Tobi Lütke, Shopify

Tobi Lütke is the co-founder of Shopify, where he has served as the company's CEO since 2008. Under his leadership, Shopify grew from an online snowboard shop in Ottawa, Canada in 2004 to the world's leading e-commerce platform, powering over 4 million merchants in more than 175 countries. The company went public in 2015 at a $1.27 billion valuation and has since grown to a market capitalization exceeding $200 billion. After dropping out of school following the tenth grade in Germany, Lütke completed an apprenticeship in computer programming at the Koblenzer Carl-Benz-School. He moved to Canada in 2002 and launched Snowdevil, an online snowboard shop, in 2004 with Scott Lake and Daniel Weinand. Frustrated with existing e-commerce solutions, Lütke built his own platform using Ruby on Rails, which became Shopify in 2006. He became known for pioneering accessible e-commerce tools, contributing to the Ruby on Rails open-source community, and championing the idea that entrepreneurship should be available to everyone. His accomplishments include building Shopify into one of Canada's most valuable companies, being named "CEO of the Year" by The Globe and Mail in 2014, receiving Canada's Meritorious Service Cross in 2018 for his contributions to the technology industry, launching Shopify's Sustainability Fund in 2019 to invest in climate solutions, co-founding the Thistledown Foundation with his wife Fiona McKean to support healthcare and environmental causes, and serving on Coinbase's board of directors since 2022. Episode show notes: https://www.davidsenra.com/episode/tobi-lutke Survey: https://forms.scicommedia.com/t/mw83tpmsRzus Made possible by Ramp: ⁠https://ramp.com Eight Sleep: https://eightsleep.com/senra Function Health: https://functionhealth.com/senra Chapters (00:00:00) Companies as Social Technology (00:05:27) The Value of Reading Books: Cheat Codes for Life (00:07:28) Post-IPO Crisis: Cosplaying as a CEO (00:07:54) Competition vs Rivalry: The Power of Healthy Competition (00:16:02) COVID as a Turning Point: Rebuilding the Executive Team (00:18:21) Hiring Founders: Building a Team of High-Agency People (00:26:49) Shopify OS: Engineering the Company from First Principles (00:36:48) Compensation Innovation: Giving Employees Full Agency (00:40:41) The Psychology of Identity and Affirmations (00:48:43) Differentiation Over Perfection: Making It Your Own (00:50:31) Context Podcast: Documenting Decision-Making (01:26:36) The IPO Decision: Going Against Silicon Valley Orthodoxy (01:35:08) Building a Company Worth Working For (01:41:50) Hiring for Spikiness: Finding Non-Conformists (01:48:28) Office Design Philosophy: Creating Space for Excellence (01:58:54) Video Games as Business Training: StarCraft Lessons (02:07:06) AI Revolution: 2026 and Beyond (02:11:44) Focus on Craft: The Unquantifiable Elements of Excellence (02:21:08) Survivorship Bias: The Importance of Entrepreneurial Exposure (02:23:22) Closing Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02David Senra?

  One of the things I admire most about you is like you've been running your company for 21 years, something like that. I love people that do things for a long time, people that chase excellence, that try to be great. My entire life is founders, right? So during the day, I read biographies of history's greatest founders, I've read like 410 of them. And then at night, I hang out with founders. I don't think I have a single friend that's not an entrepreneur. And then I'm always asking the founders I most admire, who are the founders they most admire? And your goddamn name comes up over and over and over again. And what they talk about is that you have very unique ideas on company building and management. And they use the word singular a lot. So I want to kind of like lay out how you think about building companies,

• 0:43David Senra?

  building products, building technology, and then, you know, spreading the gospel of entrepreneurship. I want to start with one thing that you said. You said companies are technologies themselves. What do you mean by that?

• 0:53Speaker 01

  In a lot of ways, like, I mean, like, take the social angle. Like, a lot of the companies are social technology in the sense that they allow us to go all in. Like, the only time you're really allowed to spend, I don't know, eight, I'm gonna say eight because that's the right number to say, really, like fucking 14 hours a day, right? Just singularly pursuing a thing is like, I mean, we want kids to spend this time in school, and that's okay. And then university, you know, dedicate yourself. Other than that, like, you can't just like not have a job, but just be like really into things. It's socially not acceptable. So like, company building turns out to be the perfect excuse.

• 1:36Speaker 01

  Once you call it a company, it's not like tinkering around anymore with your ideas. And you get to explore things. Well, a company fundamentally allows you to do is like just run the counterfactual to the world you see around you, right? Like, you get to try to build a thing that you think ought to be there. And then you means test it against the market. And if the market agrees with you that this thing needs to exist, it moves energy in the form of money back to you so you can do more of the thing that you were pursuing all along. And not only that, it's like self-financing. Like, if you find out, like, again, I started a company that I didn't think was gonna be, like, have this very, very big market.

• 2:16Speaker 01

  And along the way, it just like, the market pulled Shopify out of the project I started essentially. You know, that's an incredible intelligence to tap into. So you put all these things together and you say like, well, look, companies, the concept of companies is not that old. It's like we're on a 500 year run and sort of kind of extracted from things called companies, which were actually more like quasi governments, like the East India Company. And so the modern company is not that old. I find that if you take that mindset, that like companies are just sort of a path dependent solution to a social and somewhat legal problems.

• 2:54Speaker 01

  They allow thousands of people to join your project and it's called a job and therefore everyone accepts this. And obviously you can make money, so it's a good deal. And then you can figure out if this counterfactual of yours might be correct or needs updating along the way or any of these kind of things. And you could, at the end of the day, if you are lucky, you look with other people who are really all in and like inspiring and like taking it further than you ever think. I just like the work thing is just like, I just like, I marvel at the institution of a company in a way. Like because if it wouldn't exist for some reason and someone would propose the work idea now, it would sound insane. Like from first principles, none of this makes sense, really.

• 3:41David Senra?

  Well, I heard you say something that was fascinating, really piqued my interest. When you're like, we do not know how to build companies yet. All companies are terrible.

• 3:49Speaker 01

  Yes.

• 3:49David Senra?

  Including mine, which you said, and you know, that's hilarious when somebody's, you're running a 200 billion plus dollar company. And you think that in the next 20 years, we're going to look back at what we were doing at this point and be embarrassed by what we were doing. Why do you think that?

• 4:05Speaker 01

  Because it's like everything else. I'm sure when you listen to your first podcast, you're like, oh my god.

• 4:11David Senra?

  Please don't.

• 4:12Speaker 01

  But like it's honestly, this should be seen as the most joyous of like moments. You should actually do it if you haven't done it.

• 4:20David Senra?

  No, I do it all the time.

• 4:21Speaker 01

  Okay, good. Because what you, the difference between that and what you would do today is you progress, right? And as a computer programmer, I experienced this all the time. I'd look at old code and I'd say, what the hell? Like this is terrible. Why would I do this? This is way too abstract and complex. And then I made it better because I now have the skills to do so. And one of the saddest days of my life was when I opened Old Court. I was like really impressed with how good it was.

• 4:45David Senra?

  That was one of the saddest days?

• 4:46Speaker 01

  Saddest day in my life because I'm like, holy shit, the implication of this just hit me like a like a train, right? Like.

• 4:53David Senra?

  Then you weren't progressing, you weren't learning.

• 4:54Speaker 01

  Exactly, it figures because I was programming all day. I was like trying to, you know, uh, build a company instead, um, which honestly is very, very similar.

• 5:02David Senra?

  This is one of the things Daniel Ek told me about you.

• 5:04Speaker 01

  Yeah. Here's what I'm observing, like you, I read a lot of books. I, I, I try to figure out, um, like, uh, you know, I think, uh, someone, uh, like if you don't read books, you live a lifetime. If you read books, you live a thousand, right? Um, so it's.

• 5:19David Senra?

  I'm going to interrupt you real quick because I took notes on this podcast six years ago. This is the first time I came across you and you said, uh, books are the closest thing you ever come to finding cheat codes for real life. You can access the entire learnings of someone else's career in a few hours.

• 5:34Speaker 01

  It tracks, doesn't it?

• 5:35David Senra?

  Yeah. I mean, I dedicate my life to this, so of course I'm going to agree with that.

• 5:38Speaker 01

  I mean, you know, Chris was supposed to agree with me, but like I, I really think we need to shout this more from the rooftops, right? Like it's, you know, like the one weird trick seems to be just like read books, right? Like it's, um, and it kind of doesn't matter. Let's make a habit of reading books and like ideally change Jira every three books or so, at least for one book. And then that alone will give you a range that you can draw on for basically everything you'll ever do. So like, look, I, I, I read lots of books, lots of them, you know, just like, you know,

• 6:10Speaker 01

  especially when I went from programmer to a business, um, uh, like realizing I have to just learn business really quick. I, um, I got really dismayed with the quality of a business books pretty quickly because frankly, I think the business books are largely written by,

• 6:29Speaker 01

  by the people who have time, well, not the people who actually build companies frankly. So, um, so you read between the lines as well. Depends on like, if, if a person who started a company or a person writing book is a salesperson, every problem can be solved with sales. If a person is a marketer, clearly every problem can be solved with marketer. And I mean, at least that I can take away to as a trap to not fall into, right? So I was determined to not, um, be the engineering type founder who is going to see everything as an engineering problem. Because that would be called blindness and like I would, that's what kept my capabilities. So I really tried everything and learning like, you know, just how to, you know,

• 7:10Speaker 01

  build a team in such a way that I delegate everything and I have my different business lines and, you know, arrange things. This is sort of after the IPO and I realized I have to be a very serious public company CEO. And so it almost killed the company, honestly. How did it almost kill the company? It was actually COVID that saved it at this point. Like I, I had the inclinations that something was really, really going poorly. It was a time we didn't have a lot of competition, so which is also really, really hard for businesses. It's not a good thing at all because again, you don't get, you don't have good rivalry and you can't, you can't sort of, like even if something seems really good, you don't know because there's no one else to keep you honest about it.

• 7:54Speaker 01

  You have a distinction between a competitor and a rival and you think rival, competition is one thing, rivalry is really good. I mean, it's the same, but it depends, it's a mindset change. It's like, I think if you, again, if you compete with another company, like there's a lot of, we need also a version of what they have copying, like you do with Xerox strategy very quickly. Companies tend to get obsessed, like there's companies which have very, like the most active channel in this like is where is a competitive analysis channel, where people just bring everything everyone else is doing. And I think that while that has some merit, I think the problem is it makes companies very reactionary, right? Like I, you know, but like in, in, in the arts,

• 8:39Speaker 01

  part of anyone, everyone's art studies is, or like some fine arts, you, you, you copy the great pieces, like you make copies of great works. Your next painting is not at the quality of a Van Gogh, you just copied, right? Like, so mimicry is actually not an excellent way of getting to excellence. And companies end up falling very much into this. Whereas if you treat someone like a company in your space as rivals, much easier to have a positive outcome there because rivalries inspire you to be best. Like Agassi could not have been Agassi without Sampras being there, right? Like, and he very, very clearly states this in his book.

• 9:23Speaker 01

  The Sampras that existed during the Agassi era, that Agassi understood, wasn't a real person. When you read Sampras's biography, he just liked tennis.

• 9:33David Senra?

  Yeah, and Agassi hated it.

• 9:35Speaker 01

  Agassi hated it. And so the rivalry he created for himself created him, you know, in a very real way. In The Last Dance, which I loved, like Michael Jordan, like he admits that he might made up a slide at some point, which to me is like one of the most profound moments.

• 9:52David Senra?

  Sometimes I play The Last Dance in the background while at work. It's my favorite documentary. My second favorite one is The Defiant Ones. It's about the partnership between Dr. Dre and Jimmy Ibeen, the multi-decade partnership. That's the description. That's not what it's about. It's one of the best documentaries about entrepreneurship.

• 10:07Speaker 01

  Interesting. Hip hop rap history is incredibly entrepreneurial. It's fantastic.

• 10:11David Senra?

  So we just recorded with Jimmy Ibeen, who's the star of the documentary, two days ago, or whenever, I don't even know what day it is. And that's exactly what he said. It's like they understood the business of music before anybody else.

• 10:20Speaker 01

  That makes perfect sense and totally tracks. You can see it from the outside. It's, we actually, we see it from the inside. Like, it was the first category of music that just like killed it on Shopify. It's like, they're just like so, like, opportunities converted into products, like, like that. And it's, it's like, they made different. It was really, really cool. This is a beautiful thing about Shopify, it's a front row seat to.

• 10:47Speaker 01

  Just seeing how high agency the different industries are and how quick they absorb new ideas. And it's just like, anyway, it's like a different topic, but like

• 10:55David Senra?

  Almost like in video game, like a god level view of entrepreneurship, because you, how many entrepreneurs on the

• 11:01Speaker 01

  It's like millions, right?

• 11:02David Senra?

  Yeah. And you're drawing like insights for your own work from the entrepreneurs on your platform. One of them, we'll talk a lot about today, was like the importance of differentiation. But I want to come back to that. I want to go back to like, so you were thinking, okay, right after the IPO, I'm going to approach everything. This is like an engineering problem?

• 11:19Speaker 01

  I'll be, I'll be a cosplay company, a public company CEO, like 60 year old guy in a suit. Like, okay, legal background, right? Like this is sort of what everyone emulates for whatever reason. And it just worked really poorly for me from a product perspective. A company did fine, right? All the way through. Covid happened though. And I'm like, okay, so what my company needs here for me is like five different things. One of them is all plans are invalidated fundamentally. Like, everyone who has a plan, just please throw it out. We need to go and like, go for everything we're doing and re-derive it because, again, everything is based on a very long tree.

• 12:03Speaker 01

  Like you start with axioms and then you make a huge amount of decisions on top. And then you get to a conclusion and that's means this is how you spend your day to day building this thing because of these things. If any variable along this way is invalidated, what you should be doing is re-derive the entire thing on top, right? Like you should always prune back the decision tree all the way there and go forward. People not being able to go out of their houses. It's one of those things, like, I don't think we all knew that was a core assumption we had, that people could just freely move around in the world. But we got told that we can't do this anymore. And it ended up being quite long during Covid, at least in California and Canada and some places. So we need to re-derive everything. And that was kind of clear to me instead of what I, you know,

• 12:48Speaker 01

  that's how you structure a computer program, frankly. I went through the entire roadmap and what I've figured out is first of all, that was really, really hard to get. And people were fighting, even like very much resisting. Talking about everything that's going on. And I found out why, because like, there's just a lot of boondocks going on. There's just like random projects by random people that I would never found out about. I would like. Why did you not know there was going on in your own company, though? Because the company was like, let's say, like, um, four or five thousand people. You know, it's sort of caused a disassembly. We started in Ottawa, Canada. We, we had like Toronto office and Montreal office and so on. And so it just turned out that like, you know, in the Toronto office, uh, there was a fairly big project to build the features to add to Shopify.

• 13:33Speaker 01

  So, uh, you could use it for running a supermarket because, you know, just they decided that supermarket industry is very large and we should go and, uh, capture one percent of order, like in the Dilbert comics. And so, uh, you know, and frankly, it like, I, I'm not saying those were wrong decisions. The, the, the sort of really surprising thing about building a business or just in decision making in general is that, um, making the right decision is actually child play usually. Like can make wrong calls, which, which end up because of world changes, end up being wrong call later and so on. That's a different thing. Um, um, but like most of the time, if you like the bad options in front of you just prune themselves away. They just don't make sense.

• 14:17Speaker 01

  They're too expensive or just like, uh, off mission or whatever. You, the problem is, and I think school unfortunately accidentally drills this into people. It's that there's one right answer is sort of what people think. And, um, once they find a right answer that could plausibly accomplish the goals that they set out, they go with it. But that's like, well, there's probably hundreds of great answers. And one of them is like far less work, far more, um, especially in an engineering project. Like the best solutions are always modular and components. You build one thing and it will work with everything else you did.

• 14:57Speaker 01

  Um, lots of the bad software that people use is a things where, which are just like hairballs inside. They're like, none of the pieces fit together and a huge amount of code has to be written to extend the new thing. Make it usable from everything else. And like, I'm not going to bore you with those kind of details, but, um,

• 15:15Speaker 01

  If you look at the project brief, the team killed it. Probably everyone made their bonus, they delivered the thing. It's like an island upon itself now that, and after it's delivered, nothing else in the product works.

• 15:28David Senra?

  So you were looking at things as like cosplaying a CEO or business person as opposed to an engineer?

• 15:34Speaker 01

  I was trust falling. I was like saying, okay, cool. You seem passionate and you seem to know what you're doing. I trust you to do the right thing. And when I hear, you know, obviously we're gonna keep talking. You give me updates on things. People learned pretty quickly what are the projects that I'm interested in. Taught me about both and nothing else. People learned how to direct my attention to the things that they wanted to have my attention.

• 16:00David Senra?

  So how did you fix that?

• 16:02Speaker 01

  The moment I went through absolutely every project I did myself, took like many, like 16 hour days. I canceled probably 60% of the projects. And over the course of a year, I turned over every one of my executives. Like this is basically a consequence of this because I just realized that in many cases, the core skill was, well, I mean, I don't want to be unfair, right? Like it's just that trust was broken in many cases. And in a real crisis like COVID, again, COVID was hard, hard, hard, hard, hard. Hardest time of my life for sure. And in a crisis, if everyone is a one before, some people go to zero in a crisis. Some people go to 100. And I found it's almost unpredictable.

• 16:47Speaker 01

  In fact, if I would have been betting before COVID about who's going to be contributing the most, I would have been wrong, I think, entirely.

• 16:56David Senra?

  Why do you think that is?

• 16:58Speaker 01

  I've been thinking about it for a long time and I still haven't gotten a good answer. I don't think they would have known. This is the interesting thing. I think a real crisis tests you in a way that nothing else does. Nothing prepares you right for it. I think at the end of the day, the thing that I have found is people who can adopt the fastest actually quite self identify. Now I would be able to predict it. Very simple. Have you started a company before? So Shopify is by founder, by founders, for founders, causing more founders. Right? Like it's a celebration of entrepreneurship. We believe entrepreneurship is glorious and people who reach for their heroes and doing

• 17:41Speaker 01

  more than they heroics, go on a hero's journey with lots of naysayers, overcome incredible odds and lots and lots and lots of headwinds. That conviction runs really deep. Sometimes we buy companies, of course. Many of the people we purchased are still in Shopify. People don't like stay for a very long time because I think it's such a place for founders and for high agency people. So I always had a Slack channel with all founders of our companies that we purchased. We always, I did a founder offsite with them once a year. They're just like, because I find their advice just to be so good. They all have been responsible for people's livelihoods and that changes you. So I went to the founders channel and said, guys, I need help. Right?

• 18:25Speaker 01

  Like this is places it's crazy here.

• 18:30David Senra?

  Had you already started turning over your executives?

• 18:32Speaker 01

  Yeah, once I realized that I was like, and it wasn't like one moment. It was just like.

• 18:36David Senra?

  How did you know that instinct to go to the founders channel and ask for help?

• 18:39Speaker 01

  I think that at a moment of like, where the fuck do I go? Who do I have most in common with and who can I, who can actually relate to the types of problems here? Because again, my relationship to Shopify is different, right? Like I started it, right? Like it's like, it's just like, it's different from everyone else. But the second best thing is talk to people who have had this type of relationship with the thing they created. You know, I asked a lot of the founders to become my executives. In some cases, I took people from individual contributors in an engineering team and put them in charge of a very large thing. You know what? At all, every one of those things worked. And it was like really remarkable because it really fed into an intuition I had anyway.

• 19:20Speaker 01

  And what I found is during COVID is the founders of company that actually. Not doing well because they were like similarly managed. They were like irritants.

• 19:31David Senra?

  What does that mean?

• 19:32Speaker 01

  They don't settle. They they they talk about absolutes. They if something is shit, they say so. It doesn't matter if everyone has agreed to move on or something. It just it gnaws on them in a way that's deeper than this other thing.

• 19:45David Senra?

  And that's exactly what you have inside of you.

• 19:46Speaker 01

  Exactly. And so I I I feel like this is it's a very special thing. And it's companies reject it. Companies cocoon them. Sometimes they find sort of they give outskirts like the skunk work team. It's like just like it's daycare for for people who otherwise tell you that your stuff, your shit doesn't smell, right? And shit does smell. So once I'm like, no, you you you don't get to put them in like founder daycare. You you I'm gonna put them right right in front of you, like in fact, on top of you. So and so, you know, the difference that made to this business is nuts. And so this is why I'm saying COVID saved Shopify because I I needed to take a move.

• 20:30Speaker 01

  That was like very much, okay, I built this company. I got to this point. It's important. It's actually maybe even more important during COVID than before because it was kind of like for millions of small businesses, their livelihood for this time and only way to make livelihood. And I'm super proud of what we did because I think the businesses that started in Shopify and came early, like actually grew and did better.

• 20:53David Senra?

  Some of them grew faster than you. You said somebody beat you guys to a billion.

• 20:56Speaker 01

  Yes, which is the craziest thing. Where did businesses ever raised their customers like that started on the platform for it's it's the greatest. I love this thing. And so, I mean, again, like they're fantastic, they're heroes, they're glorious, they're wonderfully discovered. My founder, my my customers have the same irritation with my software. And like they're telling me, it's like it's perfect, right? It's exactly what I want. And so this was one of those moments saying, you know what, Toby, like, like, maybe you didn't build Shopify completely by accident and your intuition might have been actually helpful and cosplaying someone else is probably not what you need to do.

• 21:31David Senra?

  At that point, you were running Shopify for how long?

• 21:34Speaker 01

  Uh.

• 21:34David Senra?

  Fifteen years?

• 21:35Speaker 01

  Now, it's, yeah, about.

• 21:37David Senra?

  So that you were fifteen years.

• 21:39Speaker 01

  Fifteen years.

• 21:39David Senra?

  This is very common biographies. I think it would surprise people like, oh, why did it take so long to figure it out? It's like, no, it takes a long time to actually build the skills. And then the important thing about intuition has to be refined.

• 21:49Speaker 01

  Yeah.

• 21:50David Senra?

  So it's like, maybe in 2005, you shouldn't have been trusting your intuition.

• 21:53Speaker 01

  Trust your gut is sometimes good advice, but it really depends on your gut. So it's like, um, no one, no one is born with intuition for building businesses. Because first of all, building businesses are completely, every decade is different. Like, some problems are persistent.

• 22:10Speaker 01

  Like, I laughed, I listened to, I think, an episode you did on Larry Ellison. You were describing his frustration with problems in his sales team, which literally I had to. Like, it's like, you know what? I didn't actually live, have to live that horror. I could have actually, like, there, if I would have read the right.

• 22:27David Senra?

  If you read software, any of the biographies, or listen to founders, there they go.

• 22:30Speaker 01

  The incentive problems are on commercial teams, it's like.

• 22:33David Senra?

  But that's, that's amazing part. I'm glad you just, you picked it up because he's like, I'm fucking embarrassed. He's like, I'm forty something years old.

• 22:40Speaker 01

  Yeah.

• 22:40David Senra?

  I've been running this company forever and I didn't understand that incentives with my sales team mattered. And they almost destroyed his company.

• 22:47Speaker 01

  Yeah.

• 22:47David Senra?

  They almost went out of business.

• 22:49Speaker 01

  I usually listen to podcasts when I'm sitting in my racing simulator to practice for my next race. And like, it got to that point and I had to like, okay, I have to stop and just listen to this because I'm, I'm just feeling so much empathy for Larry Ellison of all people. How funny is that? So, anyway.

• 23:05David Senra?

  Who's that empathetic person? Before you move on, because I love where you're going. I can't help myself, because you know this. It's like, when I hear you saying, like, I'm getting rid of executives. I'm going to build an executive team of founders. That's not a new idea. Rockefeller was doing that 150 years ago.

• 23:20Speaker 01

  It's interesting how the building blocks that largely Rockefeller invented. I mean, we call these things trusts because it was, you know, like, that was a term they first used there.

• 23:36David Senra?

  Toby's relentless dedication to improving his company reminds me of my friend Kareem, who's the co-founder and CTO of Ramp. Kareem is one of the greatest technical minds working in finance. I spend a lot of time talking to Kareem, and every single conversation centers around his obsession with crafting a high-quality product and using the latest technology to constantly create better experiences for his customers. Like Toby, Kareem believes that nothing is ever good enough, and it can always be improved. Kareem is running one of the most talented technical teams in finance, and they use rapid relentless iteration to make their product better every day. So far this year, Ramp has shipped over 300 new features. Ramp is completely committed to using AI to make a better experience for their customers

• 24:19David Senra?

  and to automate as much of your business's finances as possible. In fact, Kareem just wrote this: "AI is all I think about these days. It is our duty to be first movers and push limits so we can make the greatest possible product experience for our customers." That sounds a lot like the approach Toby uses. Both Kareem and Toby never rest on their laurels and use rapid iteration to invent new products for their customers. Many of the fastest-growing and most innovative companies in the world are running their business on Ramp, including Shopify. Make sure you go to ramp.com to learn how they can help your business save time and money. Let AI chase your receipts and close your books so you can use your time and energy building great things for your customers, because at the end of the day, that is what

• 25:04David Senra?

  this is all about: building a product or service that makes someone else's life better. That is what I'm trying to do, that is what Toby has dedicated his life to doing, and that is what Ramp has done too. Get started today by going to ramp.com. So now you have the executives. You're going through the most difficult part in your life.

• 25:21Speaker 01

  Yeah.

• 25:22David Senra?

  And you realize, oh, I'm cosplaying. I'm gonna go lean into my intuition.

• 25:26Speaker 01

  Yeah.

• 25:27David Senra?

  This is another thing why I think that decision you made six, seven years ago, however long it was, is why so many founders like study you, respect you, take pieces of like your philosophy as well, because you're like, god damn it, I'm just gonna do this the way I wanna do it.

• 25:39Speaker 01

  I was like, okay, I need to try something different. You have to do things differently, axiomatically. Like, obviously axiomatically, if you do the same thing, you get the same results. Differentiation requires new ideas. You are...

• 25:53Speaker 01

  Instead of figuring out, like spending the next 10 years of my life, figuring out how well I can cosplay someone else, what would a company look like if it just taps entirely into my intuitions, like in my biases? I'm doing literally the opposite now as I did before because this didn't work, so maybe the opposite works. And worst case, I triangulate the midpoint between those things. So enabled by the very clear, fast and obvious success of asking people from Founders Channel to step up and run company with me. My real set of intuitions here, again, intuition is your entire life's story rolled out for you to make a snap decision in a moment.

• 26:37Speaker 01

  What does my intuition say about what a company actually should look like? Like, let's forget about the path dependence, let's go full tabular rasa and go up from Axioms. And I started with really, really, really, uh, nothing. Like I started like a project on GitHub, literally. So engineering tools, my intuitions again. What is the first principle of a company? Like, what is like, what are the inputs? What are our decisions? Like, put in config files, what titles exist? What levels exist? How, you know, I asked for all the sales, like compensation data or the market data and put them into the repository.

• 27:20Speaker 01

  I turned them into machine-readable files because I got MSPDS and so on, so on. So I built a thing that then created, like at the end, had all the information to create a model of a company. Like literally, this is Python code, um, which takes configuration files that we agreed on, things like how many people should report to a manager, all these bits, and then computes them, uses something called a solver, like a SAT solver specifically. And then with all these constraints, all these inputs, what should Shopify look like? What departments exist? What level exists? How many people are there in which group and everything? And of course, the first version very utterly incorrect. And then I realized. Were you doing this so long?

• 28:05Speaker 01

  I started it and then I got like two, three other people in it to help me this with this and really, really got into it. And so this is this is called Shopify OS, this Shopify operating system. It is really not very part of Shopify now. What it did is it became irrefutable that we didn't know all the principles. We had like something, it was eight thousand people in a company and there was five and a half thousand different titles in a company. And it's like, so and some of them are just senior and senior staff, but in some groups, senior staff was lower than director and some above. And it's just like, it just, when I tried to make something software addressable and

• 28:49Speaker 01

  try to reproduce it, it showed every crazy, unviable choice in the company very, very easily. So there's a system in engineering, not actually a well-understood part of it, but I think it should called desire state systems. And what desire state systems are is it's a thing where you say, okay, here's what should be. You hold that up to what is, like you click on a website on a link and your React library behind it, all it does is, it says, okay, I compute what it should be, I see what it is, and now I figure out what is the minimum amount of steps I take to get this to there. And that's what you see on the web browser. I need a desire state system for this company.

• 29:32Speaker 01

  So we have this model, we create it, and then we hold it up to the company and the job of HR is to be this reconciler, like how do you take the minimum steps to get from here to there or change what we have in this system to approximate what we actually want. So this is very technical. Here's the effect of it. Think about how much politics this removes. Then my head of sales comes to me and says, hey, I need 15 new set people. I can put this now into the system and says, well, that means. You have to either make these changes or you're gonna lose some of your engineers. Or like, because the system, based on our agreements, recomputes everything. So I have, we can always look at the counterfactual.

• 30:16Speaker 01

  And then it's not like, yes, boss agreed while playing golf to hire fifty more salespeople. And now someone has to carve, like, you have to find a pound of flesh somewhere in the engineering team. And suddenly, you don't actually work on innovation anymore because you never actually made the decision to not hire engineers because your budget doesn't allow anymore. Because, but you did make the decision to hire salespeople. And maybe this is the right decision. But now we can actually look at the consequences of every one of those things. So it was hugely successful because it just created such a legibility for us and such a simplicity. It also just told us that so much was undecided. Like, for instance, we took the concept of, in engineering, this was already around. Individual contributors is a really, really excellent career track, right?

• 31:01Speaker 01

  Like, you can make as much money in good companies as an individual contributor, as you can as a VP or manager. Or like, the best paid people in many companies are now individual contributors at this point in history, especially in machine learning, like, at least in the, at the machine learning labs like OpenAI. But no other discipline really had that. You had to become a manager to progress in your career. And so I think one of the consequences was that when I really looked at it, like, hey, I need more great engineers. The best place to recruit them from was my own management team. And like, that seems silly. And especially because we, are there actually great managers? They're really well respected because they're good engineers.

• 31:42Speaker 01

  So maybe, but like, don't they want to code? Like, it's like, and, you know. So we created like this sort of mastery system, we call it, where, you know, every job has this ability to stay. You can get these, basically, level upgrades frequently and at any set of responsibilities you can, if you're. Insanely good at it, you can make lots of money. And like, that just seems like, of course you designed it like this. Why would you not?

• 32:12David Senra?

  Wait, so they can stay individual?

• 32:14Speaker 01

  Yeah, like, take an example, in engineering. If you're insane, like, if you're a hundred times better than the other people in this discipline, usually, you can make more money than a, than a vice president. Now, that depends on the value you can bring, but it is possible. And just like, I kind of hated the way we did like compensation in the industry, right? Like, again, these are boring topics.

• 32:36David Senra?

  No, it's not, they're not boring to me and to people listening. Wait, why do you hate the way that they were doing compensation in the industry?

• 32:43Speaker 01

  What I love about entrepreneurship is the, is the level of responsibility, personal responsibility people take. I said as much earlier when we talked about the founders who have been responsible for people's likelihoods. It changes you, it does, right? Like, so, like, I don't work myself well in an environment that's sort of like, everything is pre-described. I don't like joining other people's games and so on. All this kind of things are my biases. And again, you're implementing my biases here. So, in COVID, like, this is 2022, I think, or 21, suddenly Shopify went down 80% of stock value. I like, that's a, like, again, I didn't think that was a problem because, like, I think the stock market is basically like poly market, it's sort of a betting market on a future value, right?

• 33:26Speaker 01

  Like, it's not, like, you guys, then you guys are wrong, then you just bet at betting. Like, in fact, so, I work on the real market value of a company, which you guys are betting on, but I don't know. So, like, there's such a discrepancy from the way I see people talk about stock price and how I or have ever, or inside of companies is perceived.

• 33:48David Senra?

  But what was going on in your head when it dropped by 80%, though?

• 33:51Speaker 01

  Well, I'm like, well, my head, I'm relieved, because I'm like, you know, I, I mean, where the stock was.

• 33:59David Senra?

  Relieved?

• 33:59Speaker 01

  Yeah, of course, because.

• 34:01David Senra?

  What do you mean, of course? That's a normal reaction.

• 34:03Speaker 01

  I was like, I was not about to, like, raise money. I had enough money in a bank. I'm, you know, German, so like, I don't take that like much and so on. It's like, so.

• 34:12David Senra?

  Were the internal metrics strong? You felt they didn't deserve, you didn't deserve.

• 34:17Speaker 01

  Unit economics are amazing, however, like, at the.

• 34:21Speaker 01

  I don't, I don't wanna say this right, but I honestly don't remember the exact numbers. Like at the high point of our stock price, I think we were trading at beyond fifty X of revenue and stuff like this. I'm like, yeah, that's not exactly value investing here, right, like guys? And so I get it, like.

• 34:38David Senra?

  But you weren't worried about the fundamentals of the business?

• 34:40Speaker 01

  No, but like what, when it is fifty times revenue, I see it as my obligation to do that.

• 34:46David Senra?

  Okay.

• 34:46Speaker 01

  Right, like it's my, like my job, my, my job is to build the best company I can. The betting market says that I can deliver that kind of thing. And I'm like, yeah, maybe, but you go ahead, give me a moment here. Like, I, I need a moment here for, for doing this, right, like, so.

• 35:01David Senra?

  I, the reason I bring this up is because again, everything, I talked to another entrepreneur and I just run it through this, whatever the hell's in my head from all these books. And when I hear you talk about that, I think of that, the time when Amazon stock, he, Bezos talks about this in his shareholders. It went from like something like, you know, a hundred and eighty down to six or a hundred and twenty down to six. And he's like, yeah, but they were, they were focused on something else. I saw the actual fundamentals of the business and I was like, this thing's going to work. And so eventually, I think Buffett always repeats that thing where like in the short term, the stock market's a voting machine. In the long term, it's a weighing machine, you just wanna build a heavy ass company. And he's like, and, and Jeff's like, I'm building a very heavy company. Amazon will be a heavy company, so I'm not worried about this like short term drop by eighty or ninety percent.

• 35:42Speaker 01

  That really tracks. And so, but like one of the effects was, and this is right, like, but people got stock options at

• 35:49David Senra?

  Yeah.

• 35:49Speaker 01

  the level up there. And they rightfully say, well, how about it? But like, it's like, even if you say like, okay, well, I'm super game here to get us back there. Like this is gonna be, it's gonna take some doing. I realized the psychological problem with everyone being so underwater and having, you know, to spend years getting to basically the zero point where the stock options are worth like even a penny again. And of course they were like, well, but that's the company, like the company gave me those things at the time. It's like I received them, I was, I was, I was passive in this interaction. Therefore, the company has some kind of responsibility to kind of make me whole here.

• 36:30Speaker 01

  And I think that's actually, you know, I, I mean, I'd not necessarily see it this way because like.

• 36:37Speaker 01

  Like the risk was there and like these kind of things and like again, it's like other people voting, that's causing this price. I didn't set it. However, I do receive a point like they had no agency in the process. So we rebuild our compensation system to completely work for opposite of what everyone else does. We give people, here's your annual salary, here's an internal system, you go in, you look at it, this is the number. Now you get sliders, you can say, how much do you want in stock? How many do you want in RSUs? How much of this do you want in shop cash actually? And how much do you want in cash? And you can change it every quarter. It's like you decide like, like how much money you want. And you can even use a couple, like a tool that's there to lock in the value of the stock you receive

• 37:21Speaker 01

  for three years. Like it's like, again, sometimes orthodoxy can come back on the table if you get there from good principles. Like you can actually join Shopify and get exactly the same stock option deal that companies get at other places by using the tool we give you, but you have full agency and you make this choice. The consequence of this compensation system is kind of beautiful because what happens is first of all, it's too predictable. Second, you know, if you go stock and the stock appreciates and you hold them, you make more money. If like the stock goes down, you now get more stock options than in your next quarter. So it like it's rebalanced against the actual value every, every quarter. So it works really well. It's very popular. It's kind of hard to do because doing this worldwide for people

• 38:06Speaker 01

  in many different countries was like kind of a legal nightmare because like there's like all sorts of rules around how to change around changing salaries. We figured it all out. So we have a blueprint if our people want to do it, it works really well for us. But we're kind of proud of it because it's like, it's, it's, it's just like, again, it's a point of differentiation and we believe it works much better and. Again, I want people at the company to also feel like this is a company that is like never sleepwalks into anything, right? We kind of we are deliberate about things.

• 38:37David Senra?

  When you started this, I'm gonna do it my way, I'm working with the founder executive team, you were in the process of that and the stocks dropping?

• 38:44Speaker 01

  No, it was already there. Like that event, so that was a 2020, early 21 project, I think. And then I think, I think the stock market, when did that change? Like 21, late? So VCs are totally running together for me because it just was, I mean, there was no weekends, there was no everything else.

• 39:01David Senra?

  I can't tell, I can't remember who said this. I was talking to a much, I talked to a lot of older founders. I'm obsessed with like, people think I'm obsessed with old people. It's not that. It's like this guy's got 50 years as a, as an entrepreneur, experience as an entrepreneur. Turns out they know some shit. They've seen some shit.

• 39:14Speaker 01

  Surprise.

• 39:15David Senra?

  Yeah. And he's just like, man, you're gonna remember the beginning of your company. You're gonna remember the end and like so much in the middle is gonna, he said exactly what you said. It just like glitters together.

• 39:22Speaker 01

  Yeah.

• 39:22David Senra?

  So he's saying you should document it more.

• 39:24Speaker 01

  I totally agree. Lots of years are totally running together. I have reasonable record keeping on this. So I, and especially with all this AI-led agentic like reprocessing of nodes and press and so on, you can actually reconstruct these histories and timelines. And I'm fascinated with this right now, but.

• 39:44David Senra?

  So my understanding though, like you thought, you're now looking at running a company as like an engineering project?

• 39:51Speaker 01

  That's right. So I'm like, let's engineer a company, be a company engineer, as I've taught my team.

• 39:55David Senra?

  That applies for every single department and like, do you engineer marketing? Do you engineer everything?

• 40:00Speaker 01

  Everything. I require my executives to, I mean, at least tell me, but actually do it. Go to a podcast, some international conference and talk about how Shopify does the thing the conference is about differently and why that's better every year. If they don't have a good answer for how they are doing this right now, or how they would, that's, that's what I'm working on with them to crystallize that message. And there's a couple of reasons why I do it this particular way that we can get into that are partly psychological, but like it's also just.

• 40:33David Senra?

  No, let's get to now. What's the psychological?

• 40:34Speaker 01

  It's, I study the brain quite a bit and you know, the main conclusion you get to about the brain is really that the brain is a. Uh retrospective narrative alignment mechanism. Not uh it's it's actually terrible record keeping, but it it mostly attempts to uh take the most salient uh version of our self-identity and reconcile the history with it. And um it sort of rewards you for actions that are directly uh uh um congruent with with this identity and it uh dissuades you um from dissonance with your own identity. But you can actually like change your identity quite a bit and that actually makes this

• 41:19Speaker 01

  whole process work for you um significantly.

• 41:21David Senra?

  What do you mean by change your identity? Like the way you view yourself?

• 41:24Speaker 01

  Literally affirmations work, right? Like affirmations work, which is dumbest trick that uh that that works.

• 41:29David Senra?

  I'm so glad you're saying this because people from the outside like this guy's like very logical engineering.

• 41:32Speaker 01

  No, it's like.

• 41:33David Senra?

  And but you're all about intuition. Now you're talking about affirmations. You're speaking to the choir, just so you know.

• 41:37Speaker 01

  I'm a toolmaker. Like I always project very idealistic, but I'm actually not that idealistic. I'm super um I'm I'm like a craft person, toolmaker person. I I my entire life was making tools. I literally my pro my pro I chop as a tool. Um I make tools very often for toolmakers. I my my hobbies is making tools where engineers were people make tools, right? So like it's it's a fractal, like my my my life's a fractal of toolmaking. It's all about toolmaking uh uh aesthetics. It's all about the craft behind it, but also um also not because of craft for its own sake, although I appreciate that too. But even that's not for idealistic reasons because appreciating the craft behind the

• 42:17Speaker 01

  toolmaking happens to be pragmatically an excellent way to get really good at toolmaking. Everything is about outcomes.

• 42:24David Senra?

  What's the affirmation part, though?

• 42:25Speaker 01

  The affirmation that like you are if if you tell yourself or I will write down a hundred times something about yourself, um. That writes it into the neural frontal cortex at such a deep level that your brain will start reconciling you to that. It just works. I've used that very often to like I, you know, like I was terrified of public speaking until I just sat down for like a week and every day I spent like 10 minutes just writing that I like public speaking. I love public speaking.

• 42:56David Senra?

  You wrote that down?

• 42:57Speaker 01

  I know, yes.

• 42:58David Senra?

  And now you love it?

• 43:00Speaker 01

  Yeah, like a week later and I knew it's not this works when you know what you're doing, but like you don't even it's like it's not like a placebo. It's like it's actually like you just actively change your neural frontal cortex in this moment. So I use this often. I also write to myself, message in a bottle, this kind of things. That's all a different topic, but like it's so the point is like I.

• 43:23David Senra?

  What's the topic there? Hold on. You write messages to yourself?

• 43:26Speaker 01

  Yeah.

• 43:26David Senra?

  Affirmations or just?

• 43:27Speaker 01

  No, it's just like, like generally when I feel like something is like, hey, there's something I've figured out that I really like. I know I have to write a scheduled message to myself to remember it because like I need space to repetition on, on, on the idea.

• 43:43David Senra?

  What's an example of that?

• 43:45Speaker 01

  I mean, for instance, like we have a company keynote for like kind of thing, like a company get together summit once a year and for on to four week. And so usually I did a keynote there and like then I write a message in a bottle to myself of what was good about the process, what is bad about the process, what to do next differently and all the topics are left on cutting board just so like to get a head start. So that's a random example of that.

• 44:10David Senra?

  How did you learn this? That you could change identity, that affirmations work, that writing these things to yourself?

• 44:16Speaker 01

  I think trial and error, but like I think the hints are like everywhere, right? Like it's, I mean, affirmations are one of those things that like, I mean, there's a reason why we like society creates rituals, right? Because rituals end up being largely affirmations on, on, on repeat, right? So.

• 44:31David Senra?

  What do you think of visualization?

• 44:33Speaker 01

  Like so manifestation, these kind of things, I probably books too. You know what, the funny thing, I think everything works. If you just do it, the question is what's effective and quick.

• 44:44David Senra?

  It sounded to me before, like I started doing, reading all these biographies. I was like, this is some willy foo foo nonsense. And then you see very smart, analytical, logical, many case inventors and engineers. And it appears over and over again. People didn't know each other. They didn't, they worked in different industries, different times, lived in different parts of the planet. And they all talk about doing this.

• 45:05Speaker 01

  And it's parallel construction. They all come to the same conclusions in different words.

• 45:09David Senra?

  Yeah.

• 45:09Speaker 01

  And so, yeah, I'm, I'm, I'm personally, I mean, in the, in the self department, I'm extremely taking the historic philosophy, control what's under, what is under your control. Know what is, and then do the best possible job. It's the job is the thing, like, like the world project in life is just try to become very, very good at something. And ideally cultivate some significant skill, create potentially service products and then share them with as many people. Right, like you, you do this because that's what you're on platter for, right? Like, it's like, do things that matter in the world that are under your control.

• 45:51Speaker 01

  But also sign yourself up for, like, it's okay to sign yourself up for most interesting in places.

• 45:59Speaker 01

  As long as you remember what your job is in within them. So in this way, like I love the current times and I love the technology industry. I have a role inside of it, which is like, I'm taking care of millions of entrepreneurs in small businesses that, you know, are trying to use the word of technology, use word of retail through their own work then. That's actualize and that is a worthy goal and worthy job. And so like, you know, AI comes out and I'm like, people are like, well, should I start an AI lab or whatever? Or should I like, don't you want to, you know, work at OpenAI? And it's like, I mean, everything would be interesting, but you know what? What's really cool, pursuing the same problem in a changing landscape, right? Like now I get to reinvent everything I've already done.

• 46:45Speaker 01

  How fun is that, right? Because I really care about these problems. Anyway, back to the affirmations and sort of a brain, sort of self gymnastics. Going to my, my team and just saying, look, you know, just tell me what you will talk about on stage is bad. It's like afterwards.

• 47:03Speaker 01

  You need to internalize this as something that you have committed to me as imagining, I imagine that something that care about, they care about reconciling and so they have to do it, you know, because otherwise they, you know, said something untrue to me, right? And like they don't see themselves as someone who says untrue things and therefore, you know, you can actually make the reconciliation work for your own benefit in this, in this kind of way. It also just means like it emphasizes like difference, like difference is so important. It's so like autodoxy just really needs to be off the table from the beginning of a project or like from the beginning of decision making.

• 47:40David Senra?

  Have you ever studied James Dyson?

• 47:42Speaker 01

  Not enough.

• 47:43David Senra?

  If I could only recommend one book ever, it's his first autobiography, but one of the, he has a, he has a crazy line about this. So this is also very common with great entrepreneurs and you, you hit on other talks like, well, if you wanna, I'm trying to chase excellence, trying to be the best in the world or make the best tools possible, like therefore that demands difference, that, that path, that mission I'm on, I can't do it, literally can't be the best if it's the same.

• 48:03Speaker 01

  Yeah, right.

• 48:03David Senra?

  Like just think about this.

• 48:04Speaker 01

  Yeah.

• 48:04David Senra?

  And so like Edwin Land, who is Steve Jobs here, or the founder of Polaroid, he, he had a personal motto. He says, my personal motto is very personal and it may not work for you, but he says it is, don't do anything that somebody else can do. He just would not, he, I'm not making a me too product, but the reason I bring up Dyson, cause now he owns one of the most valuable privately held companies in the world, right? But he's writing that book when the business was fine, but he had one product in like one or two markets, it was doing like 300 million a year revenue, not a bad business, but a very small business compared to the size that it, it compounded to over the next like four decades or three decades. And he says in that book, even at that time, he's like differentiation and retention of total control. And he goes, it, he goes, you make it different, different even if it's worse.

• 48:45Speaker 01

  Yeah.

• 48:46David Senra?

  That's one of the craziest sentences I've ever read.

• 48:48Speaker 01

  I totally agree with that.

• 48:49David Senra?

  It has to be different even if it's worse.

• 48:50Speaker 01

  I completely agree. I see it all the time because again, it gets back into the copying of a painting problem. Like you can make a seven out of 10 solution to everything by copying the seven out of 10 that already out there in the market. But if you make from tabula rasa axions, your own version of it, you have mastery over, even if it's a six out of 10, you can iterate on this, you can take this past the seven afterwards, like very often, especially in technology.

• 49:21Speaker 01

  The world belongs to the fast, the people who iterate, the people who adjust, the people who understand what's costly and what's unnecessary and will prune away the rest. And I think actually we're probably, like pixel for pixel, the most inspiring picture that I think exists, that I've ever come across, is the SpaceX Raptor rocket evolution. Like, have you, do you know?

• 49:48David Senra?

  Yes, exactly. I use that as a, as a image for the Dyson episode I made.

• 49:54Speaker 01

  That's perfect. Exactly. It's perfect, right? Like, you, you, like, you look at this and say, yeah, that's, that's today's Picasso, right? Like, it's just like, this is, this is it. Like, this is, we're not in a point of time where the great works and the masterpieces are being done by one person. They are done by teams. Very few teams can move forward by subtraction. That is like, does not exist in industry usually, very, very, very rare. So it's, it's beautiful in that way. You have to do things different. You have to make them your own and you have to have mastery over the, over the first version if you want to take this far further. I mean, this is, we talked earlier about the podcast I do inside of a company called Context. And it's about that. It's like, what, how did we make the decision?

• 50:38Speaker 01

  It's like, everything around a decision is more interesting than a decision.

• 50:41David Senra?

  Is this podcast constantly updated? So it's internal, only for Spotify? God damn it, only for Shopify?

• 50:48Speaker 01

  I mean, especially when we talk about podcasts that make sense.

• 50:50David Senra?

  Well, they have, it's funny, I looked at my end of year rap on Spotify and one of the podcasts I listened to the most, which was shocking to me, was they have the internal company history. It's called Spotify, a Product Story. And it's because, you know, everybody else, I think, one of the reasons that we have a mutual friend, obviously, and Lulu, she's on your board, and the importance of telling your own story. Like, we went to dinner the other night and I was like, Lulu, what I love about you is like, you're repackaging old ideas. Like Napoleon told his old story, Julius Caesar told his own story. Like, they, all these people did it. It's a very valuable idea. And so everybody was trying to tell the company history outside of the company. You're like, no, you got all this other wrong. We're gonna make it ourselves.

• 51:32David Senra?

  And it's like, I think a 10-part podcast, but they, originally, I think they built it for themselves. And then they... Like publish it.

• 51:39Speaker 01

  I didn't know about this. I love this.

• 51:40David Senra?

  You should listen to it because it's narrated by Gustav, who was head of product, who's now co-CEO.

• 51:46Speaker 01

  Yeah.

• 51:47David Senra?

  And they take it in chronological order. And so like if like Sean Parker played a big role at the very beginning, right? He's obviously not there now, but he's on like episode one or two. And then they interview the people that made the decisions. And that's the whole point. Like we were making, they were all a crazy shift. They had to go from, you know, desktop to mobile, all the things that they deal with. Well, just go listen to what the company.

• 52:06Speaker 01

  Did at the time, yes.

• 52:07David Senra?

  Executives and founders.

• 52:07Speaker 01

  Totally right.

• 52:08David Senra?

  But not only what they did, why they did it.

• 52:10Speaker 01

  And the why is so much more interesting. Like one of the, like the turn of Toby said, it's real inside of Shopify, right? Like, it's like, people just throw these things around like, well, Toby said be doing it this way. Right? Like, and I, I just like try to get people to like, always ask when.

• 52:28David Senra?

  When I said, exactly. You change your mind all the time.

• 52:31Speaker 01

  Yeah. And this is not even, I learned about this because something is like really, really odd. And like really odd decisions, like there was easier ways available. Like, how did we get to there? It's like, wow, it's like everyone said, but you wanted it this way. It's like, I'm like, under which context? When did I say this? Like clearly we've never talked about this. So it's like, it's very common thing. So.

• 52:53David Senra?

  What's a typical episode? Is this you explaining your thinking of what's going on currently in the company?

• 52:56Speaker 01

  Yeah. Yeah. It's like taking people back to major decisions.

• 52:59David Senra?

  Are these short episodes?

• 53:01Speaker 01

  No, like initially it went through phases. There was a sort of four, the first maybe 50 episodes we said, like we had a, we have to mix it down to 23 minutes because we calculated that that was the average commute in Shopify. Like, so we checked where everyone lived compared to offices, ran the data and it was 23 minutes. And so we made it 23 minutes because that seemed like as good, like we needed a reason.

• 53:29David Senra?

  And you like designing your constraints. You talk about this a lot.

• 53:31Speaker 01

  Exactly. So, so, you know, just like, well, I also just don't like picking 20 minutes because it sounds good. Like I want, like I need a better reason. So I, I, I might say I want something to be like 20 minutes. Sounds right, but let's find an actual good reason why it's 20 minutes. And then we found 23 minute reason. So sometimes you're allowed to like just parallel construct the thing you want to do anyway. Then at some point we abandoned it because just like, you know, the nice thing with podcasts is like people can skip move. It doesn't matter, like you can just keep going for hours and hours and. Do you have any ones that are like long? I think there's one which we had to cut over a couple of episodes that ran like, I mean, if you run it four to five hours, it's like. What was that one about?

• 54:15Speaker 01

  That was like the philosophy of engineering with a bunch of our distinguished engineers, like, like how, you know, it like it's, you would not believe how immature engineering is as a discipline. It's just like, um, there's so many good ideas and so many bad ideas. And it's so hard for people to sort through them in a, in a way that's like way harder than any other industry. Cause it has a weird property, like software has a weird property. Um, I mean, the best thing and why the business model of software is so insane is because of zero marginal copying of software is free, right? Like, it's like you can, you know, we build Shopify, first person signs up, we make money, second person signs up, uses exactly the same thing.

• 54:57Speaker 01

  And it's like, um, you know, the second instance of it is not, it's the same piece of software. So, um, hence the margins of software are incredible. The same thing causes a lot of problems for the creation of software because you just don't know how much dead weight is in the system. If you compare this with, um, electrical engineering, there's a very clear cost of manufacturing, right? Like the, the bill of materials is like the thing that dominates the success of a product because it dominates when the costs, it then dominates the product market fit.

• 55:28Speaker 01

  It also, manufacturability is a huge component in electrical engineering. It's like, is the board laid out in such a way that it's prone to defects? Did you choose all the right components? I mean, like, it's like one chip get really hot next to a soldering thing, but like, you know, I remember the original Xbox, it sorted itself. If you just played certain games too long. So, you know, there's real constraints like this, so excellence is obvious in a way. It, it's like in the numbers and everything, everyone's trained on costing waste into the system. Software engineering just is, throws away so much of a capability of these incredibly powerful machines.

• 56:07Speaker 01

  Partly because it just doesn't cost anything. However, at a certain scale, it starts costing, but at this point, it's being fixed by operations teams, getting more servers, rather than engineering teams going back to fixing those things. So the, um, consequences of.

• 56:25Speaker 01

  Bad decisions in software engineering are an externality that doesn't accrue back to the engineers who caused it in almost all instances. So it's like a little bit like a factory is polluting the environment. It's just like it doesn't cost back to them. And so anyway, so therefore it's a very tricky industry to move forward. It actually quite often moves backwards significantly. Computers got much faster and we threw a huge amount of capital away making like these very, very heavy client-side JavaScript applications that took over everything. We were just god awfully slow and very error prone and took forever to load, especially in e-commerce where people visit sites rarely.

• 57:09Speaker 01

  Some of our customers went out of business because they got talked, they talked themselves into their own stack. They hired a CTO, brought in their own team. They used a set of technologies that they wanted to use because they are currently within thing that has the most interesting conferences and the most interesting places. Then they deploy it and you know, like it sort of works in the demos, but the problem is when you're going to website for the first time, you have to load it all and you don't have an up-to-date MacBook, perfect hardware with much memory like everyone has who spoke on engineering teams. You might have an Android device and you might be on a train right now, you're sitting there a minute and a half for this thing, for this online store to load. Guess what the conversion rate of that online store is?

• 57:52David Senra?

  Zero.

• 57:53Speaker 01

  Yeah. I'm quite annoyed by this, although we are, that was a real, real, real, real problem in 2023 especially when like I think a bunch of frankly as you know, older engineers had to like take the kids to the site and just like have a good conversation.

• 58:11David Senra?

  And that was the, that was the context of the episode of context.

• 58:14Speaker 01

  At least that's what led to this particular thing. I don't know if we actually succeeded there, but like I think we didn't need to because I think, like I think we will just change. Like moment zero, zero interest rate phenomena, they're, they're, they're gone.

• 58:29Speaker 01

  People actually wrote better quote out of sudden. Like it's like amazing how much like how consequential like the zero interest rate, absence of zero percent interest rates actually ended up being, you could feel it. The engineering team being less prone to accepting random waste into best acts. It's unbelievable.

• 58:48David Senra?

  That's interesting. I don't know if I've heard anybody else make that point. I think this idea of hearing directly from the founder in an audio way.

• 58:55Speaker 01

  Yeah.

• 58:55David Senra?

  Is underutilized.

• 58:57Speaker 01

  Totally.

• 58:57David Senra?

  I did this episode on the founder of Kinkos. He was dyslexic. Okay.

• 59:00Speaker 01

  Yeah.

• 59:01David Senra?

  So.

• 59:01Speaker 01

  So am I.

• 59:02David Senra?

  Yeah, I heard, which surprised me. So he, actually, a lot of great founders are dyslexics.

• 59:07Speaker 01

  It's very common.

• 59:08David Senra?

  Yeah, it's very common. So it shouldn't surprise me. So he's like, I can't read your goddamn email. And I'm not, he was also, I think he said he had like ADHD, so he couldn't sit down at a desk. So he, his job was like, what I like to do best. And he's like, I just go around and all the Kinkos at the time were owned by individual people. Like, so it wasn't like one cohesive corporate structure. And so therefore, there's a lot of experimentation going around. So he would just travel the country and then he'd spend all his days in the stores. And he'd be finding, because of all these people during different trial and error, good ideas.

• 59:36Speaker 01

  Yeah.

• 59:37David Senra?

  And so what he would do, this is back in the day, he would call into a corporate voicemail. And so he, at the end of the day, he'd give like a three minute update about all the good ideas that he saw. And then you'd come in as a Kinko employee the next morning and you could play Paul's voicemail.

• 59:52Speaker 01

  Love it.

• 59:52David Senra?

  And then he, this was an interesting thing that you might agree with, though. They, after doing this while, he's like, you're resurfacing all these great ideas, right? This guy in Memphis found the best way to do X.

• 1:00:04Speaker 01

  Yeah.

• 1:00:04David Senra?

  Why don't you mandate that everybody in the company does X this guy's way? He goes, because if I do that, that's the best way it will ever be. Which kind of relates to what you just said. He's like, listen, there's a probably 100 different good ideas or right ideas.

• 1:00:18Speaker 01

  Yeah.

• 1:00:18David Senra?

  And if I stop here and don't keep tinkering, going right to that word that you like, then that's the best it will ever be.

• 1:00:23Speaker 01

  If you need something, you tell people what to do, you might get it or you probably will get it. If you don't tell them what to do, you might get something you cannot possibly imagine if you have good people. And so this is like actually a really, really important thing. It's much more important to create the environment in which people can be their most excellent self than it is to prescribe, here's the precise moves to do.

• 1:00:49David Senra?

  So how do you create an environment? That people can be the best version, the excellent version of themselves. I heard you say, is this related to your idea where you're like, you said something that made me chuckle. You're like, I don't do corporate baby-proofing.

• 1:01:00Speaker 01

  Yeah, exactly. Like, I mean, exactly. Absolutely. It's the same idea. Like, the baby-proofing thing is real. Like, what's, what is internal policies, right? Like, processes, what are they? They are like, do this thing different from the way your intuition tells you to. Okay, why are you wanting people to behave differently from their intuition?

• 1:01:22Speaker 01

  Like, let's, let's look at our higher order bits there. It's like,

• 1:01:26Speaker 01

  like, what other opportunities do you have? Well, you could change the environment such a way that doing the right thing is intuitive. Right? That's, that's pretty good, because now you don't have to post a policy. You could also, you know, hire people whose intuition is better honed. Very often, policies and processes are sort of downside protection. You're trying very hard to make,

• 1:01:50Speaker 01

  to, to avoid the people who do things wrong to be of, you know, causing so much damage. That's like, like, in downside protection, but you're also really limiting what the best people can do, right? So I think in creating, like, an environment almost as a box for people, like, here's the space, and I want you to fall, like, inside of the space is this problem I need you to solve. Right now, my world, in commerce world, is attempting to figure out what agenty commerce is, how it works, how the, all the companies are working together, like, how, yeah, the research labs work with everyone else, how to expose product catalogs from entrepreneurs, how to make sure that transactions can be met,

• 1:02:34Speaker 01

  what the large language models need in terms of information to, you know, do a fantastic job as a, when, when people ask them to be their personal shoppers.

• 1:02:46Speaker 01

  You know, that's a box. Like, inside of it, somewhere, somewhere in it, it's all dark, is the most beautiful solution.

• 1:02:54Speaker 01

  What tools do we have to explore this box? It's like, Doug, like, I don't know. I can take a stab at it. I can paint a picture of what I think is good. But that's just like sending people into the room with a couple of tools. Afterwards, they need to make their own decisions and I want them to do this. Like, I'm not there. I don't wanna like control every decision. The company makes millions of decisions every day, right? Like in a building like this, right? But when I can make a decision of like this, like had them really want to be on this journey, had them fallen in love with a problem and see the potential. And I can make sure it's the right team and everyone has the right skills. And I can make sure that, um, that they know what they have decision power over.

• 1:03:34Speaker 01

  And like how to, um, at some point, uh, because, you know, people are only willing to take so much risk. How to transfer that risk to, to me ideally, uh, or to company, right? In the form of our projects work in phases, a prototype phase is what I just described, where you explore the problem.

• 1:03:59Speaker 01

  Then you think of, like, when you've learned what you need to learn and think you have something that you can, uh, build. You make a proposal and you transition out of the prototyping phase. That's a meeting, right? Like, that's a, you know, that's what we call, like, it's a phase transition in our, in our project system. Their software that manages all this kind of thing. They can use AI to preview what the, what the, um, uh, transition will like be like, because it's trained on all the other reviews I've ever done. So they can sort of mock do it and figure out what I will probably say. That saves me a lot of time. And then we have an actual, um, uh, meeting.

• 1:04:40Speaker 01

  And, um, you know, then they tell me what they're planning to do, what they've learned. That helps me a lot. And then I say, okay, uh, okay to transition. There's some engineering leads, design leads give okay one. I give okay two, um, and then they are in a build phase and then a new phase starts. That's a new box. They, they have a agency to make decisions in there. At this point, I assume the risk. This is, it's like a trade of, um,

• 1:05:10Speaker 01

  Accountability for autonomy. And so that's how we found we can almost rationalize this system. Because what I'm finding is like, I mean, all the biographies you read, what you find is, I'm sure, is that the moment of insight, often the product that made, that started all, or the artworks that are defining the careers, they were not really coming out of an office building environment, right? Where someone had OKRs that offered precise metric to hit. And then like Da Vinci probably did not have one Vesuvian man as an OKR given to him, right?

• 1:05:54Speaker 01

  Like, it's like you kind of have to create like a box for them, sometimes a physical space as well. Like he was in an attic that just ended up being where he did most of his creative work, I believe. And so you try to figure out what is this sort of environment in which where excellence and creativity can come together? And then collapse it to saying, okay, now the company needs what it needs because we need to make resource allocation decisions. I mean, more people onto a project at this point, there's a couple of sort of things that need to be decided. And then autonomy is regained until the next phase is releasing, at which point we do that review.

• 1:06:36Speaker 01

  And sometimes we say, okay, we're not ready to transition because we need, things need to be differently. But that's the way Shopify orchestrates now. These are all things that exist today, based on the days during COVID where I reviewed every project and couldn't. And like, well, what should I be able to do if I would be like, if I would be a competent CEO, what would I have put in place so I could do this thing I need to do here in the beginning of COVID very, very quickly? Given that I wasn't, and now I aspire to be, what needs to be created? And so like, whatever the answer to that is, we worked hard on it. And I think we just discovered some extraordinarily powerful systems, mechanisms in this journey.

• 1:07:20David Senra?

  That was the prompt, like what would a competent CEO do in this situation?

• 1:07:23Speaker 01

  I love to take the view that like I'm a corporate raider.

• 1:07:29Speaker 01

  And Shopify went bankrupt and I bought it on a fire sale and I'm like marching in on day one here and previous management was crazy and we need to turn this place around, right? Like that's my favorite. Like I love playing this game every like year, figure out what I would do differently and then like it's like, let's go. I have my to do this. And I asked a lot of teams to do this a lot. Like it's like when we have systems that just don't work. One of the most powerful, you know, maybe through affirmations, maybe for experience, things you can do is just don't be prideful about the prior work too much. It's allowed, you're allowed to have pride in it, but like you want to wake up better every day, right? You want tomorrow's version to be better than today. And for

• 1:08:14Speaker 01

  that, you have to kind of downgrade what's there. Like you can't, like the sunk cost fallacy is so powerful.

• 1:08:22David Senra?

  But how's that an affirmation? Like, how does that represent? Like, how do you, when you're actually talking to yourself or you're writing this down, or is this in your monologue?

• 1:08:29Speaker 01

  I literally write hit pieces on the past, right? It's just like.

• 1:08:34David Senra?

  A hit piece?

• 1:08:34Speaker 01

  Yeah, like I just like all the things that are wrong with the thing, I somehow am really proud of.

• 1:08:38David Senra?

  You are so much like some of my favorite founders, Dyson's like this. My friend Kareem, who's one of my closest friends, he's the co-founder and CTO of Ramp. It's like nothing's ever good. The way I describe him is just like, no resting on laurels, no sleeping on winds, do something great and then do it again. Steve Jobs said this. He's just like, well, what's the proper response when you make something wonderful? He's like, you do it again.

• 1:08:59Speaker 01

  Yeah, let's go.

• 1:09:00David Senra?

  And no, a lot of these, a lot of these great people, they don't really have rear view mirrors. Like they know, obviously learn from what they did, but they're not like, wow, look, look at my trophy room. They don't think that way.

• 1:09:10Speaker 01

  Look, nostalgia was put on death certificates in the 1800s, right? Like it's like it's people died of nostalgia in their minds. I mean, they really died of something else.

• 1:09:19David Senra?

  But like, I've never heard that before.

• 1:09:21Speaker 01

  It's like, we used to know that nostalgia is not a good thing. It's like it was, it was bad indulgences. Now it's barely of eyes. So I think nostalgia needs a little bit more

• 1:09:35Speaker 01

  scrutiny. Overcoming sunk cost fallacy is one of those things that. Like any path that you can take to get there is going to be enormously beneficial.

• 1:09:44David Senra?

  Well, I think playing the game of corporate raiders is a great way to do it.

• 1:09:46Speaker 01

  Exactly. So when you develop tools.

• 1:09:48David Senra?

  You kind of separate yourself because that was your decision. You might be like, oh, well, like I feel a little sensitive about that. It's like, no, no, that was somebody else's. This is a new company now.

• 1:09:57Speaker 01

  So one of the things that is unpopular when I do it inside of a company is like, I really shit talk the past, especially if I did it. You know, like, you know, there's still like systems that I build inside of a system. So I like, I.

• 1:10:10David Senra?

  You shit talk the past publicly?

• 1:10:12Speaker 01

  Yeah, I trash. Like, I make fun of all the ways, and this is hilariously wrong in funny ways. And I, I need to remind myself, especially when I do a certain area I didn't look on, that like I got to have to proviso it or like I have, I need these like corporate radar, like I'm collecting these now.

• 1:10:34David Senra?

  It's almost like dissing yourself.

• 1:10:35Speaker 01

  I need to help people not think that what I'm doing is I'm passing judgment on their prior work because I'm not. We are all to like expect everyone.

• 1:10:44David Senra?

  You are passing judgment on the prior work. You're not passing judgment on them as a person. This is what Rick Rubin talks about in his book all the time.

• 1:10:49Speaker 01

  But it's not theirs anymore once it's out there, right? Like this is the thing.

• 1:10:52David Senra?

  Ooh, say more about that.

• 1:10:53Speaker 01

  They need to disconnect from like the work is collected is the moment the pull request is accepted or the okay two is accepted. You've converted like your craft into something the company is like, it's in a company's commons. It's a company is a collaborative project where everyone contributes. And there's a process by which it's contributed, at which point the company accepts it as being on quality and says like, this is now part of, you know, like my like company's embodiment essentially. So the product, you've contributed it, you can, you deserve the credit for this and so on.

• 1:11:36Speaker 01

  But the company could have had someone improve it at any point of time, right? It's not yours. It's like, we don't allow people to use word ownership over parts of a codebase or so. We only allow stewardship as a work, like just as a, as a proxy term, because sometimes you need to be able to talk about it. In this way, Shopify thinks of it as more like an open source project, you contributing into the comments. People talk about Wikipedia, not about the particular editor of a Wikipedia page. You know what I'm saying?

• 1:12:06David Senra?

  I have a selfish question before you move on.

• 1:12:08Speaker 01

  Yeah.

• 1:12:08David Senra?

  So you're looking at all past work. You have, there's this guy named David Ogilvie, who is one of the greatest advertising agency founders. And he says that we have a divine discontent with our work.

• 1:12:17Speaker 01

  I love that.

• 1:12:17David Senra?

  It's a perfect anecdote to smugness.

• 1:12:19Speaker 01

  Yeah.

• 1:12:19David Senra?

  Right? Because he's like, you don't want to rest on your laurels.

• 1:12:21Speaker 01

  Yeah.

• 1:12:22David Senra?

  I talked to James Dyson about this, though, because he has a very interesting organizing principle. So we're going to take this cup right here. This is a product. He goes, this is, he organized this entire life. He's been an inventor and engineer for 55 years now. And he's just like, I see this product and I say, ask myself, how can this product be better?

• 1:12:38Speaker 01

  Yeah.

• 1:12:38David Senra?

  Then I make it better. And then I put it down. And then I, short time after, pick it back up. How can this product be better? I make it better, put it back down. And he goes, I just, he goes, I see the bad in everything.

• 1:12:50Speaker 01

  Yes.

• 1:12:50David Senra?

  But the interesting part is he's intellectually and emotionally mature enough. He goes, you have to understand, it doesn't, like, I'm not a miserable person.

• 1:12:57Speaker 01

  Yeah.

• 1:12:57David Senra?

  I just look at it as like, this is a problem, that problem's an opportunity, and I want to work on that. What is your inner monologue when you're critiquing your past work? Are you harsh and excited?

• 1:13:06Speaker 01

  Yeah, no, no.

• 1:13:07David Senra?

  Oh, you get excited?

• 1:13:07Speaker 01

  I get excited by, by, by finding problems. Like, I just like, I love, like, I mean, look, at this point, I'm such a, I'm such a long-term veteran of, of tech company building. I love figuring out what we're bad at stuff. Because like, we have a very good thing going on. Like, by all intents and purposes, this thing's working, right? So, and, you know, when, when I figure out what, like, we're actually bad at something, I'm like, holy shit. Like, I have an obvious blueprint for now, how to become a better company now, which is like, actually my job, my craft, right? Like, this is all opportunities. Things go into comments, they are being, hopefully judged by everyone. I get grumpy when things that are shitty are not identified as such and improved. And then I make people go do it. And sometimes I do it by trying to create.

• 1:13:55Speaker 01

  Energy by just like roasting the things current state about just like I want I want people to feel no deference to it. I don't want people to respect the piece of code that exists and that or system that I want them to improve. And I want people to, you know, just find their sort of energy source because I what I'm asking them is like go into a particular box that contains this problem and do the best possibly better than anything I could possibly ask you right now for solving it. Because I expect people to be highly agentic and, you know, fond of problems and just like find better solutions than what, you know, industry usually produces and so on, right? That's the entire point. It's unpopular when people aren't in the right headspace for it and it's incredibly effective if

• 1:14:40Speaker 01

  they are. So the difference very often is just a couple of words and a bit of framing. And I just find that's like, that's one of the most powerful sort of tools you pick up, I think, along, you know, along the journey. It's like the five words to say at the beginning of a sentence would change everything. My co-founder actually gave me one of those very early, which was like probably why I tuned into this kind of thinking and this collecting these kind of things because

• 1:15:08David Senra?

  Wait, what did you mean by the five words you say at the beginning of a sentence?

• 1:15:12Speaker 01

  I used to go, I got an engineer, that's always like an interesting experience of four other engineers working for me. And like, I stay pretty current with engineering. I still do not a ton of production, production engineering, but like I do, I sometimes start new projects with people like, and the first 2030 progress or commits in many repositories for things that we use come from me. So like, I like doing this. It's, it's part fun, part, I sometimes need to tap into my craft. Anyway, so that's a surprising thing for people, of

• 1:15:56Speaker 01

  course. So my intuition was always like, okay, well, this is not the right architecture for this kind of thing. And I know this for a fact because I've built this thing before. So let me go to a right whiteboard and just like re-architect this. And like, and so at some point, and that like now

• 1:16:16Speaker 01

  You know, Daniel, my co-founder, like, explained to me, "Well, look, you get people pretty defensive then because they just came to show you basically, you know, what was objectively their best work because you presented it to you and that matters to them. So and then you just, like, it doesn't matter if you go and make a much better system here out of the top of the hat. They are like, if I truly ever did this,

• 1:16:42Speaker 01

  they're gonna be defensive and try to save face. So

• 1:16:46Speaker 01

  just put, for example, in front of every sentence. And so I'm like, what do you mean? And now, like, I tried this and it works perfectly. So instead of just telling them, "Hey, you know, instead of doing this, like, here's the

• 1:16:58Speaker 01

  architecture that you should use," just say, like, "I could think of doing this a couple of other ways. Maybe it's something you wanna consider. For example, what about this?" And then just do it. Now you're on the same side. You know, you're on a team. We all work together on the same problem. I'm just, I'm adding input. Now, like, everything is the same. It's five words or so in the beginning. I just find the magic of these five words. It's, or not this specifically, it's like things like this, like just frame things slightly different and life's easier.

• 1:17:32David Senra?

  I read something Jeff Bezos said that changed my perspective on the importance of high-quality sleep. He said that he makes sure he gets eight hours of sleep a night. And as a result, his mood, his energy, and his decision-making is improved. His point was that you get paid to make high-quality decisions and you can't do that if you're sleeping terribly. And the product that has made the biggest impact on my quality of sleep for years is Eight Sleep. I'm lucky enough to be friends with the founder of Eight Sleep, Mateo, and we live in the same city. A few months after I started using Eight Sleep, I randomly ran into Mateo at a restaurant and I was with some friends. So I go over and say, "Hi." When I got back to my table, my friend asked me, "Who was I talking to?" And I said, "That's Mateo, the founder of Eight Sleep." And my friend replied, "He looks like he gets good sleep."

• 1:18:15David Senra?

  Mateo is living and breathing his product. I had never had the ability to change the temperature of my bed before I had an Eight Sleep. I had no idea how much that would improve. Move the quality of my sleep. I keep my 8Sleep ice cold. It's cold before I get into bed. So I fall asleep faster and wake up less during the night. That feature alone is worth 10 times the price. There are very few no brainer investments in life, and I believe 8Sleep is one of them. That is why elite founders like Mark Zuckerberg and Elon Musk have all said publicly that they use 8Sleep. I would recommend getting the Pod 5, which is the newest generation of their signature product. It is a smart mattress cover that you place on top of your existing mattress, and it is next level sleep tech. It automatically regulates your body temperature

• 1:18:59David Senra?

  throughout the night independently for each side of the bed. The result is you get up to a full hour of additional quality sleep per night. Make the no brainer investment in your sleep by going to 8sleep.com/cenra and use the code CENRA to get $350 off. You can try it for 30 days at home and return it if you don't like it, but I'm confident you will love it. I will never let anyone take my 8Sleep from me. Make sure you get yours at 8sleep.com/cenra. One of the things that Daniel from Spotify, I almost said Shopify now for him. David from Spotify told me.

• 1:19:33Speaker 01

  We'll only be fair.

• 1:19:34David Senra?

  He's like, you should ask him, like, what were some of the advantages of starting with Silicon Valley?

• 1:19:38Speaker 01

  I think there's just too much cross pollination. You kind of have to sync the companies towards like, entropy creates equilibrium. And so you end up like with the companies just being very recognizably similar to each other. And the activation energy for being very different is super high because that means people come with the wrong ideas into your company, behave incorrectly, and you have to like tell them to behave differently. Where if you're outside of a place like Silicon Valley where people just move along between companies. I mean, first of all, especially early, I traveled to Silicon Valley a few times a year, but I tried to just take it all in and learn as much as I could.

• 1:20:21Speaker 01

  But of course, what I got from everyone was not actually the answers to my questions about how to do things. I was getting the aspirations usually, or the highlight reel. People wanted to seem smart, right? Like, and so they gave me the best version of what they think the answer should be, or what their company ought to be doing. And so, which is great, because then I took that back home with me, free flights, and and sort of took the ideas that are relevant, tried to always put like a Shopify spin on it. Like, I don't like taking ideas, as you clearly can tell and never did. Sort of like, just like, figure out how to localize them to our problems, and ideally try to do something better.

• 1:21:06Speaker 01

  And so, only very many years later, I did realize, I was always, like, always for my career, was comparing my and our average to everyone else's aspirations and highlight reel. And just like, that alone is a really, really good thing, and if you then try to do better than that, you know, sometimes like, just ignorance is an incredible way of actually just doing better. And so, that helps, the process of having to translate, being able to translate things. Like, we had no one, like, when Shopify IPO'd, we had one member of executive team who ever worked for a public company, that's it. Wow. We had no one who took a company public. We had no one who was an executive at a public company.

• 1:21:51Speaker 01

  We had one executive who worked at a public company once. And it's just like, I think that's cool, right? Like, it's like, that's, I've had a real sense of accomplishment about that, because like, it meant we could, we became our own thing. Our entire motto, becoming a public company, was, we are not going public, we are creating a public version of Shopify. And so, that was like... What's the difference between that, between those two substances? Again, becoming something else, it's like, we don't want to, like, a lot of people avoid, when they're a public company, we're gonna be different, because like, people sort of expect public companies to be a certain way, at least for people who worked at Shopify did. I felt it was important to be different and do things differently.

• 1:22:34Speaker 01

  One thing we did, you will appreciate this, is... You know, we looked at the requirements. We talked about Formula One. Formula One is fun. Sorry, it's a little bit of a via. But like Formula One, I love because it's like there's a rulebook. It's the opposite of every other rulebook on planet Earth. People read it so that they can comply. The Formula One rulebook is a rulebook that is read so that you figure out how to beat it. Right? Like, and like, it's, it's like, it, there's no engineer in Formula One has anything to do with, with central casting engineers. Central casting engineers actually usually want to get requirements and then comply to them. They're like the people going to Formula One are the people who want to beat the system. Right? Like, this is very important to them.

• 1:23:15Speaker 01

  So I, I, I, I count myself as of the archetype of the ladder, like, like a group of, like, I, I, I would have liked being an engineer in Formula One. I, I like beating the systems, but I'm, but I'm, that other people tell me to abide by.

• 1:23:28David Senra?

  I heard a story one time that somebody had hacked your compensation system to get more money than, you know, essentially, they just studied the rulebook, found this loophole, and you're like, good for that person. Like, and then you'll fix the loophole or whatever the case is, but like, that's exactly the kind of person I want working for me.

• 1:23:43Speaker 01

  Exactly. I mean, yeah, especially if it's, I mean, there, there's a way, I mean, what happens next ends up mattering, right? Like, so, okay, this goes on.

• 1:23:53Speaker 01

  Like, at some point, this becomes, well, you're just exploiting a weakness fully. I, I mean, I don't want to give too many provisos, but generally, like, people who are like, looking around to figure out, like, I, I never begrudge anyone being an intelligent actor in a local incentive system. That is just like, everyone's allowed. That's pretty much my morality at this point. Like, it's like, or, or at least a big part of it. You're allowed to do this.

• 1:24:20Speaker 01

  I own the incentive system. It's not, you get too much out of incentive system, or it, it, incentive system tells you to behave in a way that is not congruent with the company, the company's goals. That is my skills issue in designing a compensation, not, not, not, not your job.

• 1:24:37David Senra?

  Not their fault for taking advantage of it.

• 1:24:38Speaker 01

  But really appreciate if you give me a heads up. Like, so, because we are still the same team here, so like, you know, maybe you raise your hand at some point saying this is fine.

• 1:24:47David Senra?

  Yeah, not like 10 years later, after, you know.

• 1:24:49Speaker 01

  So, back to the IPO, just like, and the IPO, we, we, we just looked for ways how to, like, within the, they constrained rules by the SEC, where we, do we have agency, where we can do different things? We sort of honed in on the IPO roadshow video, like, It's like a horrible video player, the IPO roadshow website. It's like, and every other IPO we could find was this, you know, CEO standing in front of a screen camcorder and just sort of going through the same slides. You're like, there's no rule for that. Let's shoot a fucking documentary here. Like, let's go through the history of why this company exists and why it's important.

• 1:25:31Speaker 01

  And he said, like, what video can be put onto this space where no one expects it? That will somehow hook people in to fullscreen the video within the first 20 seconds and actually watch the entire thing. And we heard so much about this on the road, like so many people were like, I always look forward to meeting you. What you guys did with this video was insane. I didn't even know you could do this. Every video, every IPO after this was like our way. So it was like a nice little moment of putting a bit of like agency into process, which was pretty.

• 1:26:00David Senra?

  I heard this story one time, I think it was like the founder of Sirius XM. I forgot who the person is, but they were like, well, how do you make annual reports? And there's like no rules around there. So you have to present certain information. So they made a book and like the book would be illustrated and she's like, no one said we couldn't do it. It's like, we're just going to do it our own way. Let me ask you a question though, because I think I heard you say this as well. You were getting what you felt was bad advice or incomplete advice, or maybe advice not from first principles about like whether to go public or not. Some people were saying stay private longer.

• 1:26:34Speaker 01

  Yeah, yeah, I get you. The advice was always like, don't, right? Like, it's like.

• 1:26:38David Senra?

  Who was telling you this, other founders?

• 1:26:39Speaker 01

  Yeah, founders, Silicon Valley, orthodoxy definitely is to avoid it. And I don't know, I can tell you the story of how my decision, but like, it's just like, basically it's like, I mean, I suppose I'm predisposed also when everyone agrees with something to. Take the counterfactual, just hold it up to see if I potentially like it better.

• 1:27:01David Senra?

  Just a personality, embedded personality trait.

• 1:27:03Speaker 01

  I just like, I find Plan B usually is a better one.

• 1:27:07Speaker 01

  Everyone puts Plan B, like, if, if, if, I think for many, many, many people on planet Earth, always doing their Plan B would lead to a better experience, right? It's just like, like Plan B gets the ambitious one, the, the, if this event happens in my life, fuck it, I'm just gonna build a company. It's like such a common Plan B.

• 1:27:26David Senra?

  That might be what you actually want, but you're lying to yourself or you're scared or whatever.

• 1:27:30Speaker 01

  Yeah, and also, again, you are a human being, therefore you have, you come, your firmware comes preloaded with a problem called the sunk cost fallacy. We just do, right? It's like this, you gotta operate that out of yourself a little bit. You gotta be able to, like, discount what has happened more to make good choices. Because otherwise you just chase bad with good money all the time, or chase bad plan with your hours in the day.

• 1:28:00David Senra?

  Yeah, I think humans are flexibly scared of change too. They'd rather be in a bored, boring, or like even miserable environment than actually change because the fear of change is so great. So wait, so people are telling you, stay private longer.

• 1:28:13Speaker 01

  Like, being private is better. Like, friends of mine, like, at Stripe are running this experiment. Like, they managed, what they put off in terms of figuring out how to stay private for such a long time is actually remarkable. I just think they spend a lot of time figuring out how to stay private. And like, I don't think that's the most valuable way to spend time, right? Like, it's like, I think you can-

• 1:28:36David Senra?

  Well, so you went public 2015?

• 1:28:38Speaker 01

  Fifty, yeah.

• 1:28:38David Senra?

  What were the arguments for staying private longer in 2013, 2014, when you were having these discussions?

• 1:28:43Speaker 01

  We were tiny. We had 800 people, a Canadian.

• 1:28:49David Senra?

  So they're saying you're too small?

• 1:28:50Speaker 01

  Yeah, like, I mean, Shopify is- First trades happened at, I think, a billion, 1.5 billion dollar valuation, right? Like, so.

• 1:28:59David Senra?

  It's pretty wild that, you know, the public market almost got like venture, could have got venture. If you bought Shopify.

• 1:29:05Speaker 01

  Yes.

• 1:29:05David Senra?

  You essentially had venture returns in the public market.

• 1:29:08Speaker 01

  Every once in a while, someone puts together a list of best stock market returns over the last 10 years of whatever. And like, yeah, like I own that list, right? Like, just because I decided to take Shopify, like I did the old school thing. That was normal. That's what everyone did. That's what people, people went public fast. And by the way, this is kind of important. Like, you know, public market needs to have growth because where else is prosperity coming from for people? For people who don't have, like, these obvious accretive investors, accredited investor laws and stuff like this. All they do is like make it so that, like, like when you're rich, you can invest in private company stock.

• 1:29:50David Senra?

  Yeah.

• 1:29:50Speaker 01

  And when you're not, you can't. And well, where are the returns? Like, of course, this is such a fucking conspiracy to keep everyone private because they're just like sequesters of the growth exposure to institutional and investors and people who are already accredited. And so I just, I just really dislike that whole thing. I think, like, man, like, again, it's, it's about building things and sharing what you've figured out. And like, people buying a ticket to ride the Shopify because they like what they're building is like,

• 1:30:24Speaker 01

  please, like, that's clearly what we want. So, so I just think the institution of public companies is good. I mean, my beef is with the whole notion of like influence over companies. Again, path dependence, like one vote, once, like a one, one stop, one vote is like, yeah, but like. No, like everyone who studies like decision making knows that you want to move towards like people who have most context should make a decision. That's like, doesn't save the leadership of a company. This is literally what I'm talking about, creating space for creativity, because I want the decisions to be made locally on the ground.

• 1:31:04Speaker 01

  So were the arguments for staying private back then just memetic? They were just repeating what everybody else was saying at the time? I think people are generally right. It just doesn't, it washes out. But like, again, people have problems with the concepts of like, very often, a new idea is dismissed because someone can formulate an idea, like a reason against it, and somehow that dismisses the entire thing, right? Like, we live fundamentally, most of people spend their entire lives sadly in a vitocracy, right? Like where you need everyone to agree to do something, but you only have one person to vote against it to not do something. And again, good companies

• 1:31:44Speaker 01

  overcome this in important ways. And so similarly, one good argument dismisses the entire idea is a very common way to evaluate options. What people very often don't do is reformulate all the arguments against the status quo, right? Like the thing we're doing right now also is flawed. It's just, we really understand the upsides and downsides. The new thing might have way higher upsides, or actually, maybe not. Maybe the upsides are obscure, but like, or hard to know for sure. But the downsides are clear and we can be formulated. Therefore, the usual default position is not do it. So this is, I think, is incredibly

• 1:32:26Speaker 01

  undisciplined, because you need to think in, you know, propensities, you need to think in chances, like, and sometimes you need to like really, really load up a decision for all the pros and cons that can be articulated and make it, make it a little bit like in your mind, like, look at where the scale comes out. For a company that's trying to sell like the e-commerce platform for everyone, especially for the many American companies, being a Canadian private company that's tiny and is not, is not ideal. So.

• 1:32:58Speaker 01

  You know, like, people don't usually go public because of a marketing or like name recognition, but like.

• 1:33:03David Senra?

  Yeah, super valuable.

• 1:33:04Speaker 01

  Anyway. Put it on the pro side and then put everything else on the pro side, too. We might get better people looking for us because some people really want liquid stock. Um, like, and so, you know, so on, so on, so on. And in the end, it's like not even close. It's just, you know, the downsides were like a couple of annoying phone calls. I have to do a couple of quarters, at least for the first 10 years, I suppose. Um, and, um, the, um, I thought actually most of the process was actually quite valuable. Like, like I learned a lot about my own business having to.

• 1:33:34David Senra?

  Explain each other.

• 1:33:34Speaker 01

  Exactly.

• 1:33:35David Senra?

  There's been a few previous guests on the show, Brad Jacobs, John Mackey, Daniel Ek, obviously running public companies. In Brad Jacobs and John Mackey's case, they both said like Jacobs makes that point. Well, one, he thinks it's like wonderful free marketing and advertising. Two, you now have a current, like you have a currency. Mackey said the same thing, like it benefited Whole Foods being public fast because then he used that currency to acquire a bunch of other competitors and accelerated his growth. But Brad Jacobs' point was just like, he likes the pressure of that check in.

• 1:34:06Speaker 01

  Yeah.

• 1:34:06David Senra?

  Where it's like, this is what I'm trying to do with the company. This is what I'm saying to do in the company, and this is our results. And I want somebody to say, oh, like, there's a big disconnect here. And I want the pressure to like, to actually perform in like, and have somebody, these expectations externally. We talked about the environment that you're building at Shopify. I want, I'm curious about the, how you think about the talent that's inside the environment.

• 1:34:28Speaker 01

  Yeah, of course. I mean, ultimately, I really, really believe in the sort of stoic, maybe, uh, uh, Adlerian idea of separation of tasks. What have I control over and what I don't? I always love, um, particular formulation about, um, uh, thinking about how other people think about you. Like, again, you need to make yourself a person. worthy of being liked. If someone then dislikes you, that's up to them. It's not that it's not your job to make people like you. It's your job to be likable. And if they make the category mistake, it's their own fucking problem. Right. So it's a really, really freeing way to think about it. But talent, I um. My job is to make a company worthy for the best and brightest to work for.

• 1:35:12Speaker 01

  Like um, this is the part everyone skips. Everyone's like, oh, we need to hire a better recruiting team. Well, maybe you need to also just like uh be worthy of a kind of talent that you would like to have. Um. So I mean, this goes from like office space. If if you have any to a company uh like amount of bullshit people have to deal with to. How much um uh you know uh bullshit politics can you subtract from the whole thing? Um. And can your large company feel like a small company with lots of resources and lots of impact? Um, you know, it's more fun to ship software to millions of people that you really respect than to uh um. A few people who you then try to uh make a sale for at some point.

• 1:35:56Speaker 01

  Or like it's just like it's like, you know, impact matters. In a way, this is likely going to be misquoted, but I think the talent eventually takes care of itself. There are not that many good companies to work for. There are not many companies that that many good companies that deserve um uh the attention of people who can be of. By by the most capable people um because they have an option to start their own companies.

• 1:36:19David Senra?

  Interesting idea. There's actually not that many great companies. It's your job to make one of your companies, one of those companies that the best people in the world will want to. What do these people look like though?

• 1:36:28Speaker 01

  The reason why I didn't move to Silicon Valley is because I knew how to create geographical consensus um in the eastern seaboard. That Shopify is the best company to work for, full stop. And I just knew I had the ability to do it because I knew how to build a company that I would want to work for. And um I think. Given that I estimated I will need somewhere between a thousand people or something like this back in those days, I'm like, I'm gonna find another thousand people that think like me about how good a company needs to be to book for, and I can dislodge all of them. So if I go to Silicon Valley, I can't pay what Google pays potentially, or like someone else makes up for their skills issue by just overcompensating. Yeah, it's called compensation because you kind of have to compensate people for the shit you have to,

• 1:37:13Speaker 01

  you ask them to do. And, you know, like if there's a lot of shit you have to compensate people for, but you have enormous amount of resources, you can make up for skills issues by money. And so in East Coast, which was much more hedge fundy and much more high finance, and like for the kinds of hackers I wanted, I knew how to do this.

• 1:37:33David Senra?

  But wait, I want to pause there. I love this idea where you're like, I'm gonna build a company that I would want to work for.

• 1:37:38Speaker 01

  Oh, yeah.

• 1:37:38David Senra?

  That's on one end of the spectrum, which is great. You also had this like thought experiment that I heard you say before, which is like one of the worst things that could happen on the other end of the spectrum is you wake up 10 years from now and you built a company you don't want to work at. And then you have this great line I want to pull. It's like, that's dystopian. There's so many companies I wouldn't want to work for. Why did I use my life to build a company? To build another one that I wouldn't want to work for. You just should build a company that's worth working for.

• 1:38:04Speaker 01

  Yeah, like again, in your, you should take pride in your work.

• 1:38:11Speaker 01

  Like in the inputs and how you, like, did you accomplish your things you set out for in the aggregate, right? Like, be easy on the path, but like the outcome does, should matter to you. And like, man, I just shake my head sometimes with like how people overcomplicate these things. It's just like, it's kind of, man, people know what they're looking for, right? Like, and some, you know, I'm talking about very, very, very fortunate people here. Like people who have a lot of choices, who have like,

• 1:38:40Speaker 01

  Incredible competency and in some of the rarest skills and like combining this with enormous drive. Like a sort of you like this, like like a couple of attributes that all have to come together to be one of those people who can command like hundreds of thousands, millions of dollars of compensation package that you can make in this industry. But partly because you're worth it, right? Like you're contributing more than that to a mission. Like this, therefore you can command this kind of compensation and that's like the way this all fits together. I think of everyone as an entrepreneur, really. Your capabilities, that you are the entrepreneur of your own work output. Your product is what you can do and what you can accomplish.

• 1:39:25Speaker 01

  Your market is the companies that exist and you are selling a exclusive subscription.

• 1:39:34Speaker 01

  That's the institution of employment, right? It's a it's a two sided opt in relationship. Whenever people come to me and saying, hey, how do I earn more money? It's like, well, be too good to ignore when we increase compensation. It's like, you know, like, be better. You're making this amount, you would like to make this amount. In which way have you become so good that you can add that amount of increase to, you know, just like the collaborative project we all work on? And so I think that's just sort of clarifies and simplifies things, right? So I mean, all this said, I don't want to sound it like make it sound like it's inevitable, but if you just do all the right things, you end up like

• 1:40:15Speaker 01

  there's always a information gap and reputation lag and I'm out there recruiting and telling people about the company a lot. What helps me a lot is people are curious about the company and I've heard about the company and so on now. That's that is because of things that were under my control. I tell people that it's an unshared attention company. There's no part time jobs. You will have to put a lot into it, you're gonna get even more out of it. You will make great money, but we attempt to never be the highest compensation play bit.

• 1:40:51Speaker 01

  Because we have found that the people who Optimized for that above all else, actually don't do well at the company.

• 1:40:58David Senra?

  Because Shopify is a mission-driven company.

• 1:41:00Speaker 01

  Exactly. And the thing I'll promise is like, in terms of your own skill set, partly based on demand, partly by osmosis, and partly based on culture that's surrounding you, you will advance vastly faster at Shopify, building capabilities, skills, and correct ways of thinking and mental models and these kind of things than I think at any other place. Therefore, the compound return to your career is going to be vastly higher here than anywhere else. Because you get to a potentially higher compensation level earlier in your career because you're worth it. The entrepreneurial story is very fractal in Shopify. It's just like, what is your product, what's the market, and does it fit?

• 1:41:43Speaker 01

  So it's just make this is a clarifier that I think is worth talking about.

• 1:41:47David Senra?

  I'm going to quote David Ogilvie again because I think it's interesting. He says like, "Talent is most likely to be found amongst non-conformists, dissenters, and rebels." So when I asked the question about like, hey, we know the environment, we have a description of the environment, what are the people in the environment? There was two ideas I got from two separate entrepreneurs. I've mentioned both of them already, but I like because they use the same terminology when they're looking for talented people to hire in their company. Daniel from Spotify and Kareem from Ramp, and they both said the same thing to me. They hire for spikes.

• 1:42:18Speaker 01

  Spikiness.

• 1:42:19David Senra?

  Spikiness. So a lot of people, a lot of big corporations, they want you like well-rounded. Like, no, no, this guy might be a bipolar alcoholic, or this guy might, you know, have some other, might not shower.

• 1:42:29Speaker 01

  Yeah, yeah.

• 1:42:30David Senra?

  So like Steve Jobs, he was hired at Atari. Everybody's like, Nolan, Nolan Bushnell, the founder of Atari, like, you can't hire this guy. He stinks and he wants to sleep in the office. And Nolan's like, yeah, but he's really talented, so he's going to sleep in the office and you just got to hold your nose when he's around. Do you, do you agree with the idea?

• 1:42:44Speaker 01

  A hundred percent. It's like, exactly. It's, it's like, we never look at the credentials and stuff like this. I, again, I'm a high school shopper. I would be like rich if I would start making everyone want to have PhD. The path by which we do it is we go for a life story. We ask you like, hey, give us your story. And this is a very important ingredient in our hiring process. And frankly, what we're looking for is like high agency experience. We look at like, something went wrong in your, in your story at some point. Well.

• 1:43:14Speaker 01

  Now let's zoom in. How do you react? Give me minute by minute. This is what we know and now, right? Because a lot of us are entrepreneurs. Even everyone, like I talked about the founders of companies you purchased, but like most people just in general in Shopify are entrepreneurs. Many started Shopify stores, built a business and then found a company and applied for a job and got a million. It's like, so this is, um, there's a huge amount of building, company building background. And we want to be surrounded by people we admire. That's, I think, the biggest product any company can deliver to our employees is so, is that every day we're surrounded by people they deeply admire and can learn from. Like, so it's a very important part of this. So lots of entrepreneurship, lots of entrepreneurial impulses. And then, so we look for this high agency behavior.

• 1:43:59Speaker 01

  And then, um, you know, obviously, did you drive a particular craft that you're applying for to excellence? How do you think about this kind of thing? Can you just sort of talk about the excellence or actually perform it? And then, um, you know, this is really what we fill our buildings with. And, uh, you know, just like, again, create the space then and that can be creative. And this sort of, this is how it always works and it's, it's, it's worked really, really well. We couldn't do anything other than this in the beginning, right? Like in the beginning, we had no money, like really zero. I didn't take a salary for, I think, four, four years.

• 1:44:42David Senra?

  I heard your father-in-law covered your payroll when you couldn't make it.

• 1:44:48Speaker 01

  That's right. So, yeah, we were living with my parents-in-law, Fiona, my wife's older bedroom. From which I also added, I put a key desk and I built a lot of Shopify from there. And, uh, you know, like, I mean, just kept cost low, but that was the main thing. Make every dollar count is something that's, I'm so glad, like. This is what I worry sometimes with all these really, really big seed rounds like money. Mainly money doses, it gets you, I mean, sometimes it reveals, but usually it just like makes you get a whole lot more of what you got before.

• 1:45:29Speaker 01

  And people did raise early partly because they were not tied with money. Then you get a whole lot more tied, not tied with moneyness at larger scale and it gets really, really bad.

• 1:45:40David Senra?

  You're making my heart sing because I feel like I'm like on an island by myself about this because I've spent 10 years reading 410 of these biographies. All of them control their costs like crazy. They'll tell you one over again, constraints to your best friend.

• 1:45:52Speaker 01

  Yeah.

• 1:45:53David Senra?

  And then I talk to these young founders, I usually don't meet startup founders because I'm not an investor, but a good friend of mine is like, hey, meet this kid, meet this young kid. I met him and one of the things he was talking about is like, yeah, let me show you pictures of like this beautiful office we're moving into and he was showing me everything. And I was like, this is stupid. Like you haven't done anything. You don't deserve this.

• 1:46:11Speaker 01

  Yeah.

• 1:46:11David Senra?

  And I go, go look at like, what, where did like Apple start? Look at Microsoft. Microsoft started in a strip mall in Albuquerque, New Mexico.

• 1:46:18Speaker 01

  Yeah, right.

• 1:46:19David Senra?

  And you need a triplex in Soho? Like, what are you talking about?

• 1:46:22Speaker 01

  It's so true.

• 1:46:23David Senra?

  The question I, what I pointed to him is like, okay, how does this make your product better for your customers?

• 1:46:29Speaker 01

  Right.

• 1:46:29David Senra?

  And his answer was, well, I'll be able to recruit better talent because office is nicer. Then you don't have a mission.

• 1:46:34Speaker 01

  It can work, but like, I feel like you're not increasing.

• 1:46:38David Senra?

  You built a $200 billion company in your wife's childhood bedroom. That's where you started.

• 1:46:43Speaker 01

  Yeah.

• 1:46:43David Senra?

  Like, maybe we should repeat that over and over again. Like, just go look at where these companies were. What? You mentioned the Larry Ellison episode I did earlier. Like, they were in a shitty office building.

• 1:46:52Speaker 01

  Yeah, yeah, yeah.

• 1:46:52David Senra?

  Like, and like, I think they had three, like, three separate rooms. Oracle, that's where Oracle started.

• 1:46:59Speaker 01

  I think, I mean, there's a well documented effect of when companies build monuments to themselves, they usually decline right after, right? Like, so, but that has a long running history and business history. I do think there's an art, like, I do think.

• 1:47:17Speaker 01

  That completely under invested into office space for a very long time. And it actually was a mistake. I think I think space around us is actually extremely important, but it doesn't need to be expensive. Like, like, um, uh, that's probably an aside, but like. Oh, let's go down there. What does that mean? It's just like, so again, we didn't have a lot of money, but we wanted nice office spaces. Um, there was, uh, this was the decades where there was a lot of open concept versus own room office spaces, right? Like was sort of a kind of fight. My co-founder is a, Daniel Weyn, and he's, um, he's a polymath. He learned programming when I asked him that I needed some help with programming and just like was good. Immediately, which was annoying as hell.

• 1:48:03Speaker 01

  And, um, um, before he was our designer and just like literally everything else too. Now a DJ and before that he won poker tournaments. So it's like, it just like, it like keeps going. It's like one of these little, it's actually really, really helpful to have someone like Daniel as a childhood friend because it really, really, um, misleads you about human capabilities. Like, because this is just your buddy who does stuff like this. Um, anyway, uh, he, uh, at some point, like, he really, really tapped into this. No one can be more creative, um, than the space around them. And no one can care more than the person they work for, right? That's the way he, um, like, sort of created this, um, uh, philosophy around this. Um, I, I told him, look, here's, here's max budget and we are getting like B office space.

• 1:48:48Speaker 01

  That's like kind of cool. And you need to figure out how to create play spaces that are like a 10 out of 10 on doing word plus work. But inexpensively. But like, you'd need to figure out, right? It's cheap, right? Like, so, um, man, I mean, we built a bunch of offices in a row and Daniel was insanely good at this. How many years into Shopify? This is like 2010, I think 10 was the first one. It's six, uh, six years in founding, four years after Shopify launched. Um, uh, we went out of like sort of above a coffee shop. It was like really nothing, um, to, to our first office. So how do you do this? They're like, he said, like, first of all, the, the economy is wrong. It's not between open office and, um, uh, like.

• 1:49:34Speaker 01

  Like closed office spaces, there's like perfect midpoint. Because and it has to come from your strategy of projects. Shopify loves the five person team. We increase to eight sometimes, but we think the best team size is one. Because like a single offer can do things that is impossible to do for teams and hit high notes that are unreachable. But I think Plaid have has rather played the field of what can be done as solo projects, actually changing again because of AI. But like, which is very exciting bit, but like most projects worth doing need to be done in teams. Then there's a magic number at five.

• 1:50:15Speaker 01

  It's sort of what military ends up like figuring out to like they test these things and come to the same conclusions. You can sort of temporarily go up, but then at some point you have to split teams and parcel out the tasks. Each of these creations is like a figure ten X loss of productivity. So Shopify is like, although like our team is I think three and a half thousand people. It's really lots and lots and lots of small teams.

• 1:50:39Speaker 01

  And this is also why we need this legibility coordination layer that I talked about earlier. Okay, so pods. They figured out how to make pods that are like exactly, they are private enough while being open enough. They never make the office feel dead, but they also draw you around. It's like, what's a pod? What does that mean? It's just like a, it's a room that just like sits up to like, when you put the seventh person in, you, it's uncomfortable. Like it's like, again, think about how much policy you don't have to post. And if environment just makes you do the obvious thing, you can play with uncomfortable, too many people in this area.

• 1:51:21Speaker 01

  Like when you know what you're doing, now you don't need to post a policy about how many people you want in a pod. And people self-organize into five people teams because that's the most comfortable thing to put in a pod. So. Not meeting rooms, meeting rooms go in the middle on our limited floor space. Because we don't want people to spend all day in meetings and then get out of the dark rooms. We put like, everyone sits around the windows in pots and they are like structured in such a way that, you know, it all works. The coffee area is on the other side to create serendipity. We cut through every floor eventually to create stairs that we move teams in such a way

• 1:52:03Speaker 01

  that certain teams that have to work together but work on infrastructure separated them out in floors so that they going to each other would run into other people who are using the infrastructure to, you know, and so on and so on and so on. So, design being super conscientious about this is really important. Daniel did an amazing job. We, I think we open sourced the floor plans and I think lots of, lots of mod. This is not interesting anymore when you look at what they look like because I think that work has gotten up the top end of the tech industry as a right midpoint. And, but many people cargo-called it, they just Xerox copied it essentially instead of understanding. So they make pots too big or whatever, you know, these kind of things.

• 1:52:47David Senra?

  We talked about car reculting a few times. You observe that behavior in other companies. I'm curious what internally you have caught your own company car reculting.

• 1:52:57Speaker 01

  Oh, we actually, we are in a Toronto office here. The Toronto office actually has a few floors that are clearly mimicry of these ideas that Daniel figured out, but are not, they don't understand where these come from. Like again, pots too big is like more, the nice meeting room is right at, on the window, has lots of light. You know, just like, again, maybe this is okay to have a few, but like, I went with the teams through it because we then changed some of the floor plans after they moved here and realized like, holy shit, this is like, oh, Norman doors everywhere. Fuck, that's the craziest thing.

• 1:53:42David Senra?

  Wait, what?

• 1:53:44Speaker 01

  Fundamentally allergic to Norman doors.

• 1:53:46David Senra?

  What's that?

• 1:53:46Speaker 01

  Doors that you push, then.

• 1:53:49David Senra?

  You can't tell.

• 1:53:50Speaker 01

  You can't tell.

• 1:53:50David Senra?

  Yes.

• 1:53:51Speaker 01

  Yeah, this is most like the most fundamental design error that you can possibly make. It's like create affordances on a product that make people. Predictably do the wrong thing. Like, like, this is such a, like, like, literally everyone who's ever involved in a process of designing a Norman door should, you know, revoke their design license, like, I'm being facetious. Obviously, that isn't a thing, but like, it's like, it's just like, man, it like, yeah, skills issues as a door is like very common occurrence, I think, in places that are unconsciously designed and like, all those doors are replaced very fast.

• 1:54:31Speaker 01

  Like, I mean, the funny thing is, you can usually turn a Norman door into a non-Norman door by cutting things away and like, putting a push plate somewhere, you know, so that helps. So I, I, I make a big deal out of these kind of things. Like, it's just like this needs to, like, I cannot surround people with things that are underperforming, the quality that we, of, of engineering we want to do.

• 1:54:55David Senra?

  And that's down to the detail of the doors in the office?

• 1:54:58Speaker 01

  Yes.

• 1:54:58David Senra?

  Wow.

• 1:54:59Speaker 01

  Yeah, um, yeah, of course. Yeah. I mean, because product is not a thing. Product is an abstraction. Product is a name, but like a handle that you put on some, on some totality of a body of work. From the perspective of a people creating product, product doesn't exist. It's what other people call your work. A product is just details. It's many, many little details that are appreciated if they compose right and make a bloody mess if they don't, right? So, um, so from the inside perspective, you have to sweat all the details away. You do anything, that's how you do everything. And, um, that is absolutely down to the floor plans and, you know, the ambient noise levels and so on. Just like, you're going to a room, it's like that, like silent.

• 1:55:43Speaker 01

  It's like, it's just like, you, you, you notice when you're talking while going to a meeting room, um, uh, at least on the floors be fixed, um, based on previous specs.

• 1:55:54Speaker 01

  It's kind of a comfortable talking hallway because it's so echoey. Then you walk in a meeting room and immediately like it's just a different noise level because it's just like diffuse. We have enormous amounts of like, in fact, we actually worked with companies on Shopify to create the products of sound dampening that are now really, really like supply all companies, tech companies. It's really fun. And so, in fact, like everything in our offices is from Shopify stores, right? Because again, like if anything we are doing is not mission aligned, we just didn't align to a mission, ax thematically. So, you know, just you can go pretty far in these kind of things. When you need something for office spaces and it's not on Shopify, we usually put a call out for someone to start that

• 1:56:38Speaker 01

  thing. So it's on Shopify and we help them get started and build the thing. And then we can maintain our 100% Shopify quota. So it's also fun.

• 1:56:49David Senra?

  That's incredible.

• 1:56:49Speaker 01

  We did at least one enterprise sale with a supplier because we really wanted their floorboards and for something they were really like look great and were at the right price level. And like, yeah, but we can't place for order unless you come to our price. So sometimes we are maybe cheating.

• 1:57:07David Senra?

  That's actually a good way to get a customer.

• 1:57:08Speaker 01

  Yeah, it's also a funny way of doing enterprise sales.

• 1:57:11David Senra?

  Want this thing, but you just need to migrate over to our platform first.

• 1:57:13Speaker 01

  Yeah.

• 1:57:14David Senra?

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• 1:57:57David Senra?

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• 1:58:41David Senra?

  I mentioned my friend Kareem a few times. I went to his house last week. And I was like, dude, I'm talking to Toby. He's also obsessed. He has an engineering mindset like you. He's obsessed with playing video games. And you've mentioned a few times where like, you know, you thought you learned more about building a company from like Starcraft than, you know, talking to a bunch of people or reading a bunch of books. But then, his whole thing was just like, he's gotta feel like it's even building with AI now is even more like a video game.

• 1:59:10Speaker 01

  Yeah, 100%. Completely. What's the? Factorio, yes.

• 1:59:13David Senra?

  Okay, so that's the example he gave me. I haven't played the game. Can you elaborate on this?

• 1:59:16Speaker 01

  I completely agree. So like, so again, this is like, man, the world has such a weird way of like, somehow changing itself around me to make this stuff that I thought was irrelevant relevant or is late in life. It's like absolutely amazing. It's just like, okay, so video games. Video games are best thought, I mean, this depends very much on the video game, but in the aggregate, they often say the good video games are simulations. They are world upon itself and you're an a high-agent actor and you modify things. You take, you perform actions. You make decisions and then the game rearranges itself, giving you a feedback loop of usually a very quick feedback loop because I was an fan. But you learn about consequences of your actions. So like

• 2:00:02Speaker 01

  competitive multiplayer games are very obvious there and Starcraft and strategy games. They're not that popular as a category of games anymore, but like You know, when I was going through my teens in the nineties, like Starcraft was the biggest game. And, you know, I loved it because it was really, really hard. It was like easy to learn how to master, which is exactly, I think, a hallmark of everything that's worth doing. For motorsports, for kiteboarding, for my hobbies, tennis. All these things are like this. But like, it specifically is like honest in a way that like, there's like two people on the map mirrored. Everyone has the same potential every single game. And one person wins at that.

• 2:00:45Speaker 01

  Right, like it's like, additionally, it's a game of imperfect information. It's not like chess, you don't see the moves. You see only some information that you, like, in fact, you have to invest, you have to use one of the things that could get you resources instead to go to the enemy base to figure out what he's building. And then you need to interpret this. So all these kind of things is like, what you learn in this game is information is everything. Like, there is no right decision, there's only context in which decisions turn out to be correct. And while resource management is extremely important, you have to understand that resource management is not just quantifiables.

• 2:01:25Speaker 01

  It's not just minerals and baspin gas that you have to manage, which allows you to build units. It's also your attention. And frankly, attacking other people's attention is much more profitable very often in a game of Starcraft than it is to actually attack their base. Because if you overtax their ability to pay attention to things, they will make mistakes. How do you overtax their ability to pay attention to things? You can do an early attack, you can do any number of things, especially if you play against the same person. When you get a very high level, you will play the same people over and over again. They get a sense for how you play. So at that moment, like, there's always been the people who are just incredibly prepared, right?

• 2:02:05Speaker 01

  Like, they're just like, they perfected playing a single way, which my players are always different, chess, Starcraft, all the same. Like, I disrupt other person's play. Like, I do moves that aren't in books, right? Which are, they're not in books because they're not good. But other people can't deal with it because they need their preparation. That's like their their their skill set is their ability to play chess is the crystallized intelligence, not the fluid intelligence to deal to roll with the punches. And so, you know, like I I learned a lot about myself doing this. But I also learned about a lot about, you know, how do you like, you know, just like how to approach a game, like how do you how do you get better? How do you how do you get more out of every game you play?

• 2:02:50Speaker 01

  Because like I I never ever in my life had as much time as some other people could to invest in something like this. So I always had to like, how can I get more skill progress units out of out of the time I have than other people out of less constrained calendars, right? I'm talking very fondly of StarCraft. It might just have been oddly the right teacher from here at that moment and the student was ready. And so I could have maybe learned the same lessons from any number of things. But I think it was specifically good because of it being a simulation. You start a new game. It had skill-based matchmaking, so you should play against other people of your skill set based on, you know, elo rating.

• 2:03:36Speaker 01

  And so you had a very, very clear sense of you started winning more games than you lost. That means you were progressing where if you started losing more games, if you were regressing in on an absolute scale compared to all other players in the world. And I think that was a perfect little sandbox to explore how to, you know,

• 2:03:56Speaker 01

  think about when it's time to build infrastructure, when it's time to invest in resources, when it's time to prepare, when it's time to reveal your hand, when it's not time to reveal your hand. And I think it was perfect for perfect place to spend time for me in my teenagers years, given what I did afterwards. So back to your AI question, I just find that looking at AI like agents, especially the like, I mean, we are recording this, this is like week three of 2026. If we would have recorded this in week 52 of 2025, it would even be different, right? Like I might not even make this analogy so strongly, but that's how much is happening,

• 2:04:41Speaker 01

  that the world changes every three weeks right now. We figured out some new harnesses for agentic loops that are much more autonomous and frankly, supported by models which didn't exist at the beginning of December even, that can perform at this level. And so I look at my computer and I have like six different agents going, all coordinating between them, they send emails to each other, which I think is hilarious. And so, you know, just like, I'm like, man, this like is starting to really look like, start to start to hurt my attention is paid, like this one is currently working on a module for what I really, really need. So I'm zooming in, paying attention, doing a little bit of micro, giving a little bit

• 2:05:23Speaker 01

  of extra, double check, sort of the output of the critic, which looks at all of them all the time to figure if they're still on task. It's the exact same thing, right? Like it's like, it is a fascinating time. It's just like, I can't describe how fast progress is right now. I just like, you know what I tell my team, it's like, you know, 21 years now, starting companies is really, really, really hard, right? So first years, let's like, just like, that's interesting and everything's urgent because like you're getting to a margin. I got like within a week of running out of money so many times and sometimes you're burnt out.

• 2:06:01Speaker 01

  Many times it was like, just like, it like the clearance of the one time try hurdles that shop ran through was like millimeters at times, like there's so like, I bet you if you run the first six years simulation 10,000 times, you would not succeed in most of them, right? So like, like in a way, like luck is a big component, timing of these kind of things, people luck especially. After that, you know, IPO, you think that's probably the most interesting thing a period of the company. I think it was hard and maybe not terribly interesting, right? I guess financing event at the end of the day, maybe, but some, some aspects were interesting, like figuring, but like there were aspects of how we make it our own as a process like that.

• 2:06:47Speaker 01

  That probably this is why I did it. It's why we made changes of to the process or why we wanted to have our own stamp on it because I didn't want to join someone else's process. I wanted to have it my own. Then there's COVID, which was very, very hard, definitely not interesting, actually fucking annoying mostly. And so I'm like just trying to figure out like 2026, man, this is going to be hard and interesting.

• 2:07:10David Senra?

  Those are the things you're most attracted to, hard and interesting?

• 2:07:12Speaker 01

  Year 21 is like, this is going to be the most interesting year in our, in, in this company's history, probably in everyone, I think literally everyone's career. Just everything is lined up. It's like, doesn't matter what you've got, like everyone's going to be measured against how well did you prepare yourself? Like what your skills at? How quickly can you react to everything that's happening? How quickly can you readjust? How quickly can you re-arrive everything?

• 2:07:36David Senra?

  You put out this internal memo where you're just like, I think it's, you know, the language better than I do, but it's basically, it's a company expectation that you, the first thing you, when you have a problem, you reflexively try to use AI. When did you put that, that out? A year ago?

• 2:07:51Speaker 01

  Yeah, no, maybe not quite, but like something along those.

• 2:07:54David Senra?

  And people were just like, this is ridiculous. There was like some pushback and now to your point about how fast everything is moving. It's like, of course you would.

• 2:08:00Speaker 01

  Yeah, exactly. People will look at that memo in three years and just like, he didn't say anything.

• 2:08:06David Senra?

  Like saying the sky is blue.

• 2:08:07Speaker 01

  Yeah, exactly.

• 2:08:07David Senra?

  So this excites you? What's it like?

• 2:08:09Speaker 01

  Oh, yeah. Man, I love that. It's like, this is what I'm here for. Like, it's just like, I, if I, I wouldn't have happened. I don't think I would run top five anymore. It's just like two, like, there's much better leaders if in times, like,

• 2:08:20David Senra?

  Whoa, what?

• 2:08:21Speaker 01

  If times is stable.

• 2:08:22David Senra?

  Yeah, but I thought you were in love with this problem.

• 2:08:24Speaker 01

  Yeah.

• 2:08:25David Senra?

  Unsolvable problem. So you'd still work on, but you wouldn't be running it? What do you mean?

• 2:08:28Speaker 01

  I mean, I think I would be, no, I probably might try my hand at a different aspect of helping people self-actualize. Like, I mean, my, my, my personal mission is to cause more entrepreneurship, right? Like that's like, I, I'm going to adjust my own career by have I. The thing I discovered that was meaningful to me, have I had the maximum amount of other people do this thing?

• 2:08:49David Senra?

  When did you realize that was your mission?

• 2:08:51Speaker 01

  So I know exactly because it was like preparing for one of those internal events, summer talks, which I was like, it's always a bit of a like soul. Like I do a lot of this like message in a bottle reading and like self introspection. And it was like, it was 2014. I was preparing for my summer talk and I'm like, my biggest struggle was with my own identity. Like again, I was, I think I was mentally preparing for the cosplay period, which I again, wish I wouldn't. But like, I was like, but I like engineering. I really, I wanna spend my day hacking on stuff and building things, not managing.

• 2:09:33Speaker 01

  And so I, again, I used my trick partly to give a talk on something that I was sort of come to realization, but maybe not fully internalize. To basically, I said, I loved engineering because it turns out that was the way how I as a kid, when I started doing it, could build things. What I actually love doing is building things. And specifically, I love doing like building things that share a thing that like I have experienced. This is a moment of becoming an entrepreneur, getting your first sale. And so I made a talk of combining those two things and just saying like my mission

• 2:10:19Speaker 01

  in life, my craft is actually building things in general. I built, I started with products, like code, I then create products. And now I create companies that create products and I engineer those. And that caused more of this kind of thing. So I kind of wrote that as a personal mission for me and said like, I will attempt to run Shopify and try to be the best CEO I can be until someone taps me on the shoulder and say, other people could be better for this company as long as it's in cohesion with my personal mission. But I'm also like, I'm perfectly fatalistic about this kind of thing. I don't, I don't do a job for money. Like it's like I do it because I feel like I can contribute a lot.

• 2:11:02David Senra?

  I love this idea that you view entrepreneurship as a way to get self actualized.

• 2:11:08Speaker 01

  Oh, yeah.

• 2:11:10Speaker 01

  I mean, much more honest.

• 2:11:12David Senra?

  But it's also your form of entrepreneurship. I was reading, I never read comments of podcasts and YouTube videos, I highly recommend against that. But people are telling like, this is like one of the good entrepreneurs. This is like what you're building and the other entrepreneurs you're trying to to enable. It's not like they're crony capitalistic. There's like a lot of like dirty part, I'm just capitalist as they come. So I understood what that that comment meant. Out of every single note that I took from all the talks that I've seen you give before, the one that was at the top of my list is exactly how I feel about what I'm trying to do. And you said, focus on craft and giving a shit. And you said, it doesn't matter that a bunch of this stuff isn't quantifiable. It's exactly how I feel.

• 2:11:52Speaker 01

  It's such a basic thing, but it's like, why, like, it's so, it's, it's, it's so simple, but it's just not easy, right? Like in any which way, like, companies hate quantifiables, in fact. It's like, it's amazing to see it, like, man, you hire the first team together and like if you get to talk about building a company on podcasts, that means you were successful. So the first team clearly did this and therefore the first team was very good. And first team you hired best on your gut. You just knew, these were the people you needed. You make mistakes, but you correct. That's all just sort of like judgment, taste, maybe even bias. Like, I think we need to move nostalgia into the bad category of words and bias into the good category of words, because bias is actually perfectly fine.

• 2:12:37Speaker 01

  It's like, it's like, without bias, you actually have no convictions. Like, you, you should try your convictions. This is really what I learned from the thing. So you make the first team as a pure play. This is the best, I know how to make decisions. And then everything, everyone wants you to write it down. And you know what happens when you write it down? Like, here's the things that you are looking for. Here's the, the thing. Wow.

• 2:13:05Speaker 01

  The people who read it are the people who are very, very good at following this. So the people that you probably described, not the people who go look for the cheat sheet. The people you are trying to avoid hiring are the people who will study the cheat sheet very well. So you just gave everyone a like a way of performatively doing the thing that you want to see without being intrinsically like this, right? And so you end up like very quickly losing your company once you systematize things. However, everyone is telling you to do it. There's a giant conspiracy against these things, taste, quality.

• 2:13:50Speaker 01

  If it can't be put in numbers or can't be written as a list, companies hate it. Yet almost everything you have to do to build a great company is other things that are these things. And you shouldn't write down. Actively avoiding to write something down is sometimes the most important thing you can possibly do.

• 2:14:10David Senra?

  Do you think it's also related to the way you brought up sunk costs a bunch of times?

• 2:14:14Speaker 01

  Yeah.

• 2:14:14David Senra?

  Where it's like, well, I wrote this down, I changed my mind, but there's some kind of human element where it's like, ah, I don't want to contradict this because it's in writing.

• 2:14:21Speaker 01

  Yeah, exactly. Again, people like to be consistent over time. I just don't find that important. I found the cheat code to always being right is just like change your opinion every time you get better information. Right? Like so, because as you get closer to a point where you have to make a decision, that means you will wind up the right one. It's like if you do not stop at some point to incorporate new information, right? Like and even if you were wrong and if I figure it out, you know, again, what do you do? Right? You have two, you have one momentarily chance to steer your concern to the best possible outcome.

• 2:14:59Speaker 01

  Are you gonna take it? Or are you gonna be the person who just leans into the comfort of somehow character consistency? Like, why? For what? Like, again, what's the job you wanna do? Is it wanna look good or be good? Right? And so you're gonna like just change.

• 2:15:14Speaker 01

  Like, it needs to be okay to change your mind when better information comes along. And again, here's the crazy thing. I think if you go through the transcript of this podcast, you will find, or just ask an AI to do it, it will probably point out various contradictions inside of what I'm saying about what you do. Like, I'm like, in this, I'm probably on multiple sides. The reason is actually, this is almost the most important thing. It's, everything comes in layers. There's like just so many different, like, what's the operating, the optimal operating system in some frame of reference is often contradictory on the opposite of a larger frame of reference. Because, you know, I like this box, talking about boxes,

• 2:15:57Speaker 01

  because like inside of a box, it is, after a while, you can have a map of it. You can eliminate all the corners and you understand what's there. You may decide what was the right box to pursue. Maybe you need to like figure out, like, maybe you need to bend it and say, okay, actually, the problem is actually an aspect of another problem. And maybe if I put a larger box, we solve that and this problem doesn't even need to be solved. That happens. But this is exactly what I mean. As you zoom out, you actually need to completely change the way you problem solve because you're starting to work much more on, with much longer timelines. You need to actually make bets at a high level that you shouldn't make bets with like

• 2:16:39Speaker 01

  infrastructure, because you can, like in engineering, again, you can run benchmarks, figure out if something is fast enough and it'll be a yes or a no. Right? You don't need to bet on the trajectory of, you know, databases are growing faster at a certain thing. It's like, you don't need to, you can measure. So there, you wanna be super quantifiable. Then you try to figure out which market to go into. Like, you need to figure out, well, Right now, you have to figure out how is AI going to change that market? Right? Like, it's because you need to figure out if we join market or you. Is that market going to be a temporary unnecessary aspect of something else we are already doing? And will it be absorbed into a different category of products?

• 2:17:17Speaker 01

  And is this still valuable for you to do and so on? And, you know, what are humanoid robotics going to do to the world of logistics? And, you know, you've got to work with trend lines mostly, right? Which is not important in many other decision making. So I think there's probably like four or five different levels by which you have to look at a problem. And that is actually a lot of the skill of a good executive is to be able to meet the team where they are and like help them talk about the outside world, quote unquote. Like, here is how their work relates to all the other frames of reference, all the other abstraction, and how it like sits as a part in the larger company. And everyone should be able to connect what their day to day work back to a mission.

• 2:18:02Speaker 01

  Like, it's not like you work on customer support. Well, you're helping people literally not giving up on being entrepreneurs, right? Like, it's not even subtle. It's actually an easy exercise to do for people when you ask them to do it. But it's distressing in how many companies it's actually kind of unstated. The company mission is some kind of set of platitudes or something that aren't actionable. Those are unforced errors, and I think things go better when you get them right.

• 2:18:31David Senra?

  Hey, real quick, I need a favor from you. Right now, I'm conducting a survey to better understand the listeners of this show. So the survey is entirely anonymous. It's going to ask you things like what your position is at your company, what your household income is, things like that. This information is going to help me both keep and attract the best possible sponsors for the show, which then in turn allows me to create the best possible conversations for you. Now, I don't want to just ask for something without giving you something. So as a thank you for completing the survey, I'm going to host a live stream on YouTube where I talk about some of the most important things I've learned from spending hours with the guests on this show and some of the best ideas that they have shared with me after our conversation. So please do me a huge favor and complete the survey. It takes just five minutes, probably less than five minutes for you.

• 2:19:16David Senra?

  But after you complete the survey, I'll email you a link to the live stream. A link for the survey is in the show notes of this episode and is also available on davidsenra.com. I love the idea of tying everything back to the mission. I do hope people go through the transcript of this conversation. I think it's gonna be incredible. I printed out some of them.

• 2:19:33Speaker 01

  And I'm sure people are gonna tell me about all the contradictions. And I think, again, this is the fun bit, right? You know, I find contradictions in my belief systems all the time because we are like balls of contradictions.

• 2:19:45David Senra?

  I'll get messages. I'm like, I'm listening to this episode you did in 2019 and you said this and on the new one you said this. I'm like, I've read 250 of these things since then. Like, what, you think I'm doing this to stay the same? Like, that's the point.

• 2:19:55Speaker 01

  That's right.

• 2:19:56David Senra?

  I had high expectations of this conversation. Toby, you exceeded them. I hope we do this at least once a year. And I think the next time we do this, we design with the constraints which you like and we just evangelize entrepreneurship and the fact that, you know, it's one of the most important things in the world. And I think you're creating a lot more entrepreneurs and I'm trying to create a lot more entrepreneurs with my life as well.

• 2:20:15Speaker 01

  I'll tell you one thing, because I'm not sure if I, maybe I've shared this publicly, but like, I think you're gonna get more mileage out of this than anyone else. The, um, when we did surveys with our customers, um, about, like, because we wanted to like, like, I mean, we need to identify where our customers, what they do, whatever we eat, these kind of things. What we have found, this is a long time ago, before your podcast existed. It was like almost 80%, a 70s, a high 70s of percent. People checked the box saying they have someone who if they send a entrepreneurial question to, would respond to the email in 24 hours. Um, and I initially thought that was insanely cool how many people have such a resource.

• 2:20:56David Senra?

  Sounds like it in the general population though, right?

• 2:20:58Speaker 01

  Eventually I clued in, I think it was probably on Wikipedia, I read about survivor bias, um, survivorship bias. And I realized, fuck, the reason why they are my customers is because they have someone who responds to these questions in 24 hours. It's the other way around, it's causal. Um, and, um, the concept of entrepreneurship is so underexposed and underexplained. It's sort of got better in the 10 years, 15 years since we surveyed. But I think, I love what you're doing because you're just bringing this constant, like, you're rolling this out for people to introspect, like, an entire life story of entrepreneurship, giving people the thing that is implied by the question is like...

• 2:21:42Speaker 01

  Do you have any exposure to the world of entrepreneurship in some way that you actually know what you're signing up for? Because the people who don't know it exists, the people who have no relation to it, or the people who don't happen to have some in the family or friends who at some point started anything, well, they just won't try. It's not part of their toolbox and just putting this part into more people's toolbox is because it's going to be so load bearing. Because I think actually in this world of AI, there's going to be disruption and so many more people than people believe have a plan B with entrepreneurship. And I think we can, I think making things will be much simpler in the world of just-in-time manufacturing and 3D printing and additive and resin printing and obviously products

• 2:22:23Speaker 01

  just humanoid robotics, dreadnought, lights-off factories making anything on demand and 3D printers in every home, or at least very, very commonly in homes now. You know, in that world, more people will realize and working with AIs about learning the skills of figuring out how to make the better cup and how to design a better version and not having a Norman door. It's capitalism, the best part, and I think it would be much more common and much more exciting and I just like it's so fun to work on. And like in that way, like you and I work on the same project, which I think is super, super cool, right?

• 2:23:06Speaker 01

  Like it's like because the information gap is getting the stories out, telling people that's possible and it's so important for people to then try and hopefully when they might use Shopify and then hopefully we can push them behind.

• 2:23:18David Senra?

  I love that. I appreciate you saying it. Appreciate the time. Thank you so much, Toby.

• 2:23:21Speaker 01

  Awesome, man.

• 2:23:22David Senra?

  I hope you enjoyed this episode. Please remember to subscribe wherever you're listening and leave a review. And make sure you listen to my other podcast, Founders. For almost a decade, I've obsessively read over 400 biographies of history's greatest entrepreneurs, searching for ideas that you can use in your work. Most of the guests you hear on this show first found me through Founders.