SWL Week in Review - AI Pokemon (catch'em all) & Hierarchy of Business Models

From:

Sam Lessin <sam@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

6/20/2025, 11:50 PM

More or Less / AI Pokemon 'Gotta Catch 'Em All'

This week we discuss the game of AI Pokemon that all the tech leaders are playing... who is gonna 'catch 'em all' -- we also discuss where / how to make money in the ultimate AI war of attrition & the fact that in capitalism you DON'T WANT TO COMPETE. You need to find places where you are so structurally advantaged and trusted you aren't competing with anyone... and AI collapses a lot of that

Hot Takes:

SaaS is a bad business model… a week or two ago I got a bunch of SaaS investors very very mad on Harry Stebbings podcast by saying SaaS is a bad business model & that - let’s be honest - your SaaS for random X thing really doesn’t matter (doesn’t mean you can’t do it or shouldn’t … but do it for the same reason you make hosiery) — this week I continued to anger people with this talking about a shocking ratio! Oracle is 2x the market cap of Salesforce, but Ellison is 25x richer than Benioff — lot’s of people take issue with this pointing out differences in sales patterns, etc. but the truth of the matter is that people are driven by incentives & the far stronger Oracle business model is why Ellison could keep buying back vs. Benioff selling consistently with a weaker underlying asset (so of course you sell!). And what about Gates? Well … it is easy to forget the history here — the story is he felt like post anti-trust he had to sell implicitly & the case emotionally crushed him (so the story goes) — upshot is the Hierarchy of Business Models

Hierarchy of Business Models — people were less peeved about this framing (because it is hard to argue with TBH) — but the point is this…. The license model/ pay a lot upfront + maintenance is just a better business model than free to start, hope you stay! …

Susan Li Speaks! — susan is beyond amazing person and leader… and you probably haven’t heard her speak because she isn’t very public — but here she is! On a video — you should watch… #team_more_susan

Thank You Israel — as Germany’s chancellor said — they are, once again, doing the “dirty work” for the world.. This week it was amazing to talk to many Israeli entrepreneurs about their businesses / on zoom…. And fully understandable that a few asked to reschedule — In some ways, I really feel like Israel is even more western than most of the west / lives the values.

Narnia / NTINGLEA — I am reading Lion ‘The Horse and His Boy’ — and it is just really funny that the entire thing there is a find and replace of Narnia to NTINGLEA on kindle… hard one to miss… it only comes up in the book a thousand times.

I might have been off on Cursor — so… been doing a bunch more coding and having a lot of fun with it … I am kinda the ideal target here because I have never been a serious engineer, but I have been coding since my dad taught me Q-basic on my Apple 2c as a little kid programming card games… And here is the thing… now that I have gotten better at actually giving cursor the context it needs (and controlling some of its wild mood swings where it decides to delete a bunch of code you most certainly need) — I am liking using it more. I am not sure how defensible any of it is… but I get why people are into it as users.

JET-A — closed the first real poll on rostra.fun which worked really well (props to Jake N. For actually executing it from me whining about why this product doesn’t exist. I also really do think that it is a good demonstration / if just a demonstration — of how you can use some of the concepts behind DAOs / private community currencies to actually drive meaningful action and organization

PI-BB — this bulletin board for matching serious buyers and sellers of private company stock is actually coming along — it is cool to see a few folks start to use it — if you are a QP with a lot of experience buying and selling in the private market and not a BS artist — check it out / coming along

Foundation Farms— this is also trending nicely — meeting more and more people who get that the only way forward if you really care about health and food quality is to just fully opt-out of the industrial food system — and the only way to do that (unless you want to sink a huge amount of time into managing farms yourself) is with a net-jets style collective. We have done a bunch of work building the data room here from live conversations & dialing in pricing ($1M upfront, $10K a month + $2K a month for each additional family member of 3 for all you can consume / want) — getting towards real LOIs and buying some farms.

Fondly, Sam

P.S. — Jessica and I are truly out of TV — got anything for us? This Shane McGillis ‘Tires’ show is watchable … so kinda is this golf show with what’s his name from wedding crashers… but only marginally.

P.P.S — Personal Bots & Vector DBs — this really is fun — I feel like between some internal work I have done for slow + building ‘sam bot’ to screen opinions I am getting a pretty good handle on how to boot pipelines / really setup a pretty repeatable pattern for different communities and information sources quickly and efficiently. I think it is going to be time this summer to build hearsay.email in earnest.

P.P.P.S gotta lick the cookie, and then lick it some more from one of jessica's first employees at The Information re: buying hard assets and adding tech leverage... the talk track is much longer on what really works and doesn't (and boy is it a lot of hard work vs. just software!) but hashtag, just don't forget we were doing early when it wasn't so cool... first-sies

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