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6 Oct 2025 Cheeky Pint Tobi Lütke is still captivated by internet commerce, 20 years later
“I'm a fan of functionally organized companies, the trade-off is it’s significantly harder for executives.”
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- 6 Oct 2025
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- Cheeky Pint
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…raction or oligopoly or regulatory capture, everything like that. And you just have a front row seat to the pure competitive differentiation, people succeeding on the merits and it's a very pure form. I feel like you have that too and it's like we should write postcards to the rest of the world. This “real world” thing. The one everyone says your product wouldn't work in, which sounds so dystopian. It does really sound quite dystopian, so I don't want to have anything to do with it. I'd just much rather like, hey, just build this whatever world, whatever that is and invite everyone over. And if it's good it works, then people will join. It's actually that simple. I think it's better to live in a world with not people going direct, people communicating direct, people being real people. There's very, very rarely a PR department or even there's probably a marketing strategy, but the marketing strategy works based on just new ideas and organically,with very few people being highly enabled building products that they care about. We had Mackenzie from Ambrook on here, which is SaaS for financial infrastructure for farms. But she was saying one of the big trends in agriculture right now is direct to consumer stuff where you're actually transacting directly with your farmer. I'm sure a lot of them are running on Shopify as well. What have you learned on the Coinbase board? I never had another job, really. In my apprenticeship I mostly learned what not to do as a company, and then sort of had the opportunity to start Shopify just trying literally the opposite and that's basically what operations I've been running on. It's been amazingly successful, so thank you Siemens. But it's so hard, especially building it in Canada—in Ottawa and Toronto. It's funny, I always had this effect of, I came to a valley a lot when I had time and money. I had office meetings and then talked with people and they described to me how “real companies” do these things and then I went home and tried to implement it. And only years later did I realize very few of the companies describing what they're doing actually did the things that they told me. Everyone gave me sort of an idealized highlight reel and I compared that to my average and then I implemented how I think you could do a better job on the stuff that described and sometimes ended up with good things and I was very, very happy with this. And then now obviously I'm describing when this goes really right and just as often this went really wrong. So Shopify ended up being this sort of lopsided thing that is probably ludicrously over-engineered, but advanced at certain things, and then incredibly primitive at things that no one fails usually. Because in a more liquid labor market where more people build companies, the information is just more readily available. tain things, and then incredibly primitive at things that no one fails usually. Because in a more liquid labor market where more people build companies, the information is just more readily available. Yeah. Brian strikes me as someone who is very hard to manage up to. That's always the risk for CEOs is that people are trying to construct some Potemkin village and he was describing the policy work that they were doing and he was saying, well, the company's meant to be the good cop and the trade group will be the bad cop and then he'd be the trade group and it's like, “Wait, these are also the good cops.” And so he was saying, “Okay, here's our new bad cop plan.” But again, he was just kind of refusing to go along with the things that everyone was serving up to him as the plan. I think great entrepreneurs are ungovernable and it's the problems that often arise when people somehow manage to figure out how to… yeah. I think studying failed companies is actually often more useful than— Yeah. It's not so much that I want to study failures, it's that I really want to avoid making the same mistakes that other people have well intentionally made and found, “Oh yeah, no, that's a blind canyon up there.” It's totally underrated, but completely vital because you die to a thousand paper cuts as a company. So you kind of have to first avoid it becoming a thousand and then second you will make mistakes, make them original so there's alpha in it so that you accrue some additional knowledge that’s now it's unique to you. How do you like to be ungovernable? How do you like to avoid being managed up to. Probably can't share all your secrets… I just think going direct a lot inside of a company too is just like— The journey of the org chart and information flowing up, being polished at each step. Yeah, I don't think up and down is sort of not the right mental model. It's in and out is good. Certain decisions are best made at the outskirts of a company closest to the customers, but I'm a big believer that many decisions have to be brought inwards as well. This is why product reviews are very centralized. It's a way of efficiently moving information completely in the bend of org charts. I'm a fan of functionally organized companies, the trade-off is it’s significantly harder for executives. It's very unpopular with executives because obviously they just don't own the entire shebang that they can make all the decisions in and that requires a lot more collaboration, which feels wrong and feels slow. But you make vastly better products in functional organizations, at least for Shopify and that helps. I just know a lot about the company being in so many details. I try to be in AI stuff first so that I always see it as a gift when something new happens, because I am very good at quickly figuring out stuff. hen I sit there with knowledge and I can now look at, okay, who else gets there fast and those are my future leaders. That's a very implicit test. Oh that's interesting. You're testing some adaptability or something like that. edge and I can now look at, okay, who else gets there fast and those are my future leaders. That's a very implicit test. Oh that's interesting. You're testing some adaptability or something like that. Yeah. The biggest difference between people inside of any company or just in general in industry is some people fall in love with solutions. Some people fall in love with problems. And I just fundamentally a person who appreciates the people who fall in love with problems, it's very hard to distinguish during fairly stable times, right? It's very hard to know who is who because well if you don't change anything they look exactly the same. I like inducing change in general to assess this out. How do you induce change? That sounds euphemistic. I don't know. Just literally like that— do stuff. I think reorgs are a standard way. All reorgs work because reorging is valuable. It doesn't matter what your organization structure is afterwards. Well I mean it does, but there's some benefits to any organization structure. But it shakes things out of the stasis— Well, and the advantages of any organization structure accrue immediately. They have disadvantages that only appear over time. So if you change a lot, you do multiple things, you are also, I think heightening your misalignment with the people you don't want in your company is an enormously important thing. So if you— Back to Brian Armstrong. Yeah, exactly. So if you reorg a lot, you end up the people that select out who don't like that. Which is probably the position to take, even if a company thrives under a lot of change and is exposing itself to a lot of change, then it's important that you're clear about that. I think you try to make your company as different from every other company as possible, which is actually I think the opposite of what most companies most CEOs optimize for. And probably most professional management. Right. I think a lot of people want to make their company as similar as possible to all other companies, but to me that's a lack of diversity, right? There should be diversity in companies, because there is diversity in people and people need to fit/find a product. In what ways is Shopify most different from other companies? I mean this sort of internal tool culture is an example of this. It's quite clearly R&D run in a way that quite a few companies are, but they don't acknowledge. We actually say it and celebrate it, and say we actually are of the opinion at this point that everyone should be able to code at least since vibe coding is around. This is clearly this has gone from a have to spend all of your teenage years in a dark room cultivating a rare skill to spending a couple of weekends with YouTube. Let's go. This is not a problem anymore. Speaking of teenage years, I'm always very interested in the on-ramp to entrepreneurship and the on-ramps to programming. And I'm curious, some people decry that programming has gotten harder to on-ramp into where the first stuff I built was like, janky PHP webpages. But obviously PHP is actually very nice. You're just writing code directly in the webpage and you refresh and that's the execution environment.…
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