Shopify

“I think of everyone as an entrepreneur, really. Your capabilities, like you are the entrepreneur of your own work output. Your product is what you can do and what you can accomplish. Your market is the companies that exist, and you are selling a exclusive subs…”

“I never begrudge anyone being an intelligent actor in the local incentive system. That is just, like, everyone's allowed. That's pretty much my morality at this point... You get too much out of the incentive system, or the incentive system tells you to behave …”

“The reason why they are my customers is because they have someone who responds to these questions in 24 hours. It's the other way around. It's causal.”

“I require my executives to I mean, at least tell me, but actually do it. Go to a podcast, some international conference, and talk about how Shopify does. The thing the conference is about differently, and why that's better every year. If they don't have a good…”

“We got like within a week of running out of money so many times, and sometimes we were bailed out. Many times it was like, just like the clearance of the one-time try hurdles that shop went through was like millimeters at times”

“The moment I went through absolutely every project I did myself, took like many, like, 16 hour days, I canceled probably 60% of the projects, and over the course of the year, I turned over every one of my executives.”

“When Shopify IPO'd We had one member of executive team who ever worked for a public company. That's it. We had no one who took a company public. We had no one who was an executive at a public company. We had one executive who worked at a public company once.”

“Some of our customers went out of business because they got talked, they talked themselves into their own stack. They hired a CTO who brought in their own team. They used a set of technologies that they wanted to use because they are currently the in thing tha…”

“What a company fundamentally allows you to do is like, just run the counterfactual to the world you see around you, right? Like you get to try to build a thing that you think ought to be there, and then you means test it against the market, and if the market a…”

“You can make a seven out of 10 solution to everything by copying the seven out of 10 that already outside in the market. But if you make from tabular erasers axions, your own version of it, you have mastery over, even if this is a six out of 10, you can iterat…”

“Whereas if you treat someone like other companies in your space as rivals, much easier to have a positive sum outcome there, because Rivalries inspire you to be best.”

“In engineering, if you're insane, like, if you're a hundred times better than other people are in, in, in this discipline usually you can make more money than a than a vice president.”

“It's like, we don't allow people to use word ownership over parts of a code base or so. we only allow stewardship as a work like just as a proxy term, because sometimes you need to be able to talk about it.”

“They often, policies and processes are sort of downside protection. You're trying very hard to make to avoid the people who do things wrong to be of you know, causing so much damage. That's like the downside protection, but you're also really limiting what the…”

“We had like something that was 8000 people in a company, and there was five and a half thousand different titles in a company.”

“If any variable along this way is invalidated, what you should be doing is re-derive the entire thing on top, right? Like you should always prune back the decision tree all the way there and go forward.”

“It was a time we didn't have a lot of competition, so which is also really, really hard for businesses. It's not a good thing at all because again, you don't get, you don't have good rivalry, and you can't sort of Like, even if something seems really good, you…”

“We attempt to never be the highest compensation play bid. Because we have found that the people who Optimize for that, above all else, actually don't do well at the company.”

“In fact, like everything in our offices is from Shopify stores, right? Because again, like if anything we are doing is not mission aligned, we just didn't align to the mission, axiomatically.”

“I got really dismayed with the quality of business books pretty quickly, because frankly, I think the business books are largely written by the people who have time. Well, not the people who actually built companies, frankly.”

“I asked a lot of the founders to become my executives. In some cases, I took people from individual contributors in an engineering team and put them in charge of a very large thing. And you know what? At all, every one of those things worked.”

“I really tried everything and learning like you know, just how to, you know, build the team in such a way that I delegate everything, and I have my different business lines and you know, arrange things. This is sort of after the IPO, and I realized I have to b…”

“There's software that manages all this kind of thing. They can use an AI to preview what the transition will like, be like, because it's trained on all the other reviews I've ever done. So they can sort of mock do it and figure out what I will probably say. Th…”

“I still do not a ton of production production engineering, but like I do I sometimes start new projects with people like and the first 20, 30 pull requests or commits in many repositories for things that we use come from me.”

“Like moment zero, zero interest rate phenomena they're gone. People actually wrote better code all of a sudden. Like, it's like amazing how much, like how consequential, like the zero interest rate absence of zero percent interest rates actually ended up being…”

“Year 21 is like, this is gonna be the most interesting year in our, in, in, in this complex history, probably in everyone, little, I think literally everyone's career.”

“Friends of mine, like, you know, Stripe are running this experiment. Like they've managed what they put off in terms of figuring out how to stay private for such a long time is actually remarkable. I just think they spend a lot of time figuring out how to Sta…”

“Like at the high point of our stock price, I think we were trading at beyond 50 x of revenue and stuff like this.”

“My job is to make a company worthy for the best and brightest to work for. Like this is the part everyone skips. Everyone's like, oh, we need to hire a better recruiting team. Well, maybe you need to also just, like be worthy of a kind of talent that you would…”

“Like, it's just like, I, if I wouldn't have happened, I don't think I would run Shopify anymore. It's just like too, I like, there's much better leaders if in times, like, whoa, if times is stable.”

“So we rebuild our compensation system to completely work the opposite of what everyone else does. We give people, here's your annual salary. Here's an internal system. You go in, you look at it. This is a number. Now you get sliders. You can say, how much do y…”

“A lot of, like, companies are social technology in, in the sense that they allow us to go all in. Like, the only time you're really allowed to spend, I don't know, eight, I'm gonna say eight because that's the right number to say, really, like, fucking 14 hour…”

“I didn't take a salary for, I think, four, four years.”

“I think there's just too much cross pollination. You kind of have to sync the companies towards, like entropy creates equilibrium, and so you end up, like, with the companies just being very recognizably similar to each other, and the activation energy for bei…”

“I love to take the view that, like, I'm a corporate raider. And Shopify went bankrupt, and I bought it on a fire sale, and I, I'm like marching in on day one here, and previous management was crazy, and we need to turn this place around, right? Like, that's …”

“The reason why I didn't move to Silicon Valley is because I knew how to create geographical consensus in the eastern seaboard that Shopify is the best company to work for, full stock.”

“Like, it was the first category of music that just, like, killed it on Shopify.”

“Shopify loves the five person team. We increased to eight. Sometimes, but we think the best team size is one because like a single offer can do things that is impossible to do for teams and hit high notes that are unreachable.”

“So the consequences of bad decisions in software engineering are an externality that doesn't accrue back to the engineers who cost it in almost all instances. So it's like a little bit like factories polluting the environment. It's just like, it doesn't cost b…”

“River, the current system that they have for you. Employing agents to do work and open PRs and everything. Like, everyone is working towards that. Shopify is already there”

“Entrepreneurship is going to be the last bastion of human economic value. If they take everything from us, we will always have entrepreneurship. So, Shopify is sort of like a hedge against every job being taken because they can't take from us our agency and ou…”

“He is the only person at the intersection of like CEO of a large company and extremely accurate detailed on the cutting edge feedback.”