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How Hard Can It Be?

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

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


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








Subscribe to my new #AskTrap Podcast!

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...


HHCIB 036 Castle Island Ventures Matt Walsh

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...


HHCIB 035 Hometap CEO Jeff Glass

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...


HHCIB 034 128 Technology President Sue Graham Johnston

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...


HHCIB 033 Data Intensity CEO Kirk Arnold

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...


HHCIB 032 Bitcoin Foundation CoFounder Patrick Murck

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...


HHCIB 031 Flipside Crypto Founder Dave Balter

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...


HHCIB 030 CarGurus CFO Jason Trevisan

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...


HHCIB 029 Carbonite CEO Mohamad Ali

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...


HHCIB 028 Peach Co - Founder & CEO Janet Kraus

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.


HHCIB 027 Nanigans CEO Ric Calvillo

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.


HHCIB 026 Michelle Dipp & Making A Difference

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...


HHCIB 025 Jeff McCarthy & Picking A VC

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...


HHCIB 024 Mike Troiano & Belonging

Hello and welcome to a very special episode of "How Hard Can It Be"...Up close and personal with the real people behind the hits and misses in Boston's venture capital ​big time. My name is Bob Hower and I'm the Co-founder of G20 Ventures. You can​ ​​​follow me on Twitter at @bobthevc, and​ link to our Medium publication at ​Each week we'll​ ​be ​getting​ to know one of the​ ​luminaries in our local startup community, and drill into a specific area of their​​ ​expertise for the...


HHCIB 023 Stefania Mallett & The ezCater Story

My guest this week is ezCater Co-Founder and CEO Stefania Mallett. Stefania has spent over 25 years building and growing technology-enabled companies that solve real business problems. She co-founded and successfully sold InSite Marketing Technology to what is now KANA on NASDAQ, and prior to that led National Logistics Management (a broker for $225M in transportation services) to profitability for the first time in 4 years. As the COO of IntraNet (now ACI Worldwide,) Stefania revamped the...


HHCIB 022 Patrick Sweeney & The Fear Frontier

My guest this week is Patrick Sweeney, an Olympic athlete turned technology entrepreneur turned full time adventurer. Patrick chases adventure for a living, propelled by a passion to help others do the same through corporate speaking engagements and network television appearances, plus an upcoming book in 2017. Patrick grew up a working class Irish kid outside of Boston, and was shaped by a dramatic life experience he’ll share in our talk. He finished 2nd in the 1996 Olympic trials rowing...


HHCIB 021 SPECIAL: How Are We Doing?

After 20 episodes of the HHCIB Pod, it's time to ask... well... how hard it actually is? How are we doing? What could we do better? We've set up a quick typeform here to gather up your feedback, would love to hear from YOU what we're doing right and how we could do it better. So let us know:


HHCIB 020 Matt Johnston & CMOs On ABM

My guest this week is Matt Johnston, Chief Executive Officer of Mautic, the leader in open source marketing automation. Mautic makes it easy for you to put the right message in front of the right person at the right time, empowering enterprises and agencies with a flexible, open platform built for us by us. Before joining Mautic earlier this year Matt was the Chief Marketing and Strategy Officer at Applause (formerly known as uTest). An integral part of Applause’s growth after joining in...


HHCIB 019 Pierre-Loic Assayag & When To Raise

My guest this week is Pierre-Loic Assayag, the CEO and co-founder of Traackr, the world’s most powerful and effective influencer management platform. Traackr lets marketers scale their influencer marketing programs by focusing on the individual people with the greatest impact on their objectives. Their customers include Coca-Cola, HP, OpenTable, Capital One, Kiehls, Travelocity, SAP and Adidas. Half of the top 50 communications agencies today use Traackr to drive successful social programs...


HHCIB 018 Eric Paley & The Idea Myth

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,...