How Hard Can It Be?

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 Seoul, South Korea, lived in Japan as a child and moved to Hawaii at age 10 where he attended the Punahou School, President Obama’s alma mater. He's an investor and mentor in several healthcare accelerators, including Blueprint Health, Healthbox, Startup Health, Rock Health, and 500 Startups. Yumin serves with me on the board of the New England Venture Capital Association, and on the board of overseers for the Boston Symphony Orchestra, and the oversight committee for Boston University’s Coulter Foundation. He also served as a lecturer in the Gordon Institute at Tufts University, where he taught entrepreneurial finance.

I think my conversation with Yumin about the job of being a VC is probably the most illuminating I’ve had to date, focusing on the importance of building a network, looking for patterns in the dots of what can be hundreds of near misses and good ideas below the threshold of Yes, and staying open to opportunities regardless of their source or pedigree. Our second segment, though, is about the single event that probably shaped Yumin’s views on the value of healthcare innovation more than any other... his own diagnosis with cancer at age 31, and a subsequent treatment regime that - all by itself - almost killed him.

This is not the usual blah blah about relationships in venture, folks, try as we always do to avoid that. My conversation with Yumin was about his journey to understand why what he was doing mattered, and I was inspired by him and his story in a way I hope you will be too.

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.

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 Compete, Lookery, Ghostery, and Performable. He served as Chief Product Officer at HubSpot after it acquired Performable in 2011, and is widely credited as having re-architected both the product and the engineering team at that company prior to its wildly successful IPO in 2014.

David’s active in the Boston tech community investing in and advising organizations like Charles River Ventures, Spark Capital, NextView, DormRoom Fund, EverTrue, Visible Measures, Yottaa, and HelpScout. You can and absolutely should catch his Podcast - Seeking Wisdom - which offers practical advice on health, wealth, life, and learning for fellow entrepreneurs. As you’ll hear in our conversation, David was born and raised in New York City and now lives in the Boston area with his wife and two kids.

In this week’s second segment he and I talked about the process of developing products that win, which is so different from the mythology most startups are framed in after the fact. If you had to develop a person from scratch to drive that process, you’d be hard pressed to design a better fit than David, and we’ll dig into the relationship I’ve always found fascinating, between the person and the products they create.

I’ve known David for a long time, and he’s not only one of the best product guys in Boston, but one of the most broadly read and genuinely thoughtful people in our community. I think you’re really going to enjoy our conversation, which drifts into the working class backgrounds that have shaped us both, the importance of family, and the unvarnished truth about what it takes to create something the world wants badly enough to pay for it.

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.

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 different view... "All you have to do is read Kevin’s Ph.D. dissertation," said lead investor Terry McGuire, "He was a co-discoverer of (Sirtris' science), and a big reason for their success." Sirtis was acquired by drug giant GlaxoSmithKline PLC in 2008, for $720 million. Trust me when I tell you a VC who downplays their role in a startup’s success is the rarest of creatures indeed, and Kevin’s atypical humility is one of the things that’s made him a go-to guy on the Boston biotech scene.

In his time at Polaris, Kevin also co-founded Genocea Biosciences (NASDAQ: GNCA) and was the founding CEO of Editas Medicine (NASDAQ: EDIT), Morphic Therapeutic and Visterra. He currently represents Polaris as a director of Editas Medicine, InSeal Medical, Genocea Biosciences, Kala Pharmaceuticals, Morphic Therapeutic, Neuronetics, Taris Biomedical and Vets First Choice.

Kevin is also active in the local life science and healthcare start-up community, serving on the Scientific Advisory Board of the Massachusetts Life Sciences Center (MLSC) and with me as Board Chair of the New England Venture Capital Association (NEVCA). He has a BA, summa cum laude, from Rutgers University and a PhD in genetics at Harvard Medical School.

In this week’s second segment Kevin and I talked about how cutting edge biotech companies like the one’s he’s been involved in get off the ground, how they emerge from our great universities to create companies that have collectively saved millions of lives. His answer is nothing like the way most people think of VC, and even different from the technology venture model some of us know so well.

Kevin and I live in the same town in the Western suburbs and have even spent a few Dad’s weekends down in Mohegan Sun (which will NOT be discussed in this podcast.) I know him to be a family man of great kindness, talent, and intelligence, and it was a pleasure spending a little time to get under what makes him tick.

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.

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, Colgate, Brown, Boston University, Phillips Andover, and Phillips Exeter.

The business was born after Brent - who’d been fast tracking as a venture capital and private equity investor - was asked to serve as an Alumni Volunteer for his undergraduate alma mater, Brown University. He found a system in desperate need of upgrade to 21st century technology and tactics, and set out to bring them to the education fundraising process he cared deeply about.

The reason he cared so deeply was that access to higher education had changed the lives of both he and his brothers, who’d grown up on rural farmland in a far flung corner of Iowa. Football and smarts were Brent’s ticket to Brown, where he not only excelled academically but ended up Captain of the Varsity Football Team. After graduating he spent four years in finance at William Blair & Company and Madison Dearborn Partners, then earned his MBA with honors from Harvard Business School.

In this week’s second segment Brent and I talked about the people stuff that almost always ends up being the primary focus of the CEO, at any stage of the business. I think other CEOs and those who aspire to be one will relate to both the insights and the struggles we both shared in this aspect of the job, if not to uncover all the answers then at least to commiserate on some of the harder questions.

I consider Brent both a true friend and one of the most promising entrepreneurs in Boston, I think you’ll enjoy listening in on our conversation... especially if you don’t mind a couple Pats fans / ex-jocks taking apart the parallels of football and business.

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​. Actifio​ virtualizes​​ data ​the way a hypervisor virtualizes compute, ​to ​help customers enable the​ ​hybrid cloud, build higher quality applications faster, and improve business resiliency and availability.​ ​Actifio​... ​Radically Simple.​

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 Ziggs.com. She completed her undergraduate degree at the University of Michigan and people tell her she is the first designer to graduate from Harvard Business School, where she is currently an Entrepreneur in Residence. Jules was named one of Fortune’s Most Powerful Women Entrepreneurs in 2013. In June, 2014, she was invited to the White House Maker Faire to launch The Grommet Wholesale Platform, connecting Makers with Main Street Retailers. She writes a personal blog at jules.thegrommet.com, and the “CEO Unplugged” column on Inc.com. She posts as @julespieri on Twitter and Instagram.

The title of our second segment this week is “Amazon Sucks.” To be honest, no one is more surprised to be writing those words than me, having been an Amazon customer since all they sold were books. To be honest I’ve LOVED Amazon for a long time. I respect their execution and how they take care of me as a customer, and it’s the default store in our household, which spends more than it probably should online.

When I posted something to that effect on Facebook, though, my longtime friend Jules stepped in to set me straight, about the impact of Amazon’s policies related to pricing on fellow entrepreneurs. She has some very specific concerns about the way they’ve gone after counterfeiters in particular, and I have to say having spent some time with Jules that I now share them.

If you’re skeptical, that’s great. Hear her out in our second segment today, and judge for yourself.

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​. Actifio​ virtualizes​​ data ​the way a hypervisor virtualizes compute, ​to ​help customers enable the​ ​hybrid cloud, build higher quality applications faster, and improve business resiliency and availability.​ ​Actifio​... ​Radically Simple.​

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 a key driver of business visibility, process improvement, and results.

Before Fuze Steve was a founder of BladeLogic, a company he took public at $17/share before it was acquired by BMC software for $28, and WebYes, an early market leader in the Web hosting and application service provider business acquired by Breakaway Solutions in advance of their IPO in 1999. Steve is 3 for 3, folks, and we spent the first part of our conversation talking about what he’s learned along the way, from startup through product market fit and scale.

In our second segment Steve and I discussed the proliferation of apps and fragmentation of communications channels that’s ironically making it harder for all of us - at work and at home - to connect with each other.

Think about how many messaging and communications apps you have spread across your laptop, tablet, and smartphone right now, then about the big, dumb piece of plastic that’s probably sitting on your desk at work, and all time, energy and effort we’re all wasting trying and failing to get the right info in the right context to the right person right now. Fuze solves that problem in a rather elegant way, of course, but having spent the last decade or so reflecting on how to help people and companies communicate more effectively, Steve’s got some great insight on the problem, where we are in solving it, where we’ll go from here.

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​. Actifio​ virtualizes​​ data ​the way a hypervisor virtualizes compute, ​to ​help customers enable the​ ​hybrid cloud, build higher quality applications faster, and improve business resiliency and availability.​ ​Actifio​... ​Radically Simple.​

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 consulting firm ever to do so. Ernst & Young recognized Craig as their 2000 NYC Entrepreneur of the Year in Consulting and Outsourcing Services, and by age 36, he was recognized as one of Philadelphia’s top 3 CEOs under 40. ACG was sold to Safeguard Scientific in 2002, after growing to 720 employees and producing annual revenues of over $100 million.

What makes Craig‘s story and life remarkable, though, is its sheer scope. He’s produced or co-produced three feature films; was a founding investor in businesses including two successful nightclubs, and sat as Director and Chairman for Halcyon Jets and on the Board of Trustees at the Kiski School, which he attended as a boy. Our conversation ranged from the streets of Pittsburgh to the beaches of St Barth’s, from the summit of Kilimanjaro to a pre New Year’s Eve party on the Octopus. He counts high school buddies and fraternity brothers among those closest to him, but maintains intimate friendships with people including Dick Vermeil, Michael Strahan, and Billy Bob Thornton. It’s a life touched by the triumph of a hugely successful business and the tragedy of 9/11, in vivid personal terms. It’s not an exaggeration to say our conversation was one of the most fascinating I’ve had so far, and I think you’re really going to enjoy it.

Our second segment features Craig’s unique insight on the role of relationships in selling. As a student of enterprise selling myself I promise you this is a master class in the approaches and personal habits that lead to sales success. Relationships are at the core, of course, but Craig goes way beyond the usual blah-blah-blah to share his thoughts on the importance of being both interested in and interesting to the people you want to get to know better, and his secrets on how to seed, harvest and just enjoy the kinds of relationships that propel a business and a life forward.

I really think you’re going to enjoy this one, don’t forget to tell your friends, subscribe, and rate us on whatever podcast app has my in your head right now.

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​. Actifio​ virtualizes​​ data ​the way a hypervisor virtualizes compute, ​to ​help customers enable the​ ​hybrid cloud, build higher quality applications faster, and improve business resiliency and availability.​ ​Actifio​... ​Radically Simple.​

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 dynamically and exponentially scale existing networks for better service agility and increased stickiness in the home and business. Prior to that he was the Chief Operating Officer at Acme Packet, a company he helped take public and eventually sell to Oracle in a transaction valued well over $2 Billion. Dino also served as Senior Vice President of Worldwide Sales and Business Development at Acme Packet, and as Vice President of Sales and Business Development prior to that.

Before Acme Packet Dino was the Vice President of International Business Development of SEMA/Priority Call, where he spent six years in systems engineering, sales, and business development. He holds a BA degree in Economics and Political Science and an MBA from McGill University and an MA degree in Public Policy and Public Administration from Concordia University.

Dino’s twice been the first guy on the ground to open up a new international territory, and we spent the second part of our conversation talking about what it takes to do so effectively. Our conversation included his single most important piece of advice when it comes to doing that right, thoughts on how to pick the right time and place to begin, and another 20 minutes of hands-on, practical thinking on the right way to take your business from the country it happens to be born in to those that might end up being critical to its growth, shaping both your product vision and the scale of your success.

This is a topic I’m also passionate and have also learned a lot about during my time at Actifio, and I really hope anyone considering doing the same will listen in on what a couple of guys who’ve made all the big mistakes have to say about doing it right.

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​. Actifio​ virtualizes​​ data ​the way a hypervisor virtualizes compute, ​to ​help customers enable the​ ​hybrid cloud, build higher quality applications faster, and improve business resiliency and availability.​ ​Actifio​... ​Radically Simple.​

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 venture she served as Director of Marketing at Ovuline, a women’s reproductive health startup making fertility and pregnancy mobile apps, and as Manager of Content and Communications at Abine, a consumer online privacy startup. She got her J.D. from the University of Connecticut School of Law, and a B.A. in Psychology from Hamilton College.

Sarah’s pretty well known in VR circles as a contributing writer for UploadVR.com, and has been featured as a source in over 250 publications including The Wall Street Journal, the New York Times, Forbes, The Economist, CNET, and CNN. She’s a video gamer, weight lifter, and scifi fan, or as her Twitter bio says, a “17 year-old boy interests in the guise of an adult female.” Awesome.

To me Sarah’s one of the more fascinating characters on the Boston venture scene these days, and what I most hoped to get out of our conversation was a better understanding of how a nice girl from Connecticut goes from being a lawyer to an inked up, cosplaying, video game fanatic helping to make sure Boston holds its spot at the virtual reality grown up table. I found my answer where she did; in the parking lot of a Barnes & Noble a few years back, where she decided to stop living the life other people expected her to live, and started to build a new one around the truth of who she was, what she wanted, and what she loved to do.

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​. Actifio​ virtualizes​​ data ​the way a hypervisor virtualizes compute, ​to ​help customers enable the​ ​hybrid cloud, build higher quality applications faster, and improve business resiliency and availability.​ ​Actifio​... ​Radically Simple.​

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 of the most brilliant yet humble people I’ve encountered in my travels. To say Jim’s not your typical entrepreneur would be a dramatic understatement... First off he has a PhD in astrophysics from Harvard, and in Astrophysics circles he is best known as part of the team that in 1995 used an $86 million radio telescope to find the first black hole hidden at the center of a galaxy.

Rather than rest on his laurels as a tenured professor in some Ivy-covered sanctuary, Jim signed on to apply his remarkable skills in math and physics to one of the world’s most legendary quantitative hedge funds, Renaissance Technologies.

But even that’s not the most interesting thing about Jim Herrnstein. In his spare time, Jim is the Chairman of of an organization called Pivot, whose mission is to create a model system of universal access to quality health care for Madagascar via comprehensive health system strengthening in a region near Ranomafana National Park.

Why the hell Madagascar? Why should anyone who could do a guest cameo on Billions spend his time trying to save lives on an Island 8,600 miles from home? Those are the questions I asked Jim in the second segment of our interview, and a big part of the reason this particular conversation was so special to me, and something I wanted to share during this season of giving.

How Hard Can It Be is sponsored as always 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​. Actifio​ virtualizes​​ data ​the way a hypervisor virtualizes compute, ​to ​help customers enable the​ ​hybrid cloud, build higher quality applications faster, and improve business resiliency and availability.​ ​Actifio​... ​Radically Simple.​