Podcasts by 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.
Further podcasts by Mike Troiano
Podcast on the topic Wirtschaft
All episodes
Subscribe to my new #AskTrap Podcast! from 2019-03-06T18:28:28
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...
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HHCIB 036 Castle Island Ventures Matt Walsh from 2018-08-14T19:03:23
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...
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HHCIB 035 Hometap CEO Jeff Glass from 2018-07-11T19:29:40
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 Jeffr...
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HHCIB 034 128 Technology President Sue Graham Johnston from 2018-05-18T17:51:32
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 t...
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HHCIB 033 Data Intensity CEO Kirk Arnold from 2018-02-14T22:16:25
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-pers...
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HHCIB 032 Bitcoin Foundation CoFounder Patrick Murck from 2018-01-19T22:28:16
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, str...
HHCIB 031 Flipside Crypto Founder Dave Balter from 2018-01-03T19:42:48
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 inn...
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HHCIB 030 CarGurus CFO Jason Trevisan from 2017-12-09T14:14:24
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, Ca...
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HHCIB 029 Carbonite CEO Mohamad Ali from 2017-08-08T18:49:26
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 co...
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HHCIB 028 Peach Co - Founder & CEO Janet Kraus from 2017-06-27T12:38:15
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...
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HHCIB 027 Nanigans CEO Ric Calvillo from 2017-06-20T13:41:10
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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HHCIB 026 Michelle Dipp & Making A Difference from 2017-06-06T13:15:35
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 OvaScien...
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HHCIB 025 Jeff McCarthy & Picking A VC from 2017-05-08T21:16:52
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...
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HHCIB 024 Mike Troiano & Belonging from 2017-05-02T15:09:55
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 i...
HHCIB 023 Stefania Mallett & The ezCater Story from 2017-04-25T13:19:40
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-found...
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HHCIB 022 Patrick Sweeney & The Fear Frontier from 2017-04-18T18:32:22
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...
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HHCIB 021 SPECIAL: How Are We Doing? from 2017-04-02T18:16:49
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 fee...
HHCIB 020 Matt Johnston & CMOs On ABM from 2017-03-28T17:07:37
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 p...
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HHCIB 019 Pierre-Loic Assayag & When To Raise from 2017-03-21T15:08:21
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 m...
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HHCIB 018 Eric Paley & The Idea Myth from 2017-03-14T15:49:47
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 exit...
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HHCIB 017 Yumin Choi & Clarity On Why from 2017-03-07T15:29:07
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 Ventu...
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HHCIB 016 David Cancel & Product Success from 2017-02-28T15:30:42
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...
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HHCIB 015 Kevin Bitterman & Biotech Innovation from 2017-02-21T15:46:18
My guest this week is Kevin Bitterman, a Partner in Polaris Partners Boston office. Kevin joined Polaris in 2004 to focus on investments in healthcare, after playing a key role in getting Sirtris P...
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HHCIB 014 Brent Grinna & The People Stuff from 2017-02-14T16:06:11
My guest this week is Brent Grinna, the Founder & CEO of EverTrue. EverTrue is a social donor management software platform that helps hundreds of higher education, independent school, and other non...
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HHCIB 013 Jules Pieri & Amazon Sucks from 2017-02-07T15:35:32
This week my guest is Jules Pieri, Co-Founder and CEO of the product launch platform The Grommet. The company’s Citizen Commerce™ movement is reshaping how consumer products get discovered, shared,...
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HHCIB 012 Steve Kokinos & Messaging Diaspora from 2017-01-31T14:52:15
This week my guest is Steve Kokinos, founder and CEO of Fuze, a unified communications platform that improves business productivity by integrating voice, video, and always-on collaboration into a g...
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HHCIB 011 Craig Spitzer Relationships & Selling from 2017-01-17T14:26:59
This week my guest is fellow G20 member Craig Spitzer. Craig’s the CEO of a2c Boston, New York and Philadelphia, an IT consulting and staffing company he co-founded in 2007 with the mission of assi...
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HHCIB 010 Dino Di Palma & Expanding Internationally from 2017-01-10T14:40:34
This week my guest is G20 member Dino Di Palma, who most recently served as the Chief Executive Officer of Benu Networks, a provider enterprise technology that allows network operators to dynamical...
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HHCIB 009 Sarah Downey & AR:VR from 2017-01-03T20:43:55
This week's episode features my conversation with Sarah A. Downey, a Principal at Accomplice focused on venture investing in virtual and augmented reality and frontier tech. Before getting into ven...
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HHCIB 008 Jim Herrnstein & Pivot from 2016-12-26T13:57:56
This week we’re going to do something short and sweet, a Holiday Quickee coming in a little over 30 minutes.
I think you'll really enjoy my conversation with G20 member Jim Herrnstein, one...
HHCIB 007 Jim Crowley & Business Model Innovation from 2016-12-20T15:35:51
This week my guest is my longtime friend and co-conspirator Jim Crowley, who most recently served as CEO of Skyhook Wireless. Before that was the CEO and President of BuyWithMe, and before that of ...
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HHCIB 006 Bill Wiberg & The Death of IT from 2016-12-14T16:15:17
This week my guest is Bill Wiberg, co-founder, General Partner, and spiritual guide of G20 Ventures. Bill is an accomplished executive and 14-year venture investor passionate about technical innova...
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HHCIB 005 Steve Kraus & What Next In Healthcare from 2016-11-30T11:59
This week my guest is Steve Kraus, the general Partner who leads healthcare investing activities as Bessemer Venture Partners a storied century-old VC firm headquartered right here in Cambridge’s K...
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HHCIB 004 Patrick MeLampy & Key To Innovation from 2016-11-21T17:24:01
This week my guest is Patrick MeLampy, co-founder of 128 Technology and that company’s Chief Operating Officer. With longtime partner Andy Ory, Patrick co-founded Acme Packet Inc. and served as its...
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HHCIB 003 Ram Sudireddy & The Role Of Religion from 2016-11-16T13:47:41
This week my guest is Ram Sudireddy, pretty universally regarded as one of Boston's best engineers and entrepreneurs in the world of microprocessors. Starting as a UMass computer and electrical eng...
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HHCIB 002 Jit Saxena & Venture Boards from 2016-11-08T15:12:15
This week's episode features my conversation with the great Jit Saxeena, founder and CEO of Applix and Netezza, Boston startups he led through successful IPO's before being acquired by Cognos and I...
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HHCIB 001 Bob Hower & VC Innovation from 2016-10-06T19:37:35
Our inaugural episode features my conversation with Bob Hower, Founding Partner of Boston-based G20 Ventures. Bob is a 13-year VC vet twice named to the Forbes "Midas List," having led investments ...
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