The Ledger

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Sam Lessin: Negotiating term sheets in a sauna gives edge over founders
“I have negotiated one term sheet in a sauna with the founder. It's a great idea, because, especially if they're not used to the sauna, because you have the edge. You can just keep cranking it up.”
Sam Lessin Nov 14, 2025 ▶ 22:55 Apple’s iPhone Sock, Waymo's Bay Area Expansion, and AI Wearables · More or Less Podcast
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Sam Lessin: I am personally short Ethereum and long Solana
“You know, I'm very sure the Ethereum world. I'm very long. Dave Morin: Solana. Sam Lessin: It's a personal book.”
Sam Lessin Jan 4, 2025 ▶ 43:57 #80: More or Less Holiday Special Pt. 2 (Crypto and Antitrust) · More or Less Podcast
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Khosla tells his portfolio startups to completely ignore AI compute costs
“My advice to all our startups is ignore the cost of compute, because any assumption you make, any dollar you spend on optimizing your software will be worthless within the year, and so forget about it.”
Vinod Khosla Dec 27, 2024 ▶ 45:00 #79: The More or Less Holiday Special Pt. 1 (AI Highlights) · More or Less Podcast
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Sam Lessin vows he will never hire student campus protesters
“Although I'll never hire any of them.”
Sam Lessin May 3, 2024 ▶ 18:28 #45: How Tech Cos. Quit the Culture Wars · More or Less Podcast
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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
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Brit Morin: Target knocked off Brit & Co products with private labels
“Brit and co had a lot, had many lines with target and what happened target hired a new chief merchandising officer targets, bottom line started hurting. So they decided to go private label for like half of the products they formerly were buying and just kind o…”
Brit Morin Aug 4, 2023 ▶ 14:41 #8: Where's the Barbie business pop? Why brands beat marketplaces · More or Less Podcast
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Lessin: Gave AI full control of a Mac mini to deploy iOS apps via TestFlight
“So I actually just gave my cloud cloud and this thing's full control of a Mac mini down to screen, like full, full, full control. So that it can deploy through test flight all its own apps from single commands.”
Sam Lessin Sep 4, 2026 ▶ 7:42 AI Agents Are Going Rogue. Should We Be Worried? │Claude vs. Grok, Tesla vs Waymo, Google vs Canva · More or Less Podcast
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Sam Lessin algorithmically screenshots his son's iMessages all day to bypass Apple
“And like, by the way, you know, I have a desktop, like sitting in my computer in my room where I just like logged into my son's iMessage account. And I've sit there and fucking screenshot it all day long algorithmically. Cause there's no APIs to it. So I can p…”
Sam Lessin Aug 28, 2026 ▶ 34:19 Meta’s $17B Reckoning & Why Parents Can’t Compete With Big Tech's Algorithm · More or Less Podcast
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Rauch: Vercel candidates must explain how they would automate their own roles
“And so basically everyone at Vercel is now kind of like the steward of the agent, and that's their new job expectation. And now it's become part of our job screening, which actually forces the hiring manager to think about, I'm hiring a roboticist. I'm not hir…”
Guillermo Rauch Apr 10, 2026 ▶ 32:47 Vercel CEO: 70% of Our Traffic Is Now AI Agents "Nobody Was Prepared" | Anthropic, OpenClaw, OpenAI
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Dave Morin: OpenClaw Built Skill Approval System After Malicious Code Exploits
“Like we had to build an entire approval process now for skills because the skills that were going into the, that was the thing making open clause unsafe was that people would download a new skill and then there would be Instructions in there that would exfiltr…”
Dave Morin Mar 20, 2026 ▶ 50:19 Nvidia’s GTC Was “Taylor Swift for Straight Men” (Apple, OpenAI, and OpenClaw News) · More or Less Podcast
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Brit Morin: One-person AI startup Pulsia hit $2M ARR in two weeks
“We have this company, I think we mentioned last week called Pulsia. That's just like on a tear right now as a one person company. That's gotten from, like, zero to two million ARR in two weeks, and, like, the agent is just running the company.”
Brit Morin Mar 6, 2026 ▶ 32:36 Fire Sam Altman, The End of Software Engineers, and Why AI Is All Narrative · More or Less Podcast
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Sam Lessin says he launched the Jelly Jelly meme coin and held
“Which I launched, and the application has adopted, and it's driving, and the app is cool, it's got a lot going on, but it literally, like, is traded very heavily, and it's gone far beyond any expectation. Well, it's kind of, it's a wild thing about crypto, whi…”
Sam Lessin Nov 7, 2025 ▶ 37:29 Apple Chooses Gemini, Sequoia's Leadership Shake-up, and Meme Coins · More or Less Podcast
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Dave Morin: Founders are pitching AI-generated startups they don't even understand
“We have founders that show up and they will start showing me their idea and they'll clearly have vibe coded, whatever it is they're showing me. And they'll be trying to explain the idea. And it's clear they don't actually understand the idea and that the AI ac…”
Dave Morin Oct 3, 2025 ▶ 19:43 #119 OpenAI Sora vs. TikTok: Can “AI Entertainment” Fund the Compute Bill? · More or Less Podcast
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Conrad: True Ventures has paused investing in non-AI startups
“Like, I think it's just required us to just say, pause for a second on all things that are non AI, because we're going to have catch up like almost every firm, by the way.”
Tony Conrad Aug 29, 2025 ▶ 50:38 #114 Seed Rounds at $2B? The Dangers of AI Hype in VC With Tony Conrad · More or Less Podcast
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Sam Lessin says he recently achieved a 1,000x investment return
“Yeah, I did one of those recently.”
Sam Lessin Aug 1, 2025 ▶ 20:48 #110 Meta's Billion-Dollar Hires: Bubble or Genius? · More or Less Podcast
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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
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Jessica Lessin: The Information allows reporters to use AI for copyediting
“There is no reason, like AIs are excellent. And applying AP style when that's all you need. And so I'm announcing this new policy. I'm going to get so much shit at my all hands, which actually happens before this pod. So that's good. But like on the margin, li…”
Jessica Lessin Jun 27, 2025 ▶ 14:01 #105: Tesla, Bumble, And Bezos' Wedding - Everything Is A Mess · More or Less Podcast
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Sam Lessin Has Held Conversations About Acquiring OnlyFans
“I mean, I've had several conversations. I'd love to get in the direction. I think there's several steps to anything actually happening, at least in my corner, unfortunately, but my God, is it tantalizing?”
Sam Lessin May 30, 2025 ▶ 1:38 #101: The Business of OnlyFans, Future of Identity, and Navigating Privacy in the AI Age · More or Less Podcast
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Morin: I replaced every Zapier integration at Offline with AI-written code
“I ripped out every Zapier, you know, integration anywhere in our code base for offline. You can just replace it. It's, like, super easy. Like, there's no point.”
Dave Morin May 23, 2025 ▶ 51:59 OpenAI Teams Up with Jony Ive, Vibe Coding, Gemini, and More | More or Less #100 · More or Less Podcast
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Morgan Beller: A failing NFX portfolio company is sitting on $40M cash
“I have a company right now that's not doing well. And I was speaking to the founder last week and it's really not doing well at all. And they have like. Forty million dollars in the bank. And they shouldn't. Like, they don't deserve that money. They raised it,…”
Morgan Beller Apr 18, 2025 ▶ 37:01 OpenAI’s Social Network & Figma’s Potential IPO | More or Less #95 · More or Less Podcast
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Sam Lessin would sell his Wiz proxy shares at a 34% discount
“I'd be happy to hedge my tiny, tiny proxy whiz possession to someone at 66 cents on the dollar and have the cash now.”
Sam Lessin Mar 21, 2025 ▶ 34:47 #91: Google’s $32B Deal and a Silicon Valley Spy Scandal! · More or Less Podcast
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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
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Lessin: I have never sold and will not sell Jelly-My-Jelly
“I have not ever sold a jelly my jelly and I won't.”
Sam Lessin Feb 7, 2025 ▶ 8:49 #85: The $250M Meme Coin Experiment · More or Less Podcast
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Morin: Offline was a seed investor in Solana, believes it is superior
“I think you and I and all of us here on this pod have always thought, you know, that Solana is the superior technology. It's the most scalable. We were seed investors.”
Dave Morin Feb 7, 2025 ▶ 35:24 #85: The $250M Meme Coin Experiment · More or Less Podcast
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Sam Lessin: I bought 2% of Jelly Jelly to establish it
“We launched this thing as a fair launch. I bought, I put it out. I bought two percent of it for almost nothing to just establish it.”
Sam Lessin Feb 7, 2025 ▶ 43:51 #85: The $250M Meme Coin Experiment · More or Less Podcast
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Vinod Khosla: Khosla Ventures has never taken a dollar in management fees
“By the way, I, since I started the firm 20 years ago, I've never taken a dollar in fees.”
Vinod Khosla Dec 27, 2024 ▶ 48:59 #79: The More or Less Holiday Special Pt. 1 (AI Highlights) · More or Less Podcast
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Levie: Republican economic philosophy aligns more with my instincts than Democrats'
“And I think it's a, it's clearly a distinct philosophy from what the Democrats pitch. And it actually aligns, frankly, more to my instincts, but there's other things on the Democrat side that kind of social topics and others that, that, you know, sort of have …”
Aaron Levie Dec 6, 2024 ▶ 18:22 #76: In a World with 99.99% Accurate AI… (feat. Aaron Levie) · More or Less Podcast
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Aoun started his next company immediately due to investor demand
“Tuesday morning after this all happened, I said, I'm taking a break. And by Wednesday morning, because the investors said they want to come in and the employees said they want to come in. I said, I'm starting a company like without, and not only am I starting …”
Adrian Aoun Nov 22, 2024 ▶ 53:06 #74: Winding Down From a $400M Fundraise, or How to Move Forward After Forward (with Adrian Aoun) · More or Less Podcast
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Jessica Lessin: How a wrong number sparked a feud with Bill Gurley
“We thought we had Bill Gurley's cell phone. It turned out we had his gatehouse phone. So upon calling it, our reporters in our newsroom were just calling it, and he thought we were hiding in the bushes.”
Jessica Lessin Sep 13, 2024 ▶ 36:36 #64: Meta vs. Apple: the Future of Open vs. Closed Tech · More or Less Podcast
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Lessin: Extremely bullish on AI only for Google and Meta ads
“I'm, as, if you hadn't heard, I'm extremely long AI only in the case of ads optimization and making a shitload of money for Facebook and Google”
Sam Lessin Aug 9, 2024 ▶ 10:04 #59: Google: Can it Outrun Regulation? · More or Less Podcast
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Gil: Google canceling Maven prompted defense tech pivot and backing Anduril
“I started getting into defense tech when Google shut down Maven because I was like, oh my gosh, if Google isn't doing it, what a great startup opportunity, you know? So I started looking for defense companies and then I met Anduril and I was like, oh my God, t…”
Elad Gil Jun 21, 2024 ▶ 29:09 #52: Elad Gil on What to Build in AI (Part II) · More or Less Podcast
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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
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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
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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
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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
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Britt Morin relies on an annual $3,000 body scan instead of a doctor
“I don't have, like, an actual doctor. I go in once a year for a 3000 dollar body scan and all these tests.”
Brit Morin Jul 7, 2023 ▶ 44:04 #5: Twitter Won't Die! Long Live Threads! · More or Less Podcast
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Lessin repeatedly pitched that Facebook should acquire the DMV
“Peter, we used to have meetings for what we should buy, and my pitch was always that the Facebook should buy the DMV.”
Sam Lessin Aug 14, 2026 ▶ 20:56 Special Edition MOL with Josh Wolfe, Rachel Holt, Scott Belsky, Scott Stanford, and Peter Deng. · More or Less Podcast
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Morin: OpenClaw Partnered With Apple on Custom Mac Studios
“We've actually now worked in partnership with Apple to develop a bunch of Mac studios in custom configuration That is enabling us to unblock our engineering team's ability to be, you know, extremely productive.”
Dave Morin Jul 31, 2026 ▶ 35:06 The Lilian Weng Saga, Mental Health Essay Then OpenAI | Meta's AI Ad, China Cracks DUV
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Brown: Teamshares commits to never selling its acquired small businesses
“We think the permanent ownership is good for team share shareholders. We think it's good for the businesses themselves to not be for sale. And these are the promises that we're making when we go and, you know, look an owner in the eyes that we're going to buy …”
Mike Brown Jun 17, 2026 ▶ 48:59 Teamshares IPO: $60M EBITDA, 92 Companies, Zero Exits · More or Less Podcast
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Rauch: Vercel aims to become the AWS of agentic infrastructure
“So that's the focus of the company right now build being the AWS of agentic infrastructure.”
Guillermo Rauch Apr 10, 2026 ▶ 17:49 Vercel CEO: 70% of Our Traffic Is Now AI Agents "Nobody Was Prepared" | Anthropic, OpenClaw, OpenAI
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Jessica Lessin says she declined multiple offers to buy BuzzFeed
“I've been asked, and I said no every time.”
Jessica Lessin Dec 19, 2025 ▶ 40:43 Hype vs Reality: Our 2026 Predictions for Tech, Media, and Culture · More or Less Podcast
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Sam Lessin reveals he made two recent investments in 'lawfare' tech startups
“I've actually made two investments in the last 10 days in lawfare, because it's just clearly what's happening, right, which is like weaponizing the law in various ways for different groups, etc.”
Sam Lessin Nov 14, 2025 ▶ 52:40 Apple’s iPhone Sock, Waymo's Bay Area Expansion, and AI Wearables · More or Less Podcast
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Lessin invested a core check into a memetic warfare startup
“I put a core check into a mimetic warfare company, and I'm sure there are more coming.”
Sam Lessin Sep 12, 2025 ▶ 48:24 #116 iPhone Air or Pro: Apple Ignores AI and Wins? · More or Less Podcast
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Lessin says he would venture invest in an AI class action lawsuit bot
“If someone wants to pitch me a, I would venture invest in class action lawsuit bot, right?”
Sam Lessin Sep 6, 2025 ▶ 54:51 #115 Anthropic at $170B: Should Unicorns Be Forced to IPO? · More or Less Podcast
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Brit Morin: Using ChatGPT to evaluate follow-on capital allocation math
“There's a company in our portfolio that is doing really well. I was talking to GPT about like, how much follow on capital do you think this company should like, what is the potential outcome here? Like I was doing all of this math with GPT just to try to like,…”
Brit Morin Aug 22, 2025 ▶ 29:54 #113 GPT-5 Disappoints: The End of the AI Gold Rush? · More or Less Podcast
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Dave Morin pledges to always back his failed founders again
“So if you're a founder and you failed and we invested, call us for your second, third, fourth time. I will always invest.”
Dave Morin Aug 15, 2025 ▶ 19:26 #112 Swift Should Buy Chrome, Not Perplexity · More or Less Podcast
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Dave Morin: Investing Exclusively in Repeat Founders to Counter AI Diligence
“My answer to this has been, I'm going to work with founders that are second time, third time, that I know are extremely talented and are working”
Dave Morin Aug 8, 2025 ▶ 35:06 #111 Figma, OpenAI, Canva: Meme Stock IPOs in Silicon Valley · More or Less Podcast
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Ben Smith: Semafor staff must build their own AI tools, not developers
“I'm not letting them ask Our developers to help them build AI tools. Like you can really in Google app script without knowing anything about, I mean, you can really like vibe code yourself some nice tools”
Ben Smith Mar 28, 2025 ▶ 51:47 The Signal Scandal & DOGE Drama! (with Ben Smith and Nicholas Carlson) | More or Less #92 · More or Less Podcast
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