I Trust My AI More Than I Trust Myself with Charley Todd | Manual Work is a Bug Ep 14

This week, it's Matthew's turn for a one-off. ‪@hiremav‬ Founder + CEO Matthew Black ‪@manualworkisabug‬ sits down with guest host Charley Todd, founder of Charley Insurance and friend of the show, for a conversation filmed three months ago that already feels like a time capsule. On the table: the AI model that vanished overnight, why Matthew trusts his model more than he trusts himself, the airplane that explains how he runs Mav, and the old-school answer he gives for surviving a founder's worst days. Chapters 00:00 — Intro: a three-month-old conversation 01:27 — Matt, Matthew, or Matty? 02:44 — Adopting AI as a new independent agency 04:27 — Humans and technology: the next 18 months 05:12 — Everyone is struggling for air 05:56 — Loop engineering 06:43 — The Fable that disappeared 07:37 — It feels like the dot-com boom 08:11 — Operate with AI every day 10:01 — What consumers want: utility and context 11:27 — Insurance inside GPT and Claude 12:02 — The renewal letter nobody wants 13:15 — What Siri should have done 14:53 — I trust my model more than myself 16:20 — Why Mav switched to Rippling 17:13 — Where the human touch still wins 18:28 — Learning vs. building 19:21 — Learn by solving real problems 21:24 — Boeing vs. Airbus: how Matthew runs Mav 22:51 — Give your model context 23:40 — Start with weekend vibe coding 24:20 — Nine problems and one gem 25:20 — The hardest day as a founder 27:29 — Go in with a hundred percent love 30:02 — "Clip it. Publish it." 32:21 — Expanding, not contracting 33:46 — Close Hosts Matthew Black — Founder + CEO, Mav (  / madebyblack  ) Charley Todd — Guest host, independent insurance agency founder (  / charleytodd  , ‪@CharleyInsurance‬ (http://heycharley.com) Links and Resources Anthropic's statement on Claude Fable access, the model that disappeared mid-session (https://www.anthropic.com/news/fable-...) Rippling, the HR and finance platform Mav moved to for its MCP (https://www.rippling.com) Jack Dorsey, "From Hierarchy to Intelligence," on running Block through AI instead of org charts (https://block.xyz/inside/from-hierarc...) Hacker News, where Matthew watches what's coming down the pipe (https://news.ycombinator.com) Obsidian, the note app Charley uses for his master documents (https://obsidian.md) Art of Accomplishment, Joe Hudson's coaching company, home of "How could I enjoy this 10% more?" (https://artofaccomplishment.com) Follow the show Manual Work is a Bug is Mav's podcast, now on video. Watch on YouTube and follow wherever you listen, so you don't wait another six years for the next episode. Mav helps insurance agencies grow their book with AI: hiremav.com. Spotify (https://open.spotify.com/show/5CmXVfE...) Amazon Music (https://music.amazon.com/podcasts/d5a...) #ManualWorkIsABug #AIForBusiness #Founders #InsuranceAgency #AI