Ep. 4: The Naive Optimist Thesis: Betting on Founders Who Don't Know the Box Exists | Charles Hudson, Precursor Ventures

Charles Hudson has backed 500+ teams over 10 years at Precursor Ventures — one of the original pre-seed firms. In this episode, he explains why his biggest winners come from "naive optimist" founders who break industry rules, why he thinks AI software might have no real moats, and how his contrarian 75/25 reserve strategy is finally getting validated.(0:00) Introduction and Charles Hudson's career path(1:17) Why Charles left Uncork Capital to start Precursor Ventures(4:11) Going solo GP — the decision and the founding story(8:30) Portfolio construction: 75/25 reserves, 40-50 deals per year(12:19) How AI has changed entry price and valuation math(16:11) Entry price flexibility vs. ownership targets(19:00) Founder selection: naive optimists vs. industry insiders(25:55) AI's impact on growth expectations and durability(30:19) The moats debate — "AI software might be toothpaste"(33:44) Finding alpha in CPG, consumer, and non-AI bets(41:08) How Precursor uses AI agents for portfolio support(44:48) First meeting to term sheet — what gets Charles excited(49:38) Lessons from 10 years and 6 funds as a solo GP(53:08) The 1999 internet parallel — spiciest take on AIWhere to find Charles Hudson:LinkedIn: https://www.linkedin.com/in/chudsonFirm: https://precursorvc.com