5 Lessons from Patrick Collison of Stripe

On hiring, asymmetric bets, user acquisition, and more.

Hey! Justin here, and welcome to Just Go Grind, a newsletter sharing the lessons, tactics, and stories of world-class founders! Today is a free edition available for everyone. To become a premium newsletter subscriber, upgrade and start your 14-day free trial today:

Together with Notion

Revolutionize Your Startup Workflow with Notion AI

Running a startup means juggling a multitude of tasks—emails flooding in, crucial decisions looming, and the constant quest for peak productivity. That’s where Notion’s latest game-changer, Q&A, steps in.

Picture Notion Q&A as your very own librarian—an AI feature designed to comb through all your workspace intricacies, historical business data, and meeting notes to answer your questions.

The best news? If you’re already a Notion AI user, just head over to your workspace—Q&A is included in all existing Notion AI subscriptions.

And for everyone ready to supercharge their Notion experience, you can get started with Notion AI for only $10 a month.

5 Lessons from Patrick Collison

In the third installment of my 5 Lessons series, we have Patrick Collison, co-founder and CEO of Stripe, a company worth tens of billions of dollars.

Patrick is one of the most fascinating people I’ve come across in my research of world-class founders.

The deep dive I wrote about him in April of 2023 was filled with lessons and today I’m sharing five of them from that research.

1. Become a Voracious Learner

Patrick’s bookshelf is available online and it provides a glimpse into how you become a formidably smart individual.

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.

Chris Sacca

From Patrick himself on why he reads so much.

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.

Patrick Collison

2. Utilize the Collison Installation

Paul Graham of Y Combinator described Patrick’s method of signing up customers in the early days.

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.

Paul Graham

3. Upgrade Your Hiring Process

A more effective approach.

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 effective way to go about it.

Patrick Collison

Conversely, this approach requires patience but pays off in the long run.

I can think off the top of my head of five people who took 3+ years to hire.

Patrick Collison

4. Make Asymmetric Bets

An example in regards to choosing a product to develop.

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.

Patrick Collison

This applies to building relationships as well.

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.

Patrick Collison

5. Improve Your Decision Making

Find ways to make sure all your options are better.

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?”

Patrick Collison

Four ways Patrick has evolved his decision-making.

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?

Patrick Collison

Want more insights?

Since February 2023 I’ve spent more than 1,000 hours researching and writing about world-class founders, publishing 47 in-depth profiles of people like Sam Altman, Tyler Perry, Patrick Collison, Estée Lauder, Travis Kalanick, Coco Chanel, and many more.

These profiles are typically 4,000 - 8,000 words long and are filled with valuable insights for entrepreneurs.

A few weeks ago I teased a product I was thinking about creating from all of this research and it’s now available for preorder.

It’s called Insights by Just Go Grind.

The idea is simple: Share the best insights from the founders I study to help you build your business.

I’m going to share the insights I find from these founders on an ongoing basis with this product which is now available for preorder and will be coming out in a few weeks.

If you want to take advantage of preorder pricing before I double the price, preorder today.

Recent Deep Dives

Thanks,

Justin

P.S. Interested in sponsoring Just Go Grind and reaching 23,000+ founders, investors, and operators?

P.P.S. Want to work with me 1 on 1?

What did you think of today's newsletter?

Login or Subscribe to participate in polls.

Join the conversation

or to participate.