SWL Week in Review

Token Trading

August 21, 2026

MORE OR LESS — Stripe Buys an '$7B Apple Tree' - OpenRouter, OpenAI vs. Anthropic vs. Uber vs. Lyft without Network Effects & the AI Consumer Indifference vs. Hatred — the OG crew was back on More or Less this week and we got into Stripe paying $7.5B for OpenRouter... which is 7x what Instagram sold for, for a router…. sure marketplaces are valuable and you would rather be the high-margin man-in-the-middle (especially when you get to look at all the transactions) vs. actually dealing with the pork bellies… BUT is there anything here that others can’t build on their own / won’t? And in a world where it is free to participate in ALL the markets at the same time, is any one apple-tree to trade under valuable? … or maybe it is just free momentum in a world where marketing matters and who cares because number-go-up. "the backlash is not about the data centers. the backlash is about that AI sucks, and it is inhuman." Nobody's lead is safe right now: "it doesn't matter who's in the lead right now. what matters is that no lead is secure, and projections don't mean anything." Also covered: Anthropic's enterprise/Microsoft strategy vs. OpenAI's consumer play, why nobody can price these companies when quarterly revenue swings this hard, and Josh Kushner + Thrive buying the Lakers doing the Left-or-Right not straight thing. Listen to the full episode →

HOT TAKES

Best,
Sam

P.S. Brain Donors… the 1992 Classic — this is an incredible movie… I loved it as a kid (got it on VHS from some Hollywood exec in a box set sent to my dad)… my mom reminded me … showed it to the kids and I have never heard them laugh this hard. Truly the pinnacle of comedy.

P.P.S. So happy that Johnny is uncanceled and Jack Sparrow may sail again — without a doubt the worst pirate… you have ever heard of.

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