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

Episode 715: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to Harley Finkelstein ( https://x.com/harleyf ) about boring products that could be worth $100M. — Show Notes: (0:00) Disrupting boring products (15:05) Swiss Army knife founders (21:42) "People only remember your weird" (31:45) Considering an exit (39:32) Becoming a better storyteller (46:17) Shopify's leaked memo about AI (51:26) Biohacking Longevity — Links: • Shopify - https://shopify.com/ • Touchland - https://touchland.com/ • Firebelly Tea - https://firebellytea.com/ • Ember Mug - https://ember.com/ • David’s Tea - https://davidstea.com/ • AG1 - https://drinkag1.com/ • Method - https://www.methodhome.com/ • Olly - https://www.olly.com/ • Welly - https://www.getwelly.com/ • Ritual - https://ritual.com/ • Seed - https://seed.com/ • Prose - https://prose.com/ • Prenuvo - https://www.prenuvo.com/ • CLEERLY - https://cleerlyhealth.com/ • 29029 - https://29029everesting.com/ — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N. A., and Evolve Bank & Trust, Members FDIC — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano

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

• 0:00Shaan Puri?

  This is serious podcasting over here.

• 0:02Speaker 01

  Sean, the last time I did this, actually, I literally pulled up the data that it was in 2020. I think you were in like a wife beater and then you went to the bathroom and I heard you flush the toilet. I'm serious, dude. That's how far we've come here.

• 0:18Shaan Puri?

  Hey, we haven't come that far. These things that still might be, it might happen today.

• 0:32Shaan Puri?

  I have a Shopify crazy business story for you guys. Go to your internet browser real quick and go to touchland.com. Harley, you might know Touchland.

• 0:40Speaker 01

  Oh yeah, of course. I, in fact, I've given out them as like at events. But their headline doesn't make sense. It's sensory essentials that bring delight to everyday moments of care. Is that? It's hand sanitizer. Perfume?

• 0:52Shaan Puri?

  Yeah, it's hand sanitizer.

• 0:56Shaan Puri?

  So here, check this out. This story is pretty crazy. This person starts out, she's distributing like hand sanitizer in Africa where, you know, like sanitation is super important. People get really sick because you know, they don't have clean water to be doing blah, blah, blah. And she, she gets this idea, like, what if I made hand sanitizer sexy? Because at the time.

• 1:17Speaker 01

  Yeah, it was all like Purell.

• 1:19Shaan Puri?

  Exactly. And if you, if you think about Purell, Sam, what is it, what does it smell like?

• 1:24Speaker 01

  Alcohol. It's like something you get at the hospital or a teacher, from a teacher.

• 1:27Shaan Puri?

  Exactly. Horrible smell. It smells like tequila. Uh, the form factor is not like, nothing, nothing to brag about, nothing to show off. It was a very pure utility product. And what she did was she just reimagined it basically as a luxury product. So she took hand sanitizer. She was like, I'm gonna make it smell good. I'm gonna make it look good. I don't know if you've seen the like, the cases of it. It's basically like.

• 1:48Speaker 01

  Yeah, it's beautiful. It, it's like this, like, sort of, um, like, almost Johnny Ive designed, like.

• 1:54Shaan Puri?

  Exactly. Exactly. If, if Apple decided to like go into the hand sanitizer market.

• 1:58Speaker 01

  And she'll see collaborations, right? Like Hello Kitty, Disney. I mean, this is like a whole different level of, of, of vision around hand sanitizer.

• 2:07Shaan Puri?

  So she, she comes up with this idea. She goes on Kickstarter and she raises like $67,000. She's like, okay, great. $67,000. I can do a first run. First year, I think she does like a million dollars in sales. Covid happens and obviously people care about hand sanitizer way more during Covid. Business just explodes. Recently, this is now 2025.

• 2:30Shaan Puri?

  It was just acquired for $880 million, this hand sanitizer company. And I love this story.

• 2:37Speaker 01

  It says it was gonna do, this year's gonna do 130 million in revenue and 55 million dollars in EBITDA.

• 2:43Sam Parr?

  Wow.

• 2:43Shaan Puri?

  Exactly.

• 2:44Sam Parr?

  Incredible.

• 2:45Shaan Puri?

  And they're on Shopify. There you go, Harley. There's your plug.

• 2:47Speaker 01

  Well, thank you. Thank you for plugging Shopify.

• 2:49Shaan Puri?

  But dude, isn't this a crazy story? And how cool is this? Basically, this, this concept of like, how do you take an ugly thing, or like just a commodity, utility, utilitarian product, but then apply like high fashion to it, apply luxury to it, and create your own category? You know, it, it sells for more, it's, it's the only hand sanitizer people gift to each other? Like you were saying, you gift it, my wife saw it, and she's like, oh, I just got that as a gift for like our kid's teacher on their last day of school. You would never like gift Purell to somebody unless you're trying to tell them something.

• 3:20Speaker 01

  I have a, you know, one of the cool, so we have a few million stores on Shopify. We're about 12% of all like US e-commerce right now. One of the things that I'm seeing a lot of right now are these, what I think would be considered to be fairly, you know, this is gonna have a majority, but it's not like boring products becoming very sexy. And then, I don't know if you guys saw this, but like literally a week ago, Dyson came out with this thing called the Pencil Vac. Have you guys seen this?

• 3:42Sam Parr?

  Yeah.

• 3:43Speaker 01

  Anyways, like, so Dyson, like the guy, the man, the founder, he actually did like this press conference. It's on YouTube now. I just checked.

• 3:50Sam Parr?

  He's amazing. Have you guys read him?

• 3:51Speaker 01

  He's totally amazing.

• 3:52Shaan Puri?

  Isn't it like a seven minute demo and he just came and dropped the mic on with like epic vacuum?

• 3:56Speaker 01

  I think it's even less than, it's like five minutes, but yeah, exactly. But, but there's like millions of views on this demo for a fucking vacuum cleaner. And actually, what I thought about it, like, one, he, he's been, Dyson's not a new company. They've been around for a very long time. But like this idea that he took something fairly boring, made it way better, and now he's able to actually leverage modern media like YouTube to actually tell a story. I bet a bunch of people like are actually gonna buy their first Dyson product because of this video that never did before.

• 4:22Sam Parr?

  Have you guys ever read about him? Sean, have you read about James Dyson?

• 4:24Shaan Puri?

  Dude, you and David Senna won't stop talking about James Dyson.

• 4:28Sam Parr?

  Dude, like I, I started reading his book. He's just like the man, but he's basically, it sounds ridiculous. He's Steve Jobs of vacuums. He was Steve Jobs before Steve Jobs, but he was like, he's like this type of person where he's like, the inside wiring needs to be beautiful. He's like that type of guy, but he took, I'm really interested in this idea of people who take non-serious things very serious. So vacuum, hand dryers, whatever. And I think it's so freaking cool. And he is like that type of guy where he was like building the first prototype for like two or three years to the point where he was, I think he went bankrupt, but he still kind of kept at it.

• 5:00Speaker 01

  Amazing. But you could sort of look at across a bunch of different, like I'm having my coffee now, like my Ember mug, right? Like this idea of adding a small heater to a mug, I think is like, seems kind of boring. Ember is a great Shopify store. So I've been following them since pretty much day one. I mean, that's a huge company now, both in wholesale, but also

• 5:18Sam Parr?

  Is it really? That's one of those ideas that I thought that was silly.

• 5:21Speaker 01

  Harley, just go ahead and log in and just start reading out all the numbers for these brands. I'm not gonna do anything like that. But what I will say, there's, you know, actually, let me, let me show you. I'm gonna give me one second. You guys know my best friend, David Siegel. I think you've had him on the show. Standard of David's teas, made, you know, took his company public. He's awesome. Many hundreds of millions of dollars. Him and I have this like tea business on the side. We started during the pandemic called Fire Belly Tea. Anyways, like we tinker like you guys do on weekends. We had this idea, it's literally, I'm showing you a prototype right here. You can kind of see it. It is literally like our way. We think that DuraFlame needs to be disrupted. That's a great idea. So like we literally created a company. You talked about this last time you were on the podcast. Exactly. So we had this idea in 2020. And actually, so now David and I have, we have a working prototype. It's actually, you can read it. It's literally made from Canadian softwood. It's 100% kiln dried. That's a great idea.

• 6:05Speaker 01

  We have branding. It's called Flint, which we think is a cool name for it. But you look across all these different categories of things that most of us as consumers take for granted. And there's always this like 10x version of it. I like, my wife's really into, she could hate me saying this. She's really into karaoke. Have you ever gone and tried to buy a karaoke machine? There are companies that rent them to you because they're so big and clunky. Like, someone should go and like disrupt the karaoke machine business. Like that to me is, is such a brilliant idea. Or, you know, tools, like you move into a new house and you kind of need like, you know, random tools. Most of these tool companies you buy like at, you know, Home Depot, they're clunking, don't look good. There's actually a couple like beautifully designed, almost, almost like the Touchland version of tools selling on Shopify. People

• 6:49Speaker 01

  misunderstand TAM to their detriment, total addressable market. Everyone kind of looks at TAM as being this thing which is like, what is the, like, there's a pie and I'm gonna take a bigger piece of the pie.

• 6:59Sam Parr?

  Like it's a, it's a static number.

• 7:01Speaker 01

  Yeah, it's very much like zero sum. And funny enough, you know, Sequoia has said this publicly, so I think I can say it now, but like the reason Sequoia did invest in Shopify 15, 16 years ago was they looked at the TAM of retail SMBs on the planet and they effectively forecasted if Shopify would have a meaningful percentage of that market, how big of a company we could be. What they missed was that, that we're actually going to pie itself, right? This like, this positive sum that someone who's starting, you know, I don't know the person behind Touchland, Sean, but presumably like this person didn't necessarily, like she wasn't in or he wasn't in this industry previously. Maybe it wasn't even entrepreneur previously.

• 7:40Sam Parr?

  But is that the story you told yourself when you were doing it? Because when you're doing it, I mean, you guys.

• 7:44Speaker 01

  No, of course you can't. That's the, you almost cannot do it. You actually have to almost imagine like, you know, let's just use Flint for a second. By the way, this is not for sale yet, like this is just a prototype, so you can't go buy it. But let's just, like you, what you would do for Flint is you'd say, okay, what is the, what are the products in the market? The biggest one is DuraFlame. How much does DuraFlame sell a year?

• 8:03Sam Parr?

  What's the answer of that?

• 8:04Speaker 01

  You know, I think it's something, I think it's like, we, last time we chatted was like half a billion dollars. And it was like Home Depot, Lowe's, these sort of home hardware stores. But then one of the things David and I were thinking about is like, why are these not sold in convenience stores, right? Like, why do I have to go to Home Depot for it? Why, if I'm picking up like my weekend beer at a bodega or a 7-Eleven, I should also pick up my, my Flint as well. So what you, you have to almost do as an entrepreneur is you really have to kind of like broaden out the horizon of like, what is the potential? Kat Cole and I were just speaking last week. Kat Cole, who's the CEO of AG1, they're doing $600 million a year with AG1 with one single SKU. There is no way, Chris is the founder of AG1, there's no way that Chris thought about that, like, you know, like,

• 8:48Speaker 01

  basically, they didn't just grow their, their piece of the pie, they grew the pie in, like infinitely. And I think that's, those are the best entrepreneurs for me.

• 8:57Sam Parr?

  Have you guys heard, Sean, did you ever meet Eric Ryan? I think he spoke at the HustleCon that you spoke at.

• 9:02Shaan Puri?

  I didn't meet him, but I, um, no, you never invited me to speak at HustleCon. I was just an attendee, but I did attend the one with Eric Ryan.

• 9:08Sam Parr?

  I also was invited to speak at HustleCon, just to say the thing.

• 9:10Shaan Puri?

  Yeah, and we've actually decided to create our own called Super HustleCon.

• 9:14Sam Parr?

  Yeah, Harley and Sean does.

• 9:16Shaan Puri?

  For people who actually hustle harder than the people on HustleCon.

• 9:18Sam Parr?

  Yeah, instead of, just chill on that.

• 9:20Speaker 01

  We're the opposite.

• 9:22Shaan Puri?

  Yeah, exactly. But yeah, I remember him speaking and he was brilliant. So for people who don't know, Eric Ryan, he did what? Method soap. So he basically went into a boring soap category and made it sexy and made it like, kept ingredients you understand on the back of the bottle. That was like the big trend at the time.

• 9:38Speaker 01

  But the bottle was like pretty.

• 9:40Shaan Puri?

  The bottle was pretty and the photography was pretty. Like, they would do like a photo shoot instead of it being like, you know, those pharmaceutical commercials where they show cartoon germ and he's getting sprayed? It was like two really hot people who are like, kind of like dating, but they haven't really defined their relationship yet, but they're cleaning up their house together. And like, that's what the, that was the photography on the website.

• 9:59Speaker 01

  Well, Moiz did that too, right? Moiz did that with Native and sold for a hundred million dollars to Procter and Gamble.

• 10:03Sam Parr?

  Yes, Eric actually did it with Ollie Vitamins. He also did it with Welly Band-Aids. And he has a new thing that he's doing it with, but I don't know what the new thing is.

• 10:12Speaker 01

  I mean, I have like, like, you look at, just shop it. You look at Ritual, Ritual Vitamins, or Seed, which is probiotics. There's a company that I think is really cool. They're called Prose, P-R-O-S-E. They do personalized shampoo based on hair type. They're doing about a hundred million, this is public information, they put it out there. Hundred million dollars in annual revenue, 80% of his recurring customers. So you basically like, send them a follicle of hair, they analyze and they send you a shampoo specific for what you need. I think like that personalization stuff for shampoo, even, obviously like, I don't know if you guys take supplements, I take like eight a day. I wish, you know, I can basically just take one pill that has exactly what I need specifically for me.

• 10:49Sam Parr?

  Do those eight a day actually do anything?

• 10:52Speaker 01

  It's a little bit of, of... You know, correlation versus causation. My, all of my lipids are getting better. And I think there's definitely some correlation to it. Although, as part of my taking all these supplements, I'm also working out more and I'm eating much better. And I'm drinking far less, you know, red, red wine with, with, on weekends. And so I can't necessarily draw a direct, you know, causality to it. But certainly I do think that, and, and honestly, it's not that big of an inconvenience. If it helps me by 5% or 10%, I'll do it. Um, I'm also, I, I do every, every year for my birthday, I do something called prenova. Do you guys know prenova? Yeah. I love prenova. I've been doing it since I was, uh, for the last six years, every, uh, my birthday's in November, every year.

• 11:33Shaan Puri?

  That could make for a, a pretty bad birthday one year. Uh, you gotta be careful with that.

• 11:37Speaker 01

  Totally. I mean, that's, the, the issue with that, the, the issue with that is obviously false, false positives. Which I have just decided, I think entrepreneurs and founders tend to be on, on this side of the, of the equation. Which is, I prefer a false positive than a false negative. Right.

• 11:51Sam Parr?

  Have you, maybe you could answer this. You're, you're actually the only person I've asked this publicly, uh, but I've never got a good answer. How can you be a billionaire today and be unhealthy? Like, how can you be a fat billionaire today?

• 12:02Speaker 01

  I would, I would, I would get rid of the billionaire. I think, um, if you are, if, if, forget the billionaire thing for a second, because I don't think that, you don't need to be a billionaire to do that.

• 12:10Sam Parr?

  Do you know any fat billionaires?

• 12:12Speaker 01

  I, I do, but I don't want to say anyone's name right now.

• 12:14Sam Parr?

  Of course.

• 12:14Speaker 01

  You, you probably know them also. Uh, but I, I, I, maybe, maybe they're a thyroid issue. I do believe that if you have the means and you can have, you know, uh, if you can have like house, you know, housekeepers, for example. Or you can have a chef at home. It's like, if you have a chef at home, no one's going to their chef and saying, make me super unhealthy food. Usually if you hire a chef, you say, I want to eat really well. Here's what I really like. Um, so there's almost no excuse. Same with a personal trainer. It is very difficult to go to the gym. It is much easier to go to, you know, the gym if you have a trainer waiting for you that you're paying for you. Or someone showing up at your house. So I do think that it's easier for you to be in better shape if you have means.

• 12:54Shaan Puri?

  See, this is why I'm an outlier. I defy all the rules.

• 12:57Speaker 01

  Why?

• 12:58Shaan Puri?

  I have a chef, I have a personal trainer who comes to my house.

• 12:59Speaker 01

  Okay.

• 13:00Shaan Puri?

  I'll find a way. The, the, the will finds a way.

• 13:04Speaker 01

  But Sean, that's bullshit.

• 13:05Shaan Puri?

  If I want to DoorDash something, I'll find a way.

• 13:07Speaker 01

  So if you didn't have the trainer come to the house, you'd be in way, I suspect you'd be way worse off.

• 13:12Sam Parr?

  Yeah, and also you have gotten way healthier over the last handful of years.

• 13:14Speaker 01

  That's right, yeah. You know, when I had my first child, Bailey is now, my daughter's eight, when I had my first child. So Dave Siegel, again, bringing it up again, like Dave's a couple of years older than me. He's had kids before I did. He basically said to me when I was having Bailey, he's like, look, if you can afford to have a nanny. He actually described articulated as, he said, it's going to be a marriage saver. And I didn't really understand what it meant. And what he meant was like, just everything, everything is easier. As a new parent at home, I was, you know, Shopify was already publicly traded. I work 70 hours a week. He's like, just if you can afford a nanny, you should do this. And I didn't really know what he meant by the whole, it's a marriage saver. In hindsight, I now do because like some of the stresses that I think some people have, you just, they don't go away. They're just less, you lessen them when you have certain like luxuries in your life.

• 13:59Speaker 01

  And I don't, I do, I mean, I grew up without money, so I didn't grow up in that, in that world. I don't take that for granted, but I do see how it gets, these things, these things get easier.

• 14:08Sam Parr?

  I heard an interesting story about, actually last week, I was with a person I'm not going to name, but he's like, he's a billionaire and he's in, he's a big time investor. And he was telling stories about how he, we were talking about Shopify. I was actually talking about how I met with, met with you. And I was like, man, Harley's so charismatic. Like it totally got me bought into Shopify even more. And he was saying, he's like, yeah, man, I've met with Harley a bunch of times. I know him well. I've met with Toby a bunch of times. He goes, and I've actually met with Stripe a bunch of times, the Collison Brothers. And they're an amazing company. And he was like, I think they're roughly worth the same right now. But he was like, I think Shopify is going to be worth 10 times more than Stripe. And I was like, why?

• 14:49Sam Parr?

  And he said, whenever I'm with the Collison Brothers, we talk all about like interesting philosophical things and like what their hobbies are and things like that. And whenever I'm with Toby, the only thing he ever talks to me about is Shopify. That's all he ever wants to talk about. He won't, he will only talk about Shopify. And because of that, I think that obsession, even when your company is worth $150 billion or whatever it is, that still comes into play. It's not just market factors or the market forces.

• 15:14Speaker 01

  This is the beauty of this founder led thing. I mean, I, you know, I think the Collison Brothers obviously are this great example of founder led as well. They're obviously private, so you don't know the exact valuation of it. But I do think that this, this era of founder led companies, people that just really give a shit. There's no way to replicate that or to emulate the give a shit.

• 15:32Sam Parr?

  And I don't want to like, I actually wanted to spend some of the time episode where I was like, actually Harley, I like, I know you a bit now, but like Toby is like, he's still mysterious to me because I've never met him. But he seems like, like I think he has this one quote where he goes, "My wife says I'm an immigrant to the human condition."

• 15:48Speaker 01

  That sounds, that seems super, I mean, and to his credit, because he is so self-aware, he truly like, he's incredibly self-aware. He knows what he's really good at. And that's, if you think about Shopify, I think I said this at Sam when we were meeting, but like, you think of the phases of companies, like at the beginning of the first phase of a company, everyone needs to be a Swiss Army knife, like everyone do everything. And then the second phase, it's like more like what I call like triple threat phase where like.

• 16:12Sam Parr?

  Is there like a, could you put a threshold onto that, like a number of people or something?

• 16:15Speaker 01

  Yeah, I would say like, for us, it was like zero to, I don't know, Dunbar's number, you know that concept Dunbar's number?

• 16:21Sam Parr?

  Fifty or 150?

• 16:22Speaker 01

  Yeah, I think it's 150, something like that, which is like, comes from tribal times where that's how many people any human can remember at any one given time. So I would say like zero to like 150 or so, it's like that, you know, Swiss Army knife. In those days at Shopify, I did BD, I did sales, support, partnership, I built the App Store and partnerships program. I was also the lawyer. I mean, I was a general counsel, I wasn't really a good lawyer. I'd only practiced for a few months, but.

• 16:46Sam Parr?

  Better call Saul.

• 16:47Speaker 01

  Yeah, I didn't, I didn't have a, we didn't have a CFO at the time or anything like that. So it's like Swiss Army knife time. And then I think eventually you can almost market for us around like the series A or series B, where now like we're more people. People can sort of slot into the right roles, meaning like you don't do one thing, but you do a couple of things real quite, quite well. That was sort of, I was chief operating officer. And so I looked after a couple of big organizations. We built a sales organization. We began to think about just different areas of product. Post pandemic, so like 2021, 22, a couple of things had to change for us. One is we were, we were, we were bloated. We had like 14,000 people. That didn't work. We brought it down to what we are now, which is around 8,000 people.

• 17:27Speaker 01

  And we, we quite like our size right now. We had a couple of businesses that were not the right business for us to be in. One of them was shipping and fulfillment. We ended up selling at the flex port. So we began to think about like side quests and main quests, like what are our side quests? Let's get rid of them. Let's focus on the main quests. The third thing that happened sort of in this new phase of Shopify, this new shape Shopify is these like spiky objects. And what that really meant was we basically brought in a new, new team, a new leadership team. And part of that process was Toby and I sort of thinking about like, what are the things that we think we, we truly should be spending our time on? Meaning the highest value for Shopify. And that meant that like, we kind of rearranged the company. Not necessarily around these like traditional roles of like, you do this, but rather like based on our strengths.

• 18:12Speaker 01

  And as part of that, you know, Toby's not on the earnings calls anymore because it just, I, I got that. I can do that. I think I can do that at a, at a, at a really great level. I think I can eventually be world class at those earnings calls. I'm going to focus on that and Toby is going to run product for Shopify. That has been ultimately one of the greatest transitions, I think. This is my 16th year at Shopify. It's Toby's 20th and we've been public now for about a decade, but you can't get there right away. You have to almost go through these phases in order to, to figure out what your spiky object is.

• 18:41Shaan Puri?

  That's pretty cool. It also, it's pretty rare. I think that if you look at how many CEOs are the best storyteller in their company? It's actually not most, but they don't want to give that up. And so I think even in there, you didn't even mention it, but there's a sort of almost like a very telling thing that he had no, didn't have the ego to say, no, I need to be the front man also. I need to be the lead singer, even though I'm actually the best drummer.

• 19:03Speaker 01

  So Toby refers to me as the lead singer of the band. Like I think a lot of companies throw around this idea of mission. Shopify's mission is very simple. Like increase the amount of entrepreneurs on the planet. That's it. And we increased it by, by adding more entrepreneurs to Shopify who otherwise were aspiring previously.

• 19:19Sam Parr?

  Dude, how do you hire people if that's your mission? That's a hard thing to like, like all your employees would be fucking quitting.

• 19:25Speaker 01

  Well, actually the best part is we end up hiring mostly entrepreneurs. People that have had some, that entrepreneurship in some way has deeply affected their life. For me, my, my, my grandparents are Holocaust survivors. They, after the Holocaust, they went to Hungary. In the 50s, Hungary got really bad. Hungarian revolution happened. Canada let in 40,000 Hungarian immigrants in 1956. My grandfather came here with my father and his siblings. They came to Canada. My, my grandfather ended up selling eggs at a farmer's market. His whole life, that egg stall, it's called La Capitan, still stands today. It's like five kilometers from where I'm standing right now. So entrepreneurship for me is deeply personal because it allowed my family to survive and also create the life that allows me to be here. My version of that is when I moved, I grew up in South Florida.

• 20:10Speaker 01

  I moved to Montreal to go to McGill when I'm seventeen, in two thousand and one. And my dad was no longer in our lives. I had to support myself and my mom and my sisters. And so I started a t-shirt company. That t-shirt company would eventually become an online t-shirt company. And I would become one of the first merchants to use Shopify. That's kind of how I got here. But, and Toby comes in a very different way. He's an immigrant, he lives in Germany, meets someone, a wonderful woman who becomes his wife named Fiona. He moves to Canada, can't get a job as new immigrant, wants to start a snowboard shop and finds it incredibly difficult to do so, writes a piece of code to sell these snowboards, which would then should become Shopify.

• 20:46Shaan Puri?

  You know, our buddy George Mack has this great phrase where he says, "People only remember your weird." Meaning, any behavior that's standard that you do, might be very useful, but it's not very memorable.

• 20:58Speaker 01

  Yeah.

• 20:58Shaan Puri?

  And so, you know, Sam was asking about Toby just now. And, you know, I think, like he said, he's a bit of a mysterious character. He's not somebody who's out there doing a bunch of podcasts and public things. I'm curious, what's, what are some stories of his weird? Like, you know, what's a behavior or a thing that he does that's non-standard?

• 21:17Speaker 01

  There are a couple of things that I think define, you know, his leadership really well at Shopify. One fundamentally is that he spends a lot of his time using, like, all the newest tech, constantly. He's constantly reading the newest white paper on a new LLM that just came out. Like, this, and I don't think that's uncommon, I think you'd see that with Patrick or Zuck. But there is a category of these, like, super-technical founders that did not exist historically, at least. If they did, they weren't running hundred-billion-dollar or trillion-dollar companies. Toby's in this group of people that are super-technical, that know more about the codebase than anyone else on the planet. The other thing that I think is important is, one of the things he does every year is, basically, you know, during Christmas break, he spends his time running effectively the priorities for the company. And January first, every single year.

• 22:02Speaker 01

  For the last decade or so, the whole company gets an email and it's incredibly specific direction of like, what are we going to build this year? And it's not based on necessarily like, you know, it's based on his deep intuition of how the product needs to evolve. And in some cases, you know, it's, it's, you know, Shopify runs some of the largest flash sales on the planet like for Supreme or Taylor Swift or these, these massive, you know, crazy throughput, 30,000 transactions a minute type of stuff. So sometimes it's like, you know, we have to be able to like, to have this type of throughput. And other times it's, look, the future retail is not going to be just online. It's going to be everywhere and Shopify has to make it super easy to sell across every surface area.

• 22:43Speaker 01

  I announced two weeks ago, we're doing it with Roblox inside of like basically the Roblox universe. That now we're embedding commerce in into there as well. Toby didn't say, go do like Roblox. What he did say was make sure that everywhere where consumers are spending their time, there is a way for our existing merchants to easily turn on that channel. And it turns out like in something like Roblox, I forget what the DAUs are, but like it's ridiculous. I think there's like 700 million monthly users in the metaverse. I think the largest chunk of those are on, are in Roblox. It's like a hundred billion dollar industry today. It's going to be like 930 billion in 10, by 2030, I think. So we're like effect, so that's the type of stuff that he does is that he, he doesn't necessarily like, I know some CEOs will go and talk to customers.

• 23:28Speaker 01

  He does it also, but ultimately what he's, I think incredibly good at is the intuition that. The second thing is I think he spots talent really well. He finds these people across Shopify that are unobvious people. And he gives them the room to do their very, very best work. And 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, 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,

• 24:12Speaker 01

  Fairly confident in my ability to get better at stuff. But 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, 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, he also believes he has to requalify every year. And the pressure that he, that, you know, like he hasn't put more pressure on anyone else than he puts on himself. That I think is an amazing thing.

• 24:45Sam Parr?

  Does someone like him evolve into this like Jedi master type of guy? Or when you had 20 people or 10 people or whatever it was, was it clear that this guy is special?

• 24:55Speaker 01

  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 teacher, my teacher business that I had in college at McGill here in Montreal had gone, it became, you know, pretty good teacher business. I 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, that I was paying for. I was paying my mother's rent at that point.

• 25:32Speaker 01

  A mentor of mine convinced me to go to law school, not to become a lawyer, but he thought of, he looked at law schools being like finishing school for entrepreneurship. And he was, 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 we, I think it's going to make you a much better entrepreneur. You'll learn, you know, how to critical reason, how to write better, how to think better, how to articulate yourself better. So 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.

• 26:13Speaker 01

  Even in 2005, he was thinking about what the future of the internet might look like.

• 26:18Sam Parr?

  So do you remember, can you give us a bunch of those quotes?

• 26:21Speaker 01

  Yeah, I remember him saying, like, for example, one of the things that like payments should have been into, should have been built into browsers. And I'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 that he had done that I thought was incredibly inspiring to someone that, you know, praised at the altar of entrepreneurship was, at that point, there were a couple of companies doing e-commerce. There was a company called Magento, which ended up getting acquired by Adobe.

• 27:03Speaker 01

  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 like, no one is really doing like major GMV 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. Meaning if you have an ID 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?

• 27:47Speaker 01

  Well, the end result is that you like, we now have, there's now been a trillion dollars, transacted on Shopify, 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 of small businesses. And those homegrown success stories, companies like Fashion Nova, or Jimm Shark, 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.

• 28:31Speaker 01

  Like, that was a dramatic insight for me that, okay, if you couple ambition and incredible product technology, you can actually change the entire trajectory of entrepreneurship on the planet at a huge scale.

• 28:46Sam Parr?

  Where has he been wrong? Where's the weakness? Where's the human side of this?

• 28:50Speaker 01

  Yeah, so he's...

• 28:51Sam Parr?

  Because it sounds amazing.

• 28:52Speaker 01

  Are you guys familiar with the Enneagram?

• 28:53Shaan Puri?

  Yeah.

• 28:54Speaker 01

  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.

• 29:04Shaan Puri?

  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.

• 29:14Speaker 01

  Okay, now go to three.

• 29:15Shaan Puri?

  The achiever. Self-assured, what does it say? Self-assured, attractive, there you go, charming. Ambitious, competent, energetic. At their best, they are a role model who inspires others, but they have, you know, basic fears of being worthless, basic desire to feel valuable.

• 29:30Speaker 01

  Oh, yeah, that hits, man. That hits. So first of all, for anyone listening, like, 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 in 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. So knowing that, Toby being a challenger, 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 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.

• 30:10Speaker 01

  And if the two are correct, and even though they may not be the most polite way to say it, he doesn't care. He is seeking the best result. Like, that is why he should be, you know, I will work at the company as long as they'll have me and as long as he's there because 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 talked to my peers at other companies, they're like, yeah, you know, like, there is not a softness, but there was a collegiality to their culture.

• 30:43Speaker 01

  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.

• 30:48Shaan Puri?

  Did you guys ever have acquisition offers? You talked about how Magento sold and these other guys sold. Was there ever a moment?

• 30:54Speaker 01

  Everybody sold.

• 30:55Shaan Puri?

  Where you guys had an offer or a discussion that you had to take seriously and you had a fork in the road moment. You obviously ended up independent. But was that always, was that the only way this could have gone?

• 31:07Speaker 01

  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. That 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 about it and thinking about it. And 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.

• 31:44Speaker 01

  Once you take that phone call from a corp dev person at a big company, you begin to inadvertently or inadvertently start a process in your mind of beginning 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 can do it here with more scale. So 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.

• 32:24Speaker 01

  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 with, one is Klavio. You know, Andrew, who's founder of Klavio, went public last year. And then Fiji, who was at the time CEO of Instacart, was on our board, went public as well. So you've had a couple IPOs, but generally companies are, and in the case of, you know, most of these companies, they're much larger. They're in the tens of billions of dollars of market cap before. Or they actually go public. So are we just didn't want to get acquired and we want to be independent.

• 32:58Sam Parr?

  But were there ever times where you were like, I would like to, I would like to take this deal. This would be nice.

• 33:03Speaker 01

  No, there, um, uh, tr- truly, there was not. We, uh, we did, 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.

• 33:14Shaan Puri?

  And what's your philosophy? Are you, are you like a de-risker over time? Or are you like, fuck it, all the eggs in this basket? Like, what's your philosophy around that? Cause it's, it's tricky, right? Like even if you believe.

• 33:23Speaker 01

  Money, money is, so money is, so my, so, you know, I mentioned my dad wasn't around, um, when I, what's got to college. My, 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. Um, and growing up, um, money felt emotional to me that some weeks we had and some weeks we didn't. We never, we never, you know, we always had food on the table, for example, but there were times where I, I remember as a kid, often my mom would come sit me down and say, hey, like, we're gonna have to, you know, tighten our belts this, this, this month. And that, that tightening of the belt happened a lot, um, during my childhood. And so when we went public, yeah, for the first time I had real money, I was able to, um, I, you know, I, I was on a, a 10B51, which in Canada we call an ASTP, an automatic share distribution plan. So I was able to take a lot.

• 34:07Speaker 01

  But, I mean, I don't think there's any better investment for me and my family than, than Shopify. Um, but I've taken money off the table so that I feel like my family is secure, my children are secure. We, we're never gonna have to tighten our belts. And that, that's not a flex, that, that truly makes me feel, I'm able to do better work because I know that I have a nest egg that is protected.

• 34:29Shaan Puri?

  What was the hardest, what was the hardest moment at Shopify? Was there, what was rock bottom? What was the low?

• 34:34Speaker 01

  Oof. Um, COVID was really, really hard. Um, maybe not for the reasons that, you know, you guys, I mean, you remember Shopify went from something like, um,

• 34:46Speaker 01

  I don't know, maybe pre-COVID, we were a $30 billion company. We like overnight became...

• 34:50Sam Parr?

  I have your revenue. I think in 2019, you were at 1.6 billion. And then 2020, you were about 3 billion.

• 34:57Speaker 01

  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 at around 15% in the US. So 15% of all retail was on online. And then effectively, you had this pull forward during the pandemic, where like we jumped very quickly to 20-something percent.

• 35:13Sam Parr?

  Sean, to answer your question, what was the hardest time at Shopify? You know, we almost didn't make it. We grew from 1.5 to 3 billion.

• 35:21Speaker 01

  Can I finish my fucking story, guys? So 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 needed 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. Shopify also, for the first time ever, I think, we were not profitable. So I think that sort of post-COVID hangover was really tough for us. And that's kind of where, like, I think, you know, you asked me about the different phases.

• 36:05Speaker 01

  That's where I think sort of the next phase came into play, which is, okay, like, we need to figure out, like, what do we care about? 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. I wasn't sure if I was going to make it.

• 36:25Sam Parr?

  Was there a time where you thought that Shopify wasn't going to make it?

• 36:27Speaker 01

  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, that was hard, right? Like, I mean, we were bootstrapped for a while. There were times where we didn't know if we can cover payroll. But you know, I think you have to be a little bit, you know, crazy naive.

• 36:55Sam Parr?

  Sean and I, you know, my last company, we were gonna 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 in a bunch of things that are, that are potentially in the, 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 dollar 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,

• 37:28Speaker 01

  Does it go away?

• 37:29Sam Parr?

  Does it get more fun?

• 37:29Speaker 01

  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, 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, and that's gonna pay all my expenses and I can do. And then you hit the number, you're like, it's like, 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, like, at 7,000 people and 100 billion dollar market cap are very different than what I had with like 70 people.

• 38:10Sam Parr?

  Which problems do you enjoy more?

• 38:13Speaker 01

  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. And I believe now the microphone that I have because of Shopify's 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.

• 38:35Sam Parr?

  I remember you've always been lyrical and good at talking. You are now much better. You're always, you're always good. Now you are like really great. Do you have like a, do you have like a writer? Like, is there someone who's gonna watch this and be like, this bit hit?

• 38:48Speaker 01

  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. No, there's.

• 38:54Sam Parr?

  Yeah, we didn't use any of them.

• 38:55Speaker 01

  Yeah, exactly. I don't even think, I don't even know what I wrote to you.

• 38:58Sam Parr?

  Wait, what are you gonna say, Sean?

• 38:59Shaan Puri?

  I DM'd him this morning and I was. Just like, hey, uh, 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. It's like, you know, I was like, no, I said, 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.

• 39:30Speaker 01

  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.

• 39:36Shaan Puri?

  No, but you should. Like, I actually heard a couple of stories recently that have really inspired me. Okay, I'm gonna 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, uh, you know, treatments and coaches and like 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, uh, less than half of that team in the NBA raised their hand. I was like, this is insane. I couldn't believe the owner would even allow that. But like for LeBron, every meal is dialed. Every, you know, every hour of the day is either recovery, it's button, it's building, or it's, uh, you know, it's playing.

• 40:21Shaan Puri?

  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.

• 40:30Speaker 01

  The opposite.

• 40:31Shaan Puri?

  He stutters a bunch, he stumbles. But when Peter Thiel goes on tour and he does it like every, you know, seven to 10 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 like, you know, if you remember, he did one where it was, uh, universities are a bubble.

• 40:50Speaker 01

  Yeah.

• 40:50Shaan Puri?

  Right? And he went on a whole tour with that. And then he launched the Thiel Fellowship underneath it. And he did one, which was Competitionists for Losers. And he has these like slogans, almost like marketing slogans, it competes for losers. Then he launches Zero to One, his book that was all about how to build a monopoly. And he did one with, when Trump first ran, he was like, you know, and for founders went ahead, we wanted flying cars, but all we got was 140 characters.

• 41:10Speaker 01

  Yeah.

• 41:11Shaan Puri?

  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 of Peter's thoughts and then sort of workshopping his bits like a comedian would, like a politician's speechwriters 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,

• 41:36Speaker 01

  I, I know David, so David actually has 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, our amazing CFO, I 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 then I basically take it and, and I, you know, hardly arise it. I make it sound like me.

• 42:06Sam Parr?

  So can you give an example? So an example is like, uh, we want to get, we want to be on Roblox or something.

• 42:11Speaker 01

  On the Roblox thing, it's really about the fact that Shopify is no longer just an e-commerce company. We're the commerce everywhere company.

• 42:17Sam Parr?

  Okay.

• 42:17Speaker 01

  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 on Roblox if you're selling hand sanitizer. But 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.

• 42:36Shaan Puri?

  Right, right. The story isn't we're on Roblox. The story is we're now the e-commerce, we're now the commerce everywhere company.

• 42:42Speaker 01

  Pinterest and Instagram, we, there's, there's literally a Spotify, a Shopify for Spotify channel. Where you can actually, if you're, if you're a large, if you're Beyonce and you have an artist profile like the size of Beyonce, you can sell Sacred, which is her cosmetic line on Shopify, inside of her artist profile.

• 42:56Sam Parr?

  Rumors are you're going to be on ChatGPT.

• 42:59Speaker 01

  That's rumors, yeah. We're not going to go there today, but, but exactly. We want to be wherever you, you, you effectively have consumers. So earnings was three weeks ago and I, 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, I did TBTN, uh, which, 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 listen to earnings calls a couple of 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. And Sebastian from, I think, is it Klarna or something? He basically came out, I think it was Sebastian, and he said, hey, after his earnings call, the whole thing was done by AI.

• 43:41Speaker 01

  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 of 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. And then I watched a bunch of other kind of, quote unquote, 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.

• 44:23Speaker 01

  And I'll use voice inflection, and I'll use repetition, and it doesn't, and what I hear back from, it's like theater. What 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 is, 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, you know, I've been, 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,

• 45:05Speaker 01

  and then let me kind of find my own way of negotiating it into the call.

• 45:09Shaan Puri?

  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.

• 45:17Speaker 01

  There are people that, I mean, Benioff's fantastic at it.

• 45:20Shaan Puri?

  Do you, uh, so Toby came out with this like memo that was like, uh, hey, it is a baseline expectation.

• 45:26Speaker 01

  He didn't come out with it. It was leaked, but yes, yeah.

• 45:28Shaan Puri?

  It was leaked.

• 45:29Speaker 01

  Someone leaked it.

• 45:29Shaan Puri?

  I always assumed those are like intentionally leaked. I would have intentionally leaked that if I was him.

• 45:32Speaker 01

  I think in hindsight, some of those things, when they do get leaked, you're like, you know, for better or for worse kind of thing, but yes.

• 45:38Shaan Puri?

  But the point is in it, he was basically like, yo, AI is an expectation, a baseline expectation. You gotta learn these tools. The way to, the way to get good at them is to use them a bunch. And you gotta start solving problems using this, um, was, 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?

• 46:02Speaker 01

  Two things. One is, I mean, I use chat GPT. I really like the fact that now it's, um, 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 upload a chat GPT 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 my 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, I gave a keynote at Summit last week. I literally fed my entire keynote script into chat GPT 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?

• 46:43Speaker 01

  So I think that I use chat GPT 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, Lynn, 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 in. 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

• 47:26Speaker 01

  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 Shopify Capital, 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 on 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 the capital program, because everything is legible, I was able to pull most of the data on my own. The personal jury's still out whether or not I missed, because 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, 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.

• 48:10Speaker 01

  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 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. And 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

• 48:54Speaker 01

  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. And 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, 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.

• 49:34Shaan Puri?

  I like that a lot, that's cool, that's a- 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 US like, oh, the deficit's 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.

• 49:58Speaker 01

  That's right.

• 49:58Shaan Puri?

  Watch, watch what happens.

• 50:00Speaker 01

  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. So 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 emo 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.

• 50:30Shaan Puri?

  Well, 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 either interesting or working for you or you're enjoying it. Just give us kind of like a quick health dump.

• 50:46Speaker 01

  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, so I'm now getting to the point where I'm taking it a lot more seriously. So once a year, and there's, 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 into these full body MRIs because they get claustrophobic. So a small, you know, 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.

• 51:29Speaker 01

  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 wouldn't want to stay in something like that for a long time.

• 51:40Shaan Puri?

  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 the original Top Gun.

• 51:46Speaker 01

  I'm like, I do not want to be stressed out. I don't want to be scared.

• 51:49Sam Parr?

  Dude, I watched a Zodiac Killer documentary on Netflix. It was great.

• 51:52Speaker 01

  I mean, that speaks volumes about your, both your personalities. I watched like Seinfeld. And so, so that sort of takes you on the cancer side. On the cardiovascular stuff, 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 it growing year over year? Now at least I can monitor that stuff too. So to me, those are the two main buckets. And then I just try to do these like, these misojis is like one thing every year that scares the shit out of me. And the thing I really like right now is called 29029 and

• 52:35Sam Parr?

  Jesse Isler?

• 52:35Speaker 01

  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. In 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 is 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 29029 thing.

• 53:17Sam Parr?

  Yeah.

• 53:18Speaker 01

  Yeah.

• 53:18Sam Parr?

  Dude, how many, 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 one, whatever, 130, you've been as high as

• 53:30Speaker 01

  134.

• 53:31Sam Parr?

  200 something?

• 53:31Speaker 01

  You guys are rounding down by $20 billion, just one of them.

• 53:34Sam Parr?

  It's casual. Dude, what's crazy is like, you're worth, you're worth 134.56 billion. Like change that 5.6 to like a 5.5 and like, that's like life changing. You know what I mean?

• 53:45Speaker 01

  It's crazy, for sure. No, it's, it's wild. I, look, let me, let me, one more call out for, if you were listening to this and you are a company that actually like, you know, you, you understand your business well. You see great growth potential, like this idea of 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. I think you, I think one of the things they love about it as a product is that like being publicly traded provides some sense of stability.

• 54:22Sam Parr?

  Well, what I was gonna 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. He's like one of us almost.

• 54:52Speaker 01

  That's our friends.

• 54:53Shaan Puri?

  Fuck, he's not one of us, damn it.

• 54:55Sam Parr?

  And then I like see this, 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.

• 55:03Speaker 01

  You know me personally, we've like, I think I said this at the beginning, right? I was guest 118.

• 55:09Sam Parr?

  We are not the same, my friend. We are not the same.

• 55:11Speaker 01

  And now you had over 750 of them.

• 55:14Sam Parr?

  We are not the same. And but if there were a ratio of like, I feel like I could do whatever he's done to.

• 55:21Speaker 01

  Approachability to market cap ratio.

• 55:22Sam Parr?

  You are, you get the gold medal.

• 55:25Speaker 01

  I think that's the sweetest thing you've ever said to me, Sam.

• 55:27Shaan Puri?

  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.

• 55:38Sam Parr?

  Oh, wow. That's cool.

• 55:39Shaan Puri?

  And 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 me.

• 55:57Speaker 01

  Well, that means a lot to me. It's actually cruelly neat. I get to, we're doing this thing called Shopify Milestones. Like basically it's our version of like 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 ones. We get in for 10,000 orders, 100,000 and a million orders.

• 56:12Shaan Puri?

  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. Like this is so slow. How you guys set these out?

• 56:19Speaker 01

  I mean, these are heavy. We had to like ship them out and stuff. There's a lot of people. But anyways, so I get to, I deliver a bunch of milestones in person. That's your excuse. Yeah, they're heavy. 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, but then also to invest your, you know, your, your hard earned money into.

• 56:49Shaan Puri?

  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. I'm going to get it back in a different way.

• 56:56Speaker 01

  You made it, you made it sound way less romantic than I just.

• 56:58Shaan Puri?

  Yeah, exactly. Let's be real here. Dude, thanks for coming on, man.

• 57:02Speaker 01

  Dude, this is great. You guys are the best.