The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

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why aren't all 29 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 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 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
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
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
Prediction Held up
Rory O'Driscoll: Microsoft compute spending will grow 30% next year
“Is Microsoft going to increase another 30% next year? Is Antropic going to invest in compute? And right now, all those answers to those questions are yes.”
Rory O'Driscoll Nov 27, 2025 ▶ 19:49 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Microsoft was the only investor to give OpenAI $1B in 2019
“No one else was writing open AI, a billion dollar check in 2019. Microsoft did, and they got that return.”
Rory O'Driscoll Oct 30, 2025 ▶ 8:58 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: OpenAI finalizes restructuring deals with Microsoft and state regulators
“The big news today is OpenAI cut their deal. They cut their deal with Microsoft, and they cut their deal with the attorneys general, the plural of attorney general of Delaware and California, which means they have been able to implement their restructuring, wh…”
Rory O'Driscoll Oct 30, 2025 ▶ 1:31 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Microsoft Achieved a 10x Return on its $13B OpenAI Investment
“They put in thirteen million, thirteen billion dollars. They got a 10 X on their money as of today.”
Rory O'Driscoll Oct 30, 2025 ▶ 5:52 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: OpenAI Will Buy Compute From Oracle If Cheaper Than Microsoft
“Do I think the Oracle will book a fair amount of cloud compute from OpenAI? Absolutely. Maybe not three hundred billion, but if he's willing to provide it at a lower price than Microsoft, my guess is those fine people at OpenAI will take it.”
Rory O’Driscoll Sep 18, 2025 ▶ 52:22 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Assertion Supported
Quattrone: Salesforce submitted higher unsolicited bids during LinkedIn's exclusivity window with Microsoft
“So they went into like a 30 day exclusivity to try to get to definitive agreement. And during that period, Salesforce lobbed in Several offers that were higher. And that meant that towards the end of that period, we had to inform Microsoft, Hey, your deal is n…”
Frank Quattrone Mar 1, 2024 ▶ 35:04 Frank Quattrone: Lessons from 650 M&A Deals Worth Over $1TRN & Taking Amazon and Cisco Public| E1121 · 20VC with Harry Stebbings
Assertion Supported
Quattrone: Microsoft and Salesforce submitted nearly identical bids at every stage for LinkedIn
“With LinkedIn, we had interest from several parties, but it really kind of came down to Microsoft and Salesforce. And I've never seen companies bid privately and come up with such close prices on every stage Like, 151 151 162 163. It was very, very close, and …”
Frank Quattrone Mar 1, 2024 ▶ 33:36 Frank Quattrone: Lessons from 650 M&A Deals Worth Over $1TRN & Taking Amazon and Cisco Public| E1121 · 20VC with Harry Stebbings
Prediction Held up
Wunderlist will become Microsoft's core task layer and spread its startup culture
“Ah, so for me and Wunderlist, it is integrate deeply into, to Microsoft, be the layer that connects things in terms of tasks, things you need to get done, and continue to both learn from one of the largest, most important technology organizations ever, but als…”
Chad Fowler Oct 9, 2015 ▶ 24:15 FF 016: Chad Fowler, CTO @ Wunderlist, App Of The Year 2013
Prediction Held up
Mignano: Incumbent tech companies will constrain employee token spend budgets
“There's too many employees at a Salesforce or I don't know, a Microsoft such that every employee can just have an unlimited token spend budget. So I think we're going to see a lot of those companies start to constrain their spends.”
Mike Mignano Jul 6, 2026 ▶ 22:47 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
Assertion Supported
Green: Apple spends far less on AI CapEx than tech peers
“And, you know, like Apple's spending very little right now, you know, and those other three or four companies are spending insane amounts of money.”
Mitchell Green Mar 7, 2026 ▶ 8:41 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Prediction Held up
Lemkin: OpenAI and Microsoft will settle antitrust tensions privately
“I don't think Microsoft wants to be sued by any trust. So I think it's going to get worked out.”
Jason Lemkin Jun 26, 2025 ▶ 1:08:53 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Microsoft generates $350 million in cash daily
“Microsoft is throwing off three hundred and fifty million in cash a day.”
Harry Stebbings May 8, 2024 ▶ 54:50 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
Prediction Held up
Howie Liu: Microsoft Copilot Will Drive Significant ARPU Growth Across Office
“When you think about like Microsoft's co-pilot offering, it's going to add significant ARPU to every single seat of office, which is a massive install base, right?”
Howie Liu Aug 25, 2023 ▶ 21:58 Howie Liu: Decoding Airtable's $11B Valuation; The Impending AI Revolution in Enterprise | E1053 · 20VC with Harry Stebbings
Assertion Supported
Partovi: Microsoft earnings grew fantastically under Steve Ballmer's CEO tenure
“The Steve years were not great for Microsoft's stock price. They were fantastic for Microsoft's earnings and earnings growth.”
Hadi Partovi Dec 16, 2022 ▶ 8:24 Hadi Partovi: How I Became an Advisor to Mark Zuckerberg; Lessons from Steve Ballmer | 20VC #961 · 20VC with Harry Stebbings
Assertion Supported
Microsoft offered Tellme Networks an acquisition term sheet for $800M
“By the end of the weekend, three days later, I had a term sheet for seven hundred sixty million dollars. Plus the cash and imbalances. So just about eight hundred million dollars.”
Emil Michael Oct 25, 2022 ▶ 9:17 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Assertion Supported
Microsoft is aggressively gaining market share in enterprise public cloud
“They are several years into this transition and as Microsoft generally does, they're doing a great job of being a fast follower. And are very aggressively gaining share and making strides on the enterprise segment of public cloud specifically.”
Byron Deeter Jul 8, 2019 ▶ 8:13 20VC: Bessemer's Byron Deeter On Lessons From Investing in 14 $Bn Companies, What The Heck Is Going On In Cloud Today and Why Cloud IPO Floodgates Are About To Burst Open
Assertion Supported
Microsoft bought Nuance for $20B+ and competed with Abridge
“And the first big competitor for us was Microsoft. They had bought a company called Nuance for 20 some billion some years ago, and they had a product in our category and we still compete with them in the marketplace.”
Shiv Rao May 16, 2026 ▶ 34:04 The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Microsoft's capital expenditure has reached 25% of its revenue
“Microsoft CapEx as a percentage of revenue has crept up to 25%.”
Rory O'Driscoll Aug 21, 2025 ▶ 1:10:34 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Microsoft Laid Off 3% of Its Workforce
“Microsoft laid off three percent of their company today.”
Jason Lemkin May 15, 2025 ▶ 0:10 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Assertion Supported
Wood: FAANGs, Microsoft, and Nvidia made up nearly 50% of Nasdaq 100 in 2021
“Last year the market reached all-time highs in twenty-twenty-one as we were selling off, and it was the Fangs, it was Microsoft, it was Nvidia, and those, if you look at the Nasdaq 100, account for, account ed at that time, for nearly 50% of that index”
Cathie Wood Nov 14, 2022 ▶ 18:21 Cathie Wood: Elon & Twitter; Why Facebook is a Value Stock Now; ARK's Performance | 20VC #949 · 20VC with Harry Stebbings
Assertion Supported
Quarles: OpenTable Ran on an Old Microsoft On-Premises Database
“When I got into the company, we were at a point at which the software that we had inside the restaurant was an old Microsoft on-prem distributed database, like not in the cloud.”
Krista Quarles Jul 29, 2021 ▶ 12:27 20VC: A Masterclass in Leadership and Scaling Companies: The Decisions only the CEO Can Make, The Secret To Talent Acquisition and Retention and How To Find The Unscalable Things that are Fundamental To Scale with Christa Quarles, CEO @ Corel Corporation
Assertion Supported
Hartz: Microsoft and Amazon both IPO'd at $500M valuations
“If you look back at Microsoft in the 19 eighties or Amazon in the 19 nineties, one would maybe not recall that they went public at a five hundred million dollar valuation each”
Kevin Hartz Aug 31, 2020 ▶ 10:49 20VC: SPACs. What Are They? Why Now? How Do They Change The Venture Landscape? Are They Better Than IPOs & Direct Listings? How Should Founders Think About Them? Kevin Hartz & Troy Steckenrider @ A*
Assertion Supported
Microsoft acquired calendar app Sunrise.am for $100 million
“Sunrise.am, which was recently acquired for a hundred million by Microsoft.”
Harry Stebbings Mar 12, 2015 ▶ 0:27 20 VC 019: Funding the Future with James Wise of Balderton Capital
Assertion Supported
Buchheit: Microsoft's first product targeted only a few thousand potential customers
“Microsoft's first product was Altair Basic, which was a little basic interpreter for, or compiler for this computer called the Altair that had probably several hundred or maybe thousand possible customers.”
Paul Buchheit Nov 1, 2017 ▶ 6:31 20VC: Y Combinator's Paul Buchheit on Creating Gmail Version 1.0 & Leadership Lessons from Working With Zuckerberg and Larry Paige
Assertion Supported
Ver Ploeg: Microsoft went public at a sub-$1B market cap
“I mean, people like to talk about how when Microsoft went public, it was a sub one billion dollar market cap company.”
Eric Ver Ploeg Sep 9, 2015 ▶ 18:44 20 VC 070: Do Investors in California Outperform The Rest of The World with Eric ver Ploeg @ Recursive Capital
Assertion Supported
Microsoft Acquired Accompli for $200 Million in 2014
“Prior to Microsoft, Javier co-founded Accompli, the mobile personal information manager acquired by Microsoft for two hundred million dollars in 2014.”
Harry Stebbings Sep 6, 2015 ▶ 0:13 FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft
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