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

Insight
O'Driscoll: $1T AI revenue requires taking 20% of engineering payroll
“My rough math says it's something roughly like five or seven percent Of every knowledge worker salary and 20% of every engineering salary.”
Rory O'Driscoll May 21, 2026 ▶ 12:41 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
Prediction Not checkable as stated
O'Driscoll: OpenAI and Anthropic growth will stall unless enterprise software scales
“If Sierra doesn't grow, let me put it bluntly, if Sierra doesn't grow, then at some point, OpenAI and Entropic will stop growing because their customers today are primarily software companies for coding, right? And selling through software companies to corpora…”
Rory O'Driscoll May 21, 2026 ▶ 43:14 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
Prediction Open · timeframe May 2031
O'Driscoll: Elon Musk's OpenAI Lawsuit Appeal Will Fail
“He's going to appeal it. It won't get a second past Appeal, and it'll go away, right?”
Rory O'Driscoll May 21, 2026 ▶ 1:14:20 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
Assertion Not checkable as stated
O'Driscoll: OpenAI has surplus compute tokens while Anthropic does not
“And therefore my conclusion is OpenAI has surplus tokens and Anthropic does not.”
Rory O'Driscoll May 21, 2026 ▶ 1:09:45 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
Assertion Contradicted
Lemkin: Anthropic has secured more compute capacity than OpenAI
“And now Anthropik, I hate the five D eight D chess metaphor, but now it's gonna, it's figured out a way to have more capacity than open AI.”
Jason Lemkin May 14, 2026 ▶ 10:44 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Prediction Not checkable as stated
Weitzman: OpenAI ads will be massive due to deep user context
“Of course. Yeah, massive. Massive, massive. Because it knows so much about you.”
Cliff Weitzman May 9, 2026 ▶ 30:23 Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries · 20VC with Harry Stebbings
Assertion Partly supported
Speechify is among 200 companies testing ads on OpenAI
“We're one of the 200 companies that's provisioned to test ads on OpenAI.”
Cliff Weitzman May 9, 2026 ▶ 13:59 Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI and Anthropic capture almost all commercial LLM revenue
“And when you look at what's actually going on, the big two guys are getting all the money. Gemini, for some reason, doesn't appear to be able to do a great job of developing code or love and just getting that kind of traction because coding is where it's all h…”
Rory O'Driscoll May 7, 2026 ▶ 20:13 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
Assertion Not checkable as stated
O'Driscoll: OpenAI lost market share to Anthropic in late 2024
“And there's no doubt in the back half of last year, OpenAI failed at the first part of that job. They didn't build great models. And as a result, their traction relative to entropics declined markedly. Their market share declined markedly, right?”
Rory O'Driscoll Apr 30, 2026 ▶ 2:12 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Opinion
Adam Foroughi: Building a Startup Merely as an LLM Interface Is Extremely Risky
“I would be very, very nervous if I was building a business as an interface on top of those companies.”
Adam Foroughi Apr 27, 2026 ▶ 33:55 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
Opinion
O'Driscoll: AI race is two-way fight between Anthropic and OpenAI
“I think it's a two-way fight. Antropic has the advantage of clarity and focus. OpenAI has the advantage of the consumer business.”
Rory O'Driscoll Apr 16, 2026 ▶ 0:36 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2030
Jason Lemkin predicts OpenAI will reach $100B in ad revenue
“I like this as a goal for 2030 because it's clear what people should be doing... And so I think because it is achievable, it will be achieved. I actually think it will be achieved.”
Jason Lemkin Apr 16, 2026 ▶ 49:59 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Insight
O'Driscoll: Even $100B in ad revenue will not cover OpenAI's burn
“Consumer alone ain't going to be enough to feed this beast, because your competitor, who's all in on enterprise, Is, you know, already at 30, right? And you're, so that was my, as I say, I almost feel like a jerk saying it's like, hey, congratulations on your …”
Rory O'Driscoll Apr 16, 2026 ▶ 49:18 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 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
Insight
Lemkin: You must fire any executive who publicly argues with the CEO
“If you have an executive that's truly arguing with the CO in public, in the media, right? And or like Dario back in the day at OpenAI going directly to the board with craziness, they gotta go. Like, it doesn't matter. They gotta go. They, you cannot be out in …”
Jason Lemkin Apr 16, 2026 ▶ 1:28:07 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Prediction Not checkable as stated
Midha: Compute shortages will prevent top AI labs from hitting revenue targets
“I think if there's any reason why OpenAI, Anthropic, Gemini, and so on don't hit their revenue targets over the next few years, it's because they won't have access to enough compute.”
Anjney Midha Apr 14, 2026 ▶ 48:23 The Early Days of Anthropic & How 21 of 22 VCs Rejected It | The Four Bottlenecks in AI | Anj Midha · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2028
Reyna: OpenAI, Google, and ElevenLabs will buy new foundational model startups
“OpenAI and Anthropic will end up, and Google will end up buying, and 11 Labs will end up buying, like, all of the new foundational model companies that will be popping up and creating research and paying just, like, a few billion here, a few billion there, and…”
Carles Reina Apr 11, 2026 ▶ 1:23:19 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
Opinion
Reyna: OpenAI, Anthropic, and Cursor are enterprise AI's only blue-chip brands
“I think, like, the two companies that today have been able to make it is, or three companies, if you want, OpenAI, Anthropic, full respect for them, Cursor. The three of them, I think, for me, are, like, Cursor has killed enterprise unbelievably well. Yeah, th…”
Carles Reina Apr 11, 2026 ▶ 38:46 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI at $380B valuation is a better buy than Anthropic at $850B
“I would argue that you would buy OpenAI on one proviso. You could sit down with the board and say, what are you going to do about this? Because it doesn't take a lot to fix this thing, right? To just stop screwing around and focus, right? And, you know.”
Rory O'Driscoll Apr 9, 2026 ▶ 26:38 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lemkin: OpenAI's executive reboot stems from Anthropic outpacing them
“If we step back a minute, it ties to Anthropic passing them. You don't just sit there and make no changes on the team when your competitor over the last six months has radically changed the competitive posture.”
Jason Lemkin Apr 9, 2026 ▶ 12:26 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Insight
Physical infrastructure businesses are most defensible against AI models
“I think some of the most defensible businesses in the age of, you know, anthropic and open AI are businesses that actually do something physical. Like they require actual specialization and they require infrastructure.”
Andrew Dudum Apr 4, 2026 ▶ 25:58 How Hims & Hers Reached a $4.3BN Market Cap on $2.3BN of Revenue | Andrew Dudum · 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
Opinion
Lemkin: OpenAI's Strategic Direction with Sora Was Significantly Flawed
“A big part of the whole strategic direction of the company was flawed.”
Jason Lemkin Apr 2, 2026 ▶ 10:04 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Assertion Partly supported
Lemkin: Sora generated single-digit millions while burning billions in compute
“From what I read, Sorum made single digit millions of revenue, right, and was consuming a million a week, which actually sounds way too low, right? It must have consumed billions and made single digit millions.”
Jason Lemkin Apr 2, 2026 ▶ 10:09 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 Not checkable as stated
O'Driscoll: OpenAI needs $20B in ad revenue within two years
“If these guys aren't doing twenty billion within a couple of years, they're not even in the game.”
Rory O'Driscoll Apr 2, 2026 ▶ 13:06 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Prediction Not checkable as stated
O'Driscoll: OpenAI can still exit as largest standalone model player
“I mean, they're doing finally the right stuff, you know, perhaps a year, year and a half later, but it's still clear to me that if you just take a big deep breath and you are running that organization, focus on the two or three things, get a little more sensib…”
Rory O'Driscoll Mar 26, 2026 ▶ 8:03 Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI and Anthropic Face More Attack Surface Than Any Global Company
“The truth is, OpenAI and Entropic have the most amount of surface area to attack of any company in the world.”
Rory O'Driscoll Mar 12, 2026 ▶ 0:47 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2026
Stebbings: OpenAI will IPO in October 2026 at $1.5 trillion valuation
“I'm going to say October and I'm going to say it's going to go out at 1.5 trillion.”
Harry Stebbings Mar 5, 2026 ▶ 31:04 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Calacanis: OpenAI revokes sales team keycard access to research buildings
“Open a don't even let the salespeople talk to the engineers, the researchers, they're not even allowed their cards don't work at the building of engineers because they don't want to be bothered by the go to market team.”
Jason Lemkin Mar 5, 2026 ▶ 13:09 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Calacanis: OpenAI staff forfeit eight-figure equity packages to leave early
“I mean, people are leaving, you know, eight figures of vesting stock at OpenAI because they just, they want to work somewhere else after 13 months or six”
Jason Lemkin Mar 5, 2026 ▶ 12:17 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Assertion Partly supported
O'Driscoll: Anthropic retained all seven founders while OpenAI lost most
“Which is why they still have the seven founders when the other guys across the street have lost almost all but one or two of the founders.”
Rory O'Driscoll Mar 5, 2026 ▶ 5:41 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Prediction Not checkable as stated
Zinman: OpenAI and Anthropic won't capture all enterprise software value
“So I'm not saying people will not use Entropic and OpenAI, for sure they will, but I don't think they're gonna capture all the enterprise value. Because they have a much bigger opportunity ahead of them, and it's not their focus.”
Eran Zinman Mar 2, 2026 ▶ 11:48 Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman · 20VC with Harry Stebbings
Opinion
Jerry Murdock: Google and Gemini are better long-term assets than OpenAI
“They can, and they are long-term better assets. They've got, if I have an autonomous agent business and I've got Gmail, you're going to have a phenomenal asset that open AI doesn't have.”
Jerry Murdock Feb 28, 2026 ▶ 55:36 The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI erred by letting Anthropic capture enterprise market share
“So, you'd have to say it wasn't the right play this year or last year, right, to allow Entropic so much space in the enterprise, and maybe perhaps doing all the things you were trying to do took your eye off the ball on winning the two or three things that you…”
Rory O'Driscoll Feb 26, 2026 ▶ 57:10 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Insight
Swisher: AI models disrupt public market belief in SaaS terminal value
“For the first time ever with this AI wave, people are questioning the terminal value of SaaS, right? These were supposed to be like insurance companies, you know, annuity streams that just have revenue streams and profit pools forever and ever and ever. And fo…”
Lucas Swisher Feb 23, 2026 ▶ 1:23 Insights from Coatue's Growth Investor Lucas Swisher · 20VC with Harry Stebbings
Prediction Not checkable as stated
Emberikos: Enterprise AI will consolidate around multi-functional super assistants
“But I think that's probably temporary, and then over time, I think we're gonna end up with agents that kind of can do anything for you. This is kind of what I was saying earlier. Like, there's just, like, a super assistant. You talk to it about anything.”
Alexander Emberikos Feb 21, 2026 ▶ 44:08 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Assertion Contradicted
Emberikos: OpenAI is the only firm building OS-level sandboxing for Windows AI agents
“We're basically the only company that cares about OS level sandboxing for coding agents. For instance, there's none that exists on Windows. We're the ones building that and we're doing it in open source, so hopefully other people can use it.”
Alexander Emberikos Feb 21, 2026 ▶ 1:00:58 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Disclosure
Emberikos: OpenAI has plenty of training data for AI coding models
“I think that from what we've seen, and you know, I would defer to my research team on this, but I feel like we feel like we have plenty enough data to build really good coding models.”
Alexander Emberikos Feb 21, 2026 ▶ 35:43 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Disclosure
Emberikos: The vast majority of OpenAI code is now written by AI
“I don't have a percentage stat for you, but I would say, like, the vast majority of code is written by AI, and I would say that now, probably, like, most people are not even, like, opening IDEs. Maybe if they are opening IDEs to, like, maybe you want to own th…”
Alexander Emberikos Feb 21, 2026 ▶ 18:51 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2031
Emberikos: OpenAI aims for AI agents that run micro-systems without human review
“So, like, I think we want to get to a world where you can have an agent that is un-bottlenecked, right? That you trust to, like, own an entire microsystem or internal tool or whatever, and can do the full iterative loop, including feedback from users, without …”
Alexander Emberikos Feb 21, 2026 ▶ 41:56 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Disclosure
Emberikos: OpenAI is building Atlas browser for safe enterprise agentic browsing
“And, you know, I think it's quite unusual, like in OpenAI, we're building a browser, Atlas, right? And you might wonder why. And there are many reasons why, but I think one of the key reasons is that by building a browser, we can build sort of S and by control…”
Alexander Emberikos Feb 21, 2026 ▶ 14:05 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Disclosure
Emberikos: OpenAI serves its trained models to direct competitors
“Actually, our job is the distribution of intelligence, and this is really unintuitive, but like, we put all this effort into training these models, and then we serve these models to our competitors.”
Alexander Emberikos Feb 21, 2026 ▶ 0:28 OpenAI's Codex Lead: Why Coding as We Know It is Over · 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
Opinion
Cannon-Brookes: VCs back OpenAI at huge valuations for logo marketing
“One thing that they don't say is a lot of VCs want the loose side on the wall, so when you walk into the office, on the wall is a nice logo that says, oh, you invested in OpenAI. You invested in Anthropic. Well, if you put money at three hundred fifty billion,…”
Mike Cannon-Brookes Feb 12, 2026 ▶ 1:00:17 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 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
Opinion
Lemkin: NVIDIA would be forced to bail out OpenAI if needed
“If open AI needs a bailout, it has to bail them out. It has no choice”
Jason Lemkin Feb 5, 2026 ▶ 58:07 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
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