How Hard Can It Be?

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.

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.

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.

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.

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.

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.

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.

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.

Meet Carbonite President & CEO Mohamad Ali to hear his remarkable immigrant story, and learn the approach to business value creation that's not only transformed Carbonite into an exciting Boston company again, but enabled his string of successes from IBM, to Avaya, to HP.

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.

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.