Rank #1: Massey on Money: Jeff Massey
Rank #2: Hiring On Purpose: Max Hansen, Brian Mohr
Rank #3: The Aspiring Solopreneur: Kris Kluver
It’s never been easier to start your own business, but avoiding the many pitfalls can be a challenge. As a solopreneur, you need to think not only as an employee but also as an investor, manager, salesperson, bookkeeper and more.
Kris Kluver, the author of The Aspiring Solopreneur, is a seasoned entrepreneur, he has more than thirty years of experience, and he’s been involved with hundreds of businesses, ranging from consulting to real estate, online services, advertising, financial services and many more. He hopes to impart his love of solopreneurship to you so that you can achieve your dreams. So, if you’re thinking about opening a business, there’s no better time than now to make it happen.
Kris Kluver: In 2015, I needed to get a total hip and a total knee replacement. I didn’t have a big traumatic injury–I was in my late 40s and it was 100% a result of my own foolishness as a youngster. I owned it. It was a result of the sins of my youth, let’s put it that way.
So, with the surgeries, I found myself on the couch, stoned out of my gourd, not able to move and candidly, I suck at being immobile, I suck at downtime. I’m not good at that. So, I was trying to read, I would just sit there and read the same page three or four times and drool on myself and man it was awful.
I started watching television, which I don’t do a ton of. Through that process, I discovered what a Kardashian was, and it scared the pants off me. Then I ended up flipping over to these shows that showed these guys in Alaska and people living on the frontier. For some reason, I liked that–I liked the backcountry and that was really intriguing to me.
This one guy made less than $8,000 a year. If we treated our criminals like this, we’d go to jail. He’s got duct tape on his glasses and on his jacket. He drives a snow machine from the ’70s, but he can’t get through an episode without saying how fortunate he is, how grateful he is to live the life he has. Something really clicked in my head that made me realize that “Holy smokes, you know? We’ve completely lost control of the narrative of what success is. We’ve lost the idea of what success is on our terms.”
This guy, this hillbilly out in the woods, is owning it and he’s more successful than the really wealthy successful people I know, the Kardashians who appear to have everything in the world. They’ve got money, looks, fame, and all they do is sit around and bitch. Whereas this guy was looking at it differently. It really was a paradigm shift in my thinking. I really started to go deep into the rabbit hole, researching and studying the idea of helping and defining what success is, but on our terms.
Through that, I started to learn that there are so many opportunities for us as individuals and for people to go out and live their dreams. Dude, we live in the most abundant times ever, since the dawn of time, no matter what anybody says, things are getting better and better and better and better.
Humans are the only animals on the planet who look at the past with nothing but fondness and the future with nothing but trepidation, even though there’s nothing to suggest anything but the opposite. So, going through this, I started really researching and embracing it. I realized that my gift–I started my first of 14 companies when I was 19.
I have built them, bought them, sold them, advised hundreds of people on them, and I realized that that’s how I’m wired, but that most people aren’t. I started really digging into what that means. Through that, I realized that it’s my opinion that when you see people who want to go out and live life on their terms, they can. We can do anything we want right now–anything is possible. But we get in our own way.
When it comes to owning your own small business, it has never been easier to test it, to vet it, to start, and then slowly transition, so you thrive. But most businesses fail, and it makes me sick because the numbers would suggest that roughly 50% of all businesses that start fail within the first five years. That’s a train wreck.
That takes people’s lives, it takes their health, it takes relationships. All they’re looking for is they want freedom, they know there’s more out there, but they don’t know how to get it. Now, the scary thing to me is that of the 50% that make it, I would argue, another 50 to 70% of those are bumping along, succeeding despite themselves, because they are too stubborn to give in or they keep throwing money at the problem.
They aren’t thriving. It was through this whole process that I started realizing, “Man, you know, it doesn’t have to be that way and I know that because I’ve lived it. I’ve helped a lot of people with it.” That’s where I want to be able to help. I want to be able to change the trajectory of where people are, so they’re not just getting by.
Getting by sucks. I want people to thrive, that’s my objective, that’s the goal with all this.
From Surviving to Thriving
Charlie Hoehn: I’m curious, what did you uncover in your research on success on your own terms? There is this template that a lot of people unconsciously follow of if I get more success, more money or more fame, then, I will be happy in life or then I will have done life well.
Kris Kluver: It’s broken thinking to me. These are just my theories on this, but I believe that we’re the first generation in history, since the dawn of time, that doesn’t have to invest most of our energy in not dying. We’ve got unlimited water, we have almost unlimited power, we have issues absolutely, but for the most part, we aren’t worrying about starving or people coming over the hill and killing us or people coming over and stealing all our stuff.
Think about it, it’s been within the last three generations that’s happened. New generations never had the experience with world war, with mass famine, and for the most part, if you’re in this country, you are so insulated that you don’t see that. So, because of that, I think that our parents and our grandparents have been ill-equipped to help us think differently.
We’ve been totally wired for more, more, more, more, need, need, need, need, stuff, stuff, stuff, stuff. Because historically, somebody was going to steal all our shit, or we weren’t going to have enough. The fact is that we’re transitioning that thinking, but we’ve handed over our thinking to our parents, to our peers, to our advertising, but we haven’t taken control of ourselves.
That’s why I start in the book–with that very idea that you can determine what success looks like on your terms first and foremost. So, if you decide that means that I want to go to every one of my daughter’s ballet recitals–win!
If that means that you want to live in a simpler house, and you only want to work 20 hours a week, right on. If it means that you want to be famous or you want to make more, you can do those things. The challenge is that if we don’t know what we’re going for, there’s no way you’re going to get it.
Nobody goes on vacation and says all right, “Honey, let’s go on vacation,” then just goes and gets in the car and starts driving. “Well, do we have gas? Do we have any clothes? Do we have direction, do we have the kids? Do we have bags?”
But that’s the way most people live their life and it is just mind-boggling to me. If we can help people figure that out. The way that most people can live that life, whatever they choose, is through their own private business.
Charlie Hoehn: Could you define what a solopreneur is to the layman who maybe hasn’t heard that term?
Kris Kluver: I define solopreneur as an entrepreneur. In essence, this is somebody who wants to be in charge of their own life, control their own business and work, most likely, by themselves. They may contract with somebody to help them with their books or they may contract to get some help with their marketing or things like that.
In essence, it’s somebody who is kind of like a gig worker. They are truly accountable for who they choose to work with, when they choose to work, what they choose to do, and how they get compensated.
Success on Your Own Terms
Charlie Hoehn: How do we get to the place where we’re thriving and really achieving success on our own terms?
Kris Kluver: It would be my opinion that first, you have to define what success looks like for you. You have to define what your true north is, who you are in your soul, and then define where you’re going. You have to know crystal clear, but you may need some ideas.
On that note, for years, I owned a content marketing and social media management company where we worked with people from New York to Indonesia. I had a lot of younger people working for me and a lot of people say, “Oh, the millennials, they’re a bunch of slackers and they just whine. I don’t know why they’re entitled.” I would argue, I think that a lot of millennials are some of the hardest working generations we’ve ever had, if you provide a good why–if they know their why. If they know why they’re doing something and they buy into it, holy smokes, those guys will dig in like nobody’s business.
As a solopreneur, if you know what you want, if you know where you’re going, your true north of what matters to you, and then you define the next step of where you’re going, it’s going to help you get there.
In the majority of the cases, I would argue that almost never does a small business or solopreneur or gig worker fail because they aren’t great at being a technician in that business. If they’re a writer or an accountant or a therapist or whatever it may be.
Almost never do those people fail because they’re not good at actually performing the task. The reason that they fail is that they go in blindly, hoping that they can just go build a business. One of the key concepts in the book that I’m really pushing is to transition people’s thinking so that they can start to think more as an investor and that they’re investing in their business. What does that look like? What’s it going to take? Be honest, be pragmatic about it.
To think more as a manager, you’re going to have to manage yourself in the processes and actually make sure that the work gets done. You’re going to think of it as a business development person. Who is going to drive sales and success?
Then lastly, as the technician actually operating within the business. It’s those first three steps that if you suck at one of those, you could go right off the rails and not even realize it before you’re in trouble. But I promise that this is the most abundant time ever, it has never been easier. In the book, I go through a step-by-step process with lots of exercises about how people can actually go in and test this, and start building that, and how to create a full board of advisors that aren’t going to cost you any money–from peers in your network or peers in the industry, to finding a good banker, finding a good accountant, finding a good attorney, and finding a good insurance person. In some cases, they’re solopreneurs and their whole job is to make sure that people like you are successful.
How do we do that, and then how do we very intentionally figure out where we want to go? Build the plan, test it, research it, become an expert, so that then we can very safely and very intentionally transition so that we’re very, very successful when we go and launch.
Dude, yeah, you want to start a business, I get it. Let’s figure out how we’re going to do that, don’t just jump in the car and start driving because you’re going on vacation. Where are we going?
Charlie Hoehn: Tell us a bit about the stakes. What does it look like? What happens if, let’s say, a fitness trainer, somebody who is a solopreneur and starting a business, gets it wrong and doesn’t do what you prescribe in your book?
Kris Kluver: Well, if people choose not to do this–and unfortunately, most of the people who are thinking about it or dreaming about it won’t do anything. Then they’re going to become a victim and they’re going to be stuck in the doom loop of their job. I call that office hell. For those who choose to actually go out on their own and try and do it the best they can, the statistics say that 50% of those people will not fail. But 50% are going to fail.
The challenge is that you’re going to see that 50% failure rate about every five years. The problem is rarely are people going to thrive. What does that specifically look like? It looks like bankruptcy–it could look like divorce–the worst health impacts that you can imagine. If you think about the stresses associated with that, there are all sorts of negative things that can happen.
It could be beautiful, wonderful, and exciting when you get there, but that road from starting to getting into it, that’s a whole different set of skills than actually executing the task, the product or service that you’re selling.
Step by Step
Charlie Hoehn: Absolutely, Kris. So, let’s make this even more real. I’ll share a little bit of my story and my journey as a solopreneur.
Kris Kluver: Right on. Let’s see where it goes.
Charlie Hoehn: Cool. I’m an author myself and I’ve written a few books. One of which, not only did pretty well, it continues to create opportunities. My book was about how I went through burnout and a really hard period of overwhelm and stress and anxiety and how I tried everything for two years and nothing worked.
And then I started adding play back into my life, like the way kids play because kids and teenagers have stressful existences too. But they play as a release valve and as soon I started doing that, within less than a month, I was completely symptom-free–totally back to normal.
I am at a point now where I am strongly considering doing group workshops, where it is just a day, maybe two-day, workshop where we practice these principles and it is group coaching. Now I’ll tell you I’ve experimented with little things in the past like courses and stuff and I have gotten by, but I fall into the category of somebody who’s been in business for a while but hasn’t really thrived.
So, what would you say based on your book? Do I need to define success on my terms first?
Kris Kluver: I so embrace and love your idea of play. I too work with high dollar leaders. I am an adviser to billion-dollar CEO’s. From solopreneurs to billion-dollar CEO’s, and I have a lot of $100 million leadership teams I work with, but I get a little wrapped around the axel sometimes about how important I am. I actually am at the point now where my wife paints my toenails and buys me superhero underwear just to remind me. I am not kidding.
For you, I think the most important thing is to start to really define what great looks like. If you know where you want to go and you can have a visualization of what spectacular looks like for you in three to five years, dude, you’re halfway there. Have it crystal clear what those retreats look like, how many you’re doing–are they adventure-based, are they overseas, or are they local? Is it in Bailey, is it up in Vale, what are those things that really, really float your boat?
Define that and I firmly believe that the universe will line up and give you exactly what you want, but we have to know what we want. If I were in your shoes, I would start with defining crystal clear who you want to work with. The more you can say no, the more you can narrow it down to who specifically are the people you want to work with, you’re going to be able to be laser-focused on how you approach them and how you go after them. I talk about that in the marketing component of this.
If I were in your shoes, I would start with that. Then second, and this is recommended in the book, I would start finding out who your peers are in that space, or that are even kind in that space, and call them and say, “Hey dude, I would love to start doing workshops in this kind of space–doing this and this and this. If you were in my shoes, what would you do?” And then shut up.
Remember, the good Lord gave you two ears and one mouth. There are lists of questions that I ask people but start out with other people in your industry. In your case, it is not like people across the street do what you do, but there are people that do retreats all over the country. Start finding those people and ask them what worked for them and what didn’t.
We get our own way. So, on that note Charlie, I believe that extraordinary lives in the unreasonable. Fucking be unreasonable, dude. Go out and get it and dream big and go ask those people and if somebody says no, well maybe they are scarcity-minded. Let them go–there are a lot of people out there who can help you. Keep asking, and you may find people that say, “You know, I love that idea. Would you want to do one with me?” But again, that’s what’s going to get that started for you.
Charlie Hoehn: It gives me a sense of relief, because I know I can lean on others and start at a crawl and then walk and then run.
Kris Kluver: Then they’re going to open up so many doors. They’re going to open up doors about who you should talk to from a financial basis. They are going to open up doors about who you should talk to for potential networking, the types of structures you should do, the type of insurance–all those things. But it is a matter of being curious and listening. To that extent, I don’t care who you are. You can’t do everything on the planet well, no matter who you think you are.
Some people could do a lot of it and that is awesome, but those people get in their own way more than anything. I would encourage you to think of yourself as the composer and the conductor of a symphony. You may be a virtuoso who can play every instrument, but you know what dude? You can’t play every instrument at the same time. It’s your job to figure out what the music is, what it is going to look like, what the flow is going to be, and then you coordinate that flow.
It could be through some of your contractors, it could be through a lot of what you do, but that’s where, as the manager, you have to manage that process. You can’t do it all. There are some tools that I created called the delegation matrix and some other tools to help people define what those things are that they can let go of. What is going to be the highest and best use of your time, where you get the most value, the most juice for the squeeze?
Swing at the Good Pitches
Charlie Hoehn: Tell me more about some of the big ideas in your book, or maybe something that might surprise a listener that they’d find in your book to help them in their path towards becoming a thriving solopreneur?
Kris Kluver: Two things–one is in many cases I am going to encourage people to be very, very open and candid with themselves. Have that deep conversation about whether this is the right fit because I consider it just as big of a success if somebody reviews it, digs in, looks at it and says, “Wow, this is not a good idea. I shouldn’t do this.”
The education, the paradigm shift that somebody has gone through when they are thinking is awesome. It means that, holy smokes, they’re realizing that this isn’t the right fit. Maybe they are not wired for it or maybe it is just this opportunity, but what that says to me is that, “Boom, we just saved somebody who wasn’t going to be in that 50%. We just saved somebody who is going to lose their entire life savings, or who is going to get divorced, or who is going to end up in the hospital because of stress.” To me, that is massive.
That’s the first thing and the second thing is along that same lone. As people go through this, they may think that their original version of what they thought success was going to be for them, and for the business they wanted to start, that was their one shot. It’s like, “Oh god, I have got to make this work, or I am never going to get there. I have got to do this.”
That is not the case. I am going to beg and plead with them not to believe that. I literally have gone through this entire process that I teach hundreds of times, and 90% of the businesses that I thought were spectacular–that I thought were just brilliant–were bad, or it was close, but it wasn’t a great fit. With that in mind, I want these things to be total no brainers for people. I want it to be that when they do this it’s like, “Oh my god, this is what we should be doing.” Then you know it’s a good fit.
If it is close, but it’s like, “Nah, it’s not quite right,” don’t worry about it. You’ve turned on all sorts of new switches in your brain and you are going to start to see opportunities all over the place. It is through that you are going to end up finding out what’s really lights you up, what really turns your crank.
Being in Omaha, I’m a shareholder in Berkshire Hathaway, which is Warren Buffett’s company. They do big shareholder meetings that they call the Woodstock of Capitalism, and I go to that every year. Warren Buffett’s number two, his name is Charlie Munger, and Charlie, in my opinion, is just as smart as Warren and just as big a deal. He’s a little bit older, and he’s kind of a curmudgeon and gruff. I love that. He’s very, very blunt.
At one point, listening to Charlie talk in the stadium where they do their shareholder’s conference, he said, and I quote this in the book, “People think that we are really brilliant. That we’re some kind of soothsayers or gurus, we’re not. We read a lot of stuff. We look at a lot of deals. When we get a good deal, we look at it, we research it, it’s like, ‘Huh, it’s a good deal,’ you know what? We do those deals. We only do no brainers.”
I know that sounds really basic, but the problem is that when somebody who is really smart wants to start their own business, they can rationalize their way into anything.
Just because they can, doesn’t mean they should. The intention is, is it a no brainer? It’s like, “Oh my god, I love this. This is going to be a home run. This is going to be awesome. I don’t know everything yet and I might get clobbered here and there, fair enough, but for the most part yeah, I got this.” That is where we want to get to.
Charlie Hoehn: In the HBO documentary about Warren Buffet, he talks about how his investment strategy is similar to Ted Williams hitting strategy. Ted Williams is still widely considered the greatest baseball hitter of all time and Ted Williams whole strategy was–don’t swing at bad pitches. Swing at good pitches and nothing else.
Kris Kluver: And that’s it. So often people think, “Oh my god, this is my one chance to get, this is my one shot.” And it is so not true. It is the first time that maybe they’ve looked at it, but if they go out swinging because they are swinging at bad pitches, they’re going to be burned. They may never ever, ever want to go out again. The problem was they just swung at the wrong pitch, but nothing out there teaches us how to research.
What is a good pitch? What is a good fit? How to build a pro forma? How does this have any financial viability? Are we taking into account how much the government is going to take, how much it costs for taxes, for insurance, for our suppliers? Have you factored that? No, people are just, “Okay, we’re just going to get in the car and drive–we’re on vacation.” Okay, where are we going?
Shifting Definition of Success
Charlie Hoehn: You force the reader to really ask themselves the tough questions to make sure they are going down the right path.
Kris Kluver: I hope that is the case. Going back to the idea of millennials, it is about asking the right questions. I think we are in a paradigm shift about how we look at what success is. I grew up going to school in the 80s and 90s, where it was about how much Pabst Blue Ribbon and cheap bourbon could you drink. It was debauchery. It was the era of cocaine and big hair and things like that.
Now it is tiny houses, and twenty-hour work weeks, and craft beer, and adventure. I think it is a different definition of success, and it can be on your terms. You know for me and my wife, after I went through my hip and my knee replacement, we went through and really defined what success is for us. It is different for most people. We met in Chile traveling and we love to adventure travel.
We also love doing what we do. We feel like the luckiest, most fortunate people on the planet, man. Now, we very intentionally designed and built our lives so that we take three months off a year doing adventure travel, and we get to work with people we love and help them. And candidly, we’re making more money than we ever have. I am in the best health and physical fitness I have ever been in, because I made that a priority. Since the hip and knee replacement, I have lost close to 100 pounds. I was able to complete two ultra-marathon trail runs this year. So, it’s absolutely ridiculous what is possible when you start putting intention behind it and defining what you really want.
A Personal Example
Charlie Hoehn: Can you tell a story of somebody who’s gotten a lot of the ideas in your book and how it transformed them? What their life was like before, how you came in and helped them, and what their life was like after?
Kris Kluver: My wife was an accountant for a venture capital firm in London, and she was good at it, but she didn’t really love it. It was okay. In her particular case, she ended up completely transitioning to a different career, but it was over a long period of time. It was a long journey. Through the process, she ended up finding that she really wanted to be a couples and family counselor. Counseling had helped her, and it helped us. It helped her with some of the challenges she had when she was young, and it was really important to her.
She ended up going back to school and we had to figure that out. Then she ended up getting her degree and then she basically had to work for 3,000 hours under somebody else. So, she did and then she decided to go out on her own. She’s a very smart person.
She had a background in accounting with a venture capital firm. She had a master’s degree in couples and family counseling, but there was nothing out there that had taught her how to actually start her own practice. There was nothing out there. We went through and slowly built her whole model. She vetted it, and we built a plan for her to transition.
Long story short is that she now makes about twice the money she did as an accountant, working about twenty hours a week. She’s an ultra-athlete, so she does a fair amount of training, and has the time to do that, and she loves her life. She gets to help people in ways that are really fulfilling. She is choosing to even move on forward and she is starting to look at couple’s coaching and individual life coaching and things of that nature. It is really exciting to see, to have a front-row seat and see how that has gone.
Charlie Hoehn: What is the best way for listeners to either follow you on your journey or potentially connect with you if they are running a business, they want to get your input, that sort of thing?
Kris Kluver: On that note, I am more than happy to help people in any way that I can, and I encourage people to please reach out. I will get back to you as soon as I can. I really am wicked about managing my time, but I do try and follow up on all my emails. The primary place they can find me is on my website, which is aspiringsolopreneur.com. My wife and I also have a YouTube channel called solopreneur-life.com where we talk about some of the couples retreat stuff we do, but mostly it is a place intended to celebrate the life of a solopreneur. Then the third place is LinkedIn, and feel free to connect with me there. I have a couple of other social platforms, but candidly, I am not that active on them anymore.
A Challenge from Kris Kluver
Charlie Hoehn: The final question I have for you is to give our listeners a challenge. What is one thing that they can do from your book that will have a positive impact on their life or their business this week?
Kris Kluver: Go to The Aspiring Solopreneur, and there is a free video that talks about identifying your LCG–your life-changing goal. It’s an exercise that takes you through two steps, and that shouldn’t take more than 20 minutes, that will help you dig down and define what is that thing that is just extraordinary in your life? What is that thing that’s like, “Holy smokes, I have been dreaming about that forever, but I didn’t realize it.” It will help you define where is it you want to go and how you’re going to get there.
Rank #4: The Search for the Perfect Protein: David Minkoff
Rank #5: Keen on Retirement: Bill Keen
Bill Keen is the founder and CEO of Keen Wealth Advisors and has more than twenty-five years’ experience helping people plan their retirement.
When we think about retirement, most of us think about what our lives are going to look like after we stop getting a regular paycheck. Yes, we do need to think about investment and financial planning, which Bill walks readers through in his book, but there’s more to it than that.
We also need to think about the emotional and psychological aspects of retirement. For example, what is your day-to-day life going to look like? Have you really stopped and thought about what being fulfilled in retirement looks like to you? Bill helps readers walk through all of these questions in his new book, Keen on Retirement: Engineering the Second Half of Your Life.
Bill gives us some insight into what successfully planning for a retirement you love looks like.
Nikki Van Noy: Bill, you have described your career on Wall Street as the first half of the movie Wall Street combined with the movie, The Pursuit of Happyness. Can you tell me a little bit about that?
Bill Keen: The thing that I relate to, Nikki, in this is that Bud Fox went to Wall Street and he tried to make his way with no family money, no influence, no resources–he had a dream and a vision to go out beyond the suburbs that he grew up in and to try to make it. That was something that I related to because I’m from Kansas City, Missouri and I grew up with not a lot of influence, no family money, no resources, and no contacts, but I knew that I wanted to be able to understand finances and to be responsible.
I wanted to be able to go out and stake my claim. One, so I could take care of my parents in their later years and two, so that I would never have to experience some of the anxiety that I saw in them.
Now, The Pursuit of Happyness is an interesting one as well, because it speaks and it talks of a gentleman that really had nothing, trying to get started. And in The Pursuit of Happyness, the gentleman in that movie worked at the same firm that I worked at–Dean Witter.
A lot of the things that I saw him doing were things that I had gone through myself in that very same firm. He was able to stake his claim and make it in the industry. When someone asks me about myself starting out, I say it’s a cross between the first half of Wall Street and The Pursuit of Happyness.
Nikki Van Noy: Were you always able to be pragmatic in terms of getting yourself set financially and planning for the future?
Bill Keen: I remember sitting on my father’s couch in a very small apartment, waiting for his unemployment checks to hit the mailbox. That was back when they actually did hit the mailbox, and not get direct deposited. For whatever reason, at that age, I internalized the anxiety. It was a tough time back then in the 70s and he had a difficult time with work. We didn’t know necessarily where the resources were going to come from wee- to-week and month-to-month.
For whatever reason, I was a young person who experienced anxiety right along with my father. I attribute a lot of the focus and determination and intentionality about where I went with my life and career on that. But I can tell you at the time, it created a lot of stress and anxiety in myself. I wouldn’t trade it today looking back, but it caused me to want to seek out being able to understand how the economy works, how finance works, and how to be responsible.
This probably wasn’t healthy for someone of my age, but also to be able to provide for my family, for my father, for my mother, and for others–I was not pursuing some wealth dream but pursuing just peace of mind for them. Peace of mind and the ability to be not be riddled with anxiety around finances.
Great Aunt Nina
Nikki Van Noy: Bill, on a personal level, was all of that education and attention and intentionality able to combat the anxiety for you?
Bill Keen: Well, you know, I had a vision and I had a mission, and that that helped, but no. It was very confusing and somewhat chaotic as I was growing up as a young guy, looking toward the future, but it wasn’t until I got out of the house and got working on my finance degree in college that I could start to see things crystalizing. I could start to really see how things played out and how things worked in the economy.
I also had a great-aunt who was born in 1901. She has passed, but she lived to be a hundred and she died in 2001. As a young person, she coached and counseled me on Wall Street. In fact, there’s a candy store called Russell Stover Candies. She was friends with Russell Stover. She held a high position at a well-known department store here in Kansas City called Emery, Bird, Thayer. She was a woman of means, and she was kind of ahead of her time. She coached and counseled me on what investing was like.
All this collectively brought me into opening my first brokerage account when I was sixteen, and still in high school. Then working toward college and beyond with a mission and a thought about what I wanted my life to look like. I was still very young and inexperienced, not knowing how it was going to play out, but I did have a mission. I was very grateful, and am even today when we meet with clients and their children and grandchildren.
For me to know what I wanted to do at such a young age, I look at that as quite a blessing. Of course, I have five kids as well. It’s nice for me to watch them try to figure out and find their way in life.
Nikki Van Noy: I’m intrigued by this idea of your aunt as an influencer because, based on her age, she must have been a young adult at the time of the depression. Did her experiences with the depression inform how you’ve come to think about money and saving and planning for the future?
Bill Keen: It’s interesting because she didn’t focus on those times. Now see, I was born in 1968. By the time she was coaching and counseling me, and mentoring me, we were into the early 70s. We were forty years beyond the Great Depression years. Imagine being born in 1901 and not even having the automobile and then see a man go to the moon and what we had when she passed in 2001.
It was a fascinating one hundred years of advancement in our country and in the world that she was able to see, but she didn’t focus on the depression age and scarcity. Scarcity was not something she focused on. She handled investments, she owned stocks, she also owned bonds and CDs. Some folks we see from those generations, or even generations nearer to us than that, are very fearful.
She wasn’t like that. She was someone who went out, staked her claim, and worked her whole life in a very productive position. In the book, there’s a picture of her meeting with two other executives. There also is her business card from an iconic department store here in the greater Kansas City area that any of our readers will see, or listeners from Kansas City would remember.
It helped me that she had a more abundant mentality as opposed to a scarcity mentality.
Nikki Van Noy: It is incredibly powerful to me that someone who actually lived through the depression was able to come out with this sense of abundance.
Bill Keen: Yes, well, I think that she got to see how the story ended. She got to see that even the Great Depression was a temporary situation. She had the resources to make it through the Great Depression. She wasn’t overly leveraged, she didn’t have debt, and she wasn’t buying stocks on margin.
Before and during the Great Depression, you could put about 5% down and borrow 95% to buy stocks. Then we come to find out, the FCC wasn’t even invented until the early 30s, after the depth of the decline in 1929.
People that weren’t even being looked at were buying stocks on basically borrowed money because there was no regulatory environment. Many of the stocks were fraudulent, but for people who owned good quality investments that were not over-leveraged, they made it through those times and the economy, and the markets recovered and prospered.
I believe that because of her journey and because of her history and hard work and diligence and living within her means, that she had that perspective that helped her not live in complete scarcity and fear at the time that I got to spend with her.
Gosh, remember, in the 70s, she was already seventy years old, but I got to spend twenty-five or so really quality years with her and learned a ton. In fact, again, I mentioned her in the book, I also have a whole podcast episode on Keenonretirement.com–Keen on Retirement on iTunes and Spotify, and all the other platforms where I talk specifically about great-aunt Nina.
From Wall Street to Retirement Planning
Nikki Van Noy: Tell me how you made that leap from Wall Street to helping people with retirement planning?
Bill Keen: Yeah, I got out of college and I worked for a company in Kansas City founded by James Stowers called Twentieth Century. Twentieth Century was a mutual fund company and I was able to get my foot in the door. It’s a wonderful company that is still around today. His family now has gone on to endow the Stowers Institute for Research and they have literally donated billions and continued to donate billions of dollars to cancer research and other disease prevention research.
I spent a year there, and at that time at this particular company, it was a no-load mutual fund company, which means we could accept orders from clients, but we couldn’t give advice. I realized early in the journey that I would see clients calling in and doing things that were not in their best interest. They were selling investments at the bottom of the markets, they were wanting to buy in at the high on hype, and I was seeing that happen, even at that age.
I needed to be in the part of this industry where I counseled clients. I left that company and cold walked into brokerage firms. That’s when I was hired at Dean Witter about a year out of college. It was interesting because here I am this young kid from Kansas City. Once you pass a couple of exams, they were going to ship me off to New York and I would be working in the south tower of the World Trade Center on the 83rdfloor.
I was somewhat of a fish out of water, but I was enjoying it and taking it all in. I was there just a month after a terrorist drove a truck into the parking garage of the World Trade Center and detonated a bomb. You might recall that in 1993.
I was there off and on for approximately a year and it was an interesting time to be out there. I stayed right across the street, in a high-rise condominium, looking out my window at Madison Square Garden on 31stand 7thavenue in New York.
I got into retirement planning. To expand on that, it was really more of the old traditional stock brokerage firm that was, unfortunately, one of the only things available for your general investor.
We had mutual funds and a myriad of different investments there, but there wasn’t any financial planning, for folks when we looked at retirement–what will the tax ramifications be, what will health insurance look like, do I have the will, do I have a trust, what happens to me if I pass away? Will my kids, my spouse be taken care of–my grandkids, and charities? All that type of holistic financial planning was not on the table back then.
It was only focused on investments. That is something that has played out much differently in the last decade or two as our industry changed. This all was what attracted me to found Keen Wealth Advisors as a registered investment advisor and to create discipline in the process and the holistic planning process that we have in place at our firm today.
Nikki Van Noy: What things do you want clients to be thinking about outside of investment as they begin to plan for retirement?
Bill Keen: Well, I think that it goes way beyond the numbers. So many people look at retirement and investing, and taxes, and different aspects to their financial planning as just numbers–the numbers are very important. The numbers have got to be right. Things have got to be accounted for, precisely and accurately and planned for. Of course, they do. But it goes way beyond the numbers when you’re really looking at someone’s plan. This is something that I’ve learned and evolved in my career. I’ve now been on a professional journey for almost twenty-eight years and I’ve also lived life up until age fifty, almost fifty-one now.
You start to realize that time has become a priceless commodity for myself and also for many of the clients that I talk to. I think about age fifty is a break over point for a lot of people, when they start realizing–not to be morbid–you start thinking, wow, I only have, if I live to a normal life expectancy, maybe I have thirty-five more summers, thirty-five more Christmases, thirty-five more birthdays.
Again, not to be morbid, but we all have an end date. As you get older, you start to realize that now time is the priceless commodity. That’s not to say we don’t take care of our affairs and our business, of course, we do. But we have to start looking at how we want to spend that priceless time, and how we want to maximize it for ourselves and for our families and the people that we love, and the legacy that we want to leave. However, that looks different for each person.
When to Retire?
Bill Keen: From a financial standpoint, when is the best time to retire?
Nikki Van Noy: I believe it’s 70.
Bill Keen: Okay, this is a great answer that you have. Let me tell you, the most common answers that I received when I ask that question and I will admit, it’s a trick question. I get sixty-two because that is when you can start receiving Social Security. Of course, it would be a reduced amount from your full retirement, but you can start receiving it.
Others say sixty-five because that’s when you can receive Medicare, which helps big time when you’re retired with your medical care and insurance. Some say fifty-nine and a half, so pulling it back a little here, because that’s when you can access your retirement accounts without a penalty. You can get to your retirement accounts without a penalty before fifty-nine and a half, but it’s a little cumbersome.
I also hear age seventy because that is the latest you should start taking Social Security because it doesn’t go up any further after seventy. Also, at least under current law, seventy and a half is when you have to start taking money out of your IRAs. All of those are legitimate answers.
But occasionally, someone will say, from a purely financial standpoint, the best time to retire is never. Believe it or not, that’s the correct answer. From a financial standpoint, you could always work another year, you could always save more money, there’s always a reason to justify putting off retirement, and have another year of saving and investing, and another year of not spending.
I don’t want to encourage anyone to retire before it’s prudent, but I believe that when you have the resources to retire, you should consider doing so. There’s a lot more to life than saving and investing until your dying day. I’ve seen this, I’ve witnessed this, I’ve been in over 15,000 client meetings in my career. I get to see the themes that come out, I get to see the dangers, the opportunities, the strengths, and the emotion. There’s a crossover point financially, mentally, and emotionally when you know it’s time to leave the saving phase in the working time of your life, and to start spending some of your resources and enjoying your time, working on your health, eating well, exercising, and spending time with your loved ones.
I’ve seen it many times and it’s really fun to watch people walk through that process, get up to that point, make one of the biggest decisions they’ll ever make in their life, and enter the next phase of life by retiring.
It Is About More Than Just the Money
Nikki Van Noy: Since selecting retirement age has to do, not just with financial elements, but also mental and emotional elements, how do you help people project ahead of time when that correct point to aim for will be?
Bill Keen: At a minimum, we recommend that folks sit down at least ten years prior to a potential retirement date. So many of us in America, even if we are employed and we work for companies that we’re saving money in 401(k)s in retirement accounts, and we’re living within our means and we’re doing the things that we should be doing to be prudent and to plan for the future, so many of us are on autopilot.
Again, I see age fifty as this kind of wakeup call where people start to say, “Wait a second, I can imagine being at a point in time in life where I don’t have to work anymore.” For the people that we work with that I work with, there are people that started with nothing. They’re like me, they’ve lived within their means, they worked hard, they were intentional, they were disciplined, and they delayed some gratification over time.
It’s sometimes hard for those folks to even imagine that there could be a day that they do not have to go to work anymore because they’ve saved enough, and they’ve invested enough that their assets will support their lifestyle until the end of their lives. I recommend strongly for anyone that’s on this path if you’re fifty or over, you should be doing the things that we talk about in the book. You should also be sitting down with someone, in my opinion. If you want to try to do this on your own, you can, but it’s sometimes very difficult to hold yourself accountable. It’s also very difficult to see the blind spots that you might be missing in your own plan.
I’m biased in this. I believe that someone should find a fiduciary advisor or advisory team that has a very disciplined process and a specialization in retirement, that’s going to help them see around corners they otherwise couldn’t see around and that could be ten years out or more.
That comes to money, and taxes, Social Security, Medicare, all those things, but it also comes with thinking about what you are going to retire to, not what you’re retiring from. So many get that confused. We’re just going to retire from.
We have one main question that we pose, and we’ll have both spouses present as much as possible because we want to make sure that they are on the same page with this. What will life look like and what will we retire to in retirement? I can expand on some of the things that people retire to, but the preparation and the thinking and the emotion is just as important as the preparation for the monetary assets and the details.
Nikki Van Noy: Why is the psychology and emotion of this so important?
Bill Keen: What’s your minimum investment to work with someone? Because a lot of these firms have a million-dollar minimum or multimillion-dollar minimums, and I say my minimum is that someone needs to be grateful and humble on most days. What that means is basically a nice person, and just being committed to being responsible for their retirement, their planning, and their wealth building. That’s the minimum.
It is not a monetary minimum, because I am staffed in such a way that we can help anybody that comes to us with those attributes. Think about working with engineers–engineers fall into that category. They are naturally planners. They are typically folks that have worked hard, lived within their means, and they’re planning oriented. They are process-driven. They love measurement. They have sold their brains over the course of their careers to others who needed to hire them because that is where they specialize.
So, they understand that they need help outside their field of expertise. So, while all my colleagues around the industry think we are crazy for working with engineers because they are so detail-oriented and demanding, I disagree. We love working with the engineering community. To tie that in with your question, you would think engineers are some of the smartest people on the planet. Without them, many of our technological advancements–power plants or water systems–none of it would be here.
Engineers actually need help with retirement planning and investing. How could you possibly get an engineer to talk about his or her emotions? The reality is, it is every bit as important for them to sit down and get conscious of the fact that they have never been retired before. So, we do not know how we are going to react to things like spending every moment with our spouse.
There is a funny little cartoon that we had made that says, “I said for in sickness and in health until death do we part, but not for breakfast, lunch, and dinner.” I see this a lot when people who have been very successful financially, but now both spouses are on top of one another, figuratively, all day long. They have to figure out a rhythm for what are they going to be doing in their life with their time so that they are not driving each other crazy.
They love each other, they have been married forty years let’s say, life is good, but they have to come up with a daily rhythm for how they’re going to do things and discuss it ahead of time. What will our days look like? Are we going to babysit the grandkids? If we commit to babysitting the grandkids on Mondays and Tuesdays, are we going to allow that to evolve babysitting the grandkids all day, every day for the next three years?
These are things that we have to talk about upfront, because one might think, “Yes!” and the other might think, “My goodness no, we retired so that we can travel and pursue our interests.” Because it is not about the money at this point. We are talking about life now.
Visualize Your Retirement
Nikki Van Noy: It sounds like what you’re asking people to do is really visualize their day-to-day life in retirement.
Bill Keen: Without question, and I would say that a competent quality financial advisory team should be asking these questions of their clients. We are in a very unique situation in that folks come in and they’re laying out their financial lives to us.
We should be very guarded about our finances. We shouldn’t talk about things–it is not a comparison. We should keep these things very private, but to get help, folks have to come in and lay out their information to us. We are asking things about their family trees. We are asking things about where they lived growing up. We are asking, “Did you have resources, did you not? Was it stressful?” Much like my story. We’re you the oldest, the youngest, the middle? Were you one of twelve or the only child?
Well, why does this matter? Well, these things do matter, because I need to know, and my team has been trained to need to know how someone got to the point where they are sitting across the table from us. What has gone into creating their view of the world and how they interact with their family, their money, their situation, and their health. We need to see if they have kids that are going to be relying upon them, or maybe grandkids. Do they have parents that are going to need to be supported by them?
I see many in the sandwich generation today. I am frankly one of them, where they are supporting parents and children at a certain point in time. Do you think that doesn’t go into the retirement planning numbers? Of course, it does. These are things that we need to understand upfront. So, if a financial adviser is doing their job, in my opinion, correctly, they are not just talking about money.
They are getting very personal with the people they are sitting across the table from. The advisor needs to understand that to folks sitting across the table at this very moment, this conversation is everything to them. This is their entire life. For us to be able to advise somebody how to invest their money, and how to tax plan, and how to do estate planning, and wills, and trust, and timing, we have to know what got them to where they are today and how they’re wired.
If we can do that, it sets the stage. If they are married, now we’ve got both people at the table. We start hearing both stories and then we can roll into what their vision is of retirement is and what it is going to cost. It is a natural question. We need to know what you want to do because we need to figure out what it’s going to cost you so we can plan accordingly.
It sets the stage for real personal conversations that I don’t think many financial advisers are actually having. I don’t think they are going that deep. I think it is super important and it is very personal to me.
Plan For What You Can Plan For
Nikki Van Noy: I’d love to hear a story about a client you have. Your favorite story about how you really created an incredible second act of life.
Bill Keen: Not long ago I received a call in my office and when I looked at the caller ID, I saw the name of a client’s husband, and although we had a great relationship with both spouses, in this case, we typically talked to the wife.
I have known these clients for over twelve years and the husband had never been the one to call me. So, he’d set up an alarm and before I picked up the phone, I sensed something might have been wrong. As it turned out Nikki, the wife had been diagnosed with a rare form of cancer literally out of the blue and given three to six months to live.
While this is tragic news, I have been doing this a long time and these things aren’t unexpected. Of course, they are unexpected to the folks that are going through it, but if you look at a pool of people, we know that some of us are going to have to travel tougher journeys than others. If there is anything, I have learned over the course of my career is people deal with hardships in life and we never know how our individual journey is going to play out.
A couple of days after receiving this call, I found myself sitting at the kitchen table in the client’s home with one of my financial planners and wanted to make sure that all the aspects of this client’s financial plan were in order. This particular husband and wife had retired when they were in their early 50s.
When someone retires in their early 50s, in some cases before, but not often, it is always a point of concern, because of the longer time period that they have to make their assets lasts. So, with a normal life expectancy, the earlier you retire, the longer your assets have to last. It’s just common sense. When someone retires in their 50s, a lot more work must be done upfront to ensure that they will have the resources they need to last the rest of their lives. The husband had a nice pension and the wife worked as an engineer and built a retirement portfolio. They had a farm and they had the resources to retire earlier and pursue their passion.
They were deeply involved in their church and did mission trips and wanted to go around the world and they did that. So, eleven years after having pursued their passion and having done the things they wanted to do to maximize their time, the wife received her diagnosis. I have been through this many times with clients now at this juncture of my career, and they always look at me in the eye and ask the same question, “Will my spouse be taken care of when I am gone?”
They are worried that someone will take advantage of them or the scammers will come out of the woodwork and find ways to get their hands on their assets. They are worried that somebody might come and maybe offer to buy the farm with a low offer. There are just so many things.
That client has since passed and from a financial standpoint, the spouse doesn’t have to worry about anything. He has a team of professionals that protect him. Anybody that calls him or talks to him in any form or fashion, he calls us instantly, or forwards the emails.
I think it denotes the power of planning and living life to the fullest–leaving everything in the field, I like to say. We don’t need to be shy about pursuing the things we want to do.
Nikki Van Noy: This idea of having professionals there to rely on in those moments when you are alone and don’t necessarily know how to handle a situation strikes me as incredibly powerful. That’s security.
Bill Keen: I believe it is. That only comes from a personal relationship and from knowing somebody and understanding their family dynamics. Being current with them, being communicative, and knowing where someone stands at all times. I think that’s very important and a theme throughout the book.
Personally, it is about having a plan in place at all times, so that we can control the controllable in a world where there are many things that are beyond our control. There are things that are in our control. Sometimes, having a plan and having it updated is what we are in control of. We are not in control necessarily of the outcome, but we are in control of the plan. Having a plan and being pre-committed to certain things, if X happens, we do Y and we thought about it first upfront, that creates peace of mind. That creates confidence that we have done everything we can do to control the controllable. We have been prudent–we were living within our means and we can take whatever tomorrow has to present to us.
That’s what I believe is true peace of mind in financial and retirement planning, as opposed to just how much money you have. Of course, if you have millions of dollars it makes the plan better, but if you don’t have these other things in place, it can go south quickly.
Have a Good Co-Pilot
Nikki Van Noy: Finally, talk to me a little bit about how you equate flight planning with retirement planning?
Bill Keen: Well, I know we are talking about the book launch, but I also have a website and a podcast called keenonretirement.com and it is a resource that I have made available. I believe there are nearly one-hundred podcast episodes out. It is a resource that I wanted to put out into the community.
I routinely make the comparison between flight planning and retirement planning, because I am a pilot. About ten years ago, I walked into a flight school and I said, “I talked to everyone else about leaving everything on the field.”
By that, I mean pursue your passions. Tomorrow is promised to no one–do the things that you can do within reason and within the plan. Enjoy your lives. I was saying that to folks and I always wanted to fly. I was forty years old and I hadn’t pursued it yet. I walked in there and I said, “Give me the meanest, crustiest old flight instructor you have because that is how I respond. I want experience and I want someone to tell me what they need to tell me and what I need to hear.”
Now, ten years later, I am an active instrument-rated pilot with a high-altitude complex endorsement and high-performance endorsement. I utilize my airplane to travel across the country to see clients and to go to events–conferences and such. It is something that has been very, very fulfilling. As I have learned aviation and I have learned flight planning, I started to realize that it is life or death.
In the retirement planning field, the decisions that we’re making for folks and the decisions that clients ultimately make for themselves, it is fair to call them both life and death endeavors.
You might remember the tragic death of JFK Junior? It was actually twenty years ago. It’s crazy, but time passes. Sometimes we say the days go slowly but the years go fast. Again, to my point, let’s get our ducks in a row and let’s make the most of each day that we have. Most people recall that JFK Junior was flying his wife and her sister in his private plane to Martha’s Vineyard when they crashed into the ocean. Unless you have pilot training, however, you probably don’t understand how or why it happened.
When you are flying on a clear weather day, you can look outside and see the horizon, so you always know when your plane is level. Your body acclimates to that horizon. However, when you fly into a cloud or it is a dark night, suddenly your visibility is reduced to zero and you can no longer depend on the horizon to orient your plane. So, in a car, there would be no way to safely navigate with zero visibility. Imagine driving down the road at seventy miles an hour and all your windows fog over. But an airplane has instruments that help keep the pilot and the plane right-side up. One of the instruments is called the artificial horizon and it is important. The artificial horizon is a lifesaver. The horizon is artificial, but it is still the horizon.
Flying with instruments requires a special instrument rating that is hard for pilots to get. Even after you earned it, you have to take ongoing training to maintain it and you have to stay current and proficient. The FAA has guidelines and my guidelines for my personal safety and proficiency are much higher than even the FAA’s minimum requirements. There is a ton of private pilots that just fly for fun and they never get that necessary training to even earn the instrument rating because it is difficult.
When you are up in the air with zero visibility, your mind and body start to play tricks on you. It is a little like getting seasick on the boat but not being able to see anything. Suddenly you start feeling disoriented. It is common that the plane will be turning one direction, let’s say to the left, but the pilot will actually sense that the plane is turning to the right. So, if you are not trained to fly on these instruments, you feel the plane turning to the left.
You are sensing things that aren’t really happening and you are trying to correct things and most likely making them worse. Suddenly you are in a tight turn, which is more disoriented than ever. This can happen literally in a matter of seconds if you don’t have your instruments ready and you are not current and proficient on those gauges.
JFK Junior didn’t have an instrument rating, but in the United States, pilots are allowed to fly at night without the instrument rating as long as they can see by the moonlight or lights on the ground. So, ultimately his crucial error was a decision he made to shave several minutes off his flight to Martha’s Vineyard buy cutting out across the ocean and going directly, instead of flying up the coast seeing city lights as he had done in the past.
Once he was out in the ocean, haze was reported. It was dark, and the ocean is like a black hole. He lost visibility and when the disorientation set in, he became confused. We have looked at this many times. It’s believed that it took less than a minute before he was so disoriented that he flipped the plane upside down without realizing it. When he pulled out to gain altitude, he inadvertently flew the plane into the ocean. It might sound crazy if you have never flown a plane.
The disorientation that hits you when you have no visibility is just intense. You need to be able to read and fully trust those instruments to be able to survive. It is something that I take so seriously because I am instrument-rated. If I ever were to take off in the clouds or haze or if you are flying across the country and you are in clouds, which we are a lot, many times you look out the window and you can’t see anything because we are in clouds. Imagine the job the air traffic controllers have keeping all of those airplanes separated when none of them have any visibility outside the windows.
In the same way, you should never fly blind in your financial life. When you do, you put yourself and your loved ones at risk. You have to understand what you are doing.
So, you can put a plan in place, know your situation, know your assets, know what your objectives are, know where your starting point is, and your ending point. It is your financial plan that becomes that artificial horizon that I talked about in difficult times when you feel like you are flying blind. So, no matter what happens in the economy, in the political arena, your health, the health of a loved one, you name it, your artificial horizon will keep you from making dangerous knee jerk reactions.
I believe that having a fiduciary firm guiding you is like having Sully Sullenberger as your co-pilot. I really do. I appreciate you letting me go more personal on our episode today. We can talk taxes and Social Security and Medicare, and health insurance spending–so many things we can talk about with how this comes together, but for me it is about the personal aspect to it and how folks really execute these things in the real world with real emotions and real-life playing out on a day-to-day basis.
Nikki Van Noy: Yeah, of course. I appreciate you getting so personal on this, Bill because I think getting into the nitty-gritty of this can be very dry, especially on a podcast where people want information, but they also want to be entertained. You just did an excellent job of making this so engaging.
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