SWL Week in Review - Wars of Attrition

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

9/5/2025, 10:22 PM

A double header after a week off in Paris being fancy with my wife and celebrating friends… because we all know no one does work in Paris.

More or Less: AI Wars of Attrition
A $170B Anthropic… what does it mean for the public market to be locked out of investing in these crazy companies (and it would be super communist to force companies to go public at a certain valuation)?… the ‘right call’ on chrome… and why lawyers always make all the money right before the fall (as they do now!) … as AI fights AI and we burn it all on computers and power

Hot Takes:

MAHA (make America hot again) not addressed Korean Beauty Products? — it is wild to me to find out that so many Korean beauty treatments and products are banned by the FDA in the USA…. Given Trump’s obvious appreciation for the female form.. how has MAHA not become Make America Hot Again & addressed these insane FDA restrictions getting in the way of American beatification?

MHHA (make harvard hard again) is happening this has been a big talking point for me for the last +2 years… and the Atlantic picked up the story big time in a great essay herewhen you grade inflate everything, kids compete and differentiate on other things - like protests… just make harvard hard again. 1636 did a great writeup last week on this which backchannels tell me was quite meaningful — go team.

HAHHS (Harvard vs. HHS) — team at 1636 did an amazing writeup of the district court rulings in Harvard vs. HHS… highly suggest if you are at all interested you read it / this is cannon of reality of the state of play (ok done now)

AI for Petty Lawsuits — haven’t you always wanted a streamlined way to just sue everyone for minor things throughout your day? AI should be great at this — file a good lawsuit for your slightly cold coffee, e-file it with the right court, serve a person via their Doordash curly fries order — ideal. It just seems like a massive market failure that no one has built this yet (though now that I keep yelling about it at least a few people are trying!).

OpenAI’s ‘LinkedIn Killer’ is tagged ‘Global Policy’, not ‘Product’ — on TITV today talking about OpenAI’s job app announcement (for something coming in 6+ months?) — the blog post announcing isn’t tagged apps, it is tagged ‘global policy’ for a reason — they need a jobs story after spending 2 years talking about eviscerating all the jobs / fear mongering. Also let’s not forget that at big companies when you hire fancy people they all want to do ‘their thing’ and you end up with a thousand of these. Maybe a few are important (sure certify people to use your stuff just like every tech platform before) — but LinkedIn isn’t worried yet about OpenAI (they should be about Merit Firsttho…)

Slow Ventures Etiquette School for YC Graduates— for founders counting down to demo day next week, don’t forget to enroll in your finishing school to learn all the etiquette you need to survive in polite VC society and land a good husband from a good family… I mean VC, firm. Ballroom Dance, Flower arranging, how to shake hands, tie a bowtie, and poor a non-alcoholic-beer. We only take 7%….

Wars of Attrition — the actual AI war of attrition right now is obviously Ukraine… but let that be th most visceral example of what is really going on with most of the work here — cheat, catch cheaters. Spam, catch spammers… etc. We are spending a whole lot of money on compute and energy to just go to war with itself and ideally balance to zero…

GOOGLE Chrome — Google was really saved by the bell (openAI) on this one… and good on them / they def shouldn’t have been broken up — but how this all played out is hilarious & also quite funny that google added $270B in market cap (more than half an OAI generously) on the news… let the acquisition frenzy begin.

The Spinach King was Tweeting a Century Ago — I am not loving the book… but it isn’t bad — about frozen food empire … but it is interesting to see how these guys were basically tweeting in paid ads in newspapers a century ago — messaging and tone would have worked perfectly on X.

What Breaks AI ‘Head’ Investing Narrative? .. it has to be something that is both a bigger dream to the upside AND as capital consumptive… simply excellent businesses need not apply if they are too capital efficient (that is until someone cares about jobs reports again…. Which could be … never?)

Doing Excel for Fun in 2040 — just like it turns out we hammer railroad ties today ‘for fun’ … what would actual railroad workers think of this!… I only wish there was an AI platform to grade my form and qualify me for railroad jobs.

Labubu Osaka— two weeks ago I had never heard of Labubu… now it is everywhere… and apparently the idea that Naomi Osaka shouldn’t be paid the rumored $100M she is getting (according to questionable sources) to promote the things drives threads crazy — which is great because for me that platform despite its success has always been crickets… but I finally think I am getting a handle on how to bait the people that hang out there successfully. ChatGPT had some more ideas...

We are the 120th Best VC (not 170th) — last time I was here to tell you how prod I was to be Time Magazine’s 170th best VC … but the world moves fast.. apparently we are now number 120. Put that in your pipe and smoke it (and never let a ridiculous marketing moment go to waste!

Gay Paris. — was so fun. Congrats to Robert and Charles on a truly special celebration of love and fun.

Seeking Arrangements:

Religion Startups — Duolingo to learn religions, paths to route people to communities for the obvious coming religious revival as people go bankrupt on communities and purpose (and recognizing that gen-z is never gonna show up at a flesh and bones event unannounced / they are way too scared of IRL for that) … lots of great conversations here and looking for more interesting people in the space.

LLM Prediction Markets — a few folks have taken me up on this and are pursing different approaches — but I really want markets for betting on things with real world implications but high scalability — like ‘what will be the top search result to X on Y date’ and ‘what will LLM output for Z’ — love prediction markets, still super early but things like solana are far enough along they can really be built. Send more pls.

Farming — foundation farms is still super focus / more to do there for ‘net jets for farms’ (and if you are interested check out weekly field notes) ... so is slow seed investment Area2 for a different market — but more broadly from testing to members-only-grocery.. change is coming and it tends to be verticalized.

Creators — I keep meeting such awesome niche creators doing great stuff… like randomly Myshootingjourney…. Who really ‘shot her shot’ randomly in Paris. I am not interested in ‘entertainers’ - but send me folks like Jonathan Katz Moses — who have built credibility around passion and are building big businesses in what they love and have trust in.

Lettermeme — you know I am having a blast turning the trusted intelligent news into cartoons — but this is a schtick I am not even close to done with — sign up now… but a lot more soon.

Sam

PS. Kids Wiping Out — it really is just always funny to watch kids eat it (when they are fine)

P.P.S. “You are never up a set” — Jessica Lessin… watching Alcaraz in second set tie-break moments ago — but just a great line / t-shirt.

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