James Detweiler
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The odds of finding a four-leaf clover are 1 in 10,000, roughly the same as founding a generational company. And yet, people set out to defy these odds every day—clover hunters and entrepreneurs alike. I admire these people.
James Detweiler is a Deal Partner at Felicis. Prior to joining Felicis, James was an investor at Zetta, the first AI-focused venture fund. Before Zetta, James was an investor at SVB Capital, where he served as a Board Observer at Shield AI and LP in Felicis. James graduated summa cum laude from Dartmouth College with a bachelor's degree in Physics and Mathematical Finance. He lives in the Outer Richmond district of San Francisco with his wife, Hannah.
The odds of finding a four-leaf clover are 1 in 10,000, roughly the same as founding a generational company. And yet, people set out to defy these odds every day—clover hunters and entrepreneurs alike. I admire these people.
How has your journey as an AI investor evolved over the years?
At SVB, I invested in 10 startups. Volterra, an edge computing platform, was acquired by F5 for $500M, and Shield AI, an AI-first defense company, was recently valued at $2.8B. I also invested in 9 funds. This gave me a behind-the-scenes look into how the best firms invest, like how Felicis commits 1% on top of each check for founder development.
In 2020, I decided to leave SVB and stake my career on AI. I joined Zetta Venture Partners, the first-ever AI fund. There I studied what makes AI companies different from traditional software companies, from their capital structures to their data assets. I wrote about language models like GPT-3 in 2021 and how the technology could impact industries like customer support and developer tools.
In 2022, I joined Felicis to build out our AI portfolio. In my first month, ChatGPT was released and we led RunwayML’s Series C. Over the last 2 years, I've invested $55M across 7 AI-native businesses: Skild AI, Flower AI, Predibase, Zylon, and three stealth companies. I pitched and helped establish our Felicis Fellows program, where we awarded $200K to four AI researchers across the country. And I’ve built close ties with ML labs and communities in SF.
How has your upbringing impacted who you are today?
I grew up in Santa Clara as the youngest of five. My parents are artists—an actress and a painter—and, through osmosis, made me a decent abstract thinker. I directed this toward physics, where abstract thinking is useful, and eventually investing, where abstract thinking is crucial. As a child, I was lucky to spend a few years in Florence while my parents taught abroad. This sparked a lifelong passion for Italian culture.
What’s similar between physics and investing?
Capital is like potential energy. In a reductive sense, it converts into business traction in the same way potential energy converts into kinetic energy. Some entrepreneurs are so good at this conversion that their companies produce more energy (traction) than they absorb (capital). This doesn’t happen in classical physics, where the law of energy conservation rules everything, but it does in business. Sustaining this conversion, capturing lightning in a bottle, is how generational companies are made. It’s my job to identify when this happens and then offer my unyielding support.
How do you like to connect with founders?
There’s nothing like sharing a founder’s excitement for the future. It’s infectious. Anyone can see failure modes, but seeing the path to success, however narrow, and encouraging founders to traverse that path is my forte. I have an 8’x4’ chalkboard that serves as a canvas for brainstorming with founders, and I also love to share an espresso or hike the Lands End trail to think through unsolved problems.
In my career, I aim to live up to the superlative I won my senior year of high school: “most kind.” I treat founders with empathy and respect, listening carefully and providing transparent feedback. I work hard to earn trust, proactively making intros, conducting research, and sourcing talent. Above all, I authentically share founders’ excitement for the future and feel fortunate to play a part in their journey.
Who is someone you admire?
My uncle Bobby. He has the lowest “fascination threshold” of anyone I know. He’ll stop mid-walk to admire a native plant, follow his nose at the public library, or board a new bus line just to see where it takes him. We often exchange musings on economics and physics, and his adventures in the Galapagos Islands have become lore in my family. The best startups identify a secret or unique insight the rest of the market hasn’t caught on to. Finding these secrets requires staying curious and embracing a low fascination threshold.
What’s something you’re proud of?
I like tackling big challenges. Examples include biking a “century,” hiking the “Dartmouth 50,” running the SF marathon, and learning muay thai. If you have ideas for what my next challenge should be, reach out!
