Cold open
I think you can learn more by studying World of Warcraft raiding guilds than you can learn from studying companies about coordination and and what great looks like. There’s probably no singular idea that has destroyed more business value on Planet Earth than, the idea that micromanagement is a bad thing.
This is 20 VC
Intro
with me, Stebbings, and this show is the definition of persistence. I have to say, I sent my first email to Tobi asking him to come on the show on the 05/17/2020. 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. And so with that, I’m thrilled to welcome Tobi Luttke, co founder and CEO of Shopify, the global leader allowing anyone to start and grow their ecommerce business.
Over an incredible eighteen years, Tobi has scaled Shopify to 10% of total US ecommerce, millions of merchants in over a 170 countries, and a market cap today of over $60,000,000,000. But before we dive into the show today,
· Sponsor read0 min · 417 words
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 two, ISO 2,701, HIPAA, GDPR, and others. Secure Frame’s industry leading compliance automation platform paired with their in house compliance experts and former auditors helps you get audit ready in weeks, not months, so you can close more deals faster. Secure Frame makes it fast and easy to achieve and maintain compliance, so you can focus on serving your customers and growing revenues.
Automate your security and privacy compliance with Secure Frame. Schedule a demo today at secureframe.com. So if compliance is one thing you always have to prioritize, you also always have to prioritize your team and work. Well, it’s truly global today. And until now, there’s been no HR platform that’s been able to handle everything for everyone, no matter where they are in the world. Well, Deal does exactly that. It handles all things for global teams. It allows you to easily consolidate contractors, EOR employees, and local workers in one platform with a tool built to evolve with every stage of your company’s growth no matter who, how or where you want to hire.
So whether you want to compliantly work with a contractor or a project in Argentina, hire an employee where you don’t have an entity, or run payroll for a direct employee overseas, you can do just that and so much more with Deal. It’s way less HR admin and a whole lot more peace of mind. Simplify global team management, payments, and HR so you can hire faster, streamer in more processes, and stay compliant always. To see how Deal can scale with your team, visit deal.com/20vc. And finally, are you building enough conviction to outpace other investors in this changing ecosystem?
Tigus helps VCs get under the hood of their investments quicker, map evolving markets with deeper research, monitor the financial health of portfolio companies, and crucially source new deals. Tigus is trusted by top firms like Redpoint and Spark Capital for everything from expert calls and transcripts to quickly surfacing insights across filings, comms, and benchmarking. So find out why a majority of top venture funds are using Tigus on a daily basis to differentiate, consolidate, and accelerate their research. Head over to tigus.com/growth for your free trial. Three, two, one, zero.
You have now arrived at your destination.
Conversation
Tobi, I’m so excited for this. I had so many great things from Glenn, from Luke, from Jeremy at Bessemer, 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. I thought we’d start with something a little bit off the bat, to be honest, Tobi. And so I thought we’d start with, think back to when you were a child. What did you wanna be when you grew up?
Hey. So I got lucky. I got really, really, really lucky. My parents got got computer. I was six years old, and I knew that there was like nothing else, like, that would be more interesting. But I learned programming before I knew that was a thing or a term. I must have been, like, 12 years old or so that, you know, there’s just no chance I’m gonna do anything other than program all day.
Can I ask what captivated you so much? You mentioned six when you got your first computer. What was it about it that made you so interested?
Oh, man. You know, first time sitting in front of it and just typing any letter and seeing it appear 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 I I think people need frontiers. I think entrepreneurs need frontiers. Like, there’s a need for reaching for something that could lead to, you know, value in the world around us. It was never a question in my mind. As like there’s basically like spending time on a computer was 10 x to a 100 x more interesting than literally anything else that could possibly happen in my life for the first ten, fifteen years of my life.
You mentioned not growing up in the valley and being, you know, in the German school system and hating black boxes. I always think we’re we’re kind of all functions of our history. It’s be I’m secretly an armchair psychologist who actually never got a psychology degree or any degree at all actually, Tobi. But my my question is just, what do you think you’re running from when you reflect on that all being a functions of our history?
Boredom is something I like to avoid, ignorance. It’s more magnetic for me, honestly. Like, there’s more magnetism in the direction of where I’m going than there is a reverse polarity in the place I’m coming from. I just have a strong sense that the the the goal in life is try to become the best version of yourself. I know it sounds like super fortune cookie, but like as if at the end of life you meet the person you could have become. The the work of life is really try to minimize the diff between that person and the one that actually showed up.
Not understanding a thing feels almost amoral to me. We’ve got these incredible brains. These brains run a model of planet earth which we then constantly interrogate. I want that model to be right. Therefore, every single thing, every single time I 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 walk around with. I I go into every one of my meetings with. I go into every I encounter every situation I hold up to every problem that I need to solve.
And 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. And I wanna be able to reason about the new things that exist in the world. I need to not treat transformer models as a black box. Like, I need to understand those because otherwise 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 convenient next task, but what’s the very best thing we could be doing.
What is the new thing that all of this unlocks? And that’s been driving me every step of the way.
I mean, you just gave me so much there. I I would love to break it down into kind of three steps, though, which is like selection of learning, process of learning, and then decision making post learning. If 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. I am interested in literally everything that can add 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 that’s a curiosity itself ends up 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 Courtney, obviously, I create content. When you’re debating on a new content strategy, the 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?
Well, time is your find resources, attention you find find resources, so you you have to create, like, an evaluation function that you run over your your ideas. Right? Like, I think effort is a big factor. Also, reversibility is a big factor. Like, if something is easy to reverse and not a lot of effort, to to try give it a go because the fact that you think the value is ambiguous is a hole in your model of a playdough. Right? So filling that hole means that you’d like afterwards can avoid similar paths because you will encounter the same idea over and over again.
When developing a piece of content, you could make a decision to commit yourself to a, deep research subject about, you know, like having many many meetings, many conversations, maybe reading some books. Or you could say, well, I’m trying to trying this new channel and maybe I’m going to reuse some some content or maybe it would work in this channel or something I can do in an afternoon and then you time box it. Then 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 kind of the scorecard there. You know, 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 the right question. I’m more of a craft person than a scientist. Real artisanship, 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 ivory tower some some new knowledge, then I think you don’t actually add a lot in the world, you consume. I like building. I like I like creating. Going on a journey to gain some knowledge, figuring out something new, but then turning it immediately into something that other people that you can share with other people is the key.
If this hypothesis is right, then I get to do a thing that then many many more people can appreciate. If you if you can’t do the the the end of a sentence, I would downgrade it quite a bit to take another side of this. At some point, I was like, I need hobbies again. So pick up, like, learning an instrument, guitar, and, like, I I played a band poorly. You know, that sound seemed entirely intrinsically motivated for my own purposes, but I actually learned a lot about how to form great teams from the way a band works.
You know, how to like, I learned a lot about creativity, like improvisation, like, over a key.
What did you learn about building great teams from being in a band and learning music again?
I I learned a lot of lessons about leadership because, like, most pronounced in jazz, there’s a basic contract. Like, artists, real artists will always talk about the tyranny of a blank canvas. Right? Like, this is actually not what leads to creativity. Creativity always comes from constraints. I’ve been in many meeting meetings where people say, I wish you could do this thing where it and it’d be completely unconstrained by like, I don’t know, budgetary or time. I’m like, yeah, but that’s hallucination. That’s not craftsmanship. That’s not that’s not engineering.
I think the older crafts have this totally figured out. Like in in in blues, you would set set a meter, like you would set a tempo, 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 you’re creating a new piece of music with every note. It’s deeply creative, but the creativity comes out of the constraints that were 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 you can do a key check. You 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 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 other’s aptitudes and skills.
Right? Like, it’s a different piece of music depending on who shows up to your band. Can I ask
you about constraints in this way? Is it purely financial constraints? Or are there other types of constraints? No. I if you
take let’s take an engineering project. Time is the best is is one of the best time boxing. Like in Shopify, every project goes to multiple phases. There’s prototype phase. There’s, like there’s a proposal phase before that. The proposal is accepted. You go to prototype phase, build, and then releasing. The prototype phase is ideally time constraint and people constraint. You you you can only do it with three people. You’ve got maximum of it’s six weeks. It should actually be less, like it’s it’s sort of meanded 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 pair programming and we set ourselves constraints like every single day we have to throw away all source code other than the unit tests. And we would ship the feature the day we could implement the entire feature in that day. You really, really, really, really get code 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.
What’s a creative constraint and how does that differ from a non creative constraint?
I think all that it’s this is just a mindset. This is how you react to constraints. I think I think every constraint is a 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 for, time restraints on engineers, it’s because you can’t afford any more engineers. You have no money to hire someone. Bluntly, you’re not running out of money. You don’t have necessary restraints where you can’t hire an incremental 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 that Shopify has, which manages the phases of these projects and is sort of a central road map, 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 loaded up with a firmware that is like developed for the Sanguinity. Right? Like, so, like, basically, like, everything we’re doing on Planet Earth, we basically manage to, like, 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 help with setting up boundary conditions while they are constraints. Like, if you really know what you’re doing, play some dissonant notes, like, play with constraints, see what you can do, like like, try to push against those things a little bit. And then if you discover that one of the constraints was actually not an artificial constraint, but was actually a detrimental constraint for the creative process, then we can we we can change it because we’re trying to figure out how to build the best things we can.
Do you agree the best CEO is the best resource allocators? When you 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 the 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 lot of trust or are hugely enabled in some 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 gonna come true by the time the projects are done.
If that happens, more than coin flip, then, I think you have a company that’s out competing status quo, out competing industry, competing orthodoxy because that ambient understanding of a world is just not that good. Again, most things we think are true are wrong, wrong in important ways. And if you observe this, like like visitors from Mars look at a company that is, run-in such a way, and they will say, wow, that company is, like, incredible at allocating its resources to, the project that ended up making a difference.
And there’s very little, little waste and all these kind of things, but also consequences of a company. Like, 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 than it is to remove something from a company. And so, if you can only add, never remove, you’re gumming up the system after a while.
Can I ask, you said about kind of most of our models of the world are 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 call and explain how they view the world to you. My question is, how do you build your model of the world in new areas where you want to have a model? What 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 that this excess is that differentiated anymore. Thank you. Thanks to podcasts.
I I I mean, this I see. Do you 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 Brian at flat export or the CEO of UPS or you name any of the big providers and say, I’m learning how this changes. Can you please explain to me the different moving parts? And you would get access to knowledge that that podcast wouldn’t give.
You’re clearly right. I just I I actually don’t use this as much, and I think there’s 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 Julius Caesar. So my my skills has 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 tend like now almost atrophying.
It’s just so fast to go in a search engine and and look at where the the people discuss these topics, what are the people and like all of this is the how, but 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 the world and you really, really would like a perspective.
One of the biggest differences in a way in planet Earth is like, self 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 leak or not, or the people who are you wanna know what’s true. And if you make a decision to prioritize finding out what’s true rather than what’s right in the overturned window of your communities, it’s actually a lonely experience and you will have to go more to primary sources.
Because again, almost everything we know about Planet Earth is directionally correct but wrong in some details. And often correct as a heuristic, 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 and surround yourself with other people on a similar journey.
You said surround yourself with other people on a similar journey. I spoke to Glenn before the show, and he said on decisions, you’re incredible, world class. When it comes to dealing with sunk cost fallacy, what do you think he meant by this? And how do you deal with sunk cost fallacy?
A sunk cost fallacy is another thing. It is a real logical 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 your prior 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 wanna stick with this choice because your identity is wrapped around your beliefs, your your your shared 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 affirmation 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 their job. They’re not interested in time moonlighting as your value system. But if you’re in this mood view, sunk cost fallacy is something that is very, important to you and and you engage with it a lot.
And if you see people that seemingly have no problem with it, you will talk about them being good at not falling for a sunk cost policy. But again, it’s it’s this is the language of the predominant operating system of of of a world. If you’re if you’re interested in truth, it doesn’t exist as sunk cost policy because irrelevant. 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 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 search space of your mental model to decide what is the best possible next move for me. How how 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 steers 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 your mind because your mind is consistent. Your mind is executing a function over the search space every step of the way. It’s the variables 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 held. I tried I tried to be an advocate for what I think is best partly because if someone disagrees with me, I wanna know this because they might be sitting on a piece of information that I’m gonna 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 gonna be strongly for that because again, I want to have people add more information, to this. Again, these these are consequences of this seemingly simple decision of are you interested in being right or are you looking for truth?
How do you know when to stop doing something? What I mean by that is he said every new piece of information is a delight. Say you engage with a strategic decision and and the information is revealed, is it strong enough to make you turn back? Do you don’t have enough data? How do you have enough data or know when enough is enough and you’ve got to turn around?
Colin Powell had a good sort of heuristic for that. If you have, like, between 4070% of that 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 I think it’s missing a dimension on reversibility cost. If a reversibility of a decision and sort of a total body of work on it is low, then you should change your mind very early. And if a reversibility is high, you wanna be very careful, like measure twice, cut once.
Can you take me to a decision that you made that was a strong strategic decision, but then you reversed on the back of new information?
Sure. I’m a very strong believer of of of physical proximity. So I think physical proximity is massively underrated and underappreciated. I mean, the best team in the world, the fastest moving team in the world is one person that has all the skills needed. The 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 very senior because then you have a lot of osmosis learning.
Beyond that, you want to be on one floor. If not, you should be in one building. All those are very, 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 cofounder Daniel did an amazing job encoding everything I just said into office space that, like, just, like, everyone who worked out of it, like, was blown away by just how collaborative it turned. With all this backdrop, like, now Shopify is, 5,000 people.
Ottawa is a million people. We can’t stay in one city. It’s just it it was just not possible to, build the size of company we need by by relocating everyone with the labor pool that was 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 all remote because there’s more power to the team that’s close and it may it treats the people who are not as appendages and and and and creates a lesser experience.
It’s actually much more shared experience if everyone’s in their own square on a Zoom call. Basically, two things happened. One, it it became clear that Shopify needs the kind of staffing that we would not be able to support in in a single place. So we were basically sleepwalking ourselves outside of out out of our principles. And I my belief 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 fifty fifty point on 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. And and in fact, I I can prove this because we actually did a game days. We we we closed our office for a month at some point just to, like, develop empathy with the people who are working remotely for us. Actually, that worked really well, and we found some tooling problems. And, but that was one of those chaos monkey things that shocked by those sometimes, these sort of subtraction events.
That was really fun. At least I thought it was fun. Some people did it. 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 the entire world. It was an implicit, unstated input into the model. And then lockdowns happened basically everywhere where we had offices and, like, true became false, and now we’re deriving this equation with this change variable immediately yielded, hey.
Let’s work from remote. And trajectory wise, I knew that this was probably gonna last a year just because if you work in tech, you know what an exponential week over week growth looks like on as area under the chart. Politicians turns out didn’t. So so it was kind of clear like, clear that this would be like, 2020 would be a very strange year. And so we, I think, called, like, let’s work from home maybe amongst the first. We then also said we’re gonna stay remote and become a digital by default company.
Nothing changed my mind. Like, proximity is still ideal way to work 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 all 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, all remote?
Yep. The variable you have to consider the talent. If you assume your company is going to be a 100 people and you think about, like, hiring the 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 on productivity, is the talent density more than 20% higher if you can hire everywhere than if you’re restricted onto one city. Saying yes to only one city is actually says no to all other cities on that earth.
Like yeses are way more costly than noes, which is also counterintuitive. Again, if you say yes to something, you actually say no to everything else. If you say no to one thing, you are keep the optionality to say yes to the right thing. Again, if you if you can hire, let’s say, even everywhere in The United States, I mean, is the least skilled person in your engineering team maybe twice as as the least skilled team would be if you would restrict yourself to especially like secondary market location to build your company.
The answer to this could be either yes or no, but you should know it. Because if you don’t have an opinion on it, you just make a decision not adding a very important input.
You you sorry. You said about a 10 to 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, they’re slower, and you name it. But then you also talked about and have done before, like reducing the number of meetings, cancelling 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. There’s sort of like magic that manifests only in the middle of a table like sort of floating over the conversation. There’s some shared picture of and everyone’s trying to figure out what could we do rather than how to get there. How to get there looks 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, wartime, anything is harder to do remote.
I think one thing that’s much easier when you’re in person is also encouragement and sustaining morale. And I think when you have bloody volatile markets like we do today, you see, you know, large drops in net worth for employees. And I was speaking to a friend of mine who’s CEO of like a 30 or $40,000,000,000 public company. $10,000,000,000 difference is probably quite a big difference, so I should get that one right. But he said the biggest problem that I have today is every day I walk in, and people’s heads are down because they’re looking at their stock options going, oh, we’ve just lost another x percent.
How do you think about maintaining morale in the face of volatile markets? He said earlier about being a great communicator. I was fascinated about that when I heard him say it.
It’s interesting. Yeah. It’s never been my experience. I’ve always told the company the stock price is not the company. We we we all work on something called the fair market value of Shopify, which is like the sum total of products and and skill sets of a lack of a people. Most of the value of his like, of a SaaS company is extraordinarily hard to value from a GAAP perspective, like Shopify’s ability to hire the best engineers in the world. Like, what is that worth? I think it’s tens of billions That’s a competitive advantage, not an asset on any asset sheet.
Now I’ve never showed it. I don’t wanna value it. It’s like, think that would be difficult, but it is one of the major assets we developed. Right? So we we are building the fair market value of companies on guesstable. 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 meta game of like, guess what other people guess is the fair market value. And so it’s it’s a game that has nothing to do with the actual value of a business.
And it’s Wall Street playing Wall Street. Unless you’re selling shares, you have nothing to do with it. And in fact, you have much better information than the people who are doing these trades. Do you care if people like you and more people like you? No one doesn’t care at all, but like I use it as a piece of information that I find curious. I I see it as 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 I think, you know, I’ve listened to many of your interviews, and I mean this respectfully to everyone who interviewed and to you. The one thing that people kind of missed was kind of you. Like, not your decision making or your learning or any of these optimization things. But like, I spoke about doing my work on you beforehand. I heard about the wonderful marriage that you have. Tobi, you have a fantastic partnership with your wife. What makes a great marriage and and how do you sustain that with being CEO of a public company?
I mean, I can’t even do it with a girlfriend and a podcast, Tobi. How the fuck do you do it?
I I I met children like, it’s like super early in life, and we ended up being like so we’re in many ways opposite people, and also have such a strong bond of intellectual curiosity, and we grew together from basically being kids. We I think we we we started dating about 20 years old, which was more than twenty years ago. I mean, I’d honestly, I think very often being, like, the CEO of a company as a team production, and 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 lead to a completely different outcome, and it’s, like, there is always exactly one that is few enough for me. Like, so she’s never been on the payroll of a company, but she’s always been and I talked about all the challenges we’ve sometimes divided and 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 halfsies. Actually, she she reads faster than I do, so she usually gets to a stack faster. But what sustains a great marriage? It it is to have common projects, 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 those things back. We’re just, like, deeply curious about each other, and I think that’s been sustaining. I I don’t think I’ve cracked the code. I just got extremely lucky.
Glenn said you were probably one of the most, like, computer native technical people. He said that if Tobi could be an IP address, he would be. Yeah. 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 x, 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, it doesn’t but it’s also never tried to be off. I will always run background processes. I have a kind of brain that just like lends itself to doing this kind of thing. I think work life balance is basically nonsense. I think it’s like I mean, life harmony is kind of a better term. Shopify is unbelievably interesting. It’s a perfect vehicle for someone who’s on on a on a live mission like me and lots of my friends here. It provides a consistent impetus to, like, know 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 most interesting times? We have, like, deglobalization like never before, income inequality like never before, worse health care systems like never before, climate change like never before. I’m looking at the world quite scared, if I’m totally honest, Tobi.
Yeah. But I I I think this is the overlay narrative of the media. Again, if you if you if you go at this from truth, I’m quite concerned about climate change, but I’m also a 100%, like, we know how to solve it’s a technology problem. Wealth inequality is, like, this is the most wealthy society’s ever been. Like, no one until they recently had ever had a warm shower. Like, it’s it’s it’s it’s like the reason it’s an unbelievable luxury sphere we we have. You just we just have a built in hedonistic treadmill, which makes us forget about it all.
If you don’t have to take my word for it, you you go for something like, Stephen Pinker’s book, Path to Enlightenment, and it it just drops every single stat you’ve have seen quoted as going worse and shows you it actually gets better. I’m extremely optimistic. There there is a effect in the world which kind of sucks, but it’s gonna be temporary. And it’s I’m doing fine, but everyone else is fucked effect. And it’s actually being measured in all, like, in all societies, and it’s like eighty to ninety percent of people would say, I’m doing fine, but everyone else is doing really, really poorly or 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 wealth inequality is a thing that could be even better. But it’s also like a bad faith take that wealth inequality is a bad thing by itself, like
Do do you think that’s 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 okay and everyone else isn’t. It’s because they’re pissed off with what’s happening. And they they’re not okay. And I think if you go to the 9890% of people in The UK, I don’t know, 85 in The US or 90% in The US, who actually are living in real not great quality standards and worsening standards, they’re not happy with how they are, and they don’t think they’re even okay.
Yeah. No. It’s true. People want things to change, and there are real problems in the world, and people want to see things improve. People will vote for how they think things can be improved. 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 who votes thinks voting is presumably a good thing. The sort of system of democracy that we have and enlightened self interest harnessed towards the greater good, at least both components of capitalism are important and have demonstrably been superior to everything else we’ve attempted before.
People probably do agree that, like, completely unconstrained pursuit of 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 there, they don’t actually disagree as much. The political spectrum of point of positions you could hold is massive. It goes all the way from complete anarchy, like in 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 the people on other side are the worst, but the spectrum could be so much larger here here, and it’s the 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, what do I know? I I I built a company.
You said about the kind of the hedonistic treadmill that humans kind of face and are always on and like that continuous search for happiness. Honestly, Tobi, I faced this too. If you told me, you know, I’d be here chatting to you years ago when I started from my bedroom, think it was a joke. But I’m still not happy. I still want more. I I wanna be bigger. I wanna have more. It’s never enough. When you think about that treadmill and, you know, looking across on the bigger boat, are you happy now?
I think happiness is a temporary thing that is a terrible goal. It’s a goal that’s sold to people to keep them miserable. But you want contentment, which is very different. You want to be content. That’s that’s that’s a worthy goal. If people would start making this differentiation, what we will figure out is, like, vastly more people currently live in a state of contentment at many other times in history. Now the thing that can mess with contentment is, again, we are comparators. No one wants 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 was usual range of travel throughout your lifetime. After people pass through cities, they’re like, holy crap. This is so much better here. So people started moving to cities just because like, you you compare against what you know is possible.
So we derive sometimes contentment from that, although that’s a bug. Anyway, so happiness is bad because happiness is temporary. Like, I’m happy that 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 is the engine of humanity. It’s a thing that drives us to do everything that we actually value. It it it’s the thing that causes us to strive, things to be discontent with status quo, the thing that pioneers set out for for new shores.
It’s the thing that sets our entrepreneurs out to start companies. It’s the thing we want and ask so often in life. The best thing about us is also the worst thing about us. It’s a very, 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 I I’ve been extraordinarily lucky in so many different ways amongst those materially. It turns out, like, I I would have done this no matter what, but, like, turns out, software products turned into companies can lead to more wealth generation than almost every other pursuit and better outside of maybe real estate.
I partook in this for reasons of my own on a journey and like, partook in massive massive material wealth generation in this of which of very small percent of a wealth that Shopify created came back to me, which is still a very large number. What does that do? I mean, it’s cool. That’s probably best description. One thing it allows me to do is like, just sort of be surrounded by beauty, is the best term. I get to, you know, live in a house that was carefully designed by someone who it was the best building that they could build.
The the things I around me, like, the clothes I wear are made by entrepreneurs. Actually, entire wardrobe 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 25% better. That’s it. Past a certain point which most people clear, the average household income in North America is $60,000 a year. Most people clear this bar. Past that point, you can get the kind of things that inspire you and around you and and you increase the quality or the happiness in the day or the level of delight you encounter with with objects or maybe the conveniences by a couple 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, like, an interesting conversation with friends? Did I have did I build something today? Did I is everyone healthy around me? Those are massively bigger inputs.
What luxury makes you happy? It sounds like for me, it’s Uber luxes. Don’t laugh. But like getting in 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 I just like love really, really, really good keyboard. I know it sounds stupid, but like, I’m typing a lot. Honestly, the biggest things like a great chair, a great keyboard, a great monitor, a great mattress. Like, those things are incredible, and they are Coco Chanel said this perfectly. Although, actually, that makes the opposite point, but it’s still funny, so I’m going to share it because I set it up. The best things in life are free. The second best things are extremely expensive.
Know that well. My mother is probably co visional’s biggest fan, so I I think that’s a great one. Tobi, I love this. I I’d love to do a quick fire round with you. So I share a short statement. 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 Tobi?
That I may hold a different opinion just because through other conversations, I found that I was incorrect previously. And it it is a harrowing experience to people sometimes. There’s 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. Luca Vasquez, what’s your biggest regret? I don’t think I have any macro regrets. I have millions of micro regrets. There’s a million things we could have done better or 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, I regret not being more truth seeking there.
Is there a strategic decision you made with Shopify that you wish you could reverse?
Yeah. I mean, for a bit, I started believing some of those falsehoods, which people like to believe about leadership, like, that micromanagement is bad. Like, that is the dumbest idea of Planet Earth. There’s probably no singular idea that has destroyed more business value on Planet Earth than the idea that micromanagement is a bad thing. You’re you’re like, I don’t agree with that or that sounds crazy.
But you can’t micromanage. How do you determine what you micromanage? If you micromanage, you’re gonna create dissonance within the org because people are like, why is he managing them and not me? And then you’re also gonna create people who are 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. You should work on the machine, not in it.
Like, hire the best and allow them to do their work.
You’re correct in one, you know, frame of reference where the interventions are bad. Let me give you another example. Let’s say you’re a leader of a team, like, they’re driving the car. You’ve just been around there, and you know, like, in a straight line where they’re going, there’s a cliff. Would you not micromanage the steering wheel? Like, because that’s literally what the situation almost every lead is in right now. People are terrified.
Actually, as 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 reversibility case, not true in the everyone’s fatally crushing case.
Oh, No. If everyone’s fatally, yeah, then you obviously have to intervene. But the majority of things are reversible. Very, very few things are irreversible.
The thing you described is like, okay, is this sort of Dilbert esque view of a leader. Right? Like, they are like pointy head boss comes and changes like mousse cheese around. That is not micromanagement. That is just being extremely bad as being being a leader. What you actually want is you want your entire company to compose into something that is sort of like an idea lab where people who are closest and the people who have a like, the the biggest perspective come together to make the best choices.
For that, there’s a role for absolutely everyone in in like, in this. And, you know, in most cases, what you do is you find someone, like, you find a CFO who’s amazing. You work with them together. You 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 and the book. Presumably for a bit, you should trust but verify because, again, you are, like, trying to like, you actively have to build trust with people.
Trusting by fiat, trusting by name of a role is not a great idea. You can use someone’s background as like a massive precharge 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 never you you always still have it for everything. But you can share your responsibility for all parts of a company with your leaders and other people.
You don’t 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 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 a company at some point, may maybe because I’ve hired someone. But I also hold the responsibility therefore for for for all outcomes. But you find founder led 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 world of consulting is basically one large way of outsourcing responsibility for their choices.
That’s the main product they are 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 and you should be very, very clear that you’re looking for the best rather than being right. Again, which is also not micromanagement. This is actually just, I mean, called microleadership. It’s like helping editing the final thing.
A great company is looks or great products look to the users like they are a book written by a single author. They are logically consistent. They are putting 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 like the same pattern teaches you about other parts of the system, especially if it’s a big system. Doing this with thousands thousands of people requires 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 gonna do a million things that help, like, for instance, like, just like, with something like Shopify. Shopify is absolutely massive piece of software, probably one of the biggest pieces of software on planet earth. 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 the 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.
The floor quality of execution for everyone who just use the design system is very high. The floor is high. However, the ceiling is uncapped, which is the mark of a brilliant system. That’s the most important thing you can you can create. But the process of creating Polaris, this design system, is something that I was involved with because it 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 all the work and I did the project, but I hold some co authorship over the creation.
Someone would call that potentially micromanagement saying, hey, Tobi wants to be part of the design review for the drop down component and these kind of things. But now it’s like there’s just deep appreciation for the craft that’s caring and that’s perspective that’s honed over nineteen years of doing this kind of thing. By way, this is the worst lightning round anyone’s ever had, by the way, at this point.
They have they have a fight. You you gave me this toy. But but the the options you have are infinite. You you have an infinite amount of options to become micromanager on. You said about the drop down there. As you 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 it’s not gonna be functional leadership. You you have to, at some point, not be a micromanager.
You have to you have to be able to trust people. You you have to work with like, I do not need to look at dropdowns anymore because I’ve worked with the Polaris team and trust trust the leadership and trust the principles. And therefore, we are sharing responsibility for Polaris, but, like, I’m extremely confident without looking looking at all the work. However, if it is like, hey, let’s make a new version of Polaris, they know that, hey, let at least tell Tobi 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 couple months.
And so the company understands that information has to flow and that we we work together as a team. And this might outrage you. Every great product on planet earth has been made like this. There is no other option. It is always a collaborative effort of a lot of people where they have a common thing is that there’s a common culture, common belief system, a common set of aesthetics and and and and things, but also work together of a lot of people from different layers with no regard for post World War two concepts like org charts and so on, which are like, even the military doesn’t use org chart, like like like chain of commands.
In fact, they they usually invert, 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, company made made by a crafter and by founders of crafters, craft craftspeople. Again, I literally apprenticed in my craft for craftspeople. And we support the people who are building, but we support them by helping them also know the train, know where to go, have a baggage train show up at time and, you know, solve a lot of cognition challenges and and and help everyone do some of the best work of their careers and their lives together.
And this is what it looks like. And, you know, you bet this is how Walt Disney designed the 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 of its times.
Penultimate one, I promise, because I I should that would be totally weird. But when you think about leaders that embody this for you, who do you most look up to? Is it Steve and Johnny?
No. No. I who who embody this? I think Walt 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. I I 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 in doing better than everyone’s done it before.
In fact, it’s not even that hard. They’re not that good at building companies. They’re not that good at building products. They’re not that good at making teams. They’re not like like, competitive is like a like, maybe a three out of 10. They’re gonna know how to do this way better in, a hundred years from now. So so just, like, try try to be a four out of 10, and you, beat everyone. You know, all these other amazing founders for time, Elon, Zach, the contemporaries and and and and and and the great founder led companies that we finally get to build, you know, they they are probably the fourth out of 10.
But like, there has been just limit. Like, if someone is like has the perfect, like, is perfectly insightful, you could build the probably eight out of 10 right now. Could be one company which is so vastly superior to literally everything else, just better firmware. Better model of the world, better like set of beliefs, maybe better technological systems. Who knows? You’re gonna figure it out. You’re figure out basically everything in the next hundred years. That’s my belief. So at the end of our careers, likely, we can actually sit down saying, hey.
What’s the stuff we didn’t yet know in the twenty twenties that later on we’ve discovered? And I can tell you, you’re going to be embarrassed by our lack of it’s stuff we already like, someone’s already done and probably brought about in some obscure book or some Harvard Business Report. Probably not. They they don’t write on interesting stuff. They just sort of, like, write 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.
Here’s a statement for you. I think you can learn more by studying World of Warcraft raiding guilds than 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 and everything is more interesting than you thought. And so that’s fun. It’s just so fun. It’s fun to have a task. Like, do you have this thing where it’d be like, there’s millions of entrepreneurs, probably with tens of millions more who want to reach for independence?
And the best way they do this is if they know where there’s, like, some kind of product needed and know how to make it and and and and maybe can help a little bit with that. And then we take take care of, like, just a lot of the drudgery of, like, partaking in the world of, like, global commerce and and Internet selling and so on. And not only that, we are also, like, pulling value out of the latest things that are possible. Like, this is the greatest part of the job.
Right? Like, what are the things that are just about becoming possible right this moment? And what is the angle they should take with those things to to give it to millions of small businesses? Like, maybe one some of these things are extremely valuable and they might have it before the big box stores that they might be competing with. How cool is that? Like, since then, is a leverage and balance tilted in favor of a small? That’s good because small is more nimble. And so it’s cool to partake in, again, some of the most interesting times on in human history and have a task with all the change around us, for our technology, all the stuff that’s 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 and now we get to play with it. And and then it’s like, you know, we get to have another one of those idea labs, ideally done in proximity, where we can figure out what is it we need to build, and then we build it. And that’s awesome. I love you know, I love that. It’s the best loop in the world.
Tobi, we’ve absolutely nailed the quick fire round. Think top marks to both of us. Also, the best sound bite on World of Warcraft. Honestly, I so love this. There’s reasons and shows like this why I love doing this so much. Thank you so much for being such an amazing guest, Tobi, and I so appreciate it.
Awesome. Yeah. Thanks for doing this. You’re doing a fantastic job of this podcast. I love it. And and with this show, I love what you’re developing here.
I had so much fun doing that show. If you wanna see the full video episode, you can head over to YouTube and search for 20, and you can sign up for the newsletter on 20vc.com. But before we leave you today,
· Sponsor read0 min · 456 words
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 two, ISO 2,701, HIPAA, GDPR, and others. Secure Frame’s industry leading compliance automation platform paired with their in house compliance experts and former auditors helps you get audit ready in weeks, not months, so you can close more deals faster. Secure Frame makes it fast and easy to achieve and maintain compliance, so you can on serving your customers and growing revenues.
Automate your security and privacy compliance with Secure Frame. Schedule a demo today at secureframe.com. So if compliance is one thing you always have to prioritize, you also always have to prioritize your team and work. Well, it’s truly global today. And until now, there’s been no HR platform that’s been able to handle everything for everyone no matter where they are in the world. Well, Deal does exactly that. It handles all things for global teams. It allows you to easily consolidate contractors, EOR employees, and local workers in one platform with a tool built to evolve with every stage of your company’s growth, no matter who, how, or where you want to hire.
So whether you want to comply and work with a contractor or a project in Argentina, hire an employee where you don’t have an entity, or run payroll for a direct employee overseas, you can do just that and so much more with deal. It’s way less HR admin and a whole lot more peace of mind. Simplify global team management, payments, and HR so you can hire faster, streamer in more processes, and stay compliant always. To see how Deal can scale with your team, visit deal.com/20vc. And finally, are you building enough conviction to outpace other investors in this changing ecosystem?
Tigus helps VCs get under the hood of their investments quicker, map evolving markets with deeper research, monitor the financial health of portfolio companies, and crucially source new deals. Tigus is trusted by top firms like Redpoint and Spark Capital for everything from expert calls and transcripts to quickly surfacing insights across filings, comps, and benchmarking. So find out why a majority of the top venture funds are using Tigus on a daily basis to differentiate, consolidate, and accelerate their research. Head over to tigus.com/growth for your free trial. As always, I so appreciate all your support, and we have an incredible The Memo episode coming to you on Wednesday where we profile an incredible company that scaled to $600,000,000 in revenue with absolutely no venture funding.
Yes. We have Mike at ButcherBox on the show on Wednesday.