The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

clear all ✕

why aren't all 443 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 42 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
Ross: Anthropic should open-source older models to counter Chinese AI adoption
“I think that Anthropic should be open sourcing their previous generation in order to get people using them instead of the Chinese models.”
Jonathan Ross Sep 29, 2025 ▶ 33:32 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
Assertion Not checkable as stated
O'Driscoll: Anthropic Could Raise $10B Tomorrow If It Wanted
“My understanding is they were beating people off with a stick on the recent on Tropic round. And if they decided they want another ten billion, it'll be there tomorrow morning. So it's not capital constrained.”
Rory O'Driscoll Sep 25, 2025 ▶ 6:13 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Opinion
Taneja: Microsoft and OpenAI's partnership is fracturing over colliding ambitions
“Is that an enduring investment? No, obviously now they've gone at odds with each other because there's an ambition that collides between the two companies and so they want to have more choice. They want to have anthropic at the table as well.”
Hemant Taneja Sep 22, 2025 ▶ 39:27 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
Prediction Not checkable as stated
Taneja: Anthropic investors will see better return multiples than OpenAI's
“And that's why the investors there will probably end up doing on a multiple basis better than again, you know, in a world of like what's durable, what's not like they're trending to be, maybe they'll do better. In their MOI than the early investors would in op…”
Hemant Taneja Sep 22, 2025 ▶ 41:43 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
Prediction Held up
Taneja: Anthropic could be worth $500B by next year
“So that's half a trillion dollar company, like by the end of next year. I'm not saying that's what it's going to be, but if they hit their numbers, I don't see why that won't happen. Just from, I'm just saying public market comps, like that's what those things…”
Hemant Taneja Sep 22, 2025 ▶ 43:26 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
Assertion Supported
Taneja: Anthropic raised at ~20x ARR versus 50-100x for AI peers
“Anthropic this round probably was the cheapest round that got done this year on a multiple spaces. Which company was raising capital at, you know, at 20 times ARR? They're all raising capital at 50 to a hundred times ARR.”
Hemant Taneja Sep 22, 2025 ▶ 35:18 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 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 Contradicted
Lemkin: Microsoft shifting default model choice to Anthropic across several products
“Microsoft I think today said they're moving not just parts of office to Anthropic, but that it is the default choice for several other products and that Microsoft today said several months ago, they told their teams to start using cloud code several months ago…”
Jason Lemkin Sep 18, 2025 ▶ 44:01 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Assertion Not checkable as stated
Stebbings: Decacorn CEOs spend aggressively on AI but switch easily
“The only interesting take I'll take is that I interview, honestly, three to four Dacacorn CEOs every week, and on this topic, two interesting elements, completely price insensitive as to how much they spend on Anthropic, and Claude Code in particular. I was th…”
Harry Stebbings Sep 18, 2025 ▶ 1:03:43 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI and Anthropic No Longer Need Microsoft or Amazon
“In both these cases, the small company won. They got the money, they got the critical mass, they got the credibility, and now they've pulled away. And neither on top of now open AI needs Microsoft or Amazon at this point. They don't need them for money. They d…”
Rory O’Driscoll Sep 18, 2025 ▶ 49:41 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Anthropic Sourced AI Book Training Datasets Directly from Pirate Sites
“They downloaded this from pirate websites. Okay. This wasn't cutting a little bit of a corner. Okay. This wasn't claiming something that wasn't quite open source was, This is literally, guys, we got to get this rocket ship going. I need a trillion books. I'm g…”
Jason Lemkin Sep 11, 2025 ▶ 44:45 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Assertion Not checkable as stated
O'Driscoll: Anthropic's valuation is 8-9x next year's revenue if growth persists
“The stunning thing with this growth rate, if it persists, big underline, is you're only buying in at eight to nine times next year's revenues if the growth lasts.”
Rory O'Driscoll Sep 4, 2025 ▶ 2:45 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Lemkin: ICONIQ used Statsig acquisition as backdoor to invest in OpenAI
“Iconic rolls over a hundred million into open AI. They're not allowed to invest because they led the anthropic round. Right. So this is the only way they can put nine figures into it because they're soft band or hard band from the round.”
Jason Lemkin Sep 4, 2025 ▶ 16:11 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Anthropic grew revenue from $100M to $1B in 2024
“They went from a hundred to a billion last year.”
Rory O'Driscoll Sep 4, 2025 ▶ 32:43 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 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
Opinion
Deeter: Bessemer invested in Anthropic believing it could be a 30x return
“You know, 3.8 X will keep you in business for a long time, but the reason to do it is because you believe it could be a 30 X. And that's the basis of our anthropic investment is we believe that it is a generational company.”
Byron Deeter Aug 25, 2025 ▶ 7:09 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Not checkable as stated
Deeter: Anthropic's revenue growth trajectory is unprecedented in tech history
“Like, when you actually see the anthropic numbers that he's now sharing, and like, this is real, and, you know, their path to billions and billions in revenue, and, you know, really compelling unit economics, I just, we have never seen this in the history of o…”
Byron Deeter Aug 25, 2025 ▶ 1:21:36 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Assertion Not checkable as stated
Deeter: Economics for Anthropic, Perplexity, and Canva Pencil Out
“And I assure you, one of the coolest things about the profile of anthropic and perplexity and Canvan, these businesses is the math actually pencils out.”
Byron Deeter Aug 25, 2025 ▶ 28:04 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Disclosure
Osika: Majority of Lovable's paid usage revenue goes to AI compute
“I don't give you the exact numbers, but if you look at the paid usage, it's majority, it's not everything.”
Anton Osika Aug 18, 2025 ▶ 9:40 Lovable CEO, Anton Osika: The State of Foundation Models, Grok vs OpenAI, and Replit vs Bolt · 20VC with Harry Stebbings
Opinion
Osika: Grok has better team morale and trajectory than OpenAI and Anthropic
“I think it's more the slope on the Grok team. They have, they're doing something which I respect a lot, which is to hire missionaries for the data curation part, and they call it AI tutoring. And they I think the morale is much, much better in that team than b…”
Anton Osika Aug 18, 2025 ▶ 1:05:37 Lovable CEO, Anton Osika: The State of Foundation Models, Grok vs OpenAI, and Replit vs Bolt · 20VC with Harry Stebbings
Prediction Not checkable as stated
Osika: OpenAI will be a bigger competitor to Lovable than Anthropic
“OpenAI is doing that better than Anthropic. So I see them as a more serious competitor in, in, in 12 months.”
Anton Osika Aug 18, 2025 ▶ 16:39 Lovable CEO, Anton Osika: The State of Foundation Models, Grok vs OpenAI, and Replit vs Bolt · 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
Opinion
O'Driscoll: Pure developer tools cannot support a $1T valuation
“I don't think you get to a month of a trillion dollars if you're just selling stuff to developers, which isn't to say I don't think you do extraordinarily well.”
Rory O'Driscoll Jul 31, 2025 ▶ 36:36 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
Opinion
Casado: Google's Gemini 2.5 Beats Anthropic On Price-Performance For Many Uses
“Gemini 2.5 is a great model. It's a great model. And if you actually look at it, you know, on the price performance, I would say in many use cases, the one that I actually use as my standard model, it's better than Anthropic.”
Martin Casado Jul 28, 2025 ▶ 7:30 a16z GP, Martin Casado: Anthropic vs OpenAI & Why Open Source is a National Security Risk with China · 20VC with Harry Stebbings
Prediction Open · timeframe Jul 2030
O'Driscoll: Anthropic will not cut off Cursor from model access
“I think it'd be very stupid of Entropic to just cut off a, probably the largest customer at the knees. And I, and the one thing, they're not stupid. So I don't think they will.”
Rory O'Driscoll Jul 24, 2025 ▶ 18:00 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Opinion
O'Driscoll prefers investing in Anthropic at $100B over OpenAI at $300B
“I think I do Anthropic at a hundred just from a back short-term momentum perspective.”
Rory O'Driscoll Jul 24, 2025 ▶ 23:02 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Prediction Open · timeframe Jul 2030
O'Driscoll: OpenAI and Anthropic are the only AI startups that will survive
“The clear three, the two people who are clearly going to be at the table as startups when this is done are OpenAI and Entropic. It, it's hard to imagine beyond that.”
Rory O'Driscoll Jul 24, 2025 ▶ 22:15 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
Prediction Not checkable as stated
Chen predicts future will feature multiple competing frontier AGI companies
“How I see a world where there actually will be multiple, multiple, Frontier AI companies, Frontier AGIs, just because every one of them will be able to go in a different direction. Like, you see it already, you see it today playing out already with the differe…”
Edwin Chen Jul 21, 2025 ▶ 1:02:57 Surge CEO & Co-Founder, Edwin Chen: Scaling to $1BN+ in Revenue with NO Funding · 20VC with Harry Stebbings
Assertion Supported
Wu: Anthropic has quadrupled its revenue since reaching a $60B valuation
“Well, Anthropic has quadrupled their revenue since they were valued at sixty billion, so it seems like a fair one to pick.”
Scott Wu Jul 18, 2025 ▶ 41:19 Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 20VC with Harry Stebbings
Prediction Open · timeframe Jul 2030
Wu: Private AI foundation labs will far exceed $500B aggregate valuation
“If you add all their valuations today, what is that? Like, 500 B, something like that? I think that's gonna go way up in the next five years.”
Scott Wu Jul 18, 2025 ▶ 40:27 Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale · 20VC with Harry Stebbings
Prediction Not checkable as stated
O'Driscoll: Meta won't build a major business selling LLaMA APIs
“It's not that they want to open source Lama and make money off it. They won't. It's not that they want to even have an API offering of Lama, something like, you know, a, an anthropic offering that just won't be big.”
Rory O'Driscoll Jun 26, 2025 ▶ 2:49 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Opinion
Offloading $1B of Anthropic stock in private markets is extremely difficult
“Today I think there's a handful of liquid private companies basically. They're quasi-liquid. But at scale. Small positions, yes. But try to go move a billion dollars of Anthropic.”
Larry Aschebrook Jun 16, 2025 ▶ 1:30:43 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Prediction Open · timeframe May 2032
O'Driscoll: Four or more venture exits will top $65B in 5-7 years
“If there's not four exits, Above sixty five billion in the next five or seven years, then the people who bought Stripe, SpaceX, Databricks, OpenAI and Antropic are screwed. So I don't think they're screwed. So I think there's going to be, this trend is going t…”
Rory O'Driscoll May 22, 2025 ▶ 31:41 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
Insight
Hacker: Opening an SF satellite office creates a talent drain to local giants
“It creates this internal funnel of your best employees moving from your HQ to Silicon Valley. Which by itself is not a problem. The problem is then they get recruited away by the whatever the hot Silicon Valley company is at the time. You know, like it could b…”
Severin Hacker May 19, 2025 ▶ 1:11:24 Duolingo Co-Founder, Severin Hacker: How AI Impacts the Future of Work and Education · 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
What-if
Stebbings: Anthropic and Cursor Venture Investments Would Have Saved FTX
“When you look at FTX, their positions in Anthropic and Cursor actually would have saved them if they had the time to prove that out and they hadn't done the commingling. That would have saved their financial performance with those two investments alone.”
Harry Stebbings May 15, 2025 ▶ 18:23 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Assertion Not checkable as stated
Stebbings: Anthropic's $4B round investors hold only 3.5x to 4x returns
“People who did Anthropic at four billion have got about a three and a half to four X when you combine the dilution and the employee stock payouts.”
Harry Stebbings May 5, 2025 ▶ 4:28 Bucky Moore @ Lightspeed Venture Partners: Why You Cannot Do VC If You Do Not Do Pre-Seed · 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 Not checkable as stated
O'Driscoll: Non-OpenAI foundation model startups have underperformed Anthropic
“If you fast forward three years, all the foundation model companies that weren't populated by people who were at OpenAI haven't done great, and Anthropic that was populated by people that came from OpenAI has done pretty well.”
Rory O'Driscoll Apr 17, 2025 ▶ 1:10:45 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Opinion
Nayak: Anthropic Is Surpassing OpenAI in Attracting Top AI Talent
“I would have said OpenAI maybe six months ago, but I think Anthropic is really starting to appeal to a lot more people.”
Aatish Nayak Apr 11, 2025 ▶ 1:00:45 20Product: How Scale AI and Harvey Build Product | Why PMs Are Wrong: They are not the CEOs of the Product | How to do Pre and Post Mortems Effectively and How to Nail PRDs | The Future of Product Management in a World of AI with Aatish Nayak
Opinion
Singlehurst: Baillie Gifford wouldn't buy OpenAI, Grok, or Anthropic currently
“I think at the moment I would say that I would buy none of them. And it's not because I have a particular, and it's not because I'm critical of those businesses. It's because I don't know what the answer is to enduring competitive advantage at the large langua…”
Peter Singlehurst Mar 19, 2025 ▶ 1:04:45 Peter Singlehurst: Lessons from Turning Down Stripe, Coinbase and Losing Money on Northvalt · 20VC with Harry Stebbings
Opinion
Biilmann: Bullish on Anthropic due to coding and programming superiority
“Anthropic definitely has really stood out in, in their ability to solve programming and coding style tasks in a way that I think is like I'm very bullish on Anthropic for that reason, because I think that's such a groundbreaking part of what makes LLMs multipl…”
Matt Biilmann Mar 14, 2025 ▶ 32:16 20Product: How to Design and Build Products in a World of Agents | Why AI Will Kill Many SaaS Products | What Products Will Thrive and Die in a World of 100M Developers with Matt Biilmann, Co-Founder and CEO @ Netlify
Opinion
Biilmann: Would buy Anthropic over OpenAI and Grok at current valuations
“I would probably go for Anthropic. It's a really interesting thing from the outside where a lot of their motivation started around these like safety concerns and like, how do we allow the models to not take over the world and so on. And I think after sort of a…”
Matt Biilmann Mar 14, 2025 ▶ 33:03 20Product: How to Design and Build Products in a World of Agents | Why AI Will Kill Many SaaS Products | What Products Will Thrive and Die in a World of 100M Developers with Matt Biilmann, Co-Founder and CEO @ Netlify
Assertion Partly supported
Osika: Anthropic's enterprise revenue has almost caught up to OpenAI's
“If you look at the enterprise revenue, like, Anthropik is almost caught up to open AI from nothing, from being absolutely dominated”
Anton Osika Mar 5, 2025 ▶ 37:57 Anton Osika, Co-Founder and CEO @ Lovable: Hitting 85% Day 30 Retention - Better than ChatGPT · 20VC with Harry Stebbings
Prediction Not checkable as stated
Krieger: Top AI models will require both human and synthetic data
“So I think it absolutely has to be a mix. And I think the best models will come from that combination of great, like for code it's, you know, being, having good foundational understanding of code and good examples, but then also being able to explore a really …”
Mike Krieger Mar 3, 2025 ▶ 14:20 Mike Krieger, Instagram CoFounder & Anthropic CPO: Where Will Value Be Created in an AI World?|E1265 · 20VC with Harry Stebbings
Insight
Krieger: Creating multi-step task environments is the main AI blocker
“Figuring out how we better either break that down into component parts, which is probably part of the story, but also think about it holistically is the biggest blocker to at least one slice of progress, which is how do models go from being extremely good at e…”
Mike Krieger Mar 3, 2025 ▶ 12:38 Mike Krieger, Instagram CoFounder & Anthropic CPO: Where Will Value Be Created in an AI World?|E1265 · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2028
Krieger: Anthropic is focusing on agentic tools, not building an IDE
“So when I think about the coding space and where we can play and add value, it really is on the agentic side. It's not on the ID side.”
Mike Krieger Mar 3, 2025 ▶ 43:04 Mike Krieger, Instagram CoFounder & Anthropic CPO: Where Will Value Be Created in an AI World?|E1265 · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2028
Krieger: Anthropic will build general-purpose software, not bespoke vertical AI
“We are going to be building things that are general purpose as a rule with maybe some specialization at the, like, user level, but not at the, I don't anticipate us building a lot of verticalized experiences that are, like, fairly bespoke to a given workflow o…”
Mike Krieger Mar 3, 2025 ▶ 38:51 Mike Krieger, Instagram CoFounder & Anthropic CPO: Where Will Value Be Created in an AI World?|E1265 · 20VC with Harry Stebbings
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.