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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
CHEEKY PINT Assertion Supported
Collison: Sportsbooks take ~10% whereas prediction markets take ~1%
“The rate for sports betting companies is around 10%, and the order of magnitude for prediction markets is, you know, one percent or a few points.”
John Collison Mar 17, 2026 ▶ 56:05 Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
CHEEKY PINT Assertion Contradicted
Collison: Mainstream AI chat interfaces still lack persistent memory in 2026
“Still in twenty-twenty-six, if you open a new Gemini chat, or if you open a new ChatGPG chat, it's basically a blank slate. There's no memory.”
John Collison Mar 10, 2026 ▶ 1:25 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT 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
Collison: AI agents expose the lack of APIs for SaaS dashboard switches
“It turns out there's a lot of switches in the dashboard. Yeah. You know, there's no API for, and we are all as an industry collectively discovering that.”
John Collison Mar 10, 2026 ▶ 15:18 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT Assertion Supported
Collison: Lovable hit $17M ARR in 3 months, Bolt $20M ARR in 2 months
“We're also seeing the likes of Lovable, which hit seventeen million dollars ARR in just three months, Bolt, achieving twenty million ARR in two months, and Kodo, radically lower the barrier for turning software ideas into working applications.”
John Collison Feb 24, 2026 ▶ 6:43 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Open · timeframe Mar 2025
Collison: 60% of US small businesses use vertical SaaS platforms
“Today, 60% of all small businesses in America use vertical SaaS platforms to help run their business.”
John Collison Feb 24, 2026 ▶ 9:54 Stripe’s 2024 annual letter
CHEEKY PINT 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
CHEEKY PINT Assertion Supported
Collison: SpaceX uses Bridge for Starlink fund repatriation in emerging markets
“SpaceX uses Bridge to repatriate funds from Starlink sales in Argentina, Nigeria, and other markets.”
John Collison Feb 24, 2026 ▶ 17:23 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: Stablecoin volumes doubled year-over-year as active wallets hit 40M
“Stablecoin transaction volumes more than doubled between Q four, 20, 23 and Q four, 20, 24. And the number of monthly active stablecoin wallets has now reached forty million.”
John Collison Feb 24, 2026 ▶ 18:45 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: An estimated 99% of stablecoin balances are USD-based
“We further note with interest that despite regulatory uncertainty in the United States, early stablecoin adoption has shown a notable US dollar preference, with an estimated 99% of stablecoin balances being USD-based.”
John Collison Feb 24, 2026 ▶ 20:22 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: US productivity reached $104/hr versus $85/hr in Europe
“While the economies of the US and Europe were similarly productive in 1990, there has since been a stark divergence, with US productivity per hour works reaching 104 dollars, as compared with a plateau of something closer to 85 dollars per hour in Europe.”
John Collison Feb 24, 2026 ▶ 21:02 Stripe’s 2024 annual letter
CHEEKY PINT 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
CHEEKY PINT Assertion Not checkable as stated
Collison: 25% of Delaware corporations are formed via Stripe Atlas
“25% of all Delaware corporations are now created with Stripe Atlas.”
John Collison Feb 24, 2026 ▶ 0:46 Stripe’s 2025 annual letter
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT Assertion Supported
Collison: Most profitable third of US public companies holds two-thirds of market cap
“Today, the most profitable third of publicly listed companies in the United States accounts for two-thirds of the total market capitalization, the highest share since data began in 1963.”
John Collison Feb 24, 2026 ▶ 2:17 Stripe’s 2025 annual letter
CHEEKY PINT Assertion Contradicted
Collison: GitHub pushes jumped 41% between Q3 2024 and Q3 2025
“Pushes to GitHub, which grew roughly 10 to 12% in prior years, jumped 41%. Between Q. Three, 24 and Q. Three, 25.”
John Collison Feb 24, 2026 ▶ 4:30 Stripe’s 2025 annual letter
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT Assertion Not checkable as stated
Collison: Local payment rails like BLIK and Pix boost conversions up to 46%
“Presenting Blick to your customers in Poland drives an average 46% increase in checkout conversion. Offering Pix does the same in Brazil with a 31% average conversion uplift.”
John Collison Feb 24, 2026 ▶ 17:16 Stripe’s 2025 annual letter
Collison: Future of agentic commerce depends on universal interoperability
“But as with the early internet, the future success of agentic commerce is contingent on universal interoperability. Our ascent through those five levels we discussed depends on our ability to all work together.”
John Collison Feb 24, 2026 ▶ 22:01 Stripe’s 2025 annual letter
CHEEKY PINT Assertion Supported
Anthropologie, Etsy, and Coach adopt Stripe's new Agentic Commerce Suite
“Brands already onboarding to ACS include Anthropologie, Urban Outfitters, Etsy, Coach, Kate Spade, and a bunch more.”
John Collison Feb 24, 2026 ▶ 22:59 Stripe’s 2025 annual letter
CHEEKY PINT 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
CHEEKY PINT 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
Collison: Unified data pitches endure because companies neglect data infrastructure
“Part of the reason this is an evergreen pitch is because companies don't actually have all their data at their fingertips. Companies do not eat their data infrastructure vegetables.”
John Collison Nov 18, 2025 ▶ 4:39 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
CHEEKY PINT 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
CHEEKY PINT Prediction Not checkable as stated
Collison: A dedicated UI for finance could emerge within 10 years
“I feel like there could be a product in the next 10 years for finance people, where in hindsight, it is obviously the correct UI, but just like the spreadsheet kind of came out of nowhere as a UI, it may feel like it came out of nowhere at that time.”
John Collison Nov 18, 2025 ▶ 39:18 Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT 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
CHEEKY PINT Assertion Partly supported
Collison: Most foreign banking markets have only three to eight banks
“People in the U.S. Do not have a good mental model for how different the banking ecosystem in every other country is, because the U.S. Is so sweet generous, it's like, 5000 banks or whatever the number is currently in the U.S., whereas every other banking mark…”
John Collison Nov 4, 2025 ▶ 26:31 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
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)
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)
Great industrialists view general engineering, not specific domains, as their core competence
“If you interpret Henry Kaiser, Howard Hughes, Elon Musk, they decide that their circle of competence is not rockets or roads or what have you, but is engineering, and that engineering competence can be broadly applied to many potential domains.”
John Collison Oct 28, 2025 ▶ 8:31 Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
CHEEKY PINT 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
CHEEKY PINT Assertion Supported
Collison: Stripe partnered with Shopify to roll out stablecoin checkout payments
“We just worked with Shopify to, like they now offer a stablecoin Payments on all of their checkouts, or they're rolling that out on all of their checkouts. That's just not a thing that would have made sense even three or four years ago.”
John Collison Oct 1, 2025 ▶ 1:23:15 Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
Collison: Traditional SaaS growth benchmarks do not apply to many AI companies
“Obviously that growth curve does not apply to many AI companies.”
John Collison Aug 29, 2025 ▶ 7:43 A conversation with Lovable CEO Anton Osika
ALL-IN Disclosure
Collison: Most Stripe employees work from offices in major cities
“I would say Stripe broadly, Is in a pretty similar spot to where it was beforehand, which is most people go into an office. Like most people are, you know part of our San Francisco office or New York or Dublin or Singapore or wherever. And then we have a bunch…”
John Collison Feb 23, 2025 ▶ 1:37 Remote Work Under Fire: All-In Podcast Unpacks Jamie Dimon’s Leaked Rant!
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