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
My friend @AshFontana just wrote a book: https://t.co/Mjw18K57o5. He shows how to use Artificial Intelligence in your business - whether you're selling stuff online, running a family business or leading a large company - through usable frameworks and practical advice.
The award-winning filmmaker Charles Ferguson is suing the company that owns the History Channel, saying that it suppressed his “Watergate” documentary out of fear that allusions made to the Trump administration would offend viewers. https://t.co/Bs3VaMk3XD
My new startup @theauthsource has just exited stealth mode to launch months early to provide reliable COVID-19 information. Many programs are now available with new interviews being added daily to cover expanding subjects.
Visit https://t.co/tQqG2dw983
“Now democracy is dying through the hands of democracy. How do you fight against that? How do you resist against that?” - @petracostal during the Q+A after @clasberkeley’s screening of @netflix’s THE EDGE OF DEMOCRACY
Join me and @petracostal in Berkeley this Thursday (12/5) for a screening of @netflix's THE EDGE OF DEMOCRACY hosted by @clasberkeley with a Q&A following the screening. Free to the public, no registration or tickets required.
https://t.co/u2Clc5ffg3
#WatergateDoc is now available on demand and DVD. Watch this unprecedented account of one of the biggest political scandals in living memory at https://t.co/TCPsdhxTaW
.@IndieWire calls @CharlesFerguson's @Watergate "fascinating & timely." Don't miss the Canadian Premiere, presented in 2 parts as part of a special double bill. See it this Friday!
Tonight at 6PM PT @clasberkeley & @ucbsoj are hosting a free screening of Part 2 of @Watergate followed by a discussion with me, @harleyhs & Maria Echaveste, deputy chief of staff to @BillClinton. Register via link below
https://t.co/Zjczfpqq3v
Impunity 2.0; Or, PG&E Just Wants to Let California Burn
"@PGE4Me arranged conference calls with Wall Street stock analysts, to reassure them that its liability problems were overblown. And guess who helpfully joined them on these calls..."
https://t.co/HPxxooKeja
As seen in #WatergateDoc, Nixon answers questions from the press, including one from the always wise @DanRather. All episodes are available to stream on @HISTORY.com and app, @iTunes, @PrimeVideo and more.