Patrick is quite literally one of the smartest people I’ve ever known. Like, he puts Larry Page on his heels smart. I don’t know anyone who has 1) read more books and 2) has the near photographic memory for what he has read. His thoughts are provocative and challenge the status quo. His success is no accident.

I think I was actually really lucky where from an early age, my parents were very okay with myself and John charting our own course. And you get these real hothouse environments where there’s a lot of pressure to go to this school, go to this college, pursue this career path, whatever. You really feel like you’re on these narrow train tracks. And I would say that our upbringing was the opposite where really, our parents, even when we wanted to make very ostensibly strange and surprising decisions, our parents supported us.

So when I was a 15-year-old and wanted to take a year off school to just program full time, my parents were supportive of that. Or when I wanted to try to drop out of school to go take this totally different exam system, my parents were okay with that. And so we had this upbringing where our parents supported us in that way.

The boys went to a school with fewer than 20 kids per grade. When bored in class, Patrick read books. “I would line up the angles so I was hidden from the teacher’s view,” he says, adding that he found out years later that an enlightened principal had instructed teachers to allow it.

Patrick spent his last year studying at home so he could take the required standardized tests early and graduate at 16. (“Surely the smartest redhead in Ireland,” read one headline about 16-year-old Patrick being named Young Scientist of the Year for developing a programming language and artificial intelligence system.)

He condensed what’s normally a two-year test-taking process into a 20-day period in which he aced 30 exams. Then he ran a marathon to celebrate.

And so I went back because I felt that I hadn’t really properly rejected the hypothesis that maybe I should try to become a professor; maybe physics is what I should be at least attempting to spend my career on. And after a year back at MIT, I decided that that was not the case.

It’s useful to focus on adding another zero to whatever you define as your success metric—money, status, impact on the world, or whatever. I am willing to take as much time as needed between projects to find my next thing. But I always want it to be a project that, if successful, will make the rest of my career look like a footnote.

The background context here is that under almost every ostensibly sane analysis, Stripe looked like a bad idea.

This was a crowded market, there were tons of existing incumbents, there were significant regulatory and partnership/institutional barriers to entry.

We had no experience in the domain. We were very young. We weren’t even U.S. citizens, and an ecosystem that again, just because of the regulatory dynamics, that sort of adds to the complication.

We had no obvious mechanism for gaining significant distribution, and we were not a naturally viral product or one with an organic adoption the way maybe a social network or a consumer product might have.

We had a set of iPhone apps for the iPhone from the very start. You probably remember there was that one year between '07 and '08 when there was no app store. And so there were jail broken apps and Patrick and I ran a business that was offline Wikipedia for your iPhone.

And so compressive English Wikipedia was the largest by far, but as you stripped out tables and images and everything like that, you could compressed it to have a fit on a four GB iPhone. And it was especially popular overseas because, unlike in the US, the iPhone didn't launch often with good data ponds. And so you had people without internet access. It was really useful to have this Hitchhiker's Guide to the Galaxy.

But we were at the time, when we started doing this, we were teenagers. We were selling it on the app store and to teenagers, we felt like we were just raking it in. I mean, just absurd amounts of money for kids at the time.

And we would look at the app store, we'll give you these reports of where people are buying the app, and you have sales happening in Saudi Arabia and Mexico, and all these places buying your app. But again, these two Irish hooligans running a multinational business.

And so Stripe was originally incorporated as SlashDevSlashFinance, Inc., spelled S-L-A-S-H-D-E-V-S-L-A-S-H, etc. The slashes were actually spelled out. And the reason for that is we – well, it’s a long story. I won’t bore you with it. It was a programming joke, but we thought it was funny. The rest of the world, to our shock and surprise, did not quite find it as funny as we did.

And the first name of the product was SlashDevSlashPayments because we wanted a slightly broader company name than product name. And extremely confusingly, while the company had it all S-L-A-S-H stuff spelled out, the product was just D-E-Vpayments.com.

Stripe is one of the most successful startups we've funded, and the problem they solved was an urgent one. If anyone could have sat back and waited for users, it was Stripe. But in fact they're famous within YC for aggressive early user acquisition.

Startups building things for other startups have a big pool of potential users in the other companies we've funded, and none took better advantage of it than Stripe.

At YC we use the term "Collison installation" for the technique they invented. More diffident founders ask "Will you try our beta?" and if the answer is yes, they say "Great, we'll send you a link." But the Collison brothers weren't going to wait. When anyone agreed to try Stripe they'd say "Right then, give me your laptop" and set them up on the spot.

If you have to compete on the merits of the product and just rely on people being honest about how well it works or doesn’t, that forces you to just build a product development organization that can compete on merits.

And so it might be harder to get that initial traction, but if you can get there, you actually really have an upper hand relative to more traditionally incentivized companies because they’ve probably gotten a bit lazy and a bit ossified and just a bit less competitive on this axis. And once you can make the battle about the quality of your product and the quality of your product development, if you can get the battlefield to be on that axis, you really have a huge advantage. And our experience was the incumbents just couldn’t react.

It’s such a deep cultural and organizational thing that it’s very difficult for competitors or potential competitors to shift there, whereas if you just have a better marketing campaign, that’s super easy to copy. Anyone else can buy a competing billboard or pay more for the Google Ads or whatever. And so again, we didn’t realize all this in advance. But I think that ended up really helping us.

We didn’t seriously think about stopping. I think both of us are – it’s less I think we’re both really determined and more I think we’re just stubborn. And so the idea of stopping just – it didn’t seem like a – I guess it didn’t feel like an option for us. Determination sounds glamorous to me. And I’m not sure we have that. But I think we’re just dogged.

This is I think what you find when you’re trying to hire the best people. You can filter first by expressed interest and then you can secondarily filter by which ones are good. Or you can first look for the good ones and then try to convert them to expressed interest. I think the latter is the more effect way to go about it.

I think there are a few things that we really prize and try to seek in the people we hire. First, a kind of rigor and clarity of thought. So many organizations prize smoothness, smoothness in interactions and trying to reduce or minimize the number of ruffled feathers. And they at least inadvertently, if not deliberately, prefer cohesion over correctness, and we really try to identify people who are seeking correctness and who don’t mind being wrong and who are willing to at least contemplate things that seem improbable or surprising if true or really divergent [from] that which is the generally accepted status quo. And that’s hard to find. I don’t think most of the educational institutions that we all tend to have attended do a great job of teaching that. We look for that combination of openness and rigor.

The default outcome is that you do not survive; and to survive over the medium or, even with more difficulty, over the long term, that is like an unnatural act. And so you need to find people who not just are willing to push against the expected trajectory of non-existence, but people who actually enjoy that, who want that. Because if they’re merely willing to do it but they don’t actually enjoy it, then the work is probably going to be less fulfilling for them over the medium term.

The cliché, of course, is that startups are extraordinarily hard, and they just are. You want somebody who is at a stage in their life where that’s the kind of challenge they want, where the fact that the particular area in which they’re going to be working is undefined or significantly under-built-out or significantly broken or whatever the case might be, that that’s what they’re looking for.

And then we try to find people who just have—again, to return to these words—interpersonal warmth and a desire to make others around them better and just a degree of caring for others and a desire to be, nice is kind of an anodyne word, but to be nice to them and to make them better off.

And so, just to give a concrete example, Atlas, the service we launched for helping new founders incorporate companies, in particular without the geographic restrictions that tended to exist before — it’s essentially open to founders anywhere in the world.

There was no … one reason as to why that was a good bet. You can’t just measure that on any one axis. But when you look at it overall and you see that, “Well, if it doesn’t work, it’s hard to see how it could cause that much downside for Stripe. It’s not going to require an enormous fixed-cost investment in order to learn as to at least whether it’s initially working.

If it did work, it seems like it could produce quite significant returns. The kinds of things we’ll have to do for it directly are things that are probably valuable for us in other parts of the business, so we’ll learn interesting new capabilities and skills in the course of doing it.

Amazon started using Stripe in 2017 to accelerate market expansion in Asia and Europe, and support millions of Prime Day, Black Friday, and Cyber Monday purchases around the world.

Under the new agreement, Stripe will become a strategic payments partner for Amazon in the US, Europe, and Canada, processing a significant portion of Amazon’s total payments volume.

Stripe will be used across Amazon’s business units, including Prime, Audible, Kindle, Amazon Pay, Buy With Prime, and more.

I wanted to quickly chime in to emphasize that our goal in acquiring Indie Hackers is to simply ensure that the site becomes as successful as possible. The Stripe upside we're hoping for is that more companies get started and that they're more successful. We already see a very large fraction of new internet companies choose Stripe; we're mainly hoping that Indie Hackers can help us grow the overall number rather than to grow our fraction.

I think on some level, scaling a business is both relatively straightforward and extremely hard.

It’s relatively straightforward in the sense that it’s usually not that difficult to see what the problems are, and too many times when you don’t see what the problems are, it’s usually because there’s kind of subjective blindness rather than because it’s actually difficult to see the problem.

And so it’s more of a question of “What are you oblivious to because of your own biases?” rather than “What is particularly difficult to observe and what are your corrective mechanisms to account for that?”

So I think straightforward in that sense, and I guess also straightforward in the sense that usually solving the problems is not outlandishly difficult. It’s not easy, but you have to hire someone in this role, you need to figure out how to raise this capital, you need to build this system, whatever the case might be. None of those are easy things, but they’re also not scientific breakthroughs. There are other companies that have done it. There are generally playbooks that exist, and while your particular strategy might need some correction or refinement and you might hit some walls along the way, it’s rarely unprecedented.

And then I think it’s extremely difficult in the sense that you don’t get to really choose the clock cycle and the time horizons. There is a category of flash games, desktop tower defense games, where you have all these little critters scampering across the board trying to break into your fortress or whatever—I start to feel a little bit like that, where you fundamentally don’t control the rate of problem appearance. You just control the other variable, of the rate at which you are building defensive or mitigatory mechanisms to deal with those problems.

Some days you almost have to smile at the unreasonableness of the swath of problems and challenges that have materialized on your desk or in your inbox. In the same way that you see the constellations in the stars, the problems look so implausible and so unreasonable that, like, someone must secretly be screwing with you.

I run quite a bit, and I don’t even run because I enjoy it that much. I enjoy it, but it’s nothing kind of in the immediate moment; it’s not like it’s euphoric or anything close to that... it’s pretty painful. There’s the Greg LeMond quote about how—it’s very dispiriting when you think about it, and it is very deeply true—how “it never gets easier; you just go faster”. And that’s true of running. Like if I stay running for the rest of my life, it will never get easier; I will just—maybe—go faster. But it feels like something I ought to do, I vastly rather [prefer] having run than not having run. And so I continue to do it.

With reading, I don’t feel like I’m weird; I feel like everyone else is weird, in that there’s just … so much stuff to know, and I guess I just feel stressed out by... like, it feels important, it’s obviously important, and I don’t know it. And so, shit, I better get to work. When I’m reading, I’m not in this … especially blissful place. I enjoy it perfectly fine, but I think there are extremely important things that I really should know and I don’t, and that feels problematic.

When you’re starting a company, you have to be both the super-long, optimistic, “I’m just going to buy this stock and hold it for decades,” trader, and you have to be the catastrophic, Taleb-style, “The world is going to hell in a handbasket,” catastrophe trader. And you have to be both. And that’s just weird.

And so I guess the thing that I think is maybe important to understand for folks is it’s intuitive that if a company or a new effort of any sort is not going well that things will feel hard and you’ll often feel dejected, and life, at least insofar as work goes, is not great. But the weird part is that even if things are going well and the effort or the company or whatever is succeeding, things will still often not feel great. And no one told me that before I started.

I reach out to people whose work I admire and tell them that, and often it leads to a dialogue. And in some cases, I’ve gotten to know them pretty well.

I’m fortunate that Tyler Cowen, whom I mentioned, is a friend, but I was never introduced to him; I just randomly emailed him years ago, actually invited him to a Bitcoin Meetup that I held in 2011. And I did not, however, buy any bitcoin, but I invited him to that Meetup and he replied and apologized [that] he couldn’t make it, but we ended up in a dialogue after that.

When you reach out to other people, half the time they don’t respond, but half the time they do. It’s asymmetric; it doesn’t really cost too much when they don’t, and it can be incredibly rewarding when they do. If I did not do that, I would have missed out on a huge amount.

I thought that, “Well, if the company’s succeeding, then clearly, it’s going to be – not necessarily fun but at least it’ll feel good day to day,” whereas the actual reality is that you’re always necessarily operating at the outer edge of what you can handle because if you have spare capacity, you just take on more.

And so you’re therefore, inevitably always on the cusp of feeling like you’re going to fall over. And even as we record this podcast, at this moment, I feel right on the edge of what I’m able to handle.

And on the one hand, I don’t wish it were otherwise in that I enjoy testing myself and finding my limits and developing and stretching myself. But on the other hand, when you stretch your muscles, that’s painful.

Generally speaking I think that sort of pre product-market fit metrics are actually relatively unhelpful, and I think you really want to bias very strongly towards as much sort of inspection and kind of high throughput qualitative feedback as possible, because probably not that many people are using your product, right?

And so if it's 20 users, you can kind of, in some sense, afford to just look at everything they're doing, and try to understand what's working and what isn't.

Pre-product market fit, you should be scrappy and iterative and just focus on the product exploration in the space. Once you have product market fit, I think all the lean startup intuitions don’t carry over. And you become super focused on building a leadership team. And the question is always, “Who’s your leadership team and how well is it working?” And that’s a complete inversion from before. So maybe actually six-year-ago me, I would say focus more on your leadership team.

When you see a smart person holding a point of view, and especially strongly holding a point of view that’s different to your own, rather than try to figure out how they’re wrong – that’s valuable, but you’ll inevitably do that. Your emotional brain will ensure you do. Try and figure out how they’re right. What is a sensible worldview in which what they believe or what they’re saying actually does make sense? That doesn’t mean they’re right, but trying to figure out, if they’re not stupid, why would they believe this?

And I think for whatever reason, the ability to not take offense and to inspect and to try to understand and even try to really extrapolate from an idea or a set of ideas or a worldview without taking offense at it, that’s not something that for whatever reason is really valued in our culture but I think is actually super important.

Sometimes you have a true binary decision like, “Do I go to this college or that college?” “Do I take this job offer or not?” And it’s an investing or investment-like decision. But it’s not usually that.

I think that the question I would encourage people to think more about is, “How do I get to make better decisions?” as in, “How do I make sure the decisions I’m confronted with end up being better?”

It’s not like, “How should I choose between option A and B,” but, “How do I make sure that both options A and B are as good as possible, and there’s also a C, D, and E, and that those options are great too?”

And that’s about how do you explore the space to make sure that you – well, just to return to the example we just mentioned, it’s like, “Do I go to this college or that college?” There’s also a C there which is, “Well, should I go to college?” Or it’s, “Should I become a doctor or a dentist?”

I think there are four big differences. The first is... I now just place more value on decision speed. If you can make twice as many decisions at half the precision, that’s actually often better. And then, given the fact that the rate of improvement of decision making with additional time almost necessarily tends to flatten out, I think that most people—certainly that Patrick of five years ago and partly from Patrick of today included—should be operating earlier in that curve.

Make more decisions with less confidence but in significantly less time. And just recognize that in most cases, you can course-correct and treat fast decisions as a kind of asset and capability in their own right. It’s quite striking to me how some of the organizations that I hold in the highest regard tend to do this.

The second thing is to not treat all decisions uniformly. I think the most obvious axes to break them down on are degree of reversibility and magnitude. Things with low reversibility and great impact and magnitude, those ones you do want to really deliberate over and try to get right.

The third thing is, I now try to fairly deliberately just make fewer decisions. “Why am I making the decision?” And for some kinds of decisions, there are some good reasons for that, and there are some decisions the CEO ought to make and is fundamentally on the hook for, but there are some decisions where if I’m making it or if I have to make it, that probably suggests [that] something else organizationally or institutionally has broken.

And then fourth, when I realize that I would make a decision differently [to] how someone else would make it, not even really discussing the decision itself but trying to dig into, what is the difference in our models such that they want to make Decision A and I want to make Decision B?