The Exchanges

Q That was the prompt? Like, what would a competent CEO do in this situation?

A I love to take the view that, like, I'm a, um, Um, corporate raider. And, uh, um, Shopify went bankrupt, and, uh, I bought it on a fire sale, and I, I'm like, uh, marching in on day one here, and previous management was crazy, and, um, we need to turn this place around, right? Like, that's my favorite. Like, this is, I, I love playing this game every, uh, like, year, um, figure out what I would do differently, and then, like, it's like, let's go. I, I have my to-do list. And, um, I asked a lot of teams to do this a lot. Like, it's like when we have systems that just don't work, um, one of the most powerful, you know, maybe through affirmations, maybe through experience, things you can do is just don't be prideful about the prior work too much. It's allowed, you're allowed to have pride in it, but like, you want to wake up better every day, right? You want tomorrow's version to be better than today. And for that, you have to kind of downgrade What's there? Like you can't, like the sunk cost fallacy is so powerful.

AI assessment note: “I love to take the view that, like, I'm a, um, Um, corporate raider.”

Q Okay, so that's the example he gave me. I haven't played the game. Can you elaborate on this?

A I completely agree. So like, uh, so again, this is like, man, the world has such a weird way of like, um, Somehow changing itself around me to make the stuff that I thought was, uh, uh, irrelevant relevant or is late in life. It's like absolutely amazing. Um, it's just like, okay, so, so video games. Video games are best thought. I mean, this depends on very much on the video game, but in the aggregate, very often see the good video games are simulations. They are word upon itself, and you are an, an high agency actor, and you modify, modify things. You, you, you take, you perform actions, um, you make decisions, and then the Game rearranges themselves, giving you a feedback loop of, usually a very quick feedback loop because of us it's unfun. Um, but it, you, you learn about consequences of your actions, so like, um, uh, competitive multiplayer games are very obvious there, and, and StarCraft and strategy games, they're not that popular as a category of games anymore, but like, um, you know, when I was going for my teens in the nineties, like StarCraft was the biggest, uh, game. And, um, You know, I loved it because it was really, really hard. It was, like, easy to learn how to master, which is exactly, I think, a hallmark of everything that's worth doing for motorsports, for, for, um, kiteboarding, for my, for my hobbies, tennis, all these things are like this. But, like, it …

AI assessment note: “very often see the good video games are simulations. They are word upon itself”

Q Where it's like, well, I wrote this down, right? Changed my mind, but there's some kind of human element where it's like, ah, I don't want to contradict this because it's in writing.

A Yeah, exactly. Again, people like to be consistent over time. I just don't find that important. I, um, I will, I found the, the cheat code to always being right. It's just like, change your opinion every time you get better information, right? Like, so, because as you get closer to the point where you have to make decision, that means you will wind up with the right one. It's like if you do not stop at some point to incorporate new information, right? Like, and if, even if you were wrong, if I figure it out, you know, again, what do you do? Like, You have two, you have one momentarily chance, um, to, uh, steer your concern to the best possible outcome. Um, are you going to take it? Or are you going to be the person who just, like, leans into the comfort of, like, somehow character consistency? Like, why? For what? Like, again, what's the job you want to do? Do you want to look good or be good, right? And so you've got to, like, just change, um, like, it needs to be okay to, uh, change your mind when better information comes, um, It comes along. And again, here's the crazy thing. I think if you go through the transcript of this podcast, you will find, uh, or just ask an AI to do it. It will probably point out various contradictions inside of what I'm saying about what you do. Like, I, I, I'm like, in this, I'm probably on multiple sides. The reason is actually, this is the almos…

AI assessment note: “people like to be consistent over time. I just don't find that important.”

Q Why did you not know that it was going on in your own company, though?

A Because the company was, like, let's say, like, um, four or 5000 people. You know, it's sort of quasi-distributed. We started all the work, and, uh, we had, like, Toronto office and Montreal office and so on. And so it just turned out that, like, you know, in The Toronto office, uh, there was a fairly big project to build the features to add to Shopify so, uh, you could use it for running a supermarket because, you know, just they decided that the supermarket industry is very large and we should go and, uh, capture one percent about it, like in the Dilbert comics. And so, uh, you know, and, and frankly, it, like, I, I'm not saying those were wrong decisions. The, the, the sort of really surprising thing about building a business, or just in decision-making in general, Is that, um, making the right decision is actually child's play, usually. Like, you can make wrong calls, which, which end up, because of work changes, ended up being wrong call later, and so on. That's a different thing. Um, um, but, like, most of the time, if you, like, the bad options in front of you just prune themselves away. They just don't make sense. They're too expensive, or just, like, off mission, or whatever. You, the problem is, and I think school, unfortunately, accidentally drills this into people, is that there's one right answer is sort of what people think. And, um, once they find a right answer …

AI assessment note: “Because the company was, like, let's say, like, um, four or 5000 people.”

Q Wait, what did you mean by the five words you say at the beginning of a sentence?

A I used to go, again, engineer. Um, that's always, like, an interesting experience with, um, uh, four other engineers working for me and, um, like, I, I stay pretty current. Um, uh, with engineering, I still do not a ton of production, uh, um, production engineering, but like I do, um, I, I sometimes start new projects with people like, uh, and, and the first 20, 30 pull requests or commits in many repositories for things that we use, uh, come from me. So like, I, I like doing this. It's, it's part fun, part, I, I sometimes need to tap into my craft. Um, anyway, um, so that's a surprising thing for people, um, uh, of course. So my intuition was always like, okay, well, this is not the right architecture for this kind of thing. And I know this for a fact because I've built this thing before. So let me go to a right, um, uh, whiteboard and just like re-architect this. And like, and so at some point, um, and that like now, you know, Daniel, my co-founder, like, explained to me, well, look, you get, you're pretty defensive then, because they just came to show you basically, you know, what was objectively their best work, because they presented it to you, and that matters to them, so, and then you just, like, it doesn't matter if you go and make a much better system here, on top of the head, um, they are like, um, if I truly ever did this, um, They're gonna be defensive and try to sa…

AI assessment note: “just put, for example, in front of every sentence”

Q No, it's not, they're not boring to, to me and to people listening. Wait, Why do you hate the way that they were doing competition in the industry?

A What I love about entrepreneurship is the, is, is the level of responsibility, personal responsibility people take. I said as much earlier when we talked about the founders who have been responsible for people's livelihoods, it changes you, it does, right? Like, so, like, I, I don't work myself well in an environment where sort of, like, everything is pre-described. I, I don't like joining other people's games, I, and so on. All these kind of things are my biases, and again, you're implementing my biases here. So, in COVID, like, this is, I think, or twenty-twenty-two, I think, or 21, suddenly Shopify went down 80% of stock value, right? Like, that's a, like, again, I didn't think that was a problem because, like, I think The stock market is basically like polymarket. It's sort of a betting market on a future value, right? Like, it's like, it's not like you guys, when, when you guys are wrong, then you just bad at betting. Like, in fact, so I work on a real market value of a company, which you guys are betting on, but I don't know. So like, there's such a discrepancy from the way I see people talk about stock price and, uh, and, and how I, or have ever, or inside of companies, this is perceived.

AI assessment note: “What I love about entrepreneurship is the, is, is the level of responsibility”