20VC: Shopify Founder Tobi Lütke on Why Micromanagement is Good | Why You Will Learn More From Studying World of Warcraft Guilds Than You Will Companies | Why Happiness is BS; Lessons on Marriage, Fatherhood & Decision-Making Quality

3 Apr 2023 · 57 min

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In short

Podcast Summary: The Twenty Minute VC (20VC) with Tobi Lütke

Episode Overview Episode Title: 20VC: Shopify Founder Tobi Lütke on Micromanagement, Learning from World of Warcraft, Happiness, and More Host: Harry Stebbings Guest: Tobi Lütke, CEO and Co-Founder of Shopify Date: [Insert Date]

In this episode, Tobi Lütke discusses his journey from a small-town German boy to the CEO of Shopify, sharing insights on leadership, decision-making, and the complexities of happiness.

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Key Topics Discussed

  1. Tobi's Background and Early Aspirations
  2. Childhood Ambitions: Tobi expresses his early passion for programming, sparked by receiving his first computer at age six.
  3. Influence of Mentorship: He emphasizes the importance of mentorship in personal and professional growth, reflecting on who he learned from in his formative years.
  1. Learning from Non-Traditional Sources
  2. World of Warcraft as a Learning Model:
  3. Tobi argues that one can learn more about teamwork and coordination from World of Warcraft guilds than from studying traditional companies.
  4. He believes that humans often struggle with effective company building and that studying gaming communities can provide insights into better organizational strategies.
  1. Creativity and Constraints in Business
  2. Embracing Constraints:
  3. Tobi posits that constraints foster creativity, distinguishing between enforced and artificial constraints.
  4. He explains how leaders can use constraints to enhance productivity and innovation within their teams.
  1. Decision-Making and Prioritization
  2. Reflecting on Decision Processes:
  3. Tobi shares his evolving decision-making framework, critiquing common fallacies like the sunk cost fallacy and advocating for a truth-seeking approach over a purely logical consistency-driven one.
  4. Learning and Prioritizing:
  5. He discusses his method for choosing what to learn and prioritize in his role, emphasizing the importance of being open to new information and adapting accordingly.
  1. Happiness and Life Goals
  2. Happiness vs. Contentment:
  3. Tobi argues that happiness is transient and often misleading as a goal, advocating instead for contentment as a more sustainable and fulfilling pursuit.
  4. Work-Life Harmony:
  5. He challenges the notion of work-life balance, suggesting that integrating work with life can lead to more meaningful experiences.
  1. Physical Presence in the Workplace
  2. In-Person vs. Remote Work:
  3. Tobi strongly supports physical proximity in teams, believing it leads to better collaboration and morale, while acknowledging the challenges of remote work.
  4. The Impact of COVID-19:
  5. The pandemic shifted Shopify's operational strategy toward a more remote-focused approach, which he reflects on as a significant change based on market realities.
  1. Leadership Philosophy
  2. Micromanagement vs. Empowerment:
  3. Tobi discusses the balance between providing oversight and empowering team members, emphasizing the need to trust employees while ensuring they have the right support.
  4. Cultural and Communication Dynamics:
  5. He reflects on the importance of culture in effective leadership and the necessity of clear communication within teams for collaborative success.

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Key Takeaways

  • Curiosity Drives Learning: Tobi stresses the value of following curiosity and engaging with diverse sources of knowledge.
  • Constraints Foster Innovation: Embracing constraints can lead to creative solutions and stronger team dynamics.
  • Seek Contentment Over Happiness: Contentment provides a more stable foundation for life satisfaction than the fleeting nature of happiness.
  • Trust in Leadership: Effective leaders balance oversight with trust, creating environments where employees can thrive.

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Conclusion This episode features Tobi Lütke sharing profound insights from his extensive experience leading Shopify, touching on themes of creativity, leadership, and the nature of happiness. His unique perspectives encourage a deeper examination of traditional business practices and promote a more holistic approach to work and life.

For more episodes, visit [Twenty Minute VC](http://www.20vc.com).

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Transcript

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0:00I think you can learn more by studying word of word -of -wark -reft -raiding -girds. Then you can learn from studying companies about coordination and what great looks like. There's probably no singular idea that has destroyed more business value on plow -dove. Then uh, third year that my cramagement is about to end. This is 20VC with me Harry Stabbingson. This show is the definition of persistence. I have to say I sent my first emails to Toby asking him to come on the show on the 17th of May 2020. It took about three years, but wow, this show is incredible. I also heard him on every other podcast he's done and made sure that we didn't cover any of the same content.

0:35And so with that, I'm thrilled to welcome Toby Lutker, co -founder and CEO at Shopify, the global leader allowing anyone to start and grow their e -commerce business. Over an incredible 18 years, Toby has scaled Shopify to 10 % of total US e -commerce, millions of merchants in over 170 countries and a market cab today of over $60 billion. dollars. But before we dive into the show's day, secure frame is the leading all -in -one platform for automated security and privacy compliance. Secure frame simplifies and streamlines, the process of getting and staying compliant to the most rigorous global privacy and security standards, like SOC -2, ISO -2701, HIPER, GDPR and others.

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3:31Tobi, I'm so excited for this. I had so many great things from Glenn, from Luke, from Jeremy, at Basima, from so many others, so thank you so much for joining me today. Oh, it's an absolute pleasure. I was looking forward to this. And he thought we'd start with something a little bit off the bat, to be honest, Toby. And so I thought we'd start with, think back to when you're a child. What did you want to be when you grew up? Hey, so I got lucky. I got really, really, really lucky. My parents got a computer, and I was six years old, and I knew there was nothing else. Like that would be more interesting.

4:02I learned programming before I knew that was a thing or a term. It must have been like 12 years old or so, but there's just no chance I'm going to do anything other than program all day. Can you guys walk up to VATED you so much? You mentioned 6 when you got your first computer. Was it about it that made you so interested? I'm at first time sitting in front of it and just typing any letter and seeing it on a screen was just magic. I'm curious about everything. I hate black boxes. Everything is understandable and everything is way more interesting than it seems. I think people need fontiers. I think entrepreneurs need fontiers.

4:33There's a need for reaching for something that could lead to value in a good around us. It was never questioned in my mind. as like there's basically like spending time on a computer was 10x to 100x more interesting a little anything else that could possibly happen in my life for the first 10 -15 years of my life. You mentioned not growing up in the van and being in the German school system and hating blank boxes. I always think we're kind of all functions of our history so it's be I'm secretly an armchair psychologist who never got a psychology degree or any degree at all actually Toby. But my question is what do you think you're running from when you reflect on that or being a functions of our history.

5:11Bottom is something I like to avoid ignorance. It's more magnetic for me. Honestly, there's more magnetism in the direction of them going when there's a reverse polarity in which place I'm coming from. I just have a strong sense that the goal in life is try to become the best version of yourself. It sounds like super fortune cookie, but as if at the end of life you meet the person you could have become, the work of life is really try to minimize the diff between that that person and the one that actually showed up. Not understanding a thing feels almost amoral to me. We've got these incredible brains.

5:43These brains run a model of plan Earth, which we've been constantly interrogating. I want that model to be right. Therefore, every single thing, every single time I get to dig into something, into learning something, I can update this model. And the nice thing is, first of all, that's super fun. Second, that model is the one I work around with. I go into every one of my meetings with. I go into every encounter, every situation I hold up to every problem that I need to solve. At the quality of all decisions is simply how correct, how close to the truth is that model of a world that I've been developing.

6:15And I want to be able to reason about the new Swing Svet exist in the world. I need to not treat transformer models as a black boxer. Like I need to understand for this, because I was like, I cannot show up to a meeting with my teams and have a good chance of reasoning with them about not just what is sort of a colonial next task, but what's the very best thing we could be doing. What is the new thing that all of us unlocks? It has been driving me every step of our way. I mean, you just gave me so much say, I would love to break it down into kind of three steps, though, which is like selection of learning, process of learning and decision making post learning.

6:48If we think about selection of learning, I heard you say on a different show that actually when it comes to kind of great founders, the best founders that they can do is subtraction. When you think about focus and deciding what you choose to learn. How do you determine what you should choose to learn versus bluntly, maybe interesting, but a distraction. Right, so there's a thing called product market fit. I actually think a more sometimes important thing in this context is actually founder market fit. I think you can play this game at more layers. I probably have something weird like curiosity slash times fit.

7:25I am interested in literally everything that can get value. It's very it's a very bizarre thing, when I get interested in something, I know there's value hidden in it. I follow my curiosity. I think there's a curiosity itself, and so being the product of a intrinsic ability to spot value around corners, which is hard to put into words. Can I ask you, what do you do when the value is ambiguous? And I think about currently, obviously, I create content. When you're debating on a new content strategy, the kind of terminal value is actually ambiguous. It may work, it may not work. How do you think about dedicating time when ambiguous terminal value is a potential outcome.

8:01Well, times you find resource, attentions you find resource, so you have to create an evaluation function that you run over your ideas. I think effort is a big factor. Also, the reversibility is a big factor. If something is easy to reverse and not a lot of effort to try to give it a goal because the fact that you think the value is ambiguous is a whole in your model of the plan of. So filling that whole means that afterwards can avoid similar paths because you will encounter the same idea over and over again. When you're developing a piece of content, you could make a decision to commit yourself to a deep research subject about having many meetings, many conversations, maybe reading some books, or you could say, well, I'm trying to try this new channel and maybe I'm going to reuse some content or maybe it would work in this channel or something I can do in an afternoon and then you time box it.

8:51Then my objective is to find out if something is of value. I try to figure out If everything I already got and an afternoon of time, how can I get basically a scorecard before you go deeper into this? I think that helps a lot. I find my goal setting very difficult because a lot of goals can be gameable. You said about the scorecard there. You can give most things a goal that is entirely gameable. How do you tie true outcomes to the goals that you set to ensure that you are actually moving the ball down the field, not just hitting a goal? Yeah, that's a right question. I'm more of a craft person than a scientist.

9:27Real artist ship. I like to think that wisdom That should be pretty intrinsically motivated, but the key is afterwards to take to take that and and and create something that other people can consume if you just I re -toward some some new knowledge then I think you don't actually add a lot in your world You consume I like building. I like creating going on a journey to gain some knowledge Figging out something new, but when turning it immediately into something that other people that you can shave our people is a key If this hypothesis is right, then I get to do a thing where then many, many more people can appreciate it.

10:00If you can't do the end of the sentence, I would don't grade it quite a bit, to take another side of it. At some point I was like, I need hobbies again, to pick up learning instrument guitar and play band poorly. You know, that synth seemed entirely intrinsically motivated for my own purposes, but I actually learned a lot about how to form great teams from the way it works. you know how to like I learned a lot about creativity like improvisation or like over a key What did you learn about building great teams from being in a band and learning music again? I a lot of lessons about leadership because like most pronouns in jazz there's a basic contract like artists real artists Well always talk about attorney over playing canvas right like this is actually not what leads to creativity Creativity always comes from constraints.

10:43I've been in many meeting meetings where people say I wish you could do this thing where it would be completely unconstrained by like a budgetary time. And I'm like, yeah, but that's hallucination. That's our craftsmanship. That's not on the, that's not engineering. I think the older crafts have this totally figured out. Like in, in blues, you were set a meter, like you were set a temple, you would presumably set a beat and you would set a key. And then afterwards, people improvise over that. Different people might do a solo, different people like, you're creating a new piece of music with every note.

11:14It's deeply creative, but the creativity comes out of the constraints that they're set. And then, if you really know what you're doing, and this is where it gets really fun, you get to violate some of those constraints. Like, you can do a key check. You can go from minor to major. If everyone's good at what they're doing, they'll follow. Or create some dissonance in the scale, which actually leads to, if you resolve it right, it loads to interesting things. This is, I think, what the best teams do everywhere. They are greedy for constraints. They want to understand how can we restrict our space So that we get to get started, develop something, feel each other out, develop an appreciation for each of us Updates and skills, right?

11:50Like it's a different piece of music. Apparently we show us up to your band Can I think about constraints in this way? Is it purely financial constraints or are there other types of things? No, if you take a engineering project time is one of the best constraints time boxing Like in Shopify every project costs multiple phases. There's a prototype phase There's like there's a proposal phase before that if proposals accepted you go to project type phase build and releasing. The prototype phase is ideally time constraint and people constraint. You can only do it with three people. You've got maximum of it six weeks.

12:23It should actually be less. It's sort of me ended upwards. In fact, it should probably be a week. And then next week you should start from scratch to try something else and do this multiple times. That is some of the best code I ever wrote. We did this in peer programming and we set ourselves constraints like every single day we have to throw away all source code other than the unit as and we would ship the feature the day we could implement the entire feature in that day. You really really really really get good code if you do that. So I think one of the best applications of creativity in the world of creation is actually creating creative constraints.

12:57Also creative constraints and how does that differ from a non creative constraint? I think all that it's just a mindset. This is how you react to constraints. I think I think every constraint is creative constraint. People who complain about constraints have an incomplete mental model about the creative process. How do you impose constraints now in a world where bluntly you have much less? When you are a startup running out of cash, you have real constraints on time, you have runway. When you have like time restraints on engineers, it's because you can't afford any more engineers. You have no money to hire someone.

13:28Bluntly you're not running out of money. You don't have necessary restraints, but you can't hire an incremental engineer. engineer, how do you create artificial constraints and make them real? I think there are many ways to do it. I mean, culture is the best. The project management system, the Shopify has, which manages the phases of these projects and sort of a central roadmap, places constraints. So some of them can be tool reinforced, some of them can be culture -induced. I think we just have a bad story. Humans have infinite amount of bad stories. Our brain is lauded up with a firmware that is like developed for the San Gatti.

14:03So basically, everything we're doing on planet Earth, we're basically managed to awkwardly do operations against human nature. Sometimes our environment does it for us. Sometimes our self -development can help. You replace one bad story at a time. One of the bad stories is that artificial constraints are annoying. artificial constraints are help with setting up boundary conditions, while they are constraints. Like if you really know what you're doing, play some decent notes, like play with constraints. See what you can do, like try to push against what's things a little bit, and then if you discover that one of the constraints was actually not not artificial constraint, but was actually a detrimental constraint for the creative process, then we can change it because we're trying to figure out how to build the best things to camp.

14:45Do you agree the best CEOs of the best resource allocators when think about constraints. That's immediately what I think too. It's a commonly held saying, as we both know, do you agree with it? That's a great question. I think it's a heuristic by which people can explain to themselves why certain people are great CEOs, but it's not for reason. It's not causal. It's correlated. I think the best CEOs are people who have a more correct model of a world than everyone else are good communicators or have a other form to have other people follow them in such a way that you build against that model and have such a high batting average that the world that they are building against is going to come to by the time the project is done.

15:28If that happens, more than quite flip, then I think you have a company that's out competing status quo, out competing industry, out competing orthodoxy, because the ambient understanding of a world is just not that good. Again, most things we think are true or wrong, wrong in important ways. If you observe this, like visitors for miles, look at a company that is run in such a way and they will say, well, that company is like incredible at allocating its resources to the project that ended up making a difference. And there's very little waste on these kinds of things, but what's the consequences of a company?

16:00Like you asked me about subtraction earlier, like the subtraction is important because like, again, often companies end up doing things for reasons that everyone else is doing it. You know, sometimes it's much easier to add something to a company when it is to remove something from a company. And so you can only add and never remove you're gunning up the system after work. Can I ask you said about kind of most of our models of the world and maybe built on the wrong foundations. You especially today have kind of unlimited access to any view on anything in the world really. You could email anyone and get their thoughts and they will sit on a cool and explain how they view the world to you.

16:36My question is how do you build your model of the world in new areas where you want to have a model? What does Does that learning process look like for you if you're aware that many people have the wrong view of that model? By the way, I don't think this success is that differentiated. Any more, thank you. Thanks to all podcasts. I mean, this nicely do agree with that. If you think about, say, take COVID and think about how shipping and delivery changes in the world of COVID, you have the ability now to call up Ryan at FlakSport or the CEO of UPS or you name any of the big providers and say, I'm learning how this changes.

17:08Can you please explain to me the different moving parts and you will get access to knowledge that that book class wouldn't give? You're clearly right. I just I actually don't use this as much and I think there's a particular reason I grew up in an outsider city again like I come from a town which was started I think by Julia Caesar So my skills I just passed sort of developed to try to find pieces of Information to the answers to the questions I have is often white papers or books written very long ago I think those skills are 10th, like now almost ultrafine. It's just so fast to go in a search engine and look at where the people discuss these topics for the people and like all of this is the how.

17:47But there is a more important thing behind this and much harder to articulate and much more important because I think common with all the kind of people you would reference as the people to turn to when something is happening in a world and you really, really would like a perspective. One of the biggest differences in a world in plan, there is like, it's like culturally between people who are interested in what's right in the context of groups, like what are people thinking about something? Like what is fashionable, lab league or not? Or the people who you want to know what's true? And if you make a decision to prioritize finding out what's true rather than what's right in the over -tuned window of your communities, it's like you've had a lonely experience and you will have to go more to primary sources.

18:27Because again, almost everything we know about the plan of is directionally correct but wrong in some details and often correct as a surestic but true for reasons that are completely different from the explanation of our times. And so if you are really, really interested in figuring out how to make the best possible decisions, especially in the context of a company, and you really, really, really need to follow what's true, prioritize that and surround yourself with other people on similar journey. He said surround yourself with other people on similar journey. I spoke to Glenn before the show and he said on decisions, you're incredible world class.

19:01When it comes to dealing with sunk cost pharmacy, what do you think he meant by this and how do you deal with sunk cost pharmacy? A sunk costalacy is another thing. It is a real, an autocratic fallacy like the fact that you have been doing something for a while means you want to keep going because if you change your mind now, then you're basically passing judgment on all you pride decisions. So, so again, if you're on a path of wanting to be right in the context of others, logical consistency is your primary optimization target. Like you want to have made a choice about something and you want to stick with this choice because your identity is wrapped around your beliefs.

19:38You share beliefs again because you're prioritizing what other people think. You give it's maybe too strong a term, but like I can't help but think that if that's your operating models, you're actually outsourcing yourself to the people around you because you require positive information by them to know that you're doing a good job, which I find is like really regrettable because that actually gives too much power to people around you, first of all, and second, they don't want that job. They're not interested in moon lighting as your value system. But if you're in this mood view, sunquast fallacy is something that is very, very important to you and you engage with it a lot.

20:13And if you see people that seemingly have no problem with it. You will talk about them being good at not falling for a sun cross policy. But again, it's this is the language of the predominant operating system of a bird. If you're interested in truth, it doesn't exist a sun cross policy because it relevant. Like it's an import into your decision making process that you have been doing a certain thing. But you already knew this because you were doing whatever was best given your entire mental model. you're trying to avoid continuation of previous ideas. What you want is every moment of your life, you ideally want to run a function over the entire assert space of your mental model to decide what is the best possible next move for me.

20:53How should I spend the next minute? If new information comes in, that is not dangerous to your identity, this is delightful. This is what your curiosity tears you towards. And if that piece of information invalidates any of prior beliefs, you might completely change obviously you need to go do the exact opposite of what you've been doing until this point. This is not changing you might because your mind is consistent, your mind is executing a function over the search space every step of a way. It's a variable that change and that's like there's no more problem with it. But it's true. I mean, there's other sentences like with strong opinions weekly ahead.

21:28I tried I tried to be an advocate for what I think is best part of because if someone disagrees with me, I want to know this because they might be sitting on a piece of information that I'm going to add. So I need to make my current best take on everything clearly known because I want the disagreement because then I can learn something which then maybe makes me completely change my mind. And then I'm going to be strongly for that because again, I want to have people add more information to this. Again, these are consequences of this seemingly simple decision of are you interested in being right or are you looking for truth?

21:58How do you know when to stop doing something? What I mean by that is he said every new piece of information is a delight. So you engage with a strategic decision and the information is revealed. Is it strong enough to make you turn back? You don't have enough data. How do you have enough data? Well, no, when enough is enough and you've got to turn around. I call in power, I've had a good sort of surestic for that. If you have like between 40 and 70 % of information, you should probably make a choice. Before that you don't have enough and afterwards it's too little. I think that's largely right, but like I think it's missing a dimension on the reversibility cost.

22:31If a reversibility of a decision and sort of a total body of work on it is low, then you should change your mind fairly. And if a reversibility is high, you want to be very careful, like measure twice cut once. Can you take me to a decision that you made that was a strong strategic decision that then you reversed on the back of new information? Sure, I'm a very strong believer of physical proximity. So, I think physical proximity is massively underrated and underappreciated. I mean, the best team in the world, the fastest movement team in the world, is one person that has all the skills needed.

23:01The second best is a team of six people that are intellectually diverse and can bring a lot of new different information together, but like become a real team, especially if one person is being senior, because then you have a lot of what's most of this learning. Beyond that, you want to be on one floor, if not, you should be in one building. All was a baby's strong opinions. We've designed incredibly good office spaces. We actually wanted to open source, I don't think we ever did. Our floor places, because my co -founder Daniel did a amazing job in quoting everything I just said into office space that like just like everyone worked out of them, like was blown away by just how collaborative it turned with all this backdrop.

23:36Like now Shopify is like 5 ,000 people. Otherwise a million people, we can't stay in one city. It's just, it was just not possible to build the size of company we need by relocating everyone with labor for the warehouse locally. So we had to go to Montreal and Toronto and so on. So we were kind of in this sort of hybrid world already. We were also expanding to Europe. So we were violating the time zone kind of thing. This equation started rerunning. Now my conviction was also that hybrid is worse than over mode because there's more power to the team that's close and it To treat the people who are not as appendages and and and creates a lesser experience.

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24:12It's actually much more shared experience If everyone's in their own square on a zoom call. Basically two things happened. One, it became clear that Shopify needs the kind of staffing that we would not be able to support in a single place. So we were basically sleepwalking ourselves outside of our principles. And I might believe was that at a certain point it flips and it's actually better if everyone is remote. And then we were getting very close to sort of a 50 -50 point on like on on on this. I think within a year or two I would have transferred Shopify to remote entirely. And then COVID started.

24:49And in fact, I can prove this because we actually did a game day. We'd be closer office for a month at some point, just to like develop empathy with the people we're working remotely for us. Actually, that worked really well and we found some tooling problems. But that was one of our chaos monkey things, which I thought was sometimes these sort of subtraction events. That was really fun. At least I thought it was fun. So people didn't. And so we practiced and then and COVID happened and now there's one variable in my model, which is like everything we just talked about except are people allowed to leave a house and it's a Boolean and it was true.

25:23The entire world it wasn't at the implicit unstated input into the model and then lockdowns happened basically every year offices and like true became falls and now we deriving this equation with this change variable immediately yielded. Hey, let's book from remote and trajectory wise, I knew that this was probably gonna last a year, just because if you look in tech, you know what an exponential week of a week growth looks like on an area under the chart, politicians turns out, didn't. So it was kind of clear that this would be like 2020 would be a very strange year. And so we, I think, called like let's book from home, maybe amongst the first, we then also said, we're gonna stay remote and become a digital by default company.

26:02Nothing changed my mind. like proximity is still ideal way to look together. I would always recommend it to a small company size that can fit on one single floor plate in an office tower in one city. If you think about founders listening to this, say they are in one city and they are in that ability, is it not actually more difficult to do it scale to that stage together and then go oh shit we're too big now, we're gonna need to switch from all in person to all remote. Is it not easier on day one to say new company or remote. Yep, the variable you have to consider is the talent. If you assume your company is going to be 100 people and you're thinking about like high -income first 100 people, even if you don't think you can work as well together remotely, let's put a 10, maybe 20 % discount on productivity, is the talent density more than 20 % higher if you can hire everywhere than if you're restricted onto one city.

26:52Saying yes to only one city is actually says no to all other cities on that earth. Like yes, this is a way more costly than nose, which is also content to it. If you say yes to something, you actually say no to everything else. If you say no to one thing, you keep the optionality to say yes to the right thing. Again, if you can hire, let's say, even everywhere in the United States, I mean, it's the least skilled person in your engineering team, maybe twice as the least skilled team would be if you would restrict yourself to, especially like a secondary market location to build your company. But as a tourist could be either yes or no, but you should know it.

27:22because if you don't have an opinion on it, you just made a decision not adding a very important input. Sorry, you said about a 10 -20 % productivity decline, I'm too interested, because I think bluntly there's a 10 % productivity decline when you're remote. People take Friday afternoon off Monday morning, that's lower in new name -es. But then you also talked about and have done before, like reducing the number of meetings, canceling meetings, are people more or less productive in person or remote? I think people are more productive in person. There are certain things that remote work is not good at, which like this sort of free idea flow brainstorming session is not great over video.

27:58They're sort of like magic that manifests only in the middle of a table, like sort of floating over the conversation. The sort of sheer picture of everyone's trying to figure out what could be do rather than how to get there. How to get there works great remote. What is possible is not that good. I think you can proxy it also to wartime, peacetime if you like that language. Like what time anything is harder to do a remote? I think one thing that's much easier when you're in person is also encouragement and sustaining moral And I think when you have bluntly volatile markets like we do today You see you know large drops in that worth for employees And I was speaking to a friend of mine who's see of like a 30 or 40 billion dollar public company 10 billion dollar difference is probably quite a big difference So I should hey get that one right But he said the biggest problem that I have stairs every day I walk in and people's heads are down because they're looking at their stock options going We've just lost another X percent.

28:51How do you think about maintaining morale in the face of volatile markets? You said earlier about being a great communicator. I was fascinated about that when I heard him say it. Yeah, it's interesting. Yeah, it's never been my experience. I've always told the company, the stock price is not the company. We've worked on something called the Fair Market Value of Shopify, which is like there's some total of products and skill sets of a leg offer people. Most of the value of the leg offer size company is It's extraordinarily hard to value from a gap perspective, like shock visibility to a higher of the best engineers in the world.

29:22Like what is that worth? I think it's tens of billions. As a competitive advantage, not an asset on any asset sheet. Now, I've never showed it, I don't want to value it. It's like I think that it would be difficult, but it is one of the major assets we developed. Right? The ability to fair market value for companies is unguessable. The stock market is playing a daily guessing game. It's like guess the fair market value. And actually, most people don't play that game, they play the meter game of like guess what other people guess is the fair market value. And so it's a game that has nothing to do with the actual value of the business.

29:51And it's Wall Street playing Wall Street. And as you're selling shares, you have nothing to do with it. And in fact, you have much better information than with people who are doing these trades. Do you care if people like you and more people think no one doesn't care at all. But like I use it as a piece of information that I find curious. I see that's my job to be a likable person, to be someone who ought to be liked. And if someone fails to do that, that's like them not doing it right. People do not live rent free in my head in this particular way. So you mentioned being a likable person. I think, you know, I've listened to many of your interviews and I mean this respectfully to everyone, you and you.

30:27The one thing that people kind of missed was kind of you. Like, we're not your decision making, we're your learning or any of these optimization things, but like I spoke about doing my work on you beforehand, I heard about the one for marriage that you have. Toby, you have a fantastic partnership with your wife. What makes a great marriage and how do you sustain that with being the public company? I mean, I can't even go with a girlfriend and a podcast, Toby, how the fuck do you do? I met Fiona like super early in life and ended up being like so in many ways opposite people and also have such a strong bond of intellectual curiosity and maybe grew together from basically being kissy, I think we started dating about 20 years old, which was more than 20 years ago.

31:10I mean, I honestly think they often being like the CEO of a company as a team production and Fiona does not get the credit she deserves, like she encouraged me to even start a company in the beginning, so like often you can play this game of like how many variables would have to change to at least to a completely different outcome and it's like there's always exactly one litters for you and I have for me like so she's never been on a payroll of a company but she's always been someone I talked about or the challenges we've sometimes divided in conquered by reading like there's like 15 books to read because we as a unit need to understand this thing better okay let's go have these actually she reads faster and I do so she usually gets to a stack faster but what sustains a great marriage it is to have common project but different lives a bit as well like she is interested in other things than I and and and she's enthusiastic about what she discovers and brings us things back.

31:58We are just like deeply curious about each other and I think that's been sustaining. I don't think I've cracked the cord. I just got extremely lucky. Glenn said you were probably one of the most like computer native technical people. He said if Toby could be an IP address, he would be. I know. It was quite a good description. Do you struggle to turn off? Like, do you go home and you're thinking about the business? You're thinking about acts, you're thinking about why? And actually, being in the moment, being with your kids, your wife, is that hard? I'm yeah, I'm never off like I doesn't but it's also never tried to be off I will always run background processes.

32:30I have the kind of brain that just like lends itself to doing with kind of thing I think real life balance is basically nonsense. I think it's like I mean I work life harmony is kind of a better term Shopify is unbelievably interesting. It's a perfect vehicle for someone who's gonna on a Live mission like me and lots of my friends here It provides the consistent and impetus to like no what new technologies can do. Because man, these are the most interesting times in human history, I think. Why do you think this is one of the most interesting times? We have like de -globalization like never before, income inequality like never before, while South gas systems like never before, climate change like never before.

33:04I'm looking at the world quite scared if I'm totally honest, Toby. Yeah, but I think this is for overlay narrative of a media. Again, if you go out there from truth, I'm quite concerned about climate change, but I'm also 100 % like, you know, it's a technology problem. Well, if in quality it's like this is the most wealthy societies ever been. Like no one until they recently had ever had a warm shower. Like it's like it's like unbelievable luxuries, be it be it be it have you just be it just have a built in hedonistic dreadnull which makes us forget about it all. If you don't have to check my word for it, you go for something like Stephen Pinker's book Path to Renlightment and it just drops every single start you've seen quoted as going worse and shows you it actually gets better.

33:42I'm extremely optimistic. There is a effect in the world which kind of sucks, but it's going to be temporary. And it's I'm doing fine, but everyone else is fucked, effect. And it's actually being measured in all societies. And it's like 80 to 90 % of people would say, I'm doing fine. But everyone else is doing really, really poorly or like around me. So 90 % of people say it's fine. And they think a vast majority of people are not. And everyone thinks this because I mean, there's real problems in the world. and worth inequality is a thing that could be even better. But it's also like a bad faith take that worth inequality is a bad thing by itself.

34:17Like, the... Do you do the... I'm sorry, I'm, I don't, I don't agree. Like, I think people vote for Trump. I think people vote for Brexit because it's not that they're doing OK and everyone else isn't. It's because they're pissed off with what's happening. And they're not OK. And I think if you go to the 98 % or, that's probably a gross exaggeration, but 90 % of people in the UK, I don't know, 85 in the US or 90 % in the US, who are actually living in real, not great quality standards and worse these standards, they're not happy with how they are and they don't think they're even okay. Yeah, no, it's true.

34:48People want things to change and there are real problems in reward and people want to see things improve. People vote for, are they think things can be approved? We have disagreements, but even the largest disagreements like Brexit Trump, yes, there are disagreements, but they are very minor. Like, everyone agrees that like, hey, voting is a good thing. Everyone votes, things voting is presumably a good thing. The system of democracy with behalf and enlightened self -interest harnessed towards the greater good, at least those components of capitalism are important, and have demonstrably been superior to everything else we've attempted before.

35:22People probably do agree that completely unconstrained pursuit of a wealth has negative externalities and would like some changes. If you look at the poll data of what people want, they actually want to get to largely the same goals, no matter which party they are at. They disagree on the approach there, but even they are they don't actually disagree as much. The political spectrum of positions you could hold is massive. It goes all the way from complete analogue and communism, all the way to fascism and the space is massive. We are arguing in a bracket which is around here. Now, the people who are on one side of it think that people on other side are versed, but the spectrum could be so much larger here and it's for old like I against my brother, my brother and I against my cousin my brother and my cousin against everyone else thinking people are somewhat tribal We are infighting because we do not have external attacks like it's it's not people are not really coming and saying hey Let's go absolutely straight up to like Stalinist communism tomorrow if they vote All the political parties that we are voting for and this is a credible threat coming from outside would start figuring out how much they actually agree with each other Anyway, but do I know I built a company?

36:30You said about the head of the stick treadmill that humans face and are always on and that continue to search for happiness. Honestly, I face this too. If you told me you know I'd be here chatting to you years ago when I started from my virgin month, I think it was a joke. But I'm still not. I still want more. I want it bigger. I want to have more. It's never enough. When you think about that, treadmill and looking for awesome, the bigger vote. Are you happy now? I think happiness is a temporary thing, but it's a terrible goal. It's a goal that's sold to people to keep them miserable. But you want contentment, which is very different.

37:03You want to be content, that's a worthy goal. If people would start making this differentiation, but we will figure out it's like vastly more people currently live in a state of contentment at many other playtime in history. Now the thing that can mess with contentment is, again, we are comparators. No one wants to be the worst house on the street. The street became the entire world because of social media. This is by the way one of the biggest effects of the American Civil War was urbanization because soldiers which were predominantly rural lived on farms had to pass through the cities Before that people just didn't travel more than like 50 kilometers away Or even less 20 kilometers for usual range of travel throughout your lifetime after people pass through cities They're like holy crap.

37:43It's so much better here So people started moving to cities just because like you compare against what you know as possible So we derive sometimes content and from that over that's a bug anyway So happiness is bad because happy is temporary like I'm happy then I'm like just like seeing a friend that I haven't seen in a long time, but afterwards I'm like content being able to like have fantastic conversations with my friend whenever I see him. So that's an important one. The hedonistic treadmill is the engine of Humati. It's a thing that drives us to do everything that we actually value. It's the thing that causes us to strive, things to be discontent, start with core, thing that pioneers set out for new shores.

38:20It's the thing that sets out. It's the thing we want and as so often in life, the best thing about us is also the worst thing about us. It's a very, very bad idea to make it your primary objective or derive how you think about your current state from it. I can tell you look, I've been extraordinary lucky in so many different ways, amongst most, materially. It turns out like I would have done this no matter what, but like turns out software products turned into companies can lead to more wave generation than almost every other pursuit of that of outside of maybe real estate. I've talked in this for reasons of my own on a journey and accidentally talked in massive, massive material wave generation in this of which of various more percent of a wave that shopper created came back to me which is still a very large number.

39:06What does that do? I mean it's cool. That's probably the best description. One thing it allows me to do is like just sort of be surrounded by beauty. So best term, I get to you know, I live in a house I was carefully designed by someone who was the best building that they could build. The things around me, like close aware, are made by entrepreneurs actually my entire water comes from Shopify and they made a decision that something else needed to exist and was a great, great product. What does all that do? I would say it makes my days probably between 2 and 5 percent better. That's it. Past a certain point, which most people clear, the average household income in Africa is $60 ,000 a year.

39:45Most people clear this bar. Past that point, you can get the kind of things that inspire you and around you, and you increase the quality of happiness in the day or it will lead to the light you encounter, the objects or maybe the conveniences. By a couple of percentage points, is that worth it? Hell yes. Huge. Like, 5%. That's a huge lift on the baseline number. But like, the baseline number is like, did I have an interesting conversation with friends? Did I have, did I build something today? Did I, is everyone healthy around me? Both are massively bigger inputs. What lot of shrew makes you happy?

40:20It sounds like for me it's um, Uber Luxes don't laugh, but like getting a really nice car, it just makes me happier, more relaxed. And that's like the one thing that I would spend on and it changes my mood. Yeah, one of the things that makes me happy, I just like love really, really, really quick keyboard. I know it's not stupid, but like I'm typing a lot. You want to see the biggest things like a great share, a great keyboard, a great monitor, a great mattress. Like those things are incredible and the cook -o -shanel set is perfectly. Oh, but actually, Mom's makes for opposite point, but it's still funny, so I'm going to share it.

40:50And because I set it up, the best things in life are free, but second best things are extremely expensive. I know that well, my mother's from eco -visionals biggest fans, so I think that's a great one. Toby, I love this. I'd love to do a quick fire round with you, so I should short -state when you give me your immediate thoughts. Let's start with you said, the best and the worst parts of you. What is simultaneously the best and the worst part of Toby? That I may hold a different opinion just because through other conversations I've found that I've was incorrect previously and it is a harrowing experience to people sometimes.

41:21There's a societal premium on consistency of choices that I find is useless and if you think from first principles and that is definitely a trip sometimes for people. I think the vast guess, what's your biggest regret? I don't think I have any macro -recrets. I have millions of micro -recrets. There's a million things we could have done better. Decisions I made where the input that could have told me this was not the right thing was available easily, like with an email or with like a dashboard or something. It's even I probably already had it and I just kind of wanted this to be true. Right, like that.

41:56I regret not being more troupe -seeking there. Is there a strategic decision you may reshopeify that you wish you could reverse? us. Yeah, I mean, for a bit, I started believing some of us, for sorts, which people like to believe about leadership, like that my commitment is bad, like that is the dumbest idea of pletive. There's probably no singular idea that has destroyed more business value on pletive than the idea that my commitment is a bad thing. You're like, I don't agree with that. That sounds crazy. We call micro manage. How do you determine what you might manage? If you might manage, you're going to create distance within the org because people are like, why is he managing them and not me?

42:31and then you were also going to grow people who were like, hey, he shouldn't manage me and fuck off. And also, you might not be as good as the people that you hire in those roles. You also don't have as much data in those roles as those people. Hey, you should work on the machine, not in it. Like, hire the best and allow them to do that. You're correct in one frame of preference where the interventions are bad. Let me give you another example. I say you're a leader of a team, like we're driving a car. You've just been around there and you know, like in a straight line, they're going, there's a cliff.

42:58But you're not micromanaged the steering wheel at like because that's literally what the situation almost every leader said, right now people are terrified and she is a leader you have to understand the decisions and mistakes that people have to make to learn versus those that they cannot make to learn. That's true in the high reverse politic case not true in the everyone's fatally crushing case. Oh yeah, no if everyone's fatally the other new obviously have to intervene, but the majority of things are not reversible very very few things are irreversible. The thing you're describing is like, is this sort of a deal that asks you or for leader.

43:31Right? Like where like pointy head boss comes and changes like most of the cheese around. That is not micromanagement. That is just being extremely bad as being a leader. What you actually want is you want your entire company to compose into something that is something like an idea lab where people were closest and for people who are like the biggest perspective come together to make for the best choices. For that best of all, for absolutely everyone in black inverse. And you know, in most cases, what you do is you find someone like you find to see if always amazing. You work with them together.

44:01You make decisions initially for onboarding. You learn to trust them in such a way that you can now delegate the responsibility and and and and the book. Presumably for a bit, you should trust but verify it because again, you are like trying to like you actively have to build trust with people. Trusting by fear, trusting by name of a roller is not a great idea. You can use someone's background as like a massive pre -charge on a trust battery but you should come to your own opinion. Like no leader can ever abdicate responsibility, you can only share it. It's never broken and it's never, you always still have it for everything.

44:34But you can share your responsibility for all parts of a company with your leaders and other people. Do you know what I think you have to abdicate responsibility, but share accountability? And that's what sucks about leadership. You didn't do it, but when it goes right or wrong. In good and bad, it's often on you. No, you can't be like, it is impossible. You can share responsibility, but you never not end up being responsible for it. Like, yeah, I'm responsible for everything that ever goes wrong in the company. At some point, maybe because I hired someone, but I also hold the responsibility, therefore, for all outcomes.

45:05But you've found that lead companies are also like a little bit of a different beast, because there are tricks by which you can diffuse responsibility and reject. I mean, the entire vote of consulting is basically one large way of outsourcing a responsibility for bad choices. That's a mean product bad selling. People might disagree with that too, but like, that would be a fun different conversation for another day. But I don't think you should do that. Like, I think you should stay responsible for everyone. You should bring what you uniquely can bring to all, like, conversations where it's of value.

45:31And you should be very, very clear that you're looking for the best, rather than being right. Again, which is also not my management. This is actually just, I call it my quad leadership. It's like having editing the final thing. A great company is, looks, our great products, look to the users, like they are a book written by a single author. They are logically consistent. They are pretty in the same tone of voice. If you learn a pattern somewhere, it's first of all approachable at this point, but then it's also ripped like the same pattern teaches you about other parts of the system, especially for the big system.

46:04Doing this a thousand, thousands of people require a lot of coordination. It's a huge coordination challenge. And it requires people to learn how to like, by watch principles to to make these tasks. Now, you're going to do a million things that have like, for instance, like just like, if something I Shopify, show there's absolutely massive piece of software, probably one of the biggest pieces of software planned of. But we also have things like design systems, which we also share with our ecosystems. And this design system is like just helps everyone fall into some big pit of success because a lot of knowledge of how to build a great user experience and user interface is actually encoded in the design system and therefore is a creative constraint if you will.

46:40The floor quality of execution for everyone who just use the design system is very high, but floor is high, however the ceiling is uncapped, which is the mark of a brilliant system. That's the most important thing you can create, but the process of creating Polaris with the design system is something when I was involved with because it has to conform to the aesthetics and my as a founder ideas about what approachable software looks like. That doesn't mean I did or the work -noded project, but I hold some core authorship over the creation. Someone would call that potentially micromet and say, hey, Toby wants to be part of the design review for the drop -down component and these kind of things.

47:17But now it's just like just deep appreciation for the craft, it's caring and that's perspective that's honed over 19 years of doing this kind of thing. By the way, this is the worst lighting rod anyone's ever had by way at this point. They have a photo, you gave me this to it. But the options you have are infinite. You have an infinite amount of options to become a micromanager on. You said about the drop down there. As he said, it's the most complex piece of software almost on planet Earth. You could choose to be a micromanager across those 30 ,000 questions. And so you're gonna overload yourself and it's not gonna be functional leadership.

47:52You have to at some point not be a micromanager. You have to be able to trust people. you have to work with like I do not need to look at drop -downs anymore because I've worked with the Polaris team and trust the leadership and trust the principles and therefore the sharing responsibility for Polaris but like I'm extremely confident without looking at all the work. However, if it is like hey let's make a new version of Polaris, they know that hey like that least tell Toby so he can update his model of what things are going to look like in a year or two by when we are done with this or a couple months.

48:23And so the company understands that information has to flow and that we work together as a team. And this might outrate you, every great product on planet Earth has been made like this. There's no other option. It is always a collaborative effort of a lot of people where we have a common thing is that there's a common culture, a common belief system, a common set of aesthetics and things, but also work together, offer a lot of people from different layers with no regard for post -world vote to concepts like org charts and so on, which are like even the military doesn't use org chart. I like like like chain of commands.

48:56In fact, they they usually invu it like for people on the people who are on deployment, like everyone works for them. And I think the best companies resemble that kind of approach a little bit better. Like shopping company made made by a crafter and by founders of crafters, craft people again, a literally apprentice in my craft for craft people. And we support the people who are building, but we support them by helping them also know the terrain, know where to go, have a baggage train show up at time and solve the larger coordination challenges and have everyone do some of the best work of their careers and their lives together.

49:31And this is what it looks like. And you know, you bet this is how for Disney designed the parks. This is how Steve and Johnny engaged with Apple. And this is, again, this is true for everything that isn't a pure play product of the orthodox ambient thought off its times. Penultimate one I promise because I should have we totally wrote it but when you think about leaders that embody this for you, who do you most look up to? Is it Steve and Johnny? No, um, so the bow, I, um, who, who, body, because I think boy Disney is, I think someone that is understudied in, in technology. I think you want to learn as much as you can from as many people as you can and you should study, study all of them, pick your bits from them.

50:14I, I, I've never found the one person to model myself on or one person who has kind of had it all figured out, this is a fun part. There's huge amount of alpha and doing better than everyone's done before. In fact, it's not even that hard. We are not that good at building companies. We're not that good at building projects. We're not that good at making teams. We're not like that. That is like maybe a three out of ten. We're going to know how to do this way better in like a hundred years from now. So just like try to be a four out of ten, and you're like beat everyone. You know, all these other amazing founders through time, Elon, on a sock, the contemporaries and the great founder of that company that we finally get to build, they are probably before sort of 10.

50:53But like, Facebook is limit. Like if someone has a perfectly insight for you, you could build the probably 8 or 10 right now. It could be one company which is vastly superior to literally everything else, just better firmware, better model of a world, better set of beliefs, maybe better technological systems, who knows, you're going to figure it out. We're going to figure out basically everything in the next 100 years as my belief. So at the end of our careers, likely, we can actually say done saying, hey, what's the stuff we didn't get now in the 2020s that later on we've discovered? And I can tell you, you're going to be embarrassed by our lack of its stuff we already, like someone's already done, and probably brought about in some obscure book or some Harvard Business Report, probably not.

51:33Maybe they don't write on interesting stuff, they're just sort of like, right, fortune cookies usually. Or actually more importantly, It's the way the jazz band works or it's the way video game communities organize themselves I believe you can learn more Is a statement for you. I think you can learn more by studying word -of -warcraft rating GILTS when you can learn from studying companies about coordination and and what great looks like There's infinite amount of things to study nothing should be a black box and there's like and everything's more interesting when you thought. And so that's fun.

52:05It's just so fun. It's fun to have a task. Like, do you have this thing really be like, there's millions of entrepreneurs probably made tens of millions more if you want to reach for independence. And the best way they do this is they know whether is it like some kind of product needed and know how to make it and maybe can have a little bit of that. And then we take care of like just a lot of the drudgery of like taking in the world of like like global commerce and internet selling and so on and not only that. You're also like pulling value out of the latest things that are possible. Like this is the greatest part of the job.

52:37Brad, like what other things that are just about becoming possible right this moment? And what is the angle they should take for false things to give it to millions of services? Like maybe one, some of these things are extremely valuable and they might have it before the big box stores that we might be competing with. How cool is that? like since Ben is a leverage and balance tilted in favor for small that's good because small is more nimble and so it's cool to protect and again some of the most interesting times on in human history and have a task with all the change around us for technology all the stuff that's that's happening we get to say okay well does that matter for people who are reaching for independence if so how can we tool it up and now we get to play with it and and that's like now we get to have another Another one of us idea -labs, ideally done in proximity, where we can figure out what is a vigny to build and then we build it.

53:28And that's awesome. I love that. It's the best loop in wood. Toby, with absolutely nail, the quick fire round. I think he top marks both of us. Also the best sound by On the World of Warcraft. Honestly, I've so loved this. His reasons and shows like this, why I love doing this so much. Thank you so much for being such an amazing guest, Toby, and I so appreciate it. Oh, awesome. You know, thanks for doing this. You're doing a fantastic job with this podcast. I love it. And this show I love what you're developing here.

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56:31As always I so appreciate all your support and we have an incredible the Mamo episode coming to you on Wednesday where we profile an incredible company that scaled to $600 million in revenue with absolutely no venture funding. Yes, we have Mike at Butcherbox on the show on Wednesday.

From the publisher

Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business. Over an incredible 18 years, Tobi has scaled Shopify to 10% of total US e-commerce, millions of merchants in over 170 countries, and a market cap today of over $60BN. Huge thanks to Harley Finkelstein for making this happen.

In Today's Episode with Tobi Lütke We Discuss:

1. From a Small German Town to One of the World's Most Powerful CEOs:

  • What did Tobi want to be when he was growing up?
  • Who did Tobi learn most from in his younger years? How does Tobi think about the importance of mentorship in learning?
  • What does Tobi know now that he wishes he had known when he started Shopify?

2. You Can Learn More from World of Warcraft Than You Can Companies:

  • Why does Tobi believe you can learn more from World of Warcraft than you can from studying companies?
  • Why does Tobi believe that humans are terrible at company building? What are the most obvious ways we can improve the quality of the companies we build?
  • Why does Tobi believe that in-person is far superior to remote working? What are the nuances?

3. The Best Companies Operate with Many Constraints:

  • Why does Tobi believe in all cases, constraints produce creativity?
  • What is the difference between an enforced constraint and an artificial constraint?
  • How can leaders create and enforce artificial constraints when they are not real?
  • How do the best leaders use constraints to ensure their companies move faster and faster?

4. Inside the Mind of Tobi Lütke: Decision-Making & Prioritisation:

  • How does Tobi reflect on his own decision-making process? How has it changed?
  • Why does Tobi believe that sunk cost fallacy is BS and only leads to your outsourcing approval to someone else?
  • Why does Tobi hate "black boxes"? How does he remove them from the org entirely?
  • How does Tobi decide what to learn? What is his learning process once he has made this decision?
  • How does Tobi decide what to prioritise in terms of strategic initiatives for Shopify?

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