A few weeks ago I jumped on a call with Alex Miller, co-founder of Chaotic Capital, the early-stage fund he runs with Julie Fredrickson. Their thesis is that the world is too chaotic to predict, so the only thing worth betting on is a founder’s ability to adapt to it.
Alex came to venture from outside the industry. Concert producer, conference producer for Jason Calacanis, eight and a half years at StackOverflow building the private Q&A business, and now also runs a Bitcoin-focused developer tools company on the side of Chaotic Capital.
Some highlights from the conversation:
They invest before there’s even a company. Chaotic Capital’s best deals have come from meeting a founder while they’re still working on something else, sometimes months before the real idea appears. What they’re underwriting isn’t the pitch. It’s how fast someone updates their beliefs once the world proves them wrong.
Almost all of their sourcing happens in Twitter DMs. Julie finds founders by being visible online, and Alex says that if someone can’t communicate clearly and asynchronously in that format, they won’t manage as a founder either.
“Be smarter, cheat, or be first” — Alex rules out cheating, isn’t confident that being smart is a reliable advantage, so being first is the only remaining edge. That makes early conviction a necessity, not just a virtue, and explains why he’s unmoved by people calling him for access once a company is consensus.
Monitoring is largely dead, so capital formation is now the job. With thirty-plus names on a hot company’s cap table, no single investor is really watching for problems. What an early cheque can still offer is help raising the next round, not oversight.
We also got into the origin story behind Valar Atomics (there’s a fascinating great grandfather x Manhattan Project detail in there), why GP-to-GP relationships matter more than LP relationships early on, and why Alex and Julie live off-grid outside Bozeman, Montana.
Hope you enjoy it.
DG
