Show Notes
Sterling and Aaron go deep on headless products — software you never log into because Claude does the work. Sterling calls it the breakthrough moment of the year, Aaron admits Thanx hasn't shipped theirs yet because not one customer is asking for it. They break down why every operations manual is migrating into GitHub as markdown, why all roads lead to daemons, and the cliff you can never jump off (putting your duct-taped internal tool on the public internet). Aaron casually announces on-air ...
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Sterling and Aaron map the AI adoption ladder; seven levels for individuals, seven more for the organizations they work in, and why the gap between the two is the thing that should keep you up at night. Sterling wants a handful of SMEs building the tools everyone else runs; Aaron argues every single employee should be building and bets on-air that Sterling will eventually cave. They get into why you can't climb past "capable" inside a chat window, what actually separates Claude Cowork from Cl...
Sterling and Aaron break down the new agent stack and what AI actually does to your org chart. Sterling argues the SMEs (subject matter experts) inherit the earth, while Aaron insists generalists who abstract across problems are equally superhuman now. They unpack the three reasons to spin up a sub-agent (parallelization, context preservation, bias-free devil's advocate), what makes a session "poisoned" and how to escape it, and why every Claude turn should produce a documented artifact and a...
Sterling declares slide decks dead — his last board meeting was the last one he'll ever make. He's building HTML presentations with AI now and says in a couple months everyone else will too. Aaron pushes back with the Lawrence Lessig TED Talk approach: slides should be visual storytelling, not six bullet points read aloud. He's trained Claude on his own doodle style and now generates bespoke sketch-art slides that look like something he'd actually draw. They get into where practitioners actua...
Sterling brings the receipts on AI search. He's been tracking restaurant website traffic and watched AI referrals jump from 0.3% in 2024 to 2.5% in 2025, with a projection north of 10% in 2026 — roughly a 33x increase in two years. He and Aaron break down what it actually means: GEO (Generative Engine Optimization) is the new SEO, Google reviews are the new social proof for AI answers, and most of the "AI SEO" advice floating around LinkedIn is garbage. Sterling confesses he's on startup numb...
Sterling has 15 go-to-market agents running at Chowly right now. Not chatbots. Not "AI assistants." Autonomous agents with specialized context, dedicated tools, and triggers that fire on events — like an SEO agent that sees a demo get booked, pulls the prospect's website, runs a full analysis, and has the results ready before the rep even opens their laptop. He breaks down the architecture: context gives the agent its specialty, tools give it capabilities, and triggers give it autonomy. Witho...