The Best Investment of My Career Wasn’t a Company
I’m a bit nostalgic these days. My son graduates high school in a week. Tuesday we had our annual Boston founders dinner – the first one without Eric Paley as full time partner.
All of this is making me think about my own journey. These career and life crossroads that in hindsight were so formative, but I couldn’t possibly know that at the time.
I met my first partner Dan Sommer in college when I pitched him a terrible business idea.
Twenty-five years ago, I walked into Harvard Business School and met two people who would shape everything that followed. Eric and David Frankel.
The randomness of it still gets me. My first exercise was a negotiations class with Dave. He wiped the floor with me 😉 but then was so kind he offered me a ride home. I decided then and there I always wanted to be on his side of the table.
Or when our wives connected Eric and I, and we talked about our entrepreneurial experiences and asked each other: “Would you ever do it again?” We both had the same answer. “Only if the stars aligned.” And sure enough they did.
The conversations are completely different now. Health. Kids. Teaching. Government. Our parents’ health. Pickleball.
Eric left VC to serve as Massachusetts Secretary of Economic Development. Dave and I are still actively investing and running FC – but I teach at Cornell and he is massively philanthropic. Three pretty different answers to “what matters now.”
The partnership kept growing too. Eric had the foresight to bring Amanda Herson in, and more than five years later she has only deepened what we’ve built together.
The thing about 25 years of social capital – it compounds quietly, through all the moments where you showed up, disagreed honestly, and came back. Through the pivots and the losses and the chapters you didn’t plan for. One day you look up and realize it’s the most valuable thing on your balance sheet.
I want to tell my son that investments in people are sometimes the best ones – perhaps more than ever. And yet you can’t plan for it, can’t engineer the serendipity.
