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People who fear of losing and people who fear of winning are clearly going to look at things much more short term. The world really needs to understand that the people who build companies are fundamentally crazy people. Look, I'm a glorious mess. All the aesthetics around what people believe to be good leadership comes from movies. I have this job so other people can have the jobs I wish I could have. There's nothing better in the world than being a trusted public company. None of the people who are doing jobs that are just tasks for other people have good jobs. The more wealth and resources an entity or even an individual has, the more deserving of scrutiny they are. What really sucks in the world is that we are prioritizing things that sound good over things that work. Like giving money is not virtuous unless it causes the right things. We have too much charity dollars. The problem with charity dollars is they can't be given to anything that has a self healing fitness function. I think great leaders must be exothermic and must be a heat source for the company. Have not looked at the ticker in April. Many of our best engineers have not written code this year. Ever since December. Like December changed everything. Like Opus changed everything.
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This is 20 VC with me, Harry Stubbings.
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Now, I've known Toby Luetke for years. He's the founder and CEO of Shopify, $160 billion public company. Honestly, I've watched a load of his podcasts, they're great. This podcast is a Toby you've never seen before. He was incredibly honest, very funny and pretty controversial. It's a spicy show. Strap in. This is an absolute banger. But before we dive into the show today, did you know the industry average for booking a business trip is 45 minutes? That's a massive waste of your team's time. Well, with Navan, your employees can book a trip in just seven on average. Navan is the AI powered travel and expense platform designed for companies that value efficiency. It drives real business impact through high employee adoption and automated policy control. Now the built in AI approves in policy bookings and blocks the rest automatically. This allows finance teams to stop chasing receipts and skip the month end case. And you get this real time visibility that can save your company up to 15% on your travel budget. And that's why leaders like Visa, Stripe, Figma and even Anthropic rely on Navan these days. Go to navan.com 20VC today to see for yourself and you'll get a chance to win two business class flights anywhere in continental U.S. no purchase necessary rules apply. Head over to navan.com 20vc now. Once Navan simplifies the travel, Airwallet simplifies the spend behind it founders, let's get
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real about the growth tax.
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Right.
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My listeners can get $1,000 off Vanta by going to Vanta.com 20VC. That's Vanta.com 20VC for $1,000 off Vanta.
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You have now arrived at your destination.
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Toby, I always so enjoy our discussions. I've been so looking forward to this. I have many, many questions printed out for us today. Thank you so much for joining me. Stay first, dude.
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Yeah, I was looking Forward to catching up again. I enjoyed our conversation last time and also you know me. So therefore that is incredibly ambitious of you to have lots of notes. Let's try to get as much as we can. Chances are the first question is going to nerd snipe us into some kind of rabbit hole that then hopefully winds up more interesting than expected.
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Questions not Tell me how you started Shopify. I mean Jesus, I love these where they start with and it's like have you heard my thousand other shows that I've done?
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I do want to start, I've found
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with entrepreneurs that you can basically switch put them into one of two buckets. One is motivated by the fear of losing and another is inspired by that incredible hunger to win. For me in particular, I hate losing more than anything and that's what drives me. What would it be for you, the fear of losing?
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My own answer to your question here is unsatisfactory to myself, partly because I'm in the middle of trying to figure this out and if any thoughts would be helpful there. But I do feel like there's a marked difference with this because people who fear of losing and people who fear of winning are clearly going to look at things much more short term. It's like it's the next iteration matters the most. I think that's a limiting thing in a lot of cases, especially with partnerships, especially in business, especially with working together careers or so it just makes everything changes when you're taking a longer perspective. It starts sitting down with people and helping them become the best version of themselves. Just puzzling out something for them or giving them the hardest possible tasks that they could possibly manage in order for them to grow. All these kind of things will have significantly more compound advantage if you take a longer perspective because more of the benefits of these actions will accrue to whatever is you're building. And so it really changes a base framing you take to almost every challenge you encounter. And it's funny because this is what my colleagues and friends here tell me once you understand that being the source of energy that I'm tapping into building, actually the rest of Shopify starts clicking a little bit more in place. It's sort of a clarifying thing because you would Most people that I work with for a while is like they can sort of affect how would Tobi think about this? But they say that doing this actually makes things click in place and makes the next meeting with me a lot more predictable. So I'd say I think there's more orientations. It's Just that many of those don't lend themselves to become executives in companies. So I think this is partly why there's a winnowing effect that happens as people are going through careers that discards people that come from, you know, different motivational backgrounds.
B
Is that winnowing effect changing in a world of AI with different skills and different mindsets maybe required to progress than were required before?
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I think it's actually been changing in a very recognizable way, which is that, okay, so there's a thing called Enneagram which is reasonably commonly used and quite good. Unfortunately, I think it sort of gone woke and changed its terms. And so you would have to find one low background enneagram test from 2019 to get real thing. But if you do sort of separates people into different propensities and whatnot. So this particular test, if I look through the executives I've worked with over the last 20 years, you end up with mostly achievers, basically the people who have never seen a ladder not worth climbing. And there's some few fives who are like the people who go really, really, really deep. That's often a cfo. So there's some there. And in most companies, especially professionally managed companies, there's nothing else in exact. I'm an 8, which I almost already said by talking about my motivational source being that I'm this sort of dissatisfaction or the sort of inshittification of everything which I want to fix, at least in my little nook of a world. And so I don't think aids. AIDS are basically conspired against in companies because they are pain their asses. They just say, they say the thing, they say, like, this is shit. If our shit does not smell better than other people's shit, therefore this is just like exactly what it looks. And any amount of fancy dressing doesn't change what it is. They are dangerous to everyone as the careers around them, they usually don't get the promotion, so they usually leave. What can happen is they start companies because they do often see things right. So the effect and the experiment, I think that's been run ever since. I think Apple brought Steve back. It just created the boundary conditions for more financiers, capital boards to actually just give founders a longer run, like a longer run rate. And then the result, that's pretty good because now you have diversity of executives, you have someone who no one can get rid of, who just calls shit shit. And that just turns out to be really, really good for companies. And so Shopify is remarkably high on aids because I really Seek them. I fundamentally like this kind of discussion. And so that's just like. I mean, I propose nothing. So I think this experiment is being run and I think can be made to be an active thing that people. I think this can be quite actionable.
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One of the most memorable statements I've heard on shows from one of my best friends, Daniel Dines from UiPath. And he said to me, a lot of people think they want to be me, but it's very lonely alone in my head. And I was like, oh, I've never felt so seen in my life. And that's why I'm in therapy. When you hear that, how do you feel?
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I think there's no problem with that. I totally like, look, I have lots of nice things. I have a really fun job. I think that's perfectly natural that a lot of people want to be me. They presumably do not want to spend the last 22 years the way I did. So I think that's a very natural thing. Yeah, look, I'm a glorious mess. So it's just like the world really needs to understand that the people who build companies are fundamentally crazy people. It's an unreasonable thing to do. The old trope of all change and all progress depends on one reasonable man, because a reasonable man does things exactly the same way that everyone else is doing. That is a reasonable thing to do in any kind of situation. So you got to expect that. And it's a package. It's high variance people. It's like all the aesthetics around what people believe to be good leadership comes from movies or the very carefully publicly curated sort of tip of icebergs of how it actually worked. If you look at any biography of anything, it's like you realize it's crazy people who cause this. Read about Watson, the founder of IBM. It's just like you think there's tyrants in business right now. No, it's like you don't know anything about how these things went back in a day. So absolute fireworks every meeting. And so I have this job so other people can have jobs I wish I could have. I'm running interference. I didn't want to be CEO. I learned I had to become CEO because you can't run a product driven company without also being in control of a company. Because the needs of product and companies are extremely divergent. Unless you're taking a perspective three years out, at which point they kind of come to the same point and actually augment each other. Basically every single single day is like a marshmallow test. Are you going to eat the marshmallow now or you get two in the future. And frankly, which we know from the actual marshmallow tests, people don't usually wait for two marshmallows. It's just not in human nature. Everyone's discount rate is different but there's some sense to this. But if you want a great product you have to take this sort of long term position. And taking a long term position doesn't mean just bring up oh numbers in three years. It means willingness to have bad numbers for a while if you think this is going to lead to the right place. And that's a hard choice to make.
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Do you think you have the luxury to do that today being a public company given the expectations that Wall street puts on you?
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Oh yeah, of course dude. There's nothing better in the world than being a trusted public company. I mean the second best thing is being a trusted private company. It's much worse to be an untrusted public company than an untrusted private company. So stack ranking is like unfortunately people become a trusted private company with their investors and have to actually take a step down to being an untrusted public company by going public. This is why people don't go public. They just can't deal with that. Which is funny because it's actually required to then get to the best spots in the end. Which is literally the reason why we did it 10 years ago when we were tiny because it just felt like cool, let's go make the careers of public market investors who bet on us and then we go and they make lots of money and then they become on our side and now they trust us.
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Do you think that chasm is harder from trusted to untrusted if you are much larger? We both know the collisons. I'm sure that chasm for them seemingly will be much larger given their $150 billion price now.
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Yeah, I think everything, any approach works if you have a Collison brothers I don't think it matters for them. They can just decide. I think they are really bad proxy for what you should be doing because most people aren't. I think it's a much saner strategy to do the flip to public as a minor financing. This is the thing 10 years ago More actually 112015 Shopify's revenue I want to say, I mean I'm sure people are going to laugh because I'm getting these numbers wrong but like I don't know, 200 or something million or whatever. It's just like I remember the Valuation for first trade. You set the pricing to then figure out who comes in the book right after the roadshow. It's like high stress meeting later, day after spending a week just. You don't even know which city you're in. Just like, like doing a presentation 100 times. Everyone's like, well, here's fidelity. They did place this order. Here's your other book. And so you have to figure out, okay, well, what is the price you set? You're literally arbitrary that you do. You as a CEO have to set that price. And you get all sorts of advice. Now the advice comes from the investment bankers. And you're not their customers, you're their crop. Their customers are actually the people in the book. So their job is to get everyone in the book the cheapest possible deal. But that is of course, beautifully obscured in the process that who is the customer of whom. Luckily, I sort of studied the way the compensation packages work for the investment bankers before I went on the road. So this was all kind of pretty transparent.
B
I'm sure they were thrilled about that.
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Yeah, well, yeah, I don't think they like that. I mean, but I was also very clear about this. I was like, hey, I understand how you are going to get your bonus. I like you, I want you to get your bonus. But I'm becoming a public company CEO, so I'm going to start my fiduciary duty, T minus 10. So I'm going to optimize for a company, not for you. And then they totally respect that. In fact, the bank overtook me. Public is my CFO right now. So like 10 years later, which is really fun. Yeah. So high stress meeting, like picture 80th floor somewhere in Manhattan room. The biggest table you've ever seen. Lots and lots of people, Paper everywhere, prospectuses calls, high tech and iPad. And with order book, everyone looks at this thing, people are making changes and you have to freeze at a certain point. You pick a price and. And it's just like everyone put a limit order in. That's like caps out at 14 for the first trade. I just thought it was crazy. Everyone in the room, literally, absolutely everyone's like, no, it's like you got to give allocations because those other people will stay in your stock and then long term, they don't immediately flip, blah, blah, blah. I was just like, okay, well, whatever. I raised it past the range because we had a lot of pickups. I knew where my growth was going to come from. I was unafraid. And I picked a number which I thought was A really good one. Fucking first trade was $10 higher or something. It's like fucking hell. So clearly I was really happy with my performance at this moment and I should have. The beautiful thing about markets is actually they are excellent sort of distributed brains and they tell you what it really was. Anyway, the point was we went out at I believe $1.67 billion valuation and I think at various times, not right now, I think, but I don't know, I don't check. It's like 100 times higher now. Can imagine that makes a lot of careers. The people on the road who then didn't fucking not place an order for a couple dollars difference past their range for a good company. Probably got their promotion at all the places. They are the senior partners now. So they love Shopify.
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Toby, you're one of the most thoughtful CEOs that I know and I've interviewed a thousand. So the catalog is quite wide at this point. When we think about today, how many people do you have in Shopify?
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A round number, just like about 7,500, 8,000 people.
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7,500 8,000. How many people will you have in five years time, do you think?
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I mean my real hope is 7,500 to 8,000 at 100x productivity level. I do think there's problems of scale. It would be sad to be in a company that is opportunity limited. Actually maybe I shouldn't say this. Most companies probably are opportunity limited. They're probably not ambitious enough. And I mean this in a product sense. Remember, like Shopify is a fairly broad mission. We want to make entrepreneurship more common. And inside of this ambition we can do a lot. I just think we're going to go into golden age of entrepreneurship. It's by far the most AI safe job. It's by far the most AI benefiting job. Think about that combination here. Everyone who has a plan B of some kind of ambition of hey, I'm going to make products is going to be like, yeah, let's fucking go. All priors don't matter anymore because you didn't need to come from a family of entrepreneurs. And having been at dad's office or your grandma's printing shop in my case, to understand that a business formation is something that real humans can do and that gives employment and these kind of things you can actually, I mean first of all you learn that anyway and then all the various tasks, your handy sidekick AI acts as your co founder will just tell you.
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So if we're staying flat in the hope for all the layoffs that we see today. Is that efficiency gains from AI or is that overhiring in a Covid era?
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Yeah, it's overhiring. Look, AI will change the mix of jobs, no doubt. What you see right now is not AI layoffs. Those are just like the companies that are really slow that over hire just like everyone else doing it. Now what you will see is AI is going to be blamed for absolutely everything because it's the perfect scapegoat. It's the perfect Gerardian scapegoat for everything. It's like it can't fight back. In fact, you can beautifully find communities which I think are entirely wrong, but they are around various people who are talking very eloquently about dangers of AI, even past jobs. And it's like my industry has been gaslighting everyone into AI fear and sci fi has done it for the 60 years before that too. And so I don't even know who's supposed to be on AI's side that doesn't like. It's just like incredible. It's objectively, mind blowingly making my life better in every which way, like everything.
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Do you think you have a utopian lens? When I look at what Claude can do when it comes to social media design, I'm being blunt. A lot of tasks which are not actually that difficult, but they are execution oriented. I know I've done them so people can't be upset with me for it. Claude does it very well. Now how do you keep that utopian mind with the recognition that most of these tasks are easily replaceable with agents?
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Look, because none of the people who are doing jobs that are just tasks for other people have good jobs. Both are not good jobs. Being an automated task queue is not a great job. Great jobs are like things where you have agency and can produce things and make things.
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Do you think everyone can have a great job though?
A
Look, lots of people who are right now rich choose not to work. This is a very, very common thing. Lots of my friends are telling me what the fuck are you doing, Toby? And I'm just like, hey, I'm born bred for working. I'm like don't ask a rain cloud to do the job of a son. This is my task and this is what I do. Maybe some people aren't. Lots of people, what they do on the weekend or what they do in the evening or for some extra dollar like give guitar lessons or so is vastly more productive for society than the a cashier job at the supermarket or these kind of things. So I think people will get options. Products will get enormously cheap. Our purchasing power is going to go up like crazy and people will be able to make choices. We will find new ways of working together. We will find much more liquid ways of moving money around for value generated. I know multiple people who have built companies. They sold the companies really well and they became essentially gentlemen scientists or gentlemen programmers. Like, you know, most of us who use cloud code use it through Ghosty on a Mac. Usually Ghosty is like a terminal application. It's just like perfect. And it's such a weird thing to have spent your time doing this. But the author chose, after he sold his company to by hand make a perfectly crafted piece of software that he thought needed to exist. And now everyone agrees with him on that. It needed to exist because he built everything on it. I have like 15 ghosty terminals on my desktop all around you right now. So that's the world we live in. So I think we are all going to figure out remarkable ways. Think about just how good we are at coming up with new jobs. We are incredible at this. It will never stop being incredible at this.
B
Of the top 10 best paid jobs today, eight did not exist 20 years ago.
A
It's a brilliant start. And that is going to be true in 10 years, too, and 10 years after that. And so my favorite example of this is again, a motor sport Guy is Formula 1. Formula 1 is one of the the biggest spectacles providing the best jobs. There's 800 people building an engine at Mercedes and at every one of the engine manufacturers, 800 people are living in the perpetual golden age of this type of industrial mechanical engineering. Everything matters. It's all skill. They're getting scorecard every weekend. How they are doing compared to everyone else. They are basically in engineering World championship. And that's the same for aerodynamics team, a chassis team and so on. And it's a sport named after a rule book. Think about this. Formula One is literally the name. It's not the name of a sport, it's the name of a rule book which is called Formula One. Because the sport falls out of a rulebook and it's this thick. You can get it. It's actually. I have a printed version of it. It's absolutely fascinating. So that's the 800 people there. Another 800 people work on the car and then the drivers and all that. We just made this up, right? It's like all of our lives is richer because it exists. I think it's my favorite thing about
B
Formula one is actually though, is the Importance of storytelling. If you follow Formula One for 10 years, you'll remember it was Bernie Ecclestone and a bluntly an aging sport with middle aged to older man only liking it with a really decaying audience drive to survive. Saved the sport in many respects 100%
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because it brought the best part out which was accessible to the people who really, really, really worked hard on pulling the sort of story. And like if you watch Rush, you know, I grew up in Germany, so Niki Lauda like a hero in new Germanic, like he was everywhere, right? Like and what a story that is, right? And if you haven't watched the movie, just definitely watch, watch Rush. It's like the sport has had its heroes and its nemesis and its rivalries in such a way, but he couldn't get it out until it got combined with media essentially Hollywood and like Liberty Media and just like. So it's like bringing like think about how much growth is and therefore how much entertainment and delight just by putting pieces together in a new way. It's like aging sport about a rule book. Plus spectacle ends up being something that's of way more value than you would ever imagine. And I just feel like we will find a lot of that. The world is very impoverished by how expensive it was to make software at any given time. There is a limiting factor in the world for why things can't grow faster. And of course growth brings wealth from resources essentially into the economies. That's what it does. If you build a company, you are causing wealth to be created to be brought from the hypothetical things that could exist into the actual things. And once things are actual, then people can use money to move wealth around and our economies grow. I feel like this is worth saying because there's an enormous amount, at least half of population is utterly confused about how this all works and makes way better choices due to this provider.
B
Do you worry that the US hates wealth more than ever before? You said about your friends who stopped working. I have many of those friends. But there is a hatred towards wealth that has never been so visible in my eyes as an outsider looking in
A
at the US I mean I think we are probably at a high watermark for the United States, but it's still sufficiently low that it's fine and easily can get into self healing. The more wealth and resources an entity or even individual has, the more deserving of scrutiny they are. The thing that isn't working right now is that that the process of figuring out who's additive and who isn't is completely broken. It's owned by people acting in utterly bad faith.
B
What do you mean by that, Toby?
A
I mean, we should, like, there's just simply no chance that we shouldn't be sort of deeply, deeply, deeply, in fact, daily thankful for what Elon is doing on planet Earth. Like, he's so singular. Like, I did not touch the steering wheel of my car this morning, right? Like, it just, like, drove me. It also didn't, like, uses any gasoline. I don't care particularly about this, but that's just like, like, fucking hell, that's cool to have that option. And it's also an amazing car. So, like, I have a Model Y. I love it. And by the way, that Model Y that I love is, like, a car that is incredibly affordable compared to the norms of cars, right? Like, it's better than any of whatever fucking, like, Koenigsex I could potentially buy. I have no interest in those because they're not as good at a car. Then I'm going on a longer trip with that car. I also put a Starlink unit into the back. And then just like, if someone else drives, I can work from there. That's also Elon. And then usually I put my phone and talk to the planet Earth. Increasingly, I don't know if you're an X. What you will see is you're getting a lot of replies from people in Japan. Turns out, like, Hitchhiker's Guide, you know, the bubble fish, how central that is to the story. It's just like, cool. You know what? The biggest cheer your thoughts good or bad system on planet Earth is X right now. And the biggest one to N at least biggest follower accounts. And so there's no barriers anymore. You just talk. Someone says something really, really smart in French or Arabic or any other language. And I see it in my feed and we can have a conversation in English back and they see it, and so on and so on. I will spend the rest of his podcast talking about the incredible gifts that he's made. He's captured some very small amount, like, percentage point of all the hypothetical value that exists all around us. He actualized a tremendous amount and captured some of this for himself, which he then reuses to do more of. He's like the one man engine. I'm just like, I'm marveling at this in a way that, like, holy shit, how cool is it that we live in a planet where when you go through the list of the richest people on planet Earth, all of them have built something and that's like, incredible. So what I really mean Is not about Elon. What I really mean is the misattribution of who we should be angry at. It's okay to have a lot of questions of rich people who like inherited very wealth and men use it poorly or come to it by divorce for instance. Or like if you have not not created for wealth you very much are custodian of a wealth and you need to use it gainfully for society. I think what's really sucks in the world is that we are prioritizing things that sound good over things that work. I mean real people don't. Everyone knows exactly what's good when you talk to them. It's just that media, especially state run media and sort of distorting media, like the stuff that's been around for a while is on a beat that just like, like very intentionally trying to obscure what to be upset with.
B
Well so if we just combine those two together, media is kind of distorting what to be angry about. I remember when Jeff Bezos wife gave some extremely large amount of money. I can't remember what it is. And they kind of then chastised her for giving it away inefficiently or to the wrong organizations or to the wrong people. And I was like my God.
A
But that's the good part. So this is what I want more of. So maybe we are on different sides on this but I think again giving something money ideally through a transaction. So someone starts a shopify store, sells a new thing, ethically sourced leather jackets, whatever. When you purchase this presumably it's going to be slightly more expensive than leather. But what you do is you make a vote for it. You make a vote that you think this is a product that should exist and you vote for free money and what will happen afterwards that creates resources for the company and that means it's a viable product, they can employ people. It's a vote for everything that made this. It's also a vote for the supply chain that was created. They ethically source lever now has a customer that's viable, an additional one, therefore the numbers go up, therefore the production can ramp and eventually it's going to come down in price and therefore it might even be in fact with synthetic lever the potential is to make it cheaper than the alternative that some people have just a lot of issues with. The point is every dollar everyone spends is a vote. Real democracy actually happens by capital allocation that's distributed. This is also why we need markets and why capitalism works. Because capitalism causes markets. Capitalism doesn' work intrinsically. It just happens to be the thing that causes the most intelligence to be imbued into the markets because it's the least distorted. And so when money is used, you should figure out what the second and third order effects are of this. And I think, look, if you're very into. Net, this is sort of like hot of a presses, but it's just pissing me off to such an unbelievable degree that I just can't stop thinking about it. Really disarming example of this is I went to a conference once. I went to A Ruby Conference 20045 Ruby Conference I think. First programming conference I ever went to, I stayed for a weekend because at the same hotel there was another tech conference which was a conference called it doesn't really matter. But it was an object oriented programming conference. And basically the first talk was, well guys, I think we won. Not quite sure what we're supposed to talk about because everyone's writing code object oriented right now. And so it was hilarious. I love the honesty. This is the kind of honesty you can only find amongst nerds. I think they actually. I don't know if Uppsala ended up being held again, but I think everyone was just sort of like doing a victory lap over the course. And so in real world we don't do that when we run out of a cause. We cause that cause to continue. And so I think there should be a lot of scrutiny for how money is allocated.
B
You're not thinking by placing such scrutiny on giving, you just prevent people from doing it in the first place.
A
Giving money is not virtuous unless it causes the right things. Even if it sounds good, we need to get away from making good sounding things being beyond scrutiny. It's like you need to look at the data. You really need to figure out what effects you're causing in the world. Right?
B
But what I worry about, there's people like, respectfully you and I didn't mean to make this personal like you. You don't have time to do the DD on the organizations that you're giving money to. You're building an incredible business, changing a generational. So then you just don't bother. But if I said to you, here's an amazing organization, just trust me on it, well, the scrutiny would say don't freaking do it.
C
You like Harry, but you don't know.
B
So it stops all kinds of giving. And then good organizations that would have got money don't get it.
A
Whatever good organizations. This is totally like you show us good organizations, they are getting a lot of money. Trust me, money is being captured by really bad actors in these systems. You will very likely tell me about Mark Carnegie's libraries very soon. Because that is the go to example that is a hundred something years ago. That's the thing that really worked. Rockefeller built hospitals. That wasn't enough. Carnegie built library complete banger. Right. Like so now when I thought good,
B
I just thought of Jensen and Bloom energy. How we're going to fund compute Exactly.
A
Those are commercial things. This is the thing. Like it's like we have too much charity dollars. The problem with charity dollars is they can't be given to anything that has a self healing fitness function. Like which is very fancy way of saying the words for profit markets are voting of if a thing should exist. A not for profit like the world term everyone should be deeply suspicious about. Because you basically said oh, the best fitness function mechanism that planet earth has ever invented. The thing that's only thing that's ever raised anyone out of poverty. Really at scale is the thing you're not participating in. So you're documenting that you're opting out of markets. But you will not tell us what your actual fitness function is. And fitness function is just like. Like how do you know if a game you're on is worth playing and continuing. Therefore the fitness function is going to be just determined by anyone. It replaces merit of organization with pull of individuals. Who is attracted to these places? The people who want to do something for which you have to use pull the smoothest talkers. It's not the builders who are doing it. They go and then run these institutions. And by the way, this is not a bad faith. Take this is the system that's set up. It's fine and sometimes it works books and there are great charities.
B
Do you believe in government intervention? I'm in Europe where we have a lot of government intervention.
A
No, not really. Okay, so let me rephrase this. Yes, I am a fan of Friedrich List who is a Prussian. Long before James Hunt and Niki Lauda's rivalry it was Adam Smith laissez faire and Friedrich Liszt and the Prussian school of economics. And so what the Prussian school says differently to laissez faire is that the role of government is very simple. It's to define games that have as externalities societal thriving and then completely get out of the game. To then let the players in this game cause through means of competition extremely positive externalities to accrue to society. Which again happens automatically in profit seeking markets. Because again what a company does is it takes the potential value that exists which is Infinite, absolutely infinite, and coalesces it into products that other people then vote for. And again, the voting mechanism causes then a larger supply chain and more of a supply of these products coming into society. And then that creates the wealth. And then the wealth is part of a society. And any dollar that's created in a place that brings new dollars into the system cycles seven times through society in a local way. So dollar flowing into like a community. So this is why it's important. Local businesses then cycles seven times through the payroll of people in there, again into the company, then through payroll out, and then to the barista's salary at the local Starbucks and so on and so on. So money itself is amplifying. This is through mechanisms of trade and also through debt creation by banks. So am I for government interventions. Governments are extremely bad at what they do. Everyone needs to know now that the moment a government takes over anything, it will cost 10 times as much, which is really, really, really bad. Because it's just like the second someone says, let's run grocery stores as a government, there's going to just be a couple hundred people like me have to go and build companies to make up the wealth that just simply evaporates in this moment. But one of the most inspiring things that humanity has ever done is outsource violence to governments, because that is caught. Housing, just like that, creates the environment in which personal property can exist. And personal property is the boundary, condition and foundation of everything else I'm talking about.
B
We mentioned kind of fears or concerns or where our society is worrying. One thing that worries me is bluntly, Europe falling into this kind of chasm of irrelevance. It's why I started Project Europe, which kindly supported. You've got U.S. and Canada and you also have Asia. What would your advice be? Or if I placed you in charge of Europe for the future, what would you do to encourage growth and innovation in a relatively stagnating economy?
A
I mean, I have lots of thoughts on this, of course. Canada has all resources that planet Earth needs for literally everything that we are going to do for the next 20 years. It's purely a choice that Canada ought to be the richest country on planet Earth. It can become that every moment at once. It's actually quite easy. It just has to be willing to build some mines, which somehow is controversial.
B
Are you proud of Carney's pushback on Trump? I've had him on the show multiple times. I would like to say he's a friend.
A
I love your interview. It was a very good interview. I think I watched the second one with Connie.
B
Are you proud of him as a Canadian for bluntly standing up in an independent way?
A
I can't say I'm proud of him for that. It's one of the greatest speeches I ever heard. I don't think it's a full, credible witness to the reality on the ground. I also love a speech that is an ambition for a country. I personally disagree with the stance to the United States. I think Canadians are massively overfit to niceness. It's kind of a best thing and a worst thing in a country to prioritize niceness, because it's certainly pleasant. But the problem is it leads to unkind lies. It means you're lying by omission. You're lying by saying things are fine when they aren't. This is a. Can you speak the truth is a much more important test. So unfortunately, the way that intermeshes with the Trump administration is really brutal because it creates this sort of positive feedback loop inside of Cash Canada because he is so unbelievably not nice in any which way. You look at. There's a Trump derangement syndrome in Canada that is just stunning. 60% of people, more than 60. I think the numbers have gone up since people think that the United States is the largest risk to Canada, much larger than Russia or China would be.
B
And you think that's wrong?
A
Of course it's wrong. It's because Canada is a small economy attached to a hegemon. There's been one winning strategy in Canada's history, which is win by helping America win. And that's like Carney's saying that it's over. Everything he's doing I'm agreeing with. It's like, hey, let's diversify the economy. Bang idea. Let's get closer to Europe. Perfect. Let's go. Asia, let's go. I'm pro all the things. I just really don't think we need to choose. The obvious way for prosperity here is to build the shit out of pipelines, build the shit of our industry, get resources that everyone needs, fucking starting to actually refine the stuff ourselves. Because, like, we have the most educated workforce on planet Earth here and we can literally do everything. It's just the problem is, are you still in London? Like, Canada started for trapping beaver pelts, sending to London, getting them turned into hats and then buying them back, right? Like, it's just like this is the Canadian self story is we get the resources, other people make the money, and so we've never changed from that. So we don't make the end products usually. And so therefore it's very, very rare that Canada does anything. It's like Canada Goose, Lululemon, Shopify, maybe Miller Lite. What other products exist from Canada?
B
You mentioned that we over exaggerate the concern there around the US or the threat they pose. The thing that I think we were all not talking about is how every great American company is using frontier American models and then going well that's too expensive. So let's use open source Chinese models to get as close as we can to the benchmark set by US Frontier models. And it's like these CCP funded models are basically powering a lot of the US startup ecosystem in many way ways. Do you think the Chinese threat is underestimated?
A
I mean I think it's both underestimated and overestimated, but I think the much bigger threat is that in a lot of countries, I think this happened in Spain already and I think even in the United States. Social media aside, the moment the government has the ability to decide at which age children can use technologies, it goes like taxes. It's just like AI has so many naysayers. We are going to tell kids they can't use AI. Kids will not stop using AI. What they will do is they will download Chinese models and you will never ever, ever get another high school ad essay about Tiananmen Square as a consequence of that. So is that truly the world we want to create here where children are incentivized to get a monoculture because models are trained and RLF HF'd into a perspective? Chinese models are, I mean especially if you switch them to Chinese and then ask something else to translate. It's a very collectivist worldview, which makes sense because a collectivist country, I mean this is the predominant fight. All politics is just collectivism versus individualism, right? Everything else is smoke screening this stuff.
B
Do you let your kids have social media? I was going to ask this of one of the biggest technology leaders, I can tell you after the show. And his team was like, that's the one question we won't let you ask.
A
This is going to be super, super unsatisfying to people because I feel people hope that I would have a very strong opinion of this that's actionable. And I don't because for the craziest coincidence, my kids are totally uninterested in social media. They completely don't give a shit. They follow links to social media sometimes, but they have no interest of having accounts and they don't have phones. They've never asked for them. It's like, it's bizarre. I saw them when they were very small. So they have PCs, right? Because we do video games as a family and I probably just ran my mouth when phones came up. It's like, I think Tristan said that a bunch of kids in his class are starting to get phones and they're just super distracted and it's cutting into their book reading time, which tells you a lot about Tristan. And then I said, yeah, I mean, at some point you will ask me for a phone and you will have to cash in your PC because you can only have one of those two things. Some of that became the meme in the house and they're just so into the PCs that it just never comes up. So honestly, I can't add much to this conversation. Also with Free boys, which I think is a very important sort of data point there because I think the situation with social media for what it is is very different there with agendas.
B
Going back to our question, I'm making you the new President of Europe, which is a brilliantly American title, which doesn't exist, obviously, as I'm aware. For anyone who's about to chastise me in the comments, what would you do do to ensure Europe remains on a global stage?
A
Well, you have to get rid of the climate cult, first of all, because it's just like, I mean, it's one of the most evil things that's been wrought on population.
B
So when you say the climate cult,
A
you mean random green parties having, as part of a founding myth that somehow nuclear power plants are bad and shit like this, but like it's everywhere, right? Like we can't build incredibly important infrastructure, factories because some fucking frog breeds once in some fucking creek on the perimeter and this shit, right? Like, what the fuck is. You know, if we would be in a saner world and someone would go and write a sort of sci fi book about the future and describe the shit that you actually have to do to do something on this planet. The book would go nowhere because everyone's like, this is just completely made up. But actually we all live in a world where just like people do not understand that there's very few people who have a capability to truly build things and they need to be enabled by the village to build those things. And then they also have to be held accountable by the village. Again, I think, I think Europe, especially now that the UK has left European Union, needs to double down on Prussian economic theory of Friedrich Listener and his co conspirators and just define excellent games that create internal markets. A country is defined by its internal again government services of security, safety, property rights, body of law, policing and these kind of things. Governments have no money. They can't make money. They can only take money by compulsion from people who create things or work. Which is fine because that is a funding mechanism by which then they are doing these services that we deem valuable and build infrastructure and so on. And the infrastructure is a really interesting case because infrastructure is probably the most profitable thing that exists and ever has been existed. Like just building highways changes everything. And building an airport. Everyone's about how much an airport costs. Every airport ever built that's actually connected into the sort of hubspoke system on planet Earth is probably, probably is like. I mean especially the older ones are probably running trillions of dollars of profits in societal true value creation. Infrastructure is like one of those things that businesses are really bad at making. And it sucks that we're committing businesses to have to build infrastructure of this thing because it just doesn't actually fit into the timescales. Like even the long term focused businesses can't really build infrastructure very well. You have an odd SpaceX that can start a new city in a swamp, but that's going to be just like it's not way to do it. So. So infrastructure building is very good. And in the end you define games. You are therefore getting an economy that's growing. And by the way, there's no speed limit for that. Then afterwards you can have a discussion about how do you take the riches from this economy, the additional profits and then sculpt the economy that you want. And this has been ever since the Enlightenment, this has been a path by which all focus has happened.
B
What were you wrong on that cost you the most?
A
Very often most of the things you're wrong about are the paths not traveled where you many years later understand that the counterfactual would be a better position. Lots and lots of deals. I think my most public mistake was going into full on logistics and physical warehouse building just before AI got really good. And we didn't have ability to do both of those things at the same time. So we actually had to apply abandon this thing. I still think the initial decision was right, which is actually how I evaluate my performance. But actually I think this is actually starting to be harder to make that case because I now know about information I could have had and would have been available to me back then that would have discredited this path. So I probably just actually got it wrong. And maybe just admit this, that one sucked because it just affected people's lives with employment and so on. But I'm prong on all the time. I've been wrong more times than most people will ever be wrong because I do a lot of reps on it. I make falsifiable statements because I want people to falsify them. I'm unafraid of a conversation I'm unafraid of. I also just, I don't care that much about what people think about me. Honestly, I just like it.
B
Do not worry that with the weight of your decisions and the weight of your voice when you speak, 7,000 people follow you. The frequency of your wrongness, that could be very costly. I think you've said before your job as a CEO is to inject chaos into an organization.
A
I prefer to call it temperature these days just because chaos probably is too negatively quantitative. I mean, what is heat? Heat is atoms that jiggle and with enough heat, these atoms usually come in the form of molecules. And with enough heat, molecules refuse into something maybe worth having more. That's what all of chemistry does. It's very hard to forge anything new at room temperature. So I think great leaders must be exothermic and must be a heat source for the company. It's very different opinion than the custodial idea of leadership, which is also a valid position to take. I do not need to inject heat into any area that has heat that's not needed. There are some areas that are so red hot because everyone's just so into just chasing innovation or just incredible vision or whatever that my services are not needed here. I get to play a completely different role in these areas, but those are usually not the ones I spend my time on because I spend my time on everything that's really wrong. Again, why people should not overestimate how good these jobs are because you literally I have a folder. So one of my concessions to potentially maybe call it vanity, I don't know if it's quite vanity, but like maybe call it motivational plumbing is like just like I have a part of my Obsidian folders that are just like people that I respect who said things about things I built that are meaningful to me, little jolts of positivity and mini accomplishments because every once in a while especially I can handle a couple of days of this, but once it gets weeks, I only heard things that are going extraordinarily poorly or people making life decisions which have incredible. I mean just retire maybe or do mojitos on beach because there's deep consequences like months of work to figure out how to create continuity of an area that otherwise was going great or whatever or much worse. Any of these kind of things. You get a lot of people's health issues issue. It all affects companies. So sometimes you just get into these really, really dark places and then it's just like a nice pick me up. So I'm not completely detached emotionally from this. In fact, I'm actually enormously emotionally attached to Shopify. I think that's actually a common thing with founders too.
B
Which is why I'm surprised when you said earlier you don't look at the ticker. Every public company CEO I meet is like, it's not.
A
The ticker has nothing to do with the company I'm building. The ticker is a guessing at the fair market value of a company. I work on the fair market value of a company. The ticker is just other people's game to make trades based on their few assumptions of the future, compounding fair market value.
B
When's the ticker been most wrong?
A
At the beginning of COVID I think the ticker went up. I don't even know, like a lot. 100% something more. We did not get 100% smarter at that moment. This is as a founder especially, again, as someone who has lived with a ticker for 10, 11 years. Years, this is really not surprising or confusing. I have not looked at the ticker in April. I know this for a fact. It's probably much longer than that, but I definitely know I haven't looked in the last 23 days when we record this.
B
Which, by the way, makes you a complete anomaly. I pretty much only interview public company CEOs now, and I've never met one like you.
A
Again, it depends on where you are, depends on kind of company you run. In some companies, it also has more relevancy. Right? Like, I mean, if you run a go mine, you have no differentiation in the product. You might have differentiation in the amount of mining rights. I talked with a gold mine guy. This is why this is my example here. I just thought it was funny. For them, technology is actually investor relations. If you are the CEO, your job is to be everywhere and play golf with everyone. Be extremely charismatic. Because if you can somehow finagle your multiple to be slightly higher than the other gold mines, you just buy the other gold mines. This goes very quick. So you consolidate. Your product is not the gold. Your product is actually your IR investor relations. Yeah, like, I mean, that sounds like not an Environment in which I would thrive. Sure.
B
Now I know why you're not a venture capitalist. Toby.
A
I think would be very bad venture capitalists I imagine. I don't know. I tend to think I can onboard to anything. It wouldn't come natural to me. Therefore it would probably not be what I would do. I'm just like too interested in making things I will work every day of my life.
B
Toby, I'm going to do a quick fire round with you. So I say a short statement, you give me your immediate thoughts. What if you changed your mind mind on most in the last 12 months.
A
One thing I'm wrestling with is I had to change my mind. I thought straight out of school engineers would have a really big advantage with no priors and immediately sort of being AI native. And many of them are exceptional and are speedrunning their careers in ways and there's even younger people at universities like we had an intern was 13 from Waterloo which still blows my mind. And he was not even in his first first semester. His mom has to accompany him for all classes which is like I love this. And by the way he's very good. It's just unbelievable. So we are seeing incredible career trajectory increases that I think are coming here. But I had to change my mind here because initially I thought just having no priors would be better because we had to reinvent everything. Turns out the way I think identic programming actually works. You give an initial problem, you give a task, it might come for a ticket afterwards. An engineer constantly talks with the AI to steered in the right direction. All engineers are massively underestimating how important the steering is. It's incredibly important. It's just the same as programming. It's just very high level. And it turns out that just having done a lot of reps and having seen a lot of those just means senior engineers just steer these things in such a way that they can accomplish incredible feats in very very little time. So I don't know what that means exactly, but it's something I have to change my mind on.
B
What role does not exist today that will be incredibly common in five years.
A
There's something about this context engineering which I had a hand in popularizing Tomov I think that will become more recognizably a leg a role in companies that will potentially subsume a bunch of other more specialized roles right now. Honestly it turns out I think people who have done engineering management and management in general are actually excellent AI programmers because they actually have been prompting intelligent agents for much longer than cloud code existed. And they are just good at communicating. So that's, that's now I think increasingly their best work is to prompt other people and AIs directly as sort of part of the same team. So I think there's going to be something that maybe some ascension path job that you can get into from product, from design or from engineering. That's something like a product builder role. It just involves the coordination of intelligent actors to build products. It won't sound or look or be described as what I say, but like that sort of directionality here. I mean honestly, people who are good communicators are usually good thinkers because good communication usually is like distillation of complex thoughts into unambiguous words. Even when I say this, it just sounds like context engineering, doesn't it? I think that is becoming a very, very, very important role if you're building a large scale AI system. Like we have one which we think called river, which lives in Slack and does some ludicrous amount of Shopify's engineering. Now people just talk to it over Slack and it's called river because our Shopify has a very big monorepo. A monorepo is called World and rivers shape the world. So I think that's very poetic. River named herself. We first built her, then asked her what name she wants and she came up with that. And that's kind of crazy. So river sits on Slack, does a lot of Shopify's engineering with people steering her to public Slack channels, which is awesome because then everyone learns from everyone else.
B
What percent of code today at Shopify is AI generated?
A
It's a fair deal, over 50%. It's converting to much higher numbers. I don't think we've updated public numbers there, but many of our best engineers have not written code this year, ever since December. December changed everything. Opus changed everything.
B
Does that excite you as someone who loves the craft?
A
Oh, I love it. It's so wonderful because I love the craft. Love I. And the craft is not lost. Also love mechanical watches, which make no sense, but they're selling more than ever. So people always overestimate again, this is what growth is. Growth is not subtraction of things or replacement. It is just adding there's more in the world. We now have AI as well to all the other wonderful products we can consume. So anyway, I can sit down and write code when I want to do this. Sometimes I do want to do this often. It's part of a steering. Write the part of the code that concerns itself with the data structures and how the data is persisted on disk, which unfortunately that's sort of a German school of engineering which is different from the computer sciencey world of North America. I think North America is wrong. I think you should think about how data is persisted on disk above everything else in your databases and then you can plan the system with this. I still follow this. So work on this either by describing or by literally just making the data access layer. Everything else can be wipe code on top because I know the result will be excellent as long as the data structures have a used right. And maybe that changes in the next couple of months. But that's an area where I can definitely steer the AIs to get better results than they can do themselves for a little while longer. And then afterwards I'll do something else. And maybe I'm going to do it just for kicking it old school. But what my engineering ability allows me to do is reason about these systems in a way that I can be a partner and a coworker that with AI because I can ask it very specific questions to go chase down. And I have those same questions all my life in every meeting. I'm like really wonder what the data structure is here or how we're persisting this or what we save or what we discard or what we redefrive in a data warehouse instead of actually just writing it down in the first place. And now I have my laptop open and my river open and then I can ask a question, I get a result because again river can use the entire monoreport and just goes chase down whatever I'm asking her.
B
Sorry, random one. Would you encourage your children to go to university?
A
So they seem uninterested right now? I think my oldest is probably gonna make a play for it. I definitely would not encourage them to go to university for being part of university. I would definitely encourage them to go get a degree, especially one that's hard to get into because then you're surrounded by people who also got into it. Figuring out how to get in the room with people who really really want to be in the room with a topic of something you care about is actually the cheat code for any career.
B
Would joining a stripe of the day not be better?
A
So my bias would be that if you can be of value to a small company, that's the thing, you have to have the skills to actually be of value. And the company agrees with you and sees that value, you should do it. But that's actually a wonderful test for both sides. An interview is a test. Both sides interview each other. That's what you should try. And I think it's better than the alternative because again, it's much harder to get in a company worth looking for than it is to get into university.
B
Do you believe in nepotism, Toby? Like respectfully, if one of your kids applied for a startup job, the surname is relatively obvious.
A
I remember my kids have the genes of my wife and me. They probably don't like. I think nepotism comes in if someone needs a little bit of help and I think so, but they're fine. I just like nepotism. I think actually nepotism has a bad rep. Frankly, it's annoying. But I'm starting to understand also. I mean nepotism is probably just actually bad. I'm a very big fan, probably you can discern this from what I'm saying here of Thomas Sowell. And Thomas Sowell, just like basically everything he's ever said, is incredibly smart. Amongst the many things worth quoting, I think in a book he wrote when he was already in his 80s, is that that one of his regrets about society is that we have spent the last 50 years replacing things that work with things that sound good. So ever since reading this, I don't have a knee jerk reaction anymore against basically anything that I'm hearing about that sounds terrible because I just try to get to figuring out what is the redeeming value of nepotism. I think the answer is none. So merit double blind is the gold standard. Unfortunately, merit double blind is not the standard. It's very, very rare. I advertisers might be better than some of the crazy shit people are doing to decide who should be appointed, especially in academia. In Canada we have a big thing with basically all the job postings for any kind of academic seats are now full on intersectionality fever dream. Find exactly a description that fits one person in terms of all the disadvantages they had in life, which always comes from a good place and maybe also ends up having. Having some. Maybe it's an arbitrage sometimes because if you know, actually there's always countervailing forces there that prevented them from getting the jobs they ought to. And then on day one, the person you do find is a complete banger in a job and hats off to you, you just play the system perfectly. In any other case, you just made a choice of prioritizing things that are not merit. Right? Which again goes against enlightenment values that literally everything that anyone likes about planet Earth in Western society and the foundation of all the countries that essentially have net immigration depending on in a load bearing way. And I think we should probably keep to some of those.
B
Final one for you, what's the best piece of advice you've ever been given? Mine is you're never wrong to do the right thing and the right thing's often the hard thing.
A
I think the best advice I've been given, but I haven't been giving it. But it's sort of a rallying cry. I think that it's just like I kind of want to coalesce on that sentence just because it's memorable and I think people can't hear it. It enough is you can just do things. It's just like at any point of time the system exists to try to get to good outcomes. If you know what good outcomes are, you can step out of system and give it a go. Cost is lower than ever and action causes information. And again, one of the best things that can possibly happen is you figure out something that there's actually a lot of reason why the system discourages it. There's limits to this, of course. Course this needs to be a completely victimless endeavor. Like you can't have someone suffering for you trying a thing that's very important. People can't have negative consequences of these kind of things because then you're just actually being an asshole because you're dividing people and prioritizing your own gain over other people. And fundamentally you're engaging in a zero sum thing. And in zero sum environments you should probably not run experiments what you should do if you are in a zero sum environment you should figure out how to get a positive sum and that's much more often possible than people imagine.
B
Toby, I'm not sure I've ever had quite such a broad ranging discussion. I'm not sure if most of your interviews quite cover the future of climate, Trump and Canada's relationship, the future of developers in organizations, but I've so enjoyed this. So thank you.
A
I mean it's like the things I wrestle with, like if you get me on a different time, I'll talk about different things. I just like look again, what would be awesome if there's like some people who like really disagreed with everything I said but are still listening at this point because that's all I want. It's all anyone wants. Let's get back to having conversations, Allow people to be wrong. I'm wrong all the time. It doesn't matter to you. This is fine. We can lower the temperature, we can realize there's some priors in society. Some things were load bearing. We've placed some things which worked. I've made very few comments on what we ought to be doing. I mostly talk about, talked about creating the boundary conditions in which people can just do things. That's the genius of the whole thing, the genius of the world. We inherited it like our ancestors created ever since the Enlightenment. For us, it's just that they created a sandbox in which people can do things. They take responsibility for doing things. They are personally accountable. They take personal accountability for the outcomes of this. They go to jail if they do something bad, but they are allowed to have property if they're right. The people. Everyone who builds something is making just like an incredible Faustian bargain with society here in a world that discriminates against builders in a way just on account of their products having worked. I own 6% of Shopify. That makes me incredibly wealthy. Yes, but that also means 94% of it are owned by other people. That's all of those people made a lot of money with the company. And that's not even talking about the customers and all the people employed by the customers of ours. Like there's, there's probably 10 million people working day to day on Shopify. Their job is to do the thing that Shopify asked them to do. Send out products, deal with customer relations, all these kind of things. Build new websites and so on. That was always there. And Shopify has brought it into existence in actual ways so it can be consumed. And we are not the only company. Many do it. And people vote right now and hopefully for a long time every month by paying the subscription, that Shopify's instantiation of this idea that needed to be pursued is the one that is valuable to them. And you know, there is a belief in society that when there's a good thing, there must be a counterreaction. It's some kind of misapplication of a Newtonian laws. And you know, some things are just good like, some things are just like super fucking good. And the downsides might even be describable, but they just don't pale in the face of all the good that comes.
B
It's like we said earlier though, which is like the demonization of wealth. A lot of people you see in America thinking that to gain and to have a bit billionaire, they must have stolen from someone who doesn't have money.
A
Yeah, show me one. You can't get to a billion dollars by stealing money. I mean, maybe you can maybe ask some instantiations, but then to talk about this specifically, the people who get their wealth by building companies have not stolen anything. They have created a product that people voted for. It's actually the most democratic thing that exists. It's vastly more democratic than any of our elections that we actually go doing. People shape the world around them by the way they allocate their money to products. Every time you buy something from a local shop, you're voting for the welfare and the future and the thriving of local shops in your area and not just the product that you purchase. And there's nothing bad about that shopkeeper because they are putting themselves out there. They're working extremely hard. It's an unrational act to start a company. You're working extremely hard for yourself instead of working less hard for someone. Someone else. But you're actually creating another thing. And other people get to have employment there and have the jobs that work according to their lifestyle. And so it's so weird that we are like putting this in contempt. And again, I'm very, very pro constructive criticism. But constructive criticism is itself something that someone builds, right? There are people who create excellent constructive criticism and I learn a lot from them. I'm fortunate in that I get a lot of constructive criticism even just as a public comment company CEO, you have some people write incredible memos externally that are really, really worth reading because they give you a perspective you didn't have and that's them building up a picture in the public mind about how to think about something. But there's also lazy and bad faith criticism or just like hot takes and this kind of stuff that is actually incredibly corrosive and should be had an incredible contempt by people and we don't. How many times do people who are saying something incredibly wrong look through the entire all the things people have published during the COVID times or even like climate panic pieces. How many times have you actually posted revisions to this? It's very rare. And so you realize it wasn't about truth, otherwise they would do it because that's the correct thing to do. If you were wrong, the ice caps did not melt. In fact, at the time frame we are at, we are in the years that they told us that the ice caps would be gone. Right? And so just like that doesn't mean there is no climate change. Climate change is all the time. It's just like it's not. But it's inducing panic. You're not allowed. I'm a very pro free speech. Free speech is a mechanism of self healing for everything else related to property and to classical Liberalism, this is why it's worth protecting. But there is no absolute free speech. You can't scream fire in a cinema in almost any place that you're going to the precinct afterwards. But somehow you can do it in media. You can do it in all sorts of. If a timeframe is long and then it's time.
B
Do you worry about that moving forwards when the most common response on Twitter is grok, is this true?
A
No. I think this is why I'm so bullish about the future. There was an effort mismatch in terms of bad faith acting. It's really easy to do. It's one assertion famously. It's a Stalinist kind of thing. It's like for every man there's a combination of words that will undo him. And so it doesn't need to be true, but it just exists. There's some accusation that is just plausible enough that the person disappears years afterwards especially. I mean, I think this was specifically a case in the Soviet Union. It's always true. Then there's a lot of collectivism around which is really just centralization of power with the state. Now the fact checking is very hard. It's an asynchronous warfare. It's a sort of information terrorism. To take a very absurdist position on it, proving that it's not true is a lot more work than saying the thing like this. And so you can. There's not that many bad faith actors. It's actually a small number, but they can be incredibly prolific and seed all the kind of important things. So I think AI is just going to. AI is moving the power back to good guys. I believe or not even that's actually a wrong framing. There's no good and bad. It's like everyone's good in their own local system and some people have a wrong system. And this is why we need conversations to arc them to the valuable ones in society.
B
I mean it's in the nicest way to be. You can't actually believe that there are malicious bad actors who will use. Use AI to exploit.
A
I didn't say this. I'm sorry. Balance, they had a lot of interest in. No, no, you're completely right. There's also especially so there's always a societal level and an individual level. On an individual level, which is the one we document, right. It's like on individual level there's going to be so much shit happening, like voice cloning, just like the hacking stuff. All software turns out to probably not be good enough in terms of security. That's going to be like a whole lot of bullshit we will have to deal with. Absolutely. However, the same models can also provide fixes for these kind of things. In fact, being able to apply as much intelligence in a form of artificial intelligence to the side of preventing fraud I think will shift. The balance will shift here. I think we're actually going to get in a much, much better way. Even claim testing is a statement. True. It's a thing that can be done by a council of models, especially Chinese trained model, Germany is trained, France like let's get everyone's opinion on something and just give a different perspective and synthesis. Look, building the thing I just said I can do by just going to one of those ghosty terminals taking the transcript of just the words two, three more steers and I can put this on the Internet and it will work. I would have to pay for it because the tokens are expensive right now. But suddenly we have a new institution which is like well see what everyone would think. What's the council saying about this claim and do some research. So we're going in a world where less of airwaves will be dominated by the bored people who act in bad faith because I think the other side has ability to push back. The Claude the Grok thing is sort of a primordial version of this is what I'm saying.
C
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B
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C
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Podcast: The Twenty Minute VC (20VC)
Host: Harry Stebbings
Guest: Tobi Lütke (Founder and CEO, Shopify)
Date: May 4, 2026
Episode Theme: A candid, sweeping conversation about the future of work and labor, the real impact of AI, critical views on charitable giving and government intervention, healthy criticism of societal narratives, and personal leadership philosophy.
In this wide-ranging and notably unfiltered episode, Harry Stebbings is joined by Shopify’s Tobi Lütke, who brings both humor and controversy to an honest discussion touching on AI’s role in labor markets, why charity often falls short, the inefficiencies inherent in governments, and social phenomena like “Trump Derangement Syndrome.” Lütke questions society’s approach to innovation, markets, and scrutiny—calling for clarity, constructive criticism, and accountability. The conversation is candid, philosophical, and rich in personal reflection, with Tobi providing insights as both a tech founder and a societal commentator.
Timestamps: [04:41], [05:18]
Long-Term Thinking vs. Short-Term Fears:
The "Heat Source" Metaphor for Leadership:
Timestamps: [17:34], [18:53], [19:54], [20:19]
Layoffs are Not About AI (Yet):
AI and Job Quality:
Entrepreneurship Remains Robust and AI-Benefiting:
Societal Adaptability:
Timestamps: [25:38], [26:06], [29:14]
Proper Target of Scrutiny:
Defending Builders and Entrepreneurs:
Critique of “Things That Sound Good” vs. Things that Work:
Timestamps: [29:14], [31:46], [32:28], [33:01]
The Dilemma of Charitable Dollars:
Suspicion Toward Not-for-Profits:
Timestamps: [34:18], [36:45], [43:07]
Favoring Prussian Economic Theory:
Criticism of Bureaucratic Inefficiency:
Praise for Certain Government Functions:
Timestamps: [37:31], [37:45], [38:54]
On Canada’s National Attitudes and US Relations:
Media and Public Discourse:
Timestamps: [17:25], [55:00]
Productivity at Shopify:
New Roles and Skills:
Timestamps: [47:06], [60:47]
On Being Wrong and Leadership:
Best Advice Ever Received:
On Balance, Society, and Constructive Criticism:
Tobi Lütke’s appearance on 20VC is a masterclass in candid, critical reflection on tech, economics, and society. He calls for a return to substance over appearance, personal accountability, and the relentless questioning of systems and assumptions—be it in markets, charity, or government. With nuanced optimism about AI and the future of labor, and a healthy skepticism of institutional narratives, his insights will resonate with founders, leaders, and critical thinkers alike.