The Shawn Ryan Show
#261 Tobi Lütke - CEO of Shopify: How Shopify Became a Cheat Code for Entrepreneurs
11 Dec 2025
Chapter 1: What is discussed at the start of this section?
Toby Luecke, welcome to the show.
I'm so excited to be here.
Man, I've been excited about this for a long time. But, you know, I want to start this off. I feel like I owe you a thank you. I don't feel like I owe you a thank you. How so? Because what you've done with Shopify has just... it is what brought success to my business and so many others. And so I'll just give you a story.
I started this around 2015, actually in December of 2015, so almost exactly 10 years ago. And this kind of started as a tactical training company. And I had just left CIA, contracting for the CIA. I didn't really know what I was going to do. And I've always wanted to you know, get into entrepreneurship.
So I started this company and, but I had no money and web develop, you know, to create a website back then was, I mean, it was, it was, for me, it was a lot of money. I mean, it was, if I remember right, it was about 20, $25,000 to get a website made. And I was like, man, I don't have money. Yeah. 25,000. But I did it. I did it.
And I got a shitty website from a developer who I needed to call and have meetings with about every day, every time I wanted a new product out there. And I was just selling courses. And, you know, of course, every time I wanted to add another product, that was several thousand more dollars. And then I think it was TV. I was watching TV and I saw a Shopify ad pop up.
And it was talking about the do-it-yourself stuff. And I was like, man, maybe I should try this. And so I did.
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Chapter 2: How did Tobi Lütke's journey into entrepreneurship begin?
You did. I got the free trial. I tried it. And I was like, holy shit, I just built an entire website in like four hours. That's amazing. And that was 10 years ago. And we're still on the platform to this day. So if I have a story like that, and we started, so I started selling my courses on there and then the really, the big win for me on Shopify was. Dummy bears. So. Which we still sell today.
That's a bag for you made here in the USA, sold on Shopify. Love it. Such a good product. But it just, I mean, it's just, it like unleashed a cheat code to entrepreneurship by being able to sell our stuff because web developers would hold us hostage. And so thank you for doing that.
I mean, that's so meaningful to me because, again, this is my favorite story because I think entrepreneurship is incredible and incredibly important. It's so important for society that people can reach for independence, that people can
Instead of complaining about something not existing, they can actually do something about it, they can build something, and there's this wonderful market, you participate in it. If the market deems it to be of value, then it funnels coin back to you, so you can do more of this thing, and it all kind of virtuously grows in a virtuous cycle. It's just so honest.
It's such a form of self-expression. It's such a way to not just gain, but also give back. And it's a perfectly positive sum. So from a fully philosophical perspective,
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Chapter 3: What challenges did Tobi face when starting his first business?
It's one of the greatest journeys people can go on, most people, and it does require a good deal of courage to put yourself out there, but, like, I've started early my teenage years with small businesses and just selling products and these kind of things. And I've discovered this for myself. And then later, I'm sure we're going to get into some of these things with my snowboard shop and so on.
I love that after discovering this sort of gift and trying to figure out how to, in my own mind, how to build these businesses, that now we get to spend all our time really day and night
creating a product that we can share which itself causes other people to share their products right like this is a wonderful thing it says millions of businesses out there that provide employment that create new products and so it's but it's the important thing there from my perspective is I want to thank you for building something.
Because as you know, especially for the builders, there's nothing in the world more gratifying than someone using the product or being delighted by the product. So I think that's honestly the best thing about the world of retail commerce. It's accessible, it's available, and it's really, really, really... There's a lot of camaraderie. Because everyone has so much in common with each other.
Everyone's engaged in it. And they respect each other for doing this.
So yes. It's, I mean, you have just, I mean, I can't just, I just can't stress it enough. I mean, you know, it's not like I just took that $25,000, you know, and spent that on bullshit. Like, as an entrepreneur, it's a huge lift.
You could have called it at this moment, and then you would have been $25,000. $25,000 for $100,000.
But I mean, I see, I just have saved so much of web development and, you know, in taking what I saved and putting that into, you know, product or other areas of the business. Because, I mean, if I remember that I'm off on these numbers, but let's say 20, 25,000 to build a website, then Shopify. I find Shopify and it's like $20 a month and it's like, holy shit.
So I was able to take all those all that capital and put it towards something else and build something real. And and so I'm just one of probably
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Chapter 4: How did Tobi transition from a snowboard shop to Shopify?
And once again, like, thank you for what you've built. We've been using that for 10 years. And, you know, I want to do a... you know, a journey on how you build Shopify. And then we have just a whole bunch of topics to cover that all have to do with an entrepreneurship. But but before we get too in the weeds on your story, of a Patreon account, built a subscription network.
We've turned it into quite to the community. And so one of the things that we do is we offer them the opportunity to ask every guest a question. This is from Eric Alger. What's the single most overrated thing in tech entrepreneurship today?
Networking events.
Networking events. That is not what I was expecting you to say, but I can totally see where you're going with this.
I just like, I try, and I really, really try, and I try to make them work. But it's just like, I can't. I'm like, maybe I'm the wrong person to try. I'm trying to like, what's, this is sort of a flippant answer, but what can I share that's actually actionable? I'll stay on the topic and maybe make a modification. Advice. I think advice is overrated. I think gut instinct is underrated.
I think too many companies are building slightly different versions of something that someone else already sort of discovered or slightly different takes on things and do market research and A-B test everything. And at least in my corner of the world in retail industry, you see more
self-confident this thing needs to exist and i think that would be it would be nice if tech becomes a little bit more weird a little bit more eccentric and a little bit more um uh self-confident and leaning into uniqueness rather than uh derivatives more again i think the aih makes this so much more more attractable for most so i'd love more of that
Right on, right on. I love that answer. We're going to take a quick break real quick, and then we'll get into your life story. All right, everybody, I'm really excited to tell you about this. I've partnered with this company called Beam, brought a new partner on the show. That rarely happens. It is extremely hard to get a slot on this show, but they are the makers of Dream Nighttime Coco.
I'm really excited about this partnership. I've struggled with sleep. Pretty much my entire adult life, and this stuff actually works. Sleep has been a problem for me for years, and when you're exhausted, everything suffers. Your concentration drops, your reaction's slow, and your work takes a hit. With the podcast, I'm sitting down with people who deserve my full attention
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Chapter 5: How does Shopify integrate AI to assist entrepreneurs?
And so, AI. Like we have this integrated in Shopify, it's called Sidekick. Having a... um you know infinitely patient extremely knowledgeable um you know kind non-judgmental ai sidekick as part of your entrepreneurial journey is extremely game-changing from our perspective This exists, this is an integrated job for everyone gets access to it.
And the conversations people have with their tailors are just like, it's remarkable. The big businesses ask it to run reports, the new entrepreneurs ask like,
Chapter 6: What are the benefits of AI for solo entrepreneurs?
where do i have to go in minneapolis to register my business you know it's like how do i open a bank account how you know like it's it's all the kind of questions that's going to be embedded inside of shopify it already is it's hundreds of thousands people are using it uh daily it's just like it's it's like um in fact you can ask it to do jobs for you you can say hey here's my uh here's i got the
got a pdf here of my supplier for the uh summer um collection for products can you please create the products and add them um and um you know just it will go and do it and it's like i hope it's doing a great job doing it like it probably might it might get some things wrong so you you will definitely show your review screen for everything but like it's it's increasingly able to um just join your team as a team member right and um
Again, especially for the solo entrepreneurs, that is an incredible change because now they have, I mean, a team of one. Like, that's cool.
Wow. They literally have an assistant.
Yeah, they have an assistant.
Holy shit. I can't wait. I got to go ask my guys if we're using this.
You should check it out.
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Chapter 7: How does Tobi Lütke define effective team structures?
It's fun to have conversations with. I'm super biased here, but I'm a really, really big fan of this. Again, most of the intelligence there comes from the wonderful advances of... labs like OpenAI and Anthropic and others. But like, you know, Shopify is a bridge company, fundamentally. We are a bridge between the world of, the global world of commerce and the technology world.
Like, our job is to go and get the best things that the technology industry can do and make them available for people who are trying to self-actualize. This is our native habitat.
And so that power that we are getting for helping people with AI in doing this and what we can deliver to the people who are just going to sign up tonight for and trying to build a business is just absolutely remarkable. And that's why I say it's still underhyped.
That's amazing. That is, wow. That's incredible. Let's take a quick break. When we come back, I'd like to talk about how you run your team. I know you run it lean and would like to just move into that. It's okay. My days don't slow down.
Chapter 8: What advice does Tobi Lütke have for aspiring entrepreneurs in 2026?
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Ready to upgrade your eyewear? Check them out for yourself at roka.com and use code SRS for 20% off site-wide at checkout. That's R-O-K-A dot com. All right, Toby, we're back from the break. We're getting ready to dive into how you run your team. So I, you know, I was picking through your outline and saw that you'd like to run small and lean teams. Who doesn't?
And this is a growing pain that I'm trying to figure out right now if we want to go and we want to bring everything in house, which is kind of originally what I thought I wanted to do at the beginning of the year. And now I'm starting to think, I don't know if I like all these people running around and I don't want to get, I don't really want to get any bigger in deal.
I like to keep, I think the way I'm going is I like to keep my internal team extremely small and lean and nimble, and then start to outsource more and more to other companies, not individuals, because I think companies might, hopefully, care more about their reputation than what I have been dealing with. So anyways, I just want to get your thoughts on that.
Yeah, I mean, at the end of the day, Everything is about the team. Like a company is actually not a thing, really, if you think about it. A company is like a collection of individuals that we just call a company. Every company is getting... Like a company can't gain skills by itself.
It's just the individuals in the company might develop a skill or you might bring in someone new to gain a new skill. So it's kind of like... Honestly, the beautiful thing about companies is that they get to align a lot of people's incentives all in the same direction. And then everyone gets to spend their day together doing hard things, hopefully, unique things and so on and so on.
Reality is, there's a huge amount of complexity in just getting these incentives aligned. It's so often that lots of people just end up grinding against each other, and all the energy is diffused by the grinding noise they make, by just being in each other's way. And the solution to this is like, I mean, it's like one of two things, right?
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