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why aren't all 175 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 7 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
Scott: AI scaling laws have not hit a limit yet
“I can very clearly see what we're doing now and like what we're doing next. And I don't see the limit to the scaling laws. Like if you're just sort of thinking about the raw capability of the models and like how well you can condition them to reason over incre…”
Kevin Scott Mar 31, 2025 ▶ 8:31 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2030
Scott: 95% of net new code will be AI-generated within five years
“95% is going to be AI generated. I think very little is going to be line by line is going to be human written code.”
Kevin Scott Mar 31, 2025 ▶ 30:30 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Disclosure
Scott: Microsoft chose not to launch models more interesting than DeepSeek-R1
“We've had models more interesting than Deep Seek R-One that, like, we didn't even We chose not to even launch them.”
Kevin Scott Mar 31, 2025 ▶ 15:05 Kevin Scott, CTO @ Microsoft: An Evaluation of Deepseek and How We Underestimate the Chinese · 20VC with Harry Stebbings
Assertion Contradicted
Hulme: Microsoft acquired Inflection primarily for its 12,000 H100 GPU cluster
“I do not believe that Microsoft were buying the Pi model. I think Microsoft are GPU constrained, and we're buying a cluster of 12,000 H-one hundreds.”
Tom Hulme May 8, 2024 ▶ 49:13 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
Opinion
O'Driscoll: GitHub is now a trailing edge product
“And the fact that they've lost that connection with developers, that GitHub is now a trailing edge product, is to me, over the medium term, a pretty significant loss.”
Rory O'Driscoll Aug 20, 2026 ▶ 13:51 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Opinion
Frankel: Microsoft Has Done a "Crappy Job" With AI
“So I think Microsoft have done a crappy job of AI generally.”
David Frankel Aug 7, 2026 ▶ 1:04:43 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Prediction Not checkable as stated
Lemkin: Microsoft's enterprise AI deployment strategy will fail
“I think this is going to fail because I don't think there is enough talent To do what we want to do in the enterprise. The idea makes sense to on a spreadsheet. It makes sense. Sad is smarter than me, but I, my today, my experience is it's going to fail with a…”
Jason Lemkin Jul 9, 2026 ▶ 1:07:56 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
Opinion
O'Driscoll: Microsoft does not have an AI model worth a damn
“And in Microsoft case, I really wish I even had a model that was worth a damn, which I don't.”
Rory O'Driscoll May 14, 2026 ▶ 14:52 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Opinion
O'Driscoll: Microsoft leadership nailed OpenAI deal, but failed on shipping technology
“I think when all is said, and as I said before, on Microsoft's side, when all is said and done, the shareholders should award medals to Satya, The CFO and their GC and they should hire someone else to do their technology because they haven't shipped, right?”
Rory O'Driscoll Oct 23, 2025 ▶ 42:16 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Opinion
O'Driscoll: Microsoft enabled OpenAI just as IBM enabled Microsoft 30 years ago
“The role of IBM has been played by Microsoft. They set this Viper in motion, and they've allowed it to exist, and in one sense for a while it looked like Microsoft got a good deal because they got access to OpenAI's technology early on, and they got a little b…”
Rory O'Driscoll Oct 9, 2025 ▶ 7:58 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Opinion
O'Driscoll: $4T AI infrastructure investment requires impossible $800B annual profit
“Four, let's do four billion dollars. You want a 20% return on equity. You gotta be generating eight hundred billion of profit a year. That's a lot of profit when, you know, Facebook met, all these guys make a couple hundred billion a year, right? So you've got…”
Rory O'Driscoll Sep 4, 2025 ▶ 49:12 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Assertion Not checkable as stated
Chen: Surge AI has more daily working PhDs than Big Tech combined
“Like if you think of all the PhDs, even at Google or Meta or Microsoft, we have way more than all of them combined doing work for us in a single day.”
Edwin Chen Jul 21, 2025 ▶ 40:23 Surge CEO & Co-Founder, Edwin Chen: Scaling to $1BN+ in Revenue with NO Funding · 20VC with Harry Stebbings
Opinion
Lemkin: Microsoft has no leverage over OpenAI because AGI is imminent
“The reason I think they have no leverage is because I think that whatever AGI is, we're going to be there pretty soon.”
Jason Lemkin Jun 19, 2025 ▶ 42:14 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Prediction Not checkable as stated
O'Driscoll: OpenAI will declare AGI based on Microsoft contract negotiations
“It'll achieve open AGI whenever it suits Sam Altman in his negotiations with Microsoft over the open AGI term in that contract to declare it to be AGI. Because it's a meaningless, ill-defined term that will be used for economic leverage.”
Rory O'Driscoll May 29, 2025 ▶ 1:08:05 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
Opinion
Torres: Nobody is using Microsoft Copilot because the product doesn't work
“Copilot, everybody was like, they're just ahead making all the money first because people, the problem is people are, they just have so much hard time trusting someone, right? And so they're reaping the benefit of being early, But nobody's using the product, r…”
Elias Torres Mar 21, 2025 ▶ 13:34 Elias Torres, Co-Founder and CEO @ Agency: What No One Tells You About Selling Your Company · 20VC with Harry Stebbings
Opinion
Odoo's product is years ahead of Microsoft and SAP
“I think our product is years ahead of the competition. There is no way they can do what we do.”
Fabien Pinckaers Feb 12, 2025 ▶ 20:06 Fabien Pinckaers, CEO @Odoo: The Billionaire Founder Who Doesn’t Care About Money | E1259 · 20VC with Harry Stebbings
Opinion
SAP and Microsoft enterprise software is shitty, slow, and expensive
“On the market, you have two types of market. You have the large players, like SAP and Microsoft. They do several applications, but it's shitty, it's slow, it's expensive. And people are not happy using it.”
Fabien Pinckaers Feb 12, 2025 ▶ 40:41 Fabien Pinckaers, CEO @Odoo: The Billionaire Founder Who Doesn’t Care About Money | E1259 · 20VC with Harry Stebbings
Opinion
Pishevar: Steve Ballmer was a terrible CEO despite massive wealth
“Steve Ballmer. You know, the decade that he was CEO of Microsoft, Microsoft was completely just flat, right? And he's now richer than Bill Gates, right?”
Shervin Pishevar Jan 13, 2025 ▶ 1:11:21 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Disclosure
Dan Gill would pass on investing in OpenAI, Anthropic, and xAI
“I wouldn't invest in any of them. I think that the foundational models are trending towards commoditization and it's gonna be difficult to capture all of the gains relative to what, you know, Google, Google can capture and Microsoft can capture and others.”
Dan Gill Jan 8, 2025 ▶ 1:04:37 Dan Gill, CPO @Carvana: The Most Wild Story in Public Markets | E1243 · 20VC with Harry Stebbings
Disclosure
Jason Citron explains why Discord rejected Microsoft's acquisition offer
“Microsoft has been a really fantastic partner for us. And there certainly are things that we could have done together with them that we can't do independently, but ultimately it was about You know, controlling your own destiny, I suppose, and really seizing th…”
Jason Citron Nov 25, 2024 ▶ 30:31 Jason Citron, Co-Founder/CEO @Discord: The Untold Story Behind Scaling to 200M Users | E1230 · 20VC with Harry Stebbings
Assertion Partly supported
Microsoft Board Approved $1B for OpenAI Despite Having No Clear Product
“The very first OpenAI Microsoft deal was, you know, Satya and Kevin Scott brought to the Microsoft board. We want to put a billion dollars into the investment in this vehicle. From a five one C three that doesn't really have any particular plans at making its …”
Reid Hoffman Jun 10, 2024 ▶ 29:58 Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings
Disclosure
Reber: Selling Wunderlist to Microsoft felt like selling to the enemy
“When I sold Wanderlust, it felt like I'm selling my child to the enemy. I didn't want to get bought by Microsoft. I viewed Microsoft as the enemy, and it was just stupid.”
Christian Reber Feb 15, 2021 ▶ 21:50 20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction
Opinion
Reber: Microsoft screwed up its acquisitions of Yammer, Skype, and Wunderlist
“I think Microsoft has Screwed up multiple acquisitions like Yammer or Skype, and they promised me when we sold it that they will try their very best not to screw up Wunderlist, and I think they did.”
Christian Reber Feb 15, 2021 ▶ 10:23 20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction
Prediction Not checkable as stated
Reyes: Microsoft Will Win in AI Regardless of Which Model Succeeds
“The biggest thing that Microsoft has going for it is that infra. They own so many of these data centers. They're spending so much on build out. No matter what model runs on top of that, Microsoft is going to win.”
Eno Reyes Aug 29, 2026 ▶ 51:43 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Assertion Not checkable as stated
O'Driscoll: Anthropic and OpenAI exist only due to hyperscaler funding
“The only people capable of financing a state-of-the-art frontier model in the United States of America has been the hyperscalers themselves. The only reason Entropic and OpenAI exist is because Microsoft, Google, and Amazon gave them enough money to play becau…”
Rory O'Driscoll Aug 27, 2026 ▶ 10:06 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Opinion
O'Driscoll: Owning developers is 100% existential for Microsoft
“I don't think owning the developer is existential for AWS. I definitely don't think it's existential for Meta. It's a hundred percent existential over the medium term for Microsoft.”
Rory O'Driscoll Aug 20, 2026 ▶ 14:20 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Prediction Not checkable as stated
O'Driscoll: Microsoft will build a massive, lower-margin AI services business
“So summary, I think Microsoft will build a huge services business here if they want to, which also speaks to it won't be nearly as profitable as selling operating systems.”
Rory O'Driscoll Jul 9, 2026 ▶ 1:11:58 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Prediction Open · timeframe Jul 2027
O'Driscoll: AI capex spending will be stopped by demand, not supply
“This isn't, this spending isn't going to stop because the supply side says stop. Facebook aren't going to say stop. Google isn't going to say stop. Microsoft isn't going to say stop. Really, it boils down to the demand side. As long as, and enterprise customer…”
Rory O'Driscoll Jul 9, 2026 ▶ 41:39 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Opinion
Stebbings: Microsoft beats superior startup products through enterprise bundling
“Microsoft has built a business on doing 60 to five to 70% meh products, but with the power of bundling, beat the competitors.”
Harry Stebbings Jul 6, 2026 ▶ 40:39 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
Prediction Not checkable as stated
O'Driscoll: Anthropic Sales Force Will Resemble Oracle's Within 5 Years
“The entropic sale force in five years will look like the Oracle sales force, the Microsoft sale force, and the IBM sale force, 50 years ago”
Rory O'Driscoll Jun 11, 2026 ▶ 46:19 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Opinion
O'Driscoll: Partnering with OpenAI is no longer a sufficient AI strategy
“This was the end of the period where you could Fool yourself even slightly that your plan for your plan for AI is to partner with open AI. That's just not the answer anymore.”
Rory O'Driscoll Jun 11, 2026 ▶ 1:11:44 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Assertion Contradicted
O'Driscoll: Microsoft's revenue growth is flat without its AI initiatives
“Without the AI initiative, Microsoft is flat revenue.”
Rory O'Driscoll May 7, 2026 ▶ 0:41 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 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
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
Assertion Supported
Cahn: Microsoft walked away from two data centers in early 2025
“Microsoft walked away from two data centers and it sent a message to the market like, hey, we're not stepping up.”
David Cahn Oct 27, 2025 ▶ 23:26 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Assertion Not checkable as stated
Calacanis: OpenAI capital requirements are 100x Microsoft's initial high-end estimates
“OpenAI needed much more capital than they thought when they started. Microsoft bailed them out in buying 49% of the company. Now they need much more capital than Microsoft thought. Probably two orders of magnitude more than Microsoft's, ah, you know, high-end …”
Jason Lemkin Oct 23, 2025 ▶ 42:50 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Insight
O'Driscoll: OpenAI and Nvidia are repeating Microsoft and Intel's 90s playbook
“Fast forward to today, the company that's dominating everything is OpenAI. They're the Microsoft of today. They have the consumers. They have the eyeballs, right? They're building this new monopoly, and the equivalent of Intel is now Nvidia.”
Rory O'Driscoll Oct 9, 2025 ▶ 6:57 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Opinion
Ross: Amazon lacks AI DNA compared to Google, Meta, and Microsoft
“Amazon, I think doesn't have AI DNA. And they, like, if you compare them, so you didn't mention Meta, right? But Meta and Google always had the AI DNA, and Microsoft bought it with OpenAI, but that bought them time. Amazon still doesn't have that DNA, but they…”
Jonathan Ross Sep 29, 2025 ▶ 1:29:14 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Ross: Microsoft withheld Azure GPUs because internal usage made more money
“Microsoft in one quarter deployed a bunch of GPUs, and then announced that they weren't going to make them available in Azure because they made more money using them themselves than renting them out.”
Jonathan Ross Sep 29, 2025 ▶ 2:01 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
Assertion Contradicted
Taneja: Microsoft generated the highest multiple return among OpenAI investors
“Taking that bet was hugely, hugely valuable for Microsoft. I think, and if you look at the return, by the way, if they put in twenty billion, they are the ones who have the highest multiple return as well. So it was a great investment on a financial basis and …”
Hemant Taneja Sep 22, 2025 ▶ 39:43 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 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
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
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
Prediction Open · timeframe Aug 2028
Lemkin: CoreWeave will show signs of an AI slowdown before hyperscalers
“Core weave, if core weave struggles, if it can't service its debt, if it can't raise more debt through this weird through, through the hyperscalers guaranteeing it, that's where we'll see, even if there's just a bump in this cycle, that's not that, that doesn'…”
Jason Lemkin Aug 21, 2025 ▶ 58:17 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Insight
Fanton: Playing Chess And Guitar Is A Strong Heuristic For Exceptional PMs
“If you know how to play chess and play guitar, your will be a great PM because it's the creative side together with analytical side. Chess is a great proxy for analytical capability and playing instruments is an amazing proxy. For creativity.”
Fernando Fanton Jul 27, 2025 ▶ 18:07 20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product
Prediction Not checkable as stated
O'Driscoll: AI model providers will eventually squeeze out software wrappers
“At some point when things get tougher, just like Microsoft did in the nineties, the platform provider starts to grind everyone's balls. And, you know, take more of the share away. There ain't 10 versions of PowerPoint in 20, 25.”
Rory O'Driscoll Jul 24, 2025 ▶ 17:45 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
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