Brian and Brandon debate how a newly hired product leader at Anthropic would find growth big enough to match the expectations of an IPO, which Brian expects around the end of 2026. Brandon says he would start in the research group, hunting for breakthroughs that could serve markets like finance and healthcare, and raises contextual ads even though he jokes the idea could get him fired. Flipping Alex Karp’s warning about AI systems learning a company’s differentiation, Brian proposes a product that sits between employees and their data, then shows executives where to cut costs in the 70 to 80 percent of work he estimates doesn’t set them apart. Pointing to Sierra’s outcome-based pricing, Brandon suggests Anthropic take over a system, absorb the risk, and get paid only when it delivers. His AI-assisted car purchase leads to a discussion of opt-in, intent-based commerce, and Brian argues Anthropic still lacks the kind of aggregation point he sees as the biggest way to make money. They close on Brandon’s half-joking plan: wait until the model is smart enough, then ask it how to make money.
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