The Ledger

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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
Randle: Frontier AI models can now autonomously execute cyber attacks
“Zooming out, I think the most important thing in all this Is that we step back from Anthropic and realize that the models are to place now, whether they're from Anthropic or elsewhere, where they can autonomously find and chain multiple vulnerabilities togethe…”
Everett Randle Jun 18, 2026 ▶ 37:06 Anthropic's Fable Banned by US Government | Wix & Adobe Hit All-Time Lows | Mistral Raising at $20BN · 20VC with Harry Stebbings
Assertion Supported
Anthropic lobbied heavily for US AI export controls
“And definitely like companies like Anthropic lobbied very hard for it.”
Aravind Srinivas Jun 15, 2026 ▶ 54:25 Perplexity CEO: Micron Will Be More Valuable Than Meta & How Export Controls Helped Not Hurt China · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: xAI Rented Colossus Cluster to Anthropic for $1.25B Monthly
“They've rented that to Entropic for 1.25 billion a month, right, with a, I think, a ninety-day cancellation clause on either side.”
Rory O'Driscoll May 28, 2026 ▶ 50:13 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
Assertion Supported
Peets: Anthropic offered sales reps $1.2M compensation packages
“Like if Anthropic, for example, when they were at their three 80 valuation, they were offering reps, call it a 1,000,002.”
Chad Peets May 23, 2026 ▶ 49:25 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Anthropic secondary market pricing has reached $1 trillion
“Every dollar wants its home in Anthropic right now, and it's caused secondary market prices to surge to a trillion dollars for Anthropic.”
Harry Stebbings Apr 23, 2026 ▶ 42:49 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Prediction Held up
Lemkin: US government will block Anthropic indefinitely regardless of court rulings
“The government's going to say you're either going to agree to this or we're going to freeze you out of the US economy. And it doesn't matter what a court says. Because they'll come up with another justification. There'll be another one. There'll be a different…”
Jason Lemkin Mar 12, 2026 ▶ 5:55 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Assertion Supported
Swisher: Anthropic reached $9B ARR while growing 800%
“If you look at Anthropic, right, publicly available numbers, nine billion of ARR growing 800%.”
Lucas Swisher Feb 23, 2026 ▶ 58:20 Insights from Coatue's Growth Investor Lucas Swisher · 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
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
O'Driscoll: Anthropic's burn dropped from $5B last year to $3B this year
“Seeing the, you know, the strong performance from Antropic in terms of top line growth, and then just looking at the burn, you know, five last year going to three this year.”
Rory O'Driscoll Jul 3, 2025 ▶ 23:00 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
Assertion Supported
Salesforce Agreed to Shift Its LLM Spending to Anthropic
“Dario is showing up because Mark agreed to move Salesforce agreed to move Their LLM spend to Anthropic.”
Jason Lemkin Sep 3, 2026 ▶ 56:14 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Assertion Supported
Angelopoulos: Most global AI inference spend remains on proprietary first-party APIs
“If you look at the whole space of all inference, most of it is still being consumed on first party APIs and on proprietary models. That's why anthropic revenue has been just a total hockey stick. It's not, you know, it's not like they're being completely canni…”
Anastasios Angelopoulos Aug 2, 2026 ▶ 5:44 Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
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
O'Driscoll: Anthropic Letter Tells Senate Chinese AI Firms Distill Their Models
“Antropic the company said actually in a letter to the Senate Banking Committee recently that basically the Chinese open source companies are bootstrapping their development of their state-of-the-art models by effectively breaching the terms of service of Antro…”
Rory O'Driscoll Jul 2, 2026 ▶ 18:25 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Anthropic Settled Book Copyright Lawsuit Over IP Scraping
“All the foundation models, including Anthropic, were trained on other people's IP. To the point where Antropic recently settled litigation with a whole bunch of copyright holders on books because they had, quote, unquote, unfairly, to use Dario's word, applied…”
Rory O'Driscoll Jul 2, 2026 ▶ 17:43 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Anthropic delayed shipping its latest model due to US government concerns
“We're seeing Anthropic unable to ship the most recent model until they satisfy the concerns of the US government.”
Rory O'Driscoll Jun 25, 2026 ▶ 25:20 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 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
Peets: Anthropic sales organization operates on group quotas rather than individual metrics
“They have a group quota.”
Chad Peets May 23, 2026 ▶ 25:48 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Anthropic SPVs are charging up to 8% in upfront fees
“Some of the package pricing on these SPVs for Anthropic has just been the most egregious face ripping I've ever seen. I mean it's like, it's just, oh, I mean like eight percent up front.”
Harry Stebbings Apr 23, 2026 ▶ 1:09:32 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Prediction Held up
Levie: Enterprises cannot shift AI liability to providers like Anthropic
“I promise you, you're not going to be able to blame Anthropic when something goes wrong. And so if you can't blame Anthropic when something goes wrong, then at some point it doesn't really work to tell the company, like to tell your customer, well, That, that …”
Aaron Levie Apr 20, 2026 ▶ 32:51 Aaron Levie: Everyone is Wrong; We'll Have More Developers in 5 Years · 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
Prediction Held up
Lemkin: Claude Code will aggressively attack Figma's business this year
“So I believe it will aggressively attack parts of Figma this year, even though they're key partners.”
Jason Lemkin Feb 26, 2026 ▶ 19:13 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 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
O'Driscoll: Anthropic's three-year 10x revenue growth is unprecedented in tech history
“The truth is you've never seen a company grow 10 X in gap revenue and runway year on year for three years. Right? At this scale. It just hasn't happened.”
Rory O'Driscoll Feb 19, 2026 ▶ 6:52 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 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
Lemkin: Anthropic cut off xAI's access to its models
“Even little things like Anthropic cutting off XAI's access to Anthropic this week.”
Jason Lemkin Jan 15, 2026 ▶ 11:08 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
O'Driscoll: Anthropic's revenue multiple is lower than Palantir's
“It's a much lower revenue multiple than Palantir. It's kind of comparable with Cloudflare for God's sake in the public markets.”
Rory O'Driscoll Jan 15, 2026 ▶ 3:04 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
Prediction Held up
Stebbings: Anthropic Projects Reaching $70B in ARR by 2028
“Anthropic projects seventy billion in ARR by 2028.”
Harry Stebbings Nov 13, 2025 ▶ 13:36 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 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 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 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
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
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 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
Prediction Held up
Kant: Poolside, OpenAI, and Anthropic will rival Big Tech in AI
“What I would like to see and what I think is going to happen is that it's not just Google, Amazon, and Microsoft. It's going to be, you know, an open eye, an anthropic, a poolside, and a set of companies who are able to get that massive escape velocity needed …”
Eiso Kant Oct 7, 2024 ▶ 53:29 Eiso Kant, CTO @Poolside: Raising $600M To Compete in the Race for AGI | E1211 · 20VC with Harry Stebbings
Assertion Supported
Sunak: DeepMind, Anthropic, and OpenAI agreed to grant UK early model access
“We're working with the companies themselves, DeepMind, Anthropic and OpenAI. I'm pleased that they've said that they will give early or priority access to the models.”
Rishi Sunak Jun 14, 2023 ▶ 0:14 Rishi Sunak: The UK's New High Potential Visa; Rishi's £100M AI Task Force | E1025 · 20VC with Harry Stebbings
Assertion Supported
Salesforce Spends $6B on Engineering and $300M on Anthropic Annually
“Salesforce spends six billion a year on engineering, and that probably includes QA and all the rest of it, but that's the right comp. And they're going to spend three hundred million dollars this year on Anthropic.”
Rory O'Driscoll Sep 3, 2026 ▶ 1:03:29 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Assertion Supported
Katz: Anthropic chose ClickHouse after asking Claude for a recommendation
“If you ask Anthropic how they chose to use ClickHouse, they'll tell you they asked Claude, what technology should we use for this specific observability use case? And Claude suggested ClickHouse.”
Aaron Katz Aug 31, 2026 ▶ 16:34 ClickHouse CEO: AI Margins Need to Improve | Revenue Concentration Should be a Concern
Assertion Supported
Stebbings: Anthropic achieved its first quarterly profit on $11.5B in Q2 revenue
“Anthropic turns its first profit on 11 and a half billion dollars of Q two revenue.”
Harry Stebbings Aug 20, 2026 ▶ 28:34 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
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