Gregg Stone on Relentless Optimism in VC and Olympics (A Fireside Chat with Tom Matlack)

Inside the Boardroom: Fireside Chats with Tom Matlack – Gregg Stone Interview

This video is part of a summer interview series hosted by Tom Matlack for his Wesleyan University course, designed for freshman and sophomore college athletes exploring business and life beyond sports. Through real conversations with accomplished leaders, the series offers practical insight into entrepreneurship, leadership, and career discovery.

In this episode, Tom talks with Gregg Stone—entrepreneur, investor, and former Olympic rower—about his journey from law to venture capital, building and backing companies like Great Hill Partners and Iora Health. Gregg also shares the story of how missing the 1980 Olympics led to him coaching his daughter to a silver medal in Rio, and what he’s learned about character, resilience, and finding your path.

What sets this interview apart is Gregg’s openness about failure, reinvention, and the values that shaped his career—from coaching youth hockey to navigating the highs and lows of startup life. His advice is as relevant in the boathouse as it is in the boardroom.

Please subscribe to the series—and share with anyone exploring business, especially college athletes thinking about what’s next.

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Here is the video transcript, edited slightly for clarity.

Tom Matlack:
Awesome. Well, welcome, Gregg. It’s really nice to have you here.

Gregg Stone:
Happy to be here.

Tom:
So I like to start with some softballs and then kind of track back a little bit. One I’d like to start with—and this will be interesting for me anyway—is: who is your favorite athlete?

Gregg:
In terms of uber-athlete across all sports, Wayne Gretzky. He really changed his sport. Hockey now has a lot of thugs and tough guys, but he never took a hit, never made a hit. He had this idea that if you could figure out where the puck was going, that was what mattered—not where it is. He changed the rhythm of the game and made it incredible. He was a thinking man’s athlete. So he’s my favorite athlete overall.

In rowing, it’s got to be Emma Twigg, who overlapped for a while with my daughters. She’s been to five Olympics. In her second and third Olympics, she finished fourth—which is a really hard place to be, just off the podium. But she came back in Tokyo to win a gold medal, and then gamely went to Paris and got a silver. So, wow. She’s very cool.

Tom:
If you look back over your career—broadly defined—what do you suppose you’re most proud of?

Gregg:
Well, I’d say I cross career with life. I found a career path that allowed me to do a lot of fun stuff—like be a good father and coach 17 seasons of youth hockey. It also allowed me to embrace my short attention span—switching careers a couple of times, investing in a lot of little companies, which lets you move around.

I’m proud of the fact that every company I was involved with had a purpose. They gave back to the community, mostly in healthcare. So yeah, I’m proud of that.

Tom:
One thing we focus on with students is self-evaluation—identifying their strengths and weaknesses. What do you suppose yours are, and how have they played out in your career?

Gregg:
I have no idea what I thought my strengths and weaknesses were as a sophomore in college. What I learned over time is that I’m not a great judge of character in the short term. I can figure it out eventually, but I’ve partnered with and invested alongside people who didn’t have the character to be good partners. Sometimes that means losing money, but more importantly, it means not doing the stuff you want to do.

So now, I make up for it by making sure I really know potential partners—or that trusted people I know and trust do. I try to stress-test these relationships before getting in too deep.

I also started out with no quantitative skills. Today, no matter how much you love history or government, you need some quantitative grounding. Statistics, basic math—those are essential in business, law, medicine, everything.

On the strength side, I think I have good interpersonal skills. People generally like me, and that’s been helpful for selling ideas, getting consensus, and frankly, getting opportunities. I’ve gotten invited onto boards, which led to companies going public, just because I connected with people.

Tom:
What’s the most fun you’ve had in your career?

Gregg:
Building companies. That’s why I left the law—you don’t get to be a true participant; you’re just keeping people out of trouble. I loved starting up companies. I was an early employee at a firm called Pell Rudman, which became quite successful. We had six employees and had to figure out how to get to twelve—what services to offer, who to bring in.

Later, I was chairman of a company called PhDx. It was a workout—tough shape when I took over—but it was great to be building something. I wouldn’t go work for a big company when you can have the chance to be in a startup.

Tom:
Yeah, I haven’t had a boss since I was 32. So let’s start all the way back. I want to talk about your dad a bit. I read somewhere that he set a world record?

Gregg:
Yeah. He was a war guy—rowed his freshman year, went to war, came back. In ’46–’47, everyone was back from the war, living in Quonset huts, recovering from malaria and PTSD. He rejoined the Harvard crew, was captain in 1947, and that crew set the 2,000-meter world record on Lake Washington during an intercollegiate regatta. It was 5:47, and it stood for quite a while. Some say the course was short, but it was official—and he lived on that for a long time.

Tom:
What did he do professionally?

Gregg:
He moved to New York—thought Boston was a dead town—and went into shipping. He was very socially capable, ended up on a number of boards. Through early friendships, including some from his Harvard days, he got to know Tom Perkins (of Kleiner Perkins) and Tommy Davis (Mayfield). He was an early investor in both—those were two of the first big Silicon Valley VC funds, and they did extremely well.

Tom:
So your dad was deeply involved with Harvard?

Gregg:
Very. He started writing letters for money, became an alumni representative, and eventually joined the Harvard Corporation. Back then, it was the president and six fellows who ran the business aspects of Harvard. He served for many years.

Tom:
I read 27 years. That’s incredible. So when did you start rowing?

Gregg:
Started in a dinghy at age two. Went to a summer camp with shells—rowed with guys who ended up being Olympians. But I forgot about it for a while. I played lacrosse, football, and hockey in high school until I hurt my knee. Then I started rowing again junior year, through college and beyond.

Tom:
Tell me about the nickname of your collegiate crew—“Rude and Smooth.”

Gregg:
That came from Sports Illustrated, which used to cover rowing. They liked that we had some rowers who were, frankly, rude—like Al Shealy, who would say “So long, suckers” at the 500-meter mark. But we were also really slick—very smooth on the water. So “Rude and Smooth” stuck.

Tom:
You were national champions?

Gregg:
Harvard won in ’74 and ’75 when I was there, and again in ’76 after I graduated. I made it through four years of collegiate rowing without losing a race.

Tom:
You were still rowing in 1980?

Gregg:
Yes. After Harvard, I tried out for the ’76 Olympics in sculling. Didn’t make it. Went to law school and trained in the single. Represented the U.S. in ’77, ’78, and ’79. Would’ve gone to Moscow in 1980, but the Olympics were boycotted.

Tom:
What was your reaction to that?

Gregg:
I actually supported Carter’s decision. The boycott was in response to Russia invading Afghanistan. If we went, we’d be legitimizing their Olympics—just like the U.S. going to Berlin in 1936 gave Hitler a platform. I had no complaints. Rowing had already given me so much—great races, world championships, my future wife. I was already a lawyer and had other things to do.

Tom:
You went to law school and then practiced law for a while. What happened after law school professionally?

Gregg:
After law school, I went to a small firm in Boston—about 30 lawyers—called Healy and Barnes. I didn’t have a clue what I actually wanted to do in law, and they had an old-fashioned rotation program. You could try litigation, family law, corporate law. I found out quickly I didn’t want to be a litigator—way too much paperwork, and I’m not enough of a showman. I ended up helping small companies with securities law and whatnot. That was great.

I was there six years, but I realized it was more fun on the company side than the lawyer side. You’d be sitting in a conference room, ironing out a deal. The principals would agree, shake hands, and go out for a nice dinner. Me—the lowly associate—would go back and write excessive documents all night. I thought, “This is not an effective use of my time. I want to be on the other side of the table.”

Tom:
How did you make that transition—from being a lawyer to being a principal?

Gregg:
First, I went to Dick Tarlow, the top startup lawyer in town. He’d done DEC and all the big names. I said, “I want to do venture capital. Maybe I should join your firm?” He said, “No, no. Join a company. I’ll be your lawyer.”

So I went around to different startups and found one that would take me on—even though I’d never invested before. That was Pell Rudman. The culture there was great. The founders might not have been brilliant, but they knew how to treat people and attract clients and capital. It worked out really well.

Tom:
So what is Kestrel Ventures? Kestrel Management?

Gregg:
When I left Pell Rudman, I eventually started a venture firm called Kestrel Venture Partners with two partners. But remember how I said I’m not always a great judge of character? Both of them flaked out. One did a side deal with a company we were looking at—violated trust. The other kidnapped his kids during a divorce and fled to Egypt, so his wife couldn’t reach them. That did not sit well with our limited partners.

Tom:
Wow. So how did you recover from all that?

Gregg:
I just worked. I didn’t put any more capital to work—I just worked out the companies we had. Luckily, one of the entrepreneurs didn’t need more capital and ended up selling for a great return. After that, I was asked to step into a company called PhDx, a medical information company. I didn’t want to be president and CEO, but I offered to be executive chair—run it without having to handle every issue.

That was a great six years. We went from $20 million in revenue and losing $40 million to $120 million and making $40 million. We should have held on to it longer, but the VCs wanted to sell, so we sold it.

Tom:
Did you maintain Kestrel?

Gregg:
Yes, but just as a name.

Tom:
Then you moved into operating and board roles, right? How did you get involved with Launchpad?

Gregg:
Early days of Launchpad—friend from the VC world knew I was doing angel deals. He said, “Join, not for the capital, but for the network.” So I joined temporarily. At the time, Launchpad was 18 people. Now it’s 100–200 people with staff—largest angel group in the Northeast.

Tom:
I saw you were one of the first investors in Great Hill Partners—Chris Gaffney’s firm. How did that happen?

Gregg:
Chris and the three other founders came out of Media Communications Partners, which came from TA Associates. Nobody at TA got along, so they split into three firms. I was friends socially with one of them. I said, “I hear you named the firm after our family’s place in Marion,” and he said, “Yeah, couldn’t place the name.” I said, “Fine with me—but I want to invest and I want your swag.”

So I was their first commitment. Back then, if you got Yale to invest, everyone else followed. David Swensen at Yale really pioneered institutional investment in private equity and venture. If Swensen was in, everyone wanted in.

Tom:
What’s the best deal you ever did?

Gregg:
Numerically, it was a medical imaging company—portable CT machines. The founder was tough, didn’t listen to advice, but he was smart. I would’ve sold at 5–10x return, but he hung on and got us a 50x return.

More rewarding, though, was Iora Health. The founder was a doctor and entrepreneur. They focused on value-based care—getting paid to keep people well, not per procedure. I believed in him and backed him early. Then called Polaris and said, “Don’t worry—we’re doing this without you.” They panicked and jumped in. The company was eventually sold to Amazon. Unfortunately, they buried the brand—but it was rewarding and did well financially.

Tom:
Let’s talk about your daughter. She learned to row from your wife?

Gregg:
Yep. Started in dinghies. Played lacrosse in high school, didn’t make varsity. My wife coached at the Winsor School, and told me, “You need to convince Jeffy to row. She’s tall—we can win.” She switched in junior year. They won national championships her junior and senior year.

Then she went to Princeton, rowed on a national championship crew there, two U23 gold medals, and tried out for the 2008 Olympic team. Didn’t make it—she was already in med school. Came back and said, “I’m not that good. I’m going to be a doctor.”

I said, “Why don’t we go out in the single a few times a week—just for fun?” She did, and ended up winning all the fall races. Decided to try again.

Tom:
So that was leading up to 2012?

Gregg:
Yes. Harry Parker, my mentor and coach, was already diagnosed with cancer but told her, “Your father knows as much as I do—take him along.” That’s how I ended up coaching her.

She was 10th at Worlds in 2011—had to go through Olympic qualification. Then had the race of her life in London—finished seventh, beat three people she’d never beaten. That made her want to go for a medal.

Tom:
What happened after London?

Gregg:
She went to med school, then came back for 2014 Worlds—finished 10th again. We sat down and said, “If we’re going to do this, we’re going for a medal.” That meant changing everything.

We went to the Patriots—at the time, they had the most sophisticated physiology program. Their nutritionist found she had high arsenic levels, common in New England. Arsenic hinders lactic acid processing—so she was always fatigued.

We cut out the arsenic. She wasn’t eating red meat—he said, “You need 6 oz, five times a week.” She became a beef fan again. Changed her boat, her stroke—everything.

By 2015, she’d gone from 11th to 4th in the world.

Tom:
And 2016—silver medal. Full circle. How did that feel?

Gregg:
London was the reward for missing Moscow. Rio was about the medal. We didn’t do any sightseeing.

She rowed a tactically brilliant race. We knew she could risk it for gold—but she said, “No way. I want a medal. Just get me on the podium.” And she did.

Tom:
So final question for our student athletes. What advice would you give them as they think about their professional futures?

Gregg:
My advice—which used to be unique but is now more accepted—is: don’t worry too much about your first job out of school. It’s not a train to your future—it’s a rock-climbing wall. You look up and choose the next step. You’ll have many careers—maybe in different industries.

Just make sure the first job is interesting, helps you learn, and introduces you to great people.

Tom:
Amen. I’m a perfect example—my first five years postgrad were kind of a wash, and it worked out fine.

Gregg:
Exactly. Be optimistic. I looked around 15 years into my career and realized that the most successful people weren’t necessarily the smartest—they were the most optimistic. Cheerful. Positive. Believing that they could get stuff done.

That’s what I’d say—be upbeat. Brush off the bad, accept the good, and make as many friends as you can. Don’t make enemies.

Tom:
That’s it, man. Thank you so much, Gregg. I really appreciate your time with us and with the students today. That was awesome.

Gregg:
A lot of fun. Good luck, guys!

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Other Fireside Chats on The Good Men Project include:

Kalil Diaz on How to Break Through Limiting Beliefs

Jeff Stevens on Discovering Your Why

Will Thorndike on the Power of Compounding in Investments, Relationships and in Life

Juan de Dios Aguilar on How to Lead, Who to Trust, and Why to Love

Ian MacGregor on Pro Bike Racing, the Secret Drink Mix, Going All In, and Founding Scratch Labs

Tom Macejko on Hunting, Banking, Private Equity, Pulp Fiction and Fulfillment

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You can find the full series on YouTube here:
@FiresideChatsWithTom

Watch for future episodes featuring more leaders from across industries. They all have their own compelling stories and are happy to give advice to the next generation of students, athletes and future business leaders.

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