The Ledger

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why aren't all 49 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

Prediction Didn’t hold up
Mostaque: Only 5 or 6 foundation model companies will exist in 3-5 years
“I think that there's only going to be five or six foundation model companies in the world in three years, five years. I think it's going to be us, Nvidia, Google, Microsoft OpenAI, and Meta and Apple probably are the ones that train these models.”
Emad Mostaque Nov 24, 2023 ▶ 0:55 The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085 · 20VC with Harry Stebbings
Assertion Partly supported
Claure: Pitching Steve Jobs Created the Mobile Phone Trade-In Model
“So back then, I used to own Brightstar. And I had an idea of how could Apple actually double their sales. And after many emails to Steve Jobs, which he wrote me back, no interest. One day he got tired of everybody pinging him that he had to meet me. So he agre…”
Marcelo Claure Jul 31, 2023 ▶ 59:20 Marcelo Claure & Shu Nyatta: LATAM's New $500M Growth Fund; Investing Billions at SoftBank | E1042 · 20VC with Harry Stebbings
Assertion Supported
Steve Jobs told Dropbox it was 'a feature, not a product' in 2009
“He was like, well, you guys are a feature, not a product. And now we're gonna have to like compete with you and kill you and you don't have distribution and dah, dah, dah, dah, dah.”
Drew Houston Oct 18, 2022 ▶ 49:04 Dropbox CEO Drew Houston: How to Pick a Co-Founder; Steve Jobs' Attempt to Buy Dropbox | 20VC #938 · 20VC with Harry Stebbings
Assertion Supported
Fadell: iPod's original strategy was driving Mac sales, which failed
“We're going to sell the iPod. It's going to be so awesome that people will buy Macs so they could use their iPod. We're going to sell more Macs because they're going to need to buy one to use an iPod that they're going to have to have. Well, guess what? The fi…”
Tony Fadell Jun 6, 2022 ▶ 36:40 Tony Fadell: Product Marketing Lessons I Learned from Steve Jobs | 20VC #884 · 20VC with Harry Stebbings
Prediction Held up
Uretsky: Apple will never match iPhone scale with another product category
“So when I read online about, you know, all of these different pundits talking about, you know, what's Apple's next big thing, my answer is there isn't one, because it has nothing to do with Apple. It has to do with the market. If you can't Find another thing t…”
Moisey Uretsky Oct 14, 2016 ▶ 10:20 20VC: How You Can Learn To Be A Great Business Leader & Why All Successful Business Must Be Loved or Needed with Moisey Uretsky, Founder @ Digital Ocean
Assertion Contradicted
Weitzman: AirPods made more revenue than Spotify and audio competitors combined
“And by the way, AirPods made more money Then Spotify and almost every other audio company put together every single year for the last seven years.”
Cliff Weitzman May 9, 2026 ▶ 1:42:30 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
Weitzman: Speechify's early hires from Apple and Snapchat failed within three months
“We had two people that we hired from Apple and Snapchat, like very legit people. And they messed up the culture of the company. They would leave at 5:30 p.m. They like didn't live and breathe the company. And in the end, both of them quit after three months.”
Cliff Weitzman May 9, 2026 ▶ 1:03:06 Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries · 20VC with Harry Stebbings
Assertion Supported
Masad: Replit has been stuck in Apple App Store review for months
“Replit has been on the App Store since twenty-twenty-two doing exactly the same thing, allowing people to generate or write code. And running it in a browser window. Suddenly they're saying that we are you know, we're not complying with their guidelines. And w…”
Amjad Masad Apr 25, 2026 ▶ 38:56 Replit CEO: Why the SaaS Apocalypse is Justified & Why Coding Models are Plateauing | Amjad Masad · 20VC with Harry Stebbings
Prediction Held up
Seibert: On-device iPhone LLMs will make OpenAI obsolete within five years
“I bet Apple can and will, and so if you project forward five years, if they get to the point where they can run a sufficiently large LLM on your iPhone, then OpenAI is out of the picture. Don't even need to hit their servers. It's just on your phone.”
Jeff Seibert Nov 24, 2023 ▶ 23:48 The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085 · 20VC with Harry Stebbings
Assertion Supported
DHH: Zoom's Hidden Web Server Forced Apple to Issue Emergency Patch
“All the shit that they've done that's kind of on the sly, whether it was last year when they installed this uninstallable web server, just because they wanted to save a click, right? And then Apple all of a sudden had to release this emergency fix to remove th…”
David Heinemeier Hansson Apr 14, 2020 ▶ 45:00 20VC: Basecamp Founder David Heinemeier Hansson on Why It Is The Biggest BS To Chase Being A Unicorn, His Relationship to Wealth and Status and Why Now More Than Ever It Is A Myth Entrepreneurs Have To Raise VC
Assertion Supported
Loftus: Big Tech Buyer Softening Has Kept Startup Acquisition Prices Moderate
“So I haven't seen a ton of price increase, but I do think that's because in my view, even though you've seen new entrants into the market, There's been softening at the other end of the market from the Google, Facebook, Apple, Amazon end.”
James Loftus Mar 26, 2018 ▶ 10:10 20VC: How Great VCs Handle Themselves In An M&A Process, Why M&A Has Become The Primary Method of Exit & How The Best M&A Teams Operationalise Their Process with James Loftus, Corporate Development Lead @ Square
Prediction Didn’t hold up
Chad Byers Predicts Facebook or Amazon Will Hit $1 Trillion First
“So I think it's Facebook. You know, my second answer, although this is kind of cheating, would probably be Amazon. So Facebook or Amazon, I don't think it's Apple. I don't think it's Google. I think it's going to be one of those two.”
Chad Byers Aug 24, 2016 ▶ 21:25 20VC: Why Raising A Fund Is Like Raising A $25m Seed Round with No Product & Why Not All LP Money Is Equal with Chad Byers, General Partner @ Susa Ventures
Prediction Held up
Pakman: Apple Music will reach only 30-50M paid subscribers in 2 years
“I think there'll be a sustainable long-term digital music streaming service, but I don't think they'll get much more than, you know, I'm thinking sort of 30 to fifty million paying subscribers over the next two years, so I think my prediction is that they'll f…”
David Pakman Jul 15, 2015 ▶ 16:55 20 VC 055: David Pakman @ Venrock on The Future Of The Music Industry
Assertion Supported
O'Driscoll: 400 employees have left Apple to join OpenAI
“400 people from Apple have gone to move to OpenAI”
Rory O'Driscoll Jul 16, 2026 ▶ 4:00 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Apple pays Google $1B for Gemini while receiving $20B for search
“I think, to some extent, they're giving in the sense that they're paying Google a billion dollars to use their model as the default model, but reminder, Google pays them, I think, 12 or 20, I used to know the number, twenty billion dollars to be the default se…”
Rory O'Driscoll Jun 11, 2026 ▶ 21:46 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
Prediction Held up
Lemkin: Elon Musk or xAI Will Sue Apple
“He's incensed, and he's got a lot of money in XAI. I mean, he has, he's the richest man in the world, but he doesn't have unlimited capital, so I think it happens.”
Jason Lemkin Aug 14, 2025 ▶ 1:33:24 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
Prediction Didn’t hold up
Lemkin: Apple will announce US iPhone assembly operations within the year
“I think, listen, I don't, I would have to do more analysis to see if, it's not possible, right? If it's close to impossible, but announcing it and beginning a process, you might have to do it. You just might have to do it. I'm going to go yes.”
Jason Lemkin Jun 19, 2025 ▶ 1:03:03 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: Tim Cook will not announce impossible US iPhone assembly operations
“I think politically it would be smart to announce it, even though it's impossible. I think Tim Cook is such a straight shooter that he just couldn't pull it off with a straight face because everyone was, no, it's absolutely bullshit.”
Rory O'Driscoll Jun 19, 2025 ▶ 1:03:22 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
Assertion Supported
Hoggett: Apple surpassed FTSE 100 market cap in summer 2020
“And in the summer of 2020, Apple was worth more than the FTSE 100 for the first time.”
Julia Hoggett Mar 28, 2025 ▶ 1:15 Julia Hoggett, CEO @ LSEG plc: The Myths and the Reality of The London Stock Exchange · 20VC with Harry Stebbings
Assertion Contradicted
Morin: Apple purchased 100,000 Trainium AI chips from Amazon
“Let's take Amazon, for instance, with Tranium. Apple just came and said, Hey, we're going to buy a 100,000 of them.”
Steeve Morin Feb 24, 2025 ▶ 40:30 Steeve Morin: Why Google Will Win the AI Arms Race & OpenAI Will Not | E1262 · 20VC with Harry Stebbings
Prediction Held up
Sim: Apple edge AI developments will not generate meaningful revenue in 2024
“My short would probably be, I mean, just what everyone's looking at now is just Apple right now. I think Apple, You know, you've got an iPhone growth issue over there at Apple, but the one thing that gets me excited about Apple is the idea of machine learning …”
Ed Sim Jan 10, 2024 ▶ 1:07:00 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Assertion Partly supported
Söderström: Spotify's streaming business model took Apple eight years to copy
“I think for Spotify, for example, when we started, it was the business model of streaming. That was the disruptive thing. The technology was you know, a bit of peer to peer and stuff, but it was a business model that took Apple eight years of collateral damage…”
Gustav Söderström Dec 20, 2023 ▶ 38:13 Roundtable #7: Spotify, Adobe and Linkedin on How AI Changes The Future of Product & Design | E1097 · 20VC with Harry Stebbings
Assertion Partly supported
Fadell: iPod wasn't a successful business until its third generation
“The iPod Was a critical success, but it didn't really turn into a successful business till the third generation. And the reason being was it didn't work with Windows based PCs. It only worked with Macs, which were a fraction of the market, less than a percent,…”
Tony Fadell Jun 6, 2022 ▶ 36:10 Tony Fadell: Product Marketing Lessons I Learned from Steve Jobs | 20VC #884 · 20VC with Harry Stebbings
Assertion Supported
Apple's original iPhone YouTube app only supported half of YouTube's content
“Apple built the first YouTube app on the iPhone, and they just kept doing it. They kept building the YouTube app, so we actually didn't control the YouTube experience on the iPhone, and over time, it had just fallen out of date. Apple developers couldn't keep …”
Shishir Mehrotra Sep 25, 2020 ▶ 17:09 20VC: The 4 Phases of Effective Decision-Making, The No 1 Quality of Good Decisions, How To Approach Effective OKR Setting, & How To Optimise and Improve Your Operating Cadence with Shishir Mehrotra, Founder & CEO @ Coda
Assertion Supported
Steve Jobs Had Product Leaders Run M&A to Prevent Deal Quotas
“Steve Jobs, who was still running the company at the time, had a pretty strong philosophy that if you have an M&A team who's being judged on how many deals a year they bring in, then you're going to be doing M&A just to do M&A. So what he did is he had the pro…”
Chad Richard Nov 22, 2017 ▶ 4:32 20VC: Why Strategic Investing Is Slow Motion M&A, Why Valuation Is The Hardest Element of M&A & What Determines Between Cash vs Stock Deals with Chad Richard, SVP of Business & Corporate Development @ Yelp
Assertion Supported
Sideman: Apple ended its 30% cut on peer-to-peer user currency transfers
“Apple just changed their guidelines last month, so they don't take their 30% cut when a user passes currency to another user, and that's a big deal, and it was in reaction to feedback from consumers who want to do micropayments, and, you know, with cryptocurre…”
Adi Sideman Oct 27, 2017 ▶ 8:16 20VC: Why Decentralisation is Key For Digital Media Distribution, Why Gradual Decentralisation Is The Most Practical Approach and Why Incumbents Are The Biggest Barrier To The Rise of Crypto with Adi Sideman, Founder & CEO @ YouNow
Assertion Supported
NYC tech ecosystem lacks a mega-scale anchor company
“The negative of what's happened here in the past seven years is you haven't seen the true emergence of a destination company, right? We have incredible companies that are building incredible foundations here. Some have went, went public already. Some will go p…”
David Tisch Jan 11, 2016 ▶ 5:03 20 VC: David Tisch @ Box Group on The Future of Consumer Mobile, Developing Pattern Recognition and FOMO
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: Tim Cook will not step down as Apple CEO this year
“So it's their job, but there's no way it's this year. Unless it's a health issue, there's no way it's going to be this year.”
Jason Lemkin Oct 9, 2025 ▶ 1:27:56 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
Assertion Supported
Feldman: Tech giants achieved chip design success primarily through acquisitions
“Where there's been success, it has frequently been acquired. Apple got into the chip business through buying PA Semi. Amazon got into the chip business through acquiring Annapurna.”
Andrew Feldman Oct 6, 2025 ▶ 49:49 Cerebras CEO, Andrew Feldman on Why Raise $1BN and Delay the IPO & Why NVIDIA’s Worried About Growth · 20VC with Harry Stebbings
Assertion Partly supported
Alex Schultz: Meta spends less on marketing than its tech peers
“Apart from Apple, whose marketing is paid for by the carriers, we have the lowest percentage of operating income that we spend on the stuff, the media that we disclose in the XK”
Alex Schultz Sep 5, 2025 ▶ 1:01:21 20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader
Assertion Contradicted
Lemkin: iPhone and App Store drive 75% of Apple revenue
“25% of the revenue is from the App Store, 40% of its profit, right? And 75% of its revenue is iPhone and App Store.”
Jason Lemkin Jul 31, 2025 ▶ 55:38 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
Assertion Contradicted
Moubeche: Apple AirPods generate more revenue than any software company
“I love this graph where you see, like AirPods revenue versus any software company, and you see that just the AirPods are making, like, more revenue than any software currently on the market.”
Guillaume Moubeche Dec 13, 2024 ▶ 1:09:29 Guillaume Moubeche, lempire Founder: Bootsrapping to $30M ARR Through Content & Brand | E1238 · 20VC with Harry Stebbings
Assertion Supported
Arison: Ads represent 15% of Grindr revenue without app store fees
“Ads are about 15% of our revenue in, in total, but obviously on a margin basis, they're even higher percentage, because it's a very profitable part of the business, and we don't have to pay the Apple and Google taxes on that revenue.”
George Arison Dec 4, 2024 ▶ 36:43 George Arison, Grindr CEO: How Grindr Built a Free Flow Cash Machine | E1234 · 20VC with Harry Stebbings
Assertion Supported
Quattrone: Netscape's 1995 IPO was Morgan Stanley's biggest since Apple in 1980
“And there were a couple of phases to this, you know, Netscape, Netscape came public in 1995. And it was literally the most popular IPO at Morgan Stanley since Apple in 1980.”
Frank Quattrone Mar 1, 2024 ▶ 12:19 Frank Quattrone: Lessons from 650 M&A Deals Worth Over $1TRN & Taking Amazon and Cisco Public| E1121 · 20VC with Harry Stebbings
Assertion Partly supported
Hugo Barra: Lobby 7's technology powered Apple's early Siri assistant
“Our company ran out of money, and we ended up getting, you know, actually hired by a big software company called Nuance, which was actually good because it actually gave us the runway to build and prove that vision that we had, and in the end our tech became t…”
Hugo Barra Nov 9, 2022 ▶ 2:39 Hugo Barra: How I Built Hardware for Android, Xiaomi, and Oculus | 20VC #947 · 20VC with Harry Stebbings
Assertion Partly supported
Eric Schmidt used Apple board seat to prepare Google for mobile
“Now, back then, and this is kind of incredible, Google CEO Eric Schmidt sat on Apple's board of directors, which is a crazy thing to think these days, and it was basically like having a crystal ball. You know, Eric knew that over multiple generations, you know…”
Hugo Barra Nov 9, 2022 ▶ 3:26 Hugo Barra: How I Built Hardware for Android, Xiaomi, and Oculus | 20VC #947 · 20VC with Harry Stebbings
Assertion Partly supported
Bill Campbell coached Steve Jobs and Google founders simultaneously
“They call them the coach, the trillion dollar coach, because he would, as you know, coach Steve Jobs, who no one in the world thought was coachable, and then he would coach Larry Page and Eric Schmidt and Sergey at Google on two of the most important companies…”
Emil Michael Oct 25, 2022 ▶ 3:22 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Assertion Supported
Fadell: Apple scrapped two and a half iPhone versions before shipping
“That was what we did on the iPhone. We had two and a half versions really of the iPhone before it shipped, because we kept revving it, getting to a certain point, throwing it away, trying again, getting a certain point, throwing it away because we make constra…”
Tony Fadell Jun 6, 2022 ▶ 44:05 Tony Fadell: Product Marketing Lessons I Learned from Steve Jobs | 20VC #884 · 20VC with Harry Stebbings
Assertion Supported
Steve Jobs offered to acquire iLike for $50 million in 2008
“Basically, we had raised money two years earlier for fifty million dollars, and he offered to acquire the company Four or fifty million dollars, so basically no change in valuation since our pre-launch, you know, fundraise,”
Ali Partovi Jan 21, 2022 ▶ 20:13 20VC: How I Lost a $125M Deal with Yahoo by Being Too Honest, The M&A Meeting with Steve Jobs That Did Not Go Well and How U2's Bono Saved The Day For One Tech Startup with Ali Partovi, CEO @ Neo
Assertion Supported
Shear: Apple requires high-fidelity demos to secure internal project funding
“The way you pitch for resources for a new Apple product. A lot of the time is a full fidelity demo. And you actually make a full touch and feel high fidelity demo of the experience that the customer is going to have. And then the vice president of the area who…”
Emmett Shear Feb 21, 2020 ▶ 20:43 20VC: Twitch Founder & CEO Emmett Shear on When To Persist vs When To Give Up For Entrepreneurs, The Fundamental Tension When Scaling Orgs and How To Optimise Them & How The Role of CEO Fundamentally Changes with Scale
Assertion Partly supported
Apple's M&A Strategy Focused Entirely on Talent Over Revenue Streams
“We were very much focused on finding great teams. It was never about acquiring revenue streams. It was finding great people who wanted to come to Cupertino.”
Chad Richard Nov 22, 2017 ▶ 5:13 20VC: Why Strategic Investing Is Slow Motion M&A, Why Valuation Is The Hardest Element of M&A & What Determines Between Cash vs Stock Deals with Chad Richard, SVP of Business & Corporate Development @ Yelp
Assertion Supported
Apple asked Headspace to offer free SOS meditations on Apple Watch
“When Apple released the Apple watch, they came to us and asked us if we would consider putting our SOS meditations, you know, these short form two minute meditations for when you've, you're having some kind of crisis and just really need to sort of very quickl…”
Sean Brecker Aug 26, 2016 ▶ 13:20 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
Assertion Partly supported
O'Driscoll: Apple generates $2.6M revenue per employee, Google generates $2.1M
“Apple's about 2.6 million revenue per employee. You know, Google is 2.1.”
Rory O'Driscoll Mar 5, 2026 ▶ 59:49 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: ChatGPT was Apple's most downloaded app in 2025
“2025, the most down, and I checked, was the most downloaded app on Apple was ChatGPT.”
Rory O'Driscoll Dec 18, 2025 ▶ 15:08 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
Assertion Partly supported
Hommels: US heart disease spending rivals Apple's total global revenue
“That the pay, the sum of what the US spends on heart diseases and medication, all that kind of stuff in the US is, is in the vicinity of Apple's revenue worldwide.”
Klaus Hommels Nov 27, 2024 ▶ 1:10:21 Klaus Hommels: Why "Portfolios are Merely a Construct to Make LPs Happy"? | E1231 · 20VC with Harry Stebbings
Assertion Supported
Lanzone: Ask Jeeves was called the 'Apple of search' during turnaround
“We were later called the apple of search, believe it or not, by people in the search industry and just being really proud of that turnaround and what we were able to accomplish there.”
Jim Lanzone Jul 29, 2022 ▶ 4:33 Yahoo CEO Jim Lanzone: The Yahoo Turnaround Plan | 20VC #911 · 20VC with Harry Stebbings
Assertion Supported
Kyle Hill: Unpaid caregiving reaches $470B annually, matching Apple's market cap
“Unpaid caregiving services is four hundred seventy billion dollars a year, which is roughly equal the value of Apple.”
Kyle Hill Jul 15, 2016 ▶ 20:51 20VC: Why Every Employee Should Re-Apply For Their Job Every Year & The Strategies To Prepare For A Successful Fundraise with Kyle Hill, Founder & CEO @ HomeHero
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