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CHEEKY PINT Assertion Supported
Collison: GDPR reduced profits for small European tech firms by up to 12%
“GDPR alone is estimated to have reduced profits for small tech firms in Europe by up to 12%.”
John Collison Feb 24, 2026 ▶ 24:43 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: 2025 stablecoin payment volume doubled to $400B, 60% B2B
“In 25, the price of Bitcoin dropped precipitously and is now 50% down from October, but stablecoin payments volume doubled to around 400,000,000,060 percent of which is estimated to represent B to B payments.”
John Collison Feb 24, 2026 ▶ 9:14 Stripe’s 2025 annual letter
CHEEKY PINT Assertion Supported
Collison: Klarna is the first bank to launch a stablecoin on Tempo
“Klarna, whose CEO was once a self-proclaimed crypto skeptic, became the first bank to launch a stablecoin, Klarna USD, on the Tempo testnet, using Bridge's open issuance to facilitate faster and cheaper cross-border settlement.”
John Collison Feb 24, 2026 ▶ 11:49 Stripe’s 2025 annual letter
CHEEKY PINT Assertion Supported
Collison: Stripe Capital recipients grew 27 percentage points faster over one year
“Businesses that received and accepted capital offers grew, on average, 27 percentage points faster over the following year than the otherwise equivalent businesses who didn't.”
John Collison Feb 24, 2026 ▶ 14:17 Stripe’s 2025 annual letter
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 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 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 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 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 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
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
ALL-IN Assertion Supported
John Collison: Stripe processes over $1 trillion in annual transaction volume
“It's more than a trillion dollars a year.”
John Collison Feb 22, 2025 ▶ 5:36 The Stablecoin Future, Milei's Memecoin, DOGE for the DoD, Grok 3, Why Stripe Stays Private
CHEEKY PINT Assertion Supported
Collison: Anthropic recently installed Workday
“Indeed, Anthropic just installed workday, very famously.”
John Collison Mar 10, 2026 ▶ 50:45 Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
CHEEKY PINT Assertion Supported
Collison: Average S&P 500 tenure dropped from 61 to under 20 years
“Back in 1957, companies could expect to remain in the index for 61 years. In 1980, the average tenure was 36 years. Today, it's just under 20 years.”
John Collison Feb 24, 2026 ▶ 2:38 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: Harvey quadrupled its revenue in 2024
“Harvey, whose AI legal assistant is used by many Fortune 500 companies, quadrupled revenue in 2024.”
John Collison Feb 24, 2026 ▶ 8:04 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: More US independent pizzerias launched in 2023 than ever recorded
“By 2023, more independent pizzerias launched in America than in any other year on record.”
John Collison Feb 24, 2026 ▶ 9:23 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: Vertical SaaS adoption reaches 25%+ in Australia and ~20% in the UK
“Over a quarter of Australian small businesses are using vertical SaaS, as are nearly a fifth of small businesses in the UK. Other markets like Singapore, 14%, France, eight percent, and Germany, five percent are more nascent, but adoption is growing quickly.”
John Collison Feb 24, 2026 ▶ 12:21 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: Non-bank corporate lending is 80% in US versus 32% in EU
“In the US, almost 80% of corporate lending is now from non-bank sources, compared to just 32% in the EU.”
John Collison Feb 24, 2026 ▶ 22:46 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: US invests 0.7% of GDP in high-growth firms versus under 0.3% in Europe
“While the US invests around 0.7% of GDP in high growth firms, that figure is less than 0.3% in Europe.”
John Collison Feb 24, 2026 ▶ 23:05 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Supported
Collison: December 2025 iOS app releases jumped 60% year-over-year
“After years of relative calm, the number of iOS apps released in December 25 jumped by 60% year over year.”
John Collison Feb 24, 2026 ▶ 4:18 Stripe’s 2025 annual letter
CHEEKY PINT Assertion Supported
Collison: Stripe Press has surpassed one million books sold
“The team recently celebrated one million books sold.”
John Collison Feb 24, 2026 ▶ 26:38 Stripe’s 2025 annual letter
CHEEKY PINT Assertion Supported
Stripe host: Booking.com stock outperformed Google over the past 20 years
“If you invested a dollar in Booking.com and a dollar in Google 20 years ago, you made much more money as a Booking.com shareholder, and I think people don't appreciate that fact.”
John Collison Feb 12, 2026 ▶ 5:44 Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
CHEEKY PINT Assertion Supported
Collison: US dollar-backed tokens comprise over 95% of stablecoin balances
“U.S. Dollars are not that big a share of global currency balances, but the, you know, U.S. Dollars are 95 plus percent of steelbook coin balances.”
John Collison Nov 4, 2025 ▶ 14:32 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
CHEEKY PINT Assertion Supported
Collison: Pieter Levels scaled Remote OK to $3.4M revenue solo
“Nomad List got to 700 K in ARR. Remote OK has gotten to 3.4 million dollars in revenue. Photo AI got to 600 K in ARR.”
John Collison Jul 9, 2025 ▶ 0:42 A Cheeky Pint with serial entrepreneur Pieter Levels (@levelsio)
CHEEKY PINT Assertion Supported
Collison: Stripe had paying customers before raising venture capital
“We got our first paying customer way before we raised any money for the business.”
John Collison Jul 9, 2025 ▶ 5:04 A Cheeky Pint with serial entrepreneur Pieter Levels (@levelsio)
CHEEKY PINT Assertion Supported
Collison: Pieter Levels sold $50,000 in book pre-orders before writing it
“You sold 50,000 dollars of pre-orders for your book before you had written any of the book. You just said, I might write a book and buy it here. And you got 50,000 dollars of sales.”
John Collison Jul 9, 2025 ▶ 10:18 A Cheeky Pint with serial entrepreneur Pieter Levels (@levelsio)
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