Articles: Wisdom Collected from Interviews, Books, and More

This page shares my best articles to read on topics like creativity, decision making, strategy, and more. The central questions I explore are, “How can we learn the best of what others have mastered? And how can we become the best possible version of ourselves?”

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Daniel Scrivner

Tobi Lutke's Shopify Summit Speech on Solving New Problems

This is part of my collection of history's greatest speeches, which includes Ed Catmull's Keep Your Crises Small, General Patton's Speech to the Third Army, and Richard Hamming's You and Your Research. Browse them all →

Tobi Lutke, Shopify's Founder and CEO, gave this talk at Shopify's Summit in 2020 right at the start of the pandemic. As the team and company adjust to an entirely new world and outlook, Tobi sought to help the team adjust and act when encountering an entirely new box and problem to solve. Years later this speech still stands the test of time. It's an incredible look at the culture that defines Shopify and a great reminder of how to solve massive new problems one step at a time.

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Tobi Lutke's Shopify Summit Speech

Hey everyone. Welcome to Summit. As most of you know, we use Summit to talk about a lot of different topics, big ideas and big questions. So let's get started.

Let's get started with a big question. Who here remembers middle school? I do. Actually, ended up being a very formative experience of my life it turns out. I changed school around this time, and so everything was new. I remember how extremely frightening this actually was. New building, new floor plan, new teachers, classmates, social network. The kids in my class were into completely different things, all those of things which I needed to figure out and knew.

After a little while, I realized that there's two groups of children which had almost polar opposite experiences with it. And they can roughly analogous to the popular kids and the not so popular kids. That was a major insight for me back then. So I realized I was on the wrong side of this particular divide and I meant to rectify this, so I meant what I do when I try to figure out some kind of conundrum, even today. I went away and analyzed the situation as if that wouldn't already completely disqualify myself for being part of a popular kids, but I didn't know that yet.

What I eventually realized is that there was a commonality. All the popular kids were wearing Air Jordan sneakers. And I figured that if I could just acquire one such, I would then change my luck. Totally didn't work. Went exactly as badly as you can imagine because correlation is unequal causation, of course, we know this. And this is a really, really funny story from a perspective of adults whow have all kind of been in this environment. But when you're inside of a particular box of middle school, all of this is actually a fairly cohesive thought it turns out, or at least it was for me. Your mileage might vary. But over time you kind of figure it out. You get your ABCs, you get your math. School starts making sense and society in its infinite wisdom will start moving you through the experience. You will eventually be put on the conveyor belt of time and you'll be taken out of this particular box.

What happens when you're moving out of a box, out of a frame of reference? Well, you arrive in a new one obviously because there's a much bigger box around it. We all know this. We take everything we learned in a previous one and take it with us. It's actually a thing that you can almost physically look at. Suddenly your entire world fits into something you can reason about and see in front of you. It doesn't look that complicated anymore at this point. It actually looks simple, so you take it and you say, "Okay, everything I learned I'm going to put into my backpack." This is a backpack of knowledge. This is the thing you build as you're going through life, your lived life experience and the backpack are full of good ideas.

After you do this, you look around, it's nebulous here. It's really scary. In my case after middle school, I started an apprenticeship. It doesn't really matter for this story. You did something else, secondary education of some form, university college. In my case, there was a completely new hierarchy, more players, more complex social interactions. Once again, more of everything. It was a company and then the school still. Lots of new things mattered and it was really powerful experience, but I couldn't explain this new box at all with what I already knew from the previous one. The world thing felt nebulous, uncomfortable, unfamiliar, scary, and you couldn't turn back. In fact, it would be literally illegal to go back to middle school, so you can't. You kind of have to go on.

Slowly, you start figuring out. In my case, there was I understood, started understanding the players and the people and the person who was assigned to my apprenticeship. I had to do some computer programming and eventually I got some feedback that I was going well. And slowly and surely, I sort of understood what this particular part of my life, this particular world I was in, felt like. Things became clearer. It was a huge relief.

Eventually, it actually became rather comfortable. Once you know how to be successful by the narrative of the world you are in, that felt really, really, really good. It feels like you have arrived somewhere. You don't know that there's anything larger yet, but even in this case, time alone and the way society is structured, it'll move you forward. You'll find an exit and it's not too hard to get there because you will be deposited in a place that has been designed and prepared for you, something you've been sold on your entire life. We'll get back there.

Let me acknowledge that this is not a new story I'm telling, a story about being stuck in some kind of frame of reference. Taking it for the wall truth only to figure out that something bigger lies around it is not a new story clearly. In fact, it's at a core a lot of society, told originally two and a half thousand years ago in the allegory of a cave, which is part of Plato's Republic. The allegory goes like this. People are sitting in front, stroking at a wall in a cave. Behind them is a source of light. That's all they ever did. That's the entire reality. I've never seen anything else before.

Sometimes objects appear between the light source and the people. Let's say a squirrel might walk by. A squirrel is beautiful. Well, if you like rodents anyways. But the shadow of a squirrel is a diminished form. It is not the same thing. In the allegory, at some point someone gets up and realizes what's going on. They walk up out the steps and leave the cave seeing sunlight for first time, standing in for the concept of enlightenment of course. Seeing all the forms that they only have seen shadows of for first time in their real full self.

The story actually continues. The person who left the cave to come back and try to tell everyone what they're missing and the people not reacting really well to this. It turns out that people are kind of hard to get out of a comfortable. This is for reality they know. Why change it? It's been working for them all along. It's a decision between comfort or discomfort, but truth, which is a hard decision to make. It's a real moral dilemma.

Of course, we see this story a lot. Let's just take the movies. Truman is stuck in a TV show that he got born into and eventually finds the exit. In The Lego Movie, and it eventually makes it out of a Lego world by self-sacrifice and finds themselves at the floor of a basement next to a Lego table. Sorry for spoilers. It's a great movie. And then most pure of all them all is a Matrix of course. It's the Manhattan of the '90s. If you take the blue pill or is it going to be some godforsaken spaceship in the sewers being chased by robots in some post-apocalyptic world, but truth. It's your choice.

So a lot of our stories in society are based on this. It's a story again of comfort versus discomfort plus truth, but the problem I have with a story is that it's a divisive story. It in the wave a cave is being told, it's really just the enlightened versus the not enlightened. And I would like to offer that this becomes a much better story once you work off a infinite set of boxes. 'll get back to that.

So real life, the box I promised and the box that everyone's being deposited into. The standard orthodoxy is to go from primary school to secondary school to real life. This is a box where society will tell you that you have arrived and it is a trap. You had deposited here because that's where we are the most productive members of society. The entire narrative is one of cause and effect. In fact, it doesn't even have a property of a nebulous parts. It's kind of all revealed once you arrive again because you've been taught how this works. You get good grades, you get your education, you marry, you get 1.9 for your children. You work hard, you get your promotions, you'll eventually retire and then I guess go on cruises or something. That is the story that a lot of people are told. And a lot of people decide to stay in this again because of a comfort.

I don't think we have too many people here, if any, who are in this. I think at some point, this is too basic, it's too industrial revolution to really hold up the test of time. We have too many information because the way we reason about this is based on this backpack I keep talking about, this backpack full of ideas. I've been really concerned with this thing. I think I've built a good backpack for myself over the years and it aided me really, really well in my own journey. Whenever I've encountered something that was really meaningful and really caught into questions, things that I've previously thought were true, I often build summer talks around them. This is exactly what I did. I took the concepts. I tried to turn them into a story and share them with you because I think this is the way, this is one of the ingredients that personal growth is made from.

Once you have the right tools, you can spot the cracks, something you can't explain. Systems thinking alone cures you of cause and effect thinking, which at some point breaks down the snakes and ladders box. In my case, I had the tool. I found this crack and I used it to get out. This was an exit of entrepreneurship. No one helps you with this. You have to do this yourself and you have to commit yourself to it.

This is really my bird view. It's an infinite set of boxes to be traversed in pursuit of personal growth. And again, I think this is my problem with Plato's allegory. It is a much better way to think about everyone being part on their own journey somewhere in this. We are all sitting in the cave looking at a wall of some box. Some of us boxes are bigger than others, but the growth comes from the traversal and the forward momentum. Going from box to box is the only way to become the best version of yourself.

This brings me back to my own story, from entrepreneurship to lifestyle company. We entered 2004 here. I just left the snakes and ladder box myself. It's hard for me to convey how frightening this is. This one has no light. You can't even see the first step you take. It's nebulous, it's dark, and you have a very dim flashlight that doesn't reach very far. It's so scary that you will want to go back because where you come from, you understood everything. You're coming from comfort and you're trading discomfort. It's a hard choice to make.

I initially discovered snowboards and Ruby and I finagled those things together to an online store with Snow Devil. And that gave me the first semblance of some success in it. That didn't end up being the entire box. It just kept going by taking a step, another step into the discomfort. It revealed itself to be something very different from what I set out to do. Snow Devil seemed very important to me, but really having other people start their own Snow Devils ends up being a much, much, much more worthwhile pursuit.

I set myself a goal of building the world's best 22 people company. That was what I was going for. This is called a lifestyle company. Along the way, I encountered so many challenges that I didn't even know the names of when I started. I had to do payroll, I had to do finance, I had to do some financing. I had board meetings with the gentleman on the couch here. I had to deal with bangs and all these kind of things. Again, when I went into this initially, the only marketable skill that I had was programming and the ability to learn things. But eventually step by step, I picked up the skill and put them into my backpack. I am not immune to the pull of a comfortable box. And I realize I'm talking to 6,000 people here who know how this movie ends, like we know where this went. It is really, really hard for me to convey how unlikely this was.

I'm a high school dropout who left the snakes and ladders box and found success in spite of it. That felt good. We are now in 2009, 2010, so like exactly a decade ago, a decade we entered with 22 people and I thought I made it. Whatever that means. Imagine how concerned I was when I saw the crack in this idea. I was so comfortable with what I had. I remember the strife. I don't want to trivialize this thing, getting even to this point. So if I was a week away from not being able to meet payroll for a year and a half, there was so much hardship that I'm skipping over and it just felt like I finally earned the reward for all this strife that now things are sort of understood and easy.

So I said "Nein danke." Success just felt too good. For the first time I could explain my parents what I was doing. And after all these years of striving, I understood what it took. That's the dangerous part. All the signs were there. The arguments for staying small started to not make so much sense anymore. They were just not that convincing anymore. Some experiments we did with some extra money just showed that what Shopify wanted from us was so much more. We were not giving it the thing that we could, and that was my fault because I held it back because I really, really wanted this comfort.

I realized something incredibly important at this point. Feeling comfortable is the most dangerous part of a journey, not the goal. That's a new leap. So the 22 of us decided this together. With all the evidence we said, "You know what? Yes, we have a sure thing. Yes, we could pay dividends. Yes, we have reached profitability, but maybe we should go and give those venture capitalists a callback. Maybe we should talk to them again and see what a Shopify would be a proper venture might look like." It's sort of a not really too good, well understood part of a Shopify history, just how different those times are.

So the 22 of us took the sure thing we had and basically bought a venture lottery ticket. Because we failed, Shopify wanted that from us. All of us need to understand this. This is a super important thing for this company to fully embrace and understand because we need the empathy to what it feels like for people who are going through this discomfort. Why? Because our very product is the thing that does it to people, isn't it? That entrepreneurship crack is what a lot of our merchants take. And they're confused. Whatever box they're leaving is next and letters or further on. That box, they're new. You don't leave a box that you're not comfortable in. That box, they're new. It was bright, lit and understood and suddenly they say, "I don't know what's going on. I'm scared."

When they call us, they are not asking us about CNAMES. They're not asking us about domains or tax settings. Those are [inaudible 00:19:49]. What they actually want to know from us is, "Shopify, I'm scared. This doesn't feel the way it's been sold to me. Do you get me? Are you with me? Are you here for me?" We say yes, of course. In fact, the very person you're probably currently talking on is themselves going through a box, understanding full well what that feels like and what you're going through. We have that empathy. We understand you, we get you.

Everyone everywhere goes through this journey, trying to navigate their own box, especially our merchants. Now of course, some people choose comfort instead of growth and eventually return to a previous box of theirs, leaving the journey of boxes forever. Immediately to mind comes family reunions. There's always someone who left the journey of boxes way too early and can explain the entire word with very simple terms from the vantage point of a tiny little box. That's not fast. We don't do that here.

I think it's worth talking about what a company really is. I think there's a lot of people who think that a company is this monolithic thing but has its own interests, its own things, the things it wants to do. To me, I think a company is a collective term. What a company is and how it's really created is that people who have been committing themselves to a life of learning and are developing an appreciation for leaning into this discomfort. And they're taking all their boxes and all the backpacks and start pushing them together. Putting our boxes together, helping each other grow.

We create this giant ad hoc Frankenstein legal contraption of individual skills, if you will. We help each other and welcome each other. Some of the boxes become bigger and some new ones are added. That to me is truly what a company is, but some total of all the boxes and the backpacks of everyone combined. The point I'm trying to make here, and I hope the point that you're going to take away from this talk, is to be suspicious of comfort. This is a tough thing to say because it completely rails against the orthodoxy.

The status quo is that we all live in a world which is obsessed with pain avoidance. Every time you hear someone talk about imposter syndrome, this is what's going on, it's people using medical terms to describe the effect of, "I don't know how everything can be solved around me," which is actually the substrate that all personal growth is made from. We have bad stories around us around that, it doesn't match my experience. My experience has been that it's an infinite circle cycle of discomfort leading eventually into a breather, which then commits you to the next box.

Companies themselves are in such a series of boxes. I told you the story of a Shopify lifestyle company, 2004 to 2010 already. The next phase is we took the venture money, and it's the venture years. The success of all of us there is hard for me to fathom even just now. We brought on thousands of people, a million merchants. We broke out of a swim lane of e-commerce software. We used multi-channel and transformed to mobile. At some point along this decade, we actually IPO'ed. And you know what? It wasn't that big of a deal. Why? Because the total size of a company, all the boxes combined and all the backpacks of skills just kind of made it so. We were equal to a task. So many incredible things that happened and yet we mastered it. We sailed through it. But that box has ended. I sense the discomfort.

We are going to release a consumer brand with Sharp and we are building a global fulfillment network with SFN amongst all these incredible other things that you're going to be hearing about today. We are doing something very, very ambitious things. But also in the last couple of weeks you've gotten an email from me about a checkout code red where we have to look after our perimeter, and a marketing reboot, which can be difficult for a lot of people. This is why I want to repeat this talk. I've given a talk much like this before. In fact, exactly a decade ago.

This is a story that over 22 people who entered the last decade knew. It's something we talked over drinks and we talked over pizza about. It is an alternative version of how to think about personal growth. That is a story that stood the test of time because I think it has helped a lot of individuals. And I think it explains better where the discomfort comes from right now.

Shopify is now in one of the biggest boxes that companies have ever achieved to reach. It may not have been that many other companies that got to this point. And we are rolling with some of the biggest and the baddest companies in the world and we are the smallest. That is uncomfortable. But it's what we are good at. And we have all the backpacks and all the ideas of everyone combined.

I have no idea what else is in the nebula, but we'll find out. We'll lean into it step by step into this discomfort, step by step into this uncertainty and step by step into this ambiguity. Together we will become and build the best version of Shopify. That is what Shopify wants from us. This box we just read is probably not even the last one. I'm absolutely thrilled with where we are at.

Later in the day you'll hear about product things that we are planning and all the plans for the next year. This company has so such unbelievable potential and I'm really, really, really proud of us all for getting it to this point. We are all unbelievably lucky. We are taking part of something that is so rare and it's kind of one of the best things this planet has to offer. We are on a journey doing meaningful and difficult things, surrounded by friends, and we get to do it every day. Thank you.

About the author

Daniel Scrivner is an award-winner designer and angel investor. He's led design work at Apple, Square, and now ClassDojo. He's an early investor in Notion,, and Anduril. He founded Ligature: The Design VC and Outlier Academy. Daniel has interviewed the world’s leading founders and investors including Scott Belsky, Luke Gromen, Kevin Kelly, Gokul Rajaram, and Brian Scudamore.

Last updated
Apr 30, 2024

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