SWL Week in Review - Think of the Children!

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

8/28/2026, 9:38 PM

MORE OR LESS — The Kids Are … Online (and the actual solution not political kitchen sinks!) + Over-Under on Cook’s Tenure at Apple (with some Nike analogy snark) — we obviously get into the public conversation about the Meta settlement… which is so nakedly political on every level and nothing more. Kudos to Meta for navigating a minefield … and at least hinting at the ‘let’s have a real society level conversation about this’ … but beyond the sheer politics of it icky all around…. The annoying part? There really is a solution to be had for kids that actually makes sense - focused on transparency to parents vs. more incomprehensible weird rules (fun fact: I proposed and PMed the original activity log at facebook 14+ years ago… trying to give transparency on people’s own accounts — time to finish the job). Also on the show: Tim Cook's legacy coin-flip — in 10 years he's "either gonna look like a f***ing genius or an idiot" (Apple Silicon vs. completely missing the AI era)… and Jessica live-built a headline-scoring app with a single email to her agent mid-recording. Listen to the full episode →

HOT TAKES

Look, just make your own YouTube content for your kids!? the worst kid media is YouTube but they love it… try as you might, it is VERY hard on YouTube to keep your kids on task with quality content… solution? Just make your own kid media. For a while now with lessinboypodcasts I have been generating on the fly podcasts for my kids… Jess said ‘just make YouTube for them’… and it turns out IT WORKS — the invention of the umbrella, history of hot wheels and more… it isn’t perfect but it is DAMN good and will work even better in 6 months — making these are literal single shot prompts with questions to my bot now & cost like $10 a pop! Wild new world.

We invested in 31 Unicorns before they were Unicorns!? — God I love a clickbait list & thx to Time for providing one AND doing our work for us / had no idea we had invested in 31 Unicorns before they were unicorns lol…. Also, as a personal aside, being on the top list… but dead last on that list — is my favorite place to be … classic Jack Sparrow ‘ah, but you have heard of me’ — and the idea that we have 20% the unicorns of Sequoia at 1/10000th the effort is chef kiss in my book!

Kalshi Oakland A’s tickets — I have a lot of respect for the ingenuity of spammers… this is a perfect adaptation of the Nigerian Prince scam for 2026… anyone who is dumb enough to sign up for free Oakland A’s tickets is exactly the little old grandmas you want to spend time on trying to scam I guess…

Seriously tho, just give parents a log of what their kids are looking at if you want to help. for all you regulators out there… this is the obvious solution … the real regulatory win to force across the whole industry — and with AI it is so much more useful / better than it it could have been a few years ago. Empower parents to know what is up and have the conversations that they want to have to guide their kids…! Also waxing poetic on the pod about this in the context of how dumb it is if you think social media is really like alcohol (debatable) to tell just Budweiser they can only serve 2% alcohol but everyone else can do what they want…

Defending 100B Datacenters a while ago I made the point that if you put 100B data centers in one place you were providing a heck of a fatty target to attack.. and defending those spots visible from space would be a challenge… glad the founder of blackwater agrees (ps. If anyone knows him would love to invest on narrative alone!)

He’s looking for inconsistencies in the word of G-d!… has he found any? One of the great quote in character establishment history… and reminder of the ultimate goal. Whether it be about zero or infinity… and your TAM and EBITDA projections.

at what price does nike become a buyout target? — at $60B / literally the same price as cursor… seems cheap… and while we are on the subject: Tim cook became a nike director 5 years before taking over apple … and for 15 years Nike ripped almost exactly the same way Apple has on supply chain optimization only to collapse in last 5… is sept 1st perfect timing to exit or just the beginning?

AI is (ironically) making silicon valley MORE insular — when every story looks reasonable — the emails, the decks, and now the apps themselves are all plausible — and the variance on the next 5 years is near infinite… you go with the people (and credentials) you already know…

Crypto as a hedge is back on the table — holding a lot of crypto as a hedge feels less purely intellectual than it did 12 months ago…

My Slow partners got into another tiff with Garry Tan… so how can it be a bad week with such fun… the number of large VCs who steal slow bits without attribution is honestly quite flattering.

Discomfort vs. Pain, Know The Difference My oldest started cross country and their coach put this so succinctly as one of the things distance running teaches… quite resonant right now as I try to ramp up running for the New York marathon and am feeling great save an incredibly limiting left calf issue — when is it uncomfortable and worth running through… vs. when do I need to let it heal… and where exactly is that line — TBH I think learning this difference really is a key thing to learn in all life / something I will explicitly be thinking about in who I work with in the future. Also reminds me of this epic graduation speech — make your bed …

Best,
Sam

P.S. Again- I am gonna just push my own stuff — no more youtube for the lessin boys — only AI-generated videos answering interesting questions they actually ask, in my voice… way better, more interesting, and it gives them something to talk about with their future therapists “my dad was so crazy he wouldn’t let me watch YouTube other than content he made” … the goal? Pick explicitly the reasons your kids end up in therapy (no surprises)… and with some luck with every generation the issues they are talking about with their therapists re: their childhood are smaller not bigger!

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