Charles Ferguson

Speaker Spotlight: Charles Ferguson - Filmmaker · Angel Investor · Partner at DVC He sold a company to Microsoft. Then he made a film that won an Oscar. Then he started writing checks into the future of AI. Charles Ferguson doesn't fit neatly into one box — and that's exactly what makes him one of the most fascinating minds coming down the Rabbit Hole this June. Born in San Francisco, Ferguson built his first act in tech: he co-founded Vermeer Technologies, creator of FrontPage — one of the earliest visual web development tools — and sold it to Microsoft in 1996 for $133 million. From there, he turned to a different kind of power: the power of narrative. His documentary Inside Job, a forensic examination of the 2008 financial crisis, won the Academy Award for Best Documentary Feature. Before that, No End in Sight earned a Sundance Special Jury Prize. His work has premiered at Cannes, Berlin, and the New York Film Festival, and his Watergate documentary received the Cinema for Peace award for Most Political Film of the Year. But Charles isn't living in the past. Since 2022, he has become one of the most active early-stage AI investors in the space — a limited partner in six venture funds and an angel investor placing first money into AI and tech startups. He brings a rare trifecta to every conversation: the rigor of a PhD in political science from MIT, the pattern recognition of a serial entrepreneur, and the storytelling instinct of an Oscar-winning director. At The AI Rabbit Hole 2026, Charles joins us to ask the questions most people in the room are too busy building to pause for — about power, accountability, and what the AI era will look like when someone finally makes the definitive documentary about it. That film is coming. The question is whether we're ready for what it reveals. 🗓 June 5, 2026 | Treasure Island, San Francisco hashtag#AIRH2026 hashtag#AIRabbitHole hashtag#MadHats