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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
Osika: Invest in xAI's Grok and short OpenAI
“I'd invest in GroK, and I would probably short Anthropic. No, I would short OpenAI.”
Anton Osika Aug 18, 2025 ▶ 0:04 Lovable CEO, Anton Osika: The State of Foundation Models, Grok vs OpenAI, and Replit vs Bolt · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2031
OpenAI or Anthropic Will Exceed $10 Trillion Valuation Within Five Years
“I could definitely see one of them being a 10 trillion dollar company maybe even significantly higher. It feels Like the opportunity associated with being the frontier model is so large that it will just like eat up so much of the other demand within the econo…”
Brendan Foody Jun 1, 2026 ▶ 51:10 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
Prediction Open · timeframe Nov 2026
O'Driscoll: Anthropic Will Pass OpenAI in Scale and Profitability Shortly
“Within a couple of quarters, Anthropic will be visibly and obviously ahead. Profitable, growing more quickly, and bigger.”
Rory O'Driscoll May 28, 2026 ▶ 0:14 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2031
Jason Lemkin: SpaceX, OpenAI, Anthropic combined IPO values will top past 20 years
“The big three, SpaceX plus OpenAI plus Anthropic, their value at IPO will exceed every other IPO for the last 20 years combined.”
Jason Lemkin Apr 9, 2026 ▶ 0:43 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2026
Randle: OpenAI could raise at a $1T valuation next year
“I think it'll be a trillion dollar company next year. Yes. I think they could probably raise at the end of the year. Ah, you know, end of the year Q two, I think open AI could raise it a trillion dollars. No problem.”
Everett Randle Nov 10, 2025 ▶ 14:11 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Open · timeframe Jul 2030
Casado: OpenAI Lost Its Early Leads In Code, Image, And Video Generation
“OpenAI was the first to code, right? With GitHub Copilot. I mean, they provided the weights. As far as I know, and they lost that. And they were first to image with Dali, and they lost that. And they were the first to video with Sora. And as far as I can tell,…”
Martin Casado Jul 28, 2025 ▶ 19:17 a16z GP, Martin Casado: Anthropic vs OpenAI & Why Open Source is a National Security Risk with China · 20VC with Harry Stebbings
Opinion
Stebbings: I would put my entire $400M fund into OpenAI
“If I could do anything without fear of retribution from my LPs, I'd put my four hundred million fund into OpenAI.”
Harry Stebbings Jul 11, 2025 ▶ 45:20 20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
Prediction Held up
O'Driscoll: OpenAI misses next year's revenue target by 40% if growth matches Google
“If all OpenAI is, Is just as good as Google, then it's going to miss its number next year by about 40%.”
Rory O'Driscoll Jun 5, 2025 ▶ 47:06 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Opinion
Benioff Passes on OpenAI, Anthropic, and xAI Over Product Commoditization
“I don't know if I'd really want to invest in any of them right now because I think in those cases we're seeing all of them to being about the same kind of product. A lot of them are really becoming the same Technology.”
Marc Benioff Dec 9, 2024 ▶ 17:33 Marc Benioff, Salesforce Founder: Why Salesforce Isn't Hiring Software Engineers | E1236 · 20VC with Harry Stebbings
Assertion Supported
Mollick: OpenAI's $3B revenue run rate is largely an accident
“I mean, they're incidentally making three billion dollar run rate this year, I think by like just accident, but there isn't like a, there isn't really a product there right now.”
Ethan Mollick Jul 31, 2024 ▶ 24:14 Ethan Mollick: Why OpenAl Abandons Products, The Biggest Opportunities They Have Not Taken | E1184 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Sam Altman: OpenAI will steamroll startups built on static model assumptions
“It would seem to me that 95% of the world should be betting on the latter category, but a lot of the startups have been built in the former category. When we just do our fundamental job, we're going to steamroll you.”
Sam Altman May 24, 2024 ▶ 11:39 Sam Altman, Arthur Mensch and more discuss:Which Startups Are Threatened vs Enabled by OpenAI?|E1156 · 20VC with Harry Stebbings
Insight
Hulme: AGI hype correlates directly with founders' capital fundraising needs
“I think there is a Correlation between how aggressively people predict AGI is coming and how much capital they need to raise. So you've got Emodi from Anthropic, you've got Altman, OpenAI, Musk, XAI, all of these guys are saying that it's just around the corne…”
Tom Hulme May 8, 2024 ▶ 1:11:38 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
Opinion
Hulme: GV would not invest in OpenAI at a $90B valuation
“I would struggle To make that investment today. No.”
Tom Hulme May 8, 2024 ▶ 50:12 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Altman: OpenAI will steamroll startups building static software wrappers
“When we just do our fundamental job because we, like, have a mission, we're going to steamroll you.”
Sam Altman Apr 15, 2024 ▶ 0:23 Sam Altman & Brad Lightcap: Which Companies Will Be Steamrolled by OpenAI? | E1140 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Khosla: OpenAI's AGI Could Eliminate the Need for Human Work
“OpenAI is going after a big, hairy, audacious goal of building an AGI. That, to me, is worth pursuing as an investment, but also for society. It may eliminate the need to work for society, Lots of issues there, but it could be really, really exciting if it wor…”
Vinod Khosla Feb 24, 2020 ▶ 32:44 20VC: Vinod Khosla on What Venture Assistance Really Means, Why Many VCs Are Not Qualified To Advise Founders & Why Startups Can Innovate So Much Faster Than Incumbents
Opinion
Stebbings: OpenAI fumbled voice AI due to poor management and hiring
“Well, I think with all candor, that's because of incredibly poor management. And hiring, and that was theirs to take, and they fumbled the bag across every spectrum.”
Harry Stebbings Sep 5, 2026 ▶ 29:21 How to Build Your Own Data Center & Why Every Startup Should Do It
Opinion
Reyes: OpenAI and Anthropic are currently in the Netscape and Yahoo era
“We are probably in like the Yahoo era where we don't actually have, or at least widely recognize The Googles of the world, or like the sort of the thing that comes after. And so today, when I look at OpenAI and Anthropic, there are, I think, more analogies to …”
Eno Reyes Aug 29, 2026 ▶ 55:48 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Opinion
Reyes: Frontier labs must pursue regulatory capture or multi-model architectures
“Part of what needs to happen in order to make these companies like Anthropica and OpenAI realize the value is they either A, which they're pursuing, have to go through regulatory capture, in which case they go and they tell, they sort of scare politicians int…”
Eno Reyes Aug 29, 2026 ▶ 16:35 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Prediction Not checkable as stated
Lemkin: Databricks and OpenAI IPOs will be nail in coffin for SaaS
“I think it will be the nail in the coffin for almost every public software company. And what I mean is when Stripe and data, like, okay, there's OpenAI, there's Anthropic, we can put them in a different category, right? They clearly are on many levels. When Op…”
Jason Lemkin Aug 27, 2026 ▶ 1:10:21 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Prediction Not checkable as stated
O'Driscoll: OpenAI will IPO later and lower than Anthropic
“The rank, the most, the big picture fact is the ranking has changed, and you're now number two. So you will go out later then and a lower price than the other guys, unless you change the trajectory massively.”
Rory O'Driscoll Aug 27, 2026 ▶ 29:46 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Prediction Open · timeframe Aug 2029
Anthropic will IPO soon after pulling ahead of OpenAI's ChatGPT
“They will go public because this is peak brass ring moment, and you know, you could argue the trends in 27 are tougher. You've pulled ahead of ChatGPT, so just put a nail in the entropic pit, right? You've pulled ahead of ChatGPT comfortably, OpenAI, to a poin…”
Rory O'Driscoll Aug 12, 2026 ▶ 44:59 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Prediction Not checkable as stated
Stebbings: Sam Altman and Dario Amodei will successfully lobby for AI restrictions
“I just think Sam Altman is someone who I would never, ever bet against, and I think he's the best politician in the world, and I think when he says something, he says it with intent, and when he says we should give five percent away to the administration, he's…”
Harry Stebbings Aug 2, 2026 ▶ 19:23 Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
Prediction Not checkable as stated
Angelopoulos: Open-source AI pressure could cause insolvency for leading frontier labs
“And I think that the reason to be worried is because if the open source ecosystem somehow makes the cost saving opportunity for businesses much more salient and therefore decreases the revenue of companies like OpenAI and Anthropic within the enterprise, that …”
Anastasios Angelopoulos Aug 2, 2026 ▶ 1:03:26 Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
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
Insight
O'Driscoll: Major Startup Breakthroughs Rely on Boundary Pushing Legalized Upon Success
“So many breakthroughs rely on a little bit of pushing the boundaries. I mean, Uber did with taxi regulation. Airbnb did with regulation. You're right. Polymarket did in terms of how they're regulated. So I'm actually going to get off my high horse and say you …”
Rory O'Driscoll Jul 16, 2026 ▶ 59:52 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
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
Opinion
O'Driscoll: Microsoft and OpenAI Are in a Stale Marriage Looking for Divorce
“Microsoft owns 30% of OpenAI. If ownership stake resulted in besties, they'd be besties. They're not besties. They're in a stale marriage looking for a divorce, but can't quite pay, you know, pay the tax, right?”
Rory O'Driscoll Jul 9, 2026 ▶ 9:10 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Opinion
O'Driscoll: Microsoft lacks compelling proprietary AI products beyond OpenAI stake
“So when you zoom out a million miles, Microsoft, which is in the software business, unlike Apple, and therefore can't afford to stay apart from the great AI wars, other than its equity ownership in open AI doesn't have anything compelling to bring to the table…”
Rory O'Driscoll Jul 2, 2026 ▶ 35:09 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 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
Opinion
O'Driscoll: OpenAI and Anthropic rely on $300B spent by other companies
“The whole reason the OpenAI and Entropic models work is because other idiots have spent the three hundred billion dollars on their behalf.”
Rory O'Driscoll Jun 25, 2026 ▶ 0:44 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Opinion
Petersen: Anthropic is a better investment than OpenAI at equal valuation
“I think I'm going Anthropic. No offense, because Sam's a friend of mine, but. Yeah, the enterprise business seems great. And the team, I think there's a lot of value of like this cohesive team that's been together forever, and OpenAI's had ups and downs, and p…”
Ryan Petersen Jun 20, 2026 ▶ 26:36 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Opinion
Degnan: Salespeople at mega-funded AI startups are passive passengers lacking skill development
“These companies all, pretty much everyone's a passenger, because there is no accountability. You're not learning anything from a sales, you know, perspective. Eventually that will come to bite you in the, in your butt, in your career.”
Chris Degnan May 23, 2026 ▶ 28:23 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Altman Offered $2M in OpenAI Tokens to Every YC Startup
“Sam Altman just offered two million dollars In open AI tokens to every YC startup in the current batch in exchange for equity.”
Harry Stebbings May 21, 2026 ▶ 1:02:36 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI has compute but flawed models; Anthropic lacks compute
“OpenAI got one job right, they have enough compute, and they got the model wrong, so that's why they're in trouble. And Entropic did it the exact opposite way, right? They got the model perfect. In fact, they may have over-succeeded, and as a result of that, t…”
Rory O’Driscoll Apr 30, 2026 ▶ 19:49 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Opinion
Reyna: I would choose to acquire Anthropic over OpenAI
“Anthropic. And I've put it online, like, multiple times.”
Carles Reina Apr 11, 2026 ▶ 1:23:38 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI's acquisition of TBPN is an absurd vanity project
“So I challenge that. I think it's a vanity project and absurd.”
Rory O'Driscoll Apr 9, 2026 ▶ 17:40 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Opinion
O'Driscoll: xAI is at best fourth in LLMs while burning $12B yearly
“We just had a long conversation on Entropic versus OpenAI, And they're kind of number one and two in this space, and Gemini, Google is almost certainly number three, so x.ai is number four in the kind of model LLM space at best, burning twelve billion dollars …”
Rory O'Driscoll Apr 9, 2026 ▶ 37:40 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Opinion
O'Driscoll: OpenAI's rapid executive departures smack of management carelessness
“To me, even all these people change, you know, I, I'm tempted to make that, you know, that the famous Oscar Wilde quote in the importance of being earnest, you know, to lose one parent might be an accident when he was talking to the, this woman was talking to …”
Rory O'Driscoll Apr 9, 2026 ▶ 15:05 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Opinion
Lemkin: Investing in OpenAI at high valuations is too risky due to non-technical leadership
“I'm just not into the tumult at open AI. I'm not into the drama. I'm not into a non tech, non deeply technical founder leadership. It's just not my vibe. Like I wouldn't invest in anything like open AI at a high price. It doesn't matter what it is. Cause it's …”
Jason Lemkin Apr 9, 2026 ▶ 28:09 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Opinion
Stebbings: OpenAI should acquire Sierra and make Bret Taylor CEO
“It's the best thing for OpenAI not to buy Sierra, incorporate that as a customer support product, and have Brett Taylor come in as the day-to-day CEO, and Sam can be fundraiser, Sam can be master of...”
Harry Stebbings Apr 2, 2026 ▶ 15:33 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Opinion
Lemkin: OpenAI is struggling and facing an internal code red
“You can smell open AI struggling right now. You can just smell it. You can smell the code red and the fact that they said yesterday, we have to concentrate on enterprise. We have to stop side projects.”
Jason Lemkin Mar 19, 2026 ▶ 2:09 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Opinion
Mitchell Green: $2B valuations for AI spinout ideas are complete lunacy
“People that spin out of Like, Anthropic or OpenAI and raise money at, like, two billion dollars for a freaking idea. Like, there's nothing more than an idea and a napkin. To us, that seems complete lunacy.”
Mitchell Green Mar 7, 2026 ▶ 0:31 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Opinion
Mitchell Green: Multi-billion VC funds are insane and require hitting next Google
“I think it's insane. I think these funds are way too, and they, just do the math, the fund math on like how, they're clearly, you have to have the next open, you have to have the next Google, effectively, or the math doesn't work, I don't think.”
Mitchell Green Mar 7, 2026 ▶ 56:16 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
What-if
O'Driscoll: Musk's death would cut Tesla 80%, Altman's cuts OpenAI 25%
“Tesla trades at a trillion today. I think if Elon died tomorrow, they traded two hundred billion. OpenAI trades at eight hundred billion today. I think if Sam Altman died tomorrow morning, we traded six hundred billion.”
Rory O'Driscoll Mar 5, 2026 ▶ 29:15 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Opinion
Emberikos: Enterprise AI adoption does not require forward-deployed engineers
“So, so even though I am literally hiring FDs and if you're an FD, please apply for a job with me. I actually disagree with that entirely.”
Alexander Emberikos Feb 21, 2026 ▶ 9:08 OpenAI's Codex Lead: Why Coding as We Know It is Over · 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
Opinion
Cohen: Sierra, OpenAI, and Anthropic Fail at Complex Vertical AI Needs
“There is nothing even remotely closed to what is needed when you go to a complex vertical out there. Okay. And it's definitely not in the kind of Sierra level, but even if you take it to the level of the APIs, If I'm kind of taking an anthropic and an open AI,…”
Ariel Cohen Feb 7, 2026 ▶ 21:00 20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen
Prediction Not checkable as stated
Junestrand: Anthropic and Gemini will outperform OpenAI in enterprise AI
“I'll bet based on what I've seen in the last sort of three, six months. I think for our type of work, it will either be cloud or Gemini. That is the top model. And it will be dependent on if context window is a very important factor or not. So far it is not be…”
Max Junestrand Jan 26, 2026 ▶ 15:04 Legora CEO, Max Junestrand: $7M ARR in a Day | Harvey vs Legora: Is a Legal AI Winner Takes All? · 20VC with Harry Stebbings
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