How Hard Can It Be?-logo

How Hard Can It Be?

Business & Economics Podcasts >

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.
More Information


Boston, MA


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








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...


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...


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 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 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...


HHCIB 017 Yumin Choi & Clarity On Why

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 Choice. Yumin has a really interesting background... born in...


HHCIB 016 David Cancel & Product Success

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 products for marketers at companies he’s founded including...


HHCIB 015 Kevin Bitterman & Biotech Innovation

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 Pharmaceuticals off the ground while a graduate student at Harvard Medical School. What was that role? Well, it depends who you ask. When Kevin was asked by the Boston Business Journal he said, "I deserve next to no credit for the tremendous accomplishments they've had there." His team had a...


HHCIB 014 Brent Grinna & The People Stuff

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-profit fundraising organizations track and engage alumni and donors. EverTrue participated in TechStars and was selected as a winner of MassChallenge in 2011. Bain Capital Ventures is their lead investor today, and their partner institutions include household names like Amherst, Williams,...


HHCIB 013 Jules Pieri & Amazon Sucks

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, and bought. Jules started her career as an industrial designer for technology companies and was subsequently a senior executive for large brands, such as Keds, Stride Rite, and Playskool. The Grommet is her third startup, following roles as VP at Design Continuum and President of She...


HHCIB 012 Steve Kokinos & Messaging Diaspora

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 global, cloud-based service and all-in-one app people actually want to use. Under Steve’s leadership, Fuze has become one of the hottest and most highly regarded startups in Boston, creating the Unified Communications as a Service market and transforming the way enterprises view communications as...


HHCIB 011 Craig Spitzer Relationships & Selling

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 assisting clients who need new talent and technology to achieve their business objectives. Craig founded his first company — Alliance Consulting Group — in 1994, at the tender age 29. By 1999 ACG was ranked in the top ten of the Inc. 500, an honor it earned again the following year, becoming the only...


Try Premium for 30 days

Live games for all NFL, MLB, NBA, & NHL teams
Commercial-Free Music
No Display Ads