← The Rich Roll Podcast
The Rich Roll Podcast
Entrepreneurship Is A Mindset: Shopify President Harley Finkelstein On Why Failure Is The Path To Success
02:13:52
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- [00:01]
A
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B
It is scary to start a business. It is very scary to put yourself out there. It is very scary to fail. The cost of failure in the 50s of entrepreneurship was massive. Today it's not.
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A
Harley Finkelstein is democratizing entrepreneurship for the digital age. As the president of Shopify, Harley has helped transform a small snowboard equipment retailer into a global e commerce giant that now powers over 10% of all online retail in the United States. But Harley is more than just a tech executive. He's a serial entrepreneur who started his first business at 17. He's a lawyer. He's a dragon on CBC's Next Gen Den and a champion for mental health awareness. In the high pressure world of startups.
- [04:04]
B
This imposter syndrome of entrepreneurship, it's only in your own head. True confidence isn't actually knowing what to do. It's knowing that whatever comes your way, you'll be able to figure it out.
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A
Harley embodies the spirit of modern entrepreneurship. He's curious, he's resilient, always innovating. And this is a conversation about all of that. It's about seizing opportunities, embracing challenges, and the transformative power of technology in both business and life.
- [04:32]
B
The people that I speak to that have left the job they didn't like or found success using entrepreneurship, they're pretty damn happy about it.
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A
Do you think that everybody can be an entrepreneur? Great to have you here. So nice to meet you.
- [04:52]
B
Yeah, you as well.
- [04:52]
A
The first thing I wanted to ask you about, I saw this on your Instagram. You recently did the 29029 event, right?
- [04:58]
B
Crazy.
- [04:59]
A
Like five weeks ago or something like that. Which one did you do?
- [05:02]
B
I did Trommela. I think there's two. There's one in Whistler in Canada. This is the second one in Canada.
- [05:06]
A
Are you friends with Mark and Jesse and those guys?
- [05:09]
B
I'm now friends with Mark. I didn't know them before, but I ended up doing a bunch of the, the hikes with Mark. And when you're doing something like that, you sort of bond with the people.
- [05:17]
A
You definitely get to know people.
- [05:18]
B
Well, I knew the concept. I know you sort of had a bit of a turning point when you turned 40. I kind of had a similar thing, which is I was like, I want to start thinking a little bit more about our family motto. In my house with my wife and my kids is my kids are 5 and 8. So I'm not sure they really understand the family motto, but my wife and I's family motto is the way you do anything is the way you do everything. And it's just a proxy for intentionality. And I sort of felt like every aspect of my life, especially my work life with Shopify, was very intentional, but I wasn't necessarily sure that my health side of things were as I was being as intentional. And I heard about the concept of misogi, this idea that do something every year that I think that. I mean, this is my version that scares the shit out of you, but also something that books marked the year. And So I turned 40, and I want to find something. And then I read about this idea of Everesting, which is climbing the equivalent of Mount Everest 29,000ft. And they just happen to have one an hour away from Montreal, where I live. And so I did it. It was awesome.
- [06:15]
A
That's cool, man. That adventure is a little sneaky, right? Because on paper, it's like, how bad can it be? Like, you hike up with your friends and you take the chairlift down. It sounds actually quite pleasant.
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B
Yeah, it's not.
- [06:27]
A
And then inch by inch, it starts to become a thing. Right. And you're like, wow, it's a little bit harder. And what's great about that event is it sounds like you're not coming from an endurance background. You're not running marathons and stuff like that. So it feels very doable. And I think it brings in who haven't done something hard before, because it feels like a nice starting point, but it's actually quite hard. And what's so cool and fulfilling about not just participating, but getting to know the other sort of people that are doing it is seeing those people who've never done anything like this before, but then becoming determined to finish it. And literally, it's like you're into the second day, and you get to decide whether you're gonna go to sleep or not and for how long. And when those people finish, this is way more than doing a 5k or a 10k or very difficult.
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B
It turns out it's like 50k.
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A
Yeah.
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B
Right.
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A
And when they finish, like, it's life changing.
- [07:21]
B
Yeah. You know, although there was a rumor that I heard that you actually finished early, so you did an extra one. Is that. Is that true?
- [07:26]
A
You did your homework? Yeah, no, I don't. I don't talk about that publicly.
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B
So you did an extra.
- [07:30]
A
I get a lot of shit for that.
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B
Which is the most sort of, you know, ambitious type A thing I've ever.
- [07:34]
A
Heard about, that was not the plan. I just was struggling with trying to sleep because when you're doing something hard, it's disruptive to your sleep. And I was just awake, so I was just like, I'm going to get up and do it. And my buddies were like, oh, you snuck out. And like, you know, that was not the case at all. They're much, much better athletes than I.
- [07:51]
B
It's a very subtle flex, but I. But I really loved it. I loved it for a few reasons. One is I love the idea of the training up to it. That because I'd never done a marathon, I'd never done an endurance race, I was scared. And one of the things that 29 does really well is you do these sort of these like, zoom calls with coaches. And so I got a chance to meet the coaches and one of the zoom calls, they're like, write down what you're most scared of as it relates to the race. And I only had one thing written down. And this is, you know, I'll be vulnerable here. I wrote down, I'm scared of not completing because of being embarrassed. And so next call, they're like, take that one thing you're scared of and break it down where I was like, okay, who am I embarrassed? And honestly, I did it with a group of guys, we all trained together. And it was. I didn't want to fail because I didn't want to be the guy in the group that didn't complete it. That if I'm so intentional about every aspect of my life, I gotta finish this thing. And so actually our little group text was dead or done that. Like, no matter what, come hell or high water, word completed. What I did not anticipate is the mental exhaustion of being up for 36 hours straight. And you hear these stories about, you know, after hour 26, you're gonna start hallucinating. And I was like, there's no way I'm gonna be fine. And at hour 26 or so, I went to go take a 60 minute nap because I just. My brain was mushy. You can sort of feel those proverbial demons coming out saying, well, you already did 10. I think the 10 was the equivalent of Kilimanjaro. So I'd already climbed the equivalent of Kilimanjaro. Do I really have to do Everest?
- [09:25]
A
You start making those deals, you start.
- [09:26]
B
Making those deals with yourself or deals with the devil, as they say. And so I took a 90 minute nap, came back, finished it. It's this wonderful experience that you cross the line with your red hat with the guys you've been training with, and it was awesome.
- [09:40]
A
How many guys did you do it with?
- [09:42]
B
We were four total. Yeah. Me plus three.
- [09:44]
A
And in those zoom calls with the coaches, was one of those coaches Chris Hout?
- [09:47]
B
Definitely, yeah.
- [09:48]
A
So when I was 40, he was my guy. Like, he's been my coach from day one through all my endurance challenges. Yeah. So Chris now works closely with Jesse on a number of things, but back in the day, when we first started working together, he was purely like, an Ironman triathlon coach and an ultra endurance coach. And he's the one who kind of shepherded me through, like, everything that I did back in the day.
- [10:14]
B
They're amazing. And the other thing I think was, for me, at least, what was remarkable is that it was one of the first times in my life that I really felt like I did not check my phone, I did not check my email. I was fully focused on this one specific task. And I try to be a bit of a master multitasker in general in my life. There's just no way to do multiple things when you're doing something really, really difficult. And I would do it again for no other reason than simply to have a singular focus for an extended period of time. And across the finish line, my wife and my daughters were waiting for me, and I just, like, welled up and started to cry. And I don't even know why I was starting to cry. It was hard, but wasn't that emotional for most of it. And I think this idea of doing something that scares you becomes less and less common as you get older. This idea of, like, comfort zone stuff kind of creeps in. And I actually think, like, what I've learned from it is, like, this idea of getting really comfortable with being uncomfortable. I'd like that to be my operating model, if I can, for the next 40 years.
- [11:18]
A
Well, Msogi box checked. Yes. I think the interesting kind of ripple in the whole, like, comfort zone out of your comfort zone thing, particularly with high performers like yourself, is that being a public person, you're sort of celebrated as somebody who has prevailed in the game of being outside of your comfort zone. And that celebration can actually keep you stuck. Because what people don't understand is that thing that appears to be so uncomfortable for so many people is your comfort zone. Right. You know what I mean? Like, the hard thing that everyone's so scared of that you've spent many years mastering. Everybody thinks that you're way out. Your comfort zone, but that actually becomes your comfort zone. And then you have to exert a lot more kind of effort to figure out how you're going to step outside of that. And you're so used to being celebrated in this one area that for you to say the embarrassment thing, I get that because you're seen as a successful person. So what does it mean if you fail in this other thing? As somebody who also talks a lot about failure and embracing failure and all.
- [12:26]
B
Of that, and I don't have to do it. I can just sort of. I can cruise from this point. Right. And I don't want to cruise. I actually think that ultimately that sort of family motto of how you do anything is how you do everything is about not cruising. I say it's about intentionality. And my wife and I try to put the same thought into, like, making, like, a dinner, like, on a Sunday night for our kids as we do by planning a trip, as I do by preparing for an earnings call for a quarter end.
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A
It feels like a lot of pressure, though, too, especially for little kids.
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B
There's an intensity.
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A
You're inculcating them with that, for sure.
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B
And not just that. Now am I actually focused on spending time on perfecting some version of a meal for my children? And that's actually where the balance comes in, is that I want to make the best pancakes. But if I spend all my time thinking about the greens of the pancakes and less time about sitting with my kids while they enjoy it, I didn't really win this thing. In fact, I lost this thing. But it's tough to sort of turn off this, whatever the alpha energy is, the type A energy is, and say this. Actually, what matters here is spending time with my children, not making the greatest pancakes on the planet.
- [13:26]
A
And how are you doing with that?
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B
Not very well.
- [13:28]
A
Yeah, not well. I heard you talk about that a little bit with Stephen Bartlett. Like your ambition to be a great dad and being honest about where you might have some room to grow in that area. I don't know when you recorded that, but it wasn't yesterday.
- [13:45]
B
No, it was a while ago. I think I've made some progress. I think what I have realized is that this idea of mentorship, which is something I know you talk a lot about on your show, I don't think you can carbon copy any one particular mentor. I think you need mentors across different verticals. And I don't necessarily think I've surrounded myself historically with people that were the best parenting mentors in my life. I didn't gravitate to them. The way I gravitated towards business mentors, successful people from a commercial perspective. And part of it is that you can quantify business success, money, market, cap size, growth, whatever metric you want to use. It's very difficult to figure out who is a really great father and then say, actually, I'd like to learn from that person. Paradoxically, almost, it's way easier for me to find mentors in business than I can find mentors for parenting, Even though parenting is probably where I need the most amount of help right now.
- [14:45]
A
Interesting. Yeah. I mean, I've had people on this show who will look me in the eye and say, I know I'm a great dad. And I've thought the same thing, like, how do you measure that? But there is a knowingness for those individuals because that's where their energy is. Right. And for somebody who has a lot of responsibility in the real world, in the business world, like you do, for me, it conjures up a conversation around balance and this idea of. Of pursuing not necessarily greatness, but, like, trying to be a master of your craft and the idea that you can be great at several things, but perhaps not at the same time. Right. And when you have important values in your life that come into conflict in terms of your bandwidth and ability to attend to them, that's a very real problem. So how do you manage that knowing, like, hey, you know, my marriage, my family life, super important, what I do with Shopify and the impact that I'm having in the world and my philanthropy and all of these things are all very important, but it's a little bit like whack a mole. Right. So how do you make sure that everybody's attended to in the manner in which you want to make sure that they are?
- [16:00]
B
When I was younger, I'm not really a big video game guy now, but I used to play video games when I was a kid. And one of the video games I loved was Street Fighter. And one of the things I always thought was funny about Street Fighter, fun about Street Fighter, was prior to starting the game, you picked your character. And if you played Street Fighter, you'll sort of visualize a character screen, and each character you sort of see different levels. So, like, defense, offense, jump, whatever, kicking, punching. But no character had everything, right. Like, if they were really good at jumping, they were really bad at, like, punching or something like that. Based on my skillset in playing this video game, I would select the character that was the most appropriately designed for what I was good at. The video game I think about it a little bit like that, where I don't think I can be great at everything. Not that I even try to do so. So I try to pick the things that, like, really matter to me. Shopify is not a job for me. It is very much my life's work. We can get into a little bit about what that means to me because I think the concept of life's work is a very contemporary term. I don't think my grandparents or my parents even ever use that term because for them, employment was a means to put food on the table. And this idea of actually having a personal Venn diagram overlap with a professional Venn diagram, like your personal interests and your professional interests are kind of the same thing. That's what Shopify is for me. So it's a very much, for better or for worse, a very personal pursuit as much as it is a large company. So that's important. And I've. I think the second you raise money, you take your company public, you're basically committing that this is gonna be your main quest. So I try not to have any side quests. So that's a main quest. Lindsey, my wife, and my daughters, Bailey and Zoe, they're a main quest. And I probably have a little bit of room for some sort of hobby type thing, but that's kind of it. That means that I can't join a recreational, I don't know, tennis league. It means I can't take the trips that my friends take summertimes where they go off to Europe and, you know, gallivant for the summer. Sometimes it feels like if I'm working this hard, shouldn't I be able to do all those things? Also, I feel the responsibility of the 8,000 people that work at Shopify, the millions of stores that use Shopify. I feel that every single day in a very positive way. But that drives me. But that also requires me to say these other things. I'm sorry, I just cannot do them.
- [18:18]
A
How do you square that with also understanding that widening your aperture to the world actually makes you better at. As the steward of Shopify. Like, I know that you're somebody who understands and appreciates the importance of how unlikely influences can impact your entrepreneurship skills. Like the obvious example, of course, Steve Jobs, understanding design and Eastern philosophy and all of these things contributing to what made him so compelling and unique. And I'm reminded of David Epstein's book range, the idea that. That having a confluence of interests and influences can actually make you uniquely suited to your job and better than you might Imagine with, on the other hand, the idea of blinders on focused, getting the job done, all of that. You can't be a Renaissance man and be the president of Shopify, but you also understand, hey, it might be good if I read some books and meet some interesting people that are outside of my field to become not just a well rounded person, but actually better at my job.
- [19:27]
B
I pick selectively so I wish I can have more of those inputs from different areas of the world in which I can synthesize and then use it to do my job better. But I can't do it all. So I'm selective about it. I'll give you a good example. During the pandemic, I felt that I had a pretty good sense of Shopify's product at an enterprise broad level. But for a brand new business starting on Shopify. I built a store on Shopify as one of the first merchants, 2006 or so. So 2020 or 2021. It had been, you know, it had been 14 years since I started a brand new store on Shopify. And I felt that I may have been somewhat out of touch in terms of what are some of the trials and tribulations of a brand new entrepreneur getting their first sale on Shopify. So I wanted to, I wanted to start a brand new store. At the same time I have anxiety. I've had anxiety most of my life. I was switching away from coffee and spending more time drinking, looking for good tea. My best friend serendipitously is a guy named David Siegel, who's the founder of David's Tea, built probably the only billion dollar tea company on the planet, took it public same year as Shopify. And so David was sort of giving me really good tea to try because I was getting off coffee. And at the same time I also want to experiment with Shopify. And so we built a tea company called Firebelly Tea.com I've learned more about Shopify's product being sort of a silent partner in Fire Belly Tea than I have being on the road 300 days a year talking about Shopify's product, talking about Shopify's business. That to me was the perfect example of that feels like a hobby because I get to literally I had to register a domain name. I had to figure out Google AdWords. I had to sign up.
- [21:08]
A
You're doing the same thing every soccer mom has to do.
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B
Precisely.
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A
Every photographer, product, photography, right?
- [21:14]
B
Like should I take overhead or should I do a 360? Should I use this new augmented reality application? Should I use AI to write a product description. Should I write it myself? So where I can find something that is going to make my role leading Shopify more valuable and at the same time, I can pull from something unique that is outside of my normal day to day. That's the ideal situation. I actually think 29029 was also like that because what I realized is it was a good reminder that we're about to celebrate our 10 year anniversary since the IPO. So we've done. I've done 38 earnings calls. 39 will be coming up in November and then the 40th will be in early 2025. At a particular point when you do something for 40 times, you begin to get into a rhythm. And often that rhythm allows you to not go on autopilot, but you begin to kind of like you get some swagger to the whole thing. On the drive home from the Everesting race, I remember thinking to myself, like, how can I do that? Totally different. I don't want to get caught in this routine of any of my daily activities at Shopify. Now again, it's sort of a bit of a cognitive dissonance mindfuck that this climbing mountain has brought me to a point where I'm now thinking about doing my job differently at Shopify. But it did because it was a reminder that I can do things that are outside my comfort zone, that I can get good pretty quickly, that I can be. I don't have to get into a routine. And I think we as humans, when we get into the routine, it feels really good. We have swagger, we have confidence, and we like to kind of stay there. And I think you need someone or something to kind of pull you into that next box. And at the bottom of the next box, you're going to feel insecure. You're going to feel out of touch. And so now with my team, I'm trying to figure out how do we actually rethink the way we do earnings calls, which you can sort of debate whether there's real value in redoing it. Like, you know, if it, if it ain't broke, why fix it? Actually, I think there is a way for us to do earnings calls much better. Who's the demographic listening to it? What information are they looking for? Are we making it as easy as possible? And you will see me try to implement new tactics on subsequent earnings calls that are different than what I did in the past because of what I learned in this Everesting race that I think is very positive. What I don't think I can do. And this is sort of where, to use your term, the enough thing comes in is I don't think I can go and spend four weeks on safari right now. It's just maybe at some point I can. I feel a deep responsibility to this business and to the people that have given me this opportunity to not flake for four weeks, even if it's going to bring me back very interesting new ideas.
- [24:00]
A
Sure. Well, let's go back to the beginning. I think of you as a born entrepreneur. I mean, this started quite early for you. So walk us through the childhood and your first flirtation with entrepreneurship.
- [24:15]
B
Thirteen years old, Jewish kid, goes to a lot of bar mitzvahs. Almost every weekend there's some other bar mitzvah or bat mitzvah. And I see at all These parties, these DJs that are performing, and I think they're like magicians, you know, minute one, you have 300 people sitting down in some banquet hall or some hotel or some temple eating chicken dinner. And 30 seconds later, a minute later, you have a conga line happening with people's ties around their heads and light shows. And I just. I thought these DJs were these incredible magicians. And so I really wanted to be a dj. I called around, tried to get a job as a DJ when I was 13. Nobody would hire me. So my dad, and this has been sort of a theme with my parents throughout my life, they didn't have a lot of money, but they've always sort of gave me this confidence, this chutzpah to, like, just try stuff. So my dad sort of suggested, hey, if no one's gonna hire you to be a dj, why don't you start your own DJ company and hire yourself? And while he didn't give me capital or DJ equipment, he made me a business card. And it said, harley Finkelstein, dj. I actually still have the business card in my home office today. And I started a DJ company. And initially I didn't make any money because I was like 13 years old, didn't know how to DJ. But eventually I got pretty good at this thing. And I DJed about 500 parties between the ages of 13 and 19 years old. Mostly bar mitzvahs, weddings, that type of thing, private events. By the time I was in college, I realized that whatever I did, entrepreneurship was gonna be a big part of my life. By the end. I didn't actually care so much about the DJing craft, the music, the mixing, the lighting. I just like the idea that I was able to create Something for myself. And I was able to make money from it. I was able to employ friends through it. It was just this really cool tool in a tool belt. But where things really got serious for me from an entrepreneurship perspective was we moved to South Florida when I was a kid and I went to. So after high school, I moved back to Canada to go to McGill University to go to college. And my dad got into some trouble, and my dad ended up getting arrested. White collar crimes. And I was basically given this ultimatum, which was either I moved back down to South Florida with my mom and two much younger sisters, or I stay in Montreal. And I decided that I would try to use this tool, take it out of my tool belt again, called entrepreneurship, to solve this new problem. The DJ problem was one of passion. I wanted to do this craft, and no one would allow me to do it. So I used entrepreneurship to solve that problem. This next problem was I had to make real money. I have too much younger sisters. My mom needed help financially. My dad wasn't around. I ended up selling T shirts to universities across Canada. It was a real business. I made real money. I was able to help my sisters go to private school. I was able to help my mom with rent. And so entrepreneurship started as this interesting thing that was very much focused on craft and excitement and passion. And it migrated into this tool that would help me solve a problem.
- [27:30]
A
In this case, it was survival practice.
- [27:33]
B
That's right.
- [27:33]
A
Right. Like you learned what you learned when you were younger and when in your moment of. Of need, you realize you could figure your way forward through this experience that you had had previously.
- [27:44]
B
That's exactly right. And not just that, but it was. It's not a perfect meritocracy, but it was the closest thing I could find to a meritocracy, which I needed because I didn't have family connections, I didn't have a bunch of money, I didn't have resources that would give me some sort of unfair advantage. You know, there was no alpha that I had at this particular time. And I ran this T shirt business all throughout college. And we sold promotional T shirts to universities across Canada. And again, I wasn't necessarily passionate about T shirts. I wear a black T shirt almost every day now. But, I mean, I like T shirts, but it wasn't my calling, was my life's work. But this idea of using entrepreneurship to solve the problem became very real for me. And then a mentor of mine convinced me to go to law school, not to become a lawyer, but to become a better entrepreneur. His hypothesis which he was right about was this T shirt business has no unfair advantage. You have no moat around your business. This thing is cool right now. When you're 19 years old or 20 years old, this is not going to be truly something that is worthy of your life. And he's like, but if you're not sure what it is, why don't you consider entrepreneurship finishing school? And this particular mentor happened to be teaching law at the University of Ottawa, which is the capital of Canada. And he's like, why don't you apply to University of Ottawa? I'm teaching here. You'll go to school here. You'll know at least one person in town. And that brought me to Ottawa. And within a few weeks of moving to Ottawa, I met this brilliant programmer who just moved from Germany to Canada. He moved to Canada because he met a girl who's now his wife. And this incredible programmer couldn't get a job because he was a new immigrant. But he's living in Canada and he decides he would start selling snowboards on the Internet. And he couldn't find any good software to sell these snowboards. It was either very expensive, like a million dollars to build an online store, or you were forced to sell on a marketplace. The predominant one at that point was like ebay, effectively. Amazon did not allow third party sales at this point. So he wrote this piece of code to sell these snowboards. And he realized that the actual code that he had written to sell these snowboards was far more valuable than the snowboard business itself. And he would change his business model to focus on helping others build similar online businesses. And I met Toby around that time and became one of the first merchants to use Shopify and started selling T shirts.
- [30:08]
A
It's so interesting that you went to law school under the idea that it could be or is entrepreneurship finishing school. I went to law school. That was not my experience at all. You actually practiced and. Yeah, well, you did for a year, right? You did for a year.
- [30:23]
B
But you were like, you were a real.
- [30:24]
A
I will say, yeah. I mean, to me, law school was full of people like myself who are. Who are fundamentally safety seekers. They are the opposite of entrepreneurs in terms of their. Their, like, risk tolerance, Right? Like, these are people who are looking for tried and true career trajectories. And those that did have a different kind of relationship with risk got worn down. Right. So people come in, everybody's like, I'm not doing the law firm thing. You know, I'm going to do the nonprofit thing or I'm going to be A DA or a prosecutor. Then the loans, you know, start to add up and they're like, well, maybe just a year. I did the summer associateship. Everyone seemed nice and they took me out to nice restaurants. Maybe it's not so bad. I'll do a year or two. And once you're in, it's very difficult to get out. And I don't know anybody from my law school class who became an entrepreneur. So, yeah, it's interesting. I do think you learn skills that are certainly valuable and applicable in an entrepreneurship context. And you did it in fairness, you did like a joint MBA also. Right. So it wasn't just changing.
- [31:35]
B
If I had to do it all over again, there's not many things I would have changed about sort of my background. But one thing that I would have changed is I probably wouldn't. I didn't think business school was nearly as valuable. I actually think the skill set that I learned in law school was far more valuable than business school. Business school was mostly case study based learning or pedagogy. But law school was read 4000 pages and pick out the one line that matters most. I mean, that is a very difficult task.
- [32:01]
A
It is case study based also, but it is, you have to find. Yeah, it teaches you a different way of thinking, a certain way of analyzing arguments to come up with your own argument, and then stress testing your ability to tell a compelling story.
- [32:16]
B
I actually felt that I really didn't learn how to write very well until I got to law school, where I was forced to write a ton. I mean, memos and just case breakdowns. But also it was things like the Socratic method in class. I don't know if that was how it was in your law school, but at our law school they would just yell out, harley Finkelstein, please tell us about this particular case. And you only had a few minutes and you have to explain a very long case, a very complicated case, in a matter of minutes. That in itself, I think was really, really valuable. I think most people on the law school point, most people, I get people message me all the time now asking me about law school, if they should go. I think that most people today look at education as simply a stepping stone for the next stage of their life. So they go to medical school to become a doctor, they go to law school, become a lawyer. I think if you take a different approach to education, where you look at it almost like a transaction, where you pay tuition and you need to receive this, the same amount of information of knowledge, insight in return, that's the contract you have with the academic institution. And I think if you walk in with that attitude and you're truly be selfish about it. You're like, I'm giving you in Canada, it's cheaper than us, but I'm giving you $15,000 which is what law school cost a year in Canada. I demand you give me $15,000 of insight and knowledge and experience back. And you're not as worried about exams because you don't need a job at a big law firm. You actually look at your day to day course load very, very differently. You begin to pick courses and professors who are much more interesting and inspire you. And you're less concerned about. The famous maxim in college for me was basket weaving classes or there was a famous class in McGill called the Art of Listening which effectively everyone got straight A's in. Why did you take it? You took it because you got straight A's. I would never have done something like that because that wasn't actually a valuable exchange. I wasn't looking for the A or the grade. I was looking for selfishly to derive as much insight as I possibly could. And I actually think a lot of the things I use today on a day to day basis leading a large company I got from law school I did not get from business school.
- [34:24]
A
But you went into it with a conviction and a sense of self and kind of an understanding of where you wanted to go. I think most young people don't have that level of self understanding or conviction.
- [34:36]
B
It is very helpful to know what you want earlier in life.
- [34:39]
A
Yeah, yeah, there's no doubt about that. I mean it's a gift. It's like you can't make yourself that, you know, like that just some people have that, some people don't by dint of circumstance or experience. And I think law school is a place where a lot of people, myself included, kind of go when they're not really sure what they want to do. Right. Hopeful that they'll figure it out.
- [34:57]
B
It's purgatory, you know, it's a career purgatory.
- [34:59]
A
You're sort of being warehoused. That's right.
- [35:02]
B
And the good news is that if you want, you can go and make $250,000 a year out of school after high school. It's purgatory. But there is a default next step.
- [35:13]
A
Yeah, yeah.
- [35:14]
B
And that default next step is like.
- [35:15]
A
By all the safety net is very high.
- [35:17]
B
It's very, very high there. And I'll just continue on.
- [35:29]
A
Holidays mean gift giving. You got to go out there, you Got to find those cool, perfect gifts for all the people you care about in your life. Your peers, your co workers, your family members. And everybody's thinking about what is that perfect gift? What is that cool, unique thing that I could give? Well, what's better than the gift of health? And this is where AG1 comes in. My go to nutritional supplement. I drink it every morning. AG1 has been a game changer. I've been doing this for years. It's just one of my non negotiables because it's packed with nutrients that just do so many things for me. They help me sustain my energy and overall just promote my whole body health with probiotics, with prebiotics and adaptogens. It also supports my immune system. All of these things help me stay on track, especially when I'm traveling without having to think about like what is my supplement stack. So this holiday season, try AG1 for yourself. Or you can gift it to someone special. It's the perfect time to focus on supporting your body with an easy and surprising amazingly delicious daily health drink. Again, it's my go to supplement. And that's why I've been partnering with AG1 for so long. And right now, AG1 is offering new subscribers a free $76 gift. When you sign up, you'll get a welcome kit, a bottle of D3K2 and five free travel packs in your first box. So make sure to check out drinkag1.comrichroll to get this offer. That's drinkag1.com richroll to start your new year on a healthier note. This podcast is in partnership with Airbnb. If financial goals are on your mind for 2025, here's something worth considering. Your empty home could become a source of passive income while you travel. That's the beauty of hosting on Airbnb. What's smart about this is its flexibility. Whether you're taking a quick weekend trip or heading out for a longer stay, your space can work for you. You decide when to host, making it fit seamlessly into your schedule. Lifestyle. It's not about becoming a full time host. What it's about is making the most of what you already have. Maybe you're planning upcoming travels, or perhaps you have an extra room that is just sitting there empty. The point is, there's real potential to create a practical income stream that works around your schedule. Your home might be worth more than you think. This is what I'm trying to say. Find out how much@airbnb.com host I like what you said about this transactional kind of relationship with the academic institution. And on some level, I think that is perhaps a function of the world being very different from when I went to these schools because of the Internet. Like now the aperture is so wide, like, you can see what all these other people are doing, and you can listen to podcasts about how they did it and why they went to law school. And the number of paths is infinite, whereas when I went to school, that didn't exist. It's sort of these very kind of well defined tracks. And anybody who stepped outside of it was sort of not a pariah, but like a little bit weird, you know, like when I was growing up as a kid, I don't think I ever heard the word entrepreneurship once. There was no such thing as entrepreneurship. I mean, there was, but it wasn't like a word that people were saying out loud. Basically, it was business, right? And if you wanted to go into business, you go to college, maybe you get an mba, and then hopefully you get a job at General Foods or General Motors or Procter and Gamble or Boston Consulting or some or, you know, Morgan Stanley or someplace like that. There was no kind of thinking or incentivization around the idea of striking out. If you were going to strike out on your own and start your own business, that was like, oh, you're going to have a sandwich shop or something.
- [39:27]
B
Or you failed, you didn't get the job.
- [39:29]
A
So the Internet didn't exist. So the capacity to scale anything was impossible without capital. And all the things now that has been democratized in no small part because of Shopify and the tools that you make available to people, which has changed everything. And I was so myopic. I was at Stanford in the late 1980s when all of this was being born around me right there. And I was disinterested. Like, it never occurred to me. While I had classmates dropping out to go start their businesses, I thought they were insane. It's like, I'm very late to this party and somebody who became an entrepreneur in the later decades, but the world is very different now. And now being an entrepreneur is sort of this aspirational kind of rock star thing.
- [40:09]
B
Yeah, it's very cool. I do think there is one exception to this sort of philosophy or theory that we're talking about, which is immigrants. My father was an immigrant, and obviously his parents are immigrants also. He came to Canada when he was very young. He was, you know, five or six years old. They came from Hungary to Canada in 1956. My grandparents were Holocaust survivors. They came My grandfather was effectively an entrepreneur. He didn't call himself an entrepreneur. He never articulated that as his, like, life's work. He sold eggs at a farmer's market, a local farmer's market in Montreal, which still exists today. It's called Le Capitaine. My uncle currently runs it. He did that because he had no choice. And so this idea of forced entrepreneurship is something that I've been thinking a lot about more recently, which is that a lot of immigrants have to become entrepreneurs because they don't have a job, they don't have sort of skill set, they don't speak the language. And so no one gives them an opportunity. They must go into it. And then, ironically, what tends to happen on the next generation, that I've noticed, is that a lot of them want their kids to become doctors, lawyers, accountants.
- [41:07]
A
Yeah.
- [41:08]
B
So the people who actually have the most amount of entrepreneurial role models, which are children of immigrants like me, are pushed into, like, law school and medical school and engineering and accounting because they believe that they want a better life for their kids than they had for themselves. And I actually think that there was something to be said about, like, being forced into a particular direction, especially as an immigrant. Like, you just. You get very resourceful. You tend to be antifragile, to use a Nassim Taleb sort of line. I think that more people need to experience or know people that are entrepreneurs in order for them themselves to consider entrepreneurship. My father made me the business cards not because he thought I'd be a good dj, but because to him, starting a business was not that foreign. And it wasn't because he was sophisticated or inspiring or this, you know, this entrepreneur group. Not at all. It's that in his upbringing, he saw people start businesses. And so if his son wants to start a business, that doesn't seem so crazy. And I don't know how to sort of bring more of that back. Actually. I recently just wrote a kid's book about entrepreneurship because my kids are in third grade and kindergarten, and they're both doing these projects called what do you want to be when you grow up? Which is a very common project for children to do. And they brought home their assignment, and it was literally like, circle what you want to be when you grow up. And I had two major issues with this. One was entrepreneurship was not on the list, which I was devastated to see. And second, it was all about what you want to do later in life. And I think that I was fortunate that no one put that in front of me when I was their age. Because if they did, I probably would have pushed out this idea of being a DJ until I was, quote, unquote, grown up. And so I wrote a kid's book, effectively about me becoming a DJ at 13 years old. And I used a couple examples of Shopify merchants. One was 10, one was 12, started what would become multimillion dollar companies in their garages, one in fashion, the other as an artist. I think role modeling is really important. And the original role models for entrepreneurship, I think, are immigrants. And that's what it was for me, 100%.
- [43:15]
A
That's so true and very insightful. And it's always frustrating. As a parent myself, when in school, they're meant to do some exercise, and by definition it's like a limiting exercise, whether it's art class and you gotta draw within the lines or whatever it is. Anything that is an imposition on a child's creativity and expansive kind of perspective of what's possible is infuriating.
- [43:42]
B
And so it's full circle. But I took an entrepreneurial solution there. I met with the administration of her school, I met with the teachers, I met with the principal, and I said, I think you need to have more entrepreneurial curriculum. And I got a bunch of hand wavy stuff. My kids are at a different school now, but I got a bunch of hand. That's true. But I got a bunch of hand waving stuff. And the reason I wrote the book was I needed a Trojan horse. I knew that convincing them to create a curriculum, they would say, we have to go to the school board and all that stuff. But I knew that if I said, hey, I wrote a book and I'm gonna pay for these books. If you like the book and you agree it's a good book, I'm gonna pay to have the books distributed in your school. They would read the book and perhaps someone would take the initiative and create an entrepreneurial program. And that's what I did. I wrote this book. I mean, I really like it. I read to my kids all the time now, but I created a Trojan horse. I took an entrepreneurial approach that they weren't going to listen to me otherwise. So here's a book about entrepreneurship that I think your teachers should read to the students, tell me what you think, and it at least in this particular school, worked.
- [44:42]
A
What are you going to do when your kids want to be doctors and lawyers?
- [44:47]
B
Good question. You know, my wife, who's much smarter, much more thoughtful of parenting than I am, she's also a psychotherapist, has often reminded me that as Much as we are the entrepreneurs. And my wife's a psychotherapist, she's also an ice cream entrepreneur. Like, entrepreneurship is like, our house is full of ideas. We're always talking about new ideas, new projects, new cool things that we're excited about. That there is a chance that one of our kids, or both, may decide to be professionals. The thing that I loathe, and I think that's okay. I think what matters to me more is like, I want them to be people that really give a shit about being lawyers or being doctors. I didn't care about being a lawyer and that I give a shit about the thing. That's actually what I want from them more than I want them to take a particular path.
- [45:33]
A
Sure. Do you think that everybody can be an entrepreneur? You're certainly wired that way. But do you think everybody can have that inclination? As somebody who's kind of democratizing this.
- [45:50]
B
World, I have two thoughts on this, and they're somewhat contradictory. One is that the cost of failure has never been lower for entrepreneurship. Going back to my grandfather's story selling eggs. He comes to Canada from Hungary, has no money, eventually makes a little bit of money just working odd jobs and gets a little egg stall. If that egg stall would have failed, he wouldn't have just lost the egg stall, he would have lost his house, and he would have not been able to put food on the table. The cost of failure in the 50s of entrepreneurship was massive. Today it's not today if you, you know, this is not a pitch for Shopify, but for $39 a month, like price of a couple cups of coffee, you can start a business. And you and I were talking just before we started recording, but, you know, being here in Los Angeles and meeting some of these merchants, some of these merchants that I met with the last 24 hours here that are some of our largest merchants, they started this business at their mom's kitchen table less than a decade ago. And today those are billion dollar companies. So the cost of failure, I think, has ever been lower, and the velocity of business growth has never been higher. I don't know the Nike board, I'm sure they're nice people, but I suspect at some point, inside of a Nike board meeting, the name Gymshark has come up. Someone said, who is Gymshark? How did they get so big, so prolific, so important, so quickly? Ben Francis started that at his college dorm room in the UK 2012. We've never seen companies grow this fast, this quickly and as prominently ever before. So cost of failure is low and the ability to scale has never been higher. The Internet has sort of democratized scale in some ways. Okay, that's on one side. On the other side, I get criticized fairly regularly that I believe that everyone should commercialize everything about their lives, that every hobby should be commercialized. So I don't think that every hobby should be commercialized. I think if you make beautiful blankets for your grandkids and you're listening to this right now, maybe you should just keep making beautiful blankets for your grandkids. But if you really love making those blankets and you're finding yourselves running out of grandkids to make it for, maybe you should set up, you know, bubbiesblankets.com and maybe you should just go to a go on, if you're a grandmother, maybe go on Facebook and you go to Facebook group and you look up a bunch of forums where people are looking for beautiful hand knit products. And maybe you should just put a link there and say, here's an idea, what do you think? Here's a product. What do you think? And let the world gauge whether or not there's a there, there. I want to be careful because I don't think everyone's hobby should be commercialized. Some hobbies should stay hobbies. But I do think that there's a lot of people out there that have these ideas in the shower consistently and perpetually. And for some reason or another, they're scared of the cost or they're scared of the lack of understanding, and they don't do anything with that idea. And that idea may have the potential to be a billion dollar company or maybe just, you know, a company that makes $10,000 a year and that's all you want because that pays for ballet lessons for your granddaughter. I don't think everyone should be an entrepreneur, but I think there are still too few people that are considering entrepreneurship as a meaningful life's work pursuit. And, you know, I've said this a lot and I really believe, I think this is the golden age of entrepreneurship. And I think it's the golden age of entrepreneurship because the cost has never been lower and the distribution channels had never been higher. One of those first stores on Shopify in 2006, I was selling T shirts at that point, even 2006. So not that long ago, less than 20 years ago, the key ingredient for success on Shopify was who can spend more on AdWords, right? And I couldn't outspend Walmart. So no matter how good I was at entrepreneuring, I was never going to build something that would compete with Walmart in this particular vertical of licensed T shirts. That's different now. Now I met a company, Rocky's Matcha, a Los Angeles company. I met him yesterday at Venice beach just to hear his story. And he's telling me a story and he said this publicly, so I don't think he'd mind me sharing this. But he's never spent a dollar, not one dollar on paid advertising. And he's built one of the most important modern matcha companies like in America, simply by hustle and grit and great product and being at the right coffee shops. And that's why I think right now is such a great time to do it. And so to answer your question more directly, no, I don't think everyone should be an entrepreneur. But I do think that there is a lack of people that are trying it who I think could be very successful at it.
- [50:24]
A
There's something generative about it. Obviously. You create something, you offer it to other people and if other people enjoy that, there's a connection. There's a sort of community building piece to it. And it's very self affirming. There's a sense of agency over your life because if you're in a corporation or go to a more kind of typical 9 to 5 job, you can perform your job well and you can be, you know, well reviewed and all that sort of stuff and feel good about the work that you're doing. But it's always on behalf of somebody else's mission, right? And when it's your own mission, there is something, you know, just incredibly uplifting about that. And I'm interested in this thing that you said that stuck out to me, which is entrepreneurship is the greatest tool to self actualize, to solve a problem, to find success and to find ourselves. So what I gather from that quote, and please tell me, is that it's like this lever for personal development on some level, like it's more than just business creating some independence for yourself, whether it's a side hustle or your main thing.
- [51:32]
B
So earlier we talked about balance, we talked about this idea of enough and side quests and main quests and all that. The flip side of it is that I don't necessarily think this idea that your work life and your life life need to be disconnected. And I think one of the best ways to merge those two things is through entrepreneurship. Now again, the caveat is I'm not suggesting that every hobby should be commercialized, although I think a lot of people's hobbies could be Their incredible ventures and some of the best businesses on Shopify started as someone's hobby, became a business that eventually became Figs, Trina's company, Figs, now publicly traded billion dollar company making hospital scrubs which is amazing business. So I see that very, very often. But I think the greatest way for humans that I've seen to find their thing, to be more creative, to solve their problem, but also just to enjoy their day to day is through entrepreneurship. And it's not to say it's easy. In fact, I think I often may glamorize entrepreneurship and often may neglect the fact that most businesses do fail.
- [52:38]
A
Yeah, even those hobbies that become giant companies, I mean there's a trail of tears for sure. These things aren't, they're not always going to be successful.
- [52:47]
B
That's exactly right. And in fact you have to keep almost like reinventing your as time progresses. But I do think though that access to entrepreneurship as a tool to find your thing was not possible to the extent that it is today, even 15 years ago. And it wasn't just Shopify. I mean the Internet, technology, a lot of these things are sort of creating this as well. Consumers, consumers today are voting with their wallets to buy from brands that they love. You and I talked about a bunch of brands before we got on today. Those brands, when you buy from some of those brands, when you buy from Vuori, for example, at least when I buy from Vuori, one of my favorite brands, I'm not trying just to buy a pair of shorts or a T shirt. I'm also voting with my wallet to say I want more of those companies, those brands to exist in the world. Yes, I like the more traditional big box brands too. But I think what Vuori is doing is fantastic. The way that I can support them as a consumer is by buying from them as well. So I think consumer choice, for a long time it was I will buy direct from the brand or the merchant if it's really convenient. And now I think it's actually gone past that, which is consumers actually prefer to buy direct from the brand or the merchant whenever possible. And that's a switch that only happened in the last decade. Part of it was even though you could buy from a direct brand, an independent brand, it was less convenient. You went to a big box store, returns, the cash register was right there. They had your information on file. But now, using a term we both learned in law school, Senari's paribus, all things being equal, I think consumers prefer to buy direct from the brands that they love. And so when you line up all these things, technology, distribution, becoming democratized, and consumers preferences and how they purchase changing, you end up with this incredible surface area of opportunity. I have a pretty good purview of entrepreneurship. I think from the seat that I sit in and the people that I speak to that have left the job they didn't like or found success using entrepreneurship, they're pretty damn happy about it.
- [54:52]
A
Yeah, I've noticed that in my own personal life, like most of the things that I buy, like apparel stuff that I buy is based on what I see on Instagram. Like the algorithms figured me out and it sends me cool stuff that I'm like into from companies I've never heard of before. And I'm like, I'll try that. I don't know if it looks cool. We'll see. I'll take a flyer. And thanks to you, like, it's one button.
- [55:16]
B
Yeah.
- [55:17]
A
Shop pays pretty good.
- [55:18]
B
Shop pays pretty good. Pretty easy.
- [55:21]
A
You've been instrumental in helping me spend more money with all the money in my wallet.
- [55:25]
B
That's right.
- [55:26]
A
But I love the Shop app and then it tracks everything so you know exactly where everything is and when everything's coming. Which makes me feel more comfortable about like, oh, I didn't. I forgot about that thing that I ordered and who knows what happened to it.
- [55:37]
B
Yeah. But even in terms of your.
- [55:38]
A
And I love these little brands that show up and I'm like, that looks really cool. I would have never known about this. And now I've become loyal to certain tiny little brands because they over delivered and I love their stuff and I continue to buy from them.
- [55:52]
B
And those little brands that over deliver. That over delivering is often something that the large companies cannot do. They can't do it because it doesn't scale well. There's a great brand on Shopify called Tacovis which makes beautiful, beautiful boot like boots, like cowboy boots. I'm not a cowboy, I'm a sneaker guy. But they make beautiful boots. And one of the coolest parts is they have about 40 stores across America right now. Great online store. And I've got to know this team really, really well. They have a bar in every store and not like an unironic bar. You know, a lot of retail stores added DJs and coffee bars and they have like an actual cocktail bar and it just, it fits perfectly in there. And one of the things they are able to do is they're able to get to know their customers. So they know your drink. That is something that works with 40 stores, it doesn't work with 4,000 stores. So the brands that are over delivering, part of the reason they can over deliver is because they're able to have this one to one relationship with the consumer. But it's also reciprocated by the consumer. The consumer is now saying, if I need another pair of boots, I'm gonna go back to this particular store. I have a relationship. And I don't think we as humans have historically, like, you know, hundreds of years ago, you bought the bread from the baker and you bought your shoes from the cobbler and you went direct to consumer. And then you had this like this 200 year period of intermediation. And actually the person who caused that was a guy named John Wanamaker. 1876 created Wanamaker's department stores in Philadelphia. That was the first time that a bunch of stores were under one roof in America. Sort of the origin of the department store. And if you sort of track, essentially from that point until 10 years ago, retail was pretty, was pretty much the same. Bigger stores, they added, you know, bigger food courts. Some of them had like, you know, go karts or they had, you know, water parks. But it was basically the same thing. And it's only been the last 10 years or so that retail feels really exciting again. And why? It's because people that care about the things that they use. I care about this pen. I think it's a really great pen. I really love this Moleskine notebook. These things matter to me. I selected this intentionally and this intentionally. The people that care about that stuff, we are finding more joy and more delight from brands that tend to be independent, modern brands. And that's what's creating all of this. Which means that if you have an idea and you want to create something that doesn't exist yet, you will likely have an audience somewhere in the world for your particular product. And it's easier now to find than ever before.
- [58:10]
A
And when those customers feel well taken care of, they become the evangelists of that brand.
- [58:17]
B
Totally.
- [58:18]
A
Where is your head in terms of the future of retail? Like, we're in a really interesting moment right now. It's cyclical. Obviously we went through the pandemic and I know that was sort of a crucial moment for Shopify. But we saw the retraction of retail. Everything closed down and now we're seeing the reemergence of retail. But retail seems to only work when they've eventized the experience. There has to be like going to a movie, there has to be something more than I'm just going to the shop to get my thing. It has to be an experience that's been cultivated and that seems what works best. So even the most ardent digital direct to consumer brands are now opening flagship stores in fancy parts of metropolitan cities across the world. Those are capital intensive things. So where's your head at in terms of where retail is headed and what the future of retail looks like for those smaller cool brands that are doing well on Instagram but aren't going to be opening up up an Apple Store type experience on Broadway?
- [59:28]
B
Yeah, there are these brands that just really, really understand their consumer. The best example I can give you is Shopify Merchant. That I've was one of my like, you know, I have a bunch of these like Moby Dicks, these like big brands that I really want to get on Shopify. One of my big brands that I really want on Shopify was Supreme. I think what supreme has done not just for skateboard culture but just from retail is nothing short of remarkable. Here's a company that every Thursday at 11am Eastern Standard Time they have a flash sale, supreme.com. when you go to the flash sale like you go to their online store, it's not easy to navigate. It's sort of a puzzle. You see little slivers of the different products, skateboard, a T shirt, a hoodie, whatever. And the loyalty and the connection that the consumers, the fans of Serene have to them is enduring. I mean, Supreme's not a new company, right? They've been sold a bunch of times. I think VF Corp. Just sold them to private equity. But they have a really good understanding of what they do very well. If you've been to a Supreme physical store, it's not that nice of a store inside, it's kind of a warehouse. But they have a really good understanding of it.
- [60:36]
A
And there's always a line and there's always a line on the side street in New York City. Every time you go by there, there's like 50 to 100 people in line waiting to get there.
- [60:43]
B
That's exactly right. Right down the street from there is Kith, who also has a line but very different experience inside. It's like a beautiful museum. There's Kith treats, beautiful like ice cream bar. There's a lot of art. I know you're into bear brick. Like there's bear bricks everywhere, right? Like cause dolls, it's like, it's an amazing experience. They're a streetwear brand that just did a collaboration with Giorgio Armani and Martin Scorsese. Is sort of one of the like was the model.
- [61:09]
A
Yeah, those, those videos. I've seen those videos.
- [61:11]
B
It's unbelievable. You have that on one side, on the other side, you have brands that. I'll mention this brand again. Figs who realized that doctors and frontline workers and nurses in the hospital, in doctor's offices, in the clinics, they were all wearing these kind of shitty scrubs. They didn't look good, they didn't fit well. Just it was basic. And they're like, we can do this better. And they completely disrupted that market. And they have figured out a way to really tap into frontline workers. They work with hospitals, they figure out a way. During the pandemic, they actually put up a job site to help frontline workers find new work. If their particular clinic shut down, there'd be another clinic. I think there's a timelessness to this strategy, which is deep empathy for your customer. And if you really understand your customer, you do really, really well. A couple years ago, this isn't a strike against Starbucks, but I remember talking to my niece about Starbucks and her telling me that she no longer goes to Starbucks. And I said, why? And it was something to do with they changed their points program. And my niece wasn't really into coffee per se, but she loved her Starbucks point card. It was this point of pride for her, this special card she had. What Starbucks missed in that transaction was the people that were coming in there. Some of them really loved coffee. They were coffee snobs. But a lot of them were simply like, they believed in this loyalty program so much. When you changed it, it was almost as if they kind of forgot about who they were serving. When you look across the millions of stores on Shopify, the ones that are most successful are the ones that have deep empathy from a sales channel perspective. What that also means is Kyle Leahy, CEO of a company called Glossier Amazing Cosmetics Company. If you ask Kyle during the pandemic. The reason I bring this up is during the pandemic, while everyone was shutting down their physical retailers, Glossier was opening new stores, physical stores, making beautiful stores, so in anticipation that when the pandemic lifts, they are going to have these amazing in store experiences. But if you ask Kyle about is Glossier predominantly online or offline, she'll tell you that's the wrong question. She'll say that we are everywhere our consumer wants us to be. And right now, the consumer for Glossier wants to go in store, but they also want to buy online and they also want to, you know, shop on Instagram and on TikTok. And so as, as their commerce partner, we have to be in all those places. We just announced a commerce partnership with Roblox two weeks ago. Why? Because some brands some of the time are gonna wanna sell inside of Roblox. Cause that's where their customers are. That doesn't mean that kith should sell in Roblox. It means that some other brands that really have an empathy for their customers and those customers spend time there should sell there too. So my belief is that the future of retail is not online or offline. It's retail everywhere. And every single surface area that exists where consumers and humans spend their time should be a potential place to have a transaction. Not because we need to commercialize the world, but because it's more convenient that way. And one of my favorite brands is James Purse. I wear a black T shirt usually made by James. James is also a good friend. I think he's one of the best entrepreneurs on the planet. I had lunch with him for 10 years.
- [64:14]
A
Tell her to lower the prices on those T shirts.
- [64:17]
B
It's insane, but it is insane. But I mean, I'm wearing it. It's my suit.
- [64:20]
A
I have a few, but it's like, it's so expensive.
- [64:22]
B
It's very expensive.
- [64:23]
A
I can't justify this.
- [64:25]
B
So James has a bunch of James Purse villas in cobbler though. And these villas are fascinating. Not because their villas and their couple is a nice place too, but when you rent these houses, anyone can rent them.
- [64:39]
A
You're in the James Purse universe. Like it's an experience. Sort of like Armani, right? Like it's all curated, like the experience.
- [64:45]
B
He goes one step further. He knows your sizes, he knows what you've bought because he's got a great CRM. He knows everything about your purchase history with their brand. So when you go into your bedroom and you open up the closet, there is stuff there in your size, presumably stuff you don't already have that may actually match well with the stuff you do already have. And you can simply take a photo of it or you can scan it and you can easily transact on hangers.
- [65:07]
A
That are all like exactly one inch apart from each other.
- [65:11]
B
Someone is a little bit ocd. I kind of love that. So if another brand went ahead and did that, it wouldn't make any sense. But if you know the James Purse brand, you know that it's very.
- [65:20]
A
It's consistent with design architecture.
- [65:23]
B
James makes the playlist for all his stores. He picks his sense of all his stores. The floorboards in his stores are perfect, not perfect for any store, for James Purse stores. And I think that is something that is a timeless strategy around empathy and authenticity. And I don't think it's going away.
- [65:49]
A
Let's be honest, what most people really want for the holidays is to see their favorite people more often. And that's why this year the best gift you can give is an Aura digital picture frame. I use mine to share everything from daily moments to family gatherings, and it's kind of amazing to see my loved ones react to these photos in real time. Name the number one digital photo frame by Wirecast. Aura lets you upload unlimited photos and videos directly from your phone. The free unlimited storage means you can share as many moments as you want and the frame automatically adjusts to room lighting, making every photo look like a professional print. What I love most is that you can preload it with meaningful photos using the Aura app, making it the perfect surprise gift for even those, let's just call them a little less than tech savvy. You know who I'm talking about and that's ready to go right out of the box. Save on the perfect gift by visiting auraframes.com to get 35 off or as best selling Harbor Mat frames again Promo Code Rich Roll at checkout that's a U R A frames.com promo code Rich Roll this deal is exclusive to all of you my listeners. So get yours now in time for the holidays. Terms and conditions apply. This show is sponsored by BetterHelp, the holiday season. It's here and you know, it's a lot. I mean, sure, it's about all the good tidings, all of that kind of stuff. But it's also important to acknowledge that it's also kind of a tough time of year. It comes with financial pressure, social, social pressure, fraught family gatherings, and this expectation to be jolly at a time of the year, at least in the Northern hemisphere. When it's cold, it's dark, it's a little dreary, and every instinct is to kind of hibernate. Which are all reasons why I personally always double down on therapy this time of year so I can actually enjoy the season and show up for the people I care about with my best self. If you're thinking of starting therapy, I can't recommend it enough. And BetterHelp is a great way to get into it. It's entirely online. It's designed to be convenient, flexible, and suited to your schedule. Just fill out a brief questionnaire and get matched with a licensed therapist and you can switch therapists anytime for no additional charge. Find comfort this December with BetterHelp. Visit betterhelp.com richroll today to to get 10% off your first month. That's BetterHelp. H-E-L-P.com richroll what's distinctive and interesting about Shopify is at the beginning you identified a need in the marketplace. Like, nobody is doing E commerce software that's consumer friendly and available. There's enterprise software, super expensive. But there wasn't really a solution for the average person or the hobbyist, et cetera. You would think with that, okay, we're going to fulfill that need and then, and then that is our customer base, that we're going to serve the people that can't afford the high end. But today you're serving everybody. You've got Fortune 500 companies, these gigantic legacy companies, but you're still serving the mom and pop shops, right? Like walk me through, like how you've been able to kind of serve all masters in that regard without like losing focus and whether at some point there was a conversation like, hey, listen, we need to choose here. We can't be everything to everybody. But somehow you figured out how to kind of do that.
- [69:31]
B
We went public May 2015 and in February 2014 we introduced effectively our enterprise plan. We called it Shopify Plus. And the reason we did that was what happened around that time was a bunch of these really small businesses got really big on the platform. So those stores that start their mom's kitchen table, which frankly no one really knew was gonna happen, some of them started to do like 100 million bucks a year, $200 million a year. I was like, wow, these are big businesses now. They didn't leave the platform. There wasn't this graduation off the platform. So let's use email marketing. With most software, like email marketing, you'll start with like the BCC line is what you'll use and then eventually you'll upgrade to like, I don't know, mailchimp and eventually constant contact and eventually you upgrade to like exact Target. There's like enterprise software line for email marketing. Same thing with accounting, right? Maybe you start with QuickBooks and eventually you end up with like Oracle Financial or Netsuite or something like that. In most software verticals there is this natural graduation as you get larger because the things you need when you're starting, which is like, you know, like very simple, you use some sort of consumer friendly. It's exactly the right term. The UI has to be simple. You can't overload the features. Otherwise you get sort of the paradox of choice and you spin. You need things that are very, very simple to use and not intimidating, especially if you're starting a new business. But when you're supreme and you're doing massive flash sales, the requirements you have are totally different. Or if you're Mattel for example, which another one of our stores. So 2014, we create this plan to allow small merchants that get really large to graduate too, with additional functionality, with additional API call limits and additional throughput in case during a flash sale, things like that. And that's sort of where we're sort of sitting. For a while, it was the best place to start a brand new business. And in the case that your business gets really big and really successful, you never have to leave the platform. IPO happens. The ipo. Most people don't talk about it this way, but the IPO is not just an interesting event internally, but it also provides, I think it's almost like an external branding moment. Like all of a sudden people that are not in E commerce started hearing about Shopify. We started to get phone calls from more traditional companies, companies like Staples for example, or Mattel for example, or Procter and Gamble. And they were interested in looking at Shopify and we were fascinated by this. We're like, you know, most of them have custom stacks or they're using some sort of big enterprise software. Why would they think about Shopify? Well, it turned out that even though Shopify was software built for entrepreneurs, that in these companies there were these entrepreneurial people. I hate the term intrapreneurs, so I'm not going to use that. But there are these very entrepreneurial people in these companies and they were sick of having to do service call every time they want to add a sku. They're like, it doesn't make any sense. We just want to, we want to change something. We have to call some big enterprise software company. It's ridiculous. The cost was insane. And so what happened was a lot of these very large brands began to act like entrepreneurs. And in many ways they sort of stretched us up market. They said, well, we know you don't have everything, but we think we can do everything we need as long as you. What they said to us was, as long as you make the important thing is easy and everything else possible, we can use Shopify. And so that was sort of the philosophy we use. Make the important things really easy. So setting up a payment account, getting a domain configured, picking a theme, adding products, doing basic order fulfillment, you know, doing basic marketing on AdWords or Instagram ads. That stuff has to be incredible whether you're small or big. But then all the other stuff I want to sell internationally, I want to do B2B wholesale. I want to add a point of sale terminal so I can sell in my physical stores too. We made all that possible for. And the real trick to this whole thing was the complexity of the software needs to reveal itself only at the time that the merchant requires it. Because if it reveals the complexity too early, it's disorienting, it's the worst thing in the world. You're gonna confuse them. And so we made a very conscious decision. We're not going to shift up market, but rather we're gonna stretch up market. And we wanna be the place where everyone goes to start a business. But we also wanna be the place that, that modern brands doesn't mean they have to be like new, but modern thinking, modern entrepreneurial brands that are even very large ones can also go to run their entire stack. And that's the reason why we have such a large cohort now, a very large enterprise business, because as they grow, they can do all that with Shopify. The other thing that's important that we got criticized for on the ipo, but now the, you know, things seem to change a little bit as sort of commerce evolves, is that we don't just want to be E commerce, we want to make it easy to sell across every single surface area, as I mentioned. So what Shopify really is today is more of a retail operating system than an E commerce platform. And why does that matter? It matters because there's going to be a time in the future that someone comes to us to sell a product and the only place they want to sell it on is augmented reality. They're not gonna have an online store, they're not gonna have a physical retail store. They're just gonna be powered inside of like, you know, some sort of goggles, Apple vision power situation or the Orion glasses from Met or something like that.
- [74:42]
A
Or within some video game.
- [74:44]
B
Correct. No one is looking for that right now. But Shopify has to build stuff like that in anticipation that when they're ready, they simply go to the admin and click AR channel and it activates. And so that's kind of how we're trying to think about this idea of modern retail and modern commerce, which is whatever size you're at, if you want to do, if you want to sell across any platform in any country, if you want to be default global, if you want to scale, do massive flash sales. You can do so with us. And that's been a huge challenge from a product and technology perspective.
- [75:14]
A
Every company has a life cycle, seasons, things change. You were at Shopify in the very beginning when it was Tobias and you and everything was very exciting. And perhaps that leveraged the best of what you could offer as an entrepreneur. But as companies grow and scale, then they become institutions, right? And you're faced with the prospect of doing all sorts of things or being responsible for doing things that are outside of your core skill set or your passion. You got to manage people, you got to deal with spreadsheets and account like all this admin stuff and everything that gets packed into it. So how have you navigated that for yourself as an entrepreneur? To stay fresh and make sure that you're leveraging the best of what you have to offer for the benefit of the organization, while also simultaneously making sure that your employees and your staff are well situated. We all know the story of people who do really well at their job and then they get promoted, they get a better salary, but suddenly they're doing a job that they're ill suited towards or one that doesn't give them the level of satisfaction and fiscal.
- [76:22]
B
Peter Principal. There's a term for it. Peter Principle is eventually if I got.
- [76:26]
A
My mba, you would have known that.
- [76:27]
B
Now it's a silly term. I don't know who Peter is.
- [76:29]
A
They didn't teach that in law school.
- [76:31]
B
Unfortunately they did not. I think at the early stages of most companies, especially when you have a small team, there are no dedicated roles. It's the only question you should ask yourself is how do I add the most amount of value? And when I came to Shopify 15 years ago, it was a group of engineers, very, very smart. And the only thing that, the only thing that I had to do was figure out a way to do the things that no one else was doing. We didn't have a CFO when we raised our Series A. We didn't have a chief marketing officer. We were a scrappy bunch. And so I played this sort of, you know, what's now known as like the Swiss army knife role. How can I help? How can I be most valuable? How can I have the biggest impact? I think that's the only way to get through those first couple of years. I think if you begin to self identify of a particular role or give yourself a particular title, you end up in a box. And that's not what early startups need. Early startups need people that are just doing A lot of different things and. And just trying to keep your head above water. There's no room for selective roles. You kind of have to just get it done. Unfortunately, what ends up happening as you sort of articulate is that as you get bigger, there's no threshold where you're like, okay, now I'm going to specialize on a very personal level. There were people that I admired at other very large companies, much larger than Shopify, who sort of played these. The role of sort of business leader or, you know, chief business officer type people. They were so well rounded. They were, like, really good at a lot of things. They were good at, like, operations, good at finance, good at marketing, good at product, good at engineering. They're kind of good at everything. And I was like, wow. Like, that's kind of what I think I have to be with the benefit of time. In hindsight, I realized I made some. That was a mistake that I ended up. There was a period of time where I was the chief operating officer of Shopify, COO of Shopify for about five years. And I care so much about Shopify and I care about impact and performance that I figured it out to the best of my ability. But there was no way, absolutely no way I was ever going to be the best in the world at that particular role. It wasn't what I was thinking about in the shower. It wasn't my ground state. It was only in the pandemic where things got a little crazy at Shopify. We ended up divesting a fulfillment business. We ended up having to do some layoffs. Went from about 14,000 people to about 8 or 9,000 people. We effectively turned over our leadership team and brought in some new people. It was this great opportunity for us to sort of rethink how we want to run the business. The credit goes to Toby in this, that he was really thoughtful, but he's like, we don't all have to be good at everything. However, the thing that we are doing, we have to believe that at some point we can be the best at the world at it. And what that meant was he was going to be the chief product officer. And he's correct on this, that there was no one that was going to build a better product for the company at the high level than he would. And we would find someone to actually take on the role of coo who loved operations, who loved those details, making sure the trains run on time. And there happened to be someone in our company, Kaz, who was very much like that. He's been our COO since that time. And I really wanted to be this storyteller. I wanted to be the person that told the whole world about shopify, investors, media, the public, merchants, entrepreneurs everywhere, partners. And internally. I want to be the person that storytells culture, onboarding, making sure that we are all pointed in the right direction. And I think for a long time I didn't know if that was good enough, if that was enough. And it was only when Toby said, look, this thing that you love doing, this storytelling thing that is super valuable, do you think one day you potentially could be one of the best in the world at this thing? I was like, I think I can. I'm not there yet, but I think I do this really well. And he's like, well, then stop being well rounded and start being a very pointy object. Don't worry about the well rounded. Be self aware enough to know what you're not good at. Hire the best people in the world for that stuff too. But keep sharpening your point. And the metaphor that I like to use for this is when companies get larger, you put these beautiful spiky rocks in the riverbed and over a long period of time, they become smooth and they become like river stones. And that's what I think happens with corporate inertia, that we all become well rounded. Because I know it's not your job, but just try this on. And I know you're not really good at that, but just take this. Like we have no, it's a holding pattern, but let's just do that for now. And eventually you end up with these roles that are, you have to kind of be well rounded. And I don't think there's any real alpha in that. And one of the terms right now that's very current, very kind of like the cool term in tech is founder mode.
- [81:18]
A
Founder mode? Yeah, everyone's talking about founder mode. I had that, that written down as something to founder about.
- [81:24]
B
Well, it's not.
- [81:25]
A
It's sort of like alpha male, like virtue signaling something.
- [81:29]
B
But also all it means is like, you need to be in the details. You actually like founder mode. And I'm sure there's sure people are gonna be using it to excuse a ton of bad behavior as well. But ultimately what I think what it describes is this idea that there is this trust, battery of legitimacy that founders and early people and leaders get when they've been around for a long. And you can deploy that legitimacy, you can deploy that trust battery and say, look, this thing really, really matters. We have to do it this way, I'm certain of it. And I'm certain of it because I have 15 years worth of precedent that suggests that this is the way we have to do it. And I think it also speaks to this idea of micromanagement, which has a connotation of being a very negative thing. And I'm certain, at least today, in my role in the storytelling side of Shopify, I probably micromanage. I don't think that's a bad thing. I think the people that work with me don't think it's a bad thing either. If I care that much about a particular sequence of words on an earnings call or in a press release or on a tweet or an X post that we put out there, it's not because I don't trust them. It's because I really give a shit. I really want this to be really fantastic and really impactful. But I think this idea of moving from well, rounded objects into pointy, like, sharp points around a particular skill set first, I think it's more impactful, but also it means that I think you get more longevity, you get more longer tenure from the people that are really fantastic at your company. If you can identify. And that's really what Toby did for me. He identified this thing that I didn't have a name for and said, storytelling. You are really good at that. That is super impactful. No one else can do that. Like, you can just do that, but do it better than anyone else on the planet can do it. And that's the requirement. That's sort of the exchange. That's the agreement we make. And then every year, you must requalify. Now, that's really difficult because if you think about Law 2 of Ecology is that for a species to survive in any environment, the species must grow at an equal to or greater pace than the environment changing itself. It's kind of like that at companies and at a company like Shopify that is growing last quarter, let's use revenue, for example, our revenue grew above 20% year on year. Shopify is growing 20% year on year. I have to grow at an equal rate or greater rate to that. That gets really, really difficult. I think that's incredibly motivating. I think that is like, I'm here for that. I find it uncomfortable, I find it challenging. I find it exhilarating. And it means that it doesn't get stale or boring for me.
- [84:13]
A
But also, how do you know, like, yes, okay, I need to grow, and my growth has to outpace the growth of this. Behemoth that I'm in charge of. But what does that actually mean? Like, what do you mean? Like, how am I supposed to do that? In which ways? And like, where is the growth that awaits me that I need most in order to be able to interface with the growth that's coming up behind me right here? Like, yeah, there's an uncertainty.
- [84:37]
B
It's really difficult because, you know, quantifying Shopify's growth is very objective. Quantifying my growth as a leader is very subjective. Part of it is, do I believe I'm doing a better job than I did a year ago? If I watch, you know, an interview that I did, or a call that I did, or, you know, a deal, a partnership deal that I, that I did, If I did it now, would I do it differently? Would I do it better? What did I learn from that? So some of it is just sort of like internally motivated and some of it is, we have a board, we have investors. What do they think? How do they think I'm doing? And it's also where having really good mentors is really helpful because if you have a really good mentor, they don't just teach you stuff, they also call you out on stuff.
- [85:18]
A
Sure they're going to be like, you've got to have those people around, you.
- [85:22]
B
Need those truth tellers. But that I think that's sort of how we run the company today. Shopify is not a group of well rounded people. Shopify is a group of spiky objects that, that all are very committed to their particular craft and are committed to being some of the best people in the world that are doing it. And it certainly makes for more colorful meetings and off sites. But we're not here for second place.
- [85:48]
A
I like what you said about the sort of conundrum or tension between ideas like founder mode. You have to be granular about everything. You gotta have your roll up your sleeves and you're in the details on every single thing. Or you're not, you're, you're not worthy of the founder status. Right? Just relentlessness. But you can't grow unless you delegate and trust those people to do their job. And both of those things are true. Right? And so the job really is, how do you reconcile those on a case by case, minute by minute, individual by individual basis?
- [86:22]
B
There's a great metaphor that, that I love, which is the trust battery metaphor. We talk about this a lot inside of Shopify, but basically everyone that starts at the company starts at a 50% trust battery. Again, the trust battery is a Metaphor. So you're not going to go by force.
- [86:34]
A
You get a certain level of trust, but then you got to earn the rest.
- [86:36]
B
Exactly. And how do you earn it? You earn it by doing what you say you're going to do in a consistent basis. And eventually if you can get to that 100% mark or get close to that again, it's not exact, but you begin to have more of a trust but verify relationship with that person as opposed to verify it and verify.
- [86:53]
A
Does everybody have a little icon on their off how much their battery is charged?
- [86:58]
B
Although that'd be. That would be amazing. I think Ray Dalio talks about a little bit of that in Principles of what they've done at Bridgewater, where you effectively have a trustworthiness score. So he's really actually done it, he's objectively quantified it, but the opposite is also true. And if you don't do what you're saying you're going to do on a consistent basis, then eventually trust battery goes down and down and then eventually an old cell phone battery is impossible to recharge. And that's what I think you have to say. Goodbye.
- [87:28]
A
I want to talk about the storytelling piece here. I feel like story is everything. You're a very good storyteller. You are like the public facing Persona of Shopify. You are Shopify when you go and you do interviews and you're on television, et cetera. And that role really is vital. I feel like it's underestimated the power of a story well told. And I was at a event recently, a couple weeks ago, and I saw a presentation, a really compelling presentation by two guys who are former Chiat Day executives who created this agency called Founder fndr. They're here in la and it was a whole presentation on story and how critical story is in terms of understanding the mission that your company is on and then effectively communicating that mission to the public, to the investors, to the market, et cetera. They deconstructed the whole thing. And these are guys who worked with Steve Jobs intimately. They worked with Brian Chesky at Airbnb, they worked with Evan Spiegel at Snap. Like they're high level dudes, right? And the way they broke it down, like, you've got to understand your story from top to bottom, but from bottom up. And like there's a whole like science and art to drilling down on exactly how you articulate what you're doing. That brings clarity to the people who have signed up for this mission and the people who are running it. It is from that which all these decisions get made. When you say yes, when you say no. All of that stems from truly understanding this concrete story. Much like when you're creating a synopsis for a movie, there's an efficiency to it. How few words can you use? How do you get to the absolute essence of what it is that you're doing and what you're trying to achieve?
- [89:20]
B
In my view, my perspective, the best companies don't just have great product, they also have a great story around that product. And I think we are fortunate because the story around I think our product is truly world class. But the story around it is all about success, your own version of success. It's about opportunity, it's about democratizing your think, distributing something that really matters to you. But I also think it is easier to tell a good story if you have tenure, if you have longevity, if you really believe in this thing. Many years ago, I met a very well known, very senior executive who's now in his 80s and he'd worked at eight of the largest 50 largest companies in America. And I asked him about the different products and what compelled him to go work at this company versus that company. And he's like. Like, it was all just widgets to me. And he wasn't saying that in a pejorative way. He wasn't saying that in a pokey way of like that company. It was all widgets to me. And he's like, I used the same tactics and the same strategy at Company A as I did at Company H. And I said, that sucks. He's like, what do you mean it sucks? He's like, I made a fortune of money. I was like, that is the opposite of what I'm trying to cultivate, both with Shopify, but also in my own life. That I think when the company and the product and the mission is deeply personal to you, you tell a better story, you work harder, you build better products, you have more empathy for the people using it. I think the days of company leaders and business leaders selling widgets is over. And the best example of that is Elon. I mean, Elon say what you want about certain proclivities he has, but who could run Tesla or SpaceX better than him? He just, he lives this stuff, he dreams about this stuff. And I think for a long time there was this really, really dangerous version of business evolution where at some point the founders or the early people are swapped out for professional managers. In some cases it works great, but.
- [91:24]
A
You hear it all the time. You hear it all the Time private equity comes in or whatever, they replace the founder. Yeah. Like we're going to put in operators, these people. This guy was at Pepsi or whatever, Coca Cola, going through the rundown right as we speak.
- [91:37]
B
They're bringing someone.
- [91:38]
A
It's a reckoning.
- [91:39]
B
That's right, it's a reckoning. And the person that is going in.
- [91:42]
A
Because the vision exited.
- [91:45]
B
Exactly.
- [91:45]
A
And without that, the entire mission capsized.
- [91:49]
B
So even if you have the greatest infrastructure and they do even have the greatest operational excellence and they do. If you lose the soul, you lose the story. I don't think you can build multi generational companies that are lasting. So I think story is important. I think it's always been important. But it does feel more authentic now when you have someone telling the story of a company who bleeds green in our case or who bleeds. Whatever. Nike, the swoosh in Nike's case. And it'll be fascinating because I think the person that just became CEO had been there for like 30 years or something. Right. Started as an intern and worked his way up into this role. I mean, it's kind of in a.
- [92:25]
A
Which is interesting. Very interesting. Yeah. Cause usually that person comes from the outside.
- [92:29]
B
That's right. Well, you know, the previous CEO of Nike was from the outside and came from consulting. And now the new one was an intern who sort of worked his way up over 30 years and now became CEO. Like, it's just an amazing. I mean, it feels very Phil Knight, shoe dog esque.
- [92:43]
A
But here's the button on this whole thing you guys work with on, right? Yeah, here we go. They're our favorite breakup partner. Talk about visionary. You know, like they're truly innovating the space. It's super exciting to be affiliated with them.
- [92:57]
B
They're amazing companies, amazing company. So when I hear the ON founders, the three of them speak about on, it doesn't feel like they're speaking about widgets. It feels like they're speaking about their children. And you can say, well, is that healthy? Is that good? I think it is. I think when you are bought as a consumer, whether it's B2B software or it's whatever you're purchasing or it's pens, when you know that the person creating it, the person in charge of this thing, cares so much about this thing, it changes the dynamic of transaction. It goes back to that. I'm not just giving you money for this pen. I'm voting with my wallet for these types of this craftsmanship to exist. It's that back to Steve Jobs talking about the. What was it? The carpenter who cared about the back of the bookshelf as much as the front. A professional manager. Some may, there's some really good professional may care about the back of the bookshelf, but the founder definitely cares about the back of the bookshelf. They care about the commons, they care about the way it feels. They care about the delight, the little je ne sais quoi of the whole thing. And it's the reason why I wear James Purse T shirts. It's the reason why I like on running shoes. Because the people that are responsible for design and the actual production of it, both in, on and with James Purse, it's the founders. And in both cases, just to say the thing, they don't have to work anymore. A lot of these people don't have to work anymore, but they still choose to do so because it's their life's work. And I think that is the best part about brands and businesses in 2024. It doesn't feel transactional anymore as the way it does. It feels more personal, more intimate in the best way possible.
- [94:41]
A
And that intimacy can be maintained at the ons, who are growing at astronomical rates all the way down to the creator economy. Right. You, you've built these tools that now allow so many digital creators to connect with their audience by dint of like, you know, really authentic offerings that they care about. Like, I saw that you just. I think it was today, maybe. Was it yesterday or. Yeah, I think it was today. You posted about Tom Holland who just announced the launch of Beero.
- [95:13]
B
His non alcoholic drink, which I've tried, is delicious.
- [95:15]
A
It's good. He was here a couple months ago and we recorded a podcast to help him tell that whole story. That one's going up this weekend because now it's public, but we were. Yeah, he was here a while ago. It's like doing something new. Yeah.
- [95:27]
B
So two years. So part of his journey was.
- [95:28]
A
And it's authentically who he is. Right. Like, this is an outgrowth of his own kind of, you know, personal development in this space and, you know, going alcohol free changed his life. Now he wants to be able to offer that to the millions of people who, you know, love what he does and care about who he is. And now he's able to connect those dots.
- [95:48]
B
Speaking about the creator economy just for a moment. One thing that I think is fascinating is that I spent some time in the last couple days with the person that was running Feastables. His name is Reed, with Jimmy from Mr.
- [96:00]
A
Beast.
- [96:01]
B
They created Feastables And Reed was running. Now there's a new CEO. But Reed sort of helped Jimmy create it, and they did it together. And they couldn't find a CEO initially, so Reed took the job. And we were talking about Feastables, and in his office, right behind his desk, he has the original Feastable. And we were just sort of joking about Hershey's, and we were looking up the Hershey's market cap. I think hershey's like a $30 billion market cap. And we were sort of laughing at one day, can Feastables ever buy Hershey's? And at some point, the conversation sort of got to Jimmy, to Mr. Beast. And I was like, tell me about his understanding of this industry in chocolate and Reid's. Like, it's deep. There's no one on the planet that knows more about chocolate right now than Jimmy does, that Jimmy knows so much about, like, the ratios of ingredients. And forget the marketing, because Mr. Reese is a genius marketer, but the actual manufacturing of this particular chocolate bar, so it has certain ingredients that he really wants to have in it. And then we talked about Beast Burger that he put out there. And the quality Beast Burger was sort of this, like, Ghost Kitchen type product where on Ubereats you can order a Beast Burger in, like, I don't know, 75 cities in America. But the quality of it, because it was distributed and because they were relying on third parties to actually make them, there was inconsistencies between a Beast burgdord in LA versus Milwaukee. They shut it down. That's a big business to shut down. Like, go back 20 years, talk to some professional corporate business person. Never in a million years they've shut down that business. But they did, because it wasn't the level of care, the level of quality that they demand from their product. That is very different than the days of. I was a kid at the time, but I've heard stories about, like, you know, Brad Pitt launching a toothpaste company at some point in the 80s, apparently. And I don't know who he did a collaboration with, but it was like, basically it was the Brad Pitt, like, putting his logo, his face on some product that, to me was promotional products where, you know, you went to a concert and it was a great concert, and you went to the Merchant booth and you got this shitty T shirt on the back of all the tour dates. Now you go to a Drake concert and you have an OVO which says brand. And a Canada Goose collaboration you can buy. Or Fenty with Rihanna or I was with The Sacred People, which is Beyonce's company, cosmetics company, which is on Shopify. These people that are building these brands that are celebrities or content creators, this is not promotional product. These people really, really care. Skims is another good example. Kylie Cob. There's so many of them that are so authentically connected to Tom Holland, to their story, their care. Tom Holland did not just go to some random brewery and try something insane.
- [98:53]
A
No, no, no. He spent a lot of time.
- [98:55]
B
The packaging is spectacular. So this idea that if you think about like, you know, where business comes from, usually you build a product first and then you go ahead and build an audience. And what is happening right now in sort of creator entrepreneurship land, which I love, is that these are people that have audiences first and they're thinking about the things that they love that their audience might love. And they're building products after they already have an audience. And that is almost swapping of like the sequence of events of how business is built has been swapped. But these are not promotional products. These are not, you know, like one offs that will be gone in a year from now. These companies have staying power and it's really exciting to see that.
- [99:35]
A
They also understand that if the offering isn't authentic to who they are, it's not gonna work. Right. These are people who have built their audiences time and understand what these people want. And audiences can be very unforgiving, right? Like a misstep and they'll let you know. So they're already so finely attuned to that. And to your point about Jimmy and like pulling the burger line off, that speaks to transparency also, right? Like you can't get away with trying to, you know, put something out there that isn't real or is slap shod. Right? Like that will get rooted out and in business shit happens. But. But now there's almost an expectation that you're going to tell the customers like, hey, look, this went wrong, or we made this mistake. And I think people are very forgiving if they feel like there's integrity and honesty in that exchange.
- [100:29]
B
Yeah, I mean, the same way that right now you have sort of this go direct model of transactions where there's no intermediary, you as a brand sell direct to the consumer. I think your communications also have to go direct. I think that for earnings calls now, I mean, I do the CNBC thing, but then I post a video directly on Instagram and on X of me talking to my phone saying, all right, hey everyone, I want to tell you about how we did in the quarter. Here's some of the highlights. Here's what I'm excited about. Even the fact that, like, corporate earnings are being done in that way, I think it's much better. I think it's more authentic. But if you do something wrong, you also have to.
- [101:00]
A
Yeah. I mean, you're a publicly traded company. You got to be pretty judicious in what you say. Don't say, I know. Like, the other day you were taking Canadian businesses to task, saying they need to be more aggressive, and there was like a 4% jump in your stock as a result of that. Like, talking about the power of story. Right. Like, what you say to the media has an impact that reverberates, you know, well across, like, what you might think or whatever. Like, there's.
- [101:27]
B
But it also means for your show, rich, like, for what you're doing here with your podcast, you don't have to ask permission to anyone. The rich role of 10 years ago had to ask permission. You would have had to have a distribution channel that likely was owned by. Not you. This idea that you can actually put out the content you want with the guests you want, with the conversations you want, you can edit the way you want. I mean, in many ways, I think this whole direct thing is actually making more. All of us more entrepreneurial.
- [101:57]
A
Yeah. I never thought I would be an entrepreneur. I still don't even. That feels weird to say that, but I guess I'm running a business. You're a great entrepreneur. It's amazing. Yeah, I've always been the law school safety kind of security guy. This was born out of a very different thing. It came later in life.
- [102:13]
B
But to your point, it's authentic and it's yours.
- [102:15]
A
But the tools are available. That's the thing that removes the middleman and allows you to do things without the capital infusion and all those other things that were barriers previously.
- [102:25]
B
The metaphor that I find fascinating is this mic we're using right here is an SM7B.
- [102:30]
A
Yeah. Very famous mic for a very long time. And this is. It's unchanged for decades.
- [102:35]
B
It's one of the only pieces technology has been unchanged. But there is something different. People like you, like a content creator, a podcaster, didn't have their own Shure SM7BS 10 years ago, used to go to studios to rent Shure SM7BS. I have Shure SM7. I have it at my home office. This is like at my desk when I go on Skype or Zoom or Google Meet, I'm using a Shure SM7B. In many ways, that, to me is like a proxy for what is happening here that, like, we've. We've literally taken the tools that weren't accessible to us and we've brought them in front of us and we're putting out better content, building better products, building bigger businesses, because the SM7Bs now belong to us. And that's the entrepreneurial, that's the technology change that has happened.
- [103:20]
A
I want to switch gears a little bit and talk about mental health. You mentioned issues with anxiety over the years you turned 40. Masogi 29029 you're thinking about, I'm following your footsteps. I'm sure you own your own personal. Except you didn't have to go through some kind of crisis. You just volunteered for it, like, God bless you. But mental health is something that you talk about a lot. Why have you decided to speak about this publicly? And what is it that you want people to understand about the importance of mental health in the context of business or entrepreneurship?
- [103:54]
B
When I was in grade school, a teacher of mine, I think it was in sixth or seventh grade, said to me that people that have depression often look backwards and people that have anxiety often look forwards. And that was the quote. It's a very simple quote.
- [104:08]
A
But are you stuck in the past or are you stuck in the future?
- [104:11]
B
I'm stuck in the future. I'm always in the future. But when I heard that particular teacher say that to me, I was like, that's it. I have anxiety. It was this thing that I didn't know that I had, but I learned about when I was a kid. I was like, I'm constantly thinking about what is next. And so I just kind of had that in my mind. It was sort of a bookmark in my brain for a while. And then at a certain point, I'm like, I don't have to be stuck in the future. Like, I get to decide this on my own. And this is only something I've sort of discovered in the last couple of years, five years or so. I was like, I don't have to be like, anxiety is me projecting something that may not exist, but I get to choose this sort of stuff. And I began to sort of learn about mindfulness and meditation practices. And all those things have been really, really helpful. And I never really talked about it. I always thought that it was a very personal, very vulnerable, just not my style. Like, same way I told you when I cried at the end of Everesting. I was like, why am I crying like this? But as I began to tell more people, hey, and this is in a very personal, you know, very one on one sitting, have anxiety. Here's what's working for me. I find the easiest way, you know, for me to just tone it down is to do very simple box breathing and sort of activates my parasympathetic nervous system. And here's a really good blog post on it. Or here's a good podcast, podcast episode on it. The more that I kind of shared that, the more people sort of got closer to me. People that I weren't necessarily close with began to. We just had a different relationship after the disclosure of my anxiety. And so I began to do it again. I was like, okay, well, you know, sometimes I wake up middle of the night and like my mind is racing like a lot of people have. And someone said to me, like that teacher, this is more recently said, when you wake in the middle of the night, often what happens is your amygdala, your fight or fluoride flight response, part of your brain is activated, but your prefrontal cortex is asleep, so there's no rationality happening. And so for a while, when I wake up middle of the night thinking about something that is never gonna happen, I would just remind myself, I was like, yeah, remember, you're not being rational right now, so go back to sleep. And in the morning, Mr. And Ms. Prefrontal Cortex will be awake and we can have a rational discussion in my own mind about whether or not this is a thing or this is totally ridiculous. And again, I began to share. Hey, I heard this really cool thing about prefrontal cortex and amygdala is being asleep when you wake up in the middle of the night. And people are like, like people that were in their 60s and 70s and 80s who were really thoughtful about this stuff would tell me like, huh, I didn't think about it. I never thought about it in that way. And so I just made a decision a couple years ago to start sharing more about this sort of journey that I do have anxiety. My self identity is not based on anxiety. But when we get into a conversation around mental health, I'll say, you know, I've had anxiety for quite some time and here's what help me and here's what I've discovered. And here are a couple of things that I think about. And I guess one of the better parts of getting older is that I just feel less scared to just say the thing about here's how I'm feeling, or here's the thing that's bothering me right now, or here's the Insecurity at this current moment. And so that's the reason why I've continued to share it. And I find it to be. I've now been able to build sort of this toolbox of tactics of. I mentioned to you earlier that I'm part of this longevity league of these people that really care about longevity. And we do this longevity weekend every year in Muskoka. And it happened a couple weeks ago and I actually brought my mindfulness coach with me and we did a presentation and we talked about this. I know it sounds super cheesy, but sure.
- [107:39]
A
You don't live in la.
- [107:40]
B
I don't live in la. I live in Canada.
- [107:42]
A
It's a very UN Canadian thing.
- [107:43]
B
I know there are a bunch of LA people in this group, but I.
- [107:45]
A
Know some of those Muskoka folks, they're very laughing.
- [107:50]
B
But I brought my coach and I actually explained what this toolbox was. That if I'm about to do something and I'm feeling really anxious and I only have like three minutes, here's a tool that I'll use. It'll probably be a box. Breathing. And if I actually have a little more time, I may do like a full 8 minute or 12 minute sit. And here's what it would look like. And I began to unpack this box and it was remarkable because some of the people in this longevity league are like some of the most unbelievable people in the world. Famous astronauts and artists and business titans, people that. That are way, way more successful than I am. And they came up to me. Some of these guys are like tough guys. Like Harley, that was really great. I'm gonna use some of that stuff. I was like, dude, you're 75 years old. I look up to you in every aspect of your life. There's no way I'm just teaching you that. And it's because I think there was this generation of, in particular business leaders who simply locked that aspect of their life away in a box. And they didn't talk about it with their spouse or their kids or their business partner. It was a sign of weakness. And I think for whatever reason, something has changed that it's now okay to talk about those things and invite people in to participate in what your issues are, because they probably have similar issues.
- [109:02]
A
So many things I want to tease out of that. I mean, first of all, obviously, vulnerability is connective tissue. It makes you feel closer to people and people feel closer to you. Sounds like you've learned that and realize and appreciate that. But to your point about this instinct or compulsion to compartmentalize whatever our dysfunction is and say, well, that's our weakness. And I'm going to put it over here. I think, conversely, and perhaps even more common, especially with high performers, the relationship with that dysfunction is not that it is a weakness, but actually a strength. Right. Like your anxiety is what fueled your drive to be relentless. Or the bond trader who convinces himself that his gambling addiction is actually making him a better trader, or, you know, the heroin addict who thinks they, you know, that's why they're able to write great songs, you know, or whatever it is, it is those mental health issues that we mistake as superpowers because on some level, if we're being honest, they are fuel for what it is that we're trying to create. But. But it's a short term, unsustainable fuel. Right. And you're either going to crash and burn, you're going to, you know, hit the wall with it and realize you're going to have to find a different way. Or it sounds like with you, like you were able to kind of recognize that early enough and course correct and find new and healthier strategies.
- [110:28]
B
And also, I don't want to lose that. I don't want to. I don't want to. I was sort of worried a little.
- [110:33]
A
Bit about if you were completely aquanymous. Are you going to be able to get up in the morning? And this is the dilemma, right?
- [110:39]
B
Correct. So let me share. Something happened this morning, more than I was planning on sharing, but in interest of full disclosure, I woke up this morning. I've seen a ton of your podcasts, some of your interviews, but I had not watched Alex, that you had free solo. And I think that came out last week.
- [110:56]
A
It just came out.
- [110:56]
B
Yeah. Okay. I had not watched it and I was like, I need to watch this right away. Now. It's quite a long podcast and I woke up early, like 3:30 in the morning, which is a little different. I'm still on ESC time zone, but I woke up and I went for a run and then a walk, but I listened to the entire episode, partially. I was interested in it. I think he's a super fascinating guy. But also I didn't feel right about coming on your show today without having heard your most recent podcast, because I think that's like, you are the best at what you do. And this incredible opportunity for me to come on your show is an honor for me and I take those things very seriously. That instinct to listen to your most recent episode before I showed up here today may have been Partially driven and sourced through anxiety. I don't really care. It did something really great for me. I now I believe I had, when I walked in the door today, the most current version of how you were seeing the world. Because. And again, ironically, it may have been filmed six months ago. I didn't know that, but I felt that I owed it to myself, to you, but mostly to myself, to know what is Rich's most current version of the world, his most current perspectives on things. And there was no way that I was gonna walk in here today without having listened to that. That matters. And that's where I think anxiety is a fucking superpower.
- [112:21]
A
But that choice can be generated from something else other than anxiety.
- [112:24]
B
Could be. But for me, it's anxiety. And so I'm not gonna say like, I wish I would have slept in longer. No, that happened. When I go on Kramer, Squat Box or Mad Money and I know he's gonna ask me some random metric about, I don't know, contribution margin of some particular area of our business. The reason I know it is because of anxiety. I don't think that's necessarily a bad thing. I think it could. It's not getting the better of me. I wasn't going to wake up at midnight or something and not sleep last night because I wanted to listen to Alex's episode. I woke up at a time where I probably would have woken up around that time anyway. But I focus on it because I thought it was very important. I wish it wasn't only anxiety based. But if that's the reason that I'm able to be good at the things that I do or better things I do that I wouldn't otherwise, I'll take it.
- [113:15]
A
Yeah, I suppose if it's working for you and not against you on some level, but understanding where you are on that spectrum. Because if you. You're so anxious about what's happening tomorrow that you can't be present with your family or that kind of stuff, that's not okay.
- [113:30]
B
So there is, again, there is a threshold to this, which is that is it actually making my life better or worse? And for the most part, I've been able to channel it in a way that I think it makes my life better. But there are times where I will say to Lindsay, I'll say to my wife, I know we're at dinner right now. I don't want to be that husband who's staring at his phone the whole time, but I'm dealing with something right now, like on the business. I need to take care of this. And Lindsey has said to me, like, she much prefers me to say that than to pretend like I'm present with her when I'm not. And so I'll say, give me 10 minutes. Time me if you want. I'm gonna go outside the restaurant. And, Lindsay, if you want to leave, like, you don't wanna sit here by yourself, no problem. But I need 10 minutes. And Lindsay's like, no problem. Take 10 minutes. But when you come back here, we're on date night, right? And I was like, yeah, we are. And I'll come back and I'll turn my phone off and I'll put it away. So even that type of thing, 24 months ago, I would not have done that. I would have pretended that I can do it all.
- [114:23]
A
So what changed? Is it this mystical 40?
- [114:28]
B
I don't know, 40? Yeah. No, it's not mystical. I think 40 is just a bookmark in your life. And it's like, okay, how much more time do I have? When my kids are young, in the early days of having kids, my kids would come into our bedroom, to our bed every night. And I used to wake up and be like, I just want a good night's sleep. And now they're coming to our bed less and less. And every now and then, I kind of miss them coming to our bed at nights, snuggling up and waking up with our two daughters in the bed. I don't know. Maybe it's just getting older. Maybe it's meeting more people who explain to me people that I thought I admire back to that vertical mentors that I really admire in one particular area. When I say to them, what's something that I don't know that I should know about your. And they'll say, I didn't do date nights. I wish I did. And so I think, yeah, having more of those people in my life, plus just getting older, dropping a little bit of the ego. It's a very helpful mechanism.
- [115:27]
A
Yeah, you're at where you're at. You've been there for a while. So how can you take this intense intentionality that you have devoted to your business, to the other areas of your life that are important? Right?
- [115:38]
B
Yeah.
- [115:39]
A
Because, listen, you've scaled a huge mountain. There's always more mountains to climb. But what is that really gonna do for me?
- [115:45]
B
And I wanna enjoy this mountain for a moment. Right. The flip side of the anxiety, sort of as superpower, is that there's also this consistent, perpetual. Not dissatisfaction, but, like, neutral satisfaction that, like, okay, I'm Here, what's next? And that goes back to the topic of even enough. Am I doing enough? Do I have enough? Do I feel like I am enough? I haven't figured it out yet, but at least now I have language for it. And I think naming things back to the sort of founder mode thing, I think this idea of having language for this to be like, oh, this is me just playing this enough game. I'll never have enough. A lot of entrepreneurs that I've met that are very successful, they talk about their magic number of how much money they've made.
- [116:23]
A
Yeah. But when they get it, they never retire.
- [116:26]
B
Literally zero. I have great mentors I've had over my life, dozens of incredible people. Not a single one one of them has said, I hit my magic number and I was good. So having a magic number is totally stupid. Because if someone that I interviewed, I have this podcast called Big Shot where I created an archive of Jewish entrepreneurs, and most of them are quite in their 70s, 80s and 90s. I interviewed Izzy Sharp, who created the Four Seasons recently, and I asked him about when did he know that he made it? He created the Four Seasons Hotel. So the Four Seasons is amazing for two reasons. One, it's, I think, one of the nicest hotels on the planet. But two, the business model is very unique because the real estate is owned privately, but the services inside the actual staff is owned by the Four Seasons. So he not only created the Four Seasons hotel chain, but he also created a brand new business model.
- [117:18]
A
A novel model.
- [117:18]
B
A very novel model. And Four Seasons is incredibly successful everywhere they are. And I asked Izzy, when do you know you made it? Izzy's 93 years old. And he said, I still don't know. And in that moment, I felt two things. One, wow, what an amazing thing to say. He's Izzy Sharp, storied entrepreneur. And I put Four Seasons in the same class as Apple from a brand perspective. But also, I'm not sure I want to say that when I'm 93, it's sort of sad.
- [117:52]
A
What is making it mean and what is driving the desire to make it however you define that. Right. And I think, I think if you're mission based and that mission is tied to serving people and making the world a better place, and that mission has no end. Like, there will never be a destination where all the work is complete. There's something beautiful and laudable about that, to devote your time and your energy and your life to something like that. But if making it or just climbing this endless mountain is about filling this Hole in your spirit because you're detached from anything more meaningful in your life. Like, you're gonna end up alone and sad, Right? So what are you chasing? And on some level, it's back to story. Like, what are you doing? Like, what is this thing that you're spending all your time? What is it for? Right? What are you chasing? And getting really clear on that. On some level, like, we're all victims of our ego, living in the material world, like, chasing shiny things and running around, like, with our heads cut off. But on some level, clearly what comes across with you is you're on a mission. And that mission is very important. And you have a lot of clarity around what that means. Where's the caution around not getting caught in that trap.
- [119:15]
B
That's right. And there's this fine tension because the people that are most successful, sort of, in my view of that, a lot of them are hard driving, it's never enough type people. So the benefit that I have is I'm 50 years younger than some of these people that I'm interviewing for Big Shot. And I can learn from their successes, but I can also learn from their mistakes. And I like. There's this great sort of. There's a guy named Alexander Chalmers who wrote a book in, I think it was 1700s Scottish guy. And it was about the secret to life, secret to happiness. It was very simple. I remember this, like, I don't have any tattoos, but this would probably be the tattoo that I would get, which is like, someone to love, something to do, and something to look forward to. And whenever I'm sort of struggling, I always sort of go back to this thing. It's like, someone to love. Like, I'm deeply and madly in love with my wife and my children. The thing that I do 90% of my time is help build this great company that is deeply personal to me. Check. And someone to look forward to. I always try to find something. Like, I've been on the road for the last couple weeks, and I'm going home on Friday back to Camp Canada, and I'm just like, I know exactly what I want to do Friday night. There's a particular bottle of wine that I want to drink with my wife in a particular room in our house, and we're going to watch a particular movie. And I'm really looking forward to that. It's not like some major trip or some big event. It's just, I'm really looking forward to Friday night, going home and having this evening with Lindsay. And I just kind of keep Going back to that, like, it's so simple. Something to do, something to love and something to look forward to. It's. It's just if you have that, you kind of have it all.
- [120:50]
A
I believe you. I believe what you just said. But I also think this. Are you ready for this?
- [120:57]
B
Let's go.
- [120:58]
A
I bet you're terrible at vacations.
- [121:00]
B
Terrible at vacations? Yeah, terrible at vacations.
- [121:03]
A
You can't turn it off, can you?
- [121:04]
B
No. But on vacations, what I realize is that I'm actually really good at like one week vacations. I'm really bad at two week vacations. So what does that mean? It means that I really love. My weekends are really fun. I really enjoy my weekends. I work a little bit in the morning, Saturday morning and Sunday morning. But generally I try not to do any deep work on the weekends. I have two young kids, I want to spend time with them. So my weekends are sort of friends of mine want to take larger trips, three week. And I was like, I cannot do that right now. I don't think I have the. I don't think I.
- [121:34]
A
But let's say, just as a thought experiment, let's say you could trust and have confidence that whatever obligations that you're responsible for are being taken care of. Let's assume that everything is fine at Shopify and you have these three weeks and you've got buddies they want to do they want to ride mountain bikes across Vietnam or something, whatever, right. You have an opportunity to do this. Do you feel the anxiety?
- [122:03]
B
Yes.
- [122:04]
A
Right. So the question then becomes like I.
- [122:07]
B
Can lie and say, yeah, I don't.
- [122:08]
A
Know what's behind that. Like, what is the discomfort hurt with sitting still with yourself? Right. And I think that's the teacher, right? If you can go. I'm saying this is somebody who has the same, you know, I have the same thing. How are you of occasions? A lot better. Yeah, but I'm older, you know, I'm older than you. But yeah, like, oh, I need to be busy. I need to be doing things all the time. I don't know what to do with myself if I'm not like there's something so something vacation.
- [122:35]
B
Like one thing that works examine. My favorite beach in the world is Turks and Caicos. I just think it's beautiful beach. It's really lovely. I get together my family every year and when I'm there I try to like, you know, first couple days I'll sit around the beach and play and then I'll go take a kite boarding lesson or I'll go take my daughter kayaking. And so I'm finding things now that, like, I want to be more present. And so I now realize, actually I'm more of an activity kind of guy. I can't just sit on a beach endlessly and listen to, like, music. I'll go for a long walk with my wife and we'll have a great conversation. Or I'll run on the beach by myself and listen to a podcast. But I'm beginning to rather than pretend. And that's, I think, what I used to do. I think the old version pretended to be good at vacation. I'm not. Okay, so let's figure out a way to, like, at least for now, to create vacations where I can be present and also be self aware. To say, like, ask myself those questions. Why can't I just sit on the beach? What is preventing that from happening? And I don't have that answer. But I'm. For the first time in my life, I'm asking those questions. I never did that. Like, I would never ask those questions before.
- [123:41]
A
So if Lindsay, your wife, was sitting across from me right now, and I asked her, like, what is Harley's major malfunction? Or like, what is the thing that comes up in your marriage that is the biggest challenge for her?
- [123:51]
B
She would say, I can't sit still. And sometimes that affects her.
- [123:54]
A
Yeah. Yeah, that's what I thought.
- [123:55]
B
Yeah.
- [123:56]
A
It's that same thing. Like, well, that's the same energy that makes me successful. You don't get one without the other. You can't have it both ways, right?
- [124:05]
B
I don't know. I'd like to try.
- [124:07]
A
Yeah. So I'm not saying I have an answer to that, but I just think it's interesting and worth investigating.
- [124:12]
B
What has happened to you that has actually created the most amount of self tolerance to allow you to do a vacation? Has there been something that, other than just sort of.
- [124:21]
A
Well, all of these things for me are the result of doing it the wrong way for so long that it creates sufficient amount of chaos and pain that I'm forced to do something different. I took a month off for the first time right before the pandemic because I was teetering on burnout, you know, and I was incredibly, just like sort of uncomfortable in that. And now I do it proactively every year as like a prophylactic. Like, it's built into my year. And every year that I do it, I untether a little bit more. Like, you know, at first I was like, I was still checking my email all the time. Or like, the last time that I did it, which was almost a year ago, like, I didn't look at my email once and, like, everything was. It was great, great, you know, so I'm learning, like, I'm not perfect at this. And I mean, this is a very privileged, you know, thing, right? Like, I recognize that, but the point being, like, finding a way to have a relationship with yourself outside of the context of what you do so that your identity is not so, you know, completely embedded in, you know, like, Shopify President, right? There is a Harley outside of that that is worthy of honoring.
- [125:30]
B
There is this. Back to law school friends. I met with a law school classmate of mine a couple years ago, probably five years ago, and he was just about to come partner at a big law firm, like a big white shoot law firm with all the accoutrements and all the things that comes with it. And we were talking about something and he's like, oh, yeah, well, Sunday night. I was like, Sunday night? He's like, yeah, well, that's the worst time of the week. I was like, what do you mean? He's like, I hate Sunday nights. I was like, why? He's like, because Monday's coming the next day. And I'm like, huh? Anyways, let it go. Didn't think much about it. I called him back a couple weeks later. This is probably five years old now, five years ago at this point. And I called him back. I was like, you know, thinking about your comment about Sunday nights, and I know there's like these sort of memes around Sunday scaries. But part of the reason that I don't. I don't know if I don't love vacations or don't need vacations or struggle with it a little bit is because. Because my Sunday night feels like my Friday nights.
- [126:23]
A
That's a gift, though. That's not.
- [126:25]
B
Most people say, and I acknowledge that. I actually acknowledge the fact that that is incredible privilege. That my Saturday morning, that feeling, Saturday morning. I feel like that Monday mornings, too. Not all the time. Sometimes I can have a bad day or something like that, but generally that's how I feel. And I think that privilege comes with a great amount of responsibility. And I feel that responsibility now. The key for me is not to mistake responsibility with avoidance of some issue I'm not dealing with. I'm not at that stage of evolution. I'll come back in five years on that one. At some point, I'll report back of how I'm doing.
- [126:56]
A
Well, before we kind of close this down. Maybe we can end this with a few thoughts around what you've learned in your journey of entrepreneurship that are relevant to I don't run an entrepreneur podcast. This is not a business podcast. Most people listening to this, maybe a bunch of them have side hustles or they're shopify clients, but most of them probably aren't entrepreneurs. So how is this relevant to the average everyday person who's tuning in, looking for a little insight on how to level up their life a little bit?
- [127:30]
B
We talked a little bit about this idea of the thing you already do, that you do personally, could be the thing you also do professionally. So I think we've covered that. This idea that if you make the greatest minestrone soup for your family, imagine you started a minestrone soup company company. The example I'm going to give you though, is fascinating. So I mentioned this sort of tea company. So my best friend David, who's the king of tea, not just in North America, on a global scale, he has built the largest tea company of the last couple of decades. He left David's tea after the IPO. So in 2016, he left a year after the IPO. And as he was thinking about what he wanted to do next, remember this is like the tea guy. He constantly was bringing me tea. He was constantly talking about tea, but he himself didn't actually realize that that his next thing should also be tea related. The reason I bring up this particular story about David is because if the king of tea, his name on Instagram is literally Tea Maverick, it's all he talks about. If he himself is somewhat blind to the thing that's in front of him, that I had to give him a kick in the butt to say, dude, you gotta start another tea company. This is like your thing. It tells me that so many people have something in front of them that they simply are not acknowledging that could be their thing. And so the first thing I'll say to you is for those listening that want to start a business, likely the business that you're going to start that you will be most successful at is right in front of you. And it may be literally staring you in the face right now on your desk, you know, on your walk right now. So one like look around, figure out what that is. The second thing is this imposter syndrome of entrepreneurship. It's only in your own head head. Almost every merchant on Shopify that has started on the platform at their mom's kitchen table that has made a billion dollars, still says that they're still trying to figure it out. That there is this assumption or presumption, I should say, that at a certain level of success, you have to figure it out. One of the greatest aha. Moments I've had through these interviews, through Big Shot, that has been so comforting to me is even the most successful entrepreneurs in the planet that I've met are still trying to figure it out. They still don't know exactly what they're doing, but they've gotten better at being okay with that. That true confidence isn't actually knowing what to do. It's knowing that whatever comes your way, you'll be able to figure it out. Second thing, the third thing is back to the cost of failure. Like, it is scary to start a business. It is very scary to put yourself out there. It is very scary to fail. The cool part is the safety net right now for most people listening most of the time, especially like, you know, in this part of the world, is you start something that doesn't work, and so you pivot and try something different. And a lot of the companies that you admire, it didn't just start with. Didn't just start with Shopify. It was first a snowboard shop. And it didn't start with Slack. It was a gaming company. And it didn't start with, like, you know, Supreme. Started as, like, a single, like, deck, like a skateboard deck. And I think that there is this thing we do to ourselves that I'm still doing at this stage, but I can do as I say, not as I do. You just get over that and try and put it out there and see what happens. And then in terms of your concern about how do I compete with those incumbents that are out there, those incumbents cannot do what you can do. Those incumbents cannot write personal letters to the first 10 customers because they have to do everything that scales, and they can't learn the birthdays of the people that are buying from them. So they can send a little email saying, I think it's your birthday today. Happy birthday. If you were thinking of starting a business, those are things that I would think about today, and I'd love to help in any way I can. I pray at the altar of entrepreneurship. Shopify prays the altar of entrepreneurship. And we want more of those to exist in the world.
- [131:13]
A
Yeah. That was awesome, man. Thank you.
- [131:16]
B
Thank you.
- [131:17]
A
I really appreciate you coming here to share today.
- [131:18]
B
Thanks for having me on screen, Honor.
- [131:19]
A
Yeah, I love the mission that you're on. You know, the demon democratization of all of this, like, making these tools accessible for just everyday, average folks to, you know, create something unique and special. Like, I think it's awesome.
- [131:33]
B
Yeah. And despite you not thinking you're an entrepreneur, you're an incredible entrepreneur. And this is really fun.
- [131:39]
A
Yeah. Thanks, man. We did it. How do you feel? You feel good?
- [131:42]
B
It's great. Yeah. I can do this all day.
- [131:43]
A
Cool.
- [131:44]
B
Keep going.
- [131:44]
A
Well, come on back.
- [131:45]
B
I'd love to.
- [131:46]
A
Yeah.
- [131:46]
B
With less anxiety. Yeah. Yeah. Good.
- [131:58]
A
We're brought to you today by Eight Sleep. Head to Eight Sleep.com richroll and use code richroll at checkout to get $350 off the Pod 4 Ultra. That's Eight Sleep E I G H T sleep.com that's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guest, including links and resources related to everything discussed today, visit the episode page@richroll.com where you can find the entire podcast archive, my books Finding Ultra Voicing Channel Change in the Plant Power Way, as well as the Plant Power meal planner@meals.richroll.com if you'd like to support the podcast, the easiest and most impactful thing you can do is to subscribe to the show on Apple Podcasts, on Spotify and on YouTube and leave a review and or comment. This show just wouldn't be possible without the help of our amazing sponsors who keep this podcast running wild and free. To check out all their amazing offers, head to richroll.com sponsors and sharing the show or your favorite episode with friends or on social media is of course, awesome and very helpful. And finally, for podcast updates, special offers on books, the meal planner and other subjects, please subscribe to our newsletter, which you can find on the footer of any page@richroll.com Today's show was produced and engineered by Jason Cameolo. The video edition of the podcast was created by Blake Curtis with assistance by our creative director, Dan Drake. Portraits by Davey Greenberg, graphic and social media assets courtesy of Daniel Solis. And thank you, Georgia Whaley for copywriting and website management. And of course, our theme music was created by Tyler Pyatt, Trapper Pyatt and Harry Mathis. Appreciate the love, love the support. See you back here soon. Peace Plants. Namaste.