Harley Finkelstein: President of Shopify – Democratising Entrepreneurship, Empowering Founders, & the Tools That Build Global Businesses

27:33Yeah. Can you tell us a bit about those moments and what held you to Shopify for 16 years? So I think we're pretty close to Wall Street, right? We are. So, a stone's throw away from here. Ten years ago, almost to the day, I got on the podium with Toby and our team, and I rang the Bell at New York Stock Exchange to take Shopify public. And without any, I say this with no hyperbole, it was from an entrepreneur's perspective, it's one of the greatest moments in an entrepreneur's life. that you are standing at the podium where Henry Ford stood, where the most iconic entrepreneurs stood to take their companies public.

28:14And you have these sort of moments in the journey. And again, some of them are these moments of like ringing the bell to the stock exchange or doing something that is so Black Friday, Cyber Monday, 2024. At four o 'clock in the morning, I went up in a helicopter. We rented out the Sphere in Vegas and we projected global sales on Shopify. We did about$11.5 billion, a billion with a B, in four days on Shopify during Black Friday, September Monday, 2024. And I'm in this helicopter, and we're taking video, and I'm just like, I'm literally holding a microphone, and I'm just like thanking the entrepreneurs, the merchants on Shopify for trusting us.

28:54And then I'm like, and then I turn the camera, and I'm like, and this is the result. and it's like the Vegas sphere lit up and it's these tiny little dots like you saw and you see exactly where the order was and where it's being shipped to. It was unbelievable. There are moments like that that you absolutely remember and have to put in your pocket and you're sort of, you have to put those in your own personal vault because running a company of scale is really, really hard. And you have to requalify every year and you have to keep getting better at it. But I also think that that's the value of finding something you love much early on.

29:36There's these different phases of companies and the phase of the company that Shopify is in right now is really like we are spiky objects. We are not generalists. I know you talk a lot about general. You think a lot about this. You and I have talked about it. We are not generalists at Shopify. We are, can I swear on this podcast? We are the Avengers. meaning like all of us have one particular superpower and if we were by ourselves it wouldn't work as well but when you combine these when you combine these sort of superheroes you get the avengers and together like they're unstoppable and that's kind of how i think about skill set and skill acquisition and i think one of the most important things for people that are starting their careers to figure out is like what is going to be your thing and um so shortly after the IPO not too far from here.

30:22I became chief operating officer of Shopify for about six years and I liked it. I thought I was getting good at it. I don't think I was world class at it. And that nod at me because I didn't think I'd be able to do that for indefinitely. It did feel like that had at some point an end date. And eventually after talking to Toby and talking to my wife and talking to like my mentors people in my life that i look up to and i could take advice from it was clear to me that okay the reason i'm feeling this way is because this is like i wasn't doing the thing that i i felt i could be world-class at which is storytelling and what's really wonderful about having a company of scale now is you get a chance to to sort of put on a bunch of different hats and try different roles and the thing that made me like you know the term Ikigai?

31:14Yes. It's Obsession in Japanese. Exactly. That's right. Ikigai is actually a little bit different. Obsession is part of it, but it's like, what do you love? What are you obsessed with? What is the world value? What can you get paid for? It's like sort of this Venn diagram overlap of a bunch of things, which loosely also resembles life's work. And it was clear to me that the Ikigai thing, for me, was like storytelling. That where I had the most impact on the company in terms of our merchants and customers, the investors, the culture of the business was when I was storytelling. And so I've been able to architect a role that Shopify gets more from Harley, but Harley also gets more from Shopify.

31:50And ultimately, if you can find that and you know it that is early in your life, you get to spend a long time perfecting it and sharpening that point. it's really difficult because when you're in school at Lisa McGill when I was in college there wasn't a specialization you take like political science, you take some science courses there's all these pre-reqs and you're taking kind of a general sense of things and eventually you get to pick your major but even that, your major is not really precise if your major is finance you're still doing eight different types of finance this is sort of where I think, this is the value of having side hustles when you're in college and side hustles when you're a teenager.

32:30Because what was clear to me even those early days when I was DJing and selling t-shirts was, I don't know what I'm going to do, but it's definitely going to be something related to entrepreneurship and in my case, storytelling about entrepreneurship. At what point did you realize that you had this love for storytelling? When I started doing it on nights and weekends. When When I had any downtime, I didn't have a lot of downtime, I still don't have a lot of time, but anytime I had some downtime, I would do that. We have a concept at Shopify, which is really about this idea of like a main quest.

33:04And when you work at Shopify, we ask you for Shopify to be your main quest. You can have other things that give you great pleasure. Obviously, family is important. You may have a hobby to really love, but Shopify has to be your main thing. And whenever I had sort of downtime, I just, that's kind of where I found my, what I found myself doing. I also, through the IPO, which ultimately the IPO, the public offering, yes, you make your shares available to the public markets and anyone can invest. And now obviously, you know, anyone can participate in your growth. But also, I think the thing that gets missed about the IPO, and I talked to Rich about this, which I don't think Fashion will ever be a publicly traded company.

33:46I just don't think that's Rich's style. But I've told him this a number of times that one of the best parts of the IPO is that it's a storytelling opportunity. that it allows you, you go on the roadshow. And for us, we did like 93 meetings on the roadshow in 2015. And every one of those meetings with these big funds, Fidelity and T-Row, all these amazing, iconic funds. What was the meeting about? They knew what our financial statements looked like. They knew about the business. They already, they had all the public available documents. It was all in the F-1 or the S-1. We were a foreign issuer, so it was called an F-1 for us.

34:18But the S-1 is out there. The book is out there. What was those meetings about? They want to hear from us our conviction. They want to hear our vision. They want to hear our ambition. They also want to hear the voice inflection and the enthusiasm in our tone about why we think Shopify could be a much larger company, could be this generational company. And at the time, we were a billion-dollar market cap company when we were public. Today, we're over$100 billion. They wanted to hear how we're going to get from, you know, a billion to$100 billion. dollars. And it actually, in many ways, it's almost like paradoxical or at least, um, it's wrong term.

34:56It's, it's surprising to say this out loud, but actually I think being a public company has allowed me to become a much better storyteller and has allowed me to add more value because the audience that I have is a global audience. Whereas if we were a private company, I don't, no one would care as much, but if you can find that thing, that, that, that pointy object, that pointy edge, that superpower early in your life. And it may be, you know, maybe making great videos. It may be art. It may be, you know, I mentioned this earlier, but James Purse, who I pretty much most of the clothes I wear, he's my Loro, you know.

35:32Loro to you is just James Purse to me. I've known James for a long time, powered by Shopify. There's no one in the world to me that cares more about black T-shirts than James. Nobody. And the fact that somehow in the world that this guy can actually create a career around black t-shirts. I love that. Because 30, 50, 100 years ago, if he was creating black t-shirts, he would never have this scale because he would never have the opportunity. Or he'd end up going to law school or something like that. Or becoming a banker or something like that. So I think finding your thing early in life and then sharpening it during your career, as opposed to what I think a lot of people end up doing is they end up retiring later in life, and then eventually they end up finding their life's work in retirement.

36:26I think the earlier you can find it, the better off you are. I love that you mentioned that James Purse is powered by Shopify because it is, in fact, empowering these founders who to backtrack to something you mentioned earlier about these generalists with side quests versus specialists with main quests. Within Shopify, people's main quest is absolutely Shopify and the aligning with the business's mission. But to me, I mean, at least I speak for myself as a Shopify store owner, my goal when starting my Shopify journey is turning my side quest to a main quest. and it's this in-between meetings, try to figure out the side hustle.

37:17So it ultimately becomes the main hustle, kind of like Rich. He's going to be our case study for this conversation. And I'm sure that the same way that there's lots of value alignment between the people who can dedicate their lives to aligning with someone else's main quest at Shopify and within the business, there must be values that you've noticed aligning between founders who are so passionate about starting a Shopify business and growing from side quest to main quest with Shopify. I'd love to know more about those values that you may have studied in founders. If you look at the most successful stores on Shopify, there's millions of stores.

37:59You'll get the ones that have gone from mom's kitchen table to a billion dollars. There's a couple of things they share. One of the things they share, This is not always the case, but most of them share a couple things. One is the problem they are solving, they are completely obsessed with. I mentioned FIGS. I've gotten a chance to know the co-founders of FIGS, Trina and Heather. FIGS is now a publicly traded company. Amazing. Built entirely on Shopify. Amazing story. If you walk in any hospital anywhere in the world, there's a good chance that a big chunk of the people there that care about, like, you know, you're wearing hospital scrubs.

38:35So there's not that much like you can't wear a cashmere, you know, you're not wearing summer walks. But the people that do sort of want to wear something a little bit more elevated, they want to be a little more comfortable, they're wearing figs. Why did they start the company? Because a friend of theirs, a doctor in California who they had lunch with one day, came in their doctor scrubs and it just looked ridiculous. They're all the same color green. It doesn't look very nice. The color kind of like hospital scrubs are kind of this thing. It's almost like your armor. You go into battle to help and save patients and make people healthy.

39:09Like, why are you wearing the stuff that just doesn't look very good? Ben Francis, a gymshark, he wanted something that wasn't yoga and wasn't bodybuilding. There was kind of nothing in the middle. You look at what Rich was, you know, like Fashion Nova. The fact that, you know, if you wanted to be able to buy a lot of clothing, you would spend a lot of money. And if you wanted to buy cheaper clothing, it just wasn't very fashionable. And frankly, one of the great parts of Fashion Nova is if you actually go to the site right now when you're watching, go to the site tomorrow. It'll look completely different.

39:44Whole different website every day. Whole different. Right? Because Rich has built something that is so tapped into always on zeitgeist fashion. Yeah. That like if you see someone wearing something in Coachella yesterday, today something similar is available on Fashion Nova. these are people that are so obsessed with their thing that they would they ran through walls to get there and more importantly they never downshifted they never said all right now i'm gonna cruise i i think that's that that is amazing i had a chance to meet with um ben who's the founder of hodinke you know dinky yes amazing watch company actually recently got acquired by watch of switzerland um amazing story and hodinke it's done really well they they use shopify as well to sell a lot of watches and a lot of products um ben's company was acquired he doesn't know his company but watch watch the switzerland now owns it he works harder now i think they did before and i i sort of asked him and i was like you know you seem like like you're constantly like you know it was just um uh watches and wonders i think it's called in gineva and i just watched the content and the blogs he's putting out and like it's because he's obsessed with this thing it isn't a widget and again going back to the old way of doing business it used to be about selling widgets it almost didn't matter what you were selling you can be selling cameras or microphones or coffee you didn't really care about you were just selling a product because that was your job, quote unquote.

41:25The job thing has become so much more personal now. And the people that have been successful are obsessed. The second thing is, there is this incredible appetite for discomfort that they all have. I give this onboarding talk to people that join Shopify. And I talk about one of the best parts of one of the things that I think is sort of the hack to being doing well at Shopify is to be really, really comfortable with being uncomfortable that I think all the magic happens on this where you can sit in discomfort where you know you're not feeling that you got swagger and you're feeling super confident that you're kind of feeling a bit uncomfortable that you're like the people around you like they're all kind of smarter than me that's the magic spot and the people that have built these huge companies on Shopify they have a very high pain tolerance for being uncomfortable call it cringe call it discomfort whatever you want to call it they're okay with that because ultimately their ambition, their vision is so much bigger than them not feeling like they look cool right now.

42:21I agree with them. And, I mean, you're the master at it. How much, I mean, it's true. I mean, think of how many times, like, someone watches one of your videos, especially in the early days, and was like, what is this? And I'm sure you, I don't know if you keep it, but, like, you know, my, on Sundays, I was telling you earlier, I've created this archive of the greatest stories of the greatest Jewish entrepreneurs. And we've done, like, 25 of these. And I always go back to the first video on YouTube. It's called Big Shot. And I go to the first video and I love going to the comments. And it's like, these interviewers suck.

42:53Like they keep interrupting the guest. And the video quality is terrible. And like, this is why no one's watching it. And I see that stuff. And that is, that's the ambition juice for me. Absolutely. That's what drives me. And I think if you can teach yourself, and no one's born with that. No one is born with grit. Grit is learned. The ability to, you know, the expression like when the tidal waves are coming, some people grab their towels, other people grab surfboards. No one is born being in a surfboard camp. You get into that camp by grabbing your surfboard in these moments and getting and just the more you do it, the less cringy it feels, the less uncomfortable you feel.

43:38And that's been a huge secret. I would say maybe the other one that is sort of universal across these really successful entrepreneurs is that there's this appetite for experimentation, that they're always trying to try something different. Maybe they had a different skew. Maybe they go be, you know, like Hodinkee, for example, which has been this very famous watch blog for a long time. Eventually, they started to embed commerce in the blog. So you're reading about, you know, a new Patek Philippe watch just came out and actually you can click the link to try to buy the watch or to buy, you know, a strap for the watch.

44:15No one was doing that. Now in hindsight, it's like, of course, every blog has to also have a commerce components, like idea of commerce and content sort of, you know, colliding together. But Ben started doing that at a time where no one else did. And he knew that if it weren't great, if it didn't, it wouldn't be a big deal. Rich is constantly putting stuff out there. I don't know any exact anecdotes, but I suspect if he was sitting here and he said, tell us a bunch of things that did not work, you'd be like, are you kidding? Like, these 10 ,000 SKUs never sold. Yeah, for sure. But it didn't matter because this idea of, you know, failure being the successful discovery of something that did not work is something that I think great entrepreneurs all have.

44:55I love it. And I really like the fact that, you know, Nike did this amazing thing to the world where they convinced the world that if you have a body, you're an athlete. Which means that, like, my, you know, seven-year-old mom somehow thinks that, like, Nikes are for her, right? Because Nike convinced her that they are for her. That because she has a body, she's therefore an athlete, and therefore she should wear Nikes. And I think what I want the legacy of ShopVeta to be is to convince the world that if you have ambition, you are an entrepreneur. That it's not just Rich or Trina or any of your, you know, if you have some ambition, you should go and do something with that.

45:34And we all know people that have these hobbies. They make the most delicious soup or they make these beautiful jewelry for their nieces and nephews or they go into their workshops and make these beautiful wooden toys. is imagine if everyone who wanted to can take those hobbies and turn them into life's work stuff. Quit the job that they have working at the place they hate and rather take the thing they love and share it with the world. Not only will we as consumers have more interesting things to buy, but also their life will change. I love what you said about the, when the tide comes and the wave comes, people either grab their surfboards and go towards the wave or grab their towels and run.

46:17I find that had I been born 10 years prior for e-commerce in particular and this corner of entrepreneurship for me, I would have grabbed the towel and ran. But I feel like now due to timing, I can grab the surfboard and run towards the wave because the privilege of a business like Shopify allows me to focus on passion. And the reason why I call it a privilege is because without Shopify and other tools that are massively useful to me, the process of being a founder would be a lot clankier and uglier. And it wouldn't be fun and liberating and it wouldn't allow for passion. Well, let me tell you actually what you've done.

47:02If you study history of commerce and retail, here's how it always worked. A company would go out and they would make a product. They'd make this glass. and they make those beautiful glass, I don't know what this is, beautiful glass, and they'd say, I'm going to make this glass. It's going to be perfect. People are going to love it. And then they manufacture it. They make it. They brand it. And then eventually they say, okay, now we need people to buy it. So who's going to buy this glass? Okay, I'm going to go find customers for it. And they go into marketing and sales and they take ads out. And eventually people buy it.

47:32So product first, and then you go ahead and you sell it. You find an audience for it. You didn't do that. You did the exact opposite. You built an audience first, and then you figured out, what would my audience value? What type of product? What type of brand? What type of quality? What type of price point? You have effectively flipped the script on thousands of years of commerce. Think about that. And you're not the only one to do it. Jimmy did this too. Mr. Beast did this too. Jimmy created this massive audience with Mr. Beast, and then eventually he said, you know what? I'm going to do chocolate.

48:09I'm going to become the largest chocolate company in America with Feastables. Emma Chamberlain did it. She had this great blog and great podcast. And she's like, you know what? I talk a lot about coffee. Why don't I create my own coffee? And so I think a lot of people look at famous people, people with big audiences like you and some of those others that I mentioned, and say, yeah, they're going to create like promotional product. what is being created are not promotional product if you look at you know um we're pretty close with the with the drake team with ovo and that team and uh and and and we've sort of watched what ovo has built ovo was not a promotional product for drake it's a standalone incredible clothing company i mean they're doing collabs with canada goose and all these amazing companies and roots and all these all these places this idea that first you can build an audience and the audience truly trust you, high trust battery, and they believe in you and they want to connect with you, then you can figure out, I'm going to create, manufacture, build something that is a value to them.

49:12That is completely a new way to do business. Our grandparents, our great grandparents could never, ever have imagined that. In fact, what used to happen was if you liked, if someone had an audience let's say um you're a rock band most of these merch stands at at like concerts were promotional products it was a shitty t-shirt with a shitty screen print now you go to some of these shows and you go to the merch stand i went to see fish at the sphere recently go to the merch stand it is mind-blowing it's like this incredible store of product there are sneakers and there are hats and they're all amazing.

49:49It is not promotional product. It is actual product based on the exact needs and the particular preferences of the audience. And that's what you think you've done with Stock Guy. I appreciate that. I love that. I mean, I never thought of it so clearly, but it's true. I do think it's definitely what's happened. I mean, because you probably, even when you were doing those videos, at some point, someone said, oh, you're an entrepreneur. And maybe because of your background and Bapson, you're like, yeah, I'm an entrepreneur. But But think of how many people right now are creating content or creating something, but they don't believe they're entitled.

50:23They don't have the permission to say I'm an entrepreneur. Guess what they are. If you were actually creating something for someone else of value, you are an entrepreneur. And the best thing about it is if you can figure out a way to create enough value that in exchange they give you money, also known as profit or revenue, you build a business. And because of the time we live in right now, that business can become really big really quick. I don't know how old-fashioned Nova is. 10 years old? That's unbelievable. When in the history of the world have you seen that type of business growth trajectory happen so quickly?

50:54You'd have to go and raise a ton. I don't think Rich has ever raised any money. I don't think so. Right? I think he owns the whole company. Never raised any money. I mean, that's where he can have the one. That's where he can have these houses. But he didn't even raise money. He allowed the business to fund the growth of the business. This is like. So, again, it's difficult for me to not believe that this is the golden age of entrepreneurship. when I have this purview, when I have this perspective of watching these people like you build empires. And you may be early in your empire journey. You're going to get there.

51:25But I'm like, I'm ride or die for these people. I appreciate that. And I love that. I mean, we've spoken a lot about people who were strong audience first, like Mr. Beast, Emma Chamberlain, Logan Paul, many more. And to a much smaller degree, myself. and we also spoke about people like Rich who are store first. But I'm very curious to see your point of view, to hear your point of view on the entrepreneurs that are neither first and that have this blank slate but this incredible desire to start something and to not be employed but actually just do their own thing. Where does their journey start beyond the simple desire for freedom of entrepreneurship?

52:12Yeah. And the freedom of entrepreneurship comes in many flavors. For some people, it's to become a billionaire. That's it. For some people, it's literally just to afford, you know, ballet lessons for their child. Everyone has different definitions of success. the way it should the way i think it should start this is my my opinion is that it should start with something that you already want to exist in the world it's something you care about i don't think you need to go to some sort of like seminar about like a business idea seminar i don't just i don't think like you can use like there's the tools are amazing right i mean like the the especially some of the visual tools you can use like with ai for i mean right now the ability to create ads on something like ChatGBT or Perplexity or Claude is unbelievable, right?

52:58Like you used to need, um, uh, one of the people that I interviewed for Big Shot was Mickey Drexler. Mickey Drexler was on the board of Apple for many years. He was, you know, very close friend of Steve Jobs, but he also, he built the gap. He created Old Navy. Um, he pretty much recreated J.Crew and he used to talk about the size of the company inside of the gap. They had hundreds of people doing all these different things doing merch, you know, during merchandising and doing marketing and product photography, the technology that you have right now for free, all of you watching in your pocket is more impressive and more valuable than the team that Mickey had 20 years ago at the gap in San Francisco.

53:37That's amazing. But in terms of like, what do you start? What do you care about? What's the thing that gives you great joy? What do you already feel passionate about? In the pandemic, I wanted to, as I mentioned, I started my first Shopify store in 2006. I had not started a new store in a long time. And during the pandemic, one of my best friends is obsessed with tea. His name is David Siegel. And David Siegel built a company called David's Tea, which he took the same year I took Shopify public on New York Stock Exchange. He took David's Tea public on NASDAQ. Amazing business. And he left the business.

54:13But during the pandemic, I'm a power extrovert. and I was alone in the pandemic like most of us were and I was not in a good place. My anxiety levels were super, super high and I told David that I wasn't necessarily, I didn't feel I had energy in the afternoon and I didn't want to have more coffee because of the anxiety and so David began to curate these boxes of super high-end tea to me. Sencha, mostly sencha, Japanese sencha and it was loose leaf tea, it wasn't the tea bags and you bring it over and be like try this, he's like steep it for two minutes at this temperature use this accessory and he brought literally would bring like these he's like your little sieves yeah exactly and there'd be a duct tape on he'd be like i made you this thing use it like this and i started drinking really high quality green tea and i loved it unlike coffee which would make me jittery in the afternoon particularly high incentive tea had this sort of calm alertness to it it was beautiful and david and i i kind of wanted to start a brand new Shopify store to see what it was like to build from scratch.

55:16And Dave was kind of looking for something new. And we were kind of sitting around like this. And Dave was like, I'm not sure what I'm going to start. And I was like, yeah, I want to start a Shopify store. And I was like, dude, let's start a tea company. It's so obvious. Like we're here drinking tea. You're creating this amazing tea for me. I know you're doing because you're my friend, but like the accessories, you're sort of, you know, MacGyvering together and the tea you're curating, like, let's just do this. And we created firebellytea.com. Firebellytea.com now does many millions of dollars a year.

55:43We have a CO for it because we didn't have time to, you know, neither of us are able to run it anymore. We both have our main quests. That's this thing you should be doing. What is in front of you right now? What is the thing when you and your friends get together with on a Sunday afternoon and you talk about it? Is it sports? Is it fashion? Is it mechanics? Whatever that thing is, that's what you should add to your blank canvas. And instead of trying to invent something that is unique and creative and what you think the world wants, that do the thing that you want to put out to the world and if the world sees that you deeply care about it and it's thoughtful that's where you should start and just to say the thing entrepreneurship is not glamorous it isn't easy most businesses do fail but the cool part is because the cost of failure is so low you know gymshark was not ben francis's first business and fashion nova.com was not how Rich started.

56:38Rich started with a physical retail store in a third-tier mall in Los Angeles. It wasn't very nice, and it was only later on that he figured out online is going to be what he does. So that first idea doesn't have to be perfect, but it does give you a starting point. I love also that you spoke about the idea of entrepreneurship not being easy because at the same time, it's definitely not for everyone. And there's a lot of conversation online right now about creators over glamorizing the idea of entrepreneurship. Hustle porn kind of stuff. Hustle porn. Yeah. And not preparing people for what the reality looks like.

57:14And in many ways, you are a tremendous entrepreneur, but you're also a tremendous intrapreneur because you joined Toby and Shopify when, I mean, there wasn't much there at the time, but you built tremendous value within. Yep. And it sounds like lots of those values and skills still apply to people looking to create value within an existing entity. I think lots of people out there definitely like their jobs and like their systems, but would like to create value in a similar way that Rich even created value within his successful brick and mortar store by going digital. Are there any stories or recommendations you may have for those people who may not have the risk profile or desire to go off and sail and do their own thing, but actually find themselves somewhere in between.

58:05Yeah. I think the key, so on the, in the entrepreneur thing, first of all, even saying it like that, it almost makes it like you can either be an entrepreneur or you can be an entrepreneur. Like it almost sounds like a second class. It is not. The reason that I have been able to achieve everything I wanted to personally at Shopify. I don't necessarily think you need to be like the founder of this thing. I'm not technically the founder of Shopify, Although it feels like my baby, it always has. Toby's always made it feel like it was also mine. And actually good founders do that. The best founders I know, when they create this collective of people that are going to help them lead the company, it becomes like it's their own.

58:51It becomes like it's their baby. and I think the ideal situation, if you're in a place now where the vision and the mission of the thing, of the company, is bigger than what you could do on your own, maybe that's a good place for you to actually build. There's a lot of good examples of this. I mean, you know, I don't think Satya Nadella, Satya Nadella is not the founder of Microsoft, but he treats it like he's the founder. That's how I feel about Shopify. So one is, if you believe that thing, like your personal mission, you see it in a company out there this may be like you're really into sneakers and you could go search your own sneaker company you also can go join kiff or nike or on running number one you may learn a ton from working with really smart people but also you also can create your own ambition your projects inside of those larger companies and i don't think i could have like i if i wouldn't have gone to shopify i would have sold t-shirts and i would have built i think a pretty successful t-shirt company.

59:53I was always really ambitious and I've always been really hardworking. I would have figured that out. But I never would have had the impact on the world that I can have by doing it under the umbrella, under the auspices of Shopify. The key to it, I think, is that you have to just add a disproportionate amount of value. You have to be, you know, there's my favorite rabbi who shares the last name with my wife, although they're not relate to Rabbi Tobe. He has this thing about thermostats and thermometers. And he talks about that some people are thermometers. They walk into a room, they take the temperature, and they acclimatize.

1:00:31There are other people that walk into a room and they're thermostats. They go in, the room's temperature is off, they turn up that temperature. The thermometer people can do well at a company, but not nearly as well as the thermostat people. If you can go into a company turn up the thermometer in every room every project you work on you will be number one you will be way too good to ignore so you'll have an amazing career there hopefully you're working for someone in my case for toby who sees the value of it that sees that actually like there's no way that this company will get to where it is without people like you and i think i'll have a lot more fun um so you know the famous line is when you're joining what is it like you know when you're Provided on the rocket ship, you don't ask which seats.

1:01:16You just get on the rocket ship. If you're going to work for a big company and you know you want to be there, but ultimately, you know, you got an entry-level job at that company, who cares? If that's the company you want to go to, go take that entry-level job. Figure out exactly how to be, you know, the thermostat in everything you work for and always look for different opportunities. And if you give yourself a long enough time horizon, you can find your life's work working at someone else's venture. And eventually it becomes your venture too. So I don't think it always has to be your original idea.

1:01:52And in fact, I think in a lot of cases, people have a bias for, well, that's their thing and this is my thing. And I think that's just ego talking. I think you can go and find something bigger. Now, frankly, if you use your example, you were at Apple when you started ShotGuy. I think Apple probably gave you a little bit of a confidence foundation. Absolutely. That like, if this thing was going to go nowhere, man, I work at Apple. It's a pretty good kid, right? It's a good sort of springboard for other things as well. So I don't, you know, I still think you can absolutely grab your surfboard working for someone else's company.

1:02:30What about the people running those companies and the CEOs who feel like they wish They could have this sort of nimble startup culture where they're encouraging their team to be thermostats, but they just don't have that office culture and they're blaming their staff or blaming timing versus turning things around. Are there any tips for the CEOs to encourage this nimble entrepreneur mindset within their existing organizations? We hire, if you look at, you know, there's 7 ,000 or 8 ,000 people who work at Shopify. Most people, you know, when I give my keynote at Summit every year, we bring the company together.

1:03:07One of the things I often ask is like, how many of you are entrepreneurs in the room or have been entrepreneurs? Almost every hand goes up. Shopify is a company building software for entrepreneurs, but it's being built by entrepreneurs themselves. The amount of people at Shopify who also self-identify as entrepreneurs is unbelievable. It is the highest concentration of an entrepreneurial collective of any company I've ever experienced. That is by intention. We like people that are entrepreneurial. I don't really care if you've got a Harvard MBA. I actually much, I care much more if you like ran an ice cream shop in your community.

1:03:37And then I ask you, why did you start the ice cream shop? And you're like, well, there was no ice cream shop. I wanted one, so I built it myself. That type of audacity, I think, breeds incredible entrepreneurial instincts. And I think if you create a collective of people like that, it's amazing. I do believe that most people make the mistake of thinking that culture is, you know, the posters on the wall. You know, I love to, like, I love to make fun of, my team actually has one of my, just bought one for me from my office, which is the picture of the eagle, and it says, like, ambition or leadership.

1:04:07You've seen that? That is not your culture. Your culture is what happens when nobody is watching. What do people do? And I think one of the reasons that it's important to have a strong mission is not because, like, you want to have something on your website. It's because when there are two things, you can select two options to a particular problem. you can always use the mission as your compass of like, for us, it's like, we want to create more entrepreneurs. So given two examples, how do we create more entrepreneurs? We're always going to pick the answer that creates more entrepreneurs. I think that as a leader of a company, if you think that the reason your culture is a certain way and the reason shit's not getting done is because you've hired the wrong people, maybe that's the case.

1:04:49More times than not, it's because you haven't actually set a proper culture where people want to get shit done or people want to do their life's work here. Maybe you're making everyone feel like it's your thing and not their thing. And when I watch a lot of the people we've been talking about here, you know, I actually, the person that runs e-commerce for Ronnie, this guy, Andy, for Kif, amazing guy. Andy's head of e-commerce for Kif. And if you have a great experience online, it's because of Andy. Andy could work at any company he wants. And he chose to work for Ronnie because his life's mission, his surfboard is e-commerce and modern retail innovation.

1:05:28And he saw what Ronnie was doing with fashion and culture. He's like, if I apply my hunger, my ambition for e-commerce with someone like Ronnie who cares that much about sneakers, we can build something bigger together. And ultimately, you get the one plus one equals 10. And I think that is really possible. And that's the reason why, you know, when you're interviewing for a job, yeah, the company's interviewing you, but you better be interviewing them as well. Is this something you really care about? Because if you just want to make a ton of money, go be a dentist. And some people want to be dentists.

1:06:00I don't. I think if you want to find your life's work, you can do it on your own. And I want more people to do that. Or you can find someone who's already doing it. It's actually, what's interesting is that ironically, when people have co-founders, they tend to have co-founders with people that they would be friends with in high school.

1:06:19and usually you're friends in high school with people with similar interests, similar skill sets. Toby and I would not have been friends in high school. He was in a computer lab, and I was class president, and if we were to start a company together in high school, we would not have done it together. We wouldn't have been friends in high school. So actually, if you were out there, and you're listening, and you actually want to start a company with someone, or you want to go work for someone, this idea back to the Avengers thing is find someone who isn't like you, someone who actually, who you probably wouldn't have been friends with in high school because likely that's going to create the best partnership.

1:06:51And these are the sort of things I think you can read in a business book. You don't look like, you know, most people can teach this type of stuff. But when I zoom out and I look at millions of stores doing hundreds of billions of dollars on Shopify, these are some of the through lines that I've seen that have led to some of the biggest companies being built. Well, there's one thing we always do on the Start Guy podcast, and that's a quick round of à la poubelle versus fantastique. Perfect. As you know, à la poubelle is things we'd like to change. Je parle français. Voilà. And fantastique is things we love and celebrate and we'd love to see more.

1:07:22Do I have to do the accent? À la poubelle, fantastique? You can if you'd like. Parfait. Mon français n 'est pas trop bon. No, we can do it in English. As you wish. But just one thing you'd love to change and throw à la poubelle and one thing you celebrate and you consider to be fantastique. Okay, I got one. We talked a lot about like school. We talked about Babson. We talked about McGill and stuff. this idea of going to school to find your career rather than go to school to actually find to to find skills and find your co-founder and find the thing you're passionate about i think going to school going to university uh to get a piece of paper to go you know go work at some company a la poobel a la poobel that isn't just because your parents and grandparents told you to do so and again i'm the child of of immigrants like a lot of immigrant parents want their kids i went It's a law school, right?

1:08:12I mean, like, that's what they want. I'll have a belt. Fantastique. There has been a resurgence. We're in the US right now. In the last four years post-COVID of new business registrations. If you look at the actual business registry of the US, there's been a resurgence of more people starting businesses. Fantastique. This idea that more people can participate in entrepreneurship and find cool stuff and do cool stuff. Fantastique. I love that. I love that. Those are perfect. Yep. Well, thank you so much for being here, Harley. Fantastique. As expected, fantastique. This was an incredible conversation.

1:08:49Always love to hear your stories and your incredible insights. And I'm very excited to see where you take Shopify next. Appreciate you. Thank you. Thank you for being here. Thank you for listening to this episode of the Stade Guy podcast. If you're keen to learn more, please follow along by engaging with our social channels On Instagram, TikTok, Spotify, YouTube and Apple Podcasts And we look forward to seeing you next week Merci beaucoup, à la prochaine And a big hug from the Start Guy