The Ledger

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why aren't all 112 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Prediction Held up
O'Driscoll: OpenAI misses next year's revenue target by 40% if growth matches Google
“If all OpenAI is, Is just as good as Google, then it's going to miss its number next year by about 40%.”
Rory O'Driscoll Jun 5, 2025 ▶ 47:06 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Assertion Supported
Mollick: OpenAI's $3B revenue run rate is largely an accident
“I mean, they're incidentally making three billion dollar run rate this year, I think by like just accident, but there isn't like a, there isn't really a product there right now.”
Ethan Mollick Jul 31, 2024 ▶ 24:14 Ethan Mollick: Why OpenAl Abandons Products, The Biggest Opportunities They Have Not Taken | E1184 · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: OpenAI is lobbying in Washington for AI regulation alongside Anthropic
“They're signing this publicly while at the same time lobbying in Washington right alongside Anthropic for a regulatory process.”
Rory O'Driscoll Jul 29, 2026 ▶ 5:47 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Assertion Supported
Lemkin: OpenAI and Anthropic Lied About Books and YouTube Training Data
“Open AI, an anthropic, Kind of lied about the books, and they definitely lied about training on YouTube”
Jason Lemkin Jul 9, 2026 ▶ 31:42 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Assertion Supported
Lemkin: OpenAI and Anthropic yield 40-70% gross margins on enterprise inference
“They have an enterprise base, which is, it has, you know, between 40 and 70% in, you know, gross margin just on inference.”
Jason Lemkin Jun 25, 2026 ▶ 36:08 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Altman Offered $2M in OpenAI Tokens to Every YC Startup
“Sam Altman just offered two million dollars In open AI tokens to every YC startup in the current batch in exchange for equity.”
Harry Stebbings May 21, 2026 ▶ 1:02:36 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Anthropic revenue surged to 64% of OpenAI's in 14 months
“Anthropic said it's hundred K customers are up seven X in the last year. So there's not enough time to steal deals. Having said that, going from five percent of OpenAI's revenue to 64% in 14 months, that is stealing budget.”
Jason Lemkin Feb 19, 2026 ▶ 10:56 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Sam Altman receives zero equity in OpenAI's corporate restructuring
“They're a little interesting, but the craziest thing in this deal, because it's unprecedented, I think in our lifetimes is OpenAI said that Sam Altman will still have no shares in the combined entity.”
Jason Lemkin Oct 30, 2025 ▶ 3:44 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Prediction Held up
Taneja: Anthropic's enterprise business will be bigger than OpenAI's
“I think their enterprise business I'd argue will be bigger than OpenAI if it already isn't already not having spent that much.”
Hemant Taneja Sep 22, 2025 ▶ 40:38 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
Assertion Supported
Lemkin: OpenAI Stole YouTube Videos to Train AI Models
“This isn't even stealing YouTube videos like OpenAI did.”
Jason Lemkin Sep 11, 2025 ▶ 45:06 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Oracle closed a $30 billion annual deal with OpenAI
“Oracle just closed a thirty billion dollar a year deal with open AI, right? An extra thirty billion.”
Jason Lemkin Jul 3, 2025 ▶ 58:55 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Assertion Supported
Lemkin: OpenAI has a 67% two-year employee retention rate
“67% retention rate employees after two years.”
Jason Lemkin May 29, 2025 ▶ 13:48 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
Assertion Supported
Stebbings: OpenAI CFO told employees the company will IPO in 2027
“CFO Sarah Fryer told employees at OpenAI, we will be a public company in twenty-twenty-seven.”
Harry Stebbings Aug 27, 2026 ▶ 25:53 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Assertion Supported
Datadog's largest customer, OpenAI, slashed its $150 million software spend
“Datadog's story was just, everything's amazing, but our biggest customer, and everybody knows it's OpenAI and know what it says, right, is suddenly realized they maybe don't need to spend a hundred and fifty million dollars and they're spending less.”
Rory O'Driscoll Aug 12, 2026 ▶ 1:21:30 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Assertion Supported
O'Driscoll: Hugging Face defended against OpenAI probe using Chinese models
“The Chinese open source, open rate models were available, and I think they use Kimi or Kuan or one of the newest models to help them figure out what happened, right? So they were able to defend themselves using an open source model, and then they do this blog …”
Rory O'Driscoll Jul 29, 2026 ▶ 9:28 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Assertion Supported
O'Driscoll: Sandboxed OpenAI test model escaped to query Hugging Face
“OpenAI was training a next generation model and managing cyber and discovering and checking out cyber vulnerabilities. They had sandboxed it in such that the only access externally it has was to one website to just to get kind of Patch of information updates, …”
Rory O'Driscoll Jul 29, 2026 ▶ 7:47 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Assertion Supported
O'Driscoll: OpenAI reached $12B and Anthropic $4B in GAAP revenue
“The rate at which, you know, OpenAI and Tropic got to four and twelve billion, respectively, other way around, sorry, 12 and four billion, respectively, in GAAP revenue, never before seen, right?”
Rory O'Driscoll Jul 9, 2026 ▶ 1:14:18 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Assertion Supported
Perplexity differentiates by orchestrating across competing AI models
“And the way we differentiate ourselves at perplexity Is we don't just orchestrate across tools and files and connectors. We also orchestrate across models. That is the differentiation that Anthropic and OpenAI cannot claim”
Aravind Srinivas Jun 15, 2026 ▶ 14:07 Perplexity CEO: Micron Will Be More Valuable Than Meta & How Export Controls Helped Not Hurt China · 20VC with Harry Stebbings
Assertion Supported
Foody: Mercor did not lose OpenAI as a customer after hack
“False. Our relationship with OpenAI is stronger than ever.”
Brendan Foody Jun 1, 2026 ▶ 7:38 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: AI labs will throttle subscriptions and hike prices for compute
“You're going to see some compute rationally, people are going to start allocating tokens to the highest, effectively the highest bidder. You're going to see a lot of throttling, like, you're going to see these plans, like, that's why they shot Sora. You're goi…”
Rory O'Driscoll Apr 16, 2026 ▶ 54:11 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Anthropic reports gross AWS revenue; OpenAI reports net Microsoft revenue
“There was this kind of whole meme of OpenAI reports net on their partner revenue and Entropic reports gross. And what they're saying there is if OpenAI sells through Microsoft and Microsoft takes some money off the top, OpenAI only reports the net amount. If A…”
Rory O’Driscoll Apr 2, 2026 ▶ 30:31 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Anthropic reaches $19B ARR while OpenAI hits $25B ARR
“Well, to be fair about Entropic and OpenAI, they have a very clear and sensible way they define ARR. What they say is they take the last, the average of the last four weeks to smooth out times to 13, because there were 1304 week periods in a year, which is mor…”
Rory O’Driscoll Apr 2, 2026 ▶ 29:31 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Thrive Capital specifically declined Anthropic investment due to OpenAI stake
“They actually specifically, unlike some of the other funds that have invested in both, they've Specifically our fund that said, no, we backed open AI. We're not going to back on tropics.”
Rory O'Driscoll Feb 19, 2026 ▶ 1:12:33 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Assertion Supported
Acharya: OpenAI reached $20B top line by tripling capacity and matching demand
“Look, this is not my area of focus or expertise, but one, you look at OpenAI's recent investment announcement, sorry, which is that there are twenty billion of top line. And the way that they got there is they three X capacity and they three X top line. So eve…”
Anish Acharya Feb 9, 2026 ▶ 28:38 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Prediction Held up
Lemkin: OpenAI, Anthropic, and xAI will rush IPOs due to capital pressure
“What all three of those say to me is there's no matter, there's subtle pressure around access to capital. Like they've all got to have an IPO strategy sooner than they'd hoped because Data center, because XAI needs capital, because Anthropic is even worried ab…”
Jason Lemkin Feb 5, 2026 ▶ 7:36 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Assertion Supported
O'Driscoll: NVIDIA issued a document committing up to $100B to OpenAI
“There's a piece of paper. With the NVIDIA logo on it that said we'll do up to a hundred billion, and they put it out there, and now they're like, where's my hundred billion?”
Rory O'Driscoll Feb 5, 2026 ▶ 1:07:49 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Assertion Supported
O'Driscoll: Musk Seeks $70B to $130B in OpenAI Equity Damages
“The damages claim is 70 to a hundred and thirty billion dollars, which would come in the form of extra shares of open AI to Elon and everyone else would have to take the dilution.”
Rory O'Driscoll Jan 22, 2026 ▶ 28:19 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Anthropic has closed its valuation gap with OpenAI to 2:1
“The way I keep score is the relative value of Amtropic to open AI is kind of the ratio of let's call it management success from over the last three years. And the truth is it's gone from, you know, 10 or eight to, you know, 10 plus to one to much more converge…”
Rory O'Driscoll Jan 15, 2026 ▶ 18:15 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Assertion Supported
Lemkin: OpenAI retains only around 60% of its AI researchers
“They still only have like 60 something percent retention in researchers at OpenAI.”
Jason Lemkin Jan 8, 2026 ▶ 42:53 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Assertion Supported
Calacanis: ChatGPT monthly user growth has slowed to single digits
“If you look at the numbers, the growth is down to single digits. Like, it's just, it is empirically true on any source. The growth is down to single digits on monthly growth.”
Jason Lemkin Dec 18, 2025 ▶ 16:35 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: OpenAI Is in Code Red Mode, Delaying Expansion
“That's the OpenAI story from a day ago, and the OpenAI story today is almost the exact opposite. It's the code red, focus on the core, and almost like a statement that says, all the other things we've been doing, we ain't doing them now. We're just going to be…”
Rory O'Driscoll Dec 4, 2025 ▶ 1:20 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Sam Altman Says OpenAI Will Hit $20B ARR This Year
“Altman says OpenAI is going to hit twenty billion ARR this year.”
Harry Stebbings Nov 13, 2025 ▶ 13:32 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Assertion Supported
Randle: OpenAI has the fastest growth trajectory in tech history
“What ended up mattering is that it, you know, it's had the strongest and highest growth trajectory Of any technology company in history.”
Everett Randle Nov 10, 2025 ▶ 13:04 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Supported
Randle: Benchmark's top fund investments outperform all post-ChatGPT OpenAI rounds
“Out of our last fund, our five best investments in that last fund today held at LRP last round price are about a 60 X. We have two 30 X's and we have two 20 X's. Since ChatGPT was released, there isn't an open AI round that touches That return multiple and tha…”
Everett Randle Nov 10, 2025 ▶ 34:15 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Prediction Held up
Zhang: Valuation gap between OpenAI and Anthropic will shrink over time
“I don't think that long-term necessarily we'll always see a five X difference between open and anthropic. So I guess, yeah, maybe, maybe if the question is more like, what is spread trade? I think like that, that multiple will shrink. Over time.”
Jesse Zhang Sep 19, 2025 ▶ 50:43 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
Assertion Supported
ElevenLabs speech-to-text beats OpenAI and Gemini on benchmarks
“Then speech to text is beating open AI, Gemini on benchmarks.”
Mati Staniszewski Sep 8, 2025 ▶ 14:06 ElevenLabs CEO/Co-Founder, Mati Staniszewski:The Untold Story of Europe’s Fastest Growing AI Startup · 20VC with Harry Stebbings
Prediction Held up
Deeter: Top three LLM companies will raise $100B in six months
“I think the numbers right now, the top three LLMs, if you include you know, Anthropoc, OpenAI, and X in there, ah, are gonna raise a hundred billion dollars in this six month period”
Byron Deeter Aug 25, 2025 ▶ 8:49 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Supported
Lemkin: OpenAI Pays Datadog $240 Million Annually
“So apparently OpenAI pays Datadog two hundred and forty million a year.”
Jason Lemkin Aug 14, 2025 ▶ 41:38 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: ChatGPT generates 70% to 80% of OpenAI's revenue
“ChatGPT, which is, you know, 70, 80% of the revenue dollars when they shipped, they didn't even think it was a major release.”
Rory O'Driscoll Aug 14, 2025 ▶ 6:21 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: OpenAI and Anthropic can become $500B-$1T companies without AGI
“I think both of these companies can be plus or minus, you know, half a trillion to trillion dollar companies.”
Rory O'Driscoll Aug 14, 2025 ▶ 13:08 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Assertion Supported
OpenAI Is Burning $5B to $10B Per Year
“They're burning Five to ten billion dollars a year, right?”
Miles Dieffenbach Aug 4, 2025 ▶ 1:14:36 Miles Dieffenbach: Inside Carnegie Mellon’s $4BN Endowment & The Math Behind DPI, TVPI, Illiquidity · 20VC with Harry Stebbings
Prediction Held up
Stebbings: OpenAI will top $800B valuation driven by new products
“I'll take the contrarian on you there and say that because of GPT-V and because of Kodak's being two very significant breakthroughs, they'll have enough, plus Johnny Ive coming out with something, a first product, the three combined will be enough to get enoug…”
Harry Stebbings Jul 31, 2025 ▶ 1:19:30 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: xAI will fail to displace ChatGPT's dominant consumer mindshare
“The market's already been taken and maybe it gets some share of it, but I don't think, yeah, I don't think you can build as big a thing. I don't think you can build, I don't think you can displace ChatGPT at scale in the minds of the consumer, which is 80, 90%…”
Rory O'Driscoll Jul 17, 2025 ▶ 1:09:50 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
Assertion Supported
Lemkin: OpenAI's stock compensation reached $4.4B, exceeding revenue
“Last year, according to the information open AI had 4.4 billion in stock compensation. That was 119% of its gap revenue.”
Jason Lemkin Jul 10, 2025 ▶ 21:15 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: Coatue's Retail VC Fund Will Sell by Offering AI Access
“Do I think it'll work and raise capital? Probably it will because the facts are there. The other The other PE vehicles have worked. And then let's get real. You know, at the end, it'll be packaged with some version of this is the only way you can get access to…”
Rory O'Driscoll May 15, 2025 ▶ 26:06 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Prediction Held up
Moore: SpaceX, OpenAI, and Anthropic will reach multi-trillion dollar outcomes
“We're talking about going from talking about 30 to fifty billion dollar outcomes to multi-trillion dollar outcomes in the form of SpaceX or OpenAI or Anthropic.”
Bucky Moore May 5, 2025 ▶ 2:27 Bucky Moore @ Lightspeed Venture Partners: Why You Cannot Do VC If You Do Not Do Pre-Seed · 20VC with Harry Stebbings
Assertion Supported
Moore: OpenAI blocked investors in enterprise search startup Glean
“OpenAI famously saying, hey, if you're an investor in Glean, you don't get to be an investor in OpenAI, which would foreshadow they plan to play in that space.”
Bucky Moore May 5, 2025 ▶ 7:43 Bucky Moore @ Lightspeed Venture Partners: Why You Cannot Do VC If You Do Not Do Pre-Seed · 20VC with Harry Stebbings
Assertion Supported
Ross: DeepSeek developed its models by distilling OpenAI
“They distilled the OpenAI model.”
Jonathan Ross Feb 17, 2025 ▶ 57:47 Jonathan Ross, Founder & CEO @ Groq: NVIDIA vs Groq - The Future of Training vs Inference | E1260 · 20VC with Harry Stebbings
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