SWL Week in Review - Make Poor?

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

11/22/2025, 12:24 AM

WEEKLY

More or Less - Long Google, People Don’t Like AI

This week on MOL the topic was basically how bad a public markets trader I am… for a while now I have been very publicly saying that while Meta is the safest long-term AI bet (all ads upside, no risk surface)… I wished I owned a bunch of google stock. Well… this is the week my lack of publics trading prowess / balls really hurts — cuz GOOG is crushing it. TPUs thru Gemini 3 thru the bazillion applications (Waymo to conditional gmail in-line calendaring) — what a freight train. We also discuss consumer AI adoption, Britchella, and why states regulating AI make no sense.

Hot Takes

Tony Soprano Would Have Never Used Email, And Neither Should You — As someone whose emails have ended up in document dumps before (phew with things I stand behind)… I feel this pretty strongly. Only put things in email you are willing to put on the front page of the WSJ… or say ‘your honor’ to… But if there was one lesson this week, it was …. No seriously — don’t put things in email. Reminds me of the great old NYT article about the trouble the mob was having with lazy new recruits using text messaging…

The Best Icebreaker -- Who is your favorite Trump pardon so far? this came from a fun Wednesday night dinner with entrepreneurs who I make come down to the suburbs lured by free beer … it still works. My favorite is the Trail Runner… Lil Wayne is a close second… but there are a lot to choose from / and I assume more to come. You gotta admit they run a great writers room — must not be in the east wing I guess…. Also Jack got a viral tweet out of the dinner which is always nice — good use of marketing budget dollars > beer > distribution.

Seed Investing is Highly Compensated Unlicensed Psychotherapy - learn the person, their beliefs, their framework for delusion… some delusion frameworks are great for money making — some are not. Instead of getting paid, you give them capital to push them over the edge.

What is Water?, What is AI - from a walk with a well known VC… David Foster Wallace famously pointed out that to a fish ‘what is water’ … and to a kid ‘what is AI’ — when it permeates everything / it is nothing..

Which brings me to Kleenex / OpenAI Analogy — with Gemini catching up / there + the distribution AND profit… it is time again to point out how massively financially under-powered OpenAI is without a profit machine. They are staked like crazy by everyone to be at the big boys table… maybe they succeed in being ‘too big to fail’ so that their infinite backers / everyone has to keep shoveling them money… The big remaining story you hear is ‘but ChatGPT is Kleenx’ — they own the brand narrative and that is worth a lot… but that is predicated on the idea that bot-chat is a product and that it is a long-term meaningful form of AI — more likely, just like water — AI is just everywhere / we are awash in it and it actually ISN’T a product category at all.

Post-Cortina Olympic Athletes? Who Is In? - I love skiing and I LOVE hiring athletes who know how to grind, pain, risk, the whole bundle… a whole bunch are about to retire — and I was talking to the US ski team folks about how to connect those retiring athletes to more than just Goldman Sachs as a career step — if you are interested in hiring raw competitive talent for finance or tech / or participating in programs to help them transition LMK (obviously we will run an ettiequte school for them :) … heathens.

Congrats to Rakurai — now number one Solana staking solution? As a small investor prod. Also go Clay Robbins and Colosseum for helping them get going! … also congrats to one of the best people Rob Cheung & Zo Computers

Not Done with Etiquette …. The book is coming … also Jessica and Brit have Ladies edition in SF in the works (which turns out looks like it is going to be way fancier…) and several global events for 2025. Always double down.

Lessons for AI from Electrification particularly good segment on TITV equating what happened with electrification and AI. BTW, the electrification story rhymes with ‘what is water’ — yes we use it everywhere, but we don’t really think about it AND the electric companies aren’t that valuable (and those are even regulated monopolies!)

The Real Waymo Story is Pro-Suburb and Pro-Parent — life is full of unintended consequences… I think what Waymo is really going to impact in the market is what jobs parents can have, and maybe the birth rate… + the value of suburban real estate.

Prop 50: I Knew It Was a Trick — I very very reluctantly voted for this … convinced by people I trust that it was ‘just if Texas did it’ … because from a first principles perspective it seemed very very wrong. And here we are, Texas is blocked but Prop 50 is still rolling thru. When it looks like a trick, it probably is a trick. I should be smarter than that.

Make Poor? — and of course I end this week poorer than I have been in a while… I am not stressed about it — but it does feel like a moment financially. Hopefully people are just pulling out their positions early and packing up for holiday season / leaving their AIs to man the shop… and make rich again when people return to work in January… or never?

Sincerely,

Sam

P.S. Congrats to John on a big next life step. I am only slightly hurt that about 12 people have texted me asking what the startup is, and I have had to say I have no idea :) —… cuz I really don’t! … sly.

P.S. really - lettermeme is really getting fun and you can now make your own versions very simply with your own sources (your custom view of the themes of the day) — I need to spend some holiday time on refinement … but I urge you to check it out before I just auto-subscribe you anyway :)

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