SWL Week in Review - Enemy of My Enemy

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

12/14/2025, 11:19 PM

More or Less - Media Wars, 1010 Billboard Index, and Narrative Flywheel

Fun MOL this week … ideas that really stuck with me from the conversation were around understanding 2025 entrepreneurial journey as planting a flag, building a team, and then positioning yourself to be able to ‘pivot into the narrative’ in a productive way (see boom supersonic recast as an AI power company) — … and of course, the fact that all companies ultimately become what they set out to destroy.

Netflix vs Paramount - is this an Inverse AOL-Time Warner?
Golden Globes nominees and Disney+'s Taylor Swift docuseries
Bundling unbundling YouTube’s skinny bundle and sports
Starlink on planes = fewer redeyes
Zoox vs Waymo
Space GPUs and the data centers in space
The modern entrepreneurship skill: narrative flywheel
Jess’s and The Information's win correcting CNBC's refuted chip story
AI narrative in China vs US
AI backlash: energy prices, water restraints, and kid's mental health
The 101 Billboard Bubble Index
Will the SpaceX, OpenAI, Anduril, or Anthropic IPOs save the economy?
Sorkin’s book predicted the AI bubble?

Hot Takes

Disney OpenAI is all about Google? — this Disney deal has been perplexing (get it) — but I do buy the simplest answer… which is that Disney is really in it so that they can more effectively sue Google (the enemy of my enemy is my friend) — and why team up with OpenAI to try to rob Google, same reason as why you rob banks (it is where the actual money is)

The Narrative - Trust - Capital - Flywheel — Dave and I riff our way to what we think is really going on in the world… the relationships between infinity narratives, the trust certain people have created in their storytelling, and attracting capital… so long as you deliver 20c on the dollar of progress on the narrative to investors, the flywheel continues…

Boom Supersonic & Narrative Pivots — which leads to this one — boom supersonic somewhat hilariously unveiled their datacenter play based on their jet engine work… ultimate pivot into the narrative slipstream — and a great example of how in an era where AI makes pivoting insanely easy (so long regulatory paperwork moats etc) … tell a big story, do something, and then pivot it away from a silly and highly unlikely narrative (supersonic planes) into the topic du-jour.

101 Billboard Bubble Watch — easy peasy. I wish I had a coffee table book of all the 101 billboards over the last decade to watch the evolution… but my bet is that the lower the percent of company my mom can explain (let alone me) the closer we are to bubble town…

AI Dating, Not Dating AI — close readers will remember a few months ago where I was trying to do a little newsletter matchmaking. It doesn’t work for the reason you could have guessed.. insanely deep pool of overqualified women — and like 3 men, all of whom just want someone hot and young (I get it, just a very unbalanced market). Shocker. Anyway— check out june.date if you are looking for love … or even if not and curious to see your psychographic from your ChatGPT history.

The AI Messiah Angst — I really like this framework from religion… jews vs. christians … works for messiah or AI — same story.

The Fancy People Grin-Fuck Tax… everyone knows that reality distortion fields work in both ways. Very powerful / very famous people have the benefit that they can bend beliefs / the world around them BUT they also frequently never get subordinates to really tell them the truth — they end up trapped in their own realities…. BUT there is a much less discussed problem that fancy people get caught in vis-a-vis other fancy people as well… which is the grin-fuck tax. Fancy people tend to talk to other fancy people, who never want to say no to their dumb ideas / there is little point to challenging them, but also know they are dumb… — so they just grin fuck them, say yes or encourage each other, and get no feedback and no information about what makes sense and doesn’t. This is particularly acute when fancy people wade into starting companies, where what actually is going to work really matters. And it wastes a lot of time, effort, and resources. Give honesty (and accept that those who want grin fucking aren’t gonna like you very much!)

I don’t have any real problems — what problems do YOU have? — one of the most honest discussions I had recently with an entrepreneur…. He wanted to solve ‘real problems that matter;… spent time thinking about what real problems he had, and realized he had none — so went on a quest to find REAL people and find out what their REAL problems actually were so he could solve them. Funny the brutal but honest acknowledgement ‘I have no real problems’ — but it does be the question… in our weird world of today, are the people with resources to solve problems actually reality-field-distorted out of what those problems are (outside of the big headline societal ones which even the fanciest don’t have leverage over anyway)

Speaking of solving problems… solve them for rich people — on the flip side… one sad but real rule in business… it is just way easier to sell things to rich people — they have the money, the time, and are bothered by more small things and corner cases for which you can sell them solutions. As inequality grows, and dollars pool up — sad reality is that as a capitalist you are serving the gross pool of available dollars looking for a solution… not the gross pool of humans — and this might be the real knock on capitalism if you are looking for one — it isn’t that AI can better allocate resources, etc… it is that capitalism alone can’t solve the really really big problems AND it also follows the dollars not actual needs. The counter-counter-argument — all people have problems, starting with the folks whose problems are easiest to solve and will pay the most bootstraps you for everyone else (when it works)

Saturday Zooms Are Easier Than The Concorde — Working on something exciting that is fun… the rare lessin weekend zooms… made me remember how much harder this was a generation ago from my dad.

McKinsey’s AI Marketing is Scary .. For Them — is this really their best? Because if so this is scary for them…

AI Cheap Therapy is Red Flag — So really therapy is the number one ChatGPT use case? If so we should be very very afraid.

Who Funds Creators… We Do. — speaking of AI this was fun to see… unintentionally we are crushing AEO …

News is a Games Cover Story for the NYT — and if you had any doubts.. just remember that really even people who think of themselves as ‘intellectuals’ really just want to play games… they just need the newsroom as a cover story for their own egos… give people an emotional self justification and cover story whenever you can.

happy hanukkah,
Sam

P.S. Modern Etiquette is selling like hotcakes ... great stocking stuffer, just saying.

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