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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.

Ranked #1

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HHCIB 024 Mike Troiano & Belonging

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 ... Read more

2 May 2017

1hr 7mins

Ranked #2

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HHCIB 028 Peach Co - Founder & CEO Janet Kraus

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 t... Read more

27 Jun 2017

46mins

Ranked #3

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HHCIB 029 Carbonite CEO Mohamad Ali

HHCIB 029 Carbonite CEO Mohamad Ali

Meet Carbonite President & CEO Mohamad Ali to hear his remarkable immigrant story, and learn the approach to busines... Read more

8 Aug 2017

34mins

Ranked #4

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HHCIB 022 Patrick Sweeney & The Fear Frontier

HHCIB 022 Patrick Sweeney & The Fear Frontier

My guest this week is Patrick Sweeney, an Olympic athlete turned technology entrepreneur turned full time adventurer. Pa... Read more

18 Apr 2017

50mins

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Ranked #5

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HHCIB 025 Jeff McCarthy & Picking A VC

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 P... Read more

8 May 2017

46mins

Ranked #6

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HHCIB 032 Bitcoin Foundation CoFounder Patrick Murck

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 o... Read more

19 Jan 2018

42mins

Ranked #7

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HHCIB 021 SPECIAL: How Are We Doing?

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 ... Read more

2 Apr 2017

3mins

Ranked #8

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HHCIB 023 Stefania Mallett & The ezCater Story

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... Read more

25 Apr 2017

46mins

Ranked #9

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HHCIB 026 Michelle Dipp & Making A Difference

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, havi... Read more

6 Jun 2017

54mins

Ranked #10

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HHCIB 031 Flipside Crypto Founder Dave Balter

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 cryp... Read more

3 Jan 2018

30mins

Ranked #11

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HHCIB 027 Nanigans CEO Ric Calvillo

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,... Read more

20 Jun 2017

33mins

Ranked #12

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HHCIB 020 Matt Johnston & CMOs On ABM

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. ... Read more

28 Mar 2017

48mins

Ranked #13

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HHCIB 019 Pierre-Loic Assayag & When To Raise

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 in... Read more

21 Mar 2017

43mins

Ranked #14

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HHCIB 018 Eric Paley & The Idea Myth

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 entrepr... Read more

14 Mar 2017

57mins

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