SWL Week in Review - Orizaba Reflections

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

11/1/2025, 8:38 PM

Orizaba Climb & Reflections

This week Aaron, Dan and I went to Mexico to climb Orizaba — the third highest peak in North America at 18,500. Great food, great adventure, beautiful. 18K+ when you have been at sea level for months is pretty brutal to hot lap but worth it. Apparently Orizaba has become a pretty popular weekend hot-lap from Mexico City … which honestly sounds crazy given that it is legitimately hard peak — Based on the fact that the day we went the only people that summited other than us were 2 Russians who did K2 and 3 other folks we don’t know… seems like a low success rate but fun challenge for the locals. Besides the climb, the adventure, the corn worker strike, etc. the best part of getting a bit out there with smart friends is the conversation — here are some of the highlights of weekly thinking in a low o2 environment...

Hot Takes From Being Relatively Offline & Good Friend Convos...

AI is for remixes & that means AI will consolidate culture not fracture it — remixed AI versions of Eminem are great. So are AI remixes of sitcoms — In the future when you go to a Mexican restaurant you WILL be listening to Taylor Swift — just recut and remixed to fit the ambiance - and you will love it because the familiar + twist sets the tone… and in that way AI will likely consolidate cultures and memes not expand the root cannon. Look out in the near future for all instagram music tracks to be overlay of 5 songs not one.

Aspire to contribute to root culture, accept that you are mostly remixing — if you penned the Odyssey… well done. Most modern culture is just remixes and updates of a narrow core — Real success is root contribution, there is a lot of glory in key remixes… but the goal should be to move the core.

When you think about your life in a narrative ark from a movie — is it too pre-teen? If the morality is too simplistic, or something you want to happen would be too perfect a narrative ark in a TV movie, it is probably wishful thinking based on your mass media upbringing.

Embedding Cultural Priorities from Parents in Kid’s Youtube With AI — I do think YouTube is really pretty awful for kids… but what I would want / seems doable — let me as a parent pick a set of cultural priorities / values for my kids, and then filter videos with LLMs based on those cultural priorities. Heck, even generate with AI new stories, podcasts, videos based on what I am looking to culturally prioritize as values for my kids. I would be more down with that… and it even could work — if content creators are like ‘I am missing a segment of parents who want to show their kids content about perseverance, I should make some of that’ it would be quite powerful.

The Two Core Western Values That Really Matter — When you really strip down what matters to western culture it is (a) You aren’t allowed to murder people (only the state can kill) (b) You should not ever be killed by anyone including the state for saying something (other forms of private retribution can be OK tho). The reason that the reaction to Luigi & any equivocation on Hamas are such a cutting assault on the West is we need to be on the same page about these two core principles — everything else is in the details… but if you start questioning those two values we are in deep trouble.

Status Symbols Matter In Industries Where Success is Non-Transparent — why do people care about status symbols / consumption in LA? Because who is doing well / the hierarchy of the system and success is too non-transparent. Same thing with trader-culture on wall street… but in industries where success is more transparent you don’t need rolexes (which are actually pretty classless in those worlds unless it was your grandfather’s… which is a different sort of snobbery)

The durability of paper was an accident, not intentional. Same with Marble as a roman medium. We all know we have a preservation crisis brewing on information / records …. Digital communication is fleeting and hard to store / archive. Heck, the switch to disappearing messaging is a disaster for history and sense making — but then again, the periods in history we have great records from are mostly accidents.. people didn’t use paper because it would last for 100s of years, or marble for 1000s … they used it as the right medium for the moment with preservation being a nice byproduct.

Harvard Grade Inflation — The year I graduated in 2005, Flat “A” grades made up 24%… now it is 60.2% — wild. Twitter is going crazy over Harvard's new grade inflation report, which basically says the same thing 1636 had previously said in its 3-part series, but the most in-depth look at the report available online is 1636's special edition here — I have been saying for 2 years now that “make Harvard hard again” is a key to securing the future of the university —

The Information’s WTF Conference & ‘No Queens’ Protest — sounds like Jessica’s WTF conference (women in tech and finance) was a big hit… sad the timing meant I couldn’t host the men’s ‘no queens’ protest at the front gates to the conference. Every good conference needs a protest. Next Year… also ‘no kings’ is a great meme — have some really fun twists on this cooking.

Time to start a Modern Safe-Deposit Box Company?… safe deposit boxes are pretty useful… and modern twist with biometrics, better access policies, etc. would be pretty good — they are also basically impossible to get/ manage anyway since banks don’t really prioritize the service… do you just get some downtown spaces, secure them, and make a for-profit modern version? Not too dissimilar to the old ‘armory’ idea — basically off-site gun lockers for people who want guns, but don’t want them at home (with cool possible sharing backbone between locations)

“Exposed rebar is ultimate sign of optimism” — if you build a building and leave rebar sticking out the top… so you have the option to build another story someday - that is real optimism. If you see a community cutting their rebar down … you know all is lost / they have given up.

Bring back Pork — getting rid of pork / our ability for politicians to trade was just a huge mistake. We should have accepted 5% waste for the ability to make deals and get things done. Classic good on paper, but when history is written right along with Jane Fonda’s anti-nuclear push will go down as one of the things that undid us.

The internet destroys local power — it is rational that no one is really invested in / interested in local power anymore. The internet destroys local power three ways (a) gives bigger state /federal units deeper insight easily into local action vs. needing to delegate power — panopticon style (b) because sunshine laws mean you can’t just deal out building permits to your friends with it (c) if an author comes to town to talk, access to that used to matter — but no more, you can just watch on YouTube and email him anyway…. Showing up live doesn’t do much. Side note — the reason building is partially such a mess, is that the ground is the last thing locals can control and in absence of everything else.

Have a pant leave a pant. need a pant take a pant — sometimes you need different pants.

The future of social is ‘norm-core’ old idea — but I am increasingly convinced true / what is going on with Jelly makes more clear. People are burning their eyes out quickly on AI slop, there is a reaction to norm-core media coming.

Why people play modern video games — to socialize, for social status, for faked pseudo status (if you can’t get real social status), … last is for fun. We aren’t in the Tetris era anymore… designing for fun is not the point.

Mirror Mirror On The Realtime AI Wall — one of my favorite digital artworks is the ‘wooden mirror’ from the early 2000s in NYC (google it) — in the age of AI I would be down with more ‘mirrors’ — which took whatever is in front of it / you if you are looking at it — and does the realtime translation into something … this obviously exists with apps, but doing it live and realtime (beefy local hardware?) is a big difference maker in how cool this would be….

Use Drones to Deliver Cash — ATMs of the sky — the theory of drone delivery is great… the places it really makes sense are non-zero (drugs in rural Africa) … but more limited than might be obvious. What about delivering cash via drone? Light, needed immediately, and really fun way to build a new bank without branches!

The real meta-narrative in society is centralization vs decentralization — some communities bias towards centralization (dems, catholics, AI platforms, modern hard-to-replicate science, apple)… some communities bias towards decentralization (republicans, protestants, crypto, enlightenment science, capitalism… jewish culture is an extreme form based around core law / book and questioning. arguing about everything) — we have been in a hyper-decentralization cycle since the enlightenment / printing press, scientific revolution, etc… based on technological realities — and that is unfortunately flipping back with most recent tech cycle- politics follows culture, culture follows tech.

On Storytelling:

Startup investing is swapping whole dollars for cents + story / narrative - you put in a dollar.. you get back a few cents of infra / assets & a story (told by ideally a great story telling talent CEO) — This has always been true — it is ESPECIALLY transparently transparently true in this AI cycle. But ultimately as an investor / early stage VC you basically evaluate stories and story tellers with an eye to which stories ‘WORK’ at a given moment for employees, partners, etc. and how much you are willing to pay for a story —

Profit is just a widely believed story, subset of all possible stories of value — profit / traditional accounting and growth is a very durable and broadly believed story… it is a story you can broadly trust because there is so much liquidity in it — so many people to believe it… but it is in many ways a baseline story / trope — by no means the most valuable one with the highest potential these days. You kinda want a profit sub-plot, but especially as investors have gotten used to never seeing dividends, the profit story is kinda abstract and not the most important. When belief in stories collapses / belief dies then we revert to comfort food story of profit — but it isn’t where the action is vs. cultus as humans seek meaning / are existentially threatened by lack of meaning.

YC / incubators are story template machines — templatized / serialized stories are fine… they work fine especially if you own the whole universe cheaply / for free OR if you are looking to scale capital deployment and just need a portfolio of stories that is easy to consume.. but almost by definition the ‘template’ approach which is easy to consume doesn’t produce spectacular, and if anything limits truly great story tellers.

Also don’t just straight ripoff science fiction and try to pass it off — I LOVE science fiction… when I was at Facebook a decade + ago I ran product manager onboarding and had a science fiction cannon & required reading list and book groups. It is GREAT source material. But nothing angers me more than lazy people ripping off science fiction and trying to pawn it off as their story. Science fiction is a GREAT / perhaps the best starting point for thinking about the future as a technologist, but if people pitch you straight plagiarized science fiction book ideas, run (for many reasons, but at least partially for the same reason you have to be careful about giving founders ideas and having them take them — it proves nothing in what you need to know about how they think and act)

Really good stories tho require innovation in how they are told — the way to tell a startup ‘story’ is always changing — and is at this point radically different than it was a decade ago. To tell a great story, you need to yourself be an incredible story teller & know how to borrow tropes from the past, while still innovating pretty meaningfully on your story and how you tell it. Yes - great artists steal, but they steal and do something fresh vs. just make another Marvel movie.

Opportunities:

Join US — Pilgrimage for AI in the SF Mission on The anniversary of ChatGPT later this month. While in Mexico we saw many pilgrimages along the roads with bikes and music for saints.. look out for slow ventures sponsored pilgrimage to AI from the mission in SF ending at OpenAI’s HQ. More soon, I am betting it would be off brand for the city to shut us down, heck they probably should promote it :)

Best,
Sam

P.S. new forms of hunting & reminder that the US wins in an open market when we make games we can play and get really invested in. We are great at innovating in play / games…. Not so much tho when it isn’t fun.

P.P.S. speakig of fun -- lucha libre is really fun,.... and crazy. I am going to be honest, I think the US's extreme cultural stance against it feels like a misstep. The Mexicans are having a blast with it.

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