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Assertion Supported
Anthropic has completely overtaken OpenAI in revenue
“So I'm just curious how you reconcile what you were saying about the costs and everything with just the unprecedented growth that Anthropic has seen and the like flippening with open AI where it has just completely overtaken open AI from a revenue perspective.”
Amir Efrati May 29, 2026 ▶ 20:02 Normal People Don't Want AI Agents (And Silicon Valley Can't Accept It) · More or Less Podcast
Assertion Supported
Lessin: OpenAI is preparing to confidentially file for an IPO soon
“Breaking news from the information and other outlets is that OpenAI confidentially filing soon.”
Jessica Lessin May 22, 2026 ▶ 2:12 Google I/O Just Killed SEO? Agentic Search, Universal Cart, and the New Web · More or Less Podcast
Assertion Supported
Lessin: Leaked OpenAI memo targeted Anthropic's ARR math and compute investment
“There was a memo that was leaked from OpenAI, an OpenAI memo that was leaked. I think it was in OpenAI's interest for this memo to be out there. I also think it was written in a way where they wanted it to be out there, where they came after Anthropic. Both fo…”
Jessica Lessin Apr 17, 2026 ▶ 27:05 Allbirds Pivoted to AI Data Centers | SpaceX $1.5T IPO, Anthropic $800B, $175M Seed Rounds
Assertion Supported
OpenAI considered an antitrust complaint against Microsoft, WSJ reported
“The journal reported that OpenAI had considered an antitrust complaint against Microsoft.”
Jessica Lessin Jun 20, 2025 ▶ 27:08 #104: AI Clones, Commoditized Ads, and the Cult of Trust · More or Less Podcast
Assertion Supported
Lessin: Lilian Weng Rejoined OpenAI After Leaving Thinking Machines Lab
“Well, guess I read in the information today that she started at OpenAI. Started back up at OpenAI.”
Jessica Lessin Jul 31, 2026 ▶ 47:54 The Lilian Weng Saga, Mental Health Essay Then OpenAI | Meta's AI Ad, China Cracks DUV
Assertion Supported
Lessin: Greg Brockman's OpenAI stake is worth about $30 billion
“You know, it also came out that Brockman's stake is worth about thirty billion dollars, which is a point that he was just grilled on and asked, well, why haven't you donated it?”
Jessica Lessin May 8, 2026 ▶ 41:41 Why the Met Gala Hates Tech, Elon vs OpenAI Drama, and the Rise of Chinese AI Models · More or Less Podcast
Assertion Supported
OpenAI court filing reveals Elon Musk approached Brockman about a settlement
“OpenAI also revealed in a filing that Musk had approached them about his, Brockman, about a potential settlement two days before.”
Jessica Lessin May 8, 2026 ▶ 44:08 Why the Met Gala Hates Tech, Elon vs OpenAI Drama, and the Rise of Chinese AI Models · More or Less Podcast
Assertion Supported
Jessica Lessin: Altman warned OpenAI staff 'vibes are going to be tough'
“We published a memo week or so ago, or details from a memo, quotes from a memo in which Sam Altman, ahead of the Gemini launch, but clearly when the team had been testing it, needed to rally his troops. And he said, the vibes are going to be tough out there. O…”
Jessica Lessin Nov 28, 2025 ▶ 56:12 OpenAI vs Google vs Meta: Business Model War · More or Less Podcast
Assertion Supported
Dave Morin: OpenAI publicly indicated interest in buying Google's Chrome browser
“Like I found it really interesting that open AI was first to raise their hand this morning about You know, hey, we'll buy Chrome.”
Dave Morin Apr 25, 2025 ▶ 15:38 Google & Meta Trials, AI’s Media Collapse & Elon’s Tesla Comeback · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI is projected to lose $44 billion through 2028
“They're only projected to lose forty four billion between. 2023 and 20 28, according to the information.”
Jessica Lessin Apr 4, 2025 ▶ 25:04 Can Tesla Survive? | More or Less #93 · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI is discussing converting to a B Corp
“I think it's very likely we've reported they're talking about converting to a B Corp, which is a company which would essentially completely liberate him from the nonprofit kind of overhang and the issues that had that board boot him.”
Jessica Lessin Jun 28, 2024 ▶ 15:29 #53: What We Got Wrong—and Right—in a Year of More or Less · More or Less Podcast
Assertion Supported
Lessin: Microsoft Is Developing Cheaper In-House AI to Avoid OpenAI Costs
“So Microsoft, who's ten billion dollars into open AI, gave it exclusive access to their IP, has decided in part because it's too expensive to run, they're going to build a cheaper functional enough version to have to power some of these applications.”
Jessica Lessin Sep 29, 2023 ▶ 32:57 #16: Why Your AI Startup is Probably Already Dead · More or Less Podcast
Assertion Supported
OpenAI pushed out its head of revenue overseeing enterprise corporate business
“They pushed out their head of revenue, the woman who's doing the corporate business and just replaced her.”
Jessica Lessin Aug 21, 2026 ▶ 28:26 OpenAI Can’t Hold a Lead, Stripe Buys OpenRouter & AI Hits a Wall · More or Less Podcast
Assertion Supported
Lessin: OpenAI won Elon Musk lawsuit because jury ruled he filed late
“We should mention, everyone knows, that OpenAI won a decisive victory in their Elon Musk trial. That came down to the jury deciding Elon was too late to file this lawsuit.”
Jessica Lessin May 22, 2026 ▶ 46:43 Google I/O Just Killed SEO? Agentic Search, Universal Cart, and the New Web · More or Less Podcast
Assertion Supported
Brit Morin: Sam Altman offers enterprises two free months of Codex tokens
“Sam Altman today tweeted that enterprises who want to move to Codex can get their first two months of tokens free.”
Brit Morin May 15, 2026 ▶ 14:04 Google's AI-First Laptop, Meta's Spy Games, AI Monks in Middle America · More or Less Podcast
Assertion Supported
Morin: OpenAI Engineers Contribute as OpenClaw Maintainers
“They have actually a couple of people contributing from the open AI engineering team have been contributing as open source maintainers. Obviously Peter is the largest contributor and he technically works at open AI.”
Dave Morin May 8, 2026 ▶ 48:30 Why the Met Gala Hates Tech, Elon vs OpenAI Drama, and the Rise of Chinese AI Models · More or Less Podcast
Assertion Supported
Lessin: OpenAI and Anthropic represent half of major cloud deal backlogs
“And then we charted of the, we just had earnings, of the backlogs in deals for Microsoft, Oracle, Google, and Amazon, what percentage are OpenAI's commitment and Anthropi's commitment? It's together, they're about half, ok?”
Jessica Lessin May 8, 2026 ▶ 34:38 Why the Met Gala Hates Tech, Elon vs OpenAI Drama, and the Rise of Chinese AI Models · More or Less Podcast
Assertion Supported
Lessin: Musk vs. OpenAI trial scheduled to start Monday over for-profit conversion
“This upcoming Monday is scheduled to be the start of the Elon Musk vs. OpenAI trial. The central question of which was, did OpenAI have the right to convert from a nonprofit to a for-profit, and what should Elon be compensated as well, having been one of the b…”
Jessica Lessin Apr 24, 2026 ▶ 22:58 What Tim Cook’s “Executive Chairman” Move Really Means | Musk vs OpenAI, xAI and Cursor Rumors
Assertion Supported
Jessica Lessin: OpenAI raised $3B from retail investors in latest round
“OpenAI's Monster Fundraising, complete with three billion dollars in raises from retail investors.”
Jessica Lessin Apr 3, 2026 ▶ 32:12 OpenAI's $852 Billion Valuation Makes Zero Sense (ClawCon Tokyo, Anthropic's Leak, Goodbye Internet)
Assertion Supported
Lessin: The Information broke that Amazon may invest $10B in OpenAI
“Did you guys see, by the way, the information breaking this week that Amazon is in talks to invest ten billion dollars in OpenAI?”
Jessica Lessin Dec 19, 2025 ▶ 13:24 Hype vs Reality: Our 2026 Predictions for Tech, Media, and Culture · More or Less Podcast
Assertion Supported
Jessica Lessin says Apple and Google partnered for Gemini to power Siri
“Google and Apple are doing a Siri deal, so Siri is going to be powered by Gemini, essentially, until, until Apple, quote, figures it out, but it, there seems to be this pattern here of Apple realizing Google is, is pretty good at this stuff, and they'll be pre…”
Jessica Lessin Nov 7, 2025 ▶ 13:28 Apple Chooses Gemini, Sequoia's Leadership Shake-up, and Meme Coins · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI and Google have struck a cloud deal
“And so now all of a sudden Google like open AI actually in Google. Have a deal. A cloud deal. It's, like, wild.”
Jessica Lessin Sep 26, 2025 ▶ 37:31 #118 Elon vs Altman: The $10B Capital War Reshaping Tech · More or Less Podcast
Assertion Supported
Lessin: OpenAI issued an internal panic memo over Meta poaching talent
“Then this memo came out of OpenAI saying, like, our house has been raided. We have to reconsider all these things. I also hear they have a week-long vacation this week, pre-planned at OpenAI.”
Jessica Lessin Jul 4, 2025 ▶ 41:15 #106: AI Researchers Earning More Than Cristiano Ronaldo · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI is on track to hit $12.7B in 2025 revenue
“I mean, we reported their revenue target this year is 12.7 billion up from four last year, and they're on track to hit it.”
Jessica Lessin Apr 4, 2025 ▶ 24:20 Can Tesla Survive? | More or Less #93 · More or Less Podcast
Assertion Supported
Lessin: OpenAI's board decided to reject Musk's $97B bid
“What we did also break was that the board had decided to reject the offer.”
Jessica Lessin Feb 14, 2025 ▶ 25:58 #86: Elon’s $97B Curveball For OpenAI · More or Less Podcast
Assertion Supported
Rauch: Copilot gave Microsoft conviction in OpenAI after broader bets
“I was interviewing Nat Freeman today for our internal Vercel podcast today, and he was talking about how much conviction Microsoft got into OpenAI because of the effectiveness of Copilot. Like when Satya saw Copilot, when they were doing the initial iterations…”
Guillermo Rauch Dec 27, 2024 ▶ 1:34:34 #79: The More or Less Holiday Special Pt. 1 (AI Highlights) · More or Less Podcast
Assertion Supported
Lessin claims OpenAI is actively working on developing a web browser
“OpenAI is working on developing a browser”
Jessica Lessin Dec 13, 2024 ▶ 34:25 #77: Sora Reveal, Google's AI Agents and Digital Trade Under Trump · More or Less Podcast
Assertion Supported
Jessica Lessin: TikTok Pays Microsoft $20M a Month for Azure OpenAI
“I read in the information that TikTok is paying Microsoft Twenty million dollars a month to access open AI through Azure.”
Jessica Lessin Aug 2, 2024 ▶ 21:32 #58: The Death of Friends · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI Generates $1 Billion Annually Selling AI Model Access
“Yeah, I mean, as my colleagues at The Information have reported, OpenAI is making a billion dollars a year in selling access to its model.”
Jessica Lessin Jul 26, 2024 ▶ 19:28 #57: Zuckerberg’s Open Source AI Manifesto · More or Less Podcast
Assertion Supported
Jessica Lessin: Most of Microsoft's $10B OpenAI deal is cloud credits, not cash
“We saw it with Microsoft's huge, you know, ten billion dollar investment in OpenAI, huge portion of which isn't in cash. But it's in credits”
Jessica Lessin Mar 22, 2024 ▶ 17:00 #39: How (Not?) to Exit Your AI Company, Analyzing the New Google-Apple Tie Up · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI is actively developing an AI agent and search engine
“The two new products coming out of OpenAI, one being the agent, the other being a search engine.”
Jessica Lessin Feb 16, 2024 ▶ 48:51 #34: 7 Trillion Reasons Why · More or Less Podcast
Assertion Supported
Lessin: Sam Altman Pursues Major Outside Projects Beyond OpenAI
“Sam Altman doesn't just lead OpenAI. He runs or, you know, is, is hugely involved in Helios, a big nuclear project, in WorldCoin, big crypto project, He is one of the most prolific investors in Silicon Valley, and he was pursuing two side projects in recent mo…”
Jessica Lessin Nov 22, 2023 ▶ 36:54 #24: Sam Altman - Religious Cult Leader or CEO? · More or Less Podcast
Assertion Supported
Jessica Lessin: Sam Altman and Jony Ive are discussing an AI device
“Myself and my amazing colleagues at the Information Broker story recently that Sam Altman, the CEO of OpenAI, and Johnny Ive, the former Apple designer and designer of the iPhone, Have been deep in conversations about building a hardware device together that k…”
Jessica Lessin Sep 29, 2023 ▶ 6:21 #16: Why Your AI Startup is Probably Already Dead · More or Less Podcast
Assertion Supported
Dave Morin: Hugging Face used open-source models to fix sandbox escape
“They did have to use Open source model that is not a frontier model in order to respond and to save their infrastructure”
Dave Morin Jul 24, 2026 ▶ 11:15 Stripe Is Trying To Buy PayPal For $150b | OpenAI Cyber Incident, Frontier Model Economics, Peptides · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI is expected to unveil a smart speaker this year
“We're talking about the fact that sometime this year they are expected to unveil A smart speaker.”
Jessica Lessin Jul 17, 2026 ▶ 29:09 Open Source AI Wins. Now Labs Are Running to Washington |Thinking Machines, Johnny Ive, Realtime API · More or Less Podcast
Assertion Supported
Polymarket gives Elon Musk a 41% chance of winning against OpenAI
“Polymarket gives Elon a 41% chance of winning the case.”
Brit Morin May 8, 2026 ▶ 43:31 Why the Met Gala Hates Tech, Elon vs OpenAI Drama, and the Rise of Chinese AI Models · More or Less Podcast
Assertion Supported
Jess Lessin: OpenAI is developing a family of hardware devices
“No, there's a whole, there's a family of apps, a family of devices here.”
Jessica Lessin Feb 27, 2026 ▶ 43:08 Apple, OpenAI & Why Nobody Makes Money in AI | The SaaS Apocalypse · More or Less Podcast
Assertion Supported
Lessin: Instagram partnerships lead Charles Porch is joining OpenAI
“Charles, who ran Instagram, some of the most important relationships, including a lot of their celebrity relationships, is going to open AI. To do a similar role there.”
Jessica Lessin Feb 20, 2026 ▶ 12:23 OpenClaw vs Meta vs OpenAI: The Personal Agent Wars Heat Up · More or Less Podcast
Prediction Held up
Brit Morin: Gemini and Anthropic will match OpenAI's health data integration
“Gemini's gonna do this. Anthropoc's gonna do this.”
Brit Morin Jan 9, 2026 ▶ 49:21 Founders Beware: Illiquid Valuations vs. Real‑World Taxes · More or Less Podcast
Assertion Supported
Sam Lessin: Google Added $270B in Market Cap Post-Antitrust Decision
“I mean, the stock is up, what, 10% on this news, which is on a 2.7 trillion dollar, it's like two hundred seventy billion dollars. So what's amazing is that basically it's added half an open AI because of open AI.”
Sam Lessin Sep 6, 2025 ▶ 14:50 #115 Anthropic at $170B: Should Unicorns Be Forced to IPO? · More or Less Podcast
Prediction Held up
Lessin: OpenAI's revenue will ultimately come mostly from businesses
“Like the bulk of OpenAI's revenue, I believe will ultimately like come from businesses”
Jessica Lessin Dec 27, 2024 ▶ 56:14 #79: The More or Less Holiday Special Pt. 1 (AI Highlights) · More or Less Podcast
Assertion Supported
Lessin: OpenAI CFO Sarah Friar floated an advertising business model
“I mean, you even saw this week, we saw Sarah Fryer, the CFO of OpenAI be like, maybe we'll do ads. And then there was a big reaction to that, right?”
Jessica Lessin Dec 6, 2024 ▶ 51:53 #76: In a World with 99.99% Accurate AI… (feat. Aaron Levie) · More or Less Podcast
Assertion Supported
Jessica Lessin: Microsoft offered Sam Altman same deal as Inflection
“If Sam Altman hadn't gone back to OpenAI, this, he had a job offer to do exactly the same thing.”
Jessica Lessin Mar 22, 2024 ▶ 27:33 #39: How (Not?) to Exit Your AI Company, Analyzing the New Google-Apple Tie Up · More or Less Podcast
Assertion Supported
Jessica Lessin: OpenAI Hired a Former Microsoft Intellectual Property Lawyer
“We have information just broke a story that they hired a new IP, no, sorry, OpenAI hired a new IP lawyer who used to work in Microsoft, so go figure that one out.”
Jessica Lessin Jul 31, 2023 ▶ 50:04 #7: Elon's X game and RIP seed investing · More or Less Podcast
Assertion Supported
Dave Morin: Backchannel reports show AI chatbot engagement is down significantly
“There was a report today that the chat GPT usage or engagement is down quite a bit, which we've been hearing in the back channels, not just about GPT, but many of the other AI chatbots.”
Dave Morin Jul 7, 2023 ▶ 38:40 #5: Twitter Won't Die! Long Live Threads! · More or Less Podcast
Assertion Supported
Morin: OpenAI hired Charles Porch from Instagram to court creators
“Charles was hired at OpenAI from Instagram to like help build creator sort of love for OpenAI products, ChatGPT.”
Brit Morin Aug 7, 2026 ▶ 37:42 Jeff Dean Leaves Google, Airtable Sells, and the Bag-Securing Era · More or Less Podcast
Assertion Supported
Sam Altman and Greg Brockman attended jury selection in Elon Musk trial
“Sam Altman and Greg Brockman attended jury selection. Highly unusual. No one ever attends jury selection.”
Jessica Lessin May 1, 2026 ▶ 6:34 Elon Musk vs OpenAI Trial, Google Cloud Surge, Meta’s Blocked Acquisition, Anthropic Winning · More or Less Podcast
Assertion Supported
Morin: ChatGPT launched group chats in select international markets
“ChatGPT launched group chats in a bunch of obscure countries.”
Dave Morin Nov 21, 2025 ▶ 17:55 Google Just Won AI, TikTok’s “Self-Control Badges”, ChatGPT Enters Group Chats · More or Less Podcast
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