The Ledger

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why aren't all 661 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 58 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

Opinion
Kiela: Believing open-source AI can match OpenAI is incredibly naive
“I would like it to be true that with open source, we could just keep up with all of that. But I think that's just incredibly naive. Open AI has this very deep understanding of how people want to use language models. Basically nobody else has, and they have thi…”
Douwe Kiela Nov 24, 2023 ▶ 7:57 The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Seibert: On-device Apple LLMs could make OpenAI obsolete within five years
“I bet Apple can and will. And so if you project forward five years, if they get to the point where they can run a sufficiently large LLM on your iPhone, then OpenAI is out of the picture. You don't even need to hit their servers. It's just on your phone.”
Jeff Seibert Nov 22, 2023 ▶ 29:40 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Traynor: OpenAI will never solve end-to-end enterprise user workflows
“And the thick wrapper is, is like when you've actually solved the user's problem end to end fully in a way that OpenAI never will, you know.”
Des Traynor Nov 15, 2023 ▶ 11:45 Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings
Opinion
Traynor: VC capital in AI startups mostly passes straight to OpenAI
“Giving a dollar to a startup is just a lossy way of giving it to OpenAI or Anthropic or whoever, because, you know, that's who they're basically taking it and shining it up and handing it onto.”
Des Traynor Nov 15, 2023 ▶ 27:03 Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings
Opinion
Douwe Kiela: OpenAI and Anthropic are the Lycos and AltaVista of AI
“So if all the stars align, then OpenAI and Anthropic and all of these places, they had this great first generation technology. So they're kind of like the Lycos and Alta Vista of search engines. And the technology we have is more like PageRank. And that would …”
Douwe Kiela Jun 30, 2023 ▶ 53:20 Douwe Kiela: Why Data Size Matters More Than Model Size; Why Open Source Isn't Going to Win | E1032 · 20VC with Harry Stebbings
Opinion
Douwe Kiela: The leaked 'no AI moat' Google memo is completely wrong
“I think in terms of data modes and maybe you, you've seen this come by actually, there was this Google memo from an internal Google employee who had written that open AI and Google have no mode. I think for me as a AI researcher, when I read that memo, I was l…”
Douwe Kiela Jun 30, 2023 ▶ 23:45 Douwe Kiela: Why Data Size Matters More Than Model Size; Why Open Source Isn't Going to Win | E1032 · 20VC with Harry Stebbings
Opinion
Mostaque: OpenAI prioritizes building utopian AGI over a commercial business
“No, they're building an AGI to turn the world into utopia. It's written in their path to AGI thing, that they think this can basically bring about utopia.”
Emad Mostaque May 17, 2023 ▶ 21:20 Emad Mostaque: These 5 Companies Will Win the AI War; Why We Need National Data Sets | E1015 · 20VC with Harry Stebbings
Insight
Greze: AI wrappers face broken economics paying suppliers 70% margins to compete
“And the problem with the frontier is, I have zero pricing power at the frontier. And I mean, I think this is what happened to Cursor, right, at the end. It's like, you can have huge market share and customers love you and everything, but if you're paying your …”
Jean-Denis Greze Sep 7, 2026 ▶ 52:14 Town vs Instinct vs GrokBot | Why the AI Assistant Market Is Not a Bubble
Opinion
Reyes: OpenAI and Anthropic face existential risk from data center debt
“If you're open AI or you're anthropic, the hundreds of billions in free cash flow that you need in order to pay back the debt that you're taking on in order to accommodate these data center build outs in order to get the next big training run, it's totally exi…”
Eno Reyes Aug 29, 2026 ▶ 52:54 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Prediction Not checkable as stated
O'Driscoll: Consumer AI Could Reach Half Google's Size in a Decade
“I could totally see a business, you know, plus or minus, you know, 50% to the same size as the Google consumer business, maybe over the next decade.”
Rory O'Driscoll Aug 27, 2026 ▶ 40:42 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Prediction Not checkable as stated
O'Driscoll: Competing at the AI frontier is almost impossible for new entrants
“The lesson is, it's almost impossible to compete now at the frontier. And by the way, that has positive implications for OpenAI and Entropic, we should talk about in a second. So the negative lesson for everyone else is it is almost the next smartest people wh…”
Rory O'Driscoll Aug 27, 2026 ▶ 4:01 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Assertion Not checkable as stated
O'Driscoll: Anthropic and OpenAI exist only due to hyperscaler funding
“The only people capable of financing a state-of-the-art frontier model in the United States of America has been the hyperscalers themselves. The only reason Entropic and OpenAI exist is because Microsoft, Google, and Amazon gave them enough money to play becau…”
Rory O'Driscoll Aug 27, 2026 ▶ 10:06 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
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
Opinion
Lemkin: Selling subsidized consumer AI tokens is history's worst business model
“It's a crappy business that consumers selling 10,000 dollars worth of tokens for 200 dollars is one of the worst business models of our lifetimes, right? If that was the only business, these guys would be dead in the water. It's a pretty bad business.”
Jason Lemkin Aug 27, 2026 ▶ 40:03 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Prediction Open · timeframe Aug 2029
Murdock: Anthropic will go public before OpenAI
“It appears like Anthropic.”
Jerry Murdock Aug 22, 2026 ▶ 59:33 The AI Bubble WILL Burst | Should we be fearful of Chinese Open-Source | Jerry Murdock
Opinion
Murdock: Mega rounds for Anthropic and OpenAI might actually have been cheap
“And I would argue that it looks like anthropic and open AI, those crazy mega rounds, you know, at a hundred billion, a hundred and fifty billion might actually have been cheap.”
Jerry Murdock Aug 22, 2026 ▶ 32:43 The AI Bubble WILL Burst | Should we be fearful of Chinese Open-Source | Jerry Murdock
Prediction Not checkable as stated
Murdock: Frontier models will not be cannibalized in the short term
“We're going to absolutely see this thing that, you know, Prohibits the cannibalization of frontier models, at least in the short term.”
Jerry Murdock Aug 22, 2026 ▶ 17:37 The AI Bubble WILL Burst | Should we be fearful of Chinese Open-Source | Jerry Murdock
Opinion
O'Driscoll: Anthropic Holds Far Better IPO Timing Position Than OpenAI
“I think it's a far more attractive strategic position to be going out as Entropic in the fall with a, we've been profitable, okay, we're unprofitable again, but we're the winner in the enterprise, then going out next year where maybe the growth rates have star…”
Rory O'Driscoll Aug 20, 2026 ▶ 43:09 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
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
Prediction Open · timeframe Aug 2031
Stebbings: OpenAI and Anthropic Will Reach $1 Trillion to $2 Trillion Valuations
“Both will be trillion dollar plus, potentially close to two trillion.”
Harry Stebbings Aug 7, 2026 ▶ 1:03:43 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Prediction Not checkable as stated
Frankel: OpenAI, Anthropic, and SpaceX Are Today's Metas and Googles
“And I think in, you know, OpenAI and Anthropic and SpaceX, we're seeing that already. Like these are the Metas and the Googles of our era, highly likely.”
David Frankel Aug 7, 2026 ▶ 20:24 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Prediction Not checkable as stated
Frankel: OpenAI and Anthropic Will Eventually Be Disrupted by Chinese Competitors
“That anthropic and open AI are going to be disrupted. It's like unequivocal. Like our whole careers are about disruption. Those platforms never, ever stay forever. Where is it going to come from? Excellent chance it comes from China. It's coming.”
David Frankel Aug 7, 2026 ▶ 1:15:18 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Prediction Not checkable as stated
Stebbings: Mega venture platforms will achieve venture returns via massive outcomes
“I think with the outcome expansion that we've seen, cursor at sixty billion trillion dollar companies in a matter of years with OpenAI and Anthropic, you will see Venture returns with mega platform sizes.”
Harry Stebbings Aug 7, 2026 ▶ 37:45 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Assertion Not checkable as stated
O'Driscoll: OpenAI and Anthropic drive 70% of Google and AWS compute backlogs
“In other words, because they're 70% of the Google Compute backlog, the 70% of the Amazon backlog.”
Rory O'Driscoll Aug 5, 2026 ▶ 46:44 Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
Opinion
Arora: Foundation models will not disrupt Palo Alto Networks' perimeter security
“So when people tell me, oh, OpenAI is going to eat my lunch, or Mythos is going to eat my lunch, guess what? There are no perimeter security scenario, which means I still need to block the bad guy. They need to be the ingredient in my product. They're not goin…”
Nikesh Arora Aug 5, 2026 ▶ 31:26 Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
Prediction Open · timeframe Aug 2031
Angelopoulos: Nvidia is probably leading the race to a $10T valuation
“I think it's hard to say not NVIDIA. I think NVIDIA is probably in the lead there.”
Anastasios Angelopoulos Aug 2, 2026 ▶ 1:02:53 Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
Prediction Not checkable as stated
Angelopoulos: Two-thirds of 75 AI neo-labs will fail or be acqui-hired
“There's at least 75 Neolabs. And For sure, like two thirds of those are going to be worth nothing or like they're going to be bought out for parts, right? That's going to be like an aqua hire.”
Anastasios Angelopoulos Aug 2, 2026 ▶ 39:16 Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
Insight
Park: Simile Optimizes for Human Biases Over Super-Rationality
“So the way we see it is if you look at large length model companies today, fundamentally the task they have at hand is to create super rational, intelligent machines that are good at coding, that are good at natural sciences and mathematics. Similarly doesn't …”
Joon Sung Park Jul 31, 2026 ▶ 7:09 The AI Company Simulating the Entire Economy | Simile Co-founder & CEO, Joon Sung Park
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
Opinion
O'Driscoll: OpenAI and Anthropic 2026-2027 Growth Is Key Metric for AI Market
“Going back to this first sentence, the only thing that matters is the open AI and anthropic growth rate in 26 and 27.”
Rory O'Driscoll Jul 23, 2026 ▶ 1:26:53 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Assertion Not checkable as stated
O'Driscoll: OpenAI and Anthropic training data spend exceeds non-Cursor AI app revenues
“There's probably more money being spent on training data for the foundation models, you know, the Mercosurge and that, than pretty much any app company outside of Cursor. In fact, probably the sum of all the apps companies outside of Cursor, right, you know, a…”
Rory O'Driscoll Jul 23, 2026 ▶ 38:16 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Prediction Open · timeframe Jul 2031
AI Labs Will Not Compete In Regulated Complex Industries
“I think things that have some, like, regulation around them, and are, like, complex industries, yes, they're gonna see the advantages of the models, but they're not gonna see competition from Anthropik or OpenAI.”
Fred Turner Jul 18, 2026 ▶ 1:11:31 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
Prediction Open · timeframe Jul 2029
Lemkin: OpenAI will likely cancel or pause its hardware project
“Listen, if I had to breathe the tea leaves, hardware is probably on the bubble. This was one of Sam's initiatives that made sense when everything was working and OpenAI had an unassailable lead over, over its competitors, right? Now everything's, you know, we …”
Jason Lemkin Jul 16, 2026 ▶ 8:01 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Insight
O'Driscoll: Economic value from AI coding dwarfs all other LLM applications
“The main thing here is that LLMs are really amazing at code, and the amount of economic value that can be created from that dwells to everything else, right?”
Rory O'Driscoll Jul 16, 2026 ▶ 9:14 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lemkin: Nvidia would build custom chips for OpenAI if requested
“The only thing that makes zero sense to me is the argument that, hey, at OpenAI, we need to build our own our own chips because we have very specialized needs that NVIDIA can't meet. I have a little bit of experience in the semiconductor industry. If you're dr…”
Jason Lemkin Jul 9, 2026 ▶ 49:08 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
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
Prediction Open · timeframe Jul 2027
O'Driscoll: AI capex spending will be stopped by demand, not supply
“This isn't, this spending isn't going to stop because the supply side says stop. Facebook aren't going to say stop. Google isn't going to say stop. Microsoft isn't going to say stop. Really, it boils down to the demand side. As long as, and enterprise customer…”
Rory O'Driscoll Jul 9, 2026 ▶ 41:39 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Prediction Not checkable as stated
OpenAI and Anthropic IPO Performance Hinges on SpaceX
“I think if SpaceX performs well, the OpenAI Anthropic IPOs will also go very well. I think if SpaceX performs poorly, then those are going to have a hard time.”
Paul Erlang Jun 27, 2026 ▶ 53:04 How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI and Anthropic found the top consumer tech market in 20 years
“OpenAI and Anthropic have discovered the single best tech market in the, in terms of consumer demand in the last 20 years, and they should put all their effort into meeting that demand, right?”
Rory O'Driscoll Jun 25, 2026 ▶ 1:20:47 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Opinion
SpaceX is a unique N-of-1 company compared to OpenAI and Anthropic
“SpaceX. Why? It's an N of one company. Like, Anthropic and OpenAI can claim they do whatever each other does. But SpaceX is the only company building space infrastructure for connectivity.”
Aravind Srinivas Jun 15, 2026 ▶ 1:25:50 Perplexity CEO: Micron Will Be More Valuable Than Meta & How Export Controls Helped Not Hurt China · 20VC with Harry Stebbings
Insight
GPU cloud providers depend heavily on competitive open-source AI models
“If open source models stopped to actually be good, where the gap between them, the frontier is like more than 12 months or like 15 months, 18 months, then I don't think these companies really have a business model because they're not going to be able to host. …”
Aravind Srinivas Jun 15, 2026 ▶ 44:25 Perplexity CEO: Micron Will Be More Valuable Than Meta & How Export Controls Helped Not Hurt China · 20VC with Harry Stebbings
Prediction Not checkable as stated
Advertising will fail to take off in AI chat interfaces
“So I, I'm bearish on advertising to really take off in the chat interface. I, I'm happy to be proven wrong there, but I'm bearish on that.”
Aravind Srinivas Jun 15, 2026 ▶ 11:38 Perplexity CEO: Micron Will Be More Valuable Than Meta & How Export Controls Helped Not Hurt China · 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
Insight
O'Driscoll: Consumer AI will be tougher for OpenAI than enterprise
“I think actually, you know, the consumer space is going to be a tougher space for open. The enterprise space has really been validated. Cause an enterprise is all about automation efficiency and a consumer space. It's about experiences. Apple's well-placed to …”
Rory O'Driscoll Jun 11, 2026 ▶ 24:13 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Opinion
O'Driscoll: Partnering with OpenAI is no longer a sufficient AI strategy
“This was the end of the period where you could Fool yourself even slightly that your plan for your plan for AI is to partner with open AI. That's just not the answer anymore.”
Rory O'Driscoll Jun 11, 2026 ▶ 1:11:44 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Prediction Not checkable as stated
Majority of AI Inference Will Run on Open-Source or Distilled Models
“I think that majority of inference in five years is going to be using a open source or custom fine-tuned or distilled model, not using a frontier model.”
Brendan Foody Jun 1, 2026 ▶ 50:21 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 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
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