Jesse Cole, founder of Synthesis Ventures, joins Sunny Ray to trace an unusual path from 1980s New York City to Wall Street to women's fashion and finally to venture capital. Cole explains how growing up gritty in Manhattan and a hard lesson from his father at Cornell shaped his belief in teamwork over individual brilliance. He recounts 17 years on Wall Street, two boutique exits including a sale to Wells Fargo, and an unlikely pivot into running the apparel company Hot Hippie with his wife. After exiting fashion, a mentor's advice to evaluate startups through the founder's lens led him to an early Airbnb investment and eventually to launching The Seed Lab and now Synthesis Ventures, backed by a wealthy Turkish family and an original Tether founder. Cole details his hands on, founder first approach to investing and his appetite for unconventional bets like Colossal Biosciences, the de-extinction company behind the dire wolf and woolly mouse projects. The conversation blends personal history with a candid look at building companies, funds, and teams across very different industries.
A Wall Street veteran turned fashion CEO turned VC explains why he chases the wildest, most talked about ideas in venture.
Can you give a high level overview of Synthesis Ventures' thesis?
Synthesis is my second fund after The Seed Lab, which was more consumer focused. We're backed by one of the wealthiest families out of Turkey, an original founder of Tether, and another notable investor. My partners and I look mostly at B2B software companies upgrading antiquated industries and marketplaces with technology. Our core thesis is finding companies that balance societal good with real capital returns, businesses doing good things for the planet and for people.
What part of growing up in New York City in the 1980s shaped how you operate today?
It was the Wild West. We had no real technology, just an answering machine to coordinate with friends. It was gritty, dirty, a little naughty, and it forced you to think fast and on your feet. While other kids had green grass in the suburbs, I had cement and taxi cabs. The relationships I built then were paramount, and many of those friendships have lasted my whole life.
You went to Cornell and studied sociology, not finance. What stuck with you from that time?
My father told me if I was ever the smartest guy in any room at Cornell, I should get out. I was never going to be the smartest person there, and that taught me living life as an island is impossible. Bringing people into your orbit to help you think critically matters more than going it alone. I'm a big believer that four eyes on any project beat two.
What pulled you toward equity research sales at ISI Group instead of an operating role at a startup?
I actually wanted to be a talent agent in Hollywood, but that world was nepotistic and hard to break into from the East Coast. Finance was where most people from my university gravitated, and it was a big deal to have a position on Wall Street. I went back to Columbia for grad school to figure out my next move, and Ed Heyman from ISI Group recruited me, starting a 17 year career.
You sold a boutique investment platform to Merlin right after the financial crisis. What did that teach you about timing?
I started that platform because I was tired of giving 50 percent of my profits to the house. A billionaire named Steven Schoenfeld backed a broker dealer we built together, and we hustled our way to a deal with Merlin, a Sequoia backed business, three years later. Moving from a scrappy startup to a much more institutional platform was a real adjustment in culture, rules, and expectations.
After Wall Street you pivoted to fashion as CEO of Hot Hippie with your wife as the creative lead. Walk me through that decision.
My wife had helped build and sell Theory, then hated a big corporate fashion job in Europe and wanted to create for herself. I told her the world only knew her as an operator, not a creator, so we started the business out of our apartment. It grew fast, and when I stepped in as CEO in 2012 we went from about 15 to 17 million in topline to north of 35 to 40 million by 2017, before selling to private equity.
Why early stage investing instead of going back to a comfortable seat in finance?
After selling Hot Hippie I started angel investing and kept making mistakes underwriting consumer assets hyped on social media. A great investor told me to evaluate startups through the founder's lens, not face value. Applying that to Airbnb, which I initially thought was a crazy idea, I realized how few Americans get cash flow on their biggest asset, their home. That diligence turned into one of my best investments and changed how I see the world as an investor.
The Seed Lab was consumer first, but Synthesis is much broader, spanning software, biotech, and hardware. What forced that widening?
I brought in two partners with very different lenses. David Melman ran a portfolio for a multibillion dollar hedge fund and later a single family office's venture and private equity sleeve. My younger partner came from Princeton and Accenture. Together we're a multigenerational team spanning our early thirties to my age, which lets us see opportunities across generations that none of us would catch alone.
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