SWL Week in Review - you know who would LOVE to hear about this...?

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

7/25/2025, 4:56 PM

More or Less :: “You Know Who Would Love to Hear About This? Our Mutual Good Friend ChatGPT”

You know when that one friend starts telling you a long and boring story… and you say ‘you know, bill would LOVE to hear this to get yourself out of listening” — as the AI business model wars ramps up (google rips on the quarter, OAI re-opens their round, etc.) — we talk about how hilarious it would be if characters / AIs start redirecting to each other the queries / conversations they don’t care about (if you aren’t gonna buy something please meet my friend Steve, he wants to hear all about your bunion) — Also, the Boston whaler is the Miata of the sea.

Hot Takes:

Maybe we all just need to re-focus on asking ‘is this actually fun?’ - … you watch Alcaraz play with joy, you read Diller’s description of Rupert just having a blast even when the creditors were after him… and then you take a pitch from founders working on some sinfully boring AI bobble — and you ask yourself, are these guys having fun? Can you possibly win over the long-term if you aren’t having fun? You need sustainable fun, you need fun for the team, etc… but even looking back on what has worked / not in my life, does it all come down to finding people who are fun, who can sustain fun through the suck, and are just joyful? Do you sell when the joy goes away? …the business school case on what ‘makes a good business’ should start with what is gonna be FUN to build — and if your version of true’ fun’ makes you a 1-of-1 all the better because the market is wide open.

Happy Gilmore & Modern Times — ran into the premiere of Happy Gilmore 2 in NYC … went home and let my 3,6,8 year old boys watch select scenes of golf from the original classic… 6 year old doing ‘are you too good for your home’ over and over is priceless. Then looking to educate the young ones I put on more important film — modern times — the problem is that the 8 year old is too smart, and realized how sad it is.

Fetchez la vache — speaking of movies… I also let them watch part of holy grail… whose cultural relevance will never die with all these people running round on quests :)

AI ‘cast of characters’ — broken record time… but I am using ALL the LLMs, not one - and will continue you. Grok is a great republican friend, gemini is a great research assistant (especially when it is sure that Wiz Khalifa is a the Venture Capitalist ) — and OAI, random queries sure.

The mixed up seed markets — They really are mixed up… I don’t know what else to say. There are pockets of Joy, but there is a lot of fomo running around…

The Giga-Looms of the 1700s — People in the 1700s must have been SOOO excited about buying up all the steams you could throw a water wheel on…. With fantasies of power-looms the size of the planet. It doesn’t mean you shouldn’t build some BIG looms, just how you profit from them and depreciate them / the finance of it all is the important part of the vision because it won’t play out like you think it will with faster horses.

Turning 42 is basically turning 40 — fun birthday with some friends in NYC and jess. Superman was ok, F1 was way way better… but the real thing at 42 is that it doesn’t feel much different than 40 / I have nothing to add over the 40 note.

Congrats to Rails.xyz team — if you know, you know… just licking the cookie at having lead the seed for something important in crypto :)

Vibe Code Tricks These instagram tips and tricks for hacky vibe coding are actually sometimes pretty good. scraping all your porfile pictures and backing out a JSON object of age,gender,etc. to dump in my CRM is chef's kiss, even when it is clear the person giving the tip doesn't actually know what they are doing technically.

Best,
Sam

P.S. If you like freaking yourself out — here is one for you — your meat is SOOO f-ed, even when you pay so much for antibiotic free, etc. Might I interest you in netjets for farms :)

P.P.S. Aaron Levie will just never stop talking about enterprise AI will he?… that is his unique version of ‘fun’ :) … good for him…. Same deal with Parker Conrad… the man is a legend because he finds genuine fun in all the weirdest places. Find your n-of-1 fun.

P.P.P.S Yes to Larry Summers on Columbia settlement

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