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 crypto-asset and blockchain space. He worked as a management consultant at Arthur D. Little before that, and later in the strategic initiatives group at Clear Channel Radio (now iHeartRadio). Matt is a proud graduate of Boston's own BC High - where he was of course called "Walshie" by "Fitzy" and "Sully" - going on to attend Babson and the Fuqua School of Management at Duke. Our conversation began as usual with his personal story, and went on to cover the adventure of being the crypto evangelist at one of the world's most highly regarded financial institutions. You'll get his thoughts on where the best opportunities are in the crypto space right now, and on why Bitcoin still may be a bargain.

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 Brooklyn. Jeff is a remarkable guy with a remarkable story, hear him tell it and you'll learn along the way how he thinks about hiring, scaling a business, the important difference between execution and strategy problems, and why Hometap may just end up being the single most important thing he's done so far. Enjoy.

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 Oracle responsible for the integrating Acme Packet, and for running the resulting business. She was so well regarded by the team that when they were ready for a President in the new business, they called her first. Between Oracle and here Sue served as the Managing Director of British Oxygen Company, running the UK, Ireland and sub-Saharan Africa region of the Linde Group. While at Oracle she served as Vice President in the Communications Global Business Unit, having joined Oracle through the acquisition of Sun Microsystems, where she held numerous leadership roles in operations, supply chain, and engineering. Sue started her career in management consulting with Bain & Company, and holds a BS in Mechanical Engineering, an MS in Manufacturing Systems Engineering, and an MBA all from Stanford University, the Cornell of the west. Sue's about as polished and professional as they come, and she's risen to the top of every male engineer-dominated situation she's been dropped into her whole life. I learned over the course of our conversation where that poise and bearing comes from, and all I'll say going is that involves the management and shearing of lesser mammals. Curious? Well you should be. Check out my conversation with the President of 128 Technologies, Sue Graham Johnston.

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 also become a kind of tech “CEO Whisperer” over the years, and serves on a range of boards from Ingersoll Rand to Cramer Marketing. She’s a huge supporter of the local innovation ecosystem here in Boston, rounding out her time at MIT with service on the Executive Committee and Board of Trustees of MassTLC, as a Board Member at The Commonwealth Institute, and on the Advisory Committee for the Massachusetts Technology Collaborative. Kirk is the embodiment of the servant leader mentality, having started (and succeeded) as the kind sales person genuinely focused on earning her customer’s respect and not just their signature. Our conversation covers that, and a remarkable confluence of philosophies on matters significant and trivial, from what makes for an effective President to why showing up on time and prepared is a habit worth establishing and maintaining throughout your career.

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 Director of The Bitcoin Foundation, which he co-founded in 2012. A prominent, early figure in world of cryptocurrency, Patrick has also held roles in a multiple digital startups and served as an expert for US and European regulators and policymakers. In 2014, he was named among America’s 50 Outstanding General Counsel for 2014. Today Patrick serves as a fellow at the Berkman Klein Center for Internet & Society at Harvard University, and his research focuses on the law and policy implications of Bitcoin, distributed ledgers, and smart contracts. He also serves as President Board Member for the BitGive Foundation, a philanthropic representative for the Bitcoin and Blockchain Industry, aimed at leveraging this technology to improve public health and the environment worldwide.

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 dunnhumby for $60 Million in 2011. Dave was named one of 30 Most Disruptive People in Boston Tech by Boston Magazine in 2016, was a Finalist for E&Y Entrepreneur of the Year, and was recognized as a Future Legend by the Ad Club. He co‐founded the Word of Mouth Marketing Association (WOMMA), and authored two books on the subject including Grapevine and The Word of Mouth Manual: Volume II.  As both an independent angel and Venture Partner in Boston Seed Capital, Dave’s investments have included Draft Kings, Promoboxx, FitnessKeeper. and HelpScout. A longtime TechStars mentor, Dave also co-founded Intelligent.ly — a classroom space that helps star employees become managers — with his wife Sarah Hodges back in in 2011, and sits on the Board of Directors of Boch Center for the Performing Arts.

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 Ventures.​..​​ ​People first.

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.

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.

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 growing up in El Paso Texas, though, she dreamed of being a professional ballerina. She worked diligently at it for 8 years — studying under a Balanchine dancer from age 4 — before two attempts at New York auditions ended in heartbreak. Six years of strict Catholic school later, she failed again… this time to get into Harvard, which had become her “dream school” after coming to terms with her mother’s loving but pragmatic advice on ballet and on life. “Sometimes no matter how hard you work,” she said, “you’re just not going to be good enough. And you need to get over it.” Near as I can tell, Michelle Dipp was never not good enough for anything again. Her Oxford undergrad experience turned into 12 years of study abroad, culminating in a stint as a first class medical researcher. Her work, energy, and leadership skills garnered first the attention and then the high regard of both Big Pharma and Big Private Equity. Driven to the cutting edge of medical science, she used her power and influence to develop promising new platforms into a series of companies that would make any VC salivate. In her spare time she helped build the venture capital firm that would spawn them all — Longwood Fund — whose mission “to identify technologies and found companies that will advance new therapeutics that not only make a difference in the lives of patients worldwide, but also create significant value for investors.” Michelle Dipp wants it all. She wants what her mom had, which as a nurse in a Texas border town was to make a difference in the lives of real people across a broad spectrum of cultural and socioeconomic circumstances. And she wants what her dad had too, which is to build and lead businesses that make a difference in the community of which they are a part. That’s what Michelle Dipp wants. And there is simply no doubt she is good enough to get it. In our second segment this week Michelle and I talked about the differences, similarities, and inevitable convergence of the two great tribes of the Boston innovation ecosystem, Healthcare and Tech. Using the example of her latest project — Axial Biotheraputics — Michelle explains how new treatment “platforms” come about on the healthcare side, and the process by which enterprising entrepreneurs turn promising scientific breakthroughs into therapies that help people in the real world. Michelle is obviously a rock star, but also a delight to spend time with. I think you’re really going to enjoy getting to know her, in particular the person behind the pedigree.

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 development at Cadia Networks, a developer of ATM concentrator products for the service provider marketplace, and held senior management positions at Wellfleet Communications, including Vice President of Carrier and Channel Operations. Jeff is a proud and active graduate of the Northeastern University School of Management, and serves as an advisor to the University. In this week’s second segment Jeff and will focus on a problem that seems like a great one until you have it, which is how to pick the right VC partner when you have more than one to choose from. Jeff will share thoughts on the importance of chemistry and vertical expertise, respond to my question about what’s different for female entrepreneurs, and compare funds specialized in individual stages of the venture journey with those that invest throughout it. As always, 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 Ventures.​..​​ ​People first. How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple. Here now, my conversation with G20 Member Jeff McCarthy...