I grew up in Long Island, NY, and got my first taste of entrepreneurship when I was 9 years old. That company was Wagon Express, a startup where my twin brother, Benjamin, and I worked the docks on Fire Island, NY, transporting renter’s stuff for a weekend in summer paradise. More than any venture since, I credit Wagon Express with a basic understanding of first principals: from problem solving (renters overpack and cars are prohibited on the island) to go to market (Benjamin and I yelling Wagon! Wagon For Hire! You need a Wagon, lady?! at the ferry dock) and P&L (our parents gave us our wagons so that’s a 100% margin business, right?).
Despite early entrepreneurial interest, I chased the traditional hallmarks of success through high school: get into a great school, go to McKinsey, and then get a huge mortgage for a house I didn’t need. It wasn’t until I had a quarter-life crisis freshman year where I changed tack, deciding to live by design rather than default and give myself a non-zero chance at building something that matters.
I ultimately left college to co-found a fintech startup in Denver, Colorado, that was a six-year, “overnight” success story, taking me to Y-Combinator, the Thiel Fellowship, and an eventual acquisition by our biggest competitor. I heard about Drive because I pitched them during our Series A. They passed btw.
I don’t think being a founder necessarily makes one a better VC. But in my case, it gives me inspiration to be the venture capitalist I didn’t always have. That, combined with a firm belief that the raw DNA of great founders and category-defining companies crosses state lines, is why I joined Drive.
