Drew Austin / Red Beard Ventures

Drew Austin is the Founding Partner of Red Beard Ventures, an early-stage crypto and frontier tech firm. He bought his first Bitcoin in a parking lot in 2013, started his first company at 19 running food delivery out of a Syracuse dorm, and has never had what he'd call a real job. Before starting Red Beard, he built and sold Wade & Wendy, an AI recruiting platform.

Red Beard started as an AngelList syndicate in 2021 and became the springboard for everything else. Over five years, the syndicate has done around 250 investments and deployed $75-100M in SPVs, with 9,000 accredited investors. That led to a $25M Fund I, and then Denarii Labs, a tokenomics accelerator that's run four cohorts and invested in about 30 companies. Drew thinks about the ecosystem he's creating where the fund and Denarii are feeding into each other.

Our conversation gets into a thesis Drew has been carrying for years: the blockchain wasn't built for humans, it was built for AI agents. We were the beta. The next billion users of the internet won't be people, they'll be agents that need wallets, stablecoins, and decentralized infrastructure to act as economic participants in the world. Fund II is his bet on that convergence.

For most of 2025, Drew takes us into his journey of burnout. The crypto world he'd spent twelve years in had split into corporate suits on one end and meme coin degens on the other, and the middle he believed in was dying. He took a real break, went skiing with his kids, and came back and started vibe coding. That's when the AI and blockchain convergence he'd been waiting seven years for finally clicked into place.

Full episode below, or on Spotify / Apple Podcasts