The Wisdom Wall

“engineering involves applied systems design. Um, it, it has a discipline of systems design that is just vastly, like, we're not talking about slightly ahead. We're talking about a hundred years ahead, um, in, in, in, to everything else. It is not a contest when, when you, when you hold it up to, uh, sort of industry…”

“Hire smart people and then get out of their way. I think that's a waste of everyone's time. It's not even good for the, like, it's a nice story, but it's, like, dumb. It's, like, one of those would be nice if that would work, but doesn't.”

“I actually think even concepts like roadmaps and, and just generally plans are actually overrated. Um, I think, um, uh, like a road, the best possible roadmap is have a very clear guide view of what matters to your, um, merchants. Have a super, um, strong model of your own capabilities, um, um, as a company, uh, and…”

“The best thing founders can do is subtraction. This is surprising, but, like, it's, it's, it's the, the, the reason, like, it's much, much, much easier to add things, um, than it is to, uh, to, to, to, to remove things.”

“a lot of, uh, multi-billion dollar companies, um, uh, in, in technologies are, like, come from, there is sort of three, four, five year period of startup creation, right? Which was this, Extreme Goldilocks zone of, um, uh, everything was changing. Mobile, SaaS, internet, broadband, um, remember broadband? All these…”

“I think a great entrepreneurship is actually extracting amazing innovative ideas out of now much, much, much more innovative larger companies than existed previously, um, and bringing them to other fields, and I think that's a good form factor for entrepreneurship.”

“Shopify's stock price is like this crazy function over time based on, again, sentiment, market value. So tying everyone's lifetime earnings, really, but like to this other thing, which is like wildly swinging compared to the thing that we are all working on. Feels like just such a Pattern violation I think. Right?…”

“everyone pays lip service to innovation, but innovation costs you a lot. Innovation is a, if you want this, every single, like, solving any single problem in a company is tenix as hard as it is if you don't.”

“Pareto principle alone tells you that first 80% of every field can be done 20% of the time. You, you, you can, you can, you can develop easily five fields, um, for, uh, in, uh, to, to, to a degree of eight out of 10, um, While the specialist is just looking at primary topic, right? So, um, and frankly, this is even…”

“the problem is, in any other case, you reward the most prepared, and the most prepared are usually the people with the most time, and they with the most time are not usually people working on important things, right?”

“what Shopify allows People to do is like have, you know, for 29 dollars a month get something that gets them pretty close to having all the things that Jeff had to build for himself when he started Amazon, right?”

“So the problem, I think, what makes it rarer that companies, great copies are created outside of them, is partly because, um, then, um, Secondary market people read the books from primary market people, they get the wrong lessons.”

“One of the most, like, biggest differences in, um, primary, in secondary places is, if I hire someone, we are probably, like, the chance that we are gonna still work together in a decade from now is super high. It just, it's, it's, it's, it's a different, it's just different in this way. That doesn't sound like a big…”

“I think the world we are actually spending our time in, like, we've almost built throughout the last hundred years, every company that solves a complicated problem. And so the only kinds of problems that are now left are what's usually referred to as complex problems.”

“I found there's a lot of great companies, um, that suddenly became not great because, um, Through, especially when they are founder-led, they were comfortable in a world of complexity where things aren't so measurable and so clear, um, but where you optimize for the holistic total and saying, hey, the product needs to…”

“one thing that happened with Shopify, uh, which made actually, made making Shopify actually really hard, is that, um, we did not really have competent competitors. It's really, it's really almost, it's really, really, really hard to build a company if you don't have an obvious enemy.”

“root causes are really rare, and, uh, again, events don't happen in sequence, and are cause and effect all the way through. Um, the world is loopy, um, it's not, you know, and, um, everything, like, if something is bad, and you want to change it, there's usually something that reinforces the bad behavior, and we have…”

“no one in a company works on the stock, um, if things are going well. I think if people start working on stock, things are actually, like, that should be a sign that things are going pretty poorly in the company.”

“best practices actually just simply means don't take risk and do with what everyone else is saying you should be doing. Um, best practices are not that, like, good. Like, they, they, they should be best, no, uh, their average risk adjustment. Yeah, exactly. It's just average.”

“there's very few very, very important things that can be done by individuals anymore on, on, just, we, we've almost mined the entire value space. Like, like all, basically all the minerals that are, like, like on the surface have been mined out, right? Like, so, Oh, like, minerals of value. Um, the, um, Other, like,…”

“For something as important as compensation, I think we should not press into service reflexively such highly financialized, um, uh, derivative, like, the instruments of enormous complexity and huge, um, Variance of outcome without there being an agreement with, between both sides of, um, ah, that that's something that,…”

“The actual experience of planet Earth in the same way a comp, like a stock tracks the fair market value of a company. Um, it's maybe eventually convergent, but sometimes vastly swinging up and down based on... And driven, driven a lot by media, right?”

“Most people should opt for range. Specialists, uh, will, like, everyone who knows that there should be a specialist knows they should. You know, like, it's like everyone should be a specialist knows they should be. Like, they, they, they, this is, this is a very particular set of character traits, um, which wants to…”

“the problem is that the, you know, you can never un-VC fund yourself. So, um, when, when a decision is something that you can't take back, then it's worth really, really understanding.”

“and if we bring in experts, Um, in, in, in topics, um, that are important, like when we built a payment gateway, we really needed people who understood the payment, payments industry. They're not the people who run the group. They are the people who support those people.”

“Like, there's three kinds of process. Um, there's a kind of process that, um, makes things that were previously impossible to do possible. That's good. And there's a kind of process that makes something that was previously possible significantly simpler, which is also good. Like make it 10 times better. Ideally make a…”

“you change the environment to make it so that people just, their, uh, common sense compels them to do the right thing. Like, the shortest way of stating that is, like, water will always follow the easiest path down any kind of mountain, right? Obviously. So you can't, like, the water everyone gets that you cannot go…”

“Everyone wants to do the right thing. It's just we ask people to Use to have to invest their willpower into doing the right thing. And that's not right. Like, I mean, it's, I mean, you can try to do it, but I, I want the maximum amount of people's willpower that they are going to expand during the time at Shopify to be…”

“I think the quality of an organization is not how much it, how, how good it is at preventing, um, bad things from happening. Um, although that's, it's a useful skill, but I don't think that's necessarily the quality of organization. The quality of organization is how quickly it does react to bad things happening.”

“And those are exactly the kind of ways how large companies, uh, slow down. Because on the name of efficiency, they create a massive dependency graph, which is invisible, um, but, uh, slows everything down.”

“in most cases the best way to get better at what you do is actually go broader, like, just learn, add the other skills.”

“like a company that makes no choices of what people they want to, uh, So there, make, I mean, again, you, you end up with a full-on bell curve, and therefore you're gonna end up with a full-on average results, um, because the potential for agreement is extremely tiny if you are fully in implementation of, like, every,…”

“And I think when you study really, really successful people, you invariably find people who are on some kind of, uh, uh, intrinsic, sometimes unacknowledged, uh, to the outside world, um, journey of their own, and, um, they, um, they structured their time management in such a way that they, like, they spent most of…”

“part of what is so great about just this exercise is, um, it is almost impossible for a room of people to, um, like, everyone in a room can talk about the same thing and mean completely different things, but if you're writing, like, a systems diagram on a whiteboard, afterwards there is sync, like, there's a sync.…”

“if you want to learn operational excellence, like, um, Factorio is like a game which will teach it to you by accident.”

“Usually what happens for making a world-class company happen is that there's one company really anywhere, um, that creates sort of a broader geographical consensus that this is the company that all the best people should go look for, right?”

“that's when you become an entrepreneur, by the way. It's not when you start building something, you're just a builder then.”

“Uh, you know, I've, I can directly measure the quality of a meeting with how different people spend their lives up to the point of arriving at the meeting. So the more diverse, the better.”

“If someone is in an inspiring, uh, uh, space that just, just, that just is full of great design, um, uh, and, and, you know, where everything just works, like you're not, your base level of what you will do in your own craft is going to be significantly affected by this.”

“There's nudges for people, like, um, for, for people have, like, if people don't have one-on-ones for a long time, they're getting a nudge about it, right? Like, and suddenly you can universally have one-on-ones much better than having a policy with rights of, uh, you know, what some people do.”

“It's, it's, it's just a mental model for how to think about, um, the relationship between people, right? It's, um, you know, it's something that actually exists, but is rarely documented. People sort of think about trust as almost an on off kind of thing. Like, uh, I trust my mother. I don't trust the NSA or whatever.…”

“I want Shopify to be a company where people have an enormous amount of personal autonomy. But it's not possible to just bestow that on everyone. So, like, because, um, like, you, like, trust needs to be earned. Um, and so, when you have, um, a concept like this, where you can say, hey, get to 80, 90% of the trust…”

“one of the sources often that is completely underexposed to the business world is actually the academic world.”

“the problem is that the, you know, you can never un-VC fund yourself.”

“I actually think it's one of those kind of lessons that you get deprived of if you go straight to an, into a startup accelerator, and then go and, uh, Get, uh, the Series A funding with not a lot of effort, and, you know, like, every company that's being funded, you're gonna get a lot more of whatever they were already…”

“books are sort of the closest you'll ever come to, uh, finding cheat codes for real life. It's like, you can access the entire learnings of someone, someone else's career, and, you know, sitting down for, you know, what is it, 12:14 hours, if you're, if you're a slow reader.”

“everyone in a room can talk about the same thing and mean completely different things, but if you're writing, like, a systems diagram on a whiteboard, afterwards there is, like, there's a sync. Like, people will, like, if someone has an assumption about that system looking differently, that will come up, and so I think…”