Aspire with Emma Grede - How to Win in the Golden Age of Entrepreneurship

Episode Date: December 2, 2025

What separates the entrepreneurs who start… from the ones who win? Harley Finkelstein (President of Shopify and the man who has worked with millions of founders) sits down with Emma Grede to reveal the hard-earned truths behind building a business that lasts. From the real reason most people never act on their ideas, to why the “golden age of entrepreneurship” is happening right now, Harley breaks down the mindset, tools, and strategy that turn dreamers into doers. In this conversation, Harley shares: -Why execution matters more than ideas -How to start a business with no money, no network, and no experience -The habits shared by the most successful founders on Shopify -Why the cost of failure has never been lower -What it takes to scale a business in today’s creator economy -The mindset shift every entrepreneur must make to succeed Emma and Harley go deep on the courage, grit, and resourcefulness needed to build something from nothing — and why someone watching this right now could be the next billion-dollar founder. If you’re an aspiring entrepreneur, a builder, or someone sitting on an idea you’ve been too afraid to start… this episode is your blueprint. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

I am so excited to share my debut book with you or Start With Yourself, which is available now. You might have seen the headlines, you might have seen the social, but this book is exactly what I intended, a conversation that will make you think, and it's a blueprint for anyone who wants success without the toxic positivity. Start with yourself is about self-leadership, because wherever I go, women ask me how I got to where I am. But what you really want to know is how you can get there. So I'm doing what I do best, sharing and navigate keeping what's works for me in the hope that you can borrow from a philosophy that has served me so well. The truth is I'm not an expert. I've just lived it. I've made the mistakes.

I've had the failures and I've learned what actually works. It takes a lot. It takes the most. And this book is for anyone who's tired of feeling like a passenger in their own life. It's about taking responsibility for your thinking, managing your emotions and getting clear on your ideas and then knowing your next step. It's about picking yourself up after failure, being accountable, but also forgiving yourself, pushing for wins, and never, ever apologising for your ambition. It's also about challenging the rules that you've been told. There is no perfect time. Balance isn't the goal. Alignment is and there's nothing wrong with you wanting more. I'm precisely sure that the reason I've been so successful is so I can

share it with you. Start with yourself. My debut book is available now. Visit emigre.com to purchase the book, also available on Amazon, your favourite audio platforms and all good bookshops. No one has seen more founders succeed or fail than Harley Finkelstein. And in this episode, he shares the hard-earned truths that separate the dreamers from the winners. Harley is the president of Shopify, the e-commerce platform valued over $200 billion, creating groundbreaking tools for millions of founders to build their dreams from the ground up. He was one of the platform's first entrepreneurs selling t-shirts before running the company. And that experiment turned into a career spent helping others do the same.

Starting takes guts. Winning takes strategy. Today on Aspire, Harley shows you how to master both. Holly, thank you so much for being here today. It's a real honor, Emma. Thank you for having me. I want you to take me back to the beginning to understand a little bit about where you come from, your start in life and how you find yourself here. Well, I am this child of a Hungarian immigrant who came to Canada from Hungary in 1956, had no money. And I was surrounded by entrepreneurs growing up, not because my father or my grandparents wanted to be entrepreneurs, because most immigrants have no choice but to use entrepreneurship as the tool to put food in their table. You know, I've always self-identify as an entrepreneur. I think entrepreneurship is the greatest way for humans to find their own

version of success. And I found myself years later in law school having to pay for school. I started a t-shirt business and needed to sell it online and met this German immigrant who was selling snowboards on the internet and decided that the software that he had written to sell these snowboards was more valuable than the snowboard business itself. And I became one of the first people to use what would become Shopify. I sold T-shirts all throughout school. And after I finished law school, I called that German entrepreneur named Toby and asked him if I can join him. And I was about 16 years ago. And I became one of the first people to work at Shopify. it was remarkable because I was 21 years old.

I had very little money. I had no experience. And this piece of software, it was like magical fairy dust. Yeah. That when you combined ambition with the software called Shopify and you hit the launch button,

you immediately have a global business. And I think what was so remarkable was there was no like sealing on my success. Yeah. No one was saying, well, you can only get this big or you can only sell in these geographies. It allowed me to build this T-shirt company that ended up supporting myself, paying my tuition.

I was paying my mother's rent, helping my sisters at the time. My dad wasn't in our lives at this point. And I just needed to support my mom and sisters and pay for myself. And I thought this thing called Shopify was the greatest tool for entrepreneurship ever. And you were right. And that's why I talk about it so, so much, because you have to kind of, it's so hard now in 2025 to go back to that time and think where we were. It wasn't just expensive and difficult. For a certain subset of people, it was an impossibility.

That's right. Like selling your goods online, it was like, that's just not for me. There's no way I can figure this out. So go back. Look at the history of retail. Go back to 1876. 1876, a guy named John Wanamaker created Wanamaker's department store in Philadelphia. It was one of the first department stores in America.

If you wanted to sell your products into Wanamakers or any store thereafter, you had to convince a retail buyer to put your stuff on the shelf. That was a gatekeeper. Okay, let's see you decided I'm not going to go through the retail side. I'm going to build my own store. There's another gatekeeper, which is you need capital. You need money. I need to rent.

I need leasehold improvements. I need inventory. Historically, entrepreneurship always had these barriers to entry, either money or people. And one of the things that I think is so incredible about modern entrepreneurship is there's no more gatekeepers. And because there's no more gatekeepers, everyone can do it. Yeah. But one thing that I think people don't realize, and I think what's so amazing about aspire is, I think you are aspiring people to actually think about this is, for the first

time in the history of entrepreneurship, the cost of failure is almost zero. So you see these great companies like skims or good American or Jim Shark or Allo or Viori or any of these companies that I've watched grow from scratch on Shopify. If those businesses would have failed, entrepreneurs like you would have tried some something else. Totally. Right? Go back 50 years.

If you would have tried something and it would have failed, you would have lost your house, you'd owe money. There was this real cost of failure, so you had to be right. Yeah. Whereas now you can try a bunch of things, figure out what works and the one that does work you can double down on. Well, and not only that, but you're so much in control of it, right? Because even if I go back to starting my own first businesses, we were hedging, right?

We were saying, we're going to be predominantly D2C, but we're going to back ourselves up with this wholesale component. You have no control. That's right. You have no visibility. You don't understand who your end customer is. You're kind of selling your goods and you're crossing your fingers and hoping for the best. And for me and the reason I do talk about Shopify all the time is because the control,

the visibility, the power it gives you from the outset for you to see this thing in real time. As a founder, it really is like magic. And so I understand that feeling that you got because what it did for me was give me this like understanding, like who is my customer? Where is she buying? what does she look at, what is important to her. And so this unlock, and for me, again, I talk a lot about, you know, who gets to be an entrepreneur, right? And now we talk about price of entry.

We talk about who gets to do it. All of that just went away in like a second. And the second you get that first sale from someone you don't know, forget your mom or your sister. Exactly. That chiching sound, your life changes. All of a sudden, your identity changes. You get a little bit addicted. Definitely.

I mean, I'm walking through a random airport and, like, Colorado last week. And all of a sudden I hear a chiching and I look around. No, those chichings are a joke. And that woman looks to me. I look at her and I'm like, congratulations. She's like, that that that sound never gets old. But really what we're talking about here is the fact that now entrepreneurship is accessible. It's accessible to people that otherwise did not think it was. And if you think about, you know, take a company like Nike. What Nike did was they convinced everyone that had a body that they could be an athlete. So it means that my mom, a seven-year-old Jewish lady believes that she's an athlete whenever she

Lace up her night. She is. She is. Of course she is. So what we're trying to do is convince everyone that has ambition that they can be an entrepreneur. And you think about every, all these ideas in the shower in the morning, most people don't do anything with those ideas in the shower because they don't have a next step. What we're trying to do is make it so that if you have that idea, you should just try it. And the truth is, if you do try it, you could be the next skims or the next billion dollar company. And the crazy part is I get to watch that happen every single day. Every single day. I mean, I honestly, think what it must be to be like you, not only just like having this incredible one in a billion,

one in 200 billion, you know, opportunity to build a business like this, but you sit on so much information. And the reason that I wanted to have you here today isn't just, you know, to just talk about platform and how amazing it is, but really to give people an understanding of what it enables you to do. And so I was thinking about trying to dissect and given that you have such an unbelievable overview. Successful, unsuccessful. I want you to try to pinpoint for us where the commonalities are. Are there some things that you've seen over the years that you're like, this is what makes someone successful? This is what we see over and over and over again. And these are the patterns. Somebody first talk about success because one of the things that I think

entrepreneurs are very bad at is that we talk, especially successful entrepreneurs, we tend to talk about our highlight reel, not our BluPo wheel. And so people see people like you or in some cases, people like me and they say, well, they got lucky. And there's no doubt there is luck in all this, right? There's a hell of a lot of luck. However, what you don't know is that a lot of the biggest companies and brands on the planet you see certainly on Shopify, it wasn't their first business. Their first business probably failed. I love that you said.

Their second business probably failed. But the third business became Jim Shark. Now, Ben Francis is the youngest billionaire in UK history. I mean, I love Ben so much. I love him. I've watched Ben since 2012. use grit and sheer hard work and this unrelenting desire to be successful, build a billion-dollar company.

So the first thing is most successful entrepreneurs that you see out there unequivocally have a past litter with failure, but doesn't really matter to that, right? Because they have this grit, which allows them to persevere through it. And isn't that the important thing that, like, knowing you're going to have failures and then being able to have the resilience to come back after them? Because that's the first thing that will stop you.

Like if you start to think that the thing that happened is you, that there's something wrong with you and that you can't get over that first failure. Like you will never be an entrepreneur. Well, part of it also is that there's this connotation, for example, that I remember when I told my mom and dad, who were very proud that I finished law school that I was not going to be a lawyer, that I was going to join this little company called Shopify. Their first reaction was like, oh, what happened?

Did it not go well? I'm like, no, I just, this is my life's work. I believe this is my life's mission is to help more people become entrepreneurs. So when you have a failure, the people around you say, oh, well, you tried that. Maybe now you should go. Do something else. Go be an accountant or go be a dentist or something like. Not there's anything wrong with that, but that's not entrepreneurship.

So the first thing is, I think surrounding yourself with people that are kind of these force multipliers of your ambition that are always saying, hey, you tried that, keep going. The next thing may do it. The second thing is that I think is very important is this idea of Tam, total addressable market. I think a lot of entrepreneurs. when they're just getting started, one of the things they make the mistake of doing is they look at the market for their product and they say, well, here's the pie. The pie is this big. I'm going to take a

larger slice of the pie, right? The shapeware market, for example. You could have looked in and said, hey, it's only this big. There's a couple companies in it already. We're going to take a piece of it. Instead, what I think you did was you said, no, we're going to grow the pie itself. We're going to convince people that otherwise may not wear shapewear to wear shapewear. Or we're going to convince people who otherwise may not self-identify entrepreneurs to try their hand in entrepreneurship. The brands, the businesses, the entrepreneurs behind the most successful companies on Shopify believe that their TAM is expanding. It's sort of this like growth mindset versus fixed mindset, right? Or zero sum versus positive sum. The best entrepreneurs have this positive sum understanding

and they believe that they can actually grow the market itself. That's so key. That's first thing. The second thing is, and this is very 2025, there was this, I'm on the board of something called NRF, National Retail Federation. And on this board, it's like, it's the CEOs of every major retailer, right? From like, you know, the big box stores to all these great companies. And when you hear these traditional CEOs talk, they often talk about channel conflict. I sell online or I sell offline or I'm wholesale or I do live shopping. And there's sort of this like buckets of them as well.

And sometimes talk about Omni Channel, why selling a couple different channels. I actually think in 2025, the most successful brands, merchants, entrepreneurs, they don't talk like that. They sell on every surface area where their consumer is spending time. Facts. And if it's online, that's where they sell. If it's on social media. And so part of what we're trying to do at Shopify is make it so that wherever you want to sell, you can. A great example is we, this is so esoteric or nuance, but we got a call from Roblox a couple of months.

ago. And Roblox said they want to build commerce retail into the Roblox Metaverse. We said, great, we'll build a channel for it so that any merchants on Shopify who want to sell in Roblox can. And a bunch of merchants tried it. A couple of them, like Fenty Beauty, really succeeded. They did a great job. It's because Fenty understood that their particular customer actually spends time in Roblox. But another cosmetic company tried that. It didn't work as well. Totally. So this idea that we are online merchants or we're offline merchants, I think is completely dated. And I think, you know, initially there was only one channel was brick and mortar. Then there were two channels online and offline. I think in 2025, every single place where consumers are spending their time is a channel.

I really, honestly, I love how you've just broken that down because it's so counter to how most people think about how you can be successful as an entrepreneur. Yours were who you spend your time with, who you surround yourself with, how you think about. your TAM, your total addressable market. I'm really thinking about expanding the TAM as opposed to what size of the pie you're going to take. And then lastly, being wherever your customers are at. And part of it also is that because, again,

even this idea of being, you know, across every channel, it used to be very costly to add a new channel. It's not anymore. It's not anymore. It's not anymore. And what I'm seeing is these entrepreneurs that are really doing great, they have this incredible appetite for testing things. And if they try the YouTube channel or the Instagram channel,

or the Roblox channel. We have a Spotify channel, kind of a weird thing. Shopify channel for Spotify. I do every morning. I go on the rock. When I'm trying to put the music in, I go on to Shopify.

You're like hearing it doesn't make sense. Okay. So for most people, most of the time, the Spotify channel doesn't make any sense. But if you're an artist and you have a massive artist following and you also have a great clothing brand,

that's an amazing place for you to sell. So that wouldn't work for me because frankly, I'm not an artist, but it works really well for those artists who also have clothing brands. And that's, I think, the way to think about it, that utilize all the channels that make sense for your particular demographic.

But what does it all mean? It means you have to know who your customers are. And that sort of empathy, I think, is something that you have nailed in every business you've done. Your understanding at a very scientific level of who is buying from you has allowed you to build experiences

that are tailored for that particular consumer. And that's kind of the secret. That's how you win. That's kind of secret. And you know, I feel like, for so many people that are listening to this, they'll be like, well, how do I figure out who my customer is? Who do I think about from the beginning when I don't even have any customers? And I always think about it, like, I'm my own best customer. Right in the beginning, I think,

if I want it, if I'm solving a need for myself, if I feel like my friends are going to want this thing, that's the starting point. It's always, it's always about me. It's always about my friends. It's always about a group that I think, like, this is a needed thing. And then, you know, you kind of branch out from there and there and there. And so it's so interesting, how you think about that. What are the things that just never fail? Like when you think about starting a business, what have you seen that just always works? This is a really good question. Story, narrative, mission. Like, I don't know how you want to call it, but why, we mentioned Ben, we mentioned Jim Shark. So why does that make sense? Because Ben had this story. 2012, he's in college

in the UK. And he realizes that if you were wanted to buy workout clothes, there's sort of two categories. There's like the like bodybuilder category and there's like the like yoga category. But there's kind of nothing in the middle. So he's frustrated. So and he works out a lot. So he builds something for himself. And he starts to tell people what he's building and why he's building it. What ends up happening is other people say actually that's kind of me also.

I'm not a bodybuilder and I'm not really into yoga. I'm looking for something in the middle. That idea of having a really great origin story or founding story just like for us around snowboards really matters because what's? you do is you carry the consumer along on your journey. And you turn consumers into almost these like force multipliers for your story. The bigger you get, the more they're excited for you. It doesn't feel like this transactional relationship. Rather, it feels like they're a part of the mission. And that's one of the great parts about shoppways and all the merchants on Shopify also love

Shopify. They tell people about Shopify because they're like, look, this changed my life. It can change your life as well. Totally. Totally. So I think this thing that is like unequivocally universal is that you have to have a great story. But you are so right that people adopt your story. Like in the early days a good American, I would go to these open castings and people would say things back to me. And I was like, did I write that? Is that on my website or is that how you feel? That's right. You know, but when you've got something that resonates with people, they identify it and they speak it and they tell their friends and it's the most simple thing. But having that story and that point of view and that mission that people can grab onto from the beginning is so key. It's so amazing.

And that's sort of also like mission is really, really important because ultimately what selling is, like, we are not selling software. We are selling this idea of success or freedom. Yes. Access. Opportunity. Exactly. Whatever you want to do, you're able to do with us, right? That is very different than go back 20, 30 years where you took an entrepreneur and they were kind of just selling widgets. The days of selling widgets that are not meaningful that don't necessarily have a deep emotional connection is a long gone. Over. Right? Because how are you going to compete with skims if you're selling shapeware that kind of is soulless, right? That's also where founders have an unfair advantage over professional managers. Founders always have a story. It's their story. They get unequivocally

to tell the story about what they did and why they did it. And you create this connection. What else just doesn't fail? What do you mean? Something else that doesn't fail is authenticity. This idea, so you mentioned earlier, you know, when you're just getting started, you may not necessarily have infrastructure or a research team and all that. I met an entrepreneur. I won't say their name because I don't know if they want me to say this, but it's a merchant that is doing a couple hundred million dollars now. And I asked them how they got their first 100 customers. A question always asks, how to get your first 100 customers. This was maybe two years ago. They said they were going on Facebook mom groups and posting products and saying, what do you guys

think about this? And I was like, well, did you send them? They're like, no, we just posted photos on random mom groups in their community. They live in southern east coast of the United States. And they said, what do you think about this? And what she said to me was that it's remarkable how many people are willing to give you their opinion if you ask, hey, I'm thinking of making this. What do you think? And someone would be like, well, don't do it that way. I don't really like it like this. Don't use plastic. Use this instead. So there are these things you can do when you're just getting started that big companies can never do because it feels inauthentic. But you, as a newcomer entrepreneur, people are willing to give you their time and their energy just because they want to

kind of support you, right? It's this beautifully optimistic journey of starting a business. business and people do want to participate in that journey. I love that. Is there another one? Is there something else that like you're like this, this never, ever, ever fails? Okay, so there is something new that is happening. And I think no one has nailed this, frankly, more than you, Emma, which is that if you think about how products have traditionally been built, you start with a product and then you find an audience. One of the things that I think is shifted. This is very new, like literally in the last five years is first you start with an audience and then you build a product around the audience. Now, if you go back, I was born in the 80s, there were celebrities that built products.

Most of those products failed. Why? Because it felt like a promotional product. So I think there was this famous story of Brad Pitt selling toothpaste. He didn't really care about the toothpaste. Some toothpaste company went to Brad Pitt and said, hey, we'd like you to be a toothpaste entrepreneur. That is very, very different now. You know, I had a front row seat watching Kylie built a lip kit and Kylie Cosmetics, which is an incredible business.

there was something so authentic about that. Kylie began to do these makeup tutorial videos. She was using other people's makeup. And she would give commentary and give these sort of tips and tricks. And then eventually she started experimenting with making her own. But every step of the way, she left a little breadcrumb. She said, I'm going to try this. I'm going to make this.

What do you think about this? Then eventually when she announced and launched Kylie Cosmetics and lip kit, she had this audience around her saying like cheering for her. because she really was disrupting the traditional cosmetics industry. So one of the other things I think is, and you can think, well, I don't have an audience like Kylie or like Kim or any of those.

Everyone has an audience. You may have a thousand followers on Instagram. You may have 100 followers on LinkedIn. It doesn't really matter. But we all have some segment of a community that is looking at what we're doing. And one of the things that I think always works is leaving these breadcrumbs as you're building. So you may start with a very simple video. Like use your pickup.

your smartphone and say, hey, Harley here, I'm thinking about making a pair of, I don't know, sneakers. I've never made sneakers before, but most sneakers I wear are not comfortable for me. My feet are wide or whatever it might be. I'm going to try and try, I'm going to try to stitch my own together. A week later, hey, Harley back. I'm thinking I have a prototype. I'm going to try it on. What do you guys think? A week later, okay, so I found a little small artisan in my neighborhood who's going to make me a couple pairs. A week later, okay, well, I've made 12 pairs. I'm going to put them online and see if you guys like them. If you keep doing that with this consistency, by the six-month mark, not only are you going

to have a real business, you're going to have an entire fan base of people that want you to be successful because they've seen these little breadcrumbs that you've left. That was impossible 10 years ago. Yes. And this idea of starting with an audience, cultivating the audience, and then building a product around some of the audience truly desires, enjoys, likes. feels a part of, that's unbelievable. And in the same way that Shopify has made

entrepreneurship accessible, social media means we all have these little media companies in our pockets. And one of the things you and I have talked about before is I have a zero cringe factor. I'm not a cringe. Zero cringe, right? Like, I don't have that emotion, my body.

So yes, turning the camera around and filming a little video of yourself thinking of building a sneaker company, there is a little of cringe. You've got to get over that. And if you can get over the cringe factor of it, You can build a billion. And do you feel like you have to get over it?

Like if you're not that type of person, is there a way to build a business? Because it makes me feel like just hearing what you said, you must be very kind of bullish on creators, turning into entrepreneurs, because they're the people that have the built-in audiences. But what happens if you want to reverse engineer that? What happens if you're not the person that wants to be front and center,

to be the founder? Do you still think that you can't? I think what you probably have to do then is you have to find your counterpart. You have to find the yin-tier yang. You have to find someone who, you know, the things that you don't like doing, they love doing. The best teams that I've seen, certainly at Shopify, but skims, we were talking about your CTO recently. My old-time. My old-time favorite, I met.

It feels to me that over time, the best businesses have almost assembled the Avengers. What I mean by that is not that they're all superheroes, but they're all so different. Each of them individually have these very spiky objects, right? They're not well-rounded. In fact, the best entrepreneurs I know are not well-rounded. We're all kind of like spiky. We're really good at something and we're really bad at other things as well. And so if you know that like you're really good at production, find a really good storyteller.

If you're really good at creative, find a really good technology person. But again, that goes back to you still have to leave some breadcrumbs to invite that counterpart in. And I think that one of the best ways to do that is to share the story, the ups and the downs. So if you don't want to be front-facing, you don't have to be, but you definitely have to find someone who does want to play that role. Yamava Resort and Casino at San Manuel is California's number one entertainment destination for today's superstars. Catch the Jonas Brothers return to the Yamava Theater stage on April 30th, the powerful vocals of Demi Lovato on May 17th, and the signature Southern Country Rock of Eric Church on July 19th. Tickets on sale now at Yamavatheater.com.

Only at Yamava Resort and Casino, celebrating its 40s, anniversary. U.N. must be 21 to enter. Ambition comes in all shapes and sizes. At First Citizens Bank, we roll with your goals because we're built for what you're building. Fit for your ambition for Citizens Bank. You know, I really agree with that because we always think about those things as attracting customers, right? Like the reason that you're putting your story out there, the reason you're talking about your mission, the reason that you're building those followings is always about customers. But it's also about being able to attract to the right staff and the right people to come and join from the outset, right?

Especially like when I think about you, you fell in love with the mission of what this company could potentially do, not with the idea that you could scale like a bunch of stores. No, that was unimportant. It wasn't about the technology stack. It was about like what exactly is the mission of this company. What do you say to people that are trying to figure out like, what do I care about?

Like how do you, how do you weave those things together so that you can end up in a position where you're doing life's work? So I asked a few of our mutual friends, before this, I came on here, I did my research like you did. And I said, what do you think defines Emma as an entrepreneur? And the Venn diagram overlap of those reactions, the thing that most people said to me was, they talked about it on the couch. They said, I hope I'm not bushering this, but they said something, you created size 15 of one of your products. And I said, I don't know what that means. I said, well, at that point, no one had created, it was sort of like size 14 or size 16.

and you created size 15. And the reason that they told me about size 15 that you created was because what it said to me was, you always cared about fashion, you had a deep interest in fashion, but you also had a healthy disrespect for the status quo. Why is there no size 15? Not everyone is size 14 or a size 16. What about size 15? One of my friends and someone I really look up to, I actually wear as clothes every day, is James

Burs. James is a great guy. Graham is a great brand. It does become a very good friend of mine. James doesn't have small, medium, large. It's like sizes zero to seven. Why? Because James has a healthy disrespect for like, he's like, why would I, like a small

doesn't fit you nor does a medium. Why would I have to put you one of these boxes? So one thing that I think is important is, number one, if you grew up in a household that everyone in your, in your family was doing a particular industry or craft like fashion, that's cool. But if you didn't, first of all, you may have an advantage because you don't know what you're supposed to do. Totally.

The second thing is, I heard this great quote from Bill Gates, which is something like, whatever you did between the ages of 13 and 16 for fun is probably something you should consider doing when you're older. That's so good. And when I was 13 and 14, 15, 16, I was starting little companies. Not all of them succeed. I was in high school. I was a kid in South Florida.

But, you know, on weekends, I wasn't playing sports and I wasn't watching sports and I wasn't, you know, drinking beer with my friends. I was trying to figure out how to sell video games to bar mitzvahs. Honestly, every single person needs to pause and figure out what they were doing in those three years. Just write it down. They may not be exactly what you do, but there's always going to be whatever you were doing between 13 and 16 for fun, there's probably some aspect of that that is likely going to lead you to life's work. For Toby, it was programming.

He loved computers, so obviously he's programming now. That I think is really important. And when you combine what you were doing for fun, when you were a kid, with having a healthy disrespect for the status quo, you get to build generational things. Yes. So I think that's really important. The second thing is, like, back to this idea of having a good tribe around you, ask your tribe what they think you should do. Yes. Because sometimes we have, we get in our own way, we're like, I could never be in fashion. I'm not fashionable. Ask your friends and your family what they think, you know, what industry

you should be in. They may say actually, like, you yourself might not be fashionable, but you're always giving other people really great advice on fashion. And I see that across so many of our stores on shop. I mean, I have to tell you, that is so true. And having interviewed so many incredible founders recently, so many of them came to what it is they would eventually be doing because a friend said, you're always doing this and have you thought about that. I had the girl on who started the Shade Room the other day. And she comes out of this, you know, like whirlwind moment in her life. And she's just come off of producing a movie, doesn't know what's next. And a friend says to her, but you're always calling me up with all the gossip and all the tea. Like, you should, you should do that and put it out

online. And it's so interesting. And that's what it becomes. You know, it's so interesting because, you know, so you're saying people are going to see this and say, well, I don't know what my thing is. Another thing that I think I hear a lot of people say who are aspirational entrepreneurs is, well, it's too late for me or I can enter that, that industry. This is, I've never shared this story. So we have a retail space in Soho on Green Street. It's just literally just, it's called the Shopify retail space. And it's a blank canvas. Any Shopify merchant can use it. We do pop-ups all the time for the last three years. We've had Mr. Beast came in, did a Feastables pop-up, Brianna did a Fenty pop-up, Eminem did a mom spaghetti pop-up. We've had

new balance in. We've had some of the biggest companies on the planet do it. And I often ask the team, so it's usually Friday to Sunday. And usually on Monday, I ask, when did the lineup start? Because the lineup starting for it open is a bit of a gauge for me of how popular the pop-up was. So I asked all these times, and, you know, if it's a really big pop-up, like a fenty, for example, it's usually around 6 o'clock in the morning. Well, last week we had a pop-up. I didn't know, I'd never heard the name before. I never heard of the entrepreneur or the brand before. The line started at 3 a.m. So I was, so I got this. I got this. I got the summary at 3 a.m. The line started. I was like, wow. It must have been, you know, we have on running on Shopify.

We've all these huge companies on shop. Must have been one of these big ones. And they told me the name. It was Dairy Boy. Oh, I know that brand. I had never heard of it. Guys, that's a sign from God. And then I said, who's the entrepreneur? And they said, this woman, Paige. I was like, I've never heard of her.

So I did my research. This is a brand new company. Oh, yeah. Okay? Page is completely self-made. She started building her own following slowly on social media. Again, audience first, then turn that audience into a brand called Derry Boy. She had more traffic there than all these massive, established, incumbent brands

and I think the brand is only a year or two old. So what that tells me is right now is unequivocally the golden age of entrepreneurship. That's someone that I've never heard of and I don't mean to be disrespectful. No. But like the fact that someone unknown to me was the person that has had the highest trafficed pop-up store we've ever had in the history of this particular location. That gives me so much hope that anybody can do this. And honestly, it should give everyone so much hope because the idea that this brand, I mean, I think I found out about Dairy Boy two weeks ago, and it was the same thing.

I get a text. I won't say what it said in the text, but I get this text. I'm like, I have no idea of this is. And I'd like spend precisely three minutes. And I'm like, this is so hot. Everyone that I then text it to came back with the same thing. Oh my God. Like, this is so amazing.

And I think that that is like what is so, you know, I always think about it in the context of being in America and being able to live in this country where such extraordinary things can happen so quickly. But we were not talking about this brand even a year ago. Even if it's a couple of years up, we were not talking about it. And the brand that we're going to talk about... To me, it's just, it's so wild. That's right.

And the brands that we're going to be talking about in three years from now... We don't even know their names. They have not been created yet. They haven't been created. Someone watching this right now, I'm not joking, we'll create the brand that you and I'll be talking about three years from now. And they're not going to have money. They're not going to have experience.

They're not going to have any type of connections. They're just going to be someone that has a great idea, grit, and a deep understanding of who they're selling to. And that's why I keep saying this is the golden age of entrepreneurship. It's not about Shopify. It's not about the technology. It's about the fact that right now it is the best time in the history of the world to start a business. Oh, it just makes me so happy.

We're right on time. We're right on time with this. It's so perfect. I want to talk to you about longevity, right? Because again, you can start, you can get hot. We all know that businesses that have been there and then disappeared. I want to understand a little bit about given all your experience and what you've seen, how do brands and businesses create longevity?

Like, how do you stay in a place where your business can thrive and grow and you can build something truly great that goes beyond the hot moment and the lines around the block? So this is more for the people watching that, you know, that are sort of entrepreneurs, right? Like they're very entrepreneurial and maybe they're working a company. And maybe they're worried that the company is, you know, it's a large company. and it's been around for a long time. I had this great friend.

I don't mean to be name dropy, but his name is Richard Dixon. Richard Dixon was the CEO and president of Mattel for many years. He's now CEO of the Gap. And I got to know Richard really, really well over the last six or seven years or so. And I was deeply curious about Mattel. Okay, so just history, right?

Mattel was built in 1945. Two products started Mattel Barbie, because it was named after the founder's daughter. Funny, Ken was the son. And Hot Wheels was the other product. So they had two products. And they've done a number of, amazing well over the years, American girl came out and all that stuff too.

But something changed about five years ago at Mattel. All of a sudden now, they had these things called like Mattel creations. We're doing like these drops, like, supreme drops. You know, these like super hot drops were coming out. And they did the Barbie movie. And all of a sudden, like, Uno is hot. Like, what's going on? So hot. Hot in my house.

And I would ask, my house too. And I'd ask Richard, I was like, what's going on here? And he's like, because people are always thinking that there is only one way to do it. Rather, the way that him and Yanon, who's the CEO of Mattel thought about it, is like, look, we have a vault. In the vault, there's all this incredible intellectual property. Each one of these things has a consumer that cares deeply about it. And if we find the consumer that remembers playing Uno when they were kids and we sort of, you know, almost rebrand or ref- like, it's almost like a refounding event of these things. Amazing things can happen. Another brand on Shopify is Birkenstocks. Burkenstocks, I think, was created in 1775. Birkensox is not only a cool brand now. They're hot again. How does this happen? Because they don't necessarily believe that there is a certain way of doing things, right?

Whether it's collabs or it's finding new IP or it's new ways of selling these things. There is longevity in brands, but you have to have the courage to say, let's stop doing what we've always been doing. Let's find a new way to recreate these things. And I think, you know, Mattel has done it. Hunter Douglas, you know that company? Yes. They make blinds. Hunter Douglas, I think, was created in 19.

I know my retail history quite well. I studied the stuff. You really do. It's impressive. Hunter Douglas is still one of the most important home furnishing brands in the planet. And they're literally 100 years old. How? Well, go to the Hunter Douglas website. It's beautiful. It's well designed. It's fast. They're on social media. You're able to use augmented reality. They're adopting all these things. It's almost like these iconic brands have these refounding events. And it's always because someone within the company says, we don't have to do things the way it's always been done. We can take a brand new lens to this thing. And in the end up with these icons. I've read this beautiful thing. And I think you're absolutely right in what you're saying.

I once read something that Bernardo Noah had said about the LVMH brands talking about this idea of transitioning on the way up, of always being willing to change what it is that you do. and you have this core and you have the things that those businesses are known for, but you never, ever stay where you are. And I think that there is so much truth to that. Like you stay still, you die. You always have to have an eye to the future and an eye what's coming and be willing to change. That's right.

And it's just like you see that with the best celebrities, you see that with the best businesses, you see it everywhere, the ability to have some way of constantly reinventing what you do. And it might be exactly the same. same thing. It's just a different lens on the same thing. This idea of getting really, really comfortable with being uncomfortable is a major superpower for these sort of legacy brands, where they believe that they have to kind of stay the course in a particular way. That's not

where the magic happens. The magic really happens when they're able to go off course. And that's the reason why, you know, you have companies like 100 Douglas, 100 years later, who are still dominant. Still doing great things. Because they're like, they're not talking about what they were talking about 20 years. They're talking about augmented reality. They're talking about virtual reality. They're talking about agented commerce. They're talking about all these amazing things that a startup is talking about,

but it's embedded into a much more established organization. Yeah, and it becomes the culture of the place, right? To have the questioning, to do the different thing, to disrupt things a little bit. So your job is so much about helping businesses to scale. What do you know for sure when it comes to companies being able to scale? So scale is really hard because often when you think a scale, you think about losing the soul, right? That you think about, well, I'm getting so big. I actually don't think that that's always the case.

There are some companies, for example, that, you know, Cat Cole is a CEO of AG1. You know AG1? I love AG1. Great company. Kat's one of my favorite entrepreneurs. This is public information. AG1 basically has done $600 million with one single skew. They have one skew doing $600 million.

Honestly, I think I'm like a million dollars of that. That product is amazing. I love AG1 too. It's so good. So AG1. So is one? So is it a one skew? company? It's a one skew company until last week.

I don't know. I think of that. Okay? So one skew, 600 million. What's the new skew? Sorry, we're here now. They have a couple different flavors now. So what they did was they basically figured out that like for, I don't know, maybe they're a 12 year old company, 15 year old company, that one skewed, this is AG1. But they eventually got to a point where they said, okay, is it time for us to scale? Okay, if we're going to scale, what else are we going to do? So now they have a couple of new flavors. I think they also have something that you take before bed as well. But the brand. expansion of it is very thoughtful, very careful. And that to me is the best way to scale.

Back to our friend Ben at Jim Ashark, they really wanted to go into brick and mortar. But how does a direct-to-consumer native digital brand go brick and mortar? Well, they build these incredible physical experiences where there's a gym and a juice bar and you walk into, they have this great store on Regent Street. Yes, I love that store. It's a beautiful store. But when you walk in there, it feels like the physical manifestation of the brand. Yeah, you're right about that. So that doesn't feel like another sport store. You're right. Exactly.

Or, you know, Ronnie Kith. When you walk into a Kith, every Kith store feels like, the fact that Kith has Kith treats, somehow that makes sense. I cannot tell you, I just queued in Malibu for 50 minutes to get my set kids a Kith ice cream. I'm like, guys, can we just go there for ice cream? No. Because they believe like that. Yes, it really does.

So the right way to scale is to scale in a way that feels authentic. And how do you scale authentically? You have to understand your customer really well. So if there was a Kith restaurant, does that make sense? No. Well, they partner with Siddles instead. And that's the, that's the Kith restaurant. Yeah. So there is this way to scale and it stays authentic. But the brands that try to be everything to everyone, that's usually where they die. That's usually death to a brand. Where do you see entrepreneurs fail? What are the pitfalls that you see people fall into over and over and over again? And there's a lot of people that like to play entrepreneurship. I mean, you know, obviously we're here talking about all the great parts of entrepreneurship. But just to say the thing, I mean, most businesses, fail, right? The good news is that in 2025, the cost of failure is about as close as zero as has ever been. I think it's really important just to stop you there because it's, I don't think people understand this part. Most businesses fail. That means you have to expect for everything

not to turn out. And we do a disservice, maybe do this better, whereas I talk about in my younger years, the DJ company, the T-shirt company, I don't talk about all the stuff in the middle that didn't go well because it doesn't sound as good. The story isn't as, as, as glamorous are elegant. But I don't want to necessarily glamorize entrepreneurship. I still have sleepless nights, even now. I still, I work 80 hours a week, some weeks. It's really hard. There are easier ways for me to, you know, to make money. But for me, there's nothing else. I think it's the greatest, the greatest tool. So where they fail is they believe it's going to be glamorous. They, they see the highlight real of entrepreneurship, but they don't see the sleepless nights. And part of the thing, I

think that people that have had success need to do more of, and I certainly need to do more of this, is talk about some of the downsides of it. It isn't linear, right? It's sort of this like ups and downs and the highs are really high and the lows are really low. But if you, if you love it, there's nothing like it. So I think ultimately where entrepreneurs fail is they give up way too early. They try something. It doesn't work. They say, I'm no longer an entrepreneur. whereas the ones that succeed have this unwavering grit where they can just keep going. And you punch them in the face and they get up again. You punch them in the face again, they get up once again.

And I've seen so many of your interviews with all these incredible people on the show. I know some of them personally, they've had a ton of failures, a ton. They've failed more than anyone else I know. In fact, the more successful you are, the more failures you have under your belt. If you think you can cruise, you know, I got a chance. to meet Mr. Beast and Jimmy and the whole team. And you look at Feastables and it's incredible, obviously, this is a company that's now rivaling Hershey's, right?

Not. And you think, well, Mr. Beast has it so easy because, you know, he has a, no way. This guy, first of all, they're all held up in like in North Carolina in this like commune all together. They eat, sleep, drink together. All they do is think about their business and their videos and how to engage their audience. None of it is easy. And I think if you think it.

it's going to be easy. It's probably not for you. But if you go into it with this growth mindset that you will have more personal growth through the vehicle of entrepreneurship and you enjoy this idea of getting really comfortable with being uncomfortable, I think it's the best thing in the world. Today we helped a latte for Sam coffee shop get an insurance quote simply and easily and made sure a floral delivery van was able to make someone's day. We're the Hartford, with decades of experience ensuring millions of unique small businesses. When it comes to your small business insurance,

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It's a simple way to make sure your listing is the first candidate C. According to Indeed data, sponsor jobs have four times more applicants than non-sponsored jobs. So go build your dream team today with Indeed. Get a $75-sponsored job credit at Indeed.com slash podcast. Terms and conditions apply. One of the things that we're trying to do on this show is not just to talk about failure and admit failure, but really to dissect it, really to understand, like, what are the patterns, what happens, how much ownership do you have to take about that away from that? Because I think that typically, and especially in the culture that we're in now, it's not something that you put on your Instagram. It's not something that you speak about.

There is a certain amount of shame attached to it. But as you know, and just to your point, the most successful people we know have fouled miserably. have failed big, have failed multiple times. And still fail. And keep failing. And in fact, the reason they're so successful is because they've built a resilience to be able to fail and look at what happened and go back and try again and again and again. What's the lesson that you've learned the hard way?

Well, a couple things. First of all, I think for a long time, I felt that I had to be very good at a lot of things. Over time, I realized that I sort of feel like there's different phase of companies. Like, at least for me, kind of the early journey was jack of all trades. Like everyone do everything. It's like manic when you're just starting a company. I was the head of sales. I was also the janitor. Like you do kind of everything. And then kind of the second phase is sort of what I call a triple threat. So you pick two or three things and you get really good at those things as well. The phase obviously that we're in now, the chop phase and that

I'm in right now is really more of this spiky object where ultimately I get to settle into the thing that I think I one day can be world class at that I'm really good at that creates the most of value and that shopping really needs, which at this stage is storytelling. Right. And whether that's to investors or to the media or it's to partners or merchants or the general public, my job is to make sure the whole world knows about the Shopify story, which really, you know, Shopify is the entrepreneurship company. So it's easy for me to do so.

But I was very hard at myself in the early days of like, you know, I was CEO for six or seven years of Shopify. And I think I was an okay CEO. I think I'm a much better, you know, much better in my role that I'm right now as president of the company as a public-facing person, as a person out there telling the whole world about why they should think about entrepreneurship. And I thought having a big team was some sort of barometer of success. I thought having to be everything to everyone is a barometer of success. And as I get older and a little bit more mature, I guess, I realize that that's like no one is good at everything. And, and, and, um, as I get older and a little bit more mature, I guess, I realize that that's like, no one is good at everything. And, I'm now settling into this idea that finding your thing early in life and working on it and developing it and finding the way that you can get the most value out of it, which again, this is for me a storytelling and through the lens of Shopify, that really is what matters most. Were you able to come to that conclusion yourself or did you surround yourself with

amazing people that told you? So look, I'm a big believer in mentorship. I think I know you started this show really because you didn't have mentors. I had a different sort of path there. I've had mentors my whole life. But I never really called the mentors. It was sort of like a personal board of directors. And what I realized early in my life was that none of these mentors,

I could cargo cult all of them. I have a mentor who helps me, you know, invest. He's on like his third or fourth marriage. I mean, this is not someone I'm ever going to get advice. I love my wife. I want to have a great marriage. But like, he is bad at being married. You're like, show me the money.

Yeah, no, he's bad to be married. When we had our first, my wife and I had our first child, Bailey, nine years ago, I looked around and was like, who I think is a really good parent? I ended up finding someone who just always felt like he was just a great dad. He was their first kids, understood his kids. And so I was like, you're going to be my like parent mentor. And so I found someone who was when we went, but 10 years ago, shop by went public. We had our IPO. I started looking around for who do I think is really doing a great job running a public company. And I brought those people in. And so one is, I think this idea of creating a personal board of directors is really important. I think you should have many, not like, not thousands, but like I have five of them at any one time. And then eventually you learn all their tricks and you have to sort of cycle up, find someone new that can bring you new perspectives. And so I've sort of been doing this personal board of directors thing now for since I was 15 or 16 years old. Wow.

And back to the no cringe thing, when I see someone out there, whether I know them or not, who I really admire and want to learn from, I am. obnoxious about getting their attention. I will, no cringe. I'll never be disrespectful, but I will be on them and find a way to get some time from them. The person board directors thing, it isn't a casual thing. I will say to them,

look, I am getting a ton of value here about how to be a great husband to Lindsay. I need, like, I need more time here. And like, I don't know what I can do for you, but like,

will you spend an hour with me every four weeks, virtually over coffee, what have you? And I've been running this playbook on this person board of directors. I'm 41 years old, so I've been doing it for like 25 years now. That is just wild. What's the biggest decision they've helped you make? Would it be the decision to change your position? That's been a big one for me. It was also, you know, I had sort of this thing about like, well, there's like my life life and my work life that I had to separate my kids

and my wife from Shopify. And actually what I realize is for me, this idea of bringing it all together harmoniously is incredible. Having Lindsay at the IPO, my wife at the IPO, my wife at the IPO, bringing my, we have this thing called Builder Sundays. So every Sunday, our offices are open and entrepreneurs in Toronto and Montreal can just come in to work from Shopify. And I used to want to go there to support the entrepreneurs, but I feel bad about Bailey and Zoe. My daughter's not being there. Well, guess what? Now I bring them and they love being there. Of course they do. They have their own, you know, I wrote a kid's book called We Can Be Entrepreneurs. I wanted to ask you about these kids. Yeah, it's a really cool book. It's really great. It's coming out in a few weeks.

But I wrote this book because I felt that most schools are not teaching entrepreneurs. In fact, most schools have this thing where they say, what do you want to be when you grow up? And they give you a list. And it's like firemen, doctor, lawyer, actor, magician. Like, magician's on there, but like entrepreneurs not on there. So I wanted to effectively create a bit of a Trojan horse to get it into the school system. And I did it through the book. But now I bring my kids to build her Sunday.

My kids love it. So this idea of incorporating all these elements of my life together has been really amazing. And that was a mentor of mine who said, you are separating things that don't need to be separate. There isn't like work Harley and personal Harley. No, and it can't be because I feel like, again, you sit at this company that has a $200 billion market cap. And by the same token, like you are writing a book

and you're obviously a very engaged father and you have a wife that's just the one wife, which is so lovely. I love her. She's the best. I'm sure. Lindsay's amazing. But you also have a tea brand. And what strikes me about you and I did my own homework was how can next.

you are, right? Like there is this idea that someone who has done, that operates at this level, that has done what you've done, becomes very disconnected from the thing. The idea that you are on the phone to my CTO before you got here, that you understand the cues around the block, that you're so engaged that you would go in on a Sunday, what allows you to operate, like, on all of those levels? Because I think it's something that people really, really struggle with, especially when you're in a company, it grows really fast. You can become disconnected. I think it's poison. A lot of people assume it's because I'm extroverted.

I am a power extrovert. It's not about extroversion or introversion. I think it's about energy levels. I have filled my life. Why, how did you keep the energy? Because you must be exhausted. You're not exhausted. No, I'm not.

Because, and I mean, this is not a weird flex, but I did an alter endurance race this weekend called 29029 that Jesse Hitzler started, an incredible race. I mean, I've seen it. You saw it? Yeah. So I climbed a mountain for 36 hours this weekend. I watched it.

I was. Yeah. Yeah. It's basically you emulate climbing one Everest. No, I'm not exhausted because I feel my life with things that are deeply meaningful to me. I'm not searching for happiness. I'm not searching for some gold star. I'm searching for things that are meaningful to me.

Being able to lead this incredible company called Shopify is meaningful. Being a great dad is meaningful. Climbing this mountain on Saturday, Friday and Saturday, and then seeing my kids at the finish line. I started to cry when I saw them was meaningful to me. But I say no to everything. else. I don't have side quests. It's all main quests for me. And I really believe that people, it's very easy for people that are busy to adopt these side quests. One more thing. One more,

you know, like join my board, come to my event, you know, go to my networking thing, go to my conference. I say no to most stuff. If it's not related to Shopify or my family or something that is deeply meaningful to me personally, the answer is, can I swear on this show? Yeah. Fuck no. Yeah. The answer is fuck no. I need to, like, my energy is what allows me to do these things, and I will protect that energy and I will protect that, I will protect that by all means. But it means that I have to say no to a lot of things a lot of the time. And in some cases, it manifests in people, you know, I had people in my life, sometimes family members who were kind of energy vampires. I would, you know, I'm trying to do, be my best version of me and meditate and work really hard and be a great dad and

and then I go to these family events and they just suck the energy out of me and I eventually had to politely say I can't come anymore and I'm not trying to be pretentious or you know I'm not trying to be mean or anything like that. It's just I'm trying to live this very meaningful

intentional journey and this is not allowing me to do so. So how have you made the list of the things that get your energy? Like how do you because again you seem to me as somebody that is so considered how do you decide what gets your time.

Yeah, I mean, look, sometimes you have to be thoughtful about it. You mentioned the tea company. So during the pandemic, I sort of had felt that I had not, I'd not built a store on Shopify since my first store back in 2006. So it had been... You wanted more Shopify. It had been 14 years, effectively, since I built a store from scratch on Shopify,

and I really wanted to put myself in the shoes of what it's like to build a brand-new store on Shopify. So my best friend and I started Firebelly T, and we got to work on and I got to play with the new themes, all the new functionality. And then eventually started to do pretty good. You know, David, my best friend is the founder of David's T. So he knows a lot of a T. I know a lot of e-commerce. And eventually, David and I said, okay, it's now time to hire a CEO.

And so I don't do anything in the Firebellity anymore. I did the thing that I wanted to do, which is start a brand new business on Shopify. If it was successful, I knew we'd eventually have to back off. If it wasn't successful, that'd be okay too. But eventually, I backed off and did that. You know, when it's earnings week, you know, our quarterly earnings, this is again back to the incorporation of everything. My wife, Lindsay and my kids, like, know it's earnings week. And they know that, like, that's going to be a week where I probably am not going to be home a lot because that particular week, like, I'm in earnings mode.

So I'm just very thoughtful about that stuff. And again, like, it's not that I'm being a bad dad or a bad husband. Lindsay's like, look, four times a year, I have this thing which requires 100% of my focus. there's no extracurricular activities during the earnings period. And by doing it that way, and I schedule everything,

everything is in the calendar, morning meditations in the calendar, walks with Lindsay's in the calendar. I mean, Jesse Hitzler, has become a friend. He's sort of the one who taught me most about the power of putting everything in the calendar. He's got this big thing called

the best calendar, right? First of all, I love Jesse Hitzler. He's amazing. I feel like I learned so much from him. He's one of the great people to follow But as it pertains to, like, family and business, I think he's one of the best. He's knocked out of the park. And so he's become someone that I really admire there.

But the way that I do it is, I'm incredibly intentional about the things that are important to me. And if it's not important to me or it's not meaningful, the answer is no. It's just got to go. Yeah. I mean, I think that's really a big thing for young founders because your energy is all you have. Yeah, well, Ben called me when Ben Francis called me when he was having, he had twins. and he called me when he found out he was having twins. And we talked about this idea of, you know,

how do you run a company like Jim Shark and be a good husband and be a good dad to twins? You know all about twins, which is very, very difficult having newborn twins. And I told him, I was like, look, here's what I know. But like, this is the things that I've learned, but you need to go and also like ask other people to and build your own version of it.

That's the thing about mentorship is that we always assume that I'm going to like take what this person did and incorporate. And do it verbatim. No way. It never works. What works better is to take little bits and pieces of insight from different people that you admire

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Stanley Steamer.com. So you're saying with Hilton Honors, I can use points for a free night's day anywhere? Anywhere. What about fancy places like the canopy in Paris? Yeah, Hilton Honors, Baby. Or relaxing sanctuaries, like the Conrad in Tulum?

Hilton Honors, baby. What about the five-star Waldorf Astoria in the Maldives? Are you going to do this for all 9,000 properties? When you want points that can take you anywhere, anytime, it matters where you stay. Hilton for the stay. Book your spring break now. What are the things that you do and that are non-negotiables to you when you think about what makes your life work, what makes you able to do all of the things you do, you just say,

I can never skip this. I've had anxiety most of my life. I didn't know what it was when I was younger. Teachers would tell me that I was distract. Like a lot of entrepreneurs kind of have this, I bet. but teachers thought I was distracted. I couldn't sit still. I'm very hyperactive.

Well, it turned out that I had anxiety. And what I realized was actually one of the great ways for me to not, I can never get rid of it, but tone it down or to harness it is, is with an eight-minute breathing extra like meditation. It's not fancy. I do box breathing like four in, hold, four-out hold. It's very, very simple. I do eight minutes of it every morning.

It's in my calendar. My team's here. You can ask them. It's in the calendar. That's something that I will always do. I always, Friday nights. I'm not religious, but I'm proud Jewish entrepreneur. We do Shabbat dinner with family.

And I do a Shabbat Shabbat Shalom message to the whole world on social media with my family because it's just we're just, we want to wish everyone. We say it's very simple. We hope you had a great week. We hope you have a great weekend Shabbat Shalom. And it's me, Lindsay, Zoe, Bailey. We do it every single weekend. And it just, it brings in the weekend, the Shabbat together.

And so there are things like that, these rituals that are so important. And I think rituals really, really matter. Oh, me too. And creating rituals where, you know, once every two weeks, I have dinner with my best friends. We never skip it no matter what. I'll fly home and then fly back to wherever I have to be if that's required. But creating these rituals and looking at these rituals and saying, are those the most important things? That has been very valuable to me. I just love that you say that. I'm such a ritualistic person myself. It's a really nice thing to do.

I mean, and it is because, again, I think when you have so much going on, and when you're in these, like, you know, because again, we have times of, as entrepreneurs, of huge uncertainty, something that grounds you and brings you back to what you know is true and what you can control. And for you, it's the family, you know, for me it would be like, even just like having a cup of tea in the morning. They're just doing it mindfully and doing it like, you know, purposefully and doing my meditation. again, like I think that people think so often about things like that as taking time. And I'm like, no, they give you time.

They give you energy. I heard this great interview with Andrew Ross Sorkin interviewed Jeff Bezos recently. And I just stumbled upon. Oh, the deal book interview. Yeah, exactly. It was so good. And so Andrew's a great interviewer. Andrew said to Bezos, he said, what's your morning routine like?

And Bezos, who is one of the best entrepreneurs in the world, I think, said, oh, I think he said, I just puts around in the morning. Yeah. Just saunter around. until about 9.30. I was like, what am I doing? And I was like, whoa. Like, he's like, you know, I checked my phone.

I read some newspapers. I have coffee. You know, I hang out with Lauren. Like, he sees his wife. Like, it's, like, I loved him saying that because it gave me permission. Yeah. It gave a lot of people permission to be like, you know what? In the morning, I also like the puts around.

Like, I also like a cold plunge every now and then, but I don't do a cold plunge every single morning. I think it's really important. Back to the energy thing. I think the, I want to be able to do this for a very long time. If shoplight will allow me to be their president, I'd like to do this. Like, this is what I want to do for a very long time. How nice to be in a job where you can say that.

It's true. So in order for me to do that, I have to protect my energy. Yes. And I, because I believe that if you are leading a company of any size, you must requalify for your job every year. Oh my gosh. I read that you said this somewhere else before. And I believe that.

Do you believe that for everyone in the organization? Yes, 100%. Oh. And to requalify that. qualify means, you have to effectively grow at a rate that is greater to or equal to the rate of change or of growth of the company. And when you're working for a company, especially a high growth company, the rate of change is rapid. So this requalification, it's not like, I don't measure it per se, but I believe that Shopify should always have the best, like, whoever is the president

Shopify should be the best person in the world. And I like, I like, I like, I like, the pressure and the growth that insinuates that I must have in order for me to to re-qualify. I also believe that I have to re-qualify to be Lindsay's husband every year. And I have to be Bailey and Zoe's dad every year. And requalification could sound like something negative, like, well, you're always kind of, no, it's not like that. I have a growth mindset about this stuff. I believe that requalification means I've got to get better at this stuff. I've got to be a better dad. I've got to be a better president of shopping. Shopify, I've got to be a better husband. And it motivates me to always think about how to be

constantly improving. That doesn't create stress or anxiety. It actually makes me, it's sort of personal ambition in many ways. Holly, how do you actually go about that? When you're thinking about re-qualifying to be the best dad and the best husband, as well as being the best president at Shopify, what does that actually look like? Give me the things that you would do. The husband and the father thing is really, really difficult because there's a lot of things that are unquantifiable. I'll often ask my kids, you know, how can I be a better dad? And, you know, it's funny. You can, if I have a six, you know, Zoe's six and Bailey's nine, you know, they'll say, well, take us for more ice cream. And like, I mean, there's a little bit of truth in that, which is like, spend more time with us.

But for example, there was a period of time where I get home, I always had dinner at the family. I get home for dinner and or a Friday night. And I was physically there, but cognitively, I was not there. And so getting better at that particular role meant, okay, if you're going to be home, be home. And Lindsay and I had a discussion, she's like, look, like, you're busy. So if you're coming home, like be home, if you can't come home because there's someone going to the office, she's understanding. She's like, just finish that up and then finish that and then come home and be, like,

be present with us. So that one's a little bit more subjective, a little more difficult. But you're asking your family questions and you're taking your cues from them. You're saying, I want to meet the needs at this particular person. individual and therefore I'm going to consult with them as to what do they need from me. And so, yeah, and a six-year-old, consulting with a six-year-old is, I mean, you get a lot of fluff. You also get some really beautiful things. Listen, I'm telling you the kids, will tell you the truth.

They'll tell you the truth. They're not trying to spare my ego or my self-esteem. They don't give a shit. They're like, this is dad, like, you know, you say we're going to watch a movie together all the time on Sundays, but like, you're always checking your phone. Yeah, you're on your phone. And I'm like, all right, you're right. You're absolutely right about that. So instead we go to Builder Sunday at Shopify and like, I'm on my laptop. and they're on their laptops. I'm like, look, we're doing this together.

At Shopify, it's a little bit different. Shopify, I'm actually able to. So back to earnings, for example, I watch a lot of tape, meaning like, just like an athlete will watch tapes of past games. What are you watching tapes of? Of earnings calls. I'll watch, you know, there are some really amazing business leaders doing earnings, whether it's on CNBC or on their earnings calls or on a podcast,

and I'll listen and I'll watch and I'll hear their voice inflection and I'll hear how they weave together a narrative. and I'll hear how they understand some nuance metric. You are an entrepreneurial athlete. I love that shit. And so I'll watch the tapes and I'll say, okay, I really like how they did that. Or I really like how they did that.

So at Shopify, it's not necessarily like a really objective, but in my role, I'm like, okay, who's doing this really well? Yeah. And there are some people out there that do things really, really well. And I watched that and I try to, and then I watched tapes of me a year ago when I was on, let's say, you know, squawk or something. and I'm like, oh, I said, I'm a lot.

Or I didn't necessarily answer the questions directly as I should have. Or on the earnings call, you know, I didn't say the thing that I should have said. So in that way, it sounds like I'm putting a lot of pressure myself. No, you're in a constant cycle of improvement. That's it. That's just who you are. And that creates a lot of meaning. You can hear the growth that you have.

You can see the growth that you have. That's such a cool way to live your life. I don't want a plateau. I want to be the best version of what I can be. I'm nowhere close to being there, but that's what makes it fun? What does it mean for staff? Like if you're an ambitious person right now sitting at home and saying, you know what, I have been a bit of a stalemate.

I've plateaued. I actually want to be one of those people that re-qualifies for their job, even if the company doesn't demand that, that's what I want for myself. What do you say to those people? So Chauvelay has about 8,000 people at the company now. That's a lot of people. That's a lot of reconfigure. It's a lot of qualification.

On a weekly basis, I constantly find someone in the organization, not even on a, like somewhere in the organization, they might not even be one of my teams where I'm like, wow, what that person's doing is amazing. And the thing that they always do that gets my attention is they're too good to ignore. They go well beyond what is asked of them. They may be in the revenue organization or the sales org or they may be in the marketing team or in engineering or product. and they've gone so far beyond anything that I've done. Or someone like Mehmet, your CTO, will call me and say, I was randomly on a call with five of your engineers

and this one engineer figured out a way to solve this problem that I just thought was like so creative. And so if you're listening to this and you're an organization and you want to find your own path a way to accelerate your career, just be too good to ignore. Forget, I mean, obviously do your job really, really well, but forget the parameters or the gates of what you're supposed to do. Just be too good to ignore.

And like, that's it. That's the secret. And I see that all the time at Shopify. And frankly, a lot of those people that I find in the organization in a different team, I'm like, look, I'm going to like take you and bring you in here. And we're going to do this really cool thing together. You know, the person that runs a brand at Shopify. So like if you think we do about like the retail space or we do with Mr. Beast or the

Shopify Mileson Awards. which you've gotten a lot of, I've delivered them a few to you as well, our version of like the Grammys. Or we do with the sphere for BFCM. The person that runs that, he started as my intern. And now he's running like, he's probably one of the greatest brand executors on the planet. And he started as my intern, you know, 10, 12 years ago, 14 years ago. I mean, it feels so simple to me because I say the same thing all the time. If you want to get noticed, if you're somebody that wants promotion, you want bigger responsibility.

It's like you have to just be excellent at what you're doing right now. You be excellent at that and you go above and beyond. It's so seldom that people are not noticed. Because most people don't do that. Most people... No, of course they don't. If you're working at Shopify, you're working in one of your companies, Emma, you're already like great at what you do.

Otherwise, you would never get in the door. So the common thread or the floor is already very, very high. So I get that it's really difficult if you're at a really great high performing organization on high performance sports team. But if you can go above me on that and you can be so good that it's difficult to ignore you, trust me, we all notice these things. Everyone notices. Everyone notices. Everyone notices.

And you know what's so interesting because you kind of collectively like raise the bar of everyone else around you? And I feel like that's why those people are so important in an organization. And my expectation is not everyone should be like that. But when we talk about ambitious people, people that really want more for themselves, so much of that. that has to come from you. So much of it is about starting with yourself. What am I in control of? What can I do? And that idea of re-qualifying for your own job every single year is a really good one for people. Because you can do that. You don't need anyone to give you permission for that. It's like you can do that all by yourself. And honestly, if you're an entrepreneur, you kind of have to requalify anyway. You don't have a choice.

You have no choice. Because now your company is re-qualifying for the patronage of your customers. of your consumers. No, you're absolutely right, because if you have a good company, the company's doing that as well, because you can't be doing what you did, you know, eight years ago, 10 years ago, 15 years ago, goes back to the beginning of this conversation. Yeah, you hear consumers say, oh, I love that company, but they've lost their way or lost their soul. You know, they got acquired by some big company or something. The reason that some companies, when they get acquired by some bigger company, stop, you know, hitting the mark is often because they're part of a larger organization. Everyone's doing good work, but no one is going above and

beyond. And if you were a company and you're a person that goes above and beyond in a consistent way, you win. Game over. Yeah. What do you say to people who are ambitious or they want to become founders, but they're also very conscious of work-life balance. Do you have an opinion on that? Yeah, I think work-life balance is very dependent on your particular circumstances. And there's a period in your life before I was married before I had kids where I was able to work 80 hours a week all the time. 80 hours. It's a lot. And then I, you know, when I had newborns, I wasn't able to work 80 hours. So I think everyone needs to kind of find their own version of it. I do believe truly that there is like, you don't have to work 80 hours a week to perform well, to be a high performer.

I know people that work 40 hours a week that are some of the greatest performers ever, they're just incredibly efficient with their time. So I think this idea of work life balance is a little bit of a misnomer. I think actually what we're all searching for is like some sort of harmony. There are some Saturdays where I have to work. And there are some Thursday afternoons and I go for a walk with my wife. That's my version of harmony. It's a great answer. I heard you say somewhere that you wish that your kids had known you pre-IPO,

which I thought was so interested. And I always think about so many successful people I know have concerns about their kids. They think, you know, it's like how my kids are going to be gritty. My kids are growing up so different to me. What's your point of view on that? I mean, I wish my kids were pre-IPO babies. I don't know if that's a real term.

It sounds so ridiculous, but it's true. Because there is a little bit. Are you out there trying to kind of like manufacture hardships? No, I'm not. So actually, in truth, I'm really glad you brought that up. No, I think like manufacturing, you know, scarcity is silly. I'm not going to pretend that there are like that, you know, we're not okay.

We are poor immigrants the way my father was. However, you know, and my wife is, who's much smarter than me and psychotherapist and incredible woman, she'll often say she's like, look, they're not, they weren't there pre-IPO, they don't remember the hardship and the tough days of Shopify. I don't remember, you know, the times where we struggled to cover payroll or where we weren't sure if we were going to make it. But you can tell them that. You can share with them the stories of that as well. And so that's what I do. I share with them all the time what it was like at the beginning, what it was like, you know, when we were struggling. But I think manufacturing some sort of false

sense of disparity is ridiculous. I also don't want to deprive myself of what I've earned. I didn't grew up with a lot. So now that I have, you know, that I have means, I want to enjoy it. I think it's part of working hard is to be able to enjoy the fruits of your labors. But I want my kids to know that, first of all, I'm successful. They are not. They have to prove themselves as well. Now, they're going to have, you know, they're going to have a great support system. My wife and I will never than we can to support them. I want them to know what it took to get here and not think that this all happened accidentally. And one of the reasons that I like some of these, you know, some of these projects that I have, whether it's, you know, big shot, the podcast or it's writing the

kid's book is, I don't know how the kid's book is going to go. It's, it's, I've never written a book before. Certainly not a kid's book before. So I share with them the story of like, you know, I wrote this book. I want someone to publish it. A couple publishers said no. I told them about that. They're like, why, Daddy? Like, it's such a great book. I was like, well, it's because they don't know if it can sell. I explained to them what publishers look for and distributors look for. So I try to share with them the anecdotes along the journey. And if we can be entrepreneurs is a great success one day, which I hope it is, then I want them to know, oh, right, like all these different things that we did

led to this success, that it wasn't easy. I want them to have some grit. I want them to feel like they, I'd love them to be entrepreneurs, but I realize they may not be. But I want them to know that none of this comes easy, but it's all accessible. Yes. I think it's a really great lesson for kids, you know, for them to understand the journey. And I always think about, you know, because I leave the house every day and ultimately, you know, I leave my kids behind. But I think it's so valuable for them to see what's happening in my work life.

They hear about it. We talk about it. They see the steps. They know what's going on in my life when something really doesn't work out. They know when there's something to celebrate and we're like, great, we're going to celebrate this on a Friday night. But that is invaluable. Totally. We have a family motto, which is how you do anything is how you do everything. Oh, it's one of my favorite things to say. I say it almost every day. So if you ask Zoe, who's six years old, what is her family motto? She will say, how you do anything is how you do everything. That's a great one. And part of the reason, to me, like what that is all about is about intentionality. The intentionality that I put into

my work is the same intentionality that my wife puts into, you know, making Shabbat dinner to her for a family. There's a great deal of care. I actually think that's really what it's about. In the week before earnings, for example, my, my, My daughters will come into my home office and they'll see like papers everywhere. It's late at night. They'll look, what are you doing? I'm like, I'm studying. And then they'll see me on TV the next day or the week later.

And they'll be like, Daddy, it's so great. I was like, why did I do great? And they're like, because you studied. I was exactly. I want them to see, you know, the work, like the actual journey and the destination. Yes. And I think a lot of successful people only show the destination. And they don't necessarily leave enough breadcrumbs for their kids.

I guess what I want to ask you is what gives you hope about the next generation of founders and entrepreneurs? I think it's in some ways easier, in some ways harder. I think this idea of, we were talking about celebration of entrepreneurship, that sometimes we over-glamorize it. It's not great to over-glamorize it because it gives off the impression that everyone can be successful. Not good.

What is good is that more people believe that they can be entrepreneurs than historically. In fact, if you look at, I think it was 2024, the United States had the most amount of business registrations in the U.S. and 2024 since like 2004. So more people today. Trying to even in the company now. That's right. Yeah, that's right. But more people are trying to have an entrepreneurship today than ever before,

which to me speaks to the fact that people believe that they can be entrepreneurs. I also think that entrepreneurship, at least from my father and for my grandparents, my grandmother was also entrepreneur. My grandfather sold eggs at a farmer's market most of his life. For them, entrepreneurship was, wasn't something that they wanted their kids to go into. It was like, Harley, we struggled. You need to go be a lawyer or a doctor. Please do something safe with this education.

That's no longer the case. I think that now it is, and again, what I'm trying to do with the book is trying to make it so that parents encourage their kids to consider this thing called entrepreneurship. Because I do think it's the greatest way to find self-actualization. It's the greatest way to be creative, but also to build something that is deeply meaningful. So that gives me great hope. I think that the celebration of entrepreneurship, again, there's a downside to it because if you don't succeed in the first one, you assume you're not an entrepreneur, which frankly is not true. If you have ambition, if you have ideas in the shower, you are an entrepreneur. Whether you do something with it is another story, but that is the prerequisite for it as well.

But the other thing I got to say is the velocity right now is unbelievable. Companies that didn't exist two years ago are now incumbents. That is unbelievable. Meaning like they've gone from their mom's kitchen table to being billion dollar companies in two or three years. That used to take decades. Yes. And so it's a combination of technology and a combination of incredibly smart and ambitious people. It's a combination of leverage. But if you combine all these things, you know, it used to be that the incumbent, so basically the established companies were impossible to disrupt. Not anymore. Not anymore. Not anymore. And in fact,

consumers prefer the insurgents, prefer the startups. Which is why so much of what you've said is so true, because when we talk about founder-led businesses, giving a voice, giving a personality, giving heart and feeling, that's what people want right now. And it is impossible. I'll take that all day long. It is impossible to compete with a deeply convicted, like a founder that has so much conviction, a founder that deeply cares about their product and their company. There's no way of big company compete with it. So instead of having these big companies that stay big forever, you have these beautiful insurgents that are creating not only new categories of products

and businesses, but are giving other people all this inspiration and aspiration that they can do it to. And my hope is that in the future, more people try their hand in entrepreneurship, not because they want to make a lot of money, but because I think it's the easiest way or the best way to find your life's work. I love it. That's just the most beautiful way that you could end this conversation. It's so amazing to talk to you today. I've left with such a great feeling for the work that you're doing and this idea of constantly being in motion and becoming. It's like a gorgeous conversation. Thank you. It is a great honor to be on this show, Emma. It is a great honor to be a small part, very, very small part of your journey as an entrepreneur, watching you build company after company

and the way you do it with heart and intention, the way you inspire so many others to do it, the way you do it with such, I don't know, you have this casualness where you make it accessible. That's exactly what entrepreneurs should be. That's what you're trying to do. You don't learn entrepreneurship anymore at HBS. You learn it on shows like this and you learn different people like you. And I think that a lot of people have, I think people get great value from hearing how you've built what you've built. And it wasn't easy and it's still not easy and it's never

going to be easy. And that's kind of the point. That's the point. But I think, I think this, I think what you're doing here is incredible and I'm so, so humbled and proud to be a little part of your journey. Oh, thank you, my dear. It means a lot coming from you. Let's do a quick rapid fire. We'll make it rapid. Okay. Okay. First thing you do when you wake up. Meditate. I knew that. And it's in your diary. The last thing you do before you go to bed at night. Kiss my wife. Oh, so cute. What is a small bit of that you think is killing it right now? Small business that I think is killing.

Ember, the mugs, the heated mugs. I drink coffee every morning. Ember is such a great company. No one knows about it. But if you drink coffee and you have it on your desk, Ember keeps your coffee in the mug or your tea at the perfect temperature all the time. It's amazing. First of all, I am buying that immediately.

Oh, it's amazing. I'm buying it immediately. I hate cold coffee. It's ever a cold tea. Incredible company. Ember, okay, going to buy it immediately. What are you currently? aspiring to in your life?

I want to be a world-class storyteller. What a great aspiration. What is a book that changed your life? Two, when I was 13, someone gave me a book. It's a very cheesy book, but it's called Rich Dad, Poor Dad. And it's an amazing book, and I encourage, if any of you have kids, to give it to them, it just talks about how, it taught me about money. It's a small thing, but, like, you know, it talks about, it teaches you the base of compound

interest, the rule is 72, and it teaches you about investing, and, and, and, it teaches you about investing, and how you can, you know, instead of saying I can't afford it, figure out how you can afford things. Rich Dad Port, I was a really great one. Who gave you the book? An uncle of mine gave it to me. It's written by Kawasaki, is his last name. And then a recent book that I read a couple years ago is called Anti-Fragile, by Nassim Taleb, which is a fascinating book.

But basically, there's traditionally two systems. There's like, if I drop this and it breaks, it's fragile, and I drop it and it doesn't break, it's robust. But Nassim Taleb introduces a third system called Anti-Fragile, that something when you drop it actually reassembles stronger than it was in the first place. The immune system is a good example

of anti-fragility. I think this idea of anti-fragility is really important for entrepreneurs. It's back to that idea of... You just told me. It's back to that of a re-qualification that like sometimes when you're going through the stuff and you break,

you actually get stronger over time and anti-fragile as a concept, I think is beautiful. That's a fucking nugget there. That's like maybe the best thing that you've said like, And you said a lot of good shit, but that was a really, really good one. As soon as you said it, I was like, that's me right there. I just felt myself.

That's the entrepreneur credo. That's it, right? Yeah. Like, bloody hell. Okay, last question. What is something that you used to value when you were starting out that you no longer value? Being good at a lot of things. Being good at everything.

I thought I had to be like, you know, not a jack of all trades, a master of all trades. And now I realize that I do not need to be a master of all trades. I realize that I do not need to be a master of all trades. I have to be a master of the thing that it's my like you're icky guy. What do you value? What do you love doing? What are you good at? What does the world get, you know, what does the world go to say like needs? That's something that I didn't know that I had to do. And now I know that I do. And so being a master of one to me as opposed to a jack of all trades. And what's something that you never valued 20 years ago that you really value now? Peace. Clarity of mind. Being able to just.

just do some deep thinking about a really important problem. I don't think I valued that. I think I would have been scared of that 20 years ago. Sitting with my own thoughts. Yeah. Not scared anymore. Not scared anymore. Amazing.

Thank you, my love. Thank you, Emma. If you're loving this podcast, be sure to click follow on your favorite listening platform. While you're there, give us a review and a five-star rating and share an episode you loved with a friend who would be so grateful. Aspire with Emma Greed is presented by Odyssey. your host, Emigreed. Our executive producers are Corrine Gilead Fisher, Derek Brown and me. Our executive producers from Odyssey on Maddie Sprung Kaiser, Leah Reese Dennis, Asha Saluja and Jenna Weiss Berman. Stephen Key is our senior producer, sound design and engineering by Bill Shultz.

Angela Paluso is our Booker, Original Music by Charles Black, video production by Evan Cox, Kurt Courtney, Andrew Steele, Carlos Delgado and Arnie Agassi. by Olivia Holman. Special thanks to Brittany Smith, Sydney Ford, my team's at the lead company and WME. Moora Curran, Josephina Francis, Hillary Schuff, Eric Donnelly, Kate Hutchinson Rose, Tim Mekyll, Sean Cherry and Lauren Vieira. If you have questions for me, you can DM me at Aspire with Emmer Greed. Greed is spelled G-R-E-D-E, that's AspI-I-R-E with Emma Greed. Or you can submit a question to me on my website emma greed.me. Success isn't just about what you achieve, it's about how you achieve it.

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