“$100M dollar brands are being built for boring products” - Harley Finkelstein of Shopify

23:43And that ability to completely ignore an org chart and rather focus on impact and like, hey, that person I saw, like, you know, he's in GitHub, he's looking at their commit and he's like, I like the way they wrote that. I'm actually going to elevate that person and let them do something, you know, something much bigger, much more creative. And then probably the last one I would say that we're kind of talking about it earlier is that I think what he's done for me is he sees a better version of me than even I see for me. I see a pretty good version for me. I've always been someone who's somewhat, you know, fairly confident in my ability to get better at stuff.

24:14But he basically always shows me that there is a new gear for me. And he's like, you don't even know that that gear exists yet. But, like, you think you're in the fourth gear. There's a fifth gear. And he's like, and his expectation of me and, frankly, I think the entire team is that we requalify for our job every year. And it's one thing to expect that your team is going to requalify. Frankly, he also believes he has to requalify every year. And the pressure that he, that, you know, like he doesn't put more pressure on anyone else that he puts on himself. That I think is an amazing thing. Does someone like him evolve into this like Jedi master type of guy?

24:49Or when you had 20 people or 10 people or whatever it was, was it clear that this guy is special? You know, I think a lot of people end up starting companies and working like, you know, spending their lives working with people that they probably would have been friends with in high school. Toby and I are totally different. I'm very, I'm like power extroverted. I love being around people. So remember, I came to Shopify as a merchant first. I moved to Ottawa in 2005 to go to law school, not to become a lawyer. A mentor of my t-shirt company, my t-shirt business that I had in college at McGill here in Montreal had gone, became, you know, pretty good t-shirt business.

25:23I was able to pay for my tuition and my rent and help my mom and my two sisters were going to private school that I was helping to pay for, that I was paying for. I was paying my mother's rent at that point. A mentor of mine convinced me to go to law school, not to become a lawyer, but he thought He looked at law school as being a finishing school for entrepreneurship. And he was a lawyer. He was teaching law at the University of Ottawa. He said, come to Ottawa. Go to law school here. You're never going to practice law. But I think it's going to make you a much better entrepreneur. You'll learn how to critical reason, how to write better, how to think better, how to articulate yourself better.

25:55So I moved to Ottawa, have no friends, never even been to Ottawa before. It's the capital of Canada. Never been there before. Get there. And I'm like, where are the entrepreneurs? Those are my homies. Those are the people I always hang out with. And I met Toby through that. And at the time, he was just transitioning from snowboards to software. And this is before I ended up becoming an early merchant. Even in 2005, he was thinking about what the future of the internet might look like. So do you remember, can you give us a bunch of those quotes? Yeah, I remember him saying, like, for example, one of the things that, like, payments should have been built into browsers.

26:27I'm like, what? He's like, yes, like the people that made browsers completely fucked this up. payments should be natively integrated, not through a third party, but natively built in to browser. That makes total sense. Identity should be built into browser entirely. So he was thinking about all the deficiencies of the modern web and then trying to effectively adjust Shopify's product to make those things much easier. The other thing I think that he had done that I thought was incredibly inspiring to someone that, you know, praise of the altar of entrepreneurship was at that point, there were a couple of companies doing e-commerce.

27:00There was a company called Magento, which ended up getting acquired by Adobe. There was a company called Demandware that ended up getting acquired by Salesforce. There was a company called ATG that ended up getting acquired by Oracle. And there was a company called Hybris that ended up getting acquired by SAP. And those were sort of the players there. There were some other ones too, like Yahoo stores, but no one is really doing major GMB or volume on those. And I remember him sort of thinking that, telling me that the problem with all of these companies is that they're built for existing entrepreneurs, that there's never been anything built for aspiring entrepreneurs.

27:33Meaning if you have an idea in the shower in the morning, you can then go to your desk and get it going right away. And what if we were able to give the smallest of entrepreneurs of companies of ideas, the same tools that traditionally only the biggest companies could have? What would happen then? Well, the end result is that you like we now have, there's now been a trillion dollars transacted on over, over a trillion dollars transacted on Shopify. And yes, we have some very large stores. But the majority of those of that GMV is the long tail small businesses and those homegrown success stories.

28:05Companies like Fashion Nova or Gymshark or all these companies that started at their mom's kitchen table that grew super, super large. So those are a couple of the things in the early days that completely changed my perspective on one, how to think about building. But remember also like my own experience was sitting in law school, hitting the launch button on my online store, my t-shirt shop. And all of a sudden I was getting sales from like Ireland. And I'm like, for$29 a month, I think it was$24 a month at the time. Like that was a dramatic insight for me that, okay, if you couple ambition and incredible product technology, you can actually change the entire like trajectory of entrepreneurship on the planet at a huge scale.

28:46Where has he been wrong? Where's the weakness? Where's the human side of this? Because it sounds amazing. Are you guys familiar with the Enneagram? Yeah. Okay. So the Enneagram is sort of, there's a lot of these personality things. The Enneagram is the only one, frankly, that I think is worth any review. But so he is an eight. The challenger, characterized by a strong desire for control, independence, and justice. They're assertive, decisive, and driven by a need to protect themselves and others. They're often natural leaders, confident, and willing to take charge. Now go to three. The achiever.

29:17Self-assured. What is it? Self-assured, attractive. There you go. Charming. Ambitious, competent, energetic. At their best, they are a role model who inspires others, but they have basic fears of being worthless, basic desire to feel valuable. Oh, yeah, that hits, man. That hits. So first of all, for anyone listening, if you are working in a team with a bunch of different personalities, it's a really effective thing to do to actually figure out what they are on the Enneagram. We've looked at, I mean, I've looked at every one of them. We've had coaches on staff at Shopify for over a decade. This is the one that I think is the most valuable.

29:48So knowing that, Toby being a challenger, of me being an achiever, he is really tough. I mean, when I bring him an idea, he will beat the shit out of it to a level that I have that I have not even considered yet. So it is not easy to work for him. But it is incredibly meaningful. Because what you end up with is outsized personal growth, he won't say 20 words when two will do he'll say two. And if the two are correct, and even though they may not be the most polite way to say it isn't care, he is he is seeking the best result. Like that is why he should be, you know, I will work at the company as long as he'll have me and as long as he's there.

30:25Because I believe he is the CEO that Shopify requires. No one will care more about that. But that doesn't make it easy, right? And like I know other companies, I talk to my peers, other companies are like, yeah, you know, like there is not a softness, but there is a collegiality to their culture. That doesn't happen at Shopify. It's not that we're not collegial. It's just like that's not what we're trying to achieve. Did you guys ever have acquisition offers? You talked about how Magento sold and the other guy sold. Was there ever a moment? Everybody sold. Where you guys had an offer or a discussion that you had to take seriously and you had a fork in the road moment.

31:01You obviously ended up independent. But was that always, was that the only way this could have gone? If you look at the history of IPOs, particularly in tech, you will notice that Shopify from a market cap perspective went public at a much earlier stage than most companies did. What I will tell you is we, first of all, did not return phone calls from corp dev teams early on, specifically because we didn't want to get into that headspace, that line of thinking. It wasn't what we were interested in. We wanted to build a 100-year independent company, and we knew that those phone calls may result in us having meetings and talking to them and thinking about it.

31:37And, like, we just didn't want that in our minds. It just – that feels like a real distraction. In fact, you guys know this too because you both invest in a lot of companies. once you take that phone call from a corp dev person at a big company you you begin to inadvertently or advertently start a process in your mind of a begin to think about what if what if this number is right what if the terms are good what if they have a you know what if there's a space for me at this company where i can you know the pitch that a lot of these companies make this big you know m &a conglomerate they make is like well you can do what you're doing at your current company but you You can do it here with more scale.

32:12So ultimately, we didn't want to necessarily have that even in our minds. So we didn't return those phone calls, first thing. Second thing is we went public at a very early stage because, one, we thought it would be the best way for us to be independent longer term. And, two, we felt the company was ready for it. Like the product was ready, the business was ready, the team was ready. That's not really the case anymore. I mean, other than two companies I'm very close to. The one is Klaviyo. You know, Andrew, who's the founder of Klaviyo, went public last year. And then Fiji, who was at the time CEO of Instacart, is on our board, went public as well.

32:43So you've had a couple IPOs, but generally companies are – and in the case of most of these companies, they're much larger. They're in the tens of billions of dollars of market cap before they actually go public. So we just didn't want to get acquired. We wanted to be independent. But were there ever times where you were like, I would like to take this deal. This would be nice? No. Truly, there was not. We did a very small secondary on, I think it was the Series B, which allowed me basically to buy a house, a down payment on a house. And what's your philosophy? Are you like a de-risker over time or are you like, fuck it, all the eggs in this basket?

33:20Like what's your philosophy around that? Because it's tricky, right? Like even if you believe. So money's – so my – so, you know, I mentioned my dad wasn't around when I got to college. My dad, you know, he was – I love my dad. He's a great guy. But my dad really never made it as an entrepreneur. and growing up, money felt emotional to me that some weeks we had and some weeks we didn't. We never, you know, we always had food on the table, for example, but there were times where I remember as a kid, often my mom would come and sit me down and say, hey, like, we're gonna have to, you know, tighten our belts this month.

33:50That tightening of the belt happened a lot during my childhood. And so when we went public, yeah, for the first time I had real money. I was able to, you know, I was on a 10B51, which in Canada we call an ASDP, an automatic share distribution plan. So I was able to take a lot. But, I mean, I don't think there's any better investment for me, my family, than Shopify. But I've taken money off the table so that I feel like my family is secure, my children are secure, we're never going to have to tighten our belts. And that's not a flex. That truly makes me feel I'm able to do better work because I know that I have a nest egg that is protected.

34:29What was the hardest moment at Shopify? What was rock bottom? What was the low? COVID was really, really hard. Maybe not for the reasons that you guys, I mean, remember Shopify went from something like, I don't know, maybe pre-COVID we were a$30 billion company. I have your revenue. I think in 2019 you were at$1.6 billion and then 2020 you were about$3 billion. That's a big jump. And it was a big jump in everything. Like what happened during the pandemic was, I mean, e-commerce as a percentage of total retail was sitting around 15 % in the U.S. So 15 % of all retail was online. And then effectively you had this pull forward during the pandemic where like we jumped very quickly to 20-something percent.

35:14Sean, to answer your question, what was the hardest time in Shopify? You know, we almost didn't make it. We grew from 1.5 to 3 billion. Can I finish my fucking story, guys? so uh so there there was there there was this manic like period inside of shopify like all of a sudden all these this pull forward for example like everyone all of a sudden needs to go online all these laggards that were just physical retailers eventually came online and i think at that point it was like just get shit done and then 2022 happened and like the market started going the other way and like we kind of found ourselves with a much larger team we found ourselves with a lot of side quests.

35:51Shopify also for the first time ever, I think we were not profitable. So I think that sort of post COVID hangover was, was really tough for us. And that's kind of where like, I think, you know, you asked me about the different phases. That's where I think sort of the next phase came into play, which is okay. Like, do we, we need to figure out like, what, what do we care about? Um, what, what is the right team size? What are our focus areas? Do we have the right people leading the company? And that was sort of this, like we recalibrated everything. That was really hard. I wasn't sure. I knew Shopify would make it.

36:23I wasn't sure if I was going to make it. Was there ever a time where you thought that Shopify wasn't going to make it? Pre-IPO, for sure. I mean, post-IPO things, you know, we went public at a time where we sort of knew what the next 10 years would look like. We were profitable. We were making money. We were, you know, we were subscribing to this whole, like, you know, grow top line and also grow bottom line. But pre-pandemic, there was, sorry, pre-IPO, So that was hard, right? I mean, we were bootstrapped for a while. There were times where we didn't know if we can cover payroll. But I think you have to be a little bit crazy naive.

36:55Sean and I, my last company, we were going to do about$20 or$17 million the year we sold, but I sold early in the year. Sean has a business that is in like, you know, he's got his hands at a bunch of things that are potentially in the similar range. I don't want to speak for him, but I don't think either of us have experienced this like$50,$100 million range where I'm like, oh then I could just like manage like three amazing people who do most of the work I'm in the phase now with my business where I'm like everything is fucking hard like if someone if someone quits I gotta go do the work and so what I want to know is like does that go away does it get more fun no no it doesn't but actually like I don't think any of this gets easier you just have different problems it's like but it's like the magic number we all have this magic number early on as entrepreneurs especially if you grew up the way that I know you know Sean Sam and I grew up the way that we, like, we all have this number and I'm like, when I get that, I can think, I can basically extrapolate my passive income from it.

37:49And that's going to pay all my expenses and I can do. And then you hit the number. You're like, it's like there, it's bullshit. It's complete bullshit. There is no magic number. Just like there is no stage of a company whereby you are cruising. It's just different problems, right? So the problems that I have with, with like at 7 ,000 people and a hundred billion dollar market cap are very different than what it had with like 70 people. Which problems do you enjoy more? This is my favorite stage of Shopify because as going back to the whole spiky object, the thing that I think I can add, the way I can add the most value to Shopify is through storytelling.

38:21And I believe now the microphone that I have because of Shopify size allows me to do it at this crazy scale. And I think for that, it means that like my life's work gets to be more amplified today than it did 10 years ago. I remember you've always been lyrical and good at talking. You are now much better. You are always good. Now you are, like, really great. Do you have, like, a writer? Like, is there someone who's going to watch this and be like, this bit hit? No, you guys asked me for notes. You guys asked me for notes this morning. I had to, like, literally sit down and write you notes myself.

38:54Yeah, we didn't use that name up. Yeah, exactly. I don't even know what I wrote to you. Wait, what are you going to say, Sean? I DM'd him this morning, and I was just like, hey, saw that, you know, whatever. Excited for the pod today. And I was like, you know, the best episodes tend to be where the guests come in with, you know these three or four bullet points i gave him some guidelines like you know i was like no i said uh i noticed you hadn't filled out the prep doc we usually send a guest like a prep doc and they fill it out and then it gives us kind of like a you know some options of where you can go in the conversation and he goes prep doc dude let's just hang and i was like oh yeah oh i gotta be i gotta be cool okay my bad uh yeah so so i mean i had i have a team of people that help me with things like what i'm preparing for but no this is me there's no notes there's no but you should like I actually heard a couple of stories recently that have really inspired me.

39:40Okay, let me give you a little like – There's a framework that I think most people underestimate. Okay, so there's a story in sports that LeBron James spends a million dollars a year on his body. The numbers is actually kind of irrelevant, but the idea is directionally correct. LeBron James spends a lot of money on his body, and he has certain treatments and coaches and protocols that he follows that the average athlete is not following. In fact, we went to an NBA team, and I said, how many of you guys have chefs? and less than half of that team in the NBA raised their hand. I was like, this is insane.

40:10I couldn't believe the owner would even allow that. But like for LeBron, every meal is dialed. Every hour of the day is either recovery, it's building, or it's playing. And so LeBron does that in his field. I then talked to somebody who knows Peter Thiel very well. And I go, you know, it's weird because Peter, he's not like a smooth talker, right? He's actually like stutters a bunch, he stumbles. but when Peter Thiel goes on tour and he does it like every you know seven to ten years he's got this message and boom he'll get like a ton of PR his message is very effective so he's not very efficient with those words but he's very effective and you know if you remember he did one where it was uh universities are a bubble yeah right he went on a whole tour of that and then he launched the Thiel Fellowship underneath it and he did one which was competition is for losers and he has these like slogans almost like marketing slogans that come just for losers then he launched zero to one his book that was all about how to build a monopoly and he did one with when trump first ran and he was like you know and for founders one they had we wanted flying cars but all we got was 140 characters yeah now peter did not write that line in fact what my friend told me is that peter actually kind of like has a guy who follows him around that's listening to all peter's thoughts and then sort of workshopping his bits like a comedian would like a like a politician speech writers would and they actually like craft the message and they write it out and they basically get him prepped for media he's not showing up and just winging it and because maybe he's not that great at winging it uh david rubenstein does the same thing that you know i i know david david actually has a even a larger team because he does the show and he does the tv show when he obviously with carla and stuff so i don't necessarily have a writer per se i do have people that kind of remind me of like hey like remember that like this is kind of the direction i'll give you the best example earnings calls i meet with my my jeff hoffmeister amazing amazing amazing CFO.

41:56I met with Jeff and our IR team. And I'm like, all right, what are the three or four things that like that we want to we want to say? And I basically take it and I, you know, heart hardly arise it. I make it sound like me. So can you give an example? So an example is like we want to get we want to be on Roblox or something on the Roblox thing. It's really about the fact that Shopify is no longer an e-commerce company or the commerce everywhere company. OK, right. And that's what's important. So I'm using Roblox as effectively a proxy for explaining that you may not necessarily, you know, want to sell in Roblox if you're selling hand sanitizer.

42:26But if you, if you're selling another product and your audience spends time in Roblox or, or in some sort of in a metaverse, you may want to access it by being on Shopify. You are default selling everywhere. Right, right. The story isn't we're on Roblox. The story is we're now the e-commerce and we're now the commerce everywhere. We're also on Pinterest and Instagram. There's, there's literally a Spotify, a Shopify for Spotify channel, where you can actually, if you're, if you had large, if you're Beyonce and you have an artist profile, like the size of Beyonce, you can sell sacred, which is our cosmetic line on Shopify inside of her artist profile.

42:56And rumors are you're going to be on ChatGPT. That's rumors, yeah. We're not going to go there today, but exactly. We want to be wherever you effectively have consumers. So earnings was three weeks ago, and I love earnings. I go, I do my earnings call. I then do my analyst calls, and then I do my media tour. In this case, I did TBTN, which I think those guys are killing it. I did CNBC. I did some Bloomberg stuff. I noticed that there were a bunch of other companies that, because I listened to earnings calls a couple days before and a couple of days after just to kind of hear the tonality of the reporters and the journalists, but also of the executives.

43:30And Sebastian from, I think, is it Klarna or something? He basically came out, I think it was Sebastian. And he said, hey, I, after his earnings call, the whole thing was done by AI. That actually was, it wasn't even him. It was basically an AI emulating his voice. And that's who did his earnings call. And it made a splash. There were a couple articles about it. And so I listened to it. I was like, yeah, like, that's like a five out of 10. And maybe you can say it's a six or seven out of 10 because he saved a lot of time and so is effective. But there was zero, in my view, there was zero personality to it.

44:01And then I watched a bunch of other kind of professional executives that did their earnings calls, like the P &G guys, for example, or the folks over at Best Buy. And I listened to their earnings calls. And I'm like, yeah, they sound like they're reading a script. If you go back, you don't have to do this, but if you go back and listen to Shopify's earnings calls, You'll hear things like, okay, I know what I just said, and I know you think that's surprising. I'm going to repeat it again because it's really important. And I'll use voice inflection. Nice. And I'll use repetition. And it doesn't – and what I hear back from – It's like theater.

44:30What I hear back from both analysts and investors is that they find our earnings calls to be so much more interesting because what they actually hear is our personality. They hear the passion in my voice for we give a shit about this stuff too. And so I think that there's probably a right balance where you have people around you that are giving you sort of the macro things. But like if I start talking like Peter Thiel, it's not authentic and therefore I don't think it'll be as effective. And so I think there's a balance that I'm trying to find. And so I've done 40 earnings calls now. The balance I have is tell me what are the most important things that we need to hit.

45:05And then let me kind of find my own way of negotiating it into the call. Right. I like that you like studied the game film of the other earnings calls. That was what I was looking for. That like kind of that extra that you go to that others may not. There are people that, I mean, Benioff's fantastic at it. Do you, so Toby came out with this like memo that was like, hey, it is a baseline expectation. He didn't come out with it. It was leaked, but yes. Yeah. It was leaked. Someone leaked it. I always assume those are like intentionally leaked. I would have intentionally leaked that if I was him.

45:32I think in hindsight, some of those things, when they do get leaked, you're like, you know, for better for worse kind of thing. But yes. But the point is in it, he was basically like, you know, AI is an expectation based on expectation. You got to learn these tools. The way to the way to get good at them is to use them a bunch. And you got to start solving problems using this was the general general ethos. I'm curious, you personally, Harley, day to day, what's your AI usage? Are you like, you know, a lot, a little just chat GPT, other tools? Like, what are you actually personally just using either professionally or personally in your personal life?

46:02Two things. One is I mean, I use chat GPT. I really like the fact that now it's like, I like the history side of it. So for example, like back to sort of longevity, every time I get a blood test, I uploaded a chat GBT in a folder called longevity and health. And so now I can ask questions. Although I do find if I say like, I had a blood test last week, I uploaded a new one. I said, compare this to my last one. And it compared it to one from three, like, like a long time ago. And I was able to spot it. So it's not a hundred percent, but I like using that quite a bit too. I gave a keynote summit last week.

46:33I literally fed my entire keynote script into chat dbt and I said hey and what parts of these do you think are confusing if any like where am I where am I losing the thread here so I think that I use chat dbt and particularly o3 um the o3 model on a daily basis sort of like you know on my like I have two screens here so basically my screen next to me I always have that open I really like Claude for other projects so for investing for example um you know my wife and I do a little bit of investing. We own some apartment buildings. So I have a file for real estate, which is every time I get an update from the property management company, I feed it.

47:09And I find Claude is much better for analyzing existing documents. I find that ChatGPT is much better for sort of reaching out into the public sphere, like the web and bringing things in together. Those are the two I use the most. And then back to sort of the earnings calls, one of the things we did was we basically made all of Shopify legible and we built like about a dozen MCPs inside of Shopify. so usually in preparation for an earnings call i will go to let's say i want to talk about like shop like capital i'll go um let's say i want to talk about like we launched it in the uk so let's say i want to go i want to talk about that in the earnings call i'll go to the capital leader and say hey give me a couple of the highlights for uk it's a new one for us i want to talk about how it's going this time i just went to the vault and literally went into like cap the capital program because everything is legible i was able to pull most of the data on my own the personal jury jury still out whether or not I'm missing.

47:59Cause when I talk to the leader of capital, I get some of the nuances and I'm like, Oh, you just said this sort of thing. And like, I actually, I'm going to take that and run with that, even though it wasn't, you didn't intentionally mean to leak it to me or tell it to me. Whereas using basically like the Shopify vault, which is where we, I'm able to access all this data through the MCPs. I find that I'm basically getting a lot of headline stuff, but I do want to make one point. One of the things that got missed on Toby's, on Toby's memo now, or the email now is that there was a term he used that I'm surprised more people haven't picked up on, which is like AI, like being reflexive.

48:33And part of what he's trying to get the company to do is to be reflexive about the usage of AI so that rather than sort of make it a sort of, I have a project and now like I'm working on my own. Oh, you know what? I should also use AI and see what I can get from ChatGPT or Claude or Anthropic or something like that or complexity. This idea of making it reflexively part of our day-to-day work is really what he was trying to do. And in fact, so much so that he created this, like this new friction, which is before you can go and hire someone on your team, you first have to substantiate to Shopify, to the hiring manager, to the talent team, why AI cannot do it better.

49:08And one of the things we're noticing there is by actually creating this like friction of saying like, before you go and hire, you must first do it. What ends up happening is people by the end of substantiating why they need to hire someone that AI can't do, realize that they actually should have, that AI can do a bunch of that as well. That is very different than what you're hearing, I think, in most companies, which is, let's just use AI as part of our, you know, if I have to design something in Figma or in Canva, I'm going to use AI to help with that. This idea of it being reflexive is sort of what we're trying to do.

49:34I like that a lot. That's cool. That's a great little nuance and sort of tactic. You know, I like these sort of either incentives or systems where you do one thing, but it has all these downstream impacts. Like right now people are talking about the U S like, Oh, we have the deficit. So crazy. And Buffett has always said this thing. He's like, Oh, simple. I could solve the deficit in two minutes. Here you go. If we run a deficit over 3%, nobody gets to keep their job in Congress. That's right. Watch, watch what happens. I mean, that is, you get to do that at companies. I mean, back to like the phase of the company at the phase of size and scale of our company, we get to do stuff at this crazy scale.

50:10So simply by adding, you know, a simple friction on hiring that says first substantiate it, you actually see incredible results and you can evaluate. You can literally say like, okay, well, how has hiring changed since that email was leaked? How has hiring changed since we added that friction thing? It's very difficult to actually see the efficacy of all these things when you're 10 people. Hey, quick message here because you know that feeling when you send a wire and it actually works? No friction? Well, I've used Mercury for years now and let me tell you, it just works. And that's why I use it for not one, not two, but eight of my companies.

50:43From credit cards to invoices, I have everything in one place. There's no janky dashboard. I'm never told, please visit a local bank branch. None of that tomfoolery. And a few months ago, I landed a big client. The first thing I did, I sent them a clean branded invoice. Boom, deal closed, cash in the door. That's the kind of banking experience I want. And that's why I use Mercury. So if you're running a startup and you want banking that feels like it's built in this century, well, go to mercury.com and get started in minutes. Mercury is a financial technology company, not a bank. Bank services are provided through Choice Financial Group, column A, and Evolve Bank and Trust members, FDIC.

51:18Well, you look really healthy and you have a lot of energy. I'm curious. You said you got curious and kind of interested in biohacking slash longevity. You're on a kick right now. What's got your interest? What have you, what are you doing? That's maybe you feel is, is either interesting or working for you or you're enjoying it. Just give us kind of like a quick health dump. So I sort of divide into two buckets, which is like, I'm going to die of one of two ways. I'm going to either die because of cancer or I'm going to die because of heart attack. And so the cancer thing, it's not easy, but prenova does a lot of that heavy lifting for me, or at least I'm 41 now.

51:48So I'm now getting to the point where I'm taking it a lot more seriously. So once a year, and prenova's not the only one. I like it a lot. I like it so much that I actually invested in the company. My wife and I invested in the company a couple of years ago. I think the way they do it, I think the way the technology is moving, the fact that here's a very simple thing. A lot of people don't like going to these full body MRIs because they get claustrophobic. so a small you know um i guess part of the product of prenova is you put on these glasses that have these mirrors and the mirrors go backwards into a screen and i watched like the most you know fun loving light show that i can find for me that's seinfeld so i'm also some i'm not claustrophobic but i don't i don't i don't want to stay in something like that for a long time dude when i went in i watched top gun i was like oh what's a movie i should have watched but i never did i just watched i mean top gun yeah i did the i'm like i do not want to be stressed out i don't want to be scared dude i watched a zodiac killer documentary on netflix it was great you i mean that speaks volumes about your both your personalities um i watched like seinfeld personality test and so so i so that sort of takes you on the cancer side on the cardiovascular stuff i'm i just did clearly a clearly scan which basically looks at blockages so what i'm trying to do what i did initially was i just got a baseline of like where am i at right now the reason i like prenova each year is because i basically can look over time how things are changing if i have like a benign cyst on my on my liver is a growing year over year now at least i can monitor that stuff too so to me those are the two main buckets um and then i just try to do these like um these misogies is like one thing every year that scares the shit out of me and the thing i really like right now is called 29 0 29 and jesse isler jesse isler's thing jesse's uh he's done an amazing job him and mark who's his partner co-founder they've created this incredible thing that effectively allows you to climb Everest, but you can do it from like Colorado.

53:35In my case, I do it in Quebec. I do it in Mont Tremblant. You can do it in Vermont, but they created this incredible thing that allows you not to have to travel to Everest, not Everest, and you actually can do it. And so I've been doing this, this was my second year doing it. And I, and I like doing it, not just because of the like high five, it's cool to, to, to climb, to emulate climbing Everest, but I like the idea of getting really scared that I'm going to fail at it. And therefore I train much harder. And so my workouts actually are much better because i'm so scared of failing at this 29 29 thing yeah yeah dude how many uh last question how many um how many companies in the world are bigger than shopify you guys are worth uh it looks like 153 today or something or once whatever 130 you've been as high 134 200 something down by 20 billion dollars just one of it's casual what's crazy is like You're worth$134.56 billion.

54:28Like change that 5.6 to like a 5.5 and like that's like life changing. You know what I mean? It's crazy for sure. Let me one more call it for if you were listening to this and you are a company that actually like, you know, you understand your business well. You see great growth potential. Like this idea of avoiding the public markets is insanely silly to me. It's been an incredible 40 quarters in now. It's been like an incredible journey for us. It makes us a better company. It allows, I think, the people that use Shopify find more confidence. I mean, now we have companies like Hunter Douglas and Mattel and Birkenstocks using Shopify.

55:02I think one of the things they love about it as a product is that being publicly traded provides some sense of stability. Well, what I was going to say was I looked it up on ChatGPT. So there are probably 120 companies in the world bigger than you, which means of all the companies that have ever been started, of all the companies that are out there right now, and probably in the history, given that like today's companies are bigger than everyone else, you are in like the top 150. It's pretty astounding. And I think that like, if there was a ratio of like somehow most relatable or like for some reason when I talk to you, I'm like, he's just one of us.

55:38He's like one of us almost. That's why we're friends. Fuck, he's not one of us, damn it. And then I like see this, and then I see the stats and I'm like, he's so good at his job that he's tricked me into thinking that he's relatable. you know me personally we've like i think i said this at the beginning right i i was guest 118 we are not the same my friend we are not we are the same and now you've had over 750 of them we are we are not the same and and but if there were a ratio of like i feel like i could do whatever he's done to approachability to market cap ratio you are you get the gold medal i think that's the sweetest thing you've ever said to me sam you know you know what's one of the best things I did after that first podcast is basically every year for the last five years, I take about 20 % of whatever my profits are out of my Shopify store and I just buy Shopify stock.

56:26And that alone I think has compounded as good or better as my actual econ brand because now my earnings are growing. Whereas like if I just reinvested it in the business, not every business you can reinvest 100 % of your profits back into. And so just that one little habit has been very, very helpful for Well, that means a lot to me. It's actually cruelly neat. We're doing this thing called Chocolate Milestones. Basically, it's our version of the Emmys or the Oscars for actors or the Grammys for musicians. We give these milestone awards. You guys have probably seen them around. This is the 10 ,000 one.

56:58So we've given them for 10 ,000 orders, 100 ,000, and a million orders. Dude, I got a bone to pick. Y 'all are so slow. I got my milestone, but I'm already on the next order of magnitude. Perfect. It's so slow how you guys set these out. I mean, these are heavy. We had to ship them out and stuff. There's a lot of people. But anyways, so I deliver a bunch of milestones in person. That's your excuse. so you need to get to a million first and i'll deliver your million one sean but i meet these people when i deliver them and often what i hear is not only like obviously they built their business on shopify but many of them you know like they they're they're also shareholders which i think is an unbelievable endorsement as like you know it's one thing to use the product and build your business on it but then also to invest your you know your your hard-earned money into to be clear not an endorsement just a recovery of fees is what i was looking for i said okay I'm paying you guys this money.

57:43I'm going to get it back in a different way. You made it sound way less romantic than I did. Yeah, exactly. Let's be real here. Dude, thanks for coming on, man. Dude, this is great. You guys are the best. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.

58:07All right, this episode is brought to you by Mercury. They are the finance platform of choice for over 200 ,000 companies. Shouldn't be surprised because I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of. And then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive. And you could tell that it's actually made by a startup founder.

58:34It's an entrepreneur. You could tell it's made by somebody who used other banking products in the past. and didn't like all the different rough edges and annoyances and decided to, you know, actually fix it himself. And really any type of entrepreneur you are, let's say you're an agency. Well, one of the things every agency has to do is be able to send invoices, easily create them, send them to customers and stay current on your balances with all your customers. Well, you can do that inside Mercury. And so I think that Mercury is great. Highly recommend you check it out. And thank you for sponsoring the show.

59:00For more information, check out mercury.com. Mercury is a financial technology company, not a bank. Check show notes for details.