The Ledger

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Opinion
Sam Lessin: General intelligence AI is low-margin and a terrible business
“There's just general intelligence, it's low margin, it's, I mean, it's great, I'm, like, literally building stuff as we talk, I'm, like, into it, but I think it's a terrible business.”
Sam Lessin Mar 6, 2026 ▶ 9:07 Fire Sam Altman, The End of Software Engineers, and Why AI Is All Narrative · More or Less Podcast
Opinion
Lessin: Seed Stage VCs Are Paid Unbelievably Well to Do Almost Nothing
“My view is seed investors get paid unbelievably well to do almost nothing. And like the trade is we get paid incredibly well when it works, but we lose money constantly. And like, that's completely fine.”
Sam Lessin Jun 21, 2024 ▶ 26:49 #52: Elad Gil on What to Build in AI (Part II) · More or Less Podcast
Disclosure
Lessin: Slow Ventures invests $2M for 5-10% of creators' 30-year earnings
“We've started in the last two years financing creators specifically. So people who have like a big YouTube following a specific niche and saying, Hey, we will give you two million bucks for five to 10% of whatever you do over the next 30 years.”
Sam Lessin Nov 17, 2023 ▶ 24:26 #23: Why (and How) SMBs and Creators Will Win With AI, the New Financing Contracts, and More · More or Less Podcast
Insight
Lessin: Provocative headlines paired with reasonable screenshots generate viral deal flow
“And then if you make it a punchy headline so people get mad, but then say something reasonable in the screenshot that most people don't read, it gets packaged and sent all over the place, and then smarter people will give you better ideas and send you a compan…”
Sam Lessin Dec 5, 2025 ▶ 16:19 Code Red, Bitcoin Costs, AWS Resurgence, and Waymo Safety (Not About AI... ish) · More or Less Podcast
Disclosure
Lessin: Slow Ventures will not hire new associates who cannot code
“And I gotta be honest, like, I don't want to hire anyone who can't code anymore. Like, and like coding, what coding means is a little different, right? But like, you need to be as good as doing this stuff as me or better.”
Sam Lessin Jun 27, 2025 ▶ 11:19 #105: Tesla, Bumble, And Bezos' Wedding - Everything Is A Mess · More or Less Podcast
Disclosure
Lessin: Slow Ventures avoids investing in mass entertainers like MrBeast.
“We would not invest in general entertainment is too competitive, right? Like I actually wouldn't invest in like beast or things like that. It's much more about these are like niche communities. It's like aviation is a great area to look into or like lawn care …”
Sam Lessin Feb 14, 2025 ▶ 53:41 #86: Elon’s $97B Curveball For OpenAI · More or Less Podcast
Insight
Lessin: Founders Can Build Massive Companies on One $2M Seed Check
“With a two million dollar initial check, and the right iteration, and the right founder, and the right setup, you can build massive companies, like, with no outside capital.”
Sam Lessin May 24, 2024 ▶ 33:09 #48: Move Fast (But Don't) Break Silicon Valley · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures Targets Niche Creators With Zero CAC Advantage
“The way we've been playing this is our creator investing strategy, right? Which is you find creators, right, who have built cults around them in super specific verticals where they are the trusted brand, right? Whether it's in lawn care or terrariums or someth…”
Sam Lessin May 17, 2024 ▶ 43:47 #47: Algorithm-Proof Media and New Twists in the AI War · More or Less Podcast
Insight
Sam Lessin: Founders Must Skip Mid-Stage Funding With Profitability
“Take a few million bucks, go build a business that fucking works. You have to skip the middle with having a profitable business that works. So you never need the middle and then you come out the other side or you have a very profitable business.”
Sam Lessin Apr 26, 2024 ▶ 25:32 #44: The $1B AI Girlfriend Market, the Tech Hedge Fund Fallout and Why VCs Can’t Quit AI · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures buys equity in influencer holding companies
“We've been spending now for the last several years building this practice where we're, I think we're the only venture firms, the only ones that will literally write an equity check Not into a C Corp, right? But effectively into a holding company that represent…”
Sam Lessin Feb 23, 2024 ▶ 46:52 #35: 2024 IPO Dreams, Apple's Sports Game and Reddit's Biz Gamble · More or Less Podcast
Insight
Lessin: AI Empowers Big Platforms and Micro-Startups Over Mid-Sized Firms
“AI clearly benefits the really big platforms. I think we can all, I think we all agree with that, right? Like if you're a huge platform, you're going to make bank, right? Cause it's just obvious how to slot in and make your ads more performant or like things l…”
Sam Lessin Nov 17, 2023 ▶ 16:33 #23: Why (and How) SMBs and Creators Will Win With AI, the New Financing Contracts, and More · More or Less Podcast
Disclosure
Sam Lessin: He will never fund a pure product CEO again
“I'm not financing product people who don't know how to build a business anymore, right? No way, right? Like, I'm financing people who know how to take my three million dollar seed check, And build a good business, which then someday becomes a great business. A…”
Sam Lessin Oct 27, 2023 ▶ 28:43 #20: The New Founder Mindset: The End of the Product-Focused CEO · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures' profitable hardware startups were saved by acquisitions
“And like, the reality is, of the hardware companies, even that we've made money on, it's mostly because someone big bought them because the product was so good, and one generation later, it would have died, right?”
Sam Lessin Sep 15, 2023 ▶ 29:30 #14: The Apple Episode (Carbon Neutralish) · More or Less Podcast
Opinion
Lessin: Meme coin infrastructure is dramatically better than early NFTs
“The 20, 25 version of the tools and the infrastructure around this stuff is so dramatically better than like the early NFT, which was also an attempt at doing narrative investing, but it was a pretty bad attempt at narrative investing. This is like a much more…”
Sam Lessin Feb 28, 2025 ▶ 19:43 #88: Meta’s $200B AI Bet, Instagram Reels & The Future of Content · More or Less Podcast
Disclosure
Lessin: Slow Ventures is hesitating to fund a startup for being remote.
“There's a startup we're looking at that's that we like, but it's remote. And we're like, eh, we don't love what they're about.”
Sam Lessin Feb 14, 2025 ▶ 6:20 #86: Elon’s $97B Curveball For OpenAI · More or Less Podcast
Insight
Sam Lessin: Momentum investing fails at the seed stage
“The problem with doing it at seed is that the lead time from when you invest to the realization is so long that you might have gotten in front of the parade, but that doesn't mean you made any money. Whereas if you do it in the public markets, it's great, righ…”
Sam Lessin Nov 15, 2024 ▶ 28:33 #73: Elon to Lead DOGE, Bitcoin Surges & the Trump Alliance · More or Less Podcast
Disclosure
Sam Lessin: Slow tells founders to shut down failing companies
“All the founders know that if you're working with offline and slow, we're gonna tell you to shut your fucking companies down when they're not working.”
Sam Lessin Mar 22, 2024 ▶ 31:46 #39: How (Not?) to Exit Your AI Company, Analyzing the New Google-Apple Tie Up · More or Less Podcast
Disclosure
Sam Lessin: Metropolis used private equity to acquire incumbent parking operators
“And, you know, that's what we did with this Metropolis deal, which is pretty interesting. We're like, we had better, you know, the Metropolis team had better software for operating parking garages, but it just turned out that for a bunch of structural reasons,…”
Sam Lessin Jan 26, 2024 ▶ 14:08 #31: Fintech Struggles, Netflix Rises and 'Big' is Winning · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures Is Actively Backing New Franchise Models
“Franchise models, which historically VCs hate, we've started doing a bunch of them, right? And financing interesting new franchising models are really cool”
Sam Lessin Nov 17, 2023 ▶ 27:30 #23: Why (and How) SMBs and Creators Will Win With AI, the New Financing Contracts, and More · More or Less Podcast
Opinion
Sam Lessin: NBA franchises and blue-chip sports teams are priced to perfection
“I actually was looking at an NBA deal recently. We're not buying an NBA team or a piece of one, but I was looking at someone selling a piece of one. I was looking at the economics and like, they're so expensive, right? When you look at like what you pay per do…”
Sam Lessin Aug 11, 2023 ▶ 35:04 #9: How to save ESPN. Barstool’s Bad (Good?) Example · More or Less Podcast
Insight
Sam Lessin: Investors should back creator holdcos, not single projects
“Finance the Hold Co. Finance the creator holistically. Do not finance single projects of the creator because for two reasons. It's bad for the creators and it's bad for you.”
Sam Lessin Jun 23, 2023 ▶ 26:44 #3: Mr. Beast's burger bust and will M&A ever return? · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures does zero outbound sourcing or automated market mapping
“Candidly, we don't do outbound sourcing at all. There are companies, there are venture firms inside wherever they're built machines for outbound and market mapping. I don't do any of that. We say shit on the internet and then people email me.”
Sam Lessin Jan 16, 2026 ▶ 40:45 SaaS Companies Beware: AI Is The New UI (Anthropic's Claude Code and Cowork) · More or Less Podcast
Assertion Not checkable as stated
Lessin: Slow Ventures received hundreds of applications for founder etiquette school
“We have an event space... And we've had like hundreds of applications to it.”
Sam Lessin Sep 19, 2025 ▶ 26:18 #117 TikTok’s New Owner and Hiring a US CEO? · More or Less Podcast
Disclosure
Sam Lessin: None of my personal creator currency investments have worked
“I have invested in a ton of them. They have, none of them have worked.”
Sam Lessin Aug 22, 2025 ▶ 48:24 #113 GPT-5 Disappoints: The End of the AI Gold Rush? · More or Less Podcast
Disclosure
Sam Lessin would never invest in OpenAI personally or professionally
“Like I would never invest in, I wouldn't invest in it. Anyway, you slice it for my fund or personally, because it doesn't fit my risk reward profile at all.”
Sam Lessin Jul 25, 2025 ▶ 20:55 #109 OpenAI vs Google: The Real Business Model War Begins · More or Less Podcast
Disclosure
Lessin is building an AI clone of himself to screen founder pitches
“Before you call me, here's all my tweets and everything I've ever written, and it's all, I've only, so far, I've only pulled the tweets in, and I'll pull everything in, and just be like, try it out. Like, if I'm just gonna shit all over it, don't pitch me. But…”
Sam Lessin Jun 13, 2025 ▶ 31:39 #103: Are Silicon Valley’s Mega-Deals Just Talent Grabs? · More or Less Podcast
Disclosure
Sam Lessin: Highway 101 billboard cost low tens of thousands
“Oh, it's like barely in the low tens of thousands for a month.”
Sam Lessin Mar 7, 2025 ▶ 18:16 #89: America’s Crypto Reserve, Nvidia’s $600M Hit & Digg’s Comeback · More or Less Podcast
Disclosure
Lessin: Slow Ventures closed a $60M creator fund backed by MIT.
“We closed our creator fund, sixty million dollars of institutional capital from really serious people like MIT and Michigan and Rutgers”
Sam Lessin Feb 14, 2025 ▶ 42:27 #86: Elon’s $97B Curveball For OpenAI · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures replaces resumes with digital video interview tool
“I built this platform standard aptitude where, which is basically just for who we're going to hire as associates at slow. And like, what does it make you do? It's like, well, I don't want to see your resume anymore. If you want a job, you know, there's like an…”
Sam Lessin Sep 20, 2024 ▶ 29:22 #65: Instagram, YouTube and the Kids · More or Less Podcast
Disclosure
Sam Lessin: Three Slow Ventures Portfolio Companies Shut Down This Week
“At least three companies this week have said bye-bye that should have said bye-bye to us, which is great.”
Sam Lessin Aug 23, 2024 ▶ 54:18 #61: The Venture Capital Reset Era · More or Less Podcast
Insight
Lessin: The most successful early-stage investments appear dead for years
“Most of the things I out of the gate thought were working ultimately didn't. They're the things that I had fundamental beliefs on and every single thing that I feel really proud of investing went through a several year period because we go so early of like, oh…”
Sam Lessin Sep 1, 2023 ▶ 22:59 #12: Inside the VC brain · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures backs creators using personal equity contracts
“I mean, we've financed several, we've been set, financed several at SLO, several creators this way and we can get into that and things like that.”
Sam Lessin Jun 23, 2023 ▶ 25:27 #3: Mr. Beast's burger bust and will M&A ever return? · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures invested $3M in Airtable at $90M valuation
“So I put a three million dollar check into Airtable at a 90 post in between rounds early on, because this is now probably in 2012 ish, maybe that era.”
Sam Lessin Aug 7, 2026 ▶ 19:57 Jeff Dean Leaves Google, Airtable Sells, and the Bag-Securing Era · More or Less Podcast
Assertion Not checkable as stated
Sam Lessin sourced a dozen venture deals via viral screenshot essays
“So I've done, like, probably like a dozen investments where I put out something nuts, or maybe I don't think it's nuts, but some people do, and they get better stuff. Everything from Area Two Farms, which we seeded was from a screenshot essay.”
Sam Lessin Dec 5, 2025 ▶ 16:32 Code Red, Bitcoin Costs, AWS Resurgence, and Waymo Safety (Not About AI... ish) · More or Less Podcast
Assertion Not checkable as stated
Lessin: Slow Ventures received international requests to run Silicon Valley etiquette schools
“We've had requests from all over the planet to come run etiquette schools in various cities. Like literally, we have Asian, we have an Asian request. We have a Middle East request. We have several in Europe.”
Sam Lessin Nov 14, 2025 ▶ 38:50 Apple’s iPhone Sock, Waymo's Bay Area Expansion, and AI Wearables · More or Less Podcast
Disclosure
Morin: Slow Ventures and Offline Ventures never submit data to investor rankings
“When I was building Slow Ventures, we were non-attribution. We never submitted data, right? And so we like, we're never on any of these lists. We do the same thing at offline. We really are non-attribution. We don't submit data, right?”
Dave Morin Aug 29, 2025 ▶ 43:11 #114 Seed Rounds at $2B? The Dangers of AI Hype in VC With Tony Conrad · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures led investment in Sunil Rajaraman's Hamlet
“There's a version of this, I think, that we actually invested in, we're lead investors, and I'm really excited about it, that is working, right, and there's actually a blog associated with it, you know, which is called, which, oh, it's, you know, you must know…”
Sam Lessin Jul 18, 2025 ▶ 24:27 #108 Meta vs. OpenAI: Who Wins the Next Attention War? · More or Less Podcast
Disclosure
Morin: Slow Ventures evaluated and passed on Juul cannabis vaporizer spinoff
“Juul spun out a cannabis related vaporizer that we looked at it slow. Didn't end up doing it. The deal didn't work out.”
Dave Morin May 30, 2025 ▶ 10:27 #101: The Business of OnlyFans, Future of Identity, and Navigating Privacy in the AI Age · More or Less Podcast
Disclosure
Dave Morin: Slow Ventures is currently returning cash distributions to LPs
“Slow is doing distributions.”
Dave Morin Jun 23, 2023 ▶ 14:40 #3: Mr. Beast's burger bust and will M&A ever return? · More or Less Podcast
Disclosure
Lessin plans to buy a $25k satirical AI billboard on Highway 101
“Instead of eight million dollars, I'm gonna spend 25,000 dollars and have a hilarious billboard. I'm very excited. It's one of those things, like, I'm gonna submit it as an expense to the venture firm, and if they reject it, it's okay.”
Sam Lessin Feb 7, 2025 ▶ 1:08:28 #85: The $250M Meme Coin Experiment · More or Less Podcast
Disclosure
Sam Lessin: Slow Ventures was the premier dog startup investor
“Slow Ventures is the, was, I'm not sure we still are, but was the premier dog investor for many years. We were like the dog VC.”
Sam Lessin Nov 3, 2023 ▶ 3:50 #21: AI Regulation, War and the Future of the American Tech Stack · More or Less Podcast
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