Shopify President: While Everyone Chases AI, Sell These Products

- June 11, 2025 (10 months ago) • 58:15

Transcript

Start Time	Speaker	Text
00:00	Shaan Puri	This is serious podcasting over here.
00:02	Harley Finkelstein	"Sean, the last time I did this—actually, I literally pulled up the date. It was in 2020. I think you were in, like, a wife‑beater. 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."
00:18	Shaan Puri	Hey, we haven't come that far. These things... that still might be — it might happen today. 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.
00:36	Harley Finkelstein	Oh yeah, of course. In fact, I've given them out at events.
00:41	Sam Parr	But their headline doesn't make sense. It's "Sensory essentials that bring delight to everyday moments of care" — is that?
00:48	Harley Finkelstein	It's hand-sanitizer perfume, yeah.
00:49	Shaan Puri	It's hand sanitizer. So, check this out — this story is pretty crazy. This person starts out distributing hand sanitizer in Africa, where sanitation is super important. People get really sick because they don't have clean water. She gets this idea: "What if I made hand sanitizer sexy?" At the time, Purell... yeah.
01:14	Harley Finkelstein	It was all, like, Purell. Exactly.
01:16	Shaan Puri	"Crap. And if you—if you think about Purell, Sam, what does it... what does it smell like?"
01:21	Sam Parr	Alcohol. It's like something you get at the hospital, or a teacher— from a teacher. Exactly.
01:25	Shaan Puri	Horrible smell — it smelled like tequila. The form factor was nothing to brag about, nothing to show off. It was a pure utility product. What she did was reimagine it as a luxury product. So she took hand sanitizer and said, "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 cases of it — they're basically clear. </FormattedResponse>
01:44	Harley Finkelstein	"It's beautiful. It's like this—sort of almost Johnny Ive–designed case. Exactly."</FormattedResponse>
01:51	Shaan Puri	Exactly. It's... if Apple decided to get into the hand sanitizer market and she...
01:55	Harley Finkelstein	Also did collaborations, right? Like Hello Kitty, Disney. I mean, this is a whole different level of vision around hand sanitizer.
02:04	Shaan Puri	So she comes up with this idea. She goes on Kickstarter and raises $67,000. She’s like, “Okay, great — $67,000; I could do a first run.” In the first year she does about $1,000,000 in sales. Then COVID happens, and obviously people care about hand sanitizer way more during COVID. The business just explodes. Recently — this is now 2025 — it was acquired for $880,000,000. It was a hand sanitizer company, and I love this story.
02:33	Sam Parr	It says it was gonna do it. Took this year, it's gonna do $130,000,000 in revenue and $55,000,000 in EBITDA.
02:39	Shaan Puri	Wow—exactly. Incredible. And they're on Shopify. There you go, Harley.
02:43	Sam Parr	There's your plug.
02:44	Harley Finkelstein	Well, thank you. Thank you for plugging.
02:45	Shaan Puri	But, dude, isn't this a crazy story? How cool is this? Basically, this concept is: how do you take an ugly thing—or just a commodity, utilitarian product—and then apply high fashion to it, apply luxury to it, and create your own category? It sells for more. It's the only hand sanitizer people gift to each other. We're saying, "you gift it." My wife saw it and she said, "Oh, I just got that as a gift for our kid's teacher on their last day of school." You would never gift Purell to somebody unless you're trying to tell them something.
03:16	Harley Finkelstein	I have—one of the cool things: we have a few million stores on Shopify. We're about 12% of all U.S. e‑commerce right now. One of the things I'm seeing a lot are what I think would be considered—this is gonna sound pejorative, but it's not—boring products becoming very sexy. I don't know if you guys saw this, but literally a week ago Dyson came out with this thing called the "Pencil Vac." Have you guys seen this? Anyways, so Dyson—the man, the founder—he actually did this press conference. It's on YouTube now. I just—[sentence trails off / inaudible].
03:49	Shaan Puri	It was a seven-minute demo, and he just came and dropped the mic — it was epic.
03:52	Sam Parr	I think he's even laughing. It was like...
03:53	Harley Finkelstein	Five minutes. But yeah—exactly. There's millions of views on this demo for a fucking vacuum cleaner. What I thought about it: one, Dyson is not a new company; they've been around for a very long time. But the idea that they took something fairly boring, made it way better, and now can leverage modern media like YouTube to tell a story is powerful. I bet a bunch of people are actually going to buy their first Dyson product because of this video—people who never did before. </FormattedResponse>
04:19	Sam Parr	Have you guys ever read about him, Sean? Have you read about James Dyson? </FormattedResponse>
04:21	Shaan Puri	Dude, you and David Senora won't stop talking about James Dyson.
04:24	Sam Parr	Dude, I started reading his book. He's just... the man. It sounds ridiculous, but he's the Steve Jobs of vacuums — Steve Jobs before Steve Jobs. He's that type of person: the inside wiring needs to be beautiful. I'm really interested in people who take non-serious things very seriously — vacuum hand dryers, whatever. I think it's so freaking cool. He was building the first prototype for two or three years. I think he went bankrupt, but he still kinda kept at it.
04:57	Harley Finkelstein	Amazing. But you could sort of look across a bunch of different things. I'm having my coffee now in my Ember mug, right? The idea of adding a small heater to a mug 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...
05:14	Sam Parr	Consumer — that's one of those ideas that I thought was good.
05:17	Shaan Puri	Ahead, log in, and just start reading out all the numbers for...
05:19	Harley Finkelstein	These brands — I'm going to do that, do something like that. But what I will say is... actually, let me show you. Give me one second. You guys know my best friend David Siegel. I think you've had him on the show, yeah? He's the founder of David's Tea; he took his company public.
05:30	Shaan Puri	He's awesome.
05:30	Harley Finkelstein	He made $100 million. He and I had this tea business on the side we started during the pandemic called Firebelly Tea. Anyways, 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 our way of… we think that Duraflame needs to be disrupted. That's a great idea.
05:48	Shaan Puri	So, like, we really appreciate your time... you were...
05:50	Sam Parr	On the podcast.
05:50	Shaan Puri	Exactly. Talked about this.
05:51	Harley Finkelstein	We had this idea in 2020. Actually, now David and I have a working prototype. It's actually—you can read it. It's literally made from Canadian softwood. It's 100% kiln-dried.
06:01	Sam Parr	It's a great idea.
06:02	Harley Finkelstein	*Branding — it's called Flint**, which we think is a cool name for it. You look across all these different categories of things that most of us as consumers take for granted, and there's always this 10x* version of it. My wife's really into—she's gonna hate me saying this—karaoke. If you've ever gone and tried to buy a karaoke machine, there are companies that rent them to you because they're so big and clunky. Someone should go and disrupt the karaoke-machine business. To me, that is such a brilliant idea. Or, you know, tools. You move into a new house and you kinda need, like, random tools. Most of these tool companies—those you buy at Home Depot—are clunky and don't look good. There are actually a couple of beautifully designed, almost "touchline" versions of tools selling on Shopify. People misunderstand TAM [total addressable market] to their detriment. Everyone kinda looks at TAM as being this thing, like: "What is the... there's a pie, and I'm gonna take a bigger piece of the..."
06:56	Sam Parr	It's a static number. Yeah... it's—it's very...
06:59	Harley Finkelstein	Much like zero-sum. Funny enough, Sequoia has said this publicly, so I think I can say it now. The reason Sequoia did invest in Shopify 15–16 years ago was that they looked at the TAM of retail SMBs on the planet. They effectively forecasted: if Shopify captured a meaningful percentage of that market, how big could the company be? What they missed was that we're actually growing the pie itself. There's a positive-sum effect: someone who's starting— I don't know the person behind Touchland, Sean— but presumably this person wasn't previously in the industry, and maybe wasn't even an entrepreneur.
07:36	Sam Parr	"But— is that the story you told yourself when you were doing it? Because when you're doing it, I mean, you guys—no, you can't."
07:42	Harley Finkelstein	That's the—you almost cannot do it. You actually have to almost imagine... let's just use Flint for a second. By the way, this is not for sale yet; this is just a prototype, so you can't go buy it. But let's just say what you would do for Flint: you'd ask, "Okay, what are the products in the market? The biggest one is Duraflame. How much does Duraflame sell a year?"
08:00	Sam Parr	"What... what's the answer to that?"
08:01	Harley Finkelstein	You know, I think it's something... I think it's...
08:03	Sam Parr	Like last time, we...
08:03	Harley Finkelstein	That category was like $500 million, and it was sold at Home Depot, Lowe's — these sort of home hardware stores. One of the things David and I were thinking about is: why are these not sold in convenience stores? Do I have to go to Home Depot for it? If I'm picking up my weekend beer at a bodega or a 7‑Eleven, I should also be able to pick up my flint. What you have to do as an entrepreneur is broaden the horizon of what the potential is. Kat Cole and I were just speaking last week. Kat Cole, who's the CEO of AG1, said they're doing $600 million a year with AG1 with one single SKU. There is no way Chris, the founder of AG1, originally thought about that. Basically, they didn't just grow their piece of the pie — they grew the pie infinitely. And I think those are the best entrepreneurs for me.
08:54	Sam Parr	Alright, so I've built a few companies that have made a few million dollars a year, and I've built two companies that have made tens of millions of dollars a year. So I have a little bit of experience launching, building, and creating new things. I actually don't come up with a lot of original ideas. Instead, what I'm really, really good at—what my skill set is—is researching different ideas, different gaps in the market, and reverse engineering companies. I didn't invent this, by the way. We had this guy, Brad Jacobs—we talked about him on the podcast. He started like four or five different publicly traded companies, each worth tens of billions of dollars. He actually is the one who I learned how to do this from. So, with the team at HubSpot, we put together all of my research tactics, frameworks, and techniques on spotting different opportunities in the market, reverse engineering companies, and figuring out exactly where opportunities are, versus just coming up with a random, silly idea and throwing it against the wall and hoping that it sticks. So if you want to see my framework, you can check it out—the link is below in the YouTube description. "Sean, did you ever meet Eric Ryan? I think he spoke at the HustleCon that you spoke at."
09:59	Shaan Puri	I didn't meet him, but I know—you never invited me to speak at HustleCon. I was just an attendee, but I did attend the one I also...
10:05	Harley Finkelstein	Was invited to speak at HustleCon, just to say "the thing."
10:07	Shaan Puri	Yeah, and we've actually decided to create our own called HustleCon. "hardly and sean, yeah." [Unclear phrase — "hardly" may be a name (e.g., "Hardy" or "Harold"); transcription uncertain.]
10:15	Harley Finkelstein	We're — we're — we're the opposite.
10:21	Shaan Puri	But, yeah—remember him speaking? He was brilliant. So, for people who don't know, Eric Ryan—he did Method soap. He basically went into a boring soap category and made it sexy, and he put ingredients you could understand on the back of the bottle. That was the big trend... but the bottle...
10:35	Sam Parr	Was, like, pretty.
10:37	Shaan Puri	The bottle was pretty, and the photography was pretty. They would do a photo shoot. Instead of being like those pharmaceutical commercials where they show a cartoon germ getting sprayed, it was two really hot people who are dating but haven't really defined their relationship yet, and they're cleaning up their house together. That was the photography on the website.
10:56	Harley Finkelstein	Well, Moise did that too, right? Moise did it with Native and sold it for $100 million to Procter & Gamble.
11:00	Sam 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. </FormattedResponse>
11:08	Harley Finkelstein	I mean, I have, like—like, you look at Just, Shop It; you look at Ritual (which is 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 $100,000,000 in annual revenue (this is public information; they put it out there), and 80% are recurring customers. You basically send them a follicle of hair, they analyze it, and they send you a shampoo specific to what you need. I think that personalization stuff for shampoo is really interesting. Even with supplements — if you guys take supplements, I take eight a day — I wish I could basically just take one pill that has exactly what I need, specifically for me.
11:46	Sam Parr	Do those eight a day actually do anything?
11:49	Harley Finkelstein	It's a little bit of, you know, correlation versus causation. All of my lipids are getting better, and I think there's definitely some correlation to it. Although, as part of taking all these supplements, I'm also working out more, eating much better, and drinking far less red wine on weekends. So I can't necessarily draw a direct causality to it, but I certainly do think there's an effect. Honestly, it's not that big of an inconvenience — if it helps me by 5% or 10%, I'll do it. I'm also... every year for my birthday I do something called "prenova." Do you guys know prenova?
12:24	Sam Parr	Yeah.
12:24	Harley Finkelstein	Yeah, I've been doing it for the last six years. My birthday is in November.
12:30	Shaan Puri	Go to New York for a pretty bad birthday one year. You gotta be careful with that.</FormattedResponse>
12:34	Harley Finkelstein	"I mean, that's the issue — that would be a buzzkill. The main issue with that is obviously false positives, right? I've just decided: I think entrepreneurs and founders tend to be on this side of the equation — I prefer a false positive to a false negative."
12:48	Sam Parr	"Right. Have you—maybe you could answer this. You're actually the only person I've asked this publicly, but I've never gotten a good answer. How can you be a billionaire today and be unhealthy? Like, how can you be a fat billionaire today?"
12:59	Harley Finkelstein	I would get rid of the billionaire. I think—forget the billionaire thing for a second, because I don't think you'll need to be a billionaire to do that.
13:07	Sam Parr	Do you know?
13:07	Harley Finkelstein	"Any fat billionaires? I do, but I don't want to say anyone's name right now. Of course you probably know them, too. But it doesn't make sense — maybe they have a thyroid issue. I do believe that if you have the means, and you can have, you know, housekeepers or a chef at home... If you have a chef at home, no one's going to tell their chef to make them 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's much easier to go 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 it's easier for you to be in better shape if you have the means."
13:51	Shaan Puri	See, this is why I'm an outlier. I defy all the rules. I have a personal trainer who comes to my house. Okay — I'll find a way. The will finds a way. Well... you know what? But, Sean... </FormattedResponse>
14:01	Sam Parr	It's bullshit.
14:02	Shaan Puri	I want to DoorDash something. I'll... I'm going to find.
14:04	Harley Finkelstein	Anyway, so if you—if you didn't have the trainer come to the house, you'd be in [in weight]. I suspect you'd be way worse off.
14:09	Sam Parr	Thank you. You have gotten way healthier over the last handful of years.
14:11	Harley Finkelstein	Yeah. When I had my first child — Bailey is now eight years old — Dave Siegel, who is a couple years older than me and had kids before I did, said something to me when I was having Bailey. He said, "Look, if you can afford to have a nanny..." He actually articulated it as, "It's gonna be a marriage saver." I didn't really understand what he meant at the time. What he meant was that everything is easier as a new parent at home. Shopify was already publicly traded and I worked 70 hours a week. He said, "If you can afford a nanny, you should do this." I didn't really know what he meant by the whole "it's a marriage saver." In hindsight, I now do. Some of the stresses that I think some people have — they don't go away, they just lessen when you have certain luxuries in your life. I grew up without money, so I didn't grow up in that world. I don't take that for granted, but I do see how things get easier.
15:05	Sam Parr	I heard an interesting story. Actually, last week I was with a person — I'm not going to name him — but he's a billionaire and a big-time investor. He was telling stories about Shopify. I was talking about how I met with you, and I said, "Man, Harley is so charismatic — it totally got me bought into Shopify even more." He said, "Yeah, man, I've met with Harley a bunch of times. I know him well. I've met with Toby a bunch of times. I've also met with the Collison brothers at Stripe a bunch of times — they're an amazing company." "He thinks they're roughly worth the same right now," he added, "but I think Shopify is going to be worth ten times more than Stripe." I asked why. He said, "Whenever I'm with the Collison brothers, we talk about interesting philosophical things, their hobbies, and things like that. 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. Because of that obsession, even when your company is worth $150,000,000,000 (or whatever it is), that still comes into play. It's not just market factors or market forces..." Is this the beauty of...
16:12	Harley Finkelstein	This founder-led thing... I mean, you know, I think the Collins and brothers are obviously a great example of founder-led companies as well. They're private, so you don't know the exact valuation of it. But I do think that 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.
16:29	Sam Parr	And I don't want to... I actually wanted to spend some of the time in the episode where I was like, "Actually, Harley — I know you a bit now, but Toby is still mysterious to me because I've never met him." He seems like... I think he has this one quote where he goes, "My wife says I'm an immigrant to the human condition." Yeah.
16:45	Harley Finkelstein	That sounds — that seems super. I mean, and to his credit, because he is so self-aware, he truly... 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) — you think of the phases of companies. At the beginning, in the first phase of a company, everyone needs to be a Swiss Army knife: everyone does everything. Then the second phase is more like what I call a "triple-threat phase", where... </FormattedResponse>
17:09	Sam Parr	Could you put a threshold on that? Like a number of people, or something?
17:12	Harley Finkelstein	Yeah, I would say—for us it was like zero to, I don't know, Dunbar's number. You know that concept? Numbers: 50 or...
17:19	Sam Parr	"One fifty."
17:19	Harley Finkelstein	Yeah—hundred, hundred-and-fifty-something, like that. It comes from tribal times, where that's how many people any human can remember at any one given time. So I would say 0 to 150 or so. I was kind of a Swiss Army knife in those days at Shopify. I did business development (BD), sales support, and partnerships. I built the Gap 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.
17:43	Shaan Puri	Better Call Saul
17:44	Harley Finkelstein	Yeah. We didn't have a CEO. We didn't have a CFO at the time or anything like that, so it was Swiss Army knife time. Eventually you get to what you might call product–market fit around the Series A or Series B, where more people can sort of slot into the right roles. Meaning: you don't do just one thing, but you do a couple of things really quite well. That was sort of my role as Chief Operating Officer, and so I looked after a couple of big organizations. We built a sales organization and began to think about different areas of product. Post-pandemic — so like 2020–2022 — a couple of things had to change for us. One was that we were bloated. We had about 14,000 people, and that didn't work. We brought it down to what we are now, which is around 8,000 people, and 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 "side quests" and the "main quest" — what are our side quests? Let's get rid of them. Let's focus on the main quest. The third thing that happened in this new phase of Shopify was these spiky objects. What that really meant was we basically brought in a new leadership team. As part of that process, Toby and I were thinking about the things we truly should be spending our time on — meaning the highest value for Shopify. That meant we kind of rearranged the company, not necessarily around traditional roles of "you do this," but rather based on our strengths. As part of that, Toby's not on the earnings calls anymore because I can do that. I think I can do that 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. This is my sixteenth year at Shopify, it's Toby's twentieth, and we've been public now for about a decade. But you can't get there right away — you have to go through these phases in order to figure out what your spiky object is.
19:38	Shaan Puri	That's pretty cool, and 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. So I think, even in this case — you didn't even mention it — there's a very telling thing: he didn't have the ego to say, "No, I need to be the frontman; I need to be the lead singer," even though he's actually the best drummer.
20:00	Harley Finkelstein	So Toby refers to me as the "lead singer of the band." I think a lot of companies throw around this idea of "mission." Shopify's mission is very simple: increase the number of entrepreneurs on the planet — that's it. We increase it by adding more entrepreneurs to Shopify who otherwise were previously only aspiring.
20:16	Sam Parr	Dude, do you hire people? If that's your mission, that's a hard thing to... all your employees would be fucking quitting.
20:21	Harley Finkelstein	Well, actually the best part is we end up hiring mostly entrepreneurs — people for whom entrepreneurship has deeply affected their lives. For me, my grandparents are Holocaust survivors. After the Holocaust they went to Hungary. In the fifties, Hungary got really bad — the Hungarian Revolution happened in 1956 and Canada let in 40,000 Hungarian immigrants. My grandfather came here with my father and his siblings. They came to Canada, and my grandfather ended up selling eggs at a farmer’s market his whole life. That egg stall, called "Le Capitaine," still stands today. It's about five kilometers from where I'm standing right now. 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: I grew up in South Florida and moved to Montreal to go to McGill when I was 17, in 2001. My dad was no longer in our lives, so I had to support myself, my mom, and my sisters. I started a T-shirt company. That T-shirt company eventually became an online T-shirt company, and I became one of the first merchants to use Shopify. That's kind of how I got here. Toby comes to it in a very different way. He's an immigrant who lived in Germany, met a wonderful woman who became his wife, Fiona, and moved to Canada. As a new immigrant he couldn't get a job and wanted to start a snowboard shop, but found it incredibly difficult to do so. He wrote a piece of code to sell those snowboards, which would then become Shopify.
21:43	Shaan Puri	You know, our buddy George Mac has this great phrase where he says, "People only remember 'you're weird.'" He means that any behavior that's standard that you do might be very useful, but it's not very memorable. </FormattedResponse>
21:55	Harley Finkelstein	Yeah.
21:56	Shaan Puri	And so, Sam was asking about Toby just now. I think, as he said, Toby is a bit of a "mysterious character." He's not someone who's out there doing a bunch of podcasts or public things. I'm curious: what are some stories of his weird—what's a behavior or a thing that he does that's nonstandard?
22:14	Harley Finkelstein	There are a couple of things that I think define his leadership at Shopify. One, fundamentally, is that he spends a lot of his time using all the newest tech. He's constantly reading the newest white paper on a new LLM that just came out. I don't think that's uncommon — you'd see that with Patrick or Zuck — but there is a category of super-technical founders that didn't exist historically. At least, if they did, they weren't running $100 billion or trillion-dollar companies. Tobi is in this group: super technical and often more familiar with the codebase than anyone else on the planet. The other important thing he does every year is set priorities. During Christmas break he spends his time effectively running the company's priorities. On January 1 every single year — for the last decade or so — the whole company gets an email with incredibly specific direction about what we will build that year. It's not necessarily based on surveys; it's based on his deep intuition about how the product needs to evolve. Sometimes that means preparing for extreme traffic — Shopify runs some of the largest flash sales on the planet (for Supreme or Taylor Swift), with crazy throughput, like 30,000 transactions a minute. Other times it's broader: the future of retail won't be just online, it will be everywhere, and Shopify has to make it super easy to sell across every surface. I announced two weeks ago that we're working with Roblox — embedding commerce into that universe. Tobi didn't say, "Go do Roblox." What he did say was: make sure that everywhere consumers spend their time, our existing merchants can easily turn on that channel. I forgot the exact DAUs, but it's ridiculous — I think there are about 700 million monthly users in the metaverse, and the largest chunk are in Roblox. It's roughly a $100 billion industry today and could be about $930 billion in ten years, by 2030. That's the type of strategic intuition he brings. He does talk to customers, but what he's incredibly good at is that intuition. The second major trait is that he spots talent really well. He finds unobvious people across Shopify and gives them the room to do their best work. He can completely ignore an org chart and focus on impact. He might see someone on GitHub, like their commits, and think, "I like the way they wrote that," and then elevate that person, giving them something much bigger and more creative. Finally — and we touched on this earlier — what he's done for me personally is that he sees a better version of me than I even see. I've always been fairly confident in my ability to improve, but he always shows me there's a new gear. I think I know I'm in fourth gear, and he points out there's a fifth gear I haven't discovered yet. His expectation of me, and frankly of the entire team, is that we "requalify for our job every year." He expects that of himself too. He puts more pressure on himself than he puts on anyone else, and I think that's an amazing thing.
25:42	Sam Parr	Does someone like him evolve into this... 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?
25:52	Harley Finkelstein	You know, I think a lot of people end up starting companies and spending their lives working with people 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. Remember, I came to Shopify as a merchant first. I moved to Ottawa in 2005 to go to law school—not to become a lawyer. A mentor of my T‑shirt company from college at McGill (here in Montreal) had built a pretty successful T‑shirt business. I was able to pay for my tuition and my rent and help my mom and my two sisters, who were going to private school; I was helping to pay for that. I was paying my mother's rent. A mentor convinced me to go to law school—not to become a lawyer, but because he saw law school as finishing school for entrepreneurship. He was a lawyer and he taught law at the University of Ottawa. He said, "Come to Ottawa, go to law school here. You're never going to practice law, but I think it will make you a much better entrepreneur. You'll learn how to reason critically, how to write better, how to think better, how to articulate yourself better." So I moved to Ottawa with no friends. I'd never even been to Ottawa before—it's the capital of Canada. I got there and thought, Where are the entrepreneurs? Those are my homies; those are the people I always hang out with. I met Toby through that. At the time he was just transitioning from snowboards to software, and this was before I ended up becoming an early merchant. Even in 2005, he was thinking about what the future of the internet might look like.
27:15	Sam Parr	So, do you remember? Can you give us a bunch of those quotes?
27:18	Harley Finkelstein	Yeah, I remember him. I remember him saying, for example, one of the things that — like, payments should have been built into browsers. I was like, what? He said, "Yes. The people that made browsers completely fucked this up. Payments should be natively integrated, not through a third party, but natively built into the browser. Identity should be built into the browser entirely." 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 he had done that I thought was incredibly inspiring — as someone who, you know, worships the altar of entrepreneurship — was this: 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, which ended up getting acquired by Salesforce. There was a company called ATG, which ended up getting acquired by Oracle. There was a company called Hybris, which ended up getting acquired by SAP. Those were the main players. There were some others too, like Yahoo Stores, but no one was really doing major GMV or volume on those. I remember him telling me that the problem with all of these companies is that they're built for existing entrepreneurs. There's never been anything built for aspiring entrepreneurs. Meaning: if you have an idea in the shower in the morning, you should be able to go to your desk and get it going right away. What if we were able to give the smallest entrepreneurs — the smallest companies, the smallest ideas — the same tools that traditionally only the biggest companies could have? What would happen then? Well, the end result is that we've now transacted over a trillion dollars on Shopify. Yes, we have some very large stores, but the majority of that GMV is the long tail: small businesses and homegrown success stories. Companies like Fashion Nova or Gymshark — all of these started at their mom's kitchen table and grew super, super large. Those are a couple of the things in the early days that completely changed my perspective on how to think about building. Remember, 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 Ireland. And I'm like, for $29 a month.
29:27	Sam Parr	I think.
29:27	Harley Finkelstein	It was $24 a month at the time. That was a dramatic insight for me: 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.
29:43	Sam Parr	Where—where has he been wrong? Where's the weakness? Where's the human side of...
29:47	Harley Finkelstein	This—yeah. So he's... because it sounds amazing. Are you guys familiar with the Enneagram? Yeah? Okay. So the Enneagram is this sort of—there's a lot of these personality systems. The Enneagram is the only one, frankly, that I think is worth any review. But he is an Eight: the Challenger.
30:02	Shaan Puri	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. </FormattedResponse>
30:11	Harley Finkelstein	Okay, now go to three.
30:13	Shaan Puri	The Achiever — self-assured. What is it? Self-assured — attractive. There you go: charming, ambitious, competent, energetic. At their best, they are a role model who inspires others. But they have basic fears of being worthless and a basic desire to feel...
30:27	Harley Finkelstein	Oh, that hits, man. That hits. First of all, for anyone listening: if you are working in a team with a bunch of different personalities, it's a really effective thing to do to actually figure out what they are on the Enneagram. We've looked at them — I've looked at every one of them. We've had coaches on staff at Shopify for over a decade. This is the one I think is the most valuable. Knowing that Toby, being a challenger and an achiever, he is really tough. 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, 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. That is why he should be... you know. I will work at the company as long as he'll have me and as long as he's there, 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? I've talked to peers at other companies; they say, "There is not a softness, but there was a collegiality to their culture." That doesn't happen at Shopify. It's not that we're not collegial — it's just that that's not what we're trying to achieve.
31:45	Shaan Puri	Did you guys ever have acquisition offers? You talked about how Magento sold and this other guy sold. Was there ever a moment—when everybody sold—where you had an offer or a discussion you had to take seriously, and you faced a fork-in-the-road moment? You obviously ended up independent, but was that always the case? Was that the only way this could have gone?
32:04	Harley Finkelstein	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: first of all, we did not return phone calls from corp dev teams early on. [corp dev = corporate development] Specifically, we didn't want to get into that headspace or that line of thinking. It wasn't what we were interested in. We wanted to build a hundred-year independent company, and we knew those phone calls might lead to meetings, conversations, and consideration. We just didn't want that in our minds — it felt like a real distraction. You guys know this too because you both invest in a lot of companies. Once you take that phone call from a corp dev person at a big company, you begin to inadvertently — or advertently — start a process in your mind of "what if": "what if the number is right," "what if the terms are good," "what if there's a space for me at this company where I can..." The pitch many of these big M&A conglomerates make is: "You can do what you're doing at your current company, but you can do it here with more scale." Ultimately, we didn't want to even have that in our minds, so we didn't return those phone calls. Second, we went public at a very early stage because, one, we thought it would be the best way for us to be independent longer term, and two, we felt the company was ready — the product was ready, the business was ready, the team was ready. That's not really the case anymore. There are two companies I'm very close with: one is Klaviyo — Andrew, who's the founder of Klaviyo, went public last year — and then Fidji, who at the time was CEO of Instacart and who's on our board, went public as well. So you've had a couple IPOs. Generally, in the case of most of these companies, they're much larger — they're in the tens of billions of dollars of market cap — before they actually go public. So, again, we just didn't want to get acquired; we wanted to be independent.
33:55	Sam Parr	But were there ever times where you were like, "I would like to take this deal; this would be nice"?
34:00	Harley Finkelstein	"No, there truly was not. We did — we did a very small secondary on, I think, the Series B, which basically allowed me to buy a house: a down payment on a house."
34:11	Shaan 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"? What's your philosophy around that? Because it's tricky, right... even if you believe, yeah.
34:20	Harley Finkelstein	Money. Money is so—money is 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. Growing up, money felt emotional to me. Some weeks we had it and some weeks we didn't. We never, you know, we always had food on the table, for example, but there were times where I remember as a kid my mom would come to me and say, "Hey, we're gonna have to tighten our belts this month." That tightening of the belt happened a lot during my childhood. 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 plan, 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 Shopify. I've taken money off the table so that I feel like my family is secure, my children are secure. We're never gonna have to tighten our belts, and that's 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.
35:26	Shaan Puri	What was the hardest—what was the hardest moment at Shopify? Was there a "rock bottom"? What was the low?
35:31	Harley Finkelstein	"Whoo. COVID was really, really hard. Maybe not for the reasons that, you know, you guys — I mean, remember: Shopify went from something like... I don't know, maybe pre‑COVID we were a $30 billion company. We, like, overnight..."
35:47	Sam Parr	"I have your revenue. I think in 2019 you're at 1,600,000,000, and then in 2020 you're about 3,000,000,000."
35:54	Harley Finkelstein	That's a big jump, and it was a big jump in everything. What happened during the pandemic was— I mean, e-commerce as a percentage of total retail was sitting around 15% in the US. So, 15% of all retail was online. Then, effectively, you had this pull-forward during the pandemic where we jumped very quickly to the 20-something percent range.
36:11	Sam Parr	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 $200 million. </FormattedResponse>
36:17	Harley Finkelstein	Yeah, can I finish my fucking story, guys?
36:19	Sam Parr	Okay, so...
36:21	Harley Finkelstein	So there was this manic period inside Shopify. All of a sudden there was a pull-forward effect: laggards who had been purely physical retailers needed to go online, and they moved quickly. It was like, "just get shit done." Then 2022 happened and the market started moving the other way. We found ourselves with a much larger team and a lot of side quests. Shopify also, for the first time ever, I think, was not profitable. That sort of post‑COVID hangover was really tough for us. That's where the next phase came into play: we needed to figure out what we cared about, what the right team size was, and what our focus areas should be. We had to make sure we had the right people leading the company. We recalibrated everything. It was really hard. I knew Shopify would make it; I wasn't sure if I was gonna make it.
37:22	Sam Parr	Was there ever a time where you thought that Shopify wasn't going to...?
37:24	Harley Finkelstein	Make pre-IPO for sure. I mean, post-IPO things... you know, we went public at a time when we sort of knew what the next ten years would look like. We were profitable. We were making money. We were, you know, subscribing to this whole like—"grow top line and also grow bottom line." But pre-IPO—that was hard, right? I mean, we were bootstrapped for a while. There were times when we didn't know if we could cover payroll. But, you know, I think you have to be a little bit crazy—naive. </FormattedResponse>
37:52	Sam Parr	Sean and I—my last company—we were going to do about $17–20 million the year we sold, but I sold early in the year. Sean has a business that is, you know, he's got his hands on a bunch of things that are potentially in a similar range. I don't want to speak for him, but I don't think either of us have experienced this $50–100 million range where I'm like, "Oh, then I could just manage three amazing people who do most of the work." I'm in the phase now with my business where everything is fucking hard. If someone—dude, someone quits, I have to go do the work. So what I want to know is: does it get more...
38:25	Harley Finkelstein	Does that go away?
38:26	Sam Parr	"Does it get more fun?"
38:26	Harley Finkelstein	No, no, it doesn't. But actually, I don't think any of this gets easier — you just have different problems. It's like the... the magic number. We all have this magic number early on as entrepreneurs, especially if you grew up the way that I know—Sean, Sam, and I grew up the way we did. We all have this number. "On my roof, when I get that, I can... I can basically extrapolate my passive income from it and that's gonna pay all my expenses that I can do." [speaker referring to a personal benchmark] Then you hit the number and you're like, "It's bullshit. It's complete bullshit." There is no magic number, just like there is no stage of a company where you are cruising — it's just different problems, right? So the problems that I have at, like, 7,000 people and a $100 billion market cap are very different than what I had with, like, 70 people.
39:07	Sam Parr	Which problems do you enjoy more?
39:09	Harley Finkelstein	This is my favorite stage of Shopify. Going back to the whole "spiky object" — the thing I think I can add, the way I can add the most value to Shopify, is through storytelling. I believe the microphone I have now because of Shopify's size allows me to do it at this crazy scale. For that reason, my life's work gets to be more amplified today than it did ten years ago.
39:32	Sam Parr	I remember—you've always been lyrical and good at talking. You are now much better. Always—you've always been good. Now you are, like, really great. Do you have, like, a writer? Is there someone who's going to watch this and be like...?
39:44	Harley Finkelstein	This bit hit—no. You guys asked me for notes. You guys asked me for notes this morning. I had to literally sit down and write you notes myself. No.
39:51	Sam Parr	We didn't use that name.
39:52	Harley Finkelstein	Yeah, exactly. I don't even think... I don't even know what I wrote to you. Wait.
39:55	Sam Parr	What did Sean say?
39:56	Shaan Puri	I DM'd him this morning and was like, "Hey, saw that... excited for the pod today." I said the best episodes tend to be where guests come in with three or four bullet points. I gave him some guidelines and mentioned I noticed he hadn't filled out the prep doc we usually send guests. We send a prep doc and they fill it out, and it gives us some options for where we can go in the conversation. He replied, "Prep doc? Dude, let's just hang." I said, "Oh, yeah... I gotta be cool. Okay, my bad."
40:27	Harley Finkelstein	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 are no notes.
40:33	Shaan Puri	There's no "but you should." I actually heard a couple of stories recently that have really inspired me. Okay — I'm going to give you a little framework that I think most people underestimate. There's a story in sports that LeBron James spends $1 million a year on his body. The number is actually kind of irrelevant, but the idea is directionally correct: LeBron spends a lot of money on his body. He has treatments, coaches, and protocols that the average athlete does not follow. In fact, we went to an NBA team and I asked, "How many of you have chefs?" Less than half the team raised their hands. I was like, "This is insane — I couldn't believe the owner would even allow that." For LeBron, every meal is dialed. Every hour of the day is either recovery, building, or playing. LeBron does that in his field. I then talked to somebody who knows Peter Thiel very well. It's weird because Peter is not a smooth talker — he stutters and stumbles. But when Peter Thiel goes on tour, every seven to ten years, he's got a message and boom: he gets a ton of PR. His message is very effective. He's not very efficient with words, but he's very effective. If you remember, he did one where he said, "Universities are a bubble."
41:47	Harley Finkelstein	Yeah.
41:47	Shaan Puri	Right. He went on a whole tour of that, and then he launched the Thiel Fellowship underneath it. He did one called "Competition Is for Losers." He has these slogans—almost like marketing slogans—like "Competition Is for Losers." Then he launched Zero to One, his book that was all about how to build a monopoly. When Trump first ran, he said, for founders, "We wanted flying cars, but all we got was 140 characters." Now, Peter did not write that line. In fact, what my friend told me is that Peter Thiel kinda has a guy who follows him around, listening to all of Peter's thoughts and then sort of workshopping his bits—like a comedian would, like a politician's speechwriters would. They actually craft the message, write it out, and basically get him prepped for media. He's not showing up and just winging it—because maybe he's not that great at winging it. David Rubenstein does the same thing. </FormattedResponse>
42:33	Harley Finkelstein	He — I know David. So David actually has an even larger team because he does the show and he does the TV show, and he's obviously with Carla and stuff. I don't necessarily have a writer per se. I do have people who kind of remind me, like, "Hey, remember that — this is kind of the direction." I'll give you the best example: earnings calls. I meet with my Jeff Hoffmeister — amazing, amazing CFO. I meet with Jeff and our IR team, and I'm like, "Alright, what are the three or four things that we want to say?" Then I basically take it, and I, you know, hardly revise it. I make it sound like me.
43:03	Sam Parr	So, can you give an example? An example is like, "We..."
43:06	Harley Finkelstein	"Wanna get? We wanna be."
43:07	Sam Parr	On Roblox, or something.
43:08	Harley Finkelstein	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 want to sell in Roblox if you're selling hand sanitizer. But if you're selling another product and your audience spends time in Roblox—or in some sort of metaverse—you may want to access it. By being on Shopify, you are, by default, selling everywhere.
43:33	Shaan 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."
43:38	Harley Finkelstein	We're also on Pinterest and Instagram. There's literally a Spotify–Shopify channel where you can actually—if you're large, if you're Beyoncé and you have an artist profile the size of Beyoncé—you can sell "Sacred," which is her cosmetic line, on Shopify inside of her artist profile.
43:53	Sam Parr	"And rumors are you're going to be on Chatuchipi Tea."
43:56	Harley Finkelstein	That's rumors, yeah—we're not going to go there today. But exactly: we want to be wherever you effectively have consumers. Earnings were three weeks ago. I love earnings. I do my earnings call, then I do my analyst calls, and then I do my media tour. In this case I did TBTN, which I think those guys are killing it. I did CNBC and some Bloomberg stuff. I noticed that there were a bunch of other companies—I listened to earnings calls a couple days before and a couple days after—just to hear the tonality of the reporters, the journalists, and also the executives. Sebastian from, I think, Klarna basically came out—after his earnings call he said, "the whole thing was done by AI; it wasn't even me." It was basically an AI emulating his voice, and that's who did his earnings call. That actually made a splash; there were a couple articles about it. I listened to it and thought, yeah—that's like a five out of ten. Maybe you can say it's a six or seven out of ten because he saved a lot of time, so it was effective. But in my view there was zero personality to it. Then I watched a bunch of other so‑called professional executives who did their earnings calls—the P&G guys, for example, or the folks over at Best Buy. I listened to their earnings calls and they sound like they're reading a script. If you go back and listen to ShopLite'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 they'll use voice inflection, repetition, and so on. What I hear back from analysts and investors is that they find our earnings calls so much more interesting because what they actually hear is our personality. They hear the passion in my voice—they know we give a shit about this stuff too. So I think there's probably a right balance: have people around you giving you the macro things, but if I start talking like Peter Thiel, it's not authentic and I don't think it'll be as effective. I've done 40 earnings calls now. The balance I have is: tell me what the most important things we need to hit are, and then let me find my own way of negotiating those into the call.
46:06	Shaan Puri	Right. I like that — you studied the game film of the other earnings calls. That was what I was looking for: that kind of extra effort you go to that others may not have.
46:14	Harley Finkelstein	People that... I mean, Benioff's fantastic at it.
46:17	Shaan Puri	Do you... So, Toby came out with this memo that said, "Hey, it is a baseline expectation."
46:23	Harley Finkelstein	He didn't come out with it. It was leaked. But yes — yeah, it was leaked. Someone leaked it.
46:26	Shaan Puri	I always assumed those were potentially leaked. I would have intentionally leaked that if I were him.
46:29	Harley Finkelstein	I think, in hindsight, some of these things—when they do get leaked—you're like, "you know, a blessing, for better or worse." Kind of thing. But yes.
46:35	Shaan Puri	But then... he was basically like: > "Yo, AI is an expectation based on expectation. You gotta learn these tools. The way to get good at them is to use them a bunch, and you gotta start solving problems using them." This was the general ethos. I'm curious— you personally, Harley, day to day, what's your AI usage? Are you, like, a lot, a little, just ChatGPT, other tools? What are you actually personally using, either professionally or in your personal life?
47:00	Harley Finkelstein	Things. One is: I use ChatGPT. I really like the fact that now it's got a history side. For example, back to longevity—every time I get a blood test I upload it into a ChatGPT folder called "longevity and health." Now I can ask questions. Although I do find that if I say, "I had a blood test last week; I uploaded a new one—compare this to my last one," it sometimes compares it to one from a long time ago. So it's not 100%, but I like using that quite a bit. I gave a keynote at Summit last week. I literally fed my entire keynote script into ChatGPT and I said, "Hey, what parts of these do you think are confusing, if any? Where am I losing the thread here?" I use ChatGPT—particularly the O3 model—on a daily basis. I have two screens, and based on the screen next to me I always have that open. I really like Claude for other projects. For investing, for example—Lynn's my wife and I do a little bit of investing; we own some apartment buildings—so I have a file for real estate. 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 ChatGPT is much better for reaching out into the public sphere, like the web, and bringing things together. Those are the two I use the most. Back to earnings calls: one of the things we did was we basically made all of Shopify legible and we built about a dozen MCPs inside of Shopify. Usually in preparation for an earnings call I will go to, let's say, I want to talk about Shopify Capital. I'll go to the capital leader and say, "Give me a couple of the highlights for the UK; it's new for us; I want to talk about how it's going this time." This time I went to the vault and literally went into the capital program—because everything is legible I was able to pull most of the data on my own. The jury's still out on whether or not I'm missing things. 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 actually I'm going to take that and run with it—even though you didn't intentionally mean to leak it to me or tell it to me. Using the Shopify vault, which is where 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.
49:18	Harley Finkelstein	One of the things that got missed in Toby's memo/email is a term he used that I'm surprised more people haven't picked up on: AI being "reflexive." Part of what he's trying to get the company to do is to be reflexive about the usage of AI. Rather than treating AI as an afterthought—"I have a project, and now I should also use AI to see what I can get from ChatGPT, Claude, Anthropic, or Complexity"—he wants AI to be reflexively part of our day-to-day work. That idea of making AI a built-in, reflexive part of workflows is really what he was trying to do. In fact, he went so far as to create a new friction: before you can hire someone on your team, you first have to substantiate to Shopify—the hiring manager and the talent team—why AI cannot do the work better. We're noticing that by creating this friction—requiring that you try AI and justify why it can't replace the role—people often realize, by the end of that substantiation, that AI can actually do a lot of the work. That approach is very different from what you hear in most companies, which is more like: "Let's just use AI as part of our process—if I have to design something in Figma or Canva, I'm going to use AI to help with that." The idea of AI being reflexive is sort of what we're trying to do. </FormattedResponse>
50:31	Shaan Puri	I like that a lot — that's cool. That's a great little nuance and sort of a tactic. I like these sorts of incentives or systems where you do one thing and it has all these downstream impacts. Right now people are talking about the U.S., like, "Oh, the deficit — so crazy." Buffett has always said this thing: "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."
50:55	Sam Parr	"That's right."
50:55	Shaan Puri	Watch, watch what happens. I...
50:57	Harley Finkelstein	I mean, you get to do that at companies. Back to the phase of the company—at the phase of size and scale of our company—we get to do stuff at this crazy scale. Simply by adding a small friction on hiring that says "first, substantiate it," you actually see incredible results. Then you can evaluate. You can literally ask, "How has hiring changed since that email was leaked? How has hiring changed since we added that friction?" It's very difficult to actually see the efficacy of all these things when you're ten people.
51:27	Shaan Puri	You look really healthy and have a lot of energy. I'm curious: you said you got curious and became interested in biohacking/longevity. You're on a kick right now — what's got your interest? What are you doing that you feel is either interesting, working for you, or that you're enjoying? Just give us kind of a quick health dump.
51:43	Harley Finkelstein	So I sort of divide it into two buckets: I'm going to die one of two ways — either from cancer or from a heart attack. The cancer thing isn't easy, but Prenuvo [a full-body MRI service] does a lot of the heavy lifting for me. I'm 41 now, so I'm taking it a lot more seriously. I get checked once a year. Prenuvo's not the only company, but I like it a lot. I like it so much that my wife and I actually invested in the company a couple of years ago. I think the way they do it — and the way the technology is moving — is interesting. A lot of people don't like going into these full-body MRIs because they get claustrophobic. Part of Prenuvo's product is that you put on these glasses that have mirrors; the mirrors project backward onto a screen. I watch the most fun, light show I can find. For me, that's Seinfeld. I'm not claustrophobic, but I don't want to stay in something like that for a long time.
52:36	Shaan Puri	Dude, when I went in, I watched Top Gun. I was like, "Oh—what's a movie I should have watched but never did?" I just watched Top— I mean, Top Gun. Did I?
52:43	Sam Parr	I'm like, I...</FormattedResponse>
52:44	Harley Finkelstein	Do not want to be stressed out. Don't want to be scared.
52:46	Sam Parr	Dude, I watched the Zodiac Killer documentary on Netflix. It was great.
52:49	Harley Finkelstein	You — I mean, that speaks volumes about both your personalities. I watched a personality test, and that sort of takes you on the cancer side. On the cardiovascular stuff, I just did a CT scan, which basically looks at blockages. What I was trying to do initially was get a baseline of where I am right now. The reason I like Prenuvo each year is because I can look over time and see how things are changing. If I have a benign cyst on my liver, is it growing year over year? Now at least I can monitor that stuff too. To me, those are the two main buckets. Then I try to do these mini-goals — one thing every year that scares the shit out of me. The thing I really like right now is called 29ZERO29 — Jesse Itzler's program. Jesse has done an amazing job. He and Mark, his partner/co‑founder, have created this incredible program that effectively allows you to climb Everest without having to travel to Everest. You can do it from places like Colorado. In my case I do it in Quebec — in Mont‑Tremblant. You can also do it in Vermont. They've created an experience that lets you emulate climbing Everest locally. I've been doing this — this was my second year. I like doing it not just because of the high‑five; it's cool to emulate climbing Everest. I also like getting really scared that I'm going to fail at it, because that makes me train much harder. So my workouts are actually much better because I'm so scared of failing at this 29ZERO29. </FormattedResponse>
54:16	Sam Parr	"Dude, last question: how many—how many companies in the world are bigger than Shopify? You guys are worth... it looks like $1.53 today or something, or $1.30—whatever. You've been as high as..." </FormattedResponse>
54:27	Shaan Puri	One thirty-four.
54:28	Harley Finkelstein	200 — you're surrounded down by 20,000,000,000. Just wanna...
54:31	Shaan Puri	It's casual.
54:32	Sam Parr	Casual — what's crazy is, you're worth $134,560,000,000.00. Change that $5.06 to $5.05, and that's life-changing. You know what I mean? It's kinda crazy.
54:43	Harley Finkelstein	For sure.
54:43	Sam Parr	No, it's wild.
54:44	Harley Finkelstein	Look—let me call out one more thing: if you were listening to this and you were a company that actually understands your business well and you see great growth potential, this idea of avoiding the public markets is insanely silly to me. It's been an incredible forty, forty 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 to feel more confident. I mean, now we have companies like Hunter Douglas, Mattel, and Birkenstocks using Shopify. I think one of the things they love about it as a product is that being publicly traded provides some sense of stability.
55:19	Sam 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 history—given that today's companies are bigger than everyone else—you are in the top 150. It's pretty astounding. And I think that, like, if there was a ratio of somehow most relatable or some reason—when I talk to you I'm like, "he's just one of us." He's like one of us. "I hate him—that's why we're friends."
55:50	Shaan Puri	"Fuck, he's not one of us. Damn it."
55:52	Sam Parr	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. Oh—what do...</FormattedResponse>
56:00	Harley Finkelstein	You mean, you know me personally? We've—like, I think I said this at the beginning, right? I was, I guess, 18. We're the same.
56:07	Sam Parr	My friend, we are...
56:07	Harley Finkelstein	Not "we are."
56:08	Sam Parr	And now you've...</FormattedResponse>
56:09	Harley Finkelstein	Had over 750 of them.
56:11	Sam Parr	We are not the same. But if there were a ratio—like, I feel like I could do whatever he's done, too.
56:18	Harley Finkelstein	Approachability-to-market-cap ratio
56:19	Sam Parr	"You are — you get the gold medal." </FormattedResponse>
56:22	Harley Finkelstein	"I think that's the sweetest thing you've ever said to me, Sam."
56:24	Shaan Puri	You know what's one of the best things I did after that first podcast? Basically, every year for the last five years I take about 20% of whatever my profits are from my Shopify store and I just buy Shopify stock.
56:35	Harley Finkelstein	"Oh, wow."
56:36	Shaan Puri	That's cool. That alone, I think, has compounded as well or better than my actual "Thanks, John" ecom brand, because now my earnings are growing. Whereas if I just reinvest it in the business — and not every business can reinvest 100% of your profits back into it — just that one little habit has been very, very...
56:53	Harley Finkelstein	Helpful for me — well, it means a lot to me. It's actually really neat. We're doing this thing called Chocolate Milestones. Basically, it's our version of the Emmys or the Oscars for actors, or the Grammys for musicians. We give out these milestone awards. You guys have probably seen them around. This is the 10,000 one. We get it for 10,000 orders, 100,000, and a million too. </FormattedResponse>
57:10	Shaan Puri	Y'all are so slow. I got my milestone, but I'm already on the next order of magnitude. Like this—yeah, it's so slow. How... how did you guys set these out?
57:16	Harley Finkelstein	I mean, they're heavy. We had to ship them out and stuff. There are a lot of people. But anyway... I get to deliver — that's...
57:21	Sam Parr	"The most efficient" — that's your excuse. "Yeah, they're right. Heavy, yeah." </FormattedResponse>
57:25	Harley Finkelstein	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 that — obviously — they built their business on Shopify, but many of them are also shareholders, which I think is an unbelievable endorsement. It's one thing to use the product and build your business on it, but then also to invest your hard-earned money into it.
57:46	Shaan 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..." </FormattedResponse>
57:53	Harley Finkelstein	You sounded way less romantic than I did. Yeah — it just started to kinda...
57:56	Shaan Puri	Let's be real here, dude. Thanks for coming on, man.
57:59	Harley Finkelstein	Dude is great. You guys are the best.

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Shopify President: While Everyone Chases AI, Sell These Products

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