SWL Week in Review - Betting on LLMs (literally)

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

8/8/2025, 4:26 PM

More or Less :: SaaS Ain’t Back

This week everyone got two email newsletter themes over and over in their inbox (1) congrats Dylan and yay SaaS is back (yes on the D part - but no, it isn’t — what is back is alternative AI optionality to the upside as AI story mainline gets bid up)… and (2) Chat-GPT-5 launched ... the chosen headline of literally every newsletter person on earth late week to juice click rates… (if you didn’t know, as my 6th grade teacher used to say… move a bit closer to the front of the cave - i guess when AI writes the NLs it picks its own for the headline).

Hot Takes

PopeGPT — the world was laughing at the PM of Sweden gut checking things with Chat-GPT — well guess what, that is how this is gonna go down in the future. AI isn’t going to directly control states, but it will be kinda like the pope — all the heads of state consult it, and it launders the context between them as the ultimate negotiator…

Silicon Valley Angsty Vibes? Lessons from My Father In Law — industrialists are generous, Wall Street people aren’t because they know they are one-trade-move away from getting wiped out— in this moment silicon valley is feeling more like Wall Street and less like a factory.

How do you evaluate seed founders in an AI world — help me edit the slow LP letter — we know AI is destroying all the natural signals for seed ... but what do you do about it? We got through this once transitioning from ‘business plans’ to ‘just show me an app’ - but now that you can’t ‘read’ apps and early stats anymore? What?

The Learners Inherit the Earth — In periods of change, the efficiency from experience matters less & speed of adaptation matters more — that is why 20 year olds with no social life & who can do daily 20 hour blocks of focused time are going to win in this era

People Naturally Seek Extremes Online — my basketball player analogy — you used to take pride, purpose, place from being the best in your town / community… without boarders and physical friction the tendency has to be to extremes …

Influencers in Makeup Telling the Story of United Fruit — this is just so amusing to me - you take a book like ‘fish that ate the whale’, slap on some makeup and retell it with a beat… this is what we do now.

The beauty of Mickey is he doesn’t age — the challenges of aging creators, and zooming from yachts as the VC equivalent

AI destroys seed investors ability to analyze product, deck, etc. all that is left is betting on great people — this is the draft of the slow quarterly letter I wrote — send feedback.

OpenAI needs to go public (not stripe) — stripe has no use for massive cash, OpenAI is playing at a table where you need a near infinite chip stack to stay in the game

How should you comp AI researchers? Spin the Wheel — pay them a base salary, give them a once a year spin of the wheel for $1B, … you lose em every once in a while but better comp strategy than $200M a year

Autonomous Vehicle Impact on Real-estate — fun conversation between two old friends Brad Hargraeves (who writes the best re publication thesis driven) and Harry Campbell (who runs the rideshare guy) — quick version is same story rehashed from the impact of Uber a decade ago (here is my article in The Information from 4,000 days ago) — the way you make money on transportation is through the shift in real estate values (see monetization of the railroad) — even funnier artifact … even funnier, here is 12 year old semi-viral quora thread I wrote about autonomous vehicles before people even started talking about levels of automation (hashtag - elon claimed it was around the corner then, I got step one of the timeline timing right… maybe not 2)…. Finally for the real deep cut — I am still waiting for someone to build ‘mystery ride’ (because the hardest part of uber/waymo is you have to know where you want to go!… Just take me somewhere / I am feeling lucky :)!

FIGMA commentary SaaS Ain’t, Back - But People Need a Place to Put AI-Adjacent Bets - that is the story here.

Drunk Test — want to know if a product you are designing is good? Drink 4 beers and try to use it… which makes chatGPT great / even better than my roommate talking to a paper towel dispenser for hours in college

Dog Bereavement — this is a great post from Megan about the creator world / what to back — yes, we would back someone in this space.

What do you do with robots without hands? TVs that follow you around of course — this is so obviously what robots are for — making the screens chase us around the house.

Opportunities : Requests for Projects & Jobs (new section!)

Engineers for Duolingo for Religion — still looking for folks interested in working on this - obvious market need short term around conversion (converting for my wedding / partner, need to learn this religion — just like language) — longer term lack of meaning / search for community on red alert — priority on people who can code/build.

Entrepreneurs for Radio Stations — Pretty interested in this at the moment — they are so cheap! Had some interesting conversations with people about how to throw AI characters as hosts into the mix, etc…. More to come - but this feels straight out of Max Headroom… and if you are interested in it / have an angle to work on LMK

Entrepreneurs for LLM Output Betting Markets — I am really hot to trot on this theme / idea… the problem with prediction markets on real world events is they are too constrained and too slow for good high-frequency trading… But betting on LLM model output (on x date the answer to y query without context will be Z) — is absolute jam. High frequency ready, oracle problem solved - and actually in an interesting ‘markets are information’ sense really quite an interesting angle on model quality and accuracy. HMU on this.

Members for Foundation Farms — I continue to be more bullish on foundation farms (our net jets for farms take to get you opted-out of the awful factory farmed food system that is killing you. Lot’s of people love the idea — and good early momentum, but still looking for more founding members to join (we find basically if you have young kids you don’t want to poison and can afford it — that is the zone)

Childcare / Nanny? — We need to add a new nanny to our family team in Hillsborough - full time is default but open, most hours are afternoons and a few evenings in hillsborough. Ideally flexible to travel - for more context on what this job is see the boys antics at instagram.com/lessin

Sam

P.S. I am starting to experiment with routing questions / sourcing questions from this mailing list (having tagged all the emails up with people data labs + ChatGPT) — got questions you want asked here and/or to people who read this and might know? Post-em here… https://wlessin.com/question

P.P.S. if you have kids… what do you think of launching a merch brand 67, or is it Six Seven, or Six Seeeevven… kids these days.

P.P.P.S I love this ad — as we always say — g*d bless the internet.

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