In this interview from the Startup CEO Show, host Mark MacLeod talks with Shopify founder and CEO Tobi Lütke about how he learned to be a CEO despite never initially seeking the role. Lütke explains that he approached the position with an engineering mindset, treating leadership as a problem to be solved. He emphasizes three core practices: (1) leveraging his technical strengths and continuously re‑qualifying himself each year; (2) studying biographies to understand decision‑making in context; and (3) deliberately questioning and often doing the opposite of conventional wisdom. Lütke describes how he sought out smart questions for his predecessor, used biographies as a structured learning tool, and applied a minimal‑axiom, interdisciplinary approach—drawing from economics, statistics, psychology, and philosophy—to make world‑class decisions. The conversation highlights his belief that extraordinary results require breaking from the status quo and that entrepreneurship is an applied synthesis of many sciences.
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Tobi Lütke never wanted to be CEO of Shopify. He was not the first CEO of the company. When the first CEO left, Tobi set out to replace him. He knew nothing about what a CEO did. From these humble beginnings, Tobi now leads a 10,000-person market leader, and he is arguably one of the best CEOs in the tech world. In this video, Tobi talks with me about how he learned the CEO role, starting from absolute ignorance. Key things to listen for in this video. First of all, leaning into his strengths. He takes an engineering approach to this role. Second, studying history, in particular biographies. Third, not doing what everyone else does. If you want extraordinary results, you can't follow convention. If you're a technical CEO in particular, I think you will love listening to Toby here about how he learned to be a limitless CEO. Let's listen to Toby.
You were not the original CEO. You didn't necessarily want to be CEO. You bristled hear this, but you're obviously mathematically and objectively the most successful tech CEO in Canada. And just like, would love to unpack how you taught yourself to be that CEO. And, you know, I quote you all the time to my clients about how you talk about having to requalify for your job every year. But I'm wondering just how specifically you did that, especially because, you know, in my brief time with you, one of my observations was that, uh, you bristle at convention. If someone's to say, oh, this is the way you do it, like, you would almost be like, well, then I'm not going to do it. You're going to have to prove to me that that's the way to do it. So I don't think it's as simple as following people and doing what they do. So I'm just curious how you did it.
Yeah, I reflexively just take the opposite.
Yeah.
But I wonder if that's actually— like, that's definitely important for my story, but I don't know if it's important for— like, I think there's many, many different ways there. You know, I just, I love computers. I love working with them. I want be CTO of a company, I frankly, sometimes I feel like I still want to. You know, like me and my co-founder split the company just like so, right? Like, Scott do the business, I do the tech. When Scott left 2008, I think, or '07, I was trying to find a CEO and then just sort of got to talk. I wanted to ask them smart questions. So I just, I'm like, okay, well, what does a CEO actually do? So back then there weren't like podcasts like yours or any of these things. And you know, I start with books and read them, like, but this is, this is how I learn things in technology too, right? Like it's figure out who knows something and then figure out what they learned, or at least how they explained their success, right? Like I tend to find biographies better because they've been, because I find it extremely hard to learn anything outside of a context in which it was discovered. And they also usually give you sort of a, was what did the person know when they made their most important life decisions at the point when they were made, right? Because you get it sort of laid out in sequence. And so I've kind of made a study out of this type of decision-making. And maybe this is a bit also the engineer in me. I just don't like arguing by analogy. Just because something is like in another version of that, I just don't think that makes— I don't think that has anything terribly interesting to say. The world is pretty mid in terms In terms of quality, like again, like I really don't think the really remarkable things we can all list, like it's the Golden Gate Bridge and Rome and like humanity has sometimes decided to make unbelievably great, beautiful things. But like that was a very, very specific times and most of the time we don't. So I don't know why people think doing something like everyone else is such a good idea. Fundamentally, the reason why I left, struck out on my own and wanted to start a company is because I want to do something world-class, right? Like, and if you want to do something world-class, axiomatically, you can't make it the way everyone else does because otherwise you get the same thing. So I think there should be a healthy skepticism of what everyone doing the same thing. And it is really, really a fun practice to be able to argue from ideally very few axioms why a certain thing works, like which leads you in the world of companies very quickly to economics, very quickly to statistics, very quickly to from social studies to psychology really, and also philosophy. It's like entrepreneurship is a very applied version of basically all the sciences to a degree that just makes it like, which is why it's so fun.
Hey, thanks for listening to the Startup CEO Show. If you'd like to connect with me, be sure to visit my website at markmacleod.me or follow me on LinkedIn at The Mark MacLeod or Twitter @MarkMacLeod_. And if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We'll see you next time.
