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.
Episodes
August 14, 2018 • 34 mins
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 cryp...
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July 11, 2018 • 45 mins
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 Brookly...
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May 18, 2018 • 30 mins
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 Orac...
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February 14, 2018 • 40 mins
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 provi...
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January 19, 2018 • 42 mins
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...
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January 3, 2018 • 30 mins
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 20...
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August 8, 2017 • 34 mins
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 N...
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June 27, 2017 • 46 mins
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.
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June 20, 2017 • 33 mins
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.
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June 6, 2017 • 54 mins
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 over...
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May 8, 2017 • 46 mins
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 dev...
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May 2, 2017 • 67 mins
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 G20vc.com.
Each week we'll be getting to know one of the luminaries in our local startup community, ...
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April 25, 2017 • 46 mins
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...
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April 18, 2017 • 50 mins
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...
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April 2, 2017 • 3 mins
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: https://miketrap.typeform.com/to/YEeSzu
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March 28, 2017 • 48 mins
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...
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March 21, 2017 • 43 mins
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 age...
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March 14, 2017 • 57 mins
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 s...
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March 7, 2017 • 58 mins
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 C...
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February 28, 2017 • 58 mins
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...
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