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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

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
Opinion
O'Driscoll: Drop in Security Stocks Following Anthropic Announcement Was Absurd
“The response of security stocks going down to the Anthropic announcement was absurd. I think anyone who's cutting back on the security budget in twenty-twenty-six is missing the point, right?”
Rory O'Driscoll Apr 9, 2026 ▶ 1:21:59 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
Prediction Not checkable as stated
O'Driscoll: Application security companies must adopt AI analysis or become redundant
“If you were doing application security or code review for secure security code review, you're probably going to have to either incorporate how this works in your analysis or you'll be redundant.”
Rory O'Driscoll Apr 2, 2026 ▶ 22:18 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Assertion Contradicted
Stebbings: Anthropic made $6B in February, exceeding Databricks' lifetime revenue
“28 day month of February, where they did six billion in revenue, which was more than Databricks has done in their entire lifetime.”
Harry Stebbings Apr 2, 2026 ▶ 1:16 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 Not checkable as stated
Rajaram: Most bolt-on AI products are thin wrappers over OpenAI or Anthropic
“Most bolt on players are not doing it. They're simply using a GPT or anthropic model. And they're basically just adding a thin layer. You have to rebuild the entire experience end to end.”
Gokul Rajaram Mar 16, 2026 ▶ 20:32 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2027
O'Driscoll: Anthropic will eventually submit to government demands to protect B2B revenue
“They won't clearly get a two hundred million dollar revenue deal with the U S department of war, but in a perfect world, if they bend the knee prevail on the law, what we've seen in multiple other situations is you end up at some kind of, you know, acquiescenc…”
Rory O'Driscoll Mar 12, 2026 ▶ 8:44 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Prediction Not checkable as stated
O'Driscoll: Anthropic May Win Lawsuit But Lose Broader Government Battle
“The consensus is, in law, Anthropic would probably win a good slug of this case, which is different than saying they're going to win the fight.”
Rory O'Driscoll Mar 12, 2026 ▶ 0:00 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Prediction Not checkable as stated
Clements: Anthropic and select private AI companies could reach $1T valuations
“I think that company and a small handful of companies in the private market today are operating on a different plane. You know, I think it is not bombastic to say that some of those businesses could be trillion dollar companies.”
Miles Clements Mar 9, 2026 ▶ 35:45 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Prediction Partly held up
O'Driscoll: Anthropic and SpaceX's next funding rounds will be IPOs
“You've got to believe that the next round for this, Antropic, and SpaceX are all public offerings.”
Rory O'Driscoll Mar 5, 2026 ▶ 26:30 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
Prediction Open · timeframe Feb 2029
Rory O'Driscoll: CrowdStrike will not be obviated by Anthropic's security launch
“I don't think CrowdStrike's obviated by this. I think it will totally be fine. It'll continue to be a business.”
Rory O'Driscoll Feb 26, 2026 ▶ 5:14 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 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
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
Opinion
Swisher: Anthropic's multi-cloud, multi-chip strategy gives unappreciated optionality
“In the last strategic decision that they made that I think is really Sort of unappreciated by the market is they built for every cloud and they built for every chip platform, and that gives them incredible optionality and a lot of people want them to win.”
Lucas Swisher Feb 23, 2026 ▶ 55:27 Insights from Coatue's Growth Investor Lucas Swisher · 20VC with Harry Stebbings
Opinion
O'Driscoll: Anthropic is clearly the best AI model for enterprise
“Anthropic looks like, for enterprise, it's clearly the best model.”
Rory O'Driscoll Feb 19, 2026 ▶ 5:35 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 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
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
Opinion
Lemkin: Anthropic is a generational company whose only weakness is consumer
“Anthropic is, I mean, it's a generational, generational company. It changed coding. It changed everything. But the only place Anthropic is weak is consumer.”
Jason Lemkin Feb 12, 2026 ▶ 1:04:10 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 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
Prediction Open · timeframe Jan 2031
O'Driscoll: Anthropic will eventually become a cash-flow profitable business
“Fundamentally, however, I don't doubt the fact that a profitable, and defined by that as free cash flow, operating income business, will emerge from something like, I mean, Atropic's not going to not have a profitable business model because this clearly is con…”
Rory O'Driscoll Jan 29, 2026 ▶ 21:11 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Assertion Partly supported
O'Driscoll: OpenAI and Anthropic generate virtually all private AI revenue
“So, objectively speaking, if you kind of add up all the AI revenue, you know, you're going to get thirteen billion for OpenAI, four billion for Entropic, and everything else is in the noise, right?”
Rory O'Driscoll Jan 29, 2026 ▶ 47:49 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Disclosure
Junestrand: Legora shifted from exclusively OpenAI to majority Anthropic models
“We are pretty diehard Anthropic right now at the company in terms of the models that we deploy in our system. So initially we were only open AI. So so most of only open AI. And now we're a majority using Anthropic.”
Max Junestrand Jan 26, 2026 ▶ 11:14 Legora CEO, Max Junestrand: $7M ARR in a Day | Harvey vs Legora: Is a Legal AI Winner Takes All? · 20VC with Harry Stebbings
Insight
Junestrand: Anthropic Is Focusing on Enterprise While OpenAI Shifts to B2C
“We, I also think there's a difference between solving enterprise needs and solving B to C needs. And to me, there's a split happening or A perceived split, at least from my vantage point, which is that Anthropic is going more enterprise and OpenAI is going mor…”
Max Junestrand Jan 26, 2026 ▶ 16:04 Legora CEO, Max Junestrand: $7M ARR in a Day | Harvey vs Legora: Is a Legal AI Winner Takes All? · 20VC with Harry Stebbings
Opinion
O'Driscoll: Musk Is Wrong That OpenAI Was a Scheme to Cheat Donors
“So I think fundamentally, I think Elon's wrong on the core assertion. I don't think this was a cunning device to cheat everyone, because if they wanted to do that, they could have just done what Antropic did, which is the totally sensible interim stage of a pu…”
Rory O'Driscoll Jan 22, 2026 ▶ 36:07 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Insight
Weinberg: OpenAI and Anthropic revenues would explode even without new models
“I think if both companies literally just stopped shipping things, their revenues would still explode because there are going to be so many companies building on top of their models There are going to be so many different parts of the economy that adopt these t…”
Winston Weinberg Jan 19, 2026 ▶ 25:33 Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings
Insight
Weinberg: Product iteration speed is the main threat to application AI
“I think just moving fast enough on product, like that, that is always, I think, the biggest existential threat for all the application layer companies. And it's not necessarily that, you know, Anthropic or OpenAI are, you know, tomorrow gonna put 50% of their …”
Winston Weinberg Jan 19, 2026 ▶ 19:45 Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings
Opinion
Lovinsky: I am a buyer of Anthropic equity over OpenAI right now
“I'm a buyer of Anthropic at this point.”
Noam Lovinsky Jan 16, 2026 ▶ 36:09 20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman
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
Opinion
O'Driscoll: Skeptical the Market Can Support Ten Separate AI Research Labs
“It will be interesting to see, can the world support 10? Research labs coming up with 10 different variants of AI, all of which have to build either commercial or consumer businesses. I think on aggregate I'm fairly skeptical, but it's less a quality of, I mea…”
Rory O'Driscoll Jan 8, 2026 ▶ 34:05 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
Opinion
Lemkin: Google is corporate investor of the year for its massive stakes
“Owning almost 10% of SpaceX, owning, ah, perhaps 14% of Anthropic, depending on dilution, right? Now, and obviously, now this is the greatest in circular investment of all, owning the vast majority of Waymo, which is going to blow up. But those three are, like…”
Jason Lemkin Dec 22, 2025 ▶ 17:43 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2026
O'Driscoll: Anthropic will likely IPO in 2026, but Stripe will not
“I think Stripe, least likely, take it off the table. My gut would be Antropic gets it done.”
Rory O'Driscoll Dec 22, 2025 ▶ 1:02:17 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2028
Lemkin: Anthropic will go public at a $500 billion valuation
“20 X times 26 is five 20. I'm gonna guess five hundred billion IPO, right?”
Jason Lemkin Dec 11, 2025 ▶ 17:15 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
Opinion
Rory O'Driscoll: Microsoft-Anthropic-Nvidia compute deal has better fundamentals than peers
“Of all the round tripping deals, I would argue a Microsoft, Entropic, Nvidia deal probably has better principles and upside than most. I mean, some of the other round tripping deals look like they're already, you know, a bit shaky.”
Rory O'Driscoll Nov 27, 2025 ▶ 4:13 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Prediction Not checkable as stated
Shlomo: Developers will stick with Claude Code over superior models
“Like, even if now Gemini three comes out and it's a better model than Cloud and so on, then still there's gonna be a huge number of people staying with CloudCode because they're used to it and they built some things up the stack.”
Maor Shlomo Nov 24, 2025 ▶ 1:14:52 Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Harry Stebbings: AI coding startups pay 80% of pass-through revenue to Anthropic
“If you look at a Rapplet or a Lovable, 80% of their pass-through is too anthropic.”
Harry Stebbings Nov 17, 2025 ▶ 33:05 AI Fund’s GP, Andrew Ng: LLMs as the Next Geopolitical Weapon & Do Margins Still Matter in AI? · 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
Opinion
Randle: Prefers OpenAI at $500B over Anthropic at $350B
“And Sonnet and all the models that they have is probably still a little bit ahead of OpenAI, but I think given ChatGPT, I think I would probably rather do OpenAI at 500 than Anthropic at three 50, but I both think that they're relatively good investments even …”
Everett Randle Nov 10, 2025 ▶ 15:36 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Opinion
Lloyd: OpenAI has an edge over Anthropic because of ChatGPT
“I'm very, very bullish on open AI because I think they have a winning consumer product.”
Zach Lloyd Oct 17, 2025 ▶ 1:04:32 20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp
Insight
Degnan: Product-led growth fails alone in enterprise sales
“So PLG is great, but if you want to sell to the enterprise is hyper-political, and you have to have a sales process to do that. And at some point, The PLG motion will fail you, or it won't get you to that, that large enterprise. And if you aspire to sell the l…”
Chris Degnan Oct 10, 2025 ▶ 52:53 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan
Opinion
Jonathan Ross: OpenAI and Anthropic Are Both Highly Undervalued
“I'd want to invest in both. They're both undervalued. Highly undervalued.”
Jonathan Ross Sep 29, 2025 ▶ 1:08:42 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
What-if
Ross: OpenAI and Anthropic revenues would double with double compute
“If OpenAI were given twice the inference compute that they have today. If Anthropic was given twice the inference compute that they have today, within one month from now, their revenue would almost double.”
Jonathan Ross Sep 29, 2025 ▶ 0:28 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
Prediction Open · timeframe Sep 2030
Ross: OpenAI, Anthropic, and all hyperscalers will build custom chips
“I have no doubt that OpenAI will be able to build its own chips. I have no doubt that eventually, Anthropic will be building their own chips, that every hyperscaler will build their own chip.”
Jonathan Ross Sep 29, 2025 ▶ 13:06 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
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