My first job was at Lehman Brothers, as an intern in the investment banking training program. I once asked my boss if he ever pulled out leg hairs to stay awake during meetings. Instead of firing me, he told me to leave finance before the money trapped me, then gave me the best career advice I've ever received: "Don't work anywhere your talent isn't the thing that makes the money."

After a few years in .com startups, a brief stint laying tile and hardwood floors, and an even briefer one at Alternative Tentacles Records, I found advertising. My first ad job was with my hero, Cliff Freeman. From there, I went to TAXI, won a few Lions for Amp'd Mobile, and eventually landed at Crispin Porter Bogusky. A few years later, CPB was Agency of the Decade, Burger King was Client of the Decade, and I was one of the most awarded creatives in the world. Some of the work from that time was parodied on SNL, debated on CNN, praised by Al Gore, and included in Taschen's Game Changers, a book about the campaigns that changed modern advertising. Around the same time, I directed some music videos and co-wrote a short film selected at Sundance.

Eventually, I started my own agency, which I ran for awhile, under a few names, most notably Office of Baby and Interesting Development. We won Agency of the Year, picked up awards, and did work I'm still proud of. We helped launch and build startup brands like StreetEasy, Parachute, Zola, and Rippling; worked with bigger startups like Etsy, Stripe, and KAYAK; and occasionally found ourselves in the orbit of much larger companies like Google and Samsung. We also created an installation with Joseph Fraioli for the Walker Art Center.

Then I moved to Portugal, for no good reason. This lasted cinco years. While there, I started writing on a Universal Pictures documentary about Iron Maiden, which hit theaters globally in May 2026. I also founded Supernatural, the first creative agency built on an AI platform, years before generative AI entered the mainstream. After being named Agency of the Year and earning numerous industry honors, Supernatural, along with my team and clients, joined Tombras in Knoxville, Tennessee, where I now serve as Chief Creative Officer.

Since then, Tombras has been named Ad Age Agency of the Year twice, and I've been lucky enough to help lead a creative department with the same basic belief I've had since Lehman Brothers: your talent should be the thing that makes the money.

Outside of advertising, I am a partner in several VC funds, advise startups, and collect art. All things I thought I'd have to give up when I left that investment banking money behind.