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Business

How Hard Can It Be?

Updated 6 days ago

Business
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Up close and personal with the real people behind the hits and misses in Boston's venture capital big time.

Read more

Up close and personal with the real people behind the hits and misses in Boston's venture capital big time.

iTunes Ratings

28 Ratings
Average Ratings
28
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Candid, insightful and inspirational interviews

By EJSchmidt_Dutcho - Jan 15 2019
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Mike T is one of the most astute tech industry business and marketing observers I know - he is a prolific writer and social media pundit already and now (yes I am late to the party) I am hooked to his podcasts too. The quality of the guests are all solid, and they all share meaningful insights. Mike does a great job in linking his guests' upbringing and formative experiences to their successes, as well as very candid conversations about their failures and/or life choices. A great listen on a morning commute or any time available for learning and reflection.

Long form podcasting at its best

By RaphiSavitz - Aug 08 2017
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Mike's pointed yet empathetic interviews put tech luminaries at ease, as they share life stories.

iTunes Ratings

28 Ratings
Average Ratings
28
0
0
0
0

Candid, insightful and inspirational interviews

By EJSchmidt_Dutcho - Jan 15 2019
Read more
Mike T is one of the most astute tech industry business and marketing observers I know - he is a prolific writer and social media pundit already and now (yes I am late to the party) I am hooked to his podcasts too. The quality of the guests are all solid, and they all share meaningful insights. Mike does a great job in linking his guests' upbringing and formative experiences to their successes, as well as very candid conversations about their failures and/or life choices. A great listen on a morning commute or any time available for learning and reflection.

Long form podcasting at its best

By RaphiSavitz - Aug 08 2017
Read more
Mike's pointed yet empathetic interviews put tech luminaries at ease, as they share life stories.
Cover image of How Hard Can It Be?

How Hard Can It Be?

Updated 6 days ago

Read more

Up close and personal with the real people behind the hits and misses in Boston's venture capital big time.

Rank #1: HHCIB 031 Flipside Crypto Founder Dave Balter

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My guest this week is Dave Balter, Founder and Partner of Flipside Crypto, a data solutions and investment club for cryptocurrencies. Dave really is a pillar of the Boston startup community… an innovation‐obsessed builder of companies, often as a Founder/CEO but also as a Board Member, advisor, or investor.

As an operator Dave’s probably best known for Smarterer, which he founded, led, and sold to Pluralsight for $75 Million in 2014, and BzzAgent, which he founded, led, and sold to dunnhumby for $60 Million in 2011. Dave was named one of 30 Most Disruptive People in Boston Tech by Boston Magazine in 2016, was a Finalist for E&Y Entrepreneur of the Year, and was recognized as a Future Legend by the Ad Club. He co‐founded the Word of Mouth Marketing Association (WOMMA), and authored two books on the subject including Grapevine and The Word of Mouth Manual: Volume II. 

As both an independent angel and Venture Partner in Boston Seed Capital, Dave’s investments have included Draft Kings, Promoboxx, FitnessKeeper. and HelpScout. A longtime TechStars mentor, Dave also co-founded Intelligent.ly — a classroom space that helps star employees become managers — with his wife Sarah Hodges back in in 2011, and sits on the Board of Directors of Boch Center for the Performing Arts.
Jan 03 2018
30 mins
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Rank #2: HHCIB 033 Data Intensity CEO Kirk Arnold

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My guest this week is Kirk Arnold, a veteran tech industry CEO, public board member, and lecturer at the MIT Sloan School of Management. Kirk was most recently the CEO of Data Intensity, a 650-person global managed services provider of cloud-based data, application and analytics acquired by EQT Partners in 2017. Before that she held roles as the COO of Avid, CEO and President of the then publicly traded billion-dollar service provider, Keane, Inc., and Founder and CEO of NerveWire.

Kirk’s also become a kind of tech “CEO Whisperer” over the years, and serves on a range of boards from Ingersoll Rand to Cramer Marketing. She’s a huge supporter of the local innovation ecosystem here in Boston, rounding out her time at MIT with service on the Executive Committee and Board of Trustees of MassTLC, as a Board Member at The Commonwealth Institute, and on the Advisory Committee for the Massachusetts Technology Collaborative.

Kirk is the embodiment of the servant leader mentality, having started (and succeeded) as the kind sales person genuinely focused on earning her customer’s respect and not just their signature. Our conversation covers that, and a remarkable confluence of philosophies on matters significant and trivial, from what makes for an effective President to why showing up on time and prepared is a habit worth establishing and maintaining throughout your career.
Feb 14 2018
40 mins
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Rank #3: HHCIB 036 Castle Island Ventures Matt Walsh

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Matt Walsh has a pretty unique perspective on the blockchain and cryptocurrency space. If you know Matt it's likely as "the Fidelity guy" on some crypto panel in Boston or New York, or from today's news that the crypto-focused venture firm he left Fidelity to found - Castle Island Ventures - is now writing checks and open for business.

Before founding Castle Island Ventures Matt was a Vice President at Fidelity focused on the crypto-asset and blockchain space. He worked as a management consultant at Arthur D. Little before that, and later in the strategic initiatives group at Clear Channel Radio (now iHeartRadio). Matt is a proud graduate of Boston's own BC High - where he was of course called "Walshie" by "Fitzy" and "Sully" - going on to attend Babson and the Fuqua School of Management at Duke.

Our conversation began as usual with his personal story, and went on to cover the adventure of being the crypto evangelist at one of the world's most highly regarded financial institutions. You'll get his thoughts on where the best opportunities are in the crypto space right now, and on why Bitcoin still may be a bargain.
Aug 14 2018
34 mins
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Rank #4: Subscribe to my new #AskTrap Podcast!

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First of all THANK YOU for being a loyal subscriber to How Hard Can IT Be?... after a couple years of it I’ve decided to take a bit of a hiatus, and use the opportunity to create a new pod I really want you to check out, called #AskTrap.

#AskTrap solves what had become the 3 big challenges of HHCIB, namely that it took too long to listen to, too long to make, and was hit or miss in asking the questions most valuable to you, the current or aspiring entrepreneur or investor. I wanted to make something quick and easy to add to your podcasting queue in all the new platforms opening up the pod world to a bigger audience - from Spotify to Alexa and Google Home - while reducing the production burden on me so I could increase the frequency of new episodes.

#AskTrap is built on the Anchor platform, which means I can pretty much do the whole thing on my phone, wherever I am. This time YOU’RE the one asking the questions - with a simple hashtag on Twitter or LinkedIn - and I promise to give you an answer for a busy person, meaning in about 5 minutes. Plan is to do that 3 times per week, Monday, Wednesday, and Friday, and see where that gets us.

Check out the all-new #AskTrap podcast wherever you’re listening to this, subscribe and rate us in the iTunes store and elsewhere, and help us spread the work if you like what you hear. Beyond that, if you have a questions I can answer about almost anything - brands, marketing, startups, VC, careers, whatever - just use the #AskTrap hashtag, and I’ll get on it.

Thanks again, and I’ll talk to you again soon.
Mar 06 2019
1 min
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Rank #5: HHCIB 034 128 Technology President Sue Graham Johnston

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My conversation with Sue Graham Johnston, the President of G20 portfolio star 128 Technology. Sue actually came to Boston in 2017 to help run 128, a next generation networking company that closes the gap between what your business needs and what your network does. Much of 128's management team also led Acme Packet, a Boston-based unicorn acquired by Oracle in 2013 for a little over $2 billion. Sue was actually the executive at Oracle responsible for the integrating Acme Packet, and for running the resulting business. She was so well regarded by the team that when they were ready for a President in the new business, they called her first.

Between Oracle and here Sue served as the Managing Director of British Oxygen Company, running the UK, Ireland and sub-Saharan Africa region of the Linde Group. While at Oracle she served as Vice President in the Communications Global Business Unit, having joined Oracle through the acquisition of Sun Microsystems, where she held numerous leadership roles in operations, supply chain, and engineering. Sue started her career in management consulting with Bain & Company, and holds a BS in Mechanical Engineering, an MS in Manufacturing Systems Engineering, and an MBA all from Stanford University, the Cornell of the west.

Sue's about as polished and professional as they come, and she's risen to the top of every male engineer-dominated situation she's been dropped into her whole life. I learned over the course of our conversation where that poise and bearing comes from, and all I'll say going is that involves the management and shearing of lesser mammals.
Curious? Well you should be. Check out my conversation with the President of 128 Technologies, Sue Graham Johnston.
May 18 2018
30 mins
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Rank #6: HHCIB 035 Hometap CEO Jeff Glass

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How does a kid from Brooklyn became one of Boston's top startup CEOs? We invested on Hometap because it's a market opportunity on the scale of a whole new capital class, and because my friend Jeffrey Glass is one of the most backable CEO's in Boston.
For this week's episode Jeff and I sat down to talk about why, and how he got to that place from the unlikely starting point of a humble household in pre-hipster, working class Brooklyn.

Jeff is a remarkable guy with a remarkable story, hear him tell it and you'll learn along the way how he thinks about hiring, scaling a business, the important difference between execution and strategy problems, and why Hometap may just end up being the single most important thing he's done so far. Enjoy.
Jul 11 2018
45 mins
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Rank #7: HHCIB 032 Bitcoin Foundation CoFounder Patrick Murck

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You could say Patrick Murck is the man who made Bitcoin respectable.

The cryptocurrency’s journey from preferred medium of exchange for mail-order cocaine to Next Big Thing was a long, strange trip indeed, and my guest this week was right there the whole way. Meet Patrick Murck, Bitcoin insider and Special Counsel at the international law firm Cooley LLP, where his practice focuses on regulatory and legal issues facing the fintech industry. Patrick is probably best known as Executive Director of The Bitcoin Foundation, which he co-founded in 2012.

A prominent, early figure in world of cryptocurrency, Patrick has also held roles in a multiple digital startups and served as an expert for US and European regulators and policymakers. In 2014, he was named among America’s 50 Outstanding General Counsel for 2014.
Today Patrick serves as a fellow at the Berkman Klein Center for Internet & Society at Harvard University, and his research focuses on the law and policy implications of Bitcoin, distributed ledgers, and smart contracts. He also serves as President Board Member for the BitGive Foundation, a philanthropic representative for the Bitcoin and Blockchain Industry, aimed at leveraging this technology to improve public health and the environment worldwide.
Jan 19 2018
42 mins
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Rank #8: HHCIB 030 CarGurus CFO Jason Trevisan

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My guest this week is Jason Trevisan, Chief Financial Officer of Boston-based IPO darling CarGurus. After funding itself for its first 8 years with less than $5 million of total venture capital, CarGurus took its $200 million business to the public markets in October at $16/share, raising $150 million customer acquisition war chest on the back of a $1.7 Billion enterprise valuation. After beating estimates for Q3, the stock sits today around $30/share, representing a market cap of over $3.2 Billion. To call their exit a home run would be a massive understatement, and Jason Trevisan was at the center of it.

This will be Jason’s first big interview since the end of their quiet period, and to set expectations we did NOT talk very much about the business. My focus as always was on Jason’s personal journey, which began at Duke and ran through Bain & Company, a stint at online advertising leader aQuantive until it was acquired by Microsoft, and an extended stay as a VC at Polaris Partners, a Boston VC firm focused on growth equity investments and buyouts in Internet, technology and healthcare.
Dec 09 2017
38 mins
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Rank #9: HHCIB 028 Peach Co - Founder & CEO Janet Kraus

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Peach co-founder & CEO Janet Kraus grew up in a household with two people living as “their best selves,” realizing their potential and doing what they loved. She’s spent the better part of her time since leaving home trying to figure out what that means for her, through a remarkable set of experiences as a student, entrepreneur, and professor at the very top of those professions.
Jun 27 2017
46 mins
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Rank #10: HHCIB 027 Nanigans CEO Ric Calvillo

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Meet Nanigans Co-founder & CEO Ric Calvillo, hear lessons learned from the ups and the downs of the startup journey, and data-driven insight about what most Facebook advertisers are getting wrong.
Jun 20 2017
33 mins
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Rank #11: HHCIB 026 Michelle Dipp & Making A Difference

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My guest the week is healthcare VC superstar Michelle Dipp. Dr. Dipp is a co-founder and Partner of Longwood Fund, having co-founded Longwood portfolio companies Axial Biotherapeutics and OvaScience, both of which she now serves as Chairman of the Board. She previously served as the CEO of Alnara Pharmaceuticals (acquired by Eli Lilly), Verastem (NASDAQ: VSTM) and FlexPharma (NASDAQ: FLKS). BOTH of which

Michelle Dipp is an overachiever in an industry of overachievers. As a young girl growing up in El Paso Texas, though, she dreamed of being a professional ballerina. She worked diligently at it for 8 years — studying under a Balanchine dancer from age 4 — before two attempts at New York auditions ended in heartbreak. Six years of strict Catholic school later, she failed again… this time to get into Harvard, which had become her “dream school” after coming to terms with her mother’s loving but pragmatic advice on ballet and on life. “Sometimes no matter how hard you work,” she said, “you’re just not going to be good enough. And you need to get over it.”

Near as I can tell, Michelle Dipp was never not good enough for anything again. Her Oxford undergrad experience turned into 12 years of study abroad, culminating in a stint as a first class medical researcher. Her work, energy, and leadership skills garnered first the attention and then the high regard of both Big Pharma and Big Private Equity. Driven to the cutting edge of medical science, she used her power and influence to develop promising new platforms into a series of companies that would make any VC salivate. In her spare time she helped build the venture capital firm that would spawn them all — Longwood Fund — whose mission “to identify technologies and found companies that will advance new therapeutics that not only make a difference in the lives of patients worldwide, but also create significant value for investors.”

Michelle Dipp wants it all. She wants what her mom had, which as a nurse in a Texas border town was to make a difference in the lives of real people across a broad spectrum of cultural and socioeconomic circumstances. And she wants what her dad had too, which is to build and lead businesses that make a difference in the community of which they are a part.
That’s what Michelle Dipp wants. And there is simply no doubt she is good enough to get it.

In our second segment this week Michelle and I talked about the differences, similarities, and inevitable convergence of the two great tribes of the Boston innovation ecosystem, Healthcare and Tech. Using the example of her latest project — Axial Biotheraputics — Michelle explains how new treatment “platforms” come about on the healthcare side, and the process by which enterprising entrepreneurs turn promising scientific breakthroughs into therapies that help people in the real world.

Michelle is obviously a rock star, but also a delight to spend time with. I think you’re really going to enjoy getting to know her, in particular the person behind the pedigree.
Jun 06 2017
54 mins
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Rank #12: HHCIB 025 Jeff McCarthy & Picking A VC

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My guest the week is venture capitalist and charter G20 Member Jeff McCarthy. Jeff’s a Partner at North Bridge Venture Partners, focused mainly on materials. He played leadership roles at two early, successful companies within the North Bridge portfolio, Cadia Networks and New Oak Communications, where he was the CEO until that company was acquired by Nortel. Before joining New Oak, Jeff was Vice President of sales and business development at Cadia Networks, a developer of ATM concentrator products for the service provider marketplace, and held senior management positions at Wellfleet Communications, including Vice President of Carrier and Channel Operations. Jeff is a proud and active graduate of the Northeastern University School of Management, and serves as an advisor to the University.

In this week’s second segment Jeff and will focus on a problem that seems like a great one until you have it, which is how to pick the right VC partner when you have more than one to choose from. Jeff will share thoughts on the importance of chemistry and vertical expertise, respond to my question about what’s different for female entrepreneurs, and compare funds specialized in individual stages of the venture journey with those that invest throughout it.

As always, How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.

Here now, my conversation with G20 Member Jeff McCarthy...
May 08 2017
46 mins
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Rank #13: HHCIB 018 Eric Paley & The Idea Myth

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My guest this week is Eric Paley, Managing Partner of Founder Collective, an early stage fund begun by a team of entrepreneurs who themselves launched companies and led them through successful exits. Founder Collective is focused on helping the next generation of great entrepreneurs build important and lasting businesses through it’s refreshingly clear and often-stated mission, to be the most aligned fund for founders at the seed stage. Previously, Eric was the CEO and co-founder of Brontes, which was acquired by 3M in 2006.

Founder Collective’s prescient investments in companies including Pill Pack, Seat Geek, the Trade Desk, Periscope, Buzz Feed, Hotel Tonight, and Uber have made it one of the most prominent seed stage funds in Boston and beyond. Fortune magazine’s influential Term Sheet recently identified Founder Collective as among a group of VC firms outside Silicon Valley who were moving investors beyond their strict belief in "the best and the rest" in venture, matching or beating the performance of the handful of storied West Coast firms to deliver some of the best performing funds of the past decade from firms that didn’t exist before the dot-com bubble.

Our conversation on the importance of “founder friendliness” included Eric’s perspective on the challenges facing portfolio star Uber right now, an exchange I think our regular listeners will find particularly interesting.

In our second segment Eric and I turned to what he calls The Idea Myth, the belief that every great company finds its genesis in some flash of inspiration born in the mind of some genius entrepreneur. The reality, and the core investment thesis of Eric’s firm, is that venture success tends to emerge from teams who deeply understand customer value creation, who have the talent and the will to persist in solving the the seemingly endless string of mundane challenges that must be overcome to will a successful company into existence from nothing. It’s a refreshing reminder of the importance of execution in a business that too often elevatea strategy above all else, and a view I very much share with him and his partners.

How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.
Mar 14 2017
57 mins
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Rank #14: HHCIB 017 Yumin Choi & Clarity On Why

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My guest this week is Yumin Choi, Managing Director of Bain Capital Ventures Healthcare team. Yumin joined Bain's Boston team last year after ten years culminating as a General Partner at HLM Venture Partners. At HLM he led a variety of investments across healthcare IT and services sectors, serving as board director for AbleTo, mPulse Mobile, Oceans Healthcare, Payspan (acquired by Primus Capital), Spinal Kinetics, and Vets First Choice.

Yumin has a really interesting background... born in Seoul, South Korea, lived in Japan as a child and moved to Hawaii at age 10 where he attended the Punahou School, President Obama’s alma mater. He's an investor and mentor in several healthcare accelerators, including Blueprint Health, Healthbox, Startup Health, Rock Health, and 500 Startups. Yumin serves with me on the board of the New England Venture Capital Association, and on the board of overseers for the Boston Symphony Orchestra, and the oversight committee for Boston University’s Coulter Foundation. He also served as a lecturer in the Gordon Institute at Tufts University, where he taught entrepreneurial finance.

I think my conversation with Yumin about the job of being a VC is probably the most illuminating I’ve had to date, focusing on the importance of building a network, looking for patterns in the dots of what can be hundreds of near misses and good ideas below the threshold of Yes, and staying open to opportunities regardless of their source or pedigree. Our second segment, though, is about the single event that probably shaped Yumin’s views on the value of healthcare innovation more than any other... his own diagnosis with cancer at age 31, and a subsequent treatment regime that - all by itself - almost killed him.

This is not the usual blah blah about relationships in venture, folks, try as we always do to avoid that. My conversation with Yumin was about his journey to understand why what he was doing mattered, and I was inspired by him and his story in a way I hope you will be too.

How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.
Mar 07 2017
58 mins
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Rank #15: HHCIB 016 David Cancel & Product Success

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This week's guest is Drift Co-Founder and CEO David Cancel. If you’ve ever landed on a web page and had a real person offer to help you find what you were looking for, there’s a decent chance Drift helped make it happen. Their mission is to “help businesses grow by delivering a better, personal experience across every conversation with their customers," and it’s a space David knows all too well. He’s spent his career building great products for marketers at companies he’s founded including Compete, Lookery, Ghostery, and Performable. He served as Chief Product Officer at HubSpot after it acquired Performable in 2011, and is widely credited as having re-architected both the product and the engineering team at that company prior to its wildly successful IPO in 2014.

David’s active in the Boston tech community investing in and advising organizations like Charles River Ventures, Spark Capital, NextView, DormRoom Fund, EverTrue, Visible Measures, Yottaa, and HelpScout. You can and absolutely should catch his Podcast - Seeking Wisdom - which offers practical advice on health, wealth, life, and learning for fellow entrepreneurs. As you’ll hear in our conversation, David was born and raised in New York City and now lives in the Boston area with his wife and two kids.

In this week’s second segment he and I talked about the process of developing products that win, which is so different from the mythology most startups are framed in after the fact. If you had to develop a person from scratch to drive that process, you’d be hard pressed to design a better fit than David, and we’ll dig into the relationship I’ve always found fascinating, between the person and the products they create.

I’ve known David for a long time, and he’s not only one of the best product guys in Boston, but one of the most broadly read and genuinely thoughtful people in our community. I think you’re really going to enjoy our conversation, which drifts into the working class backgrounds that have shaped us both, the importance of family, and the unvarnished truth about what it takes to create something the world wants badly enough to pay for it.

How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.
Feb 28 2017
58 mins
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