The Ledger

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why aren't all 65 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

Opinion
Collison: Stablecoins are already the best option for cross-border payments
“Two places that we're seeing tons of interesting stuff is one, any kind of cross-border use case, where if you want to send money to a hundred countries, it's already the case that stablecoin's a much better way to do that than anything else. And that's where …”
John Collison Apr 21, 2026 ▶ 1:20:44 The economics and trends of the restaurant industry, with Tony Xu of DoorDash
Disclosure
Collison: Stripe is building Tempo for scalable AI agent crypto payments
“The second, and this is where Tempo, our new initiative, That you guys were nice enough to work with us on is coming in is very scalable crypto payments, and obviously agents is what we have in mind as we're developing Tempo, where, you know, if you want to pa…”
John Collison Apr 21, 2026 ▶ 1:21:03 The economics and trends of the restaurant industry, with Tony Xu of DoorDash
Opinion
Taylor: Coding agent success doesn't translate to broad knowledge work
“And so it's not like impossible for an agent to use those things, but the idea that you can like straight line from coding agents to writing the Stripe annual letter, I don't totally buy.”
Bret Taylor Mar 10, 2026 ▶ 3:25 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Insight
Taylor: Hierarchical multi-agent architectures are elegant on whiteboards but nonsensical
“I feel like this view of a multi-agent world was you have all these agents that do tasks that are fraud detection. You know, another one over here for, you know, personalization, and then you make a super agent, it does all these things, and it looks really go…”
Bret Taylor Mar 10, 2026 ▶ 10:23 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Assertion Not checkable as stated
Collison: High-agency, non-expert engineers are ascendant at Stripe thanks to AI
“High work ethic people. Who maybe weren't the best engineers you know, previously or now, those people are massively ascendant, as far as I can tell, because they suddenly got the exoskeleton, you know, and like, they always have the ideas as to what we should…”
John Collison Mar 10, 2026 ▶ 1:27:58 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Opinion
Collison: Critics calling vertical AI startups 'LLM wrappers' miss the point
“Some people have called these startups LLM wrappers. Those people are missing the point. The O-ring model in economics shows that in a process with interdependent tasks, the overall output or productivity is limited by the least effective component, not just i…”
John Collison Feb 24, 2026 ▶ 7:10 Stripe’s 2024 annual letter
Opinion
Stablecoin skeptics would not survive long at Stripe, says John Collison
“I don't think they would survive the company very long if someone's walking around like, I don't know, I don't think the stable going thing is going to be a thing.”
John Collison Nov 4, 2025 ▶ 1:09:58 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Prediction Not checkable as stated
Crypto transactions will soon be a large part of Stripe's business
“Crypto enabled transactions are going to be a very large part of the economy and just stripes business in the relatively near future.”
John Collison Nov 4, 2025 ▶ 1:07:21 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Opinion
Sundheim: Premier private companies like Stripe should not go public
“I mean, if I ran a private company like Stripe, I wouldn't go public.”
Dan Sundheim Oct 22, 2025 ▶ 1:28:58 Dan Sundheim of D1 Capital on the art of public market investing
Opinion
Levels tells Collison: Stripe's API grew overly complicated after COVID
“I think it wasn't going well after COVID. There was a few years where things were getting, the API was getting more and more complicated. We all complained about it. There was every, it felt like it was being run by engineers, not by people who actually use St…”
Pieter Levels Jul 9, 2025 ▶ 19:35 A Cheeky Pint with serial entrepreneur Pieter Levels (@levelsio)
Assertion Not checkable as stated
Stripe processes $1.4 trillion in 2024 payment volume, up 38%
“Businesses on Stripe generated 1.4 trillion in total payment volume in 2024, up 38% from the prior year and reaching a scale equivalent to around 1.3% of global GDP.”
John Collison Feb 24, 2026 ▶ 0:00 Stripe’s 2024 annual letter
Prediction Not publicly verifiable
Collison: 2025 AI agent startup launches on Stripe will eclipse 2024's 700+
“More than 700 AI agent startups launched on Stripe last year, a figure that we expect will be substantially eclipsed by the total in 2025.”
John Collison Feb 24, 2026 ▶ 9:01 Stripe’s 2024 annual letter
Assertion Not checkable as stated
Collison: Stripe reached $1.9T in volume in 2025, up 34%
“Last year, businesses running on Stripe generated 1.9 trillion in total volume, up 34% from 24, an equivalent to roughly 1.6% of global GDP.”
John Collison Feb 24, 2026 ▶ 0:17 Stripe’s 2025 annual letter
Assertion Not checkable as stated
Collison: Startups reaching $10M ARR in 3 months doubled in Stripe's 2025 cohort
“The number of companies reaching ten million in ARR within three months of launch was double that of the 24 cohort.”
John Collison Feb 24, 2026 ▶ 4:06 Stripe’s 2025 annual letter
Insight
Collison: Building for startups predicts future enterprise product requirements
“What the startups were interested in were often better product experiences, and so if the startups want stable coins or usage-based billing or what have you, we should build for those needs, not just because we'll have a good startup business, but the enterpri…”
John Collison Nov 18, 2025 ▶ 13:30 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Assertion Not publicly verifiable
Ricks: LillyDirect annualizes in billions as largest online prescription platform
“Today we'll annualize, you know, in the billions of dollars. I think it's the largest Prescription platform online in terms of revenue. We run it on Stripe, I think, and going north from here.”
Dave Ricks Nov 11, 2025 ▶ 1:44:11 Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
Prediction Not checkable as stated
Abrams: There will not be separate company blockchains for Stripe or JPMorgan
“There's not a world where there's like a JP Morgan chain and a Stripe chain and a Bank of America chain and there's like a thousand, you know, unique company, company blockchains. That's not going to happen.”
Zach Abrams Nov 4, 2025 ▶ 44:14 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Disclosure
Privy required the ability to support Stripe's competitors during M&A talks
“And this was a part of the conversations that we had at Privy when talking to Stripe about M&A, which was like, what are conditions under which we think we can be successful here? And I think one of them was the need to be able to work with competitive endeavo…”
Henri Stern Nov 4, 2025 ▶ 42:29 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Insight
Acquired startups that remain entirely independent create negative synergy, says Abrams
“If you totally stay independent and you don't do any form of integration, there is like, One plus one equals maybe two, but probably less than two. Almost certainly, like, definitionally, you are setting yourself up for less than two.”
Zach Abrams Nov 4, 2025 ▶ 1:06:04 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Insight
Stern: Bundling with Stripe and Bridge turns 10-year roadmaps into 2-year roadmaps
“There's deep value to bundles and to being able to layer our software with stablecoin orchestration, stablecoin issuance, with traditional fiat money movement and rails, with the networks that Stripe has built across like, you know, marketplaces and merchants.…”
Henri Stern Nov 4, 2025 ▶ 58:15 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Insight
Lütke: Tech industry is bad at partnerships due to prisoner's dilemma thinking
“Tech is extraordinarily bad at partnerships. It's and I mean, it, it's always treated as a prisoner's dilemma that at some point, someone in the company realizes defecting gives you five points on the map, and that sounds really, really good with the short-ter…”
Tobi Lütke Oct 6, 2025 ▶ 1:00:40 Tobi Lütke is still captivated by internet commerce, 20 years later
Assertion Not checkable as stated
Collison: Stripe is shipping 30 percent more code thanks to AI tooling
“I think at Stripe we, ah, we're, we found we're shipping 30% more code.”
John Collison Aug 29, 2025 ▶ 19:19 A conversation with Lovable CEO Anton Osika
Insight
Collison: AI agents indexing docs are the ideal interface for complex APIs
“As we add more functionality to it, just the right way to navigate this big product surface area is an AI that's read all the API docs for you.”
John Collison Apr 7, 2026 ▶ 56:06 The history and future of AI at Google, with Sundar Pichai
Disclosure
Collison: Stripe is building SSH access directly into developer accounts
“And of course, now we're building that because it's like much more relevant in the agentic world”
John Collison Mar 10, 2026 ▶ 12:49 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Assertion Not checkable as stated
Half of Fortune 100 and one-sixth of new Delaware corporations use Stripe
“From top corporate leaders, half of the Fortune 100 uses Stripe. To hyper-growth companies, we count 80% of the Forbes Cloud 178% of the Forbes AI-fifty as customers. To newly formed upstarts, one in six new Delaware corporations incorporates with Stripe Atlas…”
John Collison Feb 24, 2026 ▶ 1:47 Stripe’s 2024 annual letter
Assertion Supported
Collison: Cursor reached over $100M ARR in just three years
“Cursor, the AI-powered coding assistant, raced to over one hundred million dollars in recurring revenue in just three years.”
John Collison Feb 24, 2026 ▶ 6:37 Stripe’s 2024 annual letter
Assertion Not checkable as stated
Stripe's revenue and finance automation suite reaches $500M run rate
“Stripe's revenue and finance automation suite, with billing at its core, has now passed a five hundred million dollar revenue run rate.”
John Collison Feb 24, 2026 ▶ 1:26 Stripe’s 2024 annual letter
Assertion Not checkable as stated
Stripe-processed revenue is growing seven times faster than S&P 500
“In aggregate, the revenue that businesses process on Stripe is growing seven times faster than that of all companies in the S&P 500.”
John Collison Feb 24, 2026 ▶ 2:09 Stripe’s 2024 annual letter
Assertion Not checkable as stated
Collison: Stripe has seen over 92% of processed credit cards before
“When a credit card is used for a payment, there is a greater than 92% chance that Stripe has encountered the same card before.”
John Collison Feb 24, 2026 ▶ 14:22 Stripe’s 2024 annual letter
Assertion Supported
Collison: Stripe partnered with OpenAI for ChatGPT shopping experience
“And we partnered with OpenAI to power the first shopping experience inside ChatGPT.”
John Collison Feb 24, 2026 ▶ 23:18 Stripe’s 2025 annual letter
Assertion Not checkable as stated
Collison: Stripe-acquired Bridge saw stablecoin volume more than quadruple
“Bridge, the stablecoin orchestration platform we acquired, saw volume more than quadruple.”
John Collison Feb 24, 2026 ▶ 9:26 Stripe’s 2025 annual letter
Assertion Not checkable as stated
Collison: Microsoft routes more payment volume to Stripe after auth rate gains
“Between June and October, Stripe delivered a meaningful increase in authorization rates for Microsoft using a combination of adaptive acceptance, card account updater, network tokens, and more. As a result, Microsoft is now routing a larger share of its paymen…”
John Collison Feb 24, 2026 ▶ 16:12 Stripe’s 2025 annual letter
Assertion Not checkable as stated
Collison: Gamma's Indian revenue jumped 22% after adding UPI payments
“Gamma is a California-based AI platform used by seventy million people to create presentations. When they joined the first cohort of Stripe users to accept UPI payments in India, their Indian revenue jumped 22% in that very same month.”
John Collison Feb 24, 2026 ▶ 7:41 Stripe’s 2025 annual letter
Disclosure
Collison: Stripe Capital disbursed 45% more funds to 81,000+ businesses in 2025
“Last year, Stripe Capital distributed 45% more funds compared to twenty-twenty-four to more than 81,000 businesses.”
John Collison Feb 24, 2026 ▶ 13:47 Stripe’s 2025 annual letter
Disclosure
Stripe launches Machine Payments for agent API microtransactions via stablecoins
“We launched Machine Payments, a way for developers to charge agents directly for API calls, MCP usage, and HTTP requests using stablecoin microtransactions.”
John Collison Feb 24, 2026 ▶ 23:04 Stripe’s 2025 annual letter
Prediction Not checkable as stated
Collison: Stripe's revenue suite on track to hit $1B ARR
“Metronome joins our revenue suite, comprising Stripe billing, invoicing, tax, and more, Which is on track to hit an annual run rate of a billion dollars this year.”
John Collison Feb 24, 2026 ▶ 1:31 Stripe’s 2025 annual letter
Assertion Not checkable as stated
Collison: Stripe remained robustly profitable throughout 2025
“Stripe remained robustly profitable in 25, allowing us to continue investing heavily in product development, with over 350 product updates over the last year, as well as acquisitions.”
John Collison Feb 24, 2026 ▶ 1:08 Stripe’s 2025 annual letter
Assertion Not checkable as stated
Collison: 30% of Stripe cross-border revenue is outside top 10 economies
“Of businesses on stride that earn most of their revenue internationally, 30% of that revenue comes from countries that are neither their home market nor one of the top 10 global economies.”
John Collison Feb 24, 2026 ▶ 7:07 Stripe’s 2025 annual letter
Disclosure
Collison: Stripe acquired Privy and Metronome
“Since our last update, we acquired Privy, which powers more than a hundred and ten million programmable wallets, and Metronome, which powers the complex usage-based billing models used by companies like OpenAI, Anthropic, Confluent, and NVIDIA.”
John Collison Feb 24, 2026 ▶ 1:19 Stripe’s 2025 annual letter
Assertion Not checkable as stated
Collison: Stripe powers over 5M businesses, 90% of Dow Jones
“Our programmable financial services now power more than five million businesses directly or via platforms, including all the top AI companies, many of the largest blue chip companies, 90% of the Dow Jones Industrial Average, most of the biggest tech companies,…”
John Collison Feb 24, 2026 ▶ 0:27 Stripe’s 2025 annual letter
Disclosure
Collison: Stripe is wiring merchant catalogs to be purchasable within AI copilots
“Part of what we're doing with this is making merchants product catalogs remotely discoverable and inventory and everything like that. And then remotely purchasable. Where you don't necessarily have to go through the whole flow on their site and everything like…”
John Collison Nov 18, 2025 ▶ 48:35 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Assertion Not checkable as stated
Collison: AI simplifies conversational commerce integrations for online merchants
“What's different here is, one, you have AI. So all the integrations for the merchant are much easier. It's much less of a lift than previous Times when things like that, this have been tried.”
John Collison Nov 18, 2025 ▶ 44:25 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Disclosure
Collison: Stripe is building a platform and open protocols for agentic commerce
“So we're building out this platform in agentic commerce where we have You know, some open source protocols like our agenda commerce protocol. We obviously have the regular Stripe products, you know, people are using us for, you know, and this, it's particularl…”
John Collison Nov 18, 2025 ▶ 50:03 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Disclosure
Collison: Stripe is training a payments foundation model on network data
“What we're now doing is training a payments foundation model where we're using all the data that we have in the Stripe network, and you have a much larger, more capable model taking into account. So anyway, we are trying to do exactly what you're saying.”
John Collison Nov 18, 2025 ▶ 37:30 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Assertion Not checkable as stated
Collison: Stripe's elevated online business creation never dropped post-lockdown
“There's a lot of charts of the shape of Stripe, I don't know if it's this way of Microsoft, where obviously March, 2020, you saw this discontinuity, right? Much more e-commerce activity happening, and we saw the rate of online business creation because, you kn…”
John Collison Nov 18, 2025 ▶ 42:54 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Insight
Collison: Infrastructure layers must remain unbundled to maximize market share
“If you're serious about all these layers of the stack, you can't bind them all together because just like there's no way you're going to get that much. You know, if Microsoft is serious about the office suite, they're going to have it run on Mac and Windows be…”
John Collison Nov 4, 2025 ▶ 43:32 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Opinion
Stripe needed Bridge and Privy to advance in crypto, says Collison
“At some level, Bridge and Privy make me much more bullish on M&A, because we had an idea going in, and Stripe was very much taking crypto and stablecoins seriously, and there's no way we would collectively be where we are now or there's no way Stripe would be …”
John Collison Nov 4, 2025 ▶ 1:01:47 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Assertion Not checkable as stated
John Collison admits Stripe was much more Patrick's idea than his own
“Stripe was much more his idea than mine.”
John Collison Oct 28, 2025 ▶ 1:11:31 Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
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