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

This is serious podcasting over here.

Sean, the last time I did this, actually, I literally pulled up the date of it. 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.

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

I feel like I could 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 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.

Oh yeah, of course. I, 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.

It's hand sanitizer. 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's 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, Purell—

it was all like Purell.

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

Uh, alcohol. It's like something you get at the hospital or a teacher—

from a teacher. Exactly. Horrible smell. Smells like tequila. Uh, the form factor is not like 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 going to make it smell good. I'm going to make it look good. I don't know if you've seen the, like, the cases of it. It's basically like clear.

Beautiful.

It's like this, like, sort of, um, like almost Johnny Ive designed, like, case. Exactly.

Exactly. It's if, if Apple decided to like go into the hand sanitizer market.

So she— And she also did collaborations, right? Like Hello Kitty, Disney. I mean, this is like a whole different level of, of, of, of vision around hand sanitizer.

Wow.

Exactly.

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

Well, thank you.

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 sound pejorative, 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? Anyways, like, so, like, Dyson, like, the The guy, the man, the founder, he actually did it like this press conference. It's on YouTube now.

I just checked. He's amazing.

Have you guys seen it? He's like, totally amazing.

Isn't it like a 7-minute demo? And he just came and dropped the mic on like an epic—

I think it's even less.

I think it's like 5 minutes. But 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'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 going to buy their first Dyson product because of this video.

They never did before. Have you guys ever read about him? Sean, have you read about James Dyson?

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

Dude, like 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 2 or 3 years to the point where he was, I think he went bankrupt, but he still kind of kept at it.

Amazing. But you could sort of look 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 in consumer.

That's one of those ideas that I thought that was just go ahead and log in and just start reading out all the numbers for these brands.

I'm not going to do anything like that. But what I will say, there's, you know, actually, let me, let me show you. I'm going to give me one second. You guys know my best friend David Siegel. I think you've had him on the show. Yeah. Founder of David's Tea. He's made, you know, took his company public. He's awesome. Made hundreds of millions of dollars. Him and I have this like tea business on the side we started during the pandemic called Firebelly Tea. Anyways, like we tinker like you guys do on weekends. We have 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—

last time you were on the podcast.

Exactly.

You talked about this.

Like it's a static number.

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

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 Flynn 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?

What's the answer of that?

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

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 that Eric Ryan— I also was not invited to speak at HustleCon, just to say the thing. Yeah. And we've actually decided to create our own called Super HustleCon.

Harleen, Sean, thanks.

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

Shit. We're the opposite.

Exactly. But yeah, I remember him speaking and he was brilliant. So he, for people who don't know Eric Rijn, 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 a, the big trend at the time.

But the bottle was like pretty.

The bottle was pretty and the, and the photography was pretty. Like they would do like a photo shoot instead of it being like You know, those like pharmaceutical commercials where they show a 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, the photography on the website.

Well, Moyes did that too, right? Moyes did that with, with Native and sold for $100 million to, to Procter Gamble.

Yes. Eric actually did it with Ollie Vitamins. He also did it with, uh, 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.

Do those 8 a day actually do anything?

It's a little bit 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, uh, 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 do every, every year for my birthday, I do something called Prenova. Do you guys know Prenova?

Yeah.

Yeah. I've been doing it since I was, uh, for the last 6 years, every, uh, my birthday's November, every year.

Go to New York for a pretty bad birthday one year. Uh, you gotta be careful with that.

I mean, that's the, the issue with it. 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.

Have you— maybe you could answer this. You're actually the only person I've asked this publicly, 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?

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

Do you know any fat billionaires?

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

Of course.

You probably know them also. But maybe they're— Maybe there was a thyroid issue. I do believe that if you have the means and you can have, you know, uh, if you can have like 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. 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 or someone showing up at your house. So I do think that is easier for you to be in better shape if you have means.

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

I have a chef.

I have a personal trainer who comes to my house. Okay, I'll find a way. The will finds a way. And if I want to DoorDash something, I'll find a way.

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.

Yeah.

And also you have gotten way healthier over the last half.

That's right. Yeah.

You know, when I had my first child, Bailey is now my daughter's 8. When I had her first child. So Dave Siegel, again, bring 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, Uh, 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, like luxuries in your life. Um, and I, 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.

I heard an interesting story, uh, about actually last week. I was with a person I'm not going to name, but he's, uh, like a, he's a billionaire and he's an, he's a big time investor. And he was telling stories about how he, uh, we were talking about Shopify. I was actually talking about how I met with, met with you. And, uh, 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 Tobi 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? And he said, whenever I'm with the Collison brothers, we talk all about like interesting philosophical things and like what their like hobbies are and things like that.

And whenever I'm with Tobi, 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.

Is this the beauty of this founder-led thing? I mean, I, you know, I think the Collinson 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.

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's like, he's still mysterious to me because I've never met him. But he seems like a, like, I think he has this one quote where he goes, my wife says I'm an immigrant to the human condition.

is there like a— could you put a threshold onto that? Like a number of people or something?

Um, yeah, I would say like for us it was like 0 to, I don't know, Dunbar's number. You know that concept, Dunbar's number?

150 or 150?

Yeah, 150 or something like that, which is like It comes from tribal times where that's how many people any human can remember at any one given time. So I would say like 0 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, um, partnership. I built the App Store and partnerships program. I was also the lawyer. I mean, I was general counsel. I wasn't really a good lawyer. I'd only practiced for a few months, but, um, like Better Call Saul. Yeah, I did. I 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 mark it 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 quite, quite well. Um, 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 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. 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 it to Flexport. 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 quest. But the third thing that happened sort of in this new phase of Shopify, this new shape of Shopify, is, um, these like spiky objects. And what that really meant was we basically brought in a new, new team, a new leadership team. Um, and part of that process was Tobi and I sort of thinking about like, what are the things that we think 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 and— but rather like based on our strengths. And as part of that, you know, Tobi's not on the earnings calls anymore because it just— 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 Tobi 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 Tobi'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.

That's pretty cool. It also, it's pretty rare. I think 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 frontman also. I need to be the lead singer, even though I'm actually the best drummer.

So that's— 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 increase it by, by adding more entrepreneurs to Shopify who otherwise were aspiring previously.

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.

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 went 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 grandfather ended up selling eggs at a farmer's market his whole life. That egg stall, it's called Le Capitaine, still stands today. It's like 5 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. I moved to Montreal to go to McGill when I'm 17 in 2001, 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 to it 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 a 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 eventually become Shopify.

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

Yeah.

Uh, and so, you know, Sam was asking about Tobi just now. And, you know, I think, like you 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?

There are a couple things that I think define, you know, his, 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, a new LLM that just came out. Like, this idea, and I don't think that's uncommon. I think you'd see that with Pat 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 $100 billion or trillion-dollar companies. Toby's in this group of people that are super technical, that know more about the, the, the codebase than anyone else on the planet. The other thing that I think is, is, um, 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 1st, every single year, I don't know, for the last decade or so, the whole company gets an email and it's incredibly specific, uh, direction of like, what are we going to build this year? And it's not based on necessarily like, you know, survey. It's based on his deep intuition of how the product needs to evolve. And in some cases, you know, it's, it's, um, 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 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 of 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. I announced 2 weeks ago, uh, 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, the DAUs are, but like, it's, it's ridiculous. I think, um, there's like 700 million monthly users in the metaverse. I think the largest chunk of those are on, uh, are in Roblox. It's like a $100 billion 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 it's I know some CEOs will go and talk to customers. He does that also. But ultimately what he's, I think, incredibly good at is the intuition on that. The second thing is I think he spots talent really well. Um, 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 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 I even, I see from 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. 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 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 hasn't put more pressure on anyone else than he puts on himself. Um, that I think is an amazing thing.

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's 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. Tobi 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, my t-shirt business that I had in college at McGill here in Montreal, had gone, 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 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 of— he looked at law school as 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. Even in 2005, he was thinking about what the future of the internet might look like.

So remember, 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, that like payments should have been into, should have been built into browsers. I'm like, what? He's like, yes, like the people that made browsers completely fucked this up. Payments should, should be natively integrated, not through a third party, but natively built into 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 as someone that, you know, prays at the altar of entrepreneurship was at that point there were a couple companies doing e-commerce. There 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. 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 was 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 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 of small businesses. And those homegrown success stories, companies like Fashion Nova or Gymshark or all of 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, if you, 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.

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

So he's—

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, worth any, any, any review. But, um, so he is an 8.

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 3.

The Achiever, self-assured, uh, 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, you know, basic fears of being worthless, basic desire to feel valued.

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 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. 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, 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 2 will do. He'll say 2. And if the 2 are correct, and even though they may not be the most polite way to say it. He doesn't care. He is, he is seeking the best result. Like that, 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, the, he is the CEO that Shopify requires. No one will care more about that. Um, but that doesn't make it easy. Right. And like, I know other companies, I talked to my peers, other companies are like, yeah, you know, like there is, um, not a softness, but there was a collegiality. To their culture. That doesn't happen at Shopify. It's not, it's not that we're not collegial. It's just like, that's not what we're trying to achieve.

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

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

No, there, um, uh, true that 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.

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? Like what's your philosophy around that? Because it's tricky, right?

Like even if you believe money, money isn't so money's about so my so, you know, I mentioned my dad wasn't around when I went 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, 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. And that 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 10b5-1, which in Canada we call an ASTP, 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 and my family than, 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, 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.

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

Oof. Um, COVID was really, really hard. Um, maybe not for the reasons that, you know, you guys, I mean, remember Shopify went from something like like, um, I don't know, maybe pre-COVID we were a $30 billion company. We like overnight—

I have your revenue. I think, I think in 2019 you're at $1.6 billion and then 2020 you're 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 at around 15% in the US. So 15% of all retail was done online. And then effectively you had this pull forward during the pandemic where like we jumped very quickly to 20-something percent.

Sean, to answer your question, what was the hardest time in Shopify? You know, we almost didn't make it. We grew from $1.5 million to $20 million.

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 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, was really tough for us. And that's kind of where like, I think, you know, you asked me about these 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 do we care about? Um, 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. Um, that was really hard. I wasn't sure. I knew Shopify would make it. Um, I 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, uh, 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, you know, grow, grow top line and also grow bottom line. Um, but pre-pandemic, there was— sorry, pre-IPO, there were— I mean, 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. Um, but, you know, I think you have to be a little bit, you know, crazy naive.

Sean and I, uh, you know, 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 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 range where I'm like, oh, then I could just like manage like 3 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 got to go do the work. And so what I want to know is like, does it go away? Does it get more fun?

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. And I believe now the microphone that I have because of Shopify's size allows me to do it at this scale. 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 be— you've always been lyrical and good at talking. You are now much better. Uh, you are always— you are 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?

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, yeah, exactly.

I don't even think— I don't even know what I wrote to you.

Uh, but 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 3 or 4 bullet points. I gave him some guidelines. I was 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.

Uh, yeah, so, so I mean, I had, I have a team of people that help me with things like when 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. Okay, I'm going to 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 $1 million 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, 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 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, it's building, or it's, you know, 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, yeah, there's a bunch, he stumbles. But when Peter Thiel goes on tour and he does it like every, you know, 7 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 his words, but he's very effective. And, you know, if you remember he did one where it was, 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. Competition is 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 Fund 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 of Peter's thoughts and then sort of workshopping his bits like a comedian would, like a, 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, he, he's a media guy. I know David, so David actually has a, uh, 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 CFO. I met with Jeff and our IR team and I'm like, all right, what are the 3 or 4 things that like that we want to, we want to say? And then I basically take it and I, you know, Harley-erize 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 just an e-commerce company. We're the commerce everywhere company. Okay. 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, 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. 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.

We're also on Pinterest and Instagram. 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 Beyoncé and you have an artist profile like the size of Beyoncé, you can sell Sacred, which is her cosmetic line on Shopify inside of her artist profile.

And rumors are you're going to be on ChatGPT.

That's rumors. Yeah, we're not going to go there today, but, but Exactly. We want to be wherever you effectively have consumers. So earnings was 3 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, I did TVTN, 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, uh, companies that, because I listen to earnings calls a couple days before and a couple 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, I'm, I, after his earnings call, the whole thing was done by AI. That actually was, it was, 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 5 out of 10. And maybe you can say it's a 6 or 7 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 And then I watched a bunch of other kind of quote-unquote professional executives that were, 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 and I'll use repetition. And it doesn't— and what I've known 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, I'm— 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, 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, and 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, others may not.

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

Do you, uh, so Toby came out with this like memo that was like, uh, 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.

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.

But the point is, in it, he was basically like, yo, AI is an expectation, a baseline 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, 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 ChatGPT, other tools? Like, what are you actually personally just using, either professionally or personally in your personal life?

I like that a lot. That's cool. That's a, that's a great little nuance. Um, and, 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 2 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. So simply by adding, you know, a simple friction on hiring that says first substantiate it, you actually see incredible results. Then you can evaluate, you can literally say like, okay, well, how has hiring changed since that, that, 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.

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, uh, 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 gonna die of one of two ways. I'm gonna either die because of cancer or I'm gonna die because of heart attack. And so the cancer thing, um, 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. Um, 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. Um, 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 somewhat— 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.

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 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.

I mean, that speaks volumes about both your personalities. I watched, like, Seinfeld. And so that sort of takes you on the cancer side. On the cardiovascular stuff, I just did a Cleerly 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 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. Um, and then I just try to do these like, um, these misogys 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 Jesse Itzler'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. 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, Mount 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 to 29 thing.

Yeah.

Yeah, dude. How many— last question. How many, how many companies in the world are bigger than Shopify? You guys are worth, it looks like $153 today or something or $130. You've been as high as $134.

$200. We just rounded down by $20 billion.

Just one of— casual.

What's crazy is like you're worth, you're worth $134.56 billion. And like 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. No, it's just, it's wild. I look, let me, 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 understand your business well, you see great growth potential. Like this idea of, of avoiding the public markets is, is insanely silly to me. It's been an incredible 40, 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 and Mattel and Birkenstocks using Shopify. Like, 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.

Well, what I was gonna say was I looked it up on ChatGPT. So, uh, there are probably 120 companies in the world bigger than you, which means of all the companies that have ever been started, uh, of all the companies that are out there right now and probably in the history, given that, like, 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.

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 was I guess 118.

We are not the same, my friend.

We are not.

We are the same.

And now you had over 750 of them.

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 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 what's one of the best things I did after that first podcast is basically every year for the last 5 years, I take about 20% of whatever my profits are out of my Shopify store. And I just buy Shopify stock.

That's cool. That alone I think has compounded as good or better as my actual e-com brand because now my earnings are growing, whereas like if I just reinvested it in the business, you know, not every business you can reinvest 100% of your, your, your profits back into. And so just that one little habit has been very, very helpful for me.

Well, that means a lot to me. It's actually really 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 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. So we get it 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. Like, this is so slow how you guys send these out.

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 deliver a bunch of Milestones in person.

That's your excuse.

They're really heavy. 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 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. I want to get it back in the deposit.

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

Yeah, just trying to kind of— let's be real here. Dude, thanks for coming on, man.

Dude, this is great. You guys are the best. I feel like I could 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.