SWL Week in Review - AI Flippenings & 2x2s

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

5/2/2026, 7:44 AM

OpenAI gets passed in revenue (and valuation) by Anthropic, Google might now eclipse Nvidia on market cap./ is within a breath… a moment of AI flippenings is upon us & the real story isn’t the vying for first place, it is the fact that there is a race at all… because races mean forever-competition, and forever-competition means non-monopolies… and low margins. This isn’t the ‘winner take all race to be first to AGI’ we were promised (lol)

Other topics on the pod: AI shifting like ads to CPA 'outcome' pricing vs. CPM, OpenAI isn’t the biggest AI company & the law is laggy, Inference is commodity, and the business model is worse than an unregulated utility without borders, The rationalization of AI spending will come and margins will fall, All the money is in storage / databases (which the market noticed apparently), and Storing wealth in narratives, not traditional businesses

HOT TAKES

Lessin Boys’ Podcast — this is getting really fun …now when my kids want podcasts they just tell me the topic and I generate them in a single simple prompt “make me a podcast on Tetris” … or on “Ted Ligety” and BOOM — instant custom entertaining content for the car ride — sharing the ones I generate for my boys here: https://lessinboypodcast.ai/ — and having A LOT of fun with it / actually learning a lot (like the history of EA Sports FC Mobile and Baseball 9… actually fascinating!)

Pricing Out-Of-The-Money Seed Investment ‘Call Options’ — a 2x2 — if you are betting on founder and idea… you can think of 2x2 of great/terrible founder and idea… and maybe you should back great founders with terrible ideas (if you can have conviction the person is great independent of the terrible idea!)

Smart vs. Interesting 2x2 — a very smart (and interesting) friend mentioned to me a person he thought was very smart, but not interesting… makes me wonder / think there is an important 2x2 in there somewhere about people on smart vs. interesting axis — Kanye is interesting not smart? Kim? What do you do with Smart and Boring people, and what can you do with not-smart AND not-interesting!

One more 2x2 — Sub-2 Marathon x2 — can you imagine running a sub-2 marathon / hitting a species level goal, and LOSING a race? Congrats to both Sawe and Kejelcha … and I can’t wait for one of them to do it in crocs

OpenAI Revenue Flippening — we called it (obviously) a few weeks ago and it happened… as I keep saying, the problem is that there is even a competition vs. a run-away winner… long google (and I can’t believe how bad I am at going from insight to public-market-trade)… also I mean, Cramer is long so watch out

Yes the North Koreans are All Over Your Company — I have seen some crazy video first hand captured from interviews where they catch North Koreans mid-stream running like 20 apps on their computer to fake out remote interviews… a forever game of cat-and-mouse… but at least awareness of problems and tools from folks like Tofu (plug) are ramping up

Want a new Job? Prove You Are Good First… — here is the scoop — in age of AI, (1) no one trusts what you say you can do / resumes (2) you can now create pretty good custom tests for each person to just PROVE / back up their claims with tests. This is what MeritFirst is now doing… so if you are applying for a job / want to prove your skills … say what you are good at & then get a certificate that proves it based on custom test just for you. the best people are out there but have no way to signal it because the system only rewards credentials. AI finally fixes that. If you’re hiring or hunting, check it out.

Yes be worried about AI taking all the jobs — but also remember not that many people have jobs anyway — it is kinda crazy to remember that only about 40% of Americans have jobs right now… so the majority of Americans are already out there dealing with meaning in a non-employment world (sort of)… and that 40%… well it is about the same as before when women entered the workforce in the 1970s / so for men, this is just crashed out (never mind the counter read that 92% of families with kids under 18 have at least 1 working parent… and the 66% of those families where both parents are working.. or the counter-counter read about the dual income trap where encouraging both parents to work was a HUGE mistake in national home economics.)

Ishmael — somehow I missed this book in 1992 / growing up… but it is worth a read in 2026 with an AI lens… especially the narratives around (1) humans not as final evolution, but goal to be remembered fondly by higher future intelligence (now retold as AIs not natural beings) (2) Quest for both tree of knowledge AND tree of life (don’t die) (3) inevitable collapse unless you give up population growth, or bust out of planetary limitations (4) need for purpose / narrative. Also funny that Trump is the only contemporary named in the whole book!

Sincerely,
Sam

P.S. Bob the Redneck Historian - peak AI content / use of AI… watch a few.

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