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ALL-IN Opinion
Collison: Remote work benefits tech companies by expanding their talent pool
“I think also working remotely has had a bunch of benefits where there's a way larger talent pool available to companies like Stripe.”
John Collison Feb 23, 2025 ▶ 1:57 Remote Work Under Fire: All-In Podcast Unpacks Jamie Dimon’s Leaked Rant!
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
ALL-IN Assertion Not checkable as stated
John Collison: Stripe has previously seen 93% of processed credit cards
“When someone comes and buys something from a Stripe user, 93% of the time, we have seen that card before.”
John Collison Feb 22, 2025 ▶ 18:25 The Stablecoin Future, Milei's Memecoin, DOGE for the DoD, Grok 3, Why Stripe Stays Private
a16z Insight
John Collison: Underestimating internet market size is a primary founder mistake
“I think the lesson we have all learned from the internet is one of the big mistakes you can make is underestimating how large a market is going to be.”
John Collison Jan 2, 2019 ▶ 1:19 a16z Podcast | The Evolution of Payments
a16z Insight
John Collison: No established playbook exists for API-oriented businesses
“As far as we see it, there is not a playbook for building an API-oriented service, and so a lot of that is still emerging.”
John Collison Jan 2, 2019 ▶ 3:31 a16z Podcast | The Evolution of Payments
a16z Assertion Not checkable as stated
Collison: Wish increased mobile conversion by 7% using Stripe Elements
“So Wish is an e-commerce company. They flipped over from a checkout they had built on mobile to Stripe Elements. We spent all this time optimizing a mobile checkout just because it's an interest for us to do and not other people. And they saw a seven percent u…”
John Collison Jan 2, 2019 ▶ 7:49 a16z Podcast | The Evolution of Payments
a16z Insight
Collison: Global payments are fragmenting around regional apps like Alipay
“As more people come online in more countries, as you know, things are heterogenizing where, you know, now you have a Chinese market available to you, but everyone's on WeChat Pay and Alipay rather than credit cards.”
John Collison Jan 2, 2019 ▶ 8:20 a16z Podcast | The Evolution of Payments
a16z Insight
Collison: Measurable metrics create perverse organizational incentives
“Any time that you have, you know, one effect, like a, you know, a positive effect that can be measured and a negative effect that can't be measured, you're going to see all these perverse organizational incentives because people track to the metric that can be…”
John Collison Jan 2, 2019 ▶ 10:22 a16z Podcast | The Evolution of Payments
a16z Disclosure
Collison: Stripe uses browser JavaScript signals to detect fraud better than banks
“When we're looking at blocking fraud, we're doing stuff like, you know, looking at the, you know, we have JavaScript running on the end customer's web browser, and so we can tell a lot more about the veracity and is this customer who they claim to be than your…”
John Collison Jan 2, 2019 ▶ 17:35 a16z Podcast | The Evolution of Payments
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 Not checkable as stated
Stripe Billing manages nearly 200 million active subscriptions across 300K companies
“Billing is being used by more than 300,000 companies, manages nearly two hundred million active subscriptions, and is emerging as the revenue engine of the AI era.”
John Collison Feb 24, 2026 ▶ 1:35 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Not checkable as stated
Collison: Over half of surviving 1957 S&P 500 companies use Stripe
“Of the 500 companies in the S&P 500 at its inception in 1957, only 53 remain in the index today. More than half of that remaining 53 use stripe.”
John Collison Feb 24, 2026 ▶ 2:27 Stripe’s 2024 annual letter
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 Not checkable as stated
Collison: Stripe checkout suite unlocked $114M annually for Turo
“Turo, the world's largest car sharing marketplace, used our optimized checkout suite and saw a 4.7% increase in recaptured revenue, equivalent to an additional one hundred fourteen million dollars each year.”
John Collison Feb 24, 2026 ▶ 4:43 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Not checkable as stated
Collison: Forbes saw 23% revenue uplift after switching to Stripe
“Forbes switched to Stripe to manage its subscription payments, and it has seen a 23% uplift in revenue in the past six months alone.”
John Collison Feb 24, 2026 ▶ 5:02 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 Not checkable as stated
Collison: 6.3% of vertical SaaS SMBs on Stripe hit $1M revenue in year one
“In the US, 6.3% of SMBs powered by vertical SaaS platforms on Stripe earn one million dollars in total revenue in their first year, nearly 60% more than in one benchmark comparison set.”
John Collison Feb 24, 2026 ▶ 10:42 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 Not checkable as stated
Collison: Using a card with a new email increases fraud risk 60%
“For instance, if we see a card being used with a new email address, The very newness of the email address is a suspicious fact, with a 60% higher likelihood of fraud.”
John Collison Feb 24, 2026 ▶ 14:33 Stripe’s 2024 annual letter
CHEEKY PINT Assertion Not checkable as stated
Collison: Stripe cut card testing by over 80% in two years
“With these and other techniques, we reduced card testing on Stripe by over 80% in the past two years, protecting our customers from billions of fraudulent transactions.”
John Collison Feb 24, 2026 ▶ 16:31 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 Not checkable as stated
Collison: Stripe Link is used by over 200M people
“Link, the easiest way to pay online, is now used by more than two hundred million people.”
John Collison Feb 24, 2026 ▶ 1:02 Stripe’s 2025 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 Not checkable as stated
Collison: 20% of 2025 Stripe Atlas startups charged customers within 30 days
“In 2025, 20% of Atlas startups charged their first customer within 30 days, up from eight percent for that same number in 2020.”
John Collison Feb 24, 2026 ▶ 5:13 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 Partly supported
Collison: Stablecoin-powered remittance app Felix Pago omits crypto on its website
“Felix Pago is a remittance app. It's powered by stablecoins. It doesn't mention stablecoins or crypto anywhere on the website. It just talks about customer value, the fact it has nice integrations, WhatsApp, and things like that.”
John Collison Nov 4, 2025 ▶ 1:07:44 Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
CHEEKY PINT Disclosure
Collison: Stripe is open to pursuing hardware if a viable idea emerges
“Maybe Stripe should take on a hardware line of business. If we find one That's good enough. Like, we wouldn't be opposed to it. I think we just haven't had a good idea yet.”
John Collison Oct 28, 2025 ▶ 1:15:37 Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
Collison: Buffett's early partnership letters show raw ambition sanded off later
“What's interesting is I find it stylistically very different. This is the late fifties, early sixties, and it's before he got so polished, you know, it's before he got so folksy and approachable and careful in what he said, and a little more of the raw ambitio…”
John Collison Oct 22, 2025 ▶ 1:37:29 Dan Sundheim of D1 Capital on the art of public market investing
CHEEKY PINT Disclosure
Collison: Stripe modeled its internal project tracking tool on Shopify's GSD
“No, we took inspiration from GSD, your system, as we built out ours similarly, and having a centralized internal source of truth for projects that are going on is, Surprisingly helpful, and it feels like it shouldn't be, but it is.”
John Collison Oct 6, 2025 ▶ 9:52 Tobi Lütke is still captivated by internet commerce, 20 years later
CHEEKY PINT Disclosure
Collison: Stripe Atlas is not a major revenue generator for Stripe
“When we built Stripe Atlas for incorporation, there was no amazing projections behind that, that one day this would be a giant business. It's not a giant business for us by any kind of revenue metric, But we think it's very valuable because people start their …”
John Collison Oct 6, 2025 ▶ 1:07:12 Tobi Lütke is still captivated by internet commerce, 20 years later
CHEEKY PINT Assertion Not checkable as stated
Collison: Stripe PMs built viable Lovable prototypes in three hours without engineers
“I think I mentioned to you that a few weeks ago, my product management team held a hackathon and within just three hours, they had put together real viable prototypes on products that I would want to fund tomorrow. So with no eng, no design.”
John Collison Aug 29, 2025 ▶ 0:05 A conversation with Lovable CEO Anton Osika
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)
CHEEKY PINT Disclosure
Collison: Stripe runs a weekly all-hands segment dogfooding its dashboard
“We do at our, like, little weekly All Hands Weaver recurring segment of Just Walk the Store, where we, like, click around in the dashboard together, and we're tripping over, like, why is that modal there, and that's a bit confusing or whatever, just so we're, …”
John Collison Apr 7, 2026 ▶ 21:46 The history and future of AI at Google, with Sundar Pichai
Collison: Universities and breweries are often the longest-tenured institutions
“Often the longest tenured institutions are universities and breweries.”
John Collison Oct 1, 2025 ▶ 2:31 Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
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