Grateful for the journey so far, and it continues.
Now I help people, leaders and companies build with AI they own.
I grew up in Vancouver, then went to England for boarding school, university and law school. I paid my way with salmon canneries, fishing boats and selling encyclopedias door to door. World Book, baby. Then four years of backpacking through Europe, Southeast Asia, Africa and South America taught me to stay curious and read a room.
Fresh out of law school, I followed my instincts to Ibiza and caught the entrepreneurial bug. I booked DJs for Manumission and ran Manumission Trips, a holiday company Virgin Express later bought. Then came Journeys by DJ, our label for mix albums with Coldcut, Gilles Peterson and Norman Jay. Some sold hundreds of thousands of copies. Others did not. That is the game.
In 1998 I moved to New York and started an adtech company, LiquidSite, with three MIT grads. We raised money in the dot-com boom, never found product-market fit, and wound it down. It was my MBA.
At Threadless I helped grow a community of independent artists. We put the artist’s name first on every partnership and built the tools to pay them for every product sold. Threadless was the first artist platform Disney allowed to reimagine its characters, and with Gap we made Make Great Together, every artist credited on the shirt.
In 2016 David Kidder and Anne Berkowitch brought me inside the world’s largest companies to build new ventures from within, at Nike, Mars, Exelon, Citibank, Johnson & Johnson and more. They taught me how. I also co-founded Prota Ventures, a venture studio that backed companies like Figment, Bird Buddy and Glidance, a mobility aid for people who are blind.
In 2017 the Tampa Bay Buccaneers asked me to help them rethink who they are and what game day feels like. I brought in Neil Stevenson, who was managing director of IDEO in Chicago. We listened to fans, players, ownership and the city, and landed on five words for the club: human, local, piratical, heartfelt, inclusive. Then we designed them into the stadium, the posters and the season tickets. In 2020 Tom Brady joined, and in February 2021 the Buccaneers won the Super Bowl.
In 2017 I co-produced a blockchain founder summit in Chicago. Figment’s founders, Lorien Gabel, Matt Harrop and Andrew Cronk, came out of that room. Prota incubated the company, and our investment vehicle wrote the first check.
Three years later Figment was worth more than a billion dollars. The credit is theirs. I am proud we gave it a start.
It’s a journey we started few years back and it was awesome to see our work highlighted at a national scale. No one walks alone and I am proud as hell to walk alongside you all!
Atul Khosla, Chief Revenue Officer, Tampa Bay Buccaneers, the day after the Super Bowl, 2021
I have known Wilson for more than a decade, including as a founding partner at Prota. He listens closely, hears what you have not quite said, and gives you his honest read, even when it is not what you want to hear.
Will Little, Founding Partner, Prota Ventures
Wilson and his team turned our ideas into real-world experiments at incredible speed. The data spoke for itself and one of those ventures led to a successful acquisition. We knew we had the right partner to build with.
Brian Hoff, VP of Innovation, Exelon
Wilson was instrumental in catalyzing Figment. He brought the founders together, facilitated our earliest thinking, and backed us before anyone else. He was first money in.
Lorien Gabel, CEO, Figment
I was an early investor in CFX, and I am proud of what the team has built.
CFX gives companies outside the US real access to US banking, through partner banks rather than around them. Since it launched in early 2025, more than $2.5 billion has moved through it.
The thread through all of it: build things that matter, with people you believe in.
Continental Works is here to empower your team. We train your people to build and run their own AI, so each of them becomes more valuable to the company every year. Everything we build together belongs to the company.
I run it with Gary Sheng. We run our own work on the same kind of AI system we train your people to build.
If you are building something, or if you just want to think out loud with someone who has made a lot of the mistakes already.
In 2020 Ashley and I moved to St. Augustine. Our daughters are growing up fast. So are we.
