SWL Week in Review - half-kelly

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

1/24/2026, 2:10 AM

More or Less — Have Secret or Own Narrative

Jess is in Davos… we are left behind with the riffraff… fun conversation around Clawdbot, Ralph — mercenary AI ‘founders’ … I was personally interested in some of the conversation we got into re: how to support hardware businesses in a world where your 8-sleep or Whoop can’t make money on the software / let alone John Deere.

Hot Takes

Be Retarded to Win at Life — this essay is amazing — the best most original thing I have read in a LONG time. The internet for all its flaws produces really interesting culture — and having spent a bunch of time this week with degen 18 year olds talking about the future of culture, etc. there is a lot of crazy interesting and weird stuff out there — Read this essay && check out Looksmaxxing.

Flat Earth is the Future — speaking of culture — I kinda think that flat earth really is the best possible future for people … the ultimate anti-fragile community people can belong to and find meaning with vs. going down the rabbit hole of personal wifus (btw.. learned this week that actually men are not good AI wifu customers because they churn… it is actually women who stick with AI partners long-term)

Half-Kelly Betting — last year I read this interesting book ‘the missing billionaires’ by the LTCM guys… smart guys (also Jackson people I think) — was reflecting on it re: seed investing and personal allocations and I buy it ... it isn’t about being right (happily I have been plenty of times) it is about bet sizing. For me… it is all half-kelly from here on out… (and the good news is LLMs are pretty good at ballparking it for u — no need for analysts.

Modest Conversations — I was reminded this week of a whole bunch of really interesting podcasts I did 7-8 years ago under the heading ‘modest conversations’ — there are some real gems in there that have aged well (Daniel Gross on AI & big company advantages, Lukas Biewald on Crowdflower & OpenAI 8 years ago!, Joe Lonsdale on UBI, Tod Francis on kids, … really a great catalogue — will do more!)

What happens to hardware businesses with NO subscription support? - 8-sleep, Whoop… heck even John Deere have all built businesses where the hardware is almost free / subsidized and the action is the lock in to subscription software — but with AI bots hammering their way and prying open ever private API known to man… aren’t people gonna just buy the hardware and then build their own software and save the fees? Does hardware get more expensive? Apple forces an upgrade cycle because batteries die & cameras get better… but what is peloton to do?

Incantations & Spells — I had my first good experience with AI actually where I gave it an incantation / some non-obvious thinking… and it unlocked MORE ideas for me vs. just an expression / compression algorithm (99% of things) — it was an interesting experience of what felt like discovering an N-of-1 ‘incantation’ to unlock from huge matrix of human knowledge a new chain of logic… it was cool… and hopeful for me.

Doing Enterprise Sales in 2026— LinkedIn liked this one — comes from a series of long conversations with founders doing enterprise sales at the moment — everyone is soo inundated, I really think the way to do enterprise sales is changing super fast..

The Ancient City & Swerves in How Humans Derive Meaning — Maybe this weekend I can write this essay… but the big thing on my mind. Technology changes the flow of atoms and bits over time with big steps / leaps forward. I actually think with this frame the internet is as big a leap as the wheel (and far bigger than the airplane) — and how humans derive meaning is in a moment of huge shift / perhaps really only 4th ever major human shift… People are circling this in various ways… some proto-thinking last week, lots of convos on cultus and localized communities of meaning, etc. — but there is something deeper going on here around the question of ‘why live?’ (Not to be morbid, my life is great — more broadly)

How excited am I… this excited - a minimum half Kelly it shall be… remember the ¶.

Sam

P.S. MaxBP — instagram made me buy this mini Wiffle Ball pitching machine…. And you know what… I love it — massively overpriced, but god bless capitalism & micro-targeting… so fun for everyone.

P.P.S. — the armored murdered out paramedics truck in the suburbs… I assume military surplus? But really weird to see and dystopic — when the paramedics need armor defense and the cover of darkness on the peninsula? We are in a weird place. What is the deal with this?

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