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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.

Popular episodes

Subscribe to my new #AskTrap Podcast!

Mar 6 • 01:55
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...

HHCIB 036 Castle Island Ventures Matt Walsh

Aug 14 • 34:45
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...

HHCIB 035 Hometap CEO Jeff Glass

Jul 11 • 45:51
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 ...

HHCIB 034 128 Technology President Sue Graham Johnston

May 18 • 30:46
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 li...

HHCIB 033 Data Intensity CEO Kirk Arnold

Feb 14 • 40:33
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 Presid...

HHCIB 032 Bitcoin Foundation CoFounder Patrick Murck

Jan 19 • 42:29
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...

HHCIB 031 Flipside Crypto Founder Dave Balter

Jan 3 • 30:24
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 f...

HHCIB 030 CarGurus CFO Jason Trevisan

Dec 9 • 38:30
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 ...

HHCIB 029 Carbonite CEO Mohamad Ali

Aug 8 • 34:28
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 ...

HHCIB 028 Peach Co - Founder & CEO Janet Kraus

Jun 27 • 46:40
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 profe...

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