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Patrick Collison started building Stripe in 2009, back when the word fintech didn't exist yet. On stage at Y Combinator, he exposed 8 facts about starting a company that go against 97% of what founders were taught: 1) 2026 won't be the last good year to start a company

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GeniusThinking

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20 years ago, every founder feared one tech company: Google. Even when Patrick Collison (CEO of Stripe) was building a startup back then, he got the same question in every meeting: "What if Google does this ?" But the truth is, Google still didn't build most of what people expected. Because no company can chase 100 priorities at once. Cause the teams get in each other's way, and everything slows down. Today the same question is aimed at the AI labs. Patrick is honest that better models will wipe out some products. That part is real. But the fear is far bigger than the record deserves. — Patrick Collison (.Patrick Collison), founder of Stripe, at Y Combinator's startup school
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20 years ago, every founder feared one tech company: Google. Even when Patrick Collison (CEO of Stripe) was building a startup back then, he got the same question in every meeting: "What if Google does this ?" But the truth is, Google still didn't build most of what people expected. Because no company can chase 100 priorities at once. Cause the teams get in each other's way, and everything slows down. Today the same question is aimed at the AI labs. Patrick is honest that better models will wipe out some products. That part is real. But the fear is far bigger than the record deserves. — Patrick Collison (.Patrick Collison), founder of Stripe, at Y Combinator's startup school

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In 2009, Patrick Collison and John Collison went to Startup School in Berkeley, got sushi in Potrero Hill afterward, and decided on the walk home to start Stripe. The reasoning, as Patrick remembers it, was that “we might as well because it probably won’t be that hard.” It took them two years to launch. Seventeen years later, at Startup School 2026, he talks with YC's Harj Taggar about dropping out of MIT twice, why founders should ask what happens if they succeed, and what Stripe’s own data says about the best time to start a company. 00:07 — What Should You Still Learn in the Age of AI? 02:01 — Knowledge Still Matters 05:12 — Should You Drop Out of College? 09:58 — Why Stripe Worked 12:10 — Building Stripe Before Launching 17:20 — Is the Lean Startup Still the Right Playbook? 19:07 — The Hidden Reward of Building Stripe 22:36 — Will AI Kill Your Startup? 25:17 — Why It's Never Been a Better Time to Start a Company 29:23 — What Stripe's Data Says About the AI Economy 30:45 — Build Something People Truly Need
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In 2009, Patrick Collison and John Collison went to Startup School in Berkeley, got sushi in Potrero Hill afterward, and decided on the walk home to start Stripe. The reasoning, as Patrick remembers it, was that “we might as well because it probably won’t be that hard.” It took them two years to launch. Seventeen years later, at Startup School 2026, he talks with YC's Harj Taggar about dropping out of MIT twice, why founders should ask what happens if they succeed, and what Stripe’s own data says about the best time to start a company. 00:07 — What Should You Still Learn in the Age of AI? 02:01 — Knowledge Still Matters 05:12 — Should You Drop Out of College? 09:58 — Why Stripe Worked 12:10 — Building Stripe Before Launching 17:20 — Is the Lean Startup Still the Right Playbook? 19:07 — The Hidden Reward of Building Stripe 22:36 — Will AI Kill Your Startup? 25:17 — Why It's Never Been a Better Time to Start a Company 29:23 — What Stripe's Data Says About the AI Economy 30:45 — Build Something People Truly Need

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Patrick Collison, CEO of Stripe, on whether now is actually a good time to start a company: "You might think, okay, fine... there's way more vibe-coded, kind of lightweight slop, whatever... but actually the median business is doing better this year than a year ago." "By all the kind of objective metrics we can look at, it seems to be a better time than ever to start a business."
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Patrick Collison, CEO of Stripe, on whether now is actually a good time to start a company: "You might think, okay, fine... there's way more vibe-coded, kind of lightweight slop, whatever... but actually the median business is doing better this year than a year ago." "By all the kind of objective metrics we can look at, it seems to be a better time than ever to start a business."

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Mark Zuckerberg: People undervalue option value when starting a company “I never really understood the psychology of deciding that you want to start a company before you understand what you want to do… When you take on a new project - especially if you hire people or start a company - you’re doing that project… You immediately now need to convince someone else if you want to change your mind on something, and I think people really undervalue the option value and flexibility.” Mark advises future founders: “Explore what you want to do before committing… Keep yourself flexible… I think you have to be wary about starting a company too rigidly because you’re going to change what you want to do.” Source: Y Combinator (Oct 2013)

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The biggest startup advice (The Lean Startup Method) you've been following is broken. 1) Launch something small and cheap 2) Win one narrow group of users 3) Grow outward slowly Patrick Collison (CEO of Stripe) says it was only relevant 20 years ago, for two reasons he names: A) Raising money back then was genuinely hard B) And nothing let you spin up a company able to do many things at once But today, AI removed both limits. Which is why he thinks you can now start something far more ambitious on day one. Look at who actually won the last decade. The AI labs. Anduril, the defence company. So many of them did the opposite of lean. If your plan feels too small, check whose advice you're following. — Patrick Collison (.Patrick Collison), founder of Stripe, at Y Combinator's startup school
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The biggest startup advice (The Lean Startup Method) you've been following is broken. 1) Launch something small and cheap 2) Win one narrow group of users 3) Grow outward slowly Patrick Collison (CEO of Stripe) says it was only relevant 20 years ago, for two reasons he names: A) Raising money back then was genuinely hard B) And nothing let you spin up a company able to do many things at once But today, AI removed both limits. Which is why he thinks you can now start something far more ambitious on day one. Look at who actually won the last decade. The AI labs. Anduril, the defence company. So many of them did the opposite of lean. If your plan feels too small, check whose advice you're following. — Patrick Collison (.Patrick Collison), founder of Stripe, at Y Combinator's startup school

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Mark Zuckerberg explains the importance of option value and flexibility before starting a company “I never really understood the psychology of deciding that you want to start a company before you understand what you want to do… When you take on a new project - especially if you hire people or start a company - you’re doing that project… You immediately now need to convince someone else if you want to change your mind on something, and I think people really undervalue the option value and flexibility.” Mark advises future founders: “Explore what you want to do before committing… Keep yourself flexible… I think you have to be wary about starting a company too rigidly because you’re going to change what you want to do.” Video Source: Y Combinator
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Mark Zuckerberg explains the importance of option value and flexibility before starting a company “I never really understood the psychology of deciding that you want to start a company before you understand what you want to do… When you take on a new project - especially if you hire people or start a company - you’re doing that project… You immediately now need to convince someone else if you want to change your mind on something, and I think people really undervalue the option value and flexibility.” Mark advises future founders: “Explore what you want to do before committing… Keep yourself flexible… I think you have to be wary about starting a company too rigidly because you’re going to change what you want to do.” Video Source: Y Combinator

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John Collison: We only had 50 users two years after founding Stripe “We started working on Stripe in the Fall of 2009, and we launched Stripe in September 2011,” John Collison reflects. “I remember right at the beginning when we were starting it I said to Patrick [Collison], ‘Yeah let’s do it. How hard can it be?’ Which gives you a sense of our mindset. And the answer was: two years of difficulty. We had not predicted that.” John remembers feeling dejected when Stripe only had 50 users two years later: “When you spend two years getting 50 users, it doesn’t feel like a whole lot of progress. It feels like things are going pretty slow.” But this is one of the challenges of startups, he argues: “If you’re working on a startup that’s a bad idea, it’s going to feel like slow-going. But if you’re working on a startup that’s a good idea, it may feel like slow-going too.” Yet slow growth has a silver lining: “I think the thing that allowed us to take off in the subsequent years was the fact that since we were spending so much time on each one of those users; since we were hyper-focused on building a great product; and since we weren’t dealing with problems of scale yet, that allowed us to build the product that we wanted. Part of the culture that set in really early on was taking abnormally good care of those early users.” The Stripe founders would get an email or phone call anytime a user ran into a bug. When they sent the customer an email moments later alerting them that the bug was now fixed, people’s minds were blown. They set up a Campfire room that any customer could join and use to message John and Patrick at any hour of the day or night. And if a user was based in the Bay Area, the founders would invite them to come by the office and help integrate Stripe for them. In the Stripe dashboard they would prompt their customers for feedback and feature requests. Then the Stripe founders would reply to that feedback within 10 minutes. “What this meant was that even though the user growth was happening quite slowly in the early days,” John explains, “it actually had a pretty surprising viral effect where people had a good experience, they told their friends about it, and we were able to spread entirely through word-of-mouth even to this day.” Video source: Stanford eCorner (2015)
4:17

John Collison: We only had 50 users two years after founding Stripe “We started working on Stripe in the Fall of 2009, and we launched Stripe in September 2011,” John Collison reflects. “I remember right at the beginning when we were starting it I said to Patrick [Collison], ‘Yeah let’s do it. How hard can it be?’ Which gives you a sense of our mindset. And the answer was: two years of difficulty. We had not predicted that.” John remembers feeling dejected when Stripe only had 50 users two years later: “When you spend two years getting 50 users, it doesn’t feel like a whole lot of progress. It feels like things are going pretty slow.” But this is one of the challenges of startups, he argues: “If you’re working on a startup that’s a bad idea, it’s going to feel like slow-going. But if you’re working on a startup that’s a good idea, it may feel like slow-going too.” Yet slow growth has a silver lining: “I think the thing that allowed us to take off in the subsequent years was the fact that since we were spending so much time on each one of those users; since we were hyper-focused on building a great product; and since we weren’t dealing with problems of scale yet, that allowed us to build the product that we wanted. Part of the culture that set in really early on was taking abnormally good care of those early users.” The Stripe founders would get an email or phone call anytime a user ran into a bug. When they sent the customer an email moments later alerting them that the bug was now fixed, people’s minds were blown. They set up a Campfire room that any customer could join and use to message John and Patrick at any hour of the day or night. And if a user was based in the Bay Area, the founders would invite them to come by the office and help integrate Stripe for them. In the Stripe dashboard they would prompt their customers for feedback and feature requests. Then the Stripe founders would reply to that feedback within 10 minutes. “What this meant was that even though the user growth was happening quite slowly in the early days,” John explains, “it actually had a pretty surprising viral effect where people had a good experience, they told their friends about it, and we were able to spread entirely through word-of-mouth even to this day.” Video source: Stanford eCorner (2015)

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Stripe CEO Patrick Collison shares the tactics he used for finding product/market fit “We tried very hard to understand in granular detail what exactly it was that people were doing, where they were tripping up and so on.” Patrick gives some examples of specific tactics: • A public chat room to provide support to people integrating Stripe • For the first 10 users of Stripe, every API request sent an email to the founders so they could better understand how users were using their product and see if users were doing anything weird • All errors generated a high-priority email to the founders. This created a pleasant user experience where 15 minutes after hitting an error, Patrick could reach out to them and let them know the issue was fixed “These are all kind of examples of a general pattern of trying to be hyper-attentive to all the micro details of what people were doing in the product and iterating rapidly in response to it. Generally speaking, I think pre-product/market fit metrics are actually relatively unhelpful because probably not that many people are using your product. If it’s 20 users, you can in some sense afford to just look at everything they’re doing to understand what’s working and what isn’t.” Another example of this Patrick gives is embedding a text input on each of their web pages with placeholder text prompting users to give them useful feedback(e.g. “The worst thing about Stripe is…”, “The worst thing about this page is…”, or “I really hate the way Stripe does…”). As Patrick explains: “At that stage, you have to be kind of masochistic. We’d always be waking up to all these emails telling us all the terrible things about Stripe. But that was a helpful to-do list for the day ahead. Video source: Y Combinator (2018)
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Stripe CEO Patrick Collison shares the tactics he used for finding product/market fit “We tried very hard to understand in granular detail what exactly it was that people were doing, where they were tripping up and so on.” Patrick gives some examples of specific tactics: • A public chat room to provide support to people integrating Stripe • For the first 10 users of Stripe, every API request sent an email to the founders so they could better understand how users were using their product and see if users were doing anything weird • All errors generated a high-priority email to the founders. This created a pleasant user experience where 15 minutes after hitting an error, Patrick could reach out to them and let them know the issue was fixed “These are all kind of examples of a general pattern of trying to be hyper-attentive to all the micro details of what people were doing in the product and iterating rapidly in response to it. Generally speaking, I think pre-product/market fit metrics are actually relatively unhelpful because probably not that many people are using your product. If it’s 20 users, you can in some sense afford to just look at everything they’re doing to understand what’s working and what isn’t.” Another example of this Patrick gives is embedding a text input on each of their web pages with placeholder text prompting users to give them useful feedback(e.g. “The worst thing about Stripe is…”, “The worst thing about this page is…”, or “I really hate the way Stripe does…”). As Patrick explains: “At that stage, you have to be kind of masochistic. We’d always be waking up to all these emails telling us all the terrible things about Stripe. But that was a helpful to-do list for the day ahead. Video source: Y Combinator (2018)

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Stripe CEO Patrick Collison shares the tactics he used for finding product/market fit “We tried very hard to understand in granular detail what exactly it was that people were doing, where they were tripping up and so on.” Patrick gives some examples of specific tactics: - A public chat room to provide support to people integrating Stripe - For the first 10 users of Stripe, every API request sent an email to the founders so they could better understand how users were using their product and see if users were doing anything weird - All errors generated a high-priority email to the founders. This created a pleasant user experience where 15 minutes after hitting an error, Patrick could reach out to them and let them know the issue was fixed “These are all kind of examples of a general pattern of trying to be hyper-attentive to all the micro details of what people were doing in the product and iterating rapidly in response to it. Generally speaking, I think pre-product/market fit metrics are actually relatively unhelpful because probably not that many people are using your product. If it’s 20 users, you can in some sense afford to just look at everything they’re doing to understand what’s working and what isn’t.” Another example of this Patrick gives is embedding a text input on each of their web pages with placeholder text prompting users to give them useful feedback(e.g. “The worst thing about Stripe is…”, “The worst thing about this page is…”, or “I really hate the way Stripe does…”). As Patrick explains: “At that stage, you have to be kind of masochistic. We’d always be waking up to all these emails telling us all the terrible things about Stripe. But that was a helpful to-do list for the day ahead." Source: Y Combinator (Oct 2018)
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Stripe CEO Patrick Collison shares the tactics he used for finding product/market fit “We tried very hard to understand in granular detail what exactly it was that people were doing, where they were tripping up and so on.” Patrick gives some examples of specific tactics: - A public chat room to provide support to people integrating Stripe - For the first 10 users of Stripe, every API request sent an email to the founders so they could better understand how users were using their product and see if users were doing anything weird - All errors generated a high-priority email to the founders. This created a pleasant user experience where 15 minutes after hitting an error, Patrick could reach out to them and let them know the issue was fixed “These are all kind of examples of a general pattern of trying to be hyper-attentive to all the micro details of what people were doing in the product and iterating rapidly in response to it. Generally speaking, I think pre-product/market fit metrics are actually relatively unhelpful because probably not that many people are using your product. If it’s 20 users, you can in some sense afford to just look at everything they’re doing to understand what’s working and what isn’t.” Another example of this Patrick gives is embedding a text input on each of their web pages with placeholder text prompting users to give them useful feedback(e.g. “The worst thing about Stripe is…”, “The worst thing about this page is…”, or “I really hate the way Stripe does…”). As Patrick explains: “At that stage, you have to be kind of masochistic. We’d always be waking up to all these emails telling us all the terrible things about Stripe. But that was a helpful to-do list for the day ahead." Source: Y Combinator (Oct 2018)

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