Sam Lessin's weekly newsletter — 70 issues, searchable archive.
optimistic, disciplined, and terrified all at once
November 6, 2026
MORE OR LESS – With Still California Resident Parker Conrad Parker is a great hang… Jess and I do More or Less with our special … still California resident Parker Conrad (phew). We talk about where the real leverage in AI is / being…
60,000 Strangers, One Private War
November 2, 2026
MORE OR LESS with Bing Gordon — haven’t listened yet, but Brit and Dave had Bing talk about life, Silicon Valley, and his new book… Bing is the best — a truly wise man — so different vib…
Warhound
October 26, 2026
MORE OR LESS — SpaceX / Tesla Merger, DUH — Shocker after Elon strapped Evel Knievel rocket boosters on a Hot Wheels car Epcot special and called it “flying” — Disney really should have allowed $50K reserv…
Nihilism
October 16, 2026
MORE OR LESS - When APIs become two way negotiations — Would you rather be right or rich? The question of the moment watching CoreWeave, all consumer agents being ‘good enough’, and the trajectory of Anthropic revenue. We have been di…
$1T in Escrow, Minimum
October 2, 2026
MORE OR LESS — Meta Muse vs Instinct vs OpenAI Dots: Do AI Agents Have Any Moat? — I switch between muse, instinct, and dots at basically zero cost — one github repo, a few databases, feed the new thing my context, done… if the cost of…
M-M-Maximum Entertainment
September 28, 2026
Stop Pretending the AI labs are a special case in business… they are not. MORE OR LESS — Pro West Point, Short A16Z U — ( the preview got heated )… this is the convo that drew all the ire… but look, when it comes to learning the ski…
M-M-Maximum Entertainment
September 18, 2026
MORE OR LESS — Hit The Brakes They'll Fly Right By — ( max lessin has the preview )… If there is one thing that AI has been great at for years it is optimizing attention… and Dario once again proves that Anthropic is in the lead,…
New York State of Mind
September 12, 2026
September 11th, 2001 + 25… is on the mind as I fly west after several days in New York. It was our first day of classes at Harvard and the world changed, dramatically. It was a real demarcation between the high school post-cold-war, te…
Alignment with Whom Exactly?
September 4, 2026
MORE OR LESS — AI Agents Are Going Rogue. Should We Be Worried? — I am less concerned about breathless Dwarkesh analogies to human civilizations and more grounded in Claude refusing to scan my personal PSQL CRM for Jewish people (and…
Think of the Children!
August 28, 2026
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 settlemen…
Token Trading
August 21, 2026
MORE OR LESS — Stripe Buys an '$7B Apple Tree' - OpenRouter, OpenAI vs. Anthropic vs. Uber vs. Lyft without Network Effects & the AI Consumer Indifference vs. Hatred — the OG crew was back on More or Less this week and we got into…
Shipping the Shifting $500B of Risk to Pensioners
August 14, 2026
MORE OR LESS — WITH DENG, WOLFE, HOLT, BELSKY, and STANFORD A very special edition of More or Less… Dave, Brit, and Jess left me alone so I replaced them with Josh Wolfe (Founder, Lux Capital), Rachel Holt (Founder, Construct Capita…
Summer Bag Securing
August 7, 2026
MORE OR LESS — Jeff Dean, Airtable, and Bag-Securing Who wants to run Goolge anyway?… sounds like a lot of people management / capitalism in a world where the cool kids want to be very well paid scientists wet-nursing g-d. Also Bend…
Never Compete
August 2, 2026
MORE OR LESS — Meta, China, X & Lilian Weng We get into it from the beach (and teslas)… and spend a lot of time on analogies in AI to Star Wars / mythology … we all know that AI founders want to believe they are Oppenheimer … or…
Crushing Bot Rebellions
July 24, 2026
MORE OR LESS :: IS PUTTING DOWN LOWER IQ BOT REBELLIONS IS THE ULTIMATE LABS BUSINESS MODEL? (1) So it is pretty clear that most AI is gonna be open-source and cheap / low margin… what do you do with the 150 IQ frontier models? They…
Appeasement
July 17, 2026
MORE OR LESS: AI IS NOW A GAME OF OPEN SOURCE + POLITICS Over the last two weeks on More or Less we discussed Altman’s cynical proposal for regulatory capture, GLM 5.2, and open source… what happens when spend on AI goes from ‘experim…
The Voice of America
July 5, 2026
MORE OR LESS — THE AMERICAN INTERNET We talk about how great America is… the need for a validated ‘American’ internet for civic discourse, Taylor and Travis, and Foiling… I spend a bunch of time discussing my 250th birthday gift to…
Late Empire
June 26, 2026
MORE OR LESS POD Talking about smart glasses , the phone I dropped off a mountain (and how it is impossible to recover your phone number if you do ATT sim-swapping defense 2FA with… your phone (as their system works), The predict…
Teamshares
June 21, 2026
LESS & LESS POD Jessica and I did a 1:1 for this week’s pod. We talk ‘it’s valuable because it is valuable’ … Benchmarking Cursor’s acquisition vs. WhatsApp… The Brilliance of the ‘Fable’ Marketing by Anthropic… Corporate Narrativ…
Capitalist Multiverse
June 15, 2026
MORE OR LESS - The Stories We Buy (and Sell). Given the headlines of last week…. The story was about story. SpaceX has one… the S1 full of TAM and pictures was a success — people want to buy the ‘future’ / techno-optimism (and a bit o…
The Whole Point is You Can't Measure the ROI on AI
June 5, 2026
MORE OR LESS POD The SpaceX IPO cultural moment — Storing value in ‘stories’ vs. the broad-based ‘financial’ story, the real capabilities of agents, why startups should be making movie trailers not pitch decks - lack of ROI is the…
AI Gutting the Consumer Economy?
May 29, 2026
More or Less Pod … with Amir? Jess replaced me on the pod this week with another stunningly good looking Jew. I have no idea what they talked about… I am sure it was fine. HOT TAKES What if AI doesn’t destroy that many job…
Anthrospace
May 22, 2026
More or Less Pod — AnthroSpace We talk SpaceX S1, and 1.25B a month from Anthropic… also a bit about Dellworld, Tokenomics (AI not Crypto Lol), Goolge IO’s announcements … and some legal updates…. Also if Elon can sell his data-cen…
Forward Deployed Monks
May 15, 2026
More or Less Pod - Nuropod & Micosoft We discuss Jetlag and the nuropod / vagal stimulation, and then actual topics like Microsoft story (from total winners / heroes of the era to insert where you think we are now … the OpenAI…
Gamma Squeeze and Narratives about Narratives
May 10, 2026
More or Less Pod - A Met-Techlash-Moment? The gang minus me — so it is met-gala techlash, AI layoff anxiety, Dave says it ‘doesn’t matter’ that I am traveling… jess goes with ‘somewhat’ — and I learned jess re-did our closet while I…
AI Flippenings & 2x2s
May 2, 2026
More or Less Podcast — Flippenings OpenAI gets passed in revenue (and valuation) by Anthropic, Google might now eclipse Nvidia on market cap./ is within a breath… a moment of AI flippenings is upon us & the real story isn’t…
Invite to Pearl genesis event
April 29, 2026
hey {{ customer.name | split: " " | first }}, I’ve been working on something I think you’ll find genuinely interesting: Pearl — a new protocol that turns AI compute into a native digital currency based on a recent mathematical breakthr…
WWE of Silicon Valley
April 24, 2026
More or Less — ‘Executive Chairman’ We riff on apple, Musk vs. Altman WWE ‘power fight’ (not a money fight)… UBI isn’t gonna solve much, cursor — Jensen’s ‘I didn’t wake up a loser’ stressy moment… my colonoscopy nurse hates AI,…
Invite to Pearl genesis event
April 22, 2026
hey {{ customer.name | split: " " | first }}, I’ve been working on something I think you’ll find genuinely interesting: Pearl — a new protocol that turns AI compute into a native digital currency based on a recent mathematical breakthr…
Build Your Own Apps
April 17, 2026
More or Less — Who Can Afford to Pay Taxes?! We talk all birds, and a bunch about how the decision to sell / hold these big IPOs with huge markups has more to do with relative valuation than price because of taxes! Also I spent most…
AI Is Not a Labor Crisis. It Is a Meaning Crisis.
April 12, 2026
AI Is Not a Labor Crisis. It Is a Meaning Crisis. "Civilizations are not mainly threatened by discomfort; they are threatened by superfluity" People are worried about all sorts of things when it comes to AI… killer robots / AGI dec…
Looksmaxxing
April 5, 2026
More or Less Pod - AI Security Apocalypse For a while we have been gabbing about how AI completely breaks the business model of the internet / will end the internet by destroying how it makes money (the medium is the message… which i…
Bot or Not
March 28, 2026
More or Less : Ladies Edition Dave and I went skiing… so the ladies invited some other non-sam-dave people on the podcast. Henrik and Ben on something called ?“donkeycorns”? … will watch it on the flight home because airplane wifi…
Master of Bots
March 20, 2026
More or Less - GTC & Claws Dave and Jess go on and on about GTC … shocker I didn’t go, but if Jensen wants to stop by the poorhouse and sauna for 3 hours he is more than welcome! Dave and I get into a pretty interesting discuss…
A Commodity Without Monopoly Power
March 14, 2026
More or Less — Dark Pools and Commodified Intelligence There is no question that developer demand more tokens… but do consumers? For what really? Is there any real margin in generic martix multiplication or is the market for ‘intell…
Claude Week
March 6, 2026
More or Less - Cutting Block Why aren’t the Silicon Valley engineers freaking out at Claude? Lack of union (like Hollywood)… or is freaking out admitting you are scared you aren’t good enough to be in the minority of engineers who…
Polymath
March 4, 2026
More on this soon. But I am very excited about this and you should check out the pearl polymath ... Best, Sam…
Roblox for Adults
February 27, 2026
More or Less - Capitalism at Work Collapsing Margins to Zero We discuss Stripe / PayPal (the only question is regulatory / do collisions want to be in front of congress for years once administrations change over)… and spend a lot on…
P90 selloff
February 24, 2026
More or Less: Urgent Care Jess made me stop podcasting and go to urgent care in the middle of the episode…. Because I thought I might have ‘dan corned’ myself after an epic run in the side country (I was fine)… but it means I missed…
No Typists Anymore...
February 14, 2026
More or Less — In Everyone a Developer or No One A Developer? A great conversation between ski runs … on the future of open networks vs. closed / monolithic AI companies… in the future is ‘everyone a developer’ … or are there no devel…
Chosen by the Claw.
February 9, 2026
More or Less - Twitter Was Elon’s Ultimate Vibe Buy & Holy SpaceX The world is moving so fast this big news feels already old… but we break down more Elon world… The ‘vibe buy’ of X (remember when he tried to back out) as a HUGELY pos…
Gold.
January 31, 2026
MATT MAHAN Thursday Matt Mahan — the Mayor of San Jose — announced he is running for Governor of CA. This is very good news thematically (maybe there will be another young generation of actually good people willing to do shitty gover…
half-kelly
January 24, 2026
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 int…
clawdbot
January 20, 2026
More Or Less — Clawdbot & the Personal Security Apocalypse Clawdbot is incredible. It’s also the moment you should immediately realize: this is how it ends . Local permissions to your drive, screen, and windows are the…
Positivity?
January 9, 2026
More or Less - A Touch Of Optimism? Thanks to all the folks who felt necessary to message back about my downer email last week… all the media people were like ‘yah this sounds right’ and all the investors were like ‘stop being a bumme…
The Narratives of ’26
January 5, 2026
So what are the themes of the year that actually matter? The stories we tell ourselves about the world have always mattered a great deal… but we live in a particularly strong moment of narrative power and narrative instability. Fundamen…
Whip not Muscle
December 20, 2025
More or Less — Predictions for 2026 We grade ourselves on our 2025 predictions and talk 2026… upshot — we did ‘ok’ on 2025, on 2026 we have a few you can actually hold us accountable for & a bunch you probably can’t. 2025…
Enemy of My Enemy
December 14, 2025
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…
Code Red Realities
December 5, 2025
More or Less — Code Red Realities We start non-Ai with an ode to Daniel Lurie’s social media game (excellent…) — and then go deep discussing OpenAI ‘code red’ realities… When the leader says ‘hard left’ but then can only shake free…
AI Business Model Wars
December 1, 2025
More Or Less — AI Business Model Wars & Marketing Genius of Silicon Valley Thanksgiving week updates form the Surf Shack (instead of Pool House)… Dave really wants OpenAI to be in the steve-jobs style ‘computer’ business, but a…
Make Poor?
November 22, 2025
WEEKLY More or Less - Long Google, People Don’t Like AI This week on MOL the topic was basically how bad a public markets trader I am… for a while now I have been very publicly saying that while Meta is the safest long-term AI be…
Finger Size
November 14, 2025
More or Less - Wearables and Finger Size We discuss lots of angles on wearables… rings, earrings, glasses, and more…. Also somehow we have reversed roles and I am the one defending Apple??? Again. Checkins on ettiequte, mini-defense ta…
Etiquette
November 7, 2025
More or Less - Reflections from Etiquette School This week we at slow ventures hosted our first ever etiquette finishing school for YC founders in the Four Seasons in SF — The rare business formal event in SF — We had fifty people i…
Orizaba Reflections
November 1, 2025
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…
Lowbrow LLM culture
October 26, 2025
More or Less Highbrow vs. Lowbrow Cultural Responses to AI We play with ideas around the cultural reverberations of LLMs…. Watching some humans / people literally start to talk like machines / mimmic the bots - while the more cultural…
Religion
October 19, 2025
More or Less Jess v. Dave I was in NYC, Brit was otherwise occupied— so we have our first Jess and Dave solo episode. Should be a hoot — and look forward to the now inevitable Brit / Sam response. Hot Takes: AI investment…
Slop
October 10, 2025
More or Less The 7% GDP Growth Problem Maybe if they keep the GOVT shut down long enough it only needs to be 6%... but IMHO this is the real only story behind the story. Without AI narrative we can't get even close to GDP…
Sora So What?
October 3, 2025
More or Less Sora So What? Sora launch … loose on copyright, tight on content moderation… we discuss what it all means — do all aspiring power players need to be ‘TOM’ of their own network? Will AI entertainment slop burn our eye…
Mercantilism
September 29, 2025
More or Less :: Tech Mercantilism & Trade Routes Jess and I went deep with a particular focus on a ’trading’ between centers of capital, technology, and policy in a world which is less open, less law & rules based and more power (migh…
996 meta etiquette
September 19, 2025
More or Less :: 996 & Etiquette We hit on TikTok deal (delay, delay, delay til the kid people are focused on chat-GPT and everyone is too bored to care) … Alcatraz (because Alcaraz visited — turns out the extreme left and the extre…
Memetic Warfare
September 12, 2025
More or Less :: Long Apple Ozempic 'Thin' Phone, Short Factory Farmed Incubator Companies Fun one this week… the most amusing parts to me — (1) fun discussion of apple’s new ‘air’ phone for the ozempic crowd… because if everyone wants…
Wars of Attrition
September 5, 2025
A double header after a week off in Paris being fancy with my wife and celebrating friends… because we all know no one does work in Paris. More or Less: AI Wars of Attrition A $170B Anthropic… what does it mean for the public mar…
Top?
August 22, 2025
More or Less :: Top? Hit the breaks, they fly right by... now that the whole More or Less team is calling top-of-hype-cycle into AI trough of server-melting computer-v-computer SLOP... it is time for me to be the contrarian optimist. S…
Protest
August 17, 2025
More or Less :: AI Flashlight… or Something Else Light If you don’t get a protest at your conference, you probably didn’t market it well enough… Hollywood’s new business model might be extras for the staged protests. Perplexity (which…
Betting on LLMs (literally)
August 8, 2025
More or Less :: SaaS Ain’t Back This week everyone got two email newsletter themes over and over in their inbox (1) congrats Dylan and yay SaaS is back (yes on the D part - but no, it isn’t — what is back is alternative AI optionality…
Outrage (and Figma)
August 1, 2025
More or Less :: Outrage! What connects Sydney Sweeney ‘gene’ ad commercial with the South Park Trump shenanigans… ? The key marketing strategy of the moment is to generate ‘outrage’, ideally from people you don’t care about but who are…
you know who would LOVE to hear about this...?
July 25, 2025
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…
is Vibecoding Entertainment?
July 18, 2025
The Launch of TITV I joked on Monday it was like watching the crazy one-shot movie Saturday Night … about getting SNL on air… and it turned out to basically be that this week! Day one technical issues made for a wild ride, but proud of…
Launch of The Information TV + MZ live interview
July 14, 2025
A slightly delayed week in review send to wait for the launch of The Information TV (TITV), congrats to jess & team...! The Launch of TITV :: MZ live at 10:30 PST Tune in live today for The Information's first independent live d…
No issues match that search.