Lessons from John Collison

John Collison is the co-founder and President of Stripe.

On Building a Company and Culture

On the importance of early hires: "No batch of 10 people will have as much an influence on the company as those first 10 people." [1]
On defining company culture: "Culture is what happens when the CEO isn't in the room." [2]
On hiring undervalued talent: "If someone is a known spectacular quantity, then they're probably working in a job and very happy with that... We had to to try and find people who were... early in their career or undervalued in some way." [3]
On finding passionate people: "Finding people who are passionate about your product can be a great way to find people because there you kind of have an unnatural advantage over other companies." [4]
On the intensity of starting a company: "Starting a company with someone is... often seven-day weeks and 14-hour days again and again and again and going through a lot of uncertainty, a lot of setbacks." [5]
On evolving company culture: "Don't worry about preserving your company's culture. The culture you have at 4 employees is not going to be the culture you have at 40, and that's okay." [6]
On the power of writing for internal communication: In a discussion about Stripe's culture, the power of writing was highlighted as a tool for clear communication. [7]
On creating a strong company culture: A company should be like the "resonant frequency of some tuning fork," where everyone is aligned with the core idea. [8]
On the founder's role in culture: "Sometimes what people interpret as a very strong cult of founder is just a company having a very strong culture that the founder is a metonym for." [8]
On hiring slowly at the beginning: "We hired extremely slowly at the beginning. It took us a year to get to four people. It's hard to hire as a very small company, and we wanted to make sure we found people who cared a lot about what Stripe was doing." [2]
On the value of a shared history with co-founders: "All the meta issues of working style and how we work together were out of the way and we could focus squarely on the task at hand." [9]
On giving feedback: "Everything from high level how you're doing at your job to minor cultural pointers, the more feedback you can give the better they'll do." [1]

On Product Development and Vision

On the origin of Stripe: "Stripe really did come about because we were really appalled by how hard it was to charge for things online." [10]
On respecting your users: "What we really try to constantly clobber people over the head with at Stripe is that these are people starting a business who are generally really talented... we have another value at Stripe that we try to really inculcate is talking up to the user." [11][12]
On the product development process: "One of the myths you see in entrepreneurship is that people have this dream one night, wake up the next morning, and start building it. It's actually much more of an iterative process." [2]
On balancing vision and iteration: "It's not a vision versus you know iteration trade-off. It's a selection of the things that you really believe in and then being willing to to to to contort yourself to make it work around that." [9]
On listening to the market: "If the market is telling you that you're wrong you really need to listen to that data." [13]
On the importance of user passion: "The passion that the early users had about the product was that leading metric that, that indicated to us that something was there." [14]
On the evolution of a startup's vision: "Startups tend over time to get higher and higher up in how they describe themselves... the sneaky thing they do is they pretend that that's how they viewed themselves all along." [15]
On starting small: "You don't always know in the early days what the largest thing is... for me and Patrick when we when we started Stripe, you know the market research we did was we knew this was something we really wanted as developers." [9]
On the importance of a firm familiarity with the problem: "I think it's not enough to you know have a vague idea or a vague vision of things needing to get better i think you need to have a really firm familiarity that lets you execute." [16]
On building for developers: Stripe was conceived as "A developer-focused, instant-setup payment platform that [can] scale to any size." [17]
On the continuous nature of product development: "Product strategy, product prioritization, product planning, whatever you want to call it, is always going to be really hard... it's even hard if things are going well." [9]
On focusing on the core problem: "It's easy to talk to people over the Web, but it's not very easy to trigger transactions. That's the thing we set out to fix with Stripe." [10]

On Startups and Entrepreneurship

On unscalable user acquisition strategies: "Helping each user personally, sure that won't scale as you grow to a very large size but when a startup is just starting out it really helps you have an advantage as a small and nimble company." [18]
On the fundraising process: "Fundraising is a long and distracting process, and by the end of it, all you want to do is go back to building the product that you're working on." [2]
On the Silicon Valley mindset: "I think there is this very nice, if at times dangerous, untethered optimism that exists in Silicon Valley." [2]
On the difficulty of starting up in Ireland: "Coming from Ireland, it's quite hard to do a startup because you're culturally so far away from what everyone else is doing. In the Bay Area, it's much easier." [2]
On the path-dependent nature of startups: "Startups end up having a really powerful path dependence where... you're not just trying to arrive at the final form for your product, you're trying to get all the intermediate forms in the chemical reaction that get you there." [19]
On things that don't scale: "There will be things in the early days of a startup that make sense in the early days that don't scale later on." [19]
On the "Move Fast and Break Things" mantra: While it made sense for Facebook in its early days, at a certain size, "moving fast and breaking things probably isn't germane." [19]
On the iterative nature of good ideas: "Good ideas often take a really long time to achieve escape velocity, too." [9]
On having paying customers from the start: "With Stripe we made sure we had paying customers from the very start." [2]
On the importance of studying business history: "I'm a huge nerd for start-up history... companies want to put the best face forward they want to whitewash things a little bit and so you don't end up seeing the really interesting detail and the uncertainty from the early days of a company." [5]
On the value of Y Combinator for early credibility: "A lot of our early customers were YC companies who we knew... they knew we weren't going to disappear in the morning." [9]

On the Future of the Internet and Economy

On Stripe's mission: "We deliberately articulate our mission as increasing the GDP of the internet." [8]
On the potential of the internet economy: "Only around 3 or 4% of commerce takes place online today we think that could be an order of magnitude larger." [20]
On the future of commerce with AI: "The big change that we see is that right now, everything is constructed around making a web purchase modality, and there's a pretty significant platform shift on the horizon... a lot of commerce will take place directly within the AI tools that people are using." [21]
On the concept of "agentic buying": The future of e-commerce will move towards "agentic buying" where AI agents execute purchases on our behalf. [21]
On providing economic infrastructure: "With Stripe, the idea is that by providing better infrastructure, by linking the Internet economically, by making it easier for these online businesses to exist, it'll make the web better." [2]
On the internet as a connected system: "The Internet is a testament to a connected system that works - it's a global network where any computer can reach another, and easily transfer information across." [10]
On the global nature of money: "Money definitely doesn't work that way [like the internet]... in the US we have credit cards... in Kenya Uh everyone uses a mobile money system called M-Pesa." [9]
On the growth of marketplaces: "Marketplaces by their nature tend to grow faster than most other companies." [10]
On the long-term vision for Stripe: "I don't think of stripe as a payments company... for me my mental model of stripe is stripe is a an infrastructure company for facilitating you know transactions and exchanges." [8]

On Learning and Personal Growth

On learning from other companies: "You should at least understand... it's funny I remember um Tyler Cowen commenting about Magnus Carlsen that uh he entered some chess trivia contest... and won it... that's not a coincidence." [8]
On the importance of curiosity: "For founders, there's two kinds of curiosity that have a lot of business value... one is absolutely like you say businesses are kind of different at every scale." [8]
On being forward-looking: At decision points, a company can either be "rearward looking" or "forward looking" and recognize the massive growth potential that still exists. [16]
On the importance of being unreasonable: "To spot opportunities requires you to jump out of that mode briefly and and question how things work and be unreasonable in suggesting that it it's not valid for them to work this way."
On the value of being an outsider: "The companies that are often successful in changing an industry are often not started by insiders because the insiders you know know too much about that industry."
On the importance of finishing things: "There's a lot of people who are really excited about tons of things. Only a subset of those are excited about completing things." [1]

Learn more:

Lessons from John Collison

On Building a Company and Culture

On Product Development and Vision

On Startups and Entrepreneurship

On the Future of the Internet and Economy

On Learning and Personal Growth

Written by Antoine Buteau

Lessons from Chase Coleman III

Lessons from Julian Robertson