a Samson Meteor mic. It was fine, but I used this opportunity to get a Blue Yeti and a boom arm for the Blue Yeti so that it wasn’t in my way. I looked at what software I should use. I was using a Mac full time at that point, so I would use Garage Band. “Do I need a pop filter?” So I built out version 1.0 of my podcast set up, which was a Blue Yeti, a boom arm, and a pop filter. That was the extent of it. I knew how to put a WordPress site together, and I found a good plugin, a popular plugin called PowerPress. I think Matt Madeiros from the Matt Report told me about that one, and I was able to use LibSyn with PowerPress even though they have their own service called Blubrry, and so I put the site together.

Over time I did more research to figure out, “What do sponsors want to know? What do I need to know about my audience? How do I engage my audience? Do I need better equipment?” That was maybe the first really big upgrade I made to my podcast set up, was my equipment over last year. I bought a new XLR microphone. The Road Pro Caster. I have the same boom arm, I have a different pop filter that fits the Road Pro Caster, and then I have an ART voice channel which is how I can make sure that no outside noise is getting into my microphone. Among other things, I can also make my voice sound warmer or lower, like more muddy, is the audio term. I can tweak it to make it sound just right. If I have a lot of s sounds, a lot of sibilance, I can use a de-esser to make that less grating on your ears.

I did later research like that, and then the last big bit of research I did involving my show was over this past summer at Podcast Movement. I talked to a lot of people in the space, specifically about how to get sponsors and how I can improve my show and the automations. I’ll talk about all that in the next segment of the show, but I did continue to do research for how to improve this show. It’s a living, breathing thing at this point, so I’m not just going to launch it and put it out into the world and say, “Here you are. Here’s my podcast.” I’m going to think about ways to continually improve it.

That was one of the big things that I researched, and I guess finally, the last thing that I want to point out is that I added transcripts in part as some of the other research I was doing. Like, “How important are transcripts?” That was also a result of the research that I was doing. That’s the lion’s share of the research that I have right there. It was mostly, “How was I going to host the audio? How should I build my website? What equipment should I use?” Another one was, “Should I do it live or pre-recorded? Pre-recorded is definitely the way to go. I’ve edited out a couple of mess ups, so I’m really glad I’m not doing that live. That’s where most of my research came in.

As far as the title question, how did I build it, we’ll get to that. But first, I want to tell you about this episode’s sponsor and the sponsor for my entire season, and that’s Pantheon.

Break: Today’s episode is brought to you by Pantheon. WordPress 5.0 and the new editor Gutenberg are coming. Are you prepared? Do you want to learn about the changes in advance? Pantheon has gathered resources to help you prepare, including webinars and tutorials. Pantheon also has made it easy and free to try Gutenberg with your site before the official launch. Visit Let them know that How I Built, It sent you. Now, back to the show.

So, how did I build How I Built It? There’s a couple of things here that I want to mention. There’s the site, putting the show together, scheduling the guests. Let’s start with maybe the more technical stuff. I signed up for a LibSyn account, and I built the podcast website on top of WordPress. I used the plugin PowerPress to add some extra functionality for podcasting and to make sure that the feed that I submitted to iTunes and other directories was properly formatted. That’s something that I think doesn’t get enough credit.

As far as these podcast plugins for WordPress go, customizing WordPress feeds is a difficult thing, and a good podcast plugin will make sure that the feed for your podcast is properly formatted before you submit it. Because especially iTunes is very particular about how your feed is formatted. I didn’t have to write a single line of code to make that happen, PowerPress handled it automatically.

The theme that I was using at the time was Parsec which was my own personal theme that I wrote for my book, Responsive Design with WordPress. I made a child theme for it that was specific to podcasting, where I would put the show notes and the images and anything pertaining to the audio, subscribe buttons, anything pertaining to that content I laid it out the way that I wanted.

I put together the episodes page and a sponsor page and a contact page, and things like that. So that’s how I put together the site. It was pretty barebones when I first launched it, and I didn’t want to spend a whole lot of time putting the site together if I decided a month in that I didn’t like it. That was how I built version 1 of the website.

As far as putting together the episodes and how I built those when I first started out I just reached out to my friends, especially the people I’d already spoken to. I said, “Do you want to be on a new podcast I’m starting?” I made a list of people that I would love to talk to, and I said “I’m starting this new podcast. Do you think it’s something you’d want to be on?” And my first five guests were amazing. Jason Coleman, Rebecca Gill, Brian Krogsgard, Corey Miller and Carrie Dils. They came on no questions asked. They were just like, “I’d love to come on the show for you, I appreciate you asking.”

It was a very manual process. “What time works for you? Let’s get on Skype, and I’ll record it. If you could record your side of the audio, that would be good,” and I would collect it all. That process evolved a little bit because I added Calendly, so I would say, “Pick a time that works for you here. We don’t have to figure out time zones, Calendly will already do that.” Then it sends them a link to some guest notes, some things that each guest should know, and how we’ll talk, and then a calendar invite.

All of that is taken care of with Calendly. That was maybe the best addition to my process that I made for a long time. When we got together and recorded the audio I used– At first, I was using QuickTime to record my audio, and I asked my guests to do the same. Then I wanted to make sure I had a redundant backup, so I was using Skype at the time, and I used Skype and a program called E-cam Recorder to make sure that it recorded both my audio and my guest’s audio in two separate tracks that then can be combined later.

I still ask my guests to record their side of the audio, though. That’s because if we get into a situation where maybe the internet gets bad on either end, their voice gets like robot-y. You get that it’s hard to understand them, and I wanted to have the best possible audio quality. I had them record their side of the audio. I wanted the full uncompressed version, and then I would combine them.

And speaking of, I did the editing for the first few episodes, and that was the most time-consuming part. If it was a half hour episode it would take me a couple of hours to edit the audio, and I thought, “This is just a learning curve,” and then I realized, “No. I have to listen to the whole episode, I have to cut things out, I need to process the audio, and I need to add the bumpers,” and stuff like that.

I would do the intro and outro separately because I wanted to recap the episode. That was another evolution in the format of the show. But I used Garage Band to do all that, and Garage Band is a nice program, but it took a lot of work. So that was the first thing that I wanted to cut out, as far as me doing it.

If we’re talking about how I built this whole podcast, then I want to talk a little bit about the automations that I’ve built over especially the last year to put my show on autopilot a little bit and take up less of my own time, because then I could focus on researching the guests and asking the right questions and promoting it properly and just putting together the best possible content and allowing other people to play to their strengths to make this the best possible show.

So I have two big automations set up that I’ve built for the podcast, and the first has to do with scheduling. I mentioned Calendly, and Calendly does a great job of taking the headache out of scheduling with another person, again especially if they’re in another time zone. I use Calendly, and when somebody schedules an appointment, I trigger a zap in Zapier to create a Zoom call.

Another evolution is that I’m using Zoom now instead of Skype. Most of my guests, it turns out, prefer Zoom to Skype. I got a lot of, “I haven’t used– This the first time I’m using Skype in years, sorry.” I just wanted to take the headache out of that, so I use Zoom. If a guest requests Skype, I will gladly do that, but Zoom has been pretty smooth so far for most of my guests who already use Zoom.

So the automation goes from Calendly, it sets up a Zoom call, it updates the Google event calendar or the Google Calendar event to include the new Zoom URL and the guest notes that the guest should read over before coming on the show, and then it also creates a new note in Evernote with all of the information the guest filled out from the Calendly as well as headings for each question. That makes it very easy for me to take notes during the show, and good notes during the show that I can then pass off to my transcriber.

This is where the second big automation comes in. I record the episode, and I save both my side of the audio and the guest side of the audio, and when I do that, I have an app running on my Mac called Hazel. Hazel will clean up the desktop, and it’ll take those files, and it will move them into a folder in Dropbox called “Needs Editing.” I add the intro and outro, the sponsor spots all separately, as well as the intro and outro music. When a new folder or an episode is complete, Zapier triggers an email, and it gets sent to my editor. It says, “There’s a new folder in Dropbox that needs to be edited.”

He then edits them and puts the episode into a folder in that same Dropbox area called “Needs Transcribing.” My transcriber gets the episode or a notification for the episode, and now she can transcribe it. The name matches a note in this Evernote notebook that we both have access to, so now she can put together a good transcript with all of the terms I’ve used, and she puts together the show notes for me.

I’ve set up these automations, I show up and record the show, and then I do add everything to WordPress. I like doing that because it feels like I’m shipping the next episode. But from the time I save the audio to the time I need to add it to WordPress, I don’t touch the show at all. I have automations doing that for me. That has saved me a ton of time. So, that’s how I built out some of the automations.

I want to improve the process a little bit, which I’ll talk about later. But for the latest version of the website that also went through a major redesign. I’m using Monochrome Pro now from the Genesis framework, or from Studio Press using the Genesis framework. It was my first foray into using Genesis, and I was pretty excited about it. I was able to use their hooks and things like that to customize the experience for the content, and so I’ve made the episodes easily consumable.

I’ve put the sponsors in a more visible area for each episode, and I have included the transcripts in such a way that it doesn’t like blow up my listeners’ podcast feeds. You can click to read the transcript if you want. If somebody is reading the transcript on the website and they want to follow along, the audio is included there too. The other major thing that I added since– Well there’s two major things.

One is a custom plugin that I built on top of PowerPress. That creates a custom post type for me to add sponsors and associate those sponsors with episodes, and then the same thing for transcripts. I added transcripts around season 3 or 4 as soon as it was not financially prohibitive for me to do so. I’m working on the back catalog, but I’m very excited that I’m able to have transcripts kind of per episode moving forward.

I can associate sponsors and transcripts with an episode, so they are all separate in the WordPress backend, but the user or the listener sees them all nicely in one place. I also used SearchWP to associate the transcript text with an episode, so if you go to my website and search for a term if that term exists in the transcript that episode will show up. I’m excited about that.

I do have a video on how I put all of this together that I will link in the show notes for this episode, and it will be That is the latest version of the website. As far as the latest version of– Well, I talked a bit about the latest version of the process. That’s kind of how I built the whole show. With the automations, with the theme, and things like that. I know we’re coming up, I’m watching, we’re coming up on time here. So I’ve talked a little bit about the evolutions. “How has the show changed?” I’ve added transcripts, I’ve improved my process, I don’t just start with the sponsor spot now I give you a recap of what we talk about and what to look for, and then I talk about the sponsors. I’ve added a mid-roll spot for the sponsors, and I’ve added an outro.

The overall production quality has improved because of my new equipment, and because of this new process where somebody else is editing the episode and not me. I’m excited about that. As far as my plans for the future go, I want some more automations. I want to make it so that I don’t have to upload the episode to LibSyn anymore. Either my editor can do that, my transcriber can do that, or maybe I can kick off a zap on Zapier where when a file with a certain name hits a folder it automatically gets uploaded to LibSyn. I don’t know if that’s possible, but it’s something that I want to try.

I also want to experiment with episode formats a little bit. This is the first episode where I’m just talking directly to you, and there’s no guest. If you like it, let me know, and I’ll do you more like that. Or if you’re like, “You’re great, but I prefer listening to somebody else most of the time.” Let me know that too. Interviews definitely aren’t going away, and I have a lot of really great ones scheduled for season 6.

I also want to try to improve engagement. So, these are my plans for the future. Lastly, I’m thinking about maybe doing away with the seasons, and maybe just taking a couple of breaks. Like over the holidays, maybe I’ll take a break. Over the summer I’ll take a two-week break. But I am at a point now where I have enough content to fill pretty much a whole year, and I love doing the show, and I want to keep doing that, so I want to get ahead of the curve. I want to experiment with episodes, and I want to improve engagement.

Those are my plans for the future, season 6 and onward. To improve engagement, I would love if you just reached out to me and let me know, ask me questions or make suggestions. I want to know what you the listeners are thinking. Then there’s the trade secret. My favorite part of every episode is asking this because every guest responds the same way. They go, “Trade secret…” and they think about it for a little while. And I knew I was going to ask myself this, so I thought about it before I started recording.

My trade secret is this. Starting a podcast is more time consuming than I thought it would be, but it’s not hard necessarily. Yes, it takes time. Yes, there are things that you need to know. But if you’re comfortable speaking to another person, or speaking in front of a microphone, you should give it a try. I have more fun doing my podcast than I do anything else. If I could be a full-time podcaster, I would strongly consider it.

I love creating my online courses, but getting to interact with people and talking to the listeners, talking to the guests, working with sponsors has been the most fun. I consider myself incredibly lucky that this podcast has taken off the way it has, and I have you to thank, and I have my guests and my sponsors to thank. And yes I know I have put a lot of work into the show, but that work is maybe secondary to the reception that it’s gotten and to the support, I’ve gotten from other people.

If I haven’t gotten the support from you and the guests and the sponsors, it would have been very hard to put in that work. I’m grateful that I’m able to create something that gets downloaded 5,000 times an episode 40,000 times over the course of a month, and I want you to experience that joy too. So my trade secret for you is start podcasting today. It’s time-consuming, but it’s super rewarding, as most rewarding things are time-consuming.

I would strongly recommend you do that. If you want to know anything else about the show, reach out to me. I know I did get one question, “How much does it cost to produce an episode?” I have found some great people on Fiverr to work with, and they do fantastic work. It costs maybe $60 an episode, maybe $70 an episode and that’s to get it edited and transcribed. Again, I’m super lucky that I found such great people to work with.

If you have any questions about podcasting, please reach out. Again, thank you so much for listening to 100 episodes, and I appreciate you for doing so. So, that’s it for this episode. Thank you for joining me. I hope that it was illuminating, I hope that maybe you got some questions answered. I hope that you got ideas for how to start your podcast. Or if you have a podcast, things you can do to improve your podcast, if you think it needs improvement.

My question of the week for you is, why haven’t you started your podcast if you haven’t? Let me know. Email me or reach out on Twitter, @jcasabona and let me know and I’ll give you a pep talk to help you. Thanks so much again to our sponsor Pantheon. Definitely check out the things they’re doing, Gutenberg and WordPress 5.0 are coming, and they have resources that will help you. That’s over at

That’s the recap, the sponsor spot, the question of the week. If you want to talk with other people who are answering the question of the week, join the Facebook community over at If you have your show but you need a great website, head over to and you can find my newly launched podcast website course, Build Your Podcast Website in Three Days.

Thanks so much for joining me for episode 100. If you like the show, make sure to give it a rating or review over on Apple Podcasts or wherever you listen to podcasts. That’s one of the big reasons the show has grown, is because people are rating and reviewing it. It’s getting listed in the top 50 episodes consistently, which is another thing that I’m super appreciative of. Thanks so much for joining me. Until next time, get out there and build something.

The post 100: How I Built My Podcast appeared first on How I Built It.

Oct 30 2018



Rank #18: Zach Tirrell and Loxi

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Today we’re talking to Zach Tirrell from Modern Tribe. We talk all about how they re-imagined that plug-in as Software as a Service called Loxi. We go over how they decided on which features to support, the importance of good design, and the tech stack, like using React. Speaking of React, We also talk a bit about Gutenberg.

Show Notes

Sponsored by:
  • Traitware: A faster, more secure way to login with WordPress
  • Pantheon: Get ready for Gutenberg. Sign up for a FREE account today.
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Pre-Intro: Hey everybody – before we get into today’s episode I want to tell you about my new podcast, Creator Toolkit, It’s a show where I take you through building specific projects on the web, or help you make important decisions. The current episode is about self-hosted vs. hosted. I’d love if you checked it out at or wherever you get your podcasts.

Intro: Hey everybody and welcome to episode 89 of How I Built It. Today we’re talking to Zach Tirrell from Modern Tribe. Modern Tribe is a supporter of this show through their WordPress plugin, The Events calendar. In this episode we talk all about how they reimagined that plug as Software as a Service called Loxi. We go over how they decided on which features to support, the importance of good design, and the tech stack, like using React. Speaking of React, We also talk a bit about Gutenberg.

Sponsors: This week’s episode is brought to you by Traitware and Pantheon. We’ll hear about them a little later on, so for now…on with the show.

Joe Casabona: Hey everybody. Welcome to another episode of How I Built It, the podcast that asks, “How did you build that?” Today my guest is Zach Tirrell, director of product for Modern Tribe. Zach, how are you?

Zach Tirrell: I’m doing great. How are you?

Joe: I am fantastic. It is the end of June as we record this, so summer is going by a little bit fast. But I’m enjoying the nice weather and I got to enjoy a Yankee game yesterday. So I’m all excited.

Zach: Wow, that’s fantastic.

Joe: Yes. So I’m very excited to talk to you today. Modern Tribe has been a supporter of the show, but aside from that they are doing some very cool things. Zach, why don’t you tell us a little bit about who you are and what you do?

Zach: I oversee all the products work for Modern Tribe on that side of our business. That means primarily The Events Calendar plugin and the various add-ons that folks are familiar with there. We have a few other smaller plugins, like Image Widget, for example. But mostly it’s events based, The Events Calendar event tickets, a lot of event based plugin work. And our newest offering which is a SaaS based solution called Loxi.

Joe: Nice. And Loxi is going to be primarily what we’re talking about today, but just to touch on something that you mentioned. Modern Tribe does both product and service work. Is that right? You guys do agency work?

Zach: That’s right. We have a we have a very large agency business here, that’s about 70% of our business and then our product side is about 30%. Almost 40%.

Joe: Nice. Very nice. So let’s jump right into it then. Why don’t you tell us about Loxi?

Zach: Sure. Loxi is a SaaS based calendar, like the WuFoo Form equivalent for calendars. Where you don’t have to have any infrastructure to set it up, you create an account you get an embed code and you can drop it on any site. A no-fuss based calendar. For this particular audience, it’s interesting to know that we built Loxi on top of The Events Calendar and the WordPress REST API.

It’s a product that leans into our existing codebase and experience in WordPress, but has an entirely brand-new fresh user interface, and no need for folks to worry about their own scaling or uptime or plugin updates or any of those things. Suddenly they go away and you just get a nice, easy, beautiful calendar to work with and put on any website. It’s not limited only to WordPress. You can put it anywhere.

Joe: That’s fantastic. Because essentially The Events Calendar is a WordPress only plugin.

Zach: Correct. The Events Calendar is a WordPress plugin. We’ve got a lot of reach there with 600,000 active installs, but Loxi opens up the ability for us to take that into a whole lot more corners of the internet.

Joe: Nice. When did this idea come into fruition? Where you’re like, “Let’s take The Events Calendar and turn it into a stat so we can reach that wider audience.”

Zach: we were talking about that right on day one when I joined Modern Tribe. Which was just over three years ago. That was the vision when I joined the team.we really wanted to take The Events Calendar and move it to a broader audience and to pivot it into SaaS.

And not entirely pivot, because we totally still plan to enhance and release The Events Calendar. It is the underlying core here of the SaaS. So both benefit at the same time. But the goal was definitely, from day one as far back as three years ago, to get us there. There was a lot of work we had to do first. But one of the interesting things that happened is just over a year ago, Jeff Graham who ran our support team here, was looking for a new opportunity.

He said, “I love managing support, my passion is support. But I want the opportunity to maybe build something. Like run it, do the strategy on it. Coordinate, design,” all those sorts of things. So Jeff came to us with that and then simultaneously we were thinking, “It’s finally opportunity for us to add another team to the product side, and have them build something new.

Some completely new solution. And we said, “The stars are lining up.” We had three options on the table. Jeff with his passion for support and our customer audience, one of the things he looked at was he said the opportunity to rebuild The Events Calendar Calendar’s user interface and also serve this need of expanding beyond WordPress sounded like an exciting journey for him.

So he took a lot of his customer experience and knowledge about what they wanted out of a solution, and brought that into this new role for himself. And he’s been the strategic leader on this. I clear a lot of hurdles for him and try to keep him protected, But Jeff very much was the strategy leader on Loxi and was able to come at it.

And I think anybody who uses that product can see that customer centric vision there. The interface is as minimal as we could make it, it tries to be really easy. We want it to be quick to create an event and also beautiful to do that, and to experience that. Versus WordPress, which we all love, But the WordPress admin UI is not the pinnacle of user interface design.

Joe: Absolutely. So there’s a couple of things that I want to mention there. First is, you’re absolutely right. People say that WordPress is very easy but it’s mostly people within the WordPress community. And we’re hoping that Gutenberg will make that better, and we’ll touch on maybe Gutenberg development a little bit later.

But the WordPress interface is rightfully going through some changes right now, which is good. The other thing that I want to mention is that it’s something that I hear more frequently on this show than is the perception. But you basically used your customer support knowledge to build a better product.

Zach: Absolutely.

Joe: That’s great. We touched on that a little bit with the GiveWP or the Give guys, when they were on the show. And it’s been a reoccurring theme, “Listen to your customers. Listen to your customer support. Make sure the customer support guys are talking to the developer folks and you’ll end up with a better product.” I’m very glad to hear that echoed again here with Loxi.

Zach: Yeah absolutely. I think it’s expensive honestly to do a bunch of user testing and detailed UI work with groups and audiences, and do all of those kinds of usability tests. And we’ve certainly done some of that stuff. But being able to take someone who has been on the frontlines and has heard about all the rough edges, and have them come in and be like, “Here. Try to build this thing from scratch with all of that in mind.” it gives you a lot more implicit understanding about what customers want.

Joe: That’s fantastic. Very cool. Aside from that was there other research that you guys did? Did you guys look that competition, or you said that this was the plan basically from the day you came on. So what was that process like?

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Zach: We did. Yeah. We’ve been we’ve been looking at this for a long time. The SaaS based calendar space is not empty. There’s plenty of folks who exist in there and there are people doing some really great stuff. And honestly one of the things we did early on was we reached out to a bunch of the existing players and said, “Is anybody tired? Does anybody just want to want to move to an acquisition?” which honestly wasn’t exactly what we wanted to do, because we wanted to leverage The Events Calendar. We wanted to take our plugin and put a new UI on top of that.

But if we could have taken a shortcut and snatch somebody up We would’ve. We talked to a half dozen different folks in the space to see if anybody was interested in going that route. Nothing really emerged from that, but honestly I had a lot of great conversations with a lot of players in the space.

So we’ve been thinking about it. One of the other things we did way back, and if You look back at our road map you can see some of this stuff. Where we’ve said, “If we’re eventually going to build this SaaS we need full support for the WordPress REST API. We’ve got to do that.” So we added REST API support into the plugin and we released that publicly, and there was a handful of other things we did.

We have actually not yet released this in our plugins, but we rewrote the whole way our backend recurring events infrastructure works. Which is a deceptively complicated feature. And Loxi is actually running on a new iteration of that backend. We haven’t yet released it publicly, we’re intending to but we’re just trying to work out all the backwards compatibility bugs, and make sure that everybody gets a smooth migration there. So that was fun.

But honestly, one of the things that I think is really interesting about what we did here, is since we were able to build a completely parallel team to support and build Loxi, we had this opportunity to hand pick a group and say, “These are the particular skills we want to build this thing from the ground up.” I don’t know if you’re familiar with Scott Kingsley Clark, who is famous for Pods?

We brought him in full time. He’s been working on Loxi for the past year. So we had some pretty strong technical chops that were able to come in and help us do a lot of the infrastructure, and keep contributing back to our core plugin. So he was constantly trying to think about, “How do we scale it? How do we build many, many calendars on top of this plugin?” So that was really fun to have him join the team and lend his expertise.

The other one is David Hickox who is a really great designer. He had been working on our agency side for a long time, and was also really interested in this challenge. Jeff and I got him real excited about it. So he was able to come in with almost a blue sky, thinking about, “How would I design the interface for a plugin?” He and Jeff just went back and forth on it for many months. Lots of prototypes. Lots and lots of prep work before we ever started writing a lot of a lot of code directly related to Loxi, but there was lots of infrastructural stuff we were working through.

Joe: That sounds fantastic. And this perfectly moves us into the title question, which is, “How did you build it?” You’ve assembled a great team of talent, you are working off of a preexisting codebase with The Events Calendar and working with the WordPress REST API.

How did you put that all together? How much of The Events Calendar needed to be rebuilt in order for this to work properly? You alluded to that, but just the overall process of converting a plugin to a SaaS.

Zach: The big things with the existing Events Calendar plugin that we needed to address was first getting it base-compatible fully with the REST API for updates, edits, deletes. The whole gamut. And while we were doing it, we knew we were going to be moving into a SaaS and we wanted to be able to move quickly. So we added a lot of testing. There’s lots and lots of testing that was added through this process.

We’re not at a point where we’ve got full coverage or anything like that. As far as The Events Calendar goes. But as part of this effort we did add a lot of testing to the base plugging. The bigger thing we had to do around The Events Calendar was address how to handle what we perceive eventually as reality, which is large data sets.

We knew that it needs to be very fast. The Events Calendar itself is always optimized for the absolute fastest way to retrieve data. Now we’re using the WordPress data structures with custom post types and all this, and post meta. So it’s not always the fastest. So we have to figure out, “How are we going to scale that aspect of it? How are we going to be able to do that?”

And Scott wrote an Events Calendar integration for ElasticSearch. I think we call it Elastic Events, which we wrote as an ElasticSearch, ElasticPress plugin. That was a big piece we had to build to make sure that this was all going to be fast. We actually just released that plugin for free last week. And we were excited about that. It was another piece where we were like, “Well we had to build this for ourselves. But anybody else doing this at scale should benefit from the work we did.” So we released that.

The piece where we had to do a lot of full rebuild work was around the interface. Loxi, the application is entirely React based. So we had to we had to rewrite everything. We brought on a React dev who’s crazy ridiculously good at his job. He pretty much all by himself rewrote all of these interfaces and views and stuff, purely in React.

We’ve got this snappy interface that’s real tight and feels modern, and it was a nice chance to reimagine that stuff. That was also a very costly endeavor, it took a lot of time and it took a lot of effort. We probably could have built things a lot cheaper if we hadn’t gone that route. But it’s what we wanted to do. It was our vision of what of what the product was going to be.

Something where that interface felt like it was getting out of your way, instead of getting in your way. And then it was very easy, and friendly and light to use, airy almost. And React gives us much more of that experience. Where you don’t have full page reloads happening. The interface just clicks right along.

Joe: that’s very interesting to me. I’m just getting into React development now, because I’m very late to every party. There’s a million JavaScript frameworks out there so I try to see which one is going to be the winner before I sink a lot of time into it. And it looks like you, maybe clairvoyantly, picked the winner. When you chose to use React, had Gutenberg been announced yet? Did you know? Or were you just like, “This is something backed by Facebook. It’s probably going to be around awhile.”

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Zach: No, it had not been announced yet. If we go a little bit further back in our history. We, Modern Tribe, not the product side but the agency side. We decided that we were going to add React to our tool belt about two years ago now, and we relaunched our Try.b, our Modern Tribe company website, as a fully React based website on top of WordPress.

And one of our very strong JavaScript developers, Sam, wrote a fantastic article that got us a bunch of attention Two years ago about how we built that, and all of the details. And that’s a pretty great article. So that got us a bunch of attention and It also gave us some internal skills around it. We’ve then worked on a couple of agency projects that were really heavily React based, and so internal to Modern Tribe, that was the toolset we’d started to build.

We weren’t doing anything necessarily on the product side with it yet, but we said, “That’s what agency is doing. Those are the skill sets we have. If we hire somebody we actually know how to evaluate the skills. We could bring this guy in, and if he needs mentorship or starts to go off the reservation, we’ve got somebody who can help.” thankfully that wasn’t the case. Neale’s just ridiculously good.

He actually has helped even move some of the agency thinking forward in ways that are just a fun giving back, and that’s a common thing for our organization to do. They make an innovation and we grab a hold of it, and then we go a little further, and then shoot it back over the fence. There’s some give and take there.

But yes. So all that happened and then Gutenberg got announced and we were like, “It looks like we chose the right technology,” which was helpful. And then that’s helped us to start getting into some of that work. And honestly I feel like we are in a position to jump on that maybe a little bit more with both feet than some of the other folks in the space.

Joe: And another thing that you mentioned is that you wanted to make your plugin REST API ready, fully. And that’s also something that you need to do in order to support Gutenberg. You need to have that turned on when you define your custom post types, for example. So did you guys just jump feet first into Gutenberg development as soon as you thought it was stable enough to do so?

Zach: Yes. So what we did with Gutenberg is actually we had mostly held off. We were talking about it a lot, holding and circling it, but not 100% sure what we were going to do. And then I went to WordCamp US last December, and while I was there I was like, “This thing’s actually ready to go now. It’s still moving, there’s still a lot to be done here, but I can I can see it.” And so when I came back from WordCamp US I met with our strategists on the plugin side.

Her name is Leah. And actually, maybe not coincidentally, maybe it’s company structure. She also worked on our support team for a long time. She was in support, did a lot of company swag work and some of those kinds of things. But also had this passion for the user experience within our plugins, because she really understood that that user mindset. And so she quickly grew into the strategist role and has done a bang up job doing strategy for our plugins overall.

But I came back and met with Leah and I was like, “This Gutenberg thing has become real. I need you to go into a cave and figure out how we’re going to do this.” And actually our first real decision point there was, “Gutenberg’s a big deal. We’re going to have to invest a lot to really become compatible with it.” We had to decide, “Are we going to just survive the Gutenberg transition? Do the absolute minimum that we can do in order to have a functional product after it releases?” Which would have been a fine approach, and would have allowed us to continue to focus on a regular roadmap and some of the things that our customers are actively asking for.

Or do we say, “Gutenberg’s the future of WordPress. If we’re going to be on this train, not only do we need to participate in the discussions from here to release on what’s actually happening, but we need to push the edges of this and make our plugin a cornerstone of what that experience is going to be.” And I was right on the fence between these two options. There was lots of stuff on the roadmap that was really exciting.

And we had just built Loxi. We’d just spent a year building a new interface to a calendar. And so I went to the team and I said, “What do you guys want to do? Which way do you feel like you want to go on this? Are you up for this journey?” And it was a different team. Gustavo, who was our lead plugins developer, and Leah and the partners at Modern Tribe, Shane and Peter and Reed. I went to all of them individually and said, “These are the options. What do you want to do?”

And every single person said, “We want to invest in the in the future here. We want to do the big thing. We know it’s harder and we know it’s going to take a lot of attention.” But every single person said, “We want to do the big thing because this is only going to happen once.” So what we actually did to help take advantage of some of the work we did, was we grabbed David who was the designer on Loxi.

And we said, “David you just spent a year designing an interface that’s React based and highly responsive and is very user centric. Want to do it again? Want to take another shot at that pal?” And so him and another designer, Rachel, we actually added a second designer because there are so many details for Gutenberg. The two of them jumped off of Loxi and came over to The Events Calendar and they’ve been every week iterating on these designs and these prototypes, and doing a bang up job with it.

Joe: I realized that I say, “Man. That’s great,” a lot. Especially in this interview. But I like everything you’re saying. Everything you’re saying is fantastic. After WordCamp US is when I talked to Zack Gordon and we decided to release our Gutenberg courses. His developer course and my user course, like super early in January. Even though it meant that we were probably going to have to iterate on that course a lot.

We just wanted to get the educational components out there because, like you said. It’s not going away. It’s going to become a bigger part of WordPress moving forward.

Zach: we immediately purchased that Zack Gordon course for Gustavo. We were like, “Here you go, man. Here’s what you’re going to do. Go read this, go dig into code.”

Joe: And it’s great. I mean I’m working through the course, learning React. And so I think that’s a very forward thinking approach. There are a lot of different opinions on that, and it’s whatever works best for your team, or yourself, or your organization. But it’s very cool to see you guys jumping on top of that.

So with the last few minutes I always like to ask these three rapid fire questions. The first is changes since launch, and you just recently launched. So maybe we can go right to, what are your plans for the future of Loxi?

Zach: Yeah. We launched to a very small audience, so it’s not it’s not like a public or big global launch. We haven’t started doing any real serious marketing outside the WordPress space, or doing any ad-buys or any of that stuff. It’s mostly quiet. We’ve been marketing to our internal audience. So we’ve got a lot of stuff still to do.

What we’ve been doing is just listening to customers and making small iterative changes. We’re trying to get to the point where a single user can have multiple calendars. We’ve worked to improve the embed, what we thought was fast in our labs Still doesn’t feel fast to us on customer websites, so we’re try to speed it up. And we’re going to continue to do some of that work. More scaling and performance and really make this thing roar. But it’s mostly that kind of stuff. There’s going to be tons and tons of little features coming every two week cycle right now.

Joe: Wow. Impressive and very cool to see you’re focusing on customer centric stuff. It seems to be the overarching theme of this episode, and a lot of other folks that I’ve talked to. So like I said I’m very glad to see that, being in the education space I try to think about the customers. I’m a front end developer too, so I try to focus on user experience. But the easier something is to use, the easier it is for me to educate on that.

Zach: yeah. The one challenge we do have there though is, and my marketing director keeps reminding me of this, is we can’t just build everything that The Events Calendar customers ask us for, because we’re not trying to recreate The Events Calendar. There is a slightly different experience. And if we just gum up the UI with all of the robust features that are built into The Events Calendar, that’s not actually the mission of Loxi. So there’s that temptation. We have to listen to our customers but also be sure not to take everything they say as gospel. That is an interesting bit of this to walk.

Joe: Totally. There’s the balancing act between somebody who wants all the features and everything, and then making that jive with your mission, the “Why you started” Loxi. I know that Jason Fried at Basecamp always says, “It’s okay to say no,” and that they “Try to say no as often as possible, except when it makes sense.” Definitely the takeaway here is listen to your customers, but don’t just take everything they say as gospel.

Zach: Yeah. Exactly.

Joe: The last question I always like to ask is, do you have any trade secrets for us?

Zach: Trade secrets. I don’t know if there is any, other than one of the things I think we have done really well is just continue to lean into the things we’re good at. With Loxi it’s basing it on The Events Calendar and making sure that even if Loxi ends up being a complete failure, the journey of building it has strengthened the core products.

Even at that point it’s not a failure because the core product has benefitted. And things like learning React and then reusing it, or building designs and then reusing them. It’s not to throw that stuff away. Build on top of the things that you have as skills and that kind of thing.

Joe: Awesome. “Continue to lean into the things we’re good at.” Love that. Zach, thanks so much for joining me today. Where can people find you?

Zach: You can find me on Twitter at my handle is @Tirrell. Just my last name. I apparently got in there early enough. Or you certainly can hit me up through The Events Calendar Twitter as well, which is @TheEventsCal.

Joe: I will link all that and more, everything we talked about, including that great React article that Sam wrote two years ago in the show notes. So be sure to keep an eye out for that over at HowIBuilt.It. Zach, thanks again for joining me today. I really appreciate it.

Zach: Thanks Joe, this was great.

Outro: Lots of great stuff here, especially if you want to get into Software as a Service. I want to thank Zach again for his time, and Modern Tribe for their support of this show.

And be sure to check out this week’s sponsors, Traitware and Pantheon.

For all of the show notes, head over to If you like the show, head over to Apple Podcasts and leaving us a rating and review. It helps people discover us! You can also join the Facebook community over at I want to build a strong community for this podcast, and Facebook is the place to do it. You’ll even find a link this week to a giveaway I’m doing where you can win my 4 favorite business books.

Finally, if you haven’t heard it yet, I’d love if you checked out my new podcast, Creator Toolkit, where we put together all the tools you need to build great things on the web. It’s on Apple Podcasts or wherever you get your podcasts now.

Thanks for joining me and until next time, get out there and build something.

The post Zach Tirrell and Loxi appeared first on How I Built It.

Aug 14 2018



Rank #19: Episode 33: Erin Flynn & Teaching Freelance

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Erin Flynn is a freelancer and educator based on Colorado. In this episode we talk about how she found her way into the product space, all the twists and turns of freelancing, and how she creates courses and keeps her sales funnel on point.

Show Notes

Sponsored by:

The post Episode 33: Erin Flynn & Teaching Freelance appeared first on How I Built It.

Apr 25 2017



Rank #20: Episode 58: Jeff Large & Podcasting for Your Brand

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Jeff and I talk about one of my favorite topics: podcasting. Jeff is a professional podcaster; he does it for other brands, so he doesn’t just have his own. He is hired to help people set up their own podcasts. Whether it be to promote their brand or other things that you could do with your podcast that don’t necessarily make direct sponsor money. We also geek out about hardware and stuff like that too, so it’s really really fun episode.

Show Notes

Sponsored by:
  • ProsPress
  • Liquid Web: Fast, Managed WordPress hosting whether your users are logged in or logged out. Get 50% off the first 2 months.

The post Episode 58: Jeff Large & Podcasting for Your Brand appeared first on How I Built It.

Nov 07 2017