How to Win in the Golden Age of Entrepreneurship

23:23So one of the other things I think is, and you 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 a hundred 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 pick up your smartphone and say, hey, Harley here. I'm thinking about making a pair of, I don't know, sneakers.

23:53I'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.

24:32That was impossible 10 years ago. Yes. And this idea of starting with an audience, cultivating the audience, and then building a product around something 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're all, we all have these little media companies in our pockets. And you know, 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 in 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.

25:13You 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 find success?

25:41I think you can. I think what you probably have to do then is you have to find your counterpart. You have to find the yin to your 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, who I know really well, MET's amazing. My all-time favorite 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?

26:15They'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.

26:53When it comes to makeup, what's in the formula matters just as much as how it looks. That's why I use Merit Beauty. I've been using their essentials for a while now. And what I love most is how quick and effortless they make my routine. I'm not someone who wants to spend an hour getting ready. Merit keeps it simple, clean, and effective. Their flush balm is one of my go-tos. It gives that healthy, natural glow. And fun fact, one was sold every 30 seconds this year. Then there's The Minimalist, which works as both foundation and concealer, so I don't need to layer up on a bunch of products. I also love everything with SPF, and the Tinted Mineral Sunscreen, which comes in 15 shades, is a game changer.

27:35It instantly dehydrates and leaves my skin protected. Oh, and they have the best brushes too. It's time for beauty that actually fits your routine. And that's exactly what Merit delivers. Right now, Merit Beauty is offering our listeners their signature makeup bag with your first order at MeritBeauty.com. That's M-E-R-I-T Beauty.com to get your free signature makeup bag with your first order. MeritBeauty.com. Calling all sourdough tamers, souffle whisperers and jammy egg savants. Whether you're a professional chef or Jeff whipping up something delicious on the weeknight, there's one brand that can truly up-level your kitchen style and functionality.

28:17Hedley & Bennett. They make premium kitchen gear that combines style, durability and function. We're talking everything from aprons to super sharp Japanese steel knives. In fact, they've sold over a million aprons. You've probably seen their gear on some of the best chefs in the world, in your favorite restaurants and even on TV cooking shows. Every product is designed by chefs for chefs using the highest quality materials and they come with a lifetime guarantee. So, you know, you're investing in quality that lasts. And if you're hunting for the perfect holiday gift, Hedley & Bennett has you covered with collaborations featuring the NFL, One Piece, Bob's Burgers, Disney and dozens of other iconic brands.

29:01There's truly something for every cook. Ready to upgrade your kitchen? Head over to headleyandbennett.com and use code PODCAST15 at checkout for 15 % off your order. That's PODCAST15 for 15 % off. Elevate your cooking experience with Headley and Bennett today.

29:25You 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 the right staff and the right people to come and join you 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, right?

29:51That 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 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 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 - I might but I'm not butchering this, but they said something, you created size 15 of one of your products.

30:32And 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 his clothes every day, is James Burse. James is a great guy. Graham's a great brand.

31:08He's just 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 in 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.

31:37The second thing is I heard this great quote from Bill Gates, which is something like between the ages, 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. None of them succeeded. I was in high school. I was a kid and I was a poor 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.

32:10Honestly, every single person needs to pause and figure out what they were doing in those three years. And just ask yourself that. Yes. Just write it down. That 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.

32:43Yes. 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, on fashion. And I see that across so many of our stores. I mean, I have to tell you, that is so true.

33:14And 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 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. You should do that and put it out online. and it's so interesting. And that's what it becomes. You know, it was 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.

33:48Another 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't enter 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 called the Shopify retail space. And it's a blank canvas. Any Shopify merchant can use it. They do, we do pop-ups all the time for the last three years. And we've had Mr. Beast came in, did a Feastables pop-up. Rihanna did a Fenty pop-up. Eminem did a Mom's Spaghetti pop-up. We've had New Balance in. We've had some of the biggest companies on the planet do it.

34:22And 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 ask all these times and you know, if it's a really big pop-up like a fenty for example It's usually around six 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 like 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 shop We have all these huge companies on shop.

34:59Must have been one of these big ones. 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. Paige 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 Dairy 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.

35:36So 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 the fact that someone unknown to me was the person that has had the highest trafficked, you know, 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.

36:16I'm like, I have no idea what 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. We won't get in the queues. To me, it's just, it's so wild. And the brand that we're going to be talking about in three years from now, they've not been created yet.

36:54Someone watching this right now, I'm not joking, will create the brand that you and I will be talking about in 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 is the best time in the history of the world to start a business.

37:21Oh, 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 isn't, 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?

37:54Like they're very entrepreneurial and maybe they're working in 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 have this great friend, I don't mean to be name droppy, 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.

38:25Funny, Ken was the son. And Hot Wheels was the other product. So they had two products. And they've done amazingly 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 almost like Supreme drops, you know, these like super hot drops were coming out and they did the Barbie movie. And, and, and all of a sudden like Uno is hot. Like what's going on? So hot in my house. And I would ask my house too. And I'd ask Richard, I was like, what's going on here?

38:55And he's like, because people are always thinking that there is only one way to do it. And rather the way that him and Yanon is, you know, Mattel thought about 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 almost rebrand or it's almost like a refounding event of these things, amazing things can happen. Another brand on Shopify is Birkenstocks. Birkenstocks, I think, was created in 1775. Birkenstocks is not only a cool brand now, they're hot again.

39:32How 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 1919. I know my retail history quite well. I studied this stuff. You really do. It's impressive.

40:04Hunter Douglas is still one of the most important home furnishing brands on the planet. And they're literally a hundred 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, you end up with these icons. I've read this beautiful thing.

40:41And I think you're absolutely right in what you're saying. I once read something that Bernard Arnault 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 of what's coming and be willing to change. That's right. Right? And it's just like, you see that with the best celebrities.

41:13You 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 thing. It's just a different lens on the same thing. Yeah. 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 Hunter Douglas, a hundred years later, who are still dominant because they're like they're not talking about what they were talking about 20 years ago.

41:53They're talking about augmented reality. They're talking about virtual reality. They're talking about agentic 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 of scale, you think about losing the soul, right?

42:22That 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. Cat's one of my favorite entrepreneurs. This is public information. AG1 basically has done$600 million with one single SKU. They have one SKU doing$600 million. Honestly, I think I'm like a million dollars of that. That product is - It's amazing. I love AG1 too. It's so good. So AG1. Is it a one SKU company? It's a one SKU company until last week. I don't know. Okay. So one SKU, 600 million.

42:59What's the new SKU? Sorry, we're here now. They have a couple of 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 SKU, 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.

43:29Back to our friend Ben at Gymshark. 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. Or, you know, Ronnie Kith. When you walk into a Kith, every Kith store feels the same.

44:02The 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 kids a Kith ice cream. I'm like, guys, can we just go there for ice cream? No, because they believe like that. But it feels authentic. Yes, it really does. Because they understand it. 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 partnered with Seidel's instead. And that's the Kith restaurant.

44:30So there is this way to scale that stays authentic. But the brands that try to be everything to everyone, that's usually where they die. Forget about it. 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. I think 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 to zero as it's ever been.

44:59I think it's really important just to stop you there because I don't think people understand this, but most businesses fail. That means you have to expect for everything not to turn out. And we do a disservice. I mean, I 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 glamorous or 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.

45:33It'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 tool. So where they fail is they believe it's going to be glamorous. They see the highlight reel 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 love it, there's nothing like it.

46:12So 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.

46:46If you think you can cruise, you know, I got a chance to meet Mr. Beast and Jimmy and that whole team. And you look at festivals and it's incredible, obviously, this is a company that's now rivaling Hershey's, right? And you think, well, Mr. Beast has it so easy because, you know, he has this, no way. this guy, first of all, they're all held up in North Carolina in this 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's going to be easy, it's probably not for you.

47:21But 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.

47:41When we started Skims, our goal was simple, create underwear and intimates that actually work to create solutions for women. Too often, bras are uncomfortable, underwear doesn't fit right, and nothing feels effortless. We wanted to change that. And I can honestly say, seeing skims in the hands of people who feel confident and comfortable every day has been incredible. One of my personal favorites is our Fits Everybody t-shirt bra. I wear it every day. The design came from hours of listening to feedback, testing fabrics, and making sure it was something you could wear all day and feel amazing. And for anyone who asks me for recommendations, I always point them to our soft lounge pajamas.

48:19All my friends and family live in theirs. Shop my favorite pieces at skims.com and after you place your order be sure to let them know that I sent you. Select podcasts in the survey and make sure you go in the drop down menu that follows. If you're looking for the perfect gifts for everyone on your list the Skims Holiday Shop is now open at skims.com. These days it's easy to feel drained, stressed and out of balance but that's where Symbiotica comes in. Their supplements are designed to help the body perform at its best, naturally and effectively. Symbiotica's formulas combine science and so importantly, clean ingredients to support everything from focus and energy to glowing skin and better sleep.

49:01For example, the Shilajit Liquid Complex flavoured hazelnut cacao helps improve cognitive function, boost cellular energy and balance your hormones. Their luposomal glutathione in citrus berry flavour, which is quite possibly my favourite supplement, promotes glowing skin, gut health, and healthy aging, thanks to faster nutrient absorption through luposomal delivery. And magnesium L3N8 with a smooth vanilla cream flavor, that supports your focus, calm, and restful sleep, which we all need. Every product is carefully crafted with bioavailable nutrients, and the convenience of their monthly delivery makes staying consistent so easy.

49:40For anyone looking to elevate their daily wellness routine, like me, Symbiotica offers a simple, effective way to start feeling better from the inside out. Go to symbiotica.com forward slash aspire for 20 % off plus free shipping. That's symbiotica.com forward slash aspire for 20 % off plus free shipping. Rent is one of those things we all do, but let's be honest, it can feel like a total drain. I remember when I was renting, counting down the days until payday just to hand most of it over. That's why I love Built. Built is the loyalty program for renters that rewards you for your biggest monthly expense, rent.

50:19Each payment earns points that you can redeem towards flights, hotels, lift rides, amazon.com purchases, and even fitness classes like SoulCycle, Barry's, or CorePower. And it doesn't stop there. Paying rent through Built also unlocks perks from more than 45 ,000 merchants. Link your credit cards, shop at your favorite local spots, earn points on top of your usual rewards and get one step closer to something you actually want. Personally, I'd redeem mine towards, I don't know, a little trip somewhere fabulous, maybe a work trip, maybe a workout class, or, you know, a little credit. Finally, paying rent can feel like it's giving something back instead of just taking.

50:59Join the loyalty program for renters at joinbill.com slash emma. That's j-o-i-n-b-i-l-t dot com slash emma. Make sure to use our link so they know we sent you.

51:16One 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, you know, 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 failed miserably, have failed big, have failed multiple times.

51:49And 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 of 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 phases 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.

52:20I 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 Shopify 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 amount of value, and that Shopify 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.

53:02So it's easy for me to do so. But I was very hard on myself in the early days of like, you know, I was COO for six or seven years of Shopify. And I think I was an okay COO. 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 realized that no one is good at everything.

53:44And 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, for me is 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 them mentors.

54:18It 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 an, 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, he's bad at being married. You're like, show me the money. No, he's bad at being married. When I, when we had our first, my wife and I had our first child Bailey nine years ago, I looked around and I was like, who do I think is a really good parent?

54:49I ended up finding someone who just always felt like he was just a great dad. He was there for his kids, understood his kids. And so I was like, you're going to be my parent mentor. And so I found someone who was, but 10 years ago, ShopLite 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 thousands, but 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.

55:27And so I've sort of been doing this, 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 personal board of 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 more time here.

56:02I don't know what I can do for you, but will you spend an hour with me every four weeks, virtually and over coffee, what have you? And I've been running this playbook on this personal 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, my life life and my work life that I had to separate my, my kids and my wife from Shopify. And actually what I realized is for me, this idea of bringing all together harmoniously is incredible.

56:39Having Lindsay 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 and work from Shopify. And I used to want to go there to support the entrepreneurs, but I feel bad about Bailey and Zoe, my daughters, 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 this. Yeah, it's a really cool book. It's really great. I need the book for sure.

57:07It's coming out in a few weeks. But I wrote this book because I felt that most schools are not teaching entrepreneurship. 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 fireman, doctor, lawyer, actor, magician. Like magician's on there, but like entrepreneur's 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 Builder Sunday. My kids love it. And so this idea of incorporating all these elements of my life together has been really amazing.

57:39And 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, just 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 just the one wife, which is so lovely. I love her. She's the best. I'm sure. But you also have a tea brand and what strikes me about you and I did my own homework was how connected 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.

58:20The idea that you were 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. I think it's poison too. Look, a lot of people assume it's because I'm extroverted. I am a power extrovert. I like, it's not about extroversion or introversion. I think it's about energy levels.

58:51I have filled my life. Why do 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, it's a weird flex, but I did an ultra endurance race this weekend called 29-0-29 that Jesse Itzler 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. Yeah. Yeah. It's basically you emulate climbing Mount Everest. No, I'm not exhausted because I fill my life with things that are deeply meaningful to me. I'm not searching for happiness. I'm not searching for some gold star.

59:23I'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, 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 requests. 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.

59:58I 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. 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 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. I had people in my life, sometimes family members who were kind of energy vampires. I'm trying to be my best version of me and meditate and work really hard and be a great dad and husband.

1:00:39And 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.

1:01:13You mentioned the tea company. So during the pandemic, I sort of had felt that I had 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 Tea. And we got to work on it. 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 Tea.

1:01:47So he knows a lot about tea. 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 with Firebelly Tea 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.

1:02:22So 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. And 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 meditation is in the calendar. Walks with Lindsay is in the calendar. I mean, Jesse Itzler 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.

1:02:58First of all, I love Jesse. 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. Yeah. That's it. I mean, I think that's really a big thing for young founders because your energy is all you have. Yeah.

1:03:29Well, Ben called me when Ben Francis called me when he was having, he had twins and he called me when he was, he found out he was having twins. And we talked about this idea of, you know, how do you, how do you run a company like Gymshark and be a good husband and be a good dad to twins? You know, 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 too 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 it.

1:04:04And 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 and then build your own schematic.

1:04:44You know how the holidays can get. of stress. The Sun Goddess Matcha is this soothing, antioxidant-rich tea that helps calm my mind and keep my skin clear and glowing. Then there's BT Fountain, a beauty electrolyte that hydrates from within. It's packed with minerals, ceramides, and hyaluronic acid, and I swear my skin feels softer and more radiant after just a couple of weeks. Plus, it tastes amazing. Bright yuzu and sweet raspberry, it's so easy to make part of my day. While everything else this season feels go, go, go. Peak has helped me slow down and actually feel good in my own skin. Feel the holiday magic and unlock your healthiest glow with the most exciting offer of the season.

1:05:2220 % off site-wide for life. Plus a complimentary exclusive holiday bundle. Go to peaklife.com slash aspire. That's p-i-q-u-e life.com slash aspire. This is hydration redefined. Try it and glow from the inside out. As someone who spends a lot of time talking into a microphone, I've learned the old adage is absolutely true. It isn't just what you say, it's how you say it. To truly make an impact, you need to set an example, take the lead and adapt to whatever comes your way. And when you're that driven, you need to drive something equally determined, the Range Rover Sport. The Range Rover Sport is designed to make an impact, blending pure power, poise and performance.

1:06:07The design is distinctly British with the capability to take on roads anywhere. Free from unnecessary details, the Range Rover Sport lets its raw power and agility shine, delivering a truly instinctive drive. Its assertive stance hits an equally refined performance. This is true modern luxury. The latest innovations provide new levels of quality, comfort, and control. You'll feel it with the cabin air purification system and active noise cancellation. And when the roads get challenging, Terrain Response Tune fine-tunes the vehicle with seven different terrain modes. This force is powerful inside and out, created with a choice of engines, including plug-in hybrid with an estimated range of 53 miles.

1:06:50Like you, the Range Rover Sport was designed to lead. It combines that dynamic sporting personality with elegance and agility in a way that truly sets it apart. Explore Range Rover Sport at rangerover.com slash US slash sport. That's rangerover.com slash US slash sport. You know that feeling when the holiday rush finally quiets down, the lights are twinkling, the coffee's warm, and you just get to be for a moment. That's the feeling I try to hold on to all season long. For me, it's about those little luxuries, soft slippers, good music, and lately, my favorite cashmere sweater from Macy's. Macy's has been perfecting cashmere for over half a century, and you can feel that experience in every piece.

1:07:34Their collection has over 70 silhouettes and 40 plus colors. So whether you love bold tones, soft pastels, or cozy neutrals, you'll find something that feels perfectly you. And right now, it's the best time to treat yourself. Macy's friends and family event is happening through December the 11th with 30 % off the best brands that make the best gifts, plus 15 % off beauty and fragrances. There's also 30 to 50 % off jewelry from brands like Effie and Levine. And the perfect way to add a little sparkle to your cashmere look, head to Macy's today to bring a little everyday luxury into your holiday season.

1:08:14What 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 distracted. 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 have 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 exercise, like meditation.

1:08:51It'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 a proud Jewish entrepreneur. We do Shabbat dinner with family. And I do a Shabbat message, Shabbat shalom message to the whole world on social media with my family, because it's just, we're just, we want, I want want to wish everyone, we say, it's very simple. We hope you had a great week. We hope you have a great weekend.

1:09:20Shabbat 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. I think rituals really, really matter. 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.

1:09:56I'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 fit. You know, for me, it would be like, even just like having a cup of tea in the morning, like 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.

1:10:36And I'm like, no, they give you time. They give you energy. I had this great interview with Andrew Ross Sorkin interviewed Jeff Bezos recently. And I just stumbled upon it. Oh, the deal book interview. It was so good. And so 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 just, I think he said, I just putz around in the morning. Yeah. Just saunter around till about 930. I was like, what am I doing? And I was like, whoa. He's like, you know, I check my phone. I read newspapers. I have coffee. breakfast.

1:11:09I hang out with Lauren. He sees his wife. I loved him saying that because it gave me permission. It gave a lot of people permission to be like, you know what? In the morning, I also like to putz around. 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 want to be able to do this for a very long time. If Shopify will allow me to be their president, I'd like to do this. 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.

1:11:41Yes. 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%. And to requalify means that 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 of Shopify should be the best person in the world, like should be in that spot.

1:12:27And I like the pressure and the growth that insinuates that I must have in order for me to requalify. I also believe that I have to requalify to be Lindsay's husband every year. And I have to requalify 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 got to get better at this stuff. I got to be a better dad. I got to be a better president of Shopify. I got to be a better husband. And it motivates me to always think about how to be constantly improving.

1:13:06That 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 requalifying to be the best dad and the best husband, as well as being the best president at Shopify, what does that actually look like? 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.

1:13:39And 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 with 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 something going to the office, she is understanding.

1:14:13She'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 of 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, and, and a six-year-old consulting with a six-year-old is, is, I mean, you get a lot of fluff. You also get some really beautiful things. And I'm telling you the kids will tell you the truth.

1:14:41They'll tell you the truth. They're not trying to spare my ego or my self-esteem. 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. And I'm like, all right, you're right. Like you, 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 laptop. I'm like, look, we're doing this together. But we're all together. At Shopify, it's a little bit different. At Shopify, I'm actually able to. So back to earnings, for example, I watch a lot of tape.

1:15:08Meaning 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 nuanced metric. Oh, 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.

1:15:40So at Shopify, it's not necessarily completely objective, but in my role, I'm like, okay, who's doing this really well? Yeah. And there's 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 on myself. No, you're in a constant cycle of improvement.

1:16:16That's it. That's just who you are. And that creates a lot of meaning. You see, 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 to 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? 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.

1:16:50That's what I want for myself. What do you say to those people? So Shopify has about 8 ,000 people at the company now. That's a lot of people. That's a lot of re-qualification happening there. On a weekly basis, I constantly find someone in the organization, not even on a team, like somewhere in the organization. I might even, like, 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.

1:17:26And 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 so creative. And so if you're listening to this and you're an organization and you want to, you know, you want to find your own pathway 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.

1:18:04That'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 and a different team, I'm like, look, I'm going to like take you and bring you in here. And you're, we're gonna do this really cool thing together. You know, the person that, 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 milestone 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.

1:18:40And 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'd be excellent at that. And you go above and beyond. It's so seldom that people don't do that. Most people, if you're working at Shopify, if 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.

1:19:17So I get that it's really difficult if you're in 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 I, 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 has to come from you.

1:19:54So 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 requalifying for the patronage of your customers, of your consumers. 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, it goes back to the beginning.

1:20:31Yeah, you hear consumers say, oh, I love that company, but they've lost their way or lost their soul. They got acquired by some big company or something. The reason that some companies, when they get acquired by some bigger company, stop hitting the mark is often because they're part of a larger organization where 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.

1:21:04Do 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 is a lot. It's a lot. And then 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 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.

1:21:33They'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 where I have what I, there are some Saturdays where I have to work and there are some Thursday afternoons that I go for a walk with my wife. That's my version of harmony. It's a really, 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 interesting. And I always think about so many successful people I know have concerns about their kids.

1:22:05They think, you know, it's like how my kid's 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 - Are you out there trying to kind of like manufacture hardships for them? No, I'm not. So actually in truth, I'm really glad you brought that up. I think manufacturing scarcity is silly. I'm not going to pretend that we are poor immigrants the way my father was. However, and my wife is much smarter than me and psychotherapist and incredible woman.

1:22:41She'll often say, she's like, look, they weren't there pre-IPO. They don't remember the hardship and the tough days of Shopify. They don't remember 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.

1:23:15I didn't grow 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 do everything 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.

1:23:51I'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 of publishers said no. I told them about that. They're like, well, 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.

1:24:26I want them to have some grit. I want them to feel like they themselves, 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 that's a really great lesson for kids, for them to understand the journey. And I always think about, because I leave the house every day and ultimately 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.

1:25:02They 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. 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 her family.

1:25:31There's a great deal of care. I actually think that's really what it's about. In the week before earnings, for example, my daughters will come into my home office and they'll see like papers everywhere. It's late at night. They're like, what are you doing? I'm like, I'm studying. And then they'll see me on TV the next day or a week later. And they'll be like, dad, you're so great. I was like, why did I do great? And they're like, because you studied. I was like, exactly. I want them to see, you know, the work, like the actual journey and the destination. And I think a lot of successful people only show the destination and they don't necessarily leave enough breadcrumbs for their kids.

1:26:04I 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.

1:26:37in 2024 since like 2004. So more people - Trying to name the company now. That's right. Yeah, that's right. But more people are trying their hand on 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 for my father and for my grandparents, My grandmother was also an entrepreneur. My grandfather sold eggs at a farmer's market most of his life. For them, entrepreneurship 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.

1:27:13Please do something safe with this education we've given you. 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.

1:27:46If 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.

1:28:25But if you combine all these things, you know, it used to be that the incumbents, so basically the established companies were impossible to disrupt. Yeah. 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 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.

1:29:05There's no way a big company can 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 too. 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. Oh, I love it. That's just the most beautiful way that you could end this conversation.

1:29:39It'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 like constantly being in motion and becoming, it's like a gorgeous conversation. Thank you. It is a great honor to be on the 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 entrepreneurship is.

1:30:16You don't learn entrepreneurship anymore at HBS. You learn it on shows like this and you learn it from 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. And that's just 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.

1:30:45We'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 business 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. Shopify store. First of all, I am buying that.

1:31:18Oh, it's amazing. I'm buying it immediately. I hate cold coffee. I can't bear a cold tea. Ember. 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 basis of compound interest.

1:31:55The rule is 72. 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, Poor Dad was a really great one. 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 of 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 if I drop it and it doesn't break, it's robust. But Nassim Taleb introduces a third system called Anti-Fragile, that some things, when you drop it, actually reassembles stronger than it was in the first place.

1:32:31The 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 know, it's just back to that of a requalification that like sometimes when you're going through the stuff and you, 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.

1:33:03That'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 have to be a master of the thing that it's like your icky guy. What do you value? What do you love doing? What are you good at? What is the world good at? you know, what is the world going to say, like needs.

1:33:35That'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 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. That was scary. Not scared anymore. Not scared anymore. Amazing. Thank you, my love. Thank you, Emma.

1:34:29I'm your host, Emma Greed. Our executive producers are Corinne Gilead-Fisher, Derek Brown, and me. Our executive producers from Odyssey are 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 Peluso is our booker. Original music by Charles Black. Video production by Evan Cox, Kurt Courtney, Andrew Steele, Carlos Delgado and Arnie Agassi. Social media by Olivia Holman. Special thanks to Brittany Smith, Sydney Ford, my teams at The Lead Company and WME. Maura Curran, Josephina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson-Rose, Tim Meikle, Sean Cherry, and Lauren Vieira.

1:35:16If you have questions for me, you can DM me at Aspire with Emma Greed. Greed is spelled G-R-E-D-E. that's Aspire A-S-P-I-R-E with Emma Greed or you can submit a question to me on my website emmagreed.me.

1:35:35Look we get it you can hardly go anywhere or do anything these days without hearing about AI this or AI that and if you're like most people when it comes to AI you're impressed but you have a few concerns. What if AI was used not as a tool to replace people but as a way to help understand people better. AI from SurveyMonkey is designed to do just that. From crafting the perfect survey, which is way harder than you might think, to analysis that digs deep, finds patterns and surfaces trends quickly. SurveyMonkey's powerful suite of AI capabilities makes it faster and easier than ever before to get insight from real people, helping you make confident decisions in your business.

1:36:15Use promo code EMMA for two months free when you sign up for an annual plan at surveymonkey.com slash emma.