Harley Finkelstein: You Must Requalify for Your Role, Every Year

Shopify’s Harley Finkelstein reveals the one standard that actually scales your career and your family. Harley shares why stepping down as COO was his hardest choice, the family motto that guides his daughters, and what makes someone good at storytelling. They discuss AI's real advantage, the calendar system that keeps him accountable, and how he maintains high standards. If this gives you one standard to raise your team—or your family—share it with a friend who needs to hear it today. ------------ About Harley: Harley Finkelstein is the President of Shopify. He leads storytelling, external relations, and company energy—translating world-class product into world-class adoption. Approximate timestamps: (00:02:10) Living With Unreasonably High Standards (00:03:40) Generational Trauma and Family Relationships (00:07:52) Growing Up With Adverse Circumstances (00:14:42) Prioritizing In Life And Becoming World Class (00:24:45) Requalifying For Your Job (00:30:05) Mindset for Professional Growth and Success (00:31:33) How To Find A Great Business Partner (00:32:57) Switching From COO Of Shopify To President/Chief Storyteller (00:40:34) How Storytelling Impacts Shopify (00:42:00) How To Get Better At Storytelling (00:46:13) Shopify And How Commerce Has Evolved (00:49:27) Forced Entrepreneurship Vs Passion-Based Entrepreneurship (00:51:34) Mentorship (00:59:41) Overcoming Failure And Rejection (01:02:46) Out Caring Is More Important Than IQ, EQ, Raw Talent (01:06:07) Parenting And Teaching A Hardwork Ethic (01:11:23) Teaching Resilience Thanks to our sponsor for supporting this episode: SHOPIFY: Sign up for your one-dollar-per-month trial period at shopify.com/knowledgeproject MINT MOBILE: Get your 3-month Unlimited wireless plan for just 15 bucks a month at mintmobile.com/knowledgeproject Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠ Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠ and get your own private feed. Watch on YouTube: ⁠⁠⁠⁠⁠@tkppodcast Follow Shane Parrish X ⁠⁠⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠⁠⁠ Insta ⁠⁠@farnamstreet⁠⁠ LinkedIn ⁠⁠Shane Parrish⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  It completely changed my energy levels. It made me exothermic again. It made me excited again. It made me want to recommit year after year after year to Shopify and to Toby and to this mission that we're on.

• 0:12Shane Parrish?

  Go a little deeper on your father and how that's impacted you and what that relationship was like.

• 0:18Speaker 00

  At 17 years old, the rug got pulled from me and I was forced to basically grow up overnight. Ultimately, if you think about the mission of Shopify, it's we want to create more entrepreneurs. We want to make entrepreneurship more accessible, but we think that entrepreneurship allows anyone to do that. It's the great equalizer. The way that I think I had the most amount of value to Shopify is the same thing that I want to be world class at, which is.

• 0:48Shane Parrish?

  I want to start with what areas of your life do you think you have what other people would consider unreasonably high standards?

• 1:01Speaker 00

  Maybe start with, I mean professionally, I think I am, I'm pretty hard on myself in terms of achievement. Years ago, I read something about the concept of abundance versus scarcity mindsets. And I think generally I do not have an abundance mindset about the things in my life. Some of that may be, I don't know, this is going deep in the first minute, but some of them might just be like multi-generational trauma, which I actually believe in. I think I carry some of the weight of my grandparents, Holocaust survivors, the weight of my father who struggled his whole life financially. But I think the way it manifests most is probably with my own career that I

• 1:46Speaker 00

  don't, I still don't think I'm doing enough, that I have enough, that I am enough. And that's probably the largest area where I think I have very high standards. Maybe the second one is just I have very high standards for relationships. I think that the friendships that I have, I hold very dearly to in my life. And because I hold them dearly, I hold them up to a very high caliber of quality.

• 2:12Speaker 00

  And sometimes that disappoints people, sometimes that means those people disappoint me.

• 2:17Speaker 00

  Those are probably the two major ones.

• 2:19Shane Parrish?

  Go a little deeper on your father and how that's impacted you and what that relationship was like.

• 2:25Speaker 00

  My dad is an immigrant to, we're sitting here in Montreal, he immigrated here in the 50s. His parents were Holocaust survivors. After the Holocaust, they were in the concentration camps, they survived. They went to Hungary, to a town called Debretson. And during the Hungarian Revolution, things are really bad for everyone, but especially for Jews. Canada had this amazing program where they let 40,000 Hungarian immigrants come to Canada in the revolution. So actually, in Canada, if you meet Hungarians, generally they came in 56. Because this sort of cohort of Hungarians came in the 50s, they all came by boat. And my dad, when they got here, they didn't have any money, they had no, didn't know anyone here, they certainly didn't have any education.

• 3:10Speaker 00

  So my grandfather ended up selling eggs at a local farmer's market not too far from here called the Jean-Teloff farmer's market. And he created this egg stand, he called it Le Capitaine, it still stands there today, my uncle runs it. It's been around for, I don't know, 75 years, something like that. And I think my dad was always very ambitious. He was, he had that sort of, that immigrant ambition, he wanted to, he wanted to have a better life than his parents had, and he wanted his children to have a better life than he had. And growing up, he always sort of made us feel like we had, we had enough. There was never sort of a sense of scarcity in the, in the house whatsoever.

• 3:52Speaker 00

  It was only later in life that I realized that, that it was a bit of a fugazi, it was fake. That we really didn't have very much, but at the time, I didn't know that, it felt like I had enough. And where things came to a head, and you know, you and I have been friends for a long time, so you know the story, was when I was 17, my dad was arrested, I went to prison. And that was sort of the first time that I saw.

• 4:19Speaker 00

  True vulnerability, that's where it all sort of, the facade of a secure foundation came crumbling down for me. I just moved, we were living in South Florida. I just moved to Montreal here. It was 2001 to go to McGill. Mom calls and says dad's been arrested. He was arrested for white collar crimes and for business crimes. And

• 4:47Speaker 00

  I was I was mad at him. I was disappointed at him. I was too young to fully have the maturity to know what this all meant.

• 4:59Speaker 00

  And I think a lot of people talk about, you know, how trauma in their lives dictate the rest of their lives. I think the moment, actually, there's, um, there's an apartment not too far from here on the corner of Dr. Penfield and Peel. Uh, there's an apartment in that building. Uh, I think it's apartment 405. Where there's probably not there anymore, but there is a, there was a hole in the wall. Where after my mother called me to tell me my dad was arrested, I took the phone and threw it against the wall and, and, and, and dented the wall. We can sort of get into what happened after that, but if you sort of fast forward today, um, my dad's back in my life. I have a great relationship with him. I think like a lot of people that are of my vintage, I'm 41. You do begin around this stage of life to

• 5:45Speaker 00

  have this epiphany, or at least this realization that like the relationship of parent and child flips a little bit. In some ways, I feel like I'm sort of the parent to my, to my parents now. I wasn't ready for that. That sort of came out of nowhere. My parents turned 70 and it just, something's been changed. But my relationship with my dad is, is, is, it's loving and I have deep admiration for the life he's given me. But certainly, I think some of the trauma he sustained from being an immigrant, from being the child of Holocaust survivors. I've adopted that through his experiences, but also through the fact that at seventeen years old, the rug got pulled from me and I was forced to basically grow up overnight.

• 6:30Shane Parrish?

  Was that the moment where your standards for yourself changed? Because I guess what I'm getting into is like so often we're born into a situation, a household, we're surrounded by people. We don't choose, you know, we don't choose our parents, we don't choose our zip code, we don't choose concentration camps or anything like that. We're put in these situations and we adopt the standards of the people, the mindset of the people that we're in. And then there's like another level to it, often for a lot of us. If we're not born into a situation where a parent has a high standard for themselves, then we don't adopt that ourselves. And I think a lot of entrepreneurs share this constant, I can be doing more, I can be doing better.

• 7:14Shane Parrish?

  There's a gap between where I perceive I could be and where I am.

• 7:18Speaker 00

  I remember we moved to South Florida in nineteen ninety-six or ninety-five or so. I was around twelve years old. The area we moved into, it was in Boca Raton, Florida, in Palm Beach County. Boca is well-known as being a fairly wealthy area, but we were not wealthy. I mean, again, when we lived in Montreal, I didn't experience any, there was always food on my table. I always felt like, you know, I didn't always have all the stuff that I wanted, the, you know, the Air Jordans, but I had one pair of Air Jordans. And so I didn't, I didn't live a life of, where I didn't have enough growing up. But I remember moving to South Florida and that was the first time, I think, that I realized that other people have a lot more than I did.

• 8:02Speaker 00

  There were gated communities everywhere, but we didn't live in one. There were incredible private schools everywhere, but I couldn't attend one because it was too expensive. It was sort of in that age group, in that sort of range where I began to realize that my father wanted to have a better life than he did. That he was, he wasn't living in a community where we were the average or we were above average. We were living in a community where we were below average. I remember asking my parents why I couldn't go to private school. There were these beautiful private schools all over Boca Raton, with these big, beautiful gates and these wonderful buildings. And I remember asking my parents, why can't I go to Pine Crest or St. Andrews, which were the two big schools? And my mom said, we can't afford it.

• 8:45Speaker 00

  It was like $30,000 a year, which was an insane amount of money for my parents at that point. And I think that's actually around when I began to get my first chip on my shoulder. Something didn't sit fully well with me. And, and I think the way it manifested was ambition, competitiveness, some insecurity. I mean, there I was, going to a public high school in South Florida. I was a, you know, I was a short Jewish kid from Montreal, Canada, moved to South Florida, had no friends or family. There were 4,000 students at the school. And there were students from all different backgrounds. Some lived in Boca, some were being bused in from Delray, a much lower, lower income community.

• 9:27Speaker 00

  There were police officers, because that's what you had in big American public high schools. And I was scared shitless. I don't know sort of what, what drove me then, but like, within a year, I was like president of student council, I was wrestling varsity, because I figured out actually one of the advantages of being short and kind of stocky was, was a pretty good wrestler. And so I was able to change my circumstances by sheer will at that point. The second thing that happened around that same period of time was that, I really, I was 13, and as, as, as you've heard before, you heard me talk about, all 13-year-old Jewish kids go to a lot of bar mitzvahs, almost every weekend.

• 10:11Speaker 00

  And I was enamored by DJs. I thought these DJs at these bar mitzvahs were like magicians. And I really thought these were the coolest people I'd ever seen. And although my dad didn't have a lot of money, the one thing he did do, and he's done this my whole life, was anytime I had an idea that I shared with my father, he would say, "Great idea." He actually, there would be a physical manifestation of that, which was that he would make me these business cards. And tonight, you and I are having dinner at my home, and I will go to my home office, and I will show you those early business cards. But I still have them lined up in my office. Every time I had a silly idea about a business, my father would come home with a business card that said my name and the business name. And it was this very simple, physical

• 10:56Speaker 00

  device that was the equivalent of him saying, "You absolutely can do this. You have the capacity, you have the willpower, you have the entitlement, you can do this, you have the permission to go do this." And I ended up DJing 500 bar mitzvahs after that, started my own DJ company, hired myself. And that was sort of my relationship with my, I think, with my dad over my life, which is that I don't think I fully understood the baggage he was carrying with him his whole life. But he was unequivocally supportive and loving of me. And even when, years later, when he went away and we lost all our money, it was

• 11:38Speaker 00

  tough for me to hate him, because ultimately, what I really believed was, he was doing it for me. That he was going, he was taking massive risks with his own life and his own freedom, in order to give me and my too much younger, one of my sisters is 10 years younger, the other is three years younger. He was doing it to give me and my siblings a much better life. And he was willing to risk what ended up being five or six years of federal prison time to provide that for us. And as I sort of reflect on my upbringing and my childhood, it'd be difficult for me not to credit

• 12:16Speaker 00

  His transfer of confidence to me with kind of how I ended up. So I have anxiety now. I am constantly trying to do more, feel more, build more, have more. That feeling of scarcity is in me. There's a bunch of negative externalities have come with that. But the other thing that came with it is what I believe to be an incredible amount of ambition. And that ambition and that energy, you and I have a lot of mutual friends and I think most of our mutual friends would describe me as someone that is constantly high energy. That high energy mostly comes from a place of joie de vivre and excitement.

• 13:01Speaker 00

  And I heard this great quote that part of being happy is being excited by all the elements of your life. I'm excited by all the elements of my life. And I think that while I probably have a complicated relationship with my dad,

• 13:16Speaker 00

  I am here and I have this life partially because of him.

• 13:21Shane Parrish?

  Thank you for sharing that.

• 13:24Shane Parrish?

  You know what doesn't belong in your summer plans? Getting burned by your old wireless bill. While you're locking in itineraries, your wireless bill should be the last thing holding you back. That's why I recommend the switch to Mint Mobile. No gimmicks, just a smarter play most people overlook. You make smart trade offs everywhere else in life. Why not here? All plans come with a high speed data and unlimited talk and text delivered on the nation's largest 5G network. Use your own phone with any Mint Mobile plan and bring your phone number along with all your existing contacts. It's a small switch that compounds over time, just like any great decision. Most people leave money on the table. This is how you stop doing that. If I had needed this product, it's what I'd use. The savings are unbeatable.

• 14:10Shane Parrish?

  This year, skip breaking a sweat and breaking the bank. Get this new customer offer and your three month unlimited wireless plan for 15 bucks a month at mintmobile.com/knowledgeproject. That's mintmobile.com/knowledgeproject. Upfront payment of $45 required, equivalent to $15 a month. Limited time new customer offer for first three months only. Speeds may vary, about 35 gigabytes on unlimited plan. Taxes and fees extra. See Mint Mobile for details. You know, people talk a lot about product market fit, sales tactics, or pricing strategy. The truth is, success in selling often comes down to something much simpler: the system behind the sale. That's why I use and love Shop Pay, because nobody does selling better than Shopify.

• 14:55Shane Parrish?

  They've built the number one checkout on the planet, and with Shop Pay, businesses see up to 50% higher conversions. That's not a rounding error, that's a game changer. Attention is scarce. Shopify helps you capture it and convert it. If you're building a serious business, your commerce platform needs to meet your customers wherever they are: on your site, in-store, in their feed, or right inside their inbox. The less they think, the more they buy. Businesses that sell more, sell on Shopify. If you're serious about selling, the tech behind the scenes matters as much as the product. Upgrade your business and get the same checkout that I use. Sign up for your $1 per month trial period at Shopify.com/knowledgeproject, all lowercase.

• 15:39Shane Parrish?

  Go to Shopify.com/knowledgeproject, upgrade your selling today. Shopify.com/knowledgeproject.

• 15:49Shane Parrish?

  Going into all the elements of your life, I know you're very selective about the things that you take on and the things that you do and you say no to a lot. I want to explore that a little bit. What do you want to be world class at? And so what are the key elements of your life that you're pushing on?

• 16:08Speaker 00

  I am not a generalist. I've never been a generalist. If you were to ask Lindsay, if you'd ask my wife, in fact, if you were to ask my eight-year-old daughter Bailey or my six-year-old daughter Zoe what our family motto is, they'd all tell you the exact same thing. It is, "How you do anything is how you do everything." That is our family motto, which frankly, it means, because they're six and eight, means it's my family motto, and I've just sort of told them that's their family motto, and they've adopted wholesale. Eventually, they'll be old enough to decide whether it's for them or not, but... That motto, certainly for me and Lindsay, my wife, it describes our life. There is an intentionality about everything that we do in our lives.

• 16:47Speaker 00

  The way that I think about leading this incredible company with my team Shopify, to the way Lindsay thinks about cooking dinner, to the wine that I've been thinking about you and I are gonna drink later tonight. There's a great intentionality about all these things, and I think that makes life fun and interesting. But what I've come to realize, this is my 16th year at Shopify. I'm 41, so I've been here for not quite half my life, but almost.

• 17:20Speaker 00

  The way that I think I had the most amount of value to Shopify is the same thing that I want to be world-class at, which is I want to be a great storyteller. I don't think I'm there yet. I've met truly world-class storytellers. We can sort of get into some of those later on. I'm not there yet, but that is the thing I want to be the best at. I love playing tennis. I don't think I'm ever gonna be a world-class tennis player. I love to ski. Don't think I'm ever gonna be a world-class skier. There are things in my life, like DJ, I don't think I'm ever gonna be world-class. There are things I do in my life that are fun, that are strictly for enjoyment, and I enjoy the craft of it. But storytelling in particular is something that, when I look at all the different things I've done at Shopify, it's a thing that I think has added the most amount of value to the company. And this also speaks to my dynamic, this yin and yang dynamic that I have with Toby,

• 18:04Speaker 00

  which is that I've sort of always, in hindsight now, I can sort of see this, but I've always sort of viewed my role as he is the greatest product person I've ever met in my life. He's this incredible tech visionary, especially when it comes to commerce. And my job has kind of always been to take the brilliant things he's built and tell the world about it. Tell investors, tell the media, tell our merchants, tell partners. And it gives me great joy. I love doing it. It's that, you know, when your Saturday morning feels like your Monday morning, you know you're on to something really great, which is sort of the opposite of, you know, what people describe as like Sunday scaries, which I've never felt my whole life, but I know people do find that to be a real thing.

• 18:47Speaker 00

  It's storytelling.

• 18:48Shane Parrish?

  I love that. And you also want to be a world-class father and husband.

• 18:53Speaker 00

  Those are harder things. Very difficult to ping the satellite and get a ping back to know whether or not that's actually happening. With storytelling, I can get third-party, objective feedback. Being a world-class father and husband, it's more difficult to track that. But those are things that are very important to me. It is very important to me that my kids believe that I'm a world-class father and my wife thinks I'm a world-class husband. And that comes actually less natural to me than storytelling. Storytelling is sort of my ground state. It's the thing that I would do if, if, you know, if I didn't have anything else to do and I was left to my own devices.

• 19:37Speaker 00

  I would tell stories. I like telling stories. Being a great husband often means doing things that are unnatural. A simple example that I think a lot of us fall into the trap of seems to be more of a,

• 19:50Speaker 00

  something that men suffer from, at least in my experience, which is that Lindsay comes home with a problem. And my immediate reaction is to try to help her solve that problem. I don't know if it's biological. I'm not sure whether it's my amygdala or my lizard brain, but there's some, reflexively, I go into problem solving mode. It feels like, like that's what I'm supposed to do. And eight out of 10 times, it's not what she wants. And so because I know that I'm bad at that, we've created these, you know, our version of mnemonic devices, which is like, I now ask her, do you want me to solve this problem? Or do you want me to just listen? And almost always she just wants me to listen.

• 20:31Speaker 00

  So in the, the opposite of like, you know, if someone asks me a question on a topic and I can go on a tangent about a story, I actually have to spend a lot of time moving from my amygdala to my prefrontal cortex to actually be a great husband to her. Same thing with the kids. Often what I realize is my reflex with Bailey and Zoe is often the wrong thing. Bailey tells me about a problem, I go in solution mode. And what Lindsay will often say is, that's not what she was asking you to do. She just wanted to be heard, or she was looking for your advice, or she wasn't looking for you to solve the problem for her. So that journey, I think I'm, I am.

• 21:14Speaker 00

  I'm not, I'm not at the sort of escape velocity yet with those two things that I want to get good at.

• 21:20Shane Parrish?

  I think it's interesting because a lot of people who hold themselves to high standards in any area, hold themselves to high standards in every area, and they want competing things. They want to be world-class at their profession. They also want to be world-class at being a father and world-class at being a mother or partner, or, and they want to be world-class at everything. And these things often are in conflict with each other.

• 21:49Speaker 00

  When I was younger, I used to play Street Fighter. And Street Fighter, when you pick your character, you basically pick a character for two reasons. One is based on appearance. You want the big character, you want the small character, you want the, you know, the woman or the man, or whatever the character might be. The second element is you'll get the scores. And either they're great at defense and then they're bad at offense, or they're great at jumping, but they're bad at kicking. I think kind of life is like that a little bit too, that you have to sort of pick your, what you want to be good at. You cannot be good at jumping, defense, offense, kicking, punching, in sort of the, you know, in, in, in the metaphor of Street Fighter. I think you have to pick. And I think that that's kind of what prioritization is. It's deciding what you want and then reminding yourself of what you want.

• 22:34Speaker 00

  There are things that every now and then I get a glimmer of, you know, have I traveled the world enough? Probably not. Do I take my kids on enough, you know, like month-long trips, safaris? I don't, I can't do that right now. I have to select what I'm going to do. I can't be everything to everyone. And I've kind of made peace with that years ago, that at this particular phase of my life, this is what I, I, I need, and this is what I want. It's also the reason why I'm very particular about who I spend my time with. Because I do believe that There are genuinely energy vampires and energy catalysts in humans.

• 23:13Speaker 00

  There's also energy vampires and energy catalysts even in geographies. I mean, you know, I moved to Montreal two years ago. Partially was Montreal was this place that Lindsay and I kept finding was this energy catalyst for us. When we would come into the city, we'd spend time here, something changed in our brains. And I think you have to be deliberate about those things. Like, what do you want to be good at? What do you want to spend your time on? Who do you want to spend your time with? Where do you want to spend your time from a geographic perspective? And I think if you try to do all of it all the time, you end up being very mediocre.

• 23:49Shane Parrish?

  Most people don't want to prioritize because, I mean, they do in a way, but they don't want to say no to anything. They don't, it's sort of like, think about the courage to close doors. And it's really hard to say no to things.

• 24:03Speaker 00

  It's especially hard, especially if those things, there's an element of things that give you joy. I don't think you can live, I don't think the, if you use the lens in your life of how you do anything is how you do everything. You have to be very careful about like how you do things. Because if you want to do everything well, or you want to do everything with intentionality, you just have to be selective. I don't know anyone who is great at everything. The mentors in my life, the role models in my life, they tend to be spiky objects. Shopify is a team of spiky objects. We often joke about it as like the island of misfit toys.

• 24:42Speaker 00

  But what that, what we really mean is that there's no, there's no consultant in the world that would have put together a team at Shopify. In the early days, kind of in the, in the sort of the middle, you know, post-IPO days. And certainly modern days, right now in 2025, there's no team that, like, there's no one to put together this team. But it works. Why? Because there is this commitment.

• 25:07Speaker 00

  On our team that whatever, whatever the thing you're responsible for, you are going to try to be the very, very best in the world at that particular thing. Product, design, sales, storytelling, finance, legal, whatever that might be. That's the commitment. And then every year you have to requalify for that commitment. When you look at other companies, I've sort of poked on Google a little bit on this only because I know a few people there that are like this. But you do see much more well-rounded executives and more well-rounded leaders. It's actually the reason why net-net, I always prefer founder-led companies than professionally managed companies. I think founder-led companies are more interesting.

• 25:49Shane Parrish?

  Talk to me about the notion of requalifying for your job every year. What does that mean?

• 25:56Speaker 00

  It's sort of, I mean, it's in the sort of same way that like we have this trust battery metaphor that at Shopify, those with autonomy have a very high trust battery. And those that end up having to leave the company, it's because their trust battery is so low that like an old cellphone, it just cannot be recharged. You don't know exactly are you at 46% or 66%, but you know direction where you're at. The same thing exists for this requalification, that you can tell when someone, I think you can tell when someone is requalifying for their job. What that means is if you think about the growth of Shopify, which grows, you know, we've, we're growing a lot. Forget sort of the top-line revenue or free cash or margin growth, anything like that.

• 26:37Speaker 00

  But just like the growth of Shopify, product areas, GMV, the number of merchants, the geographies, the impact we have on the world, it is growing at this massive pace. I think in order to be on our team, especially to be a leader at Shopify, you have to believe that, you have to want to keep getting better, meaning stasis is not acceptable. The thing you did last year may have got you a high five and an attaboy and a pat on the back and a, whatever. All the great stuff that comes along with that, that is not good enough anymore. And actually at Shopify, I think that's truly, I mean, the source of that energy is Toby. That there's probably no one that I've ever met on the planet, I've worked with Toby now for almost two decades.

• 27:19Speaker 00

  You know him very well too, he's a friend of yours as well. There is no one that...

• 27:25Speaker 00

  Pushes himself to be the very best at product and technology the way he does. And so he inspires all of us to just continuously say, okay, last year was pretty good. This next year, I think I can, like, I think there's another, another gear left. That's actually the gift that he has given me in my career is that he's consistently, over, you know, almost two decade period, he has been the person more than anyone in my life, maybe other than Lindsay, who has seen a better version of me than I saw for myself. He keeps reminding me all the time, it happened a couple of weeks ago, we were on an offsite, that there is another gear in me. And so now he presents that, that optionality, that, that, that opportunity.

• 28:08Speaker 00

  And now it's up to me to actually go through. And I think for someone with my personality, with someone with my ambition, that works very well for me.

• 28:20Shane Parrish?

  What does it look like when he reminds you that there's another level for you? Does he just come, he, he doesn't come to you and say, hey, Harley, there's another level for you. What does he say?

• 28:29Speaker 00

  He's much more German about it. Which is funny because he sort of calls it the German, it's like the German thing for him, but it's actually also like the Jewish mother thing for me, which is, you know, you just got 98% on your exam, you go see your mom, and your mom says, great, what happened to the other 2%? Which actually I've now learned, it's actually very much a, at least the way it's been described to me, is that it's actually an immigrant thing, that a lot of immigrant parents are like that. Like, that's great, but like, what happened here? How can you do better? So that's part of it. The other part of it is just that when he gives me a compliment, it is because I went, I went so above and beyond. Like, he basically sets a bar for me of what great looks like.

• 29:11Speaker 00

  And doing my job really well is the expectation, knocking it out of the park, going like, resetting what corporate storytelling looks like, or how to do, you know, earnings.

• 29:26Speaker 00

  When you do that exceptionally well, that's when he says, "That was a great job." And he is, he's very thoughtful about how he explains, how he gives those, "That was really great." He kind of shows you that thing you did that is so far beyond the expectation of, of the industry, that you're resetting it. There's this really great thing we talk about, um, which is, it'd be really great, like, I say this, I say this a lot, but I adopted from him, which is, every person that works at Shopify should be able to go to their industry conference, whatever their category, whatever area they're in the business, and they should give the keynote about how they're doing their job, completely different than everybody in the crowd. Which is like, the most global maxima, not local maxima thing.

• 30:08Speaker 00

  It is, like, the local maxima is like, you know, you're at the top of the mountain, you're doing better than everyone else is doing your job. The global maxima, which is like, Toby in a nutshell, is, there's a whole other mountain over here. That's where, that's how you re-qualify. And that makes it incredibly challenging, but also incredibly rewarding. There's this, you know, thing about life's work, I think it obviously gets lumped into like, you know, happiness and contentment and all that sort of stuff also. Um, we can talk about how to find your life's work, but ultimately, the way you continue to do your life's work is, is when you feel fundamentally that you can see serious progress. It's not type one fun, it's like, type two fun.

• 30:52Speaker 00

  And type two fun is the type of fun that you only realize that it was fun after you complete it. In the middle of the race, it's not really that much fun. It's at the finish line, you're like, "Wow, that was fun." That tends to be the developmental journey of Shopify.

• 31:08Shane Parrish?

  A little anecdote about the, "That's your job, that's what you're supposed to do." I was at an NFL training camp, and, uh, I was with Carl Dubas, who was the GM of the Maple Leafs at the time, we were watching this practice. And this rookie receiver caught the ball, and it was a great catch, but he started celebrating. The coach came over and he's like, "That's what you're supposed to do, why are you celebrating?"

• 31:29Speaker 00

  I'm paying you to catch the ball, your whole job.

• 31:31Shane Parrish?

  You're paid to catch the ball, and it's stuck with me ever since then.

• 31:34Speaker 00

  That's right. It is, um, I think when you're, when you're playing at a certain level of, of play, whether it's through podcasts, or through business, or through sport, or music, you know, or art, music, if you try to, if you, if you want to be above average, Most people can get there. Practice, determination. But this idea of thinking about things in sort of this like local maximum versus global maximum perspective creates a whole other surface area of which you can go and do crazy and cool stuff. I do think that is difficult to do by yourself. I think you actually are one of the unique situations where you hold yourself to such a high standard that you actually don't need anyone pulling you to get better at your craft

• 32:18Speaker 00

  because you hold yourself to this ridiculous standard. Most people are not like that. Most people need someone else to help them pull up to the next level. And if you find someone like that and you can you sort of mutually commit to one another. I mean, that's real partnership. That makes for, that's how you build a hundred billion dollar company, I think.

• 32:37Shane Parrish?

  It's fascinating because I tell my kids that, right? Like when you're at school, like try to partner with the people who are going to hold you to the highest standard, who are going to demand the most from you, who are going to show you what you're capable of and what you can do. And they take that too, and they hold other people to really high standards.

• 32:53Speaker 00

  That's right. That's right. And then you sort of, you know, it is ironic though, almost paradoxical that, you know, the people that you often hang out with in high school or in school in general tend to be very much like you. And what I've actually experienced is that I think the best partnerships, at least from business perspective, are people that are totally not like you.

• 33:10Shane Parrish?

  Totally.

• 33:10Speaker 00

  And not sure Toby and I would have been friends in high school. I was class president. He was like taking apart computers in his bedroom. The people you tend to spend more time with, that you gravitate to, you tend to have similar interest with. You tend to have similar skill sets with. You're both into basketball. You're both into, you know, debate club or whatever it might be. But actually, if you're in high school right now and you're watching this and you want to start a company, my, my advice would be if you're in like drama club, go find someone like in the AV club and then go find someone in like the computer, like the coding club and go find someone like who's painting. And those should be your co-founders because each of you now can bring different skill sets to the table and together you can build something remarkable.

• 33:50Shane Parrish?

  My youngest wants to start a company and he's like, why should I go to university? Why do I want to go to college? He's like, I don't need that. And I'm like, well, maybe just to find a co-founder.

• 33:59Speaker 00

  That's a good place to do it.

• 34:00Shane Parrish?

  Yeah.

• 34:02Speaker 02

  This episode is brought to you by Michelob Ultra. Good times mean competitions between you and your friends. Like seeing who can throw some pigskin the farthest or rush the field the fastest. Winner gets an ultra because it's not just a superior light beer. It's also giving fans superior access to their favorite sporting events. Superior is worth playing for. Visit michelobultra.com/superioraccess to enter. Enjoy responsibly. Copyright 2026 Anheuser Busch InBev Michelob Ultra Beer, St. Louis, Missouri.

• 34:32Speaker 03

  This episode is brought to you by Subaru. You know that place your mind always wanders to? The lake, the mountains, the homes of the people you love most? The completely redesigned 2026 Subaru Outback is built to help you get there. With legendary capabilities, standard symmetrical all wheel drive and the confidence to go further. The 2026 Subaru Outback. Love never looked so good. Visit subaru.com/outback to learn more.

• 34:57Shane Parrish?

  I want to come back to sort of requalifying for your job though, because you switched from being COO to being president or chief storyteller, as you call it. Talk to me about that transition, how you came to realize that was the thing. Because you went from thousands of people reporting to you to a smaller number. Even if it's a lot of people, it's still much smaller.

• 35:20Speaker 00

  At a seven or eight thousand person company, like a small number of people, still a lot of people. But yeah, that was, um, okay. So a couple of things on that and a couple of different sort of levels of abstraction, I guess.

• 35:32Speaker 00

  I do believe that there are different phases of companies. And I think at the early phases of companies, it's just, it's just mayhem. Like everybody do everything. It's like Swiss Army knife time. And in those early days of Shopify, there's a photo that every couple of years I, I, I put out on, on social media of me like mopping the floors. You may have seen it, but like I, I, I may have mopped the floor once or twice, but it was, it's sort of a, you know, it's, it's a metaphor for like those early days. That like the floor is dirty.

• 35:59Shane Parrish?

  You do everything.

• 36:00Speaker 00

  You do everything. That's kind of how it works. And then I think, you know, as the company begins to operationalize, you begin to have teams and organizations and general managers and divisions and all that. I became chief operating officer around just, just post IPO until around 2021, I think, so much for six years. I did it because that's what Toby asked me to do. We'd never had a COO before and, and, and it was sort of this way of me looking after operations, specifically business operations.

• 36:28Speaker 00

  It didn't come naturally to me. But back to sort of the lifelong learner and the global maxima thing and Toby pushing me into different directions, I was like, I'm gonna get good at this. But it was never natural to me, never felt like I was in my flow state. But I liked it. I liked having a big team. I liked being responsible for a lot of things. There was a little bit of ego in there. I felt very important. And it took me a while to realize that maybe this isn't for me. Maybe I'm not the right person to do it. Around the same time, I had someone that we had hired that was reporting to me, who was running our payments team, Kaz.

• 37:11Speaker 00

  And in almost every interaction I had, it did sort of feel like, Kaz really likes operations. Like, it feels like his ground state. He's kind of always doing it. And so I saw glimmers of like, what people that are truly operationally minded look like. But a couple hurdles I had, one is that I don't think I was ready to admit that this was not, for me, this wasn't my thing. I don't like to admit that I'm not good at something. I prefer to much to get better at it. I also, I think I was afraid to say, the thing I want to do is storytelling. It felt like maybe that's not enough.

• 37:55Speaker 00

  And it came with, you know, smaller team, it came with, it just came with less, you know, less areas of responsibility. Even though each others were shallow, I was like, what I really want to do is this other thing. It's like one area responsibility, but it's really, really deep. Is that enough for me? It became obvious to me that that wasn't the right thing. And actually, I think it became obvious to Toby that like, I wasn't very happy. I wasn't being my exothermic self. And for someone that's always been exothermic, that's always been high energy, in those sort of, at the end of my COO stage, I didn't have it. I just, I wasn't meeting merchants the same way that I, like, I love meeting merchants. My favorite thing in the world. I just, I wasn't.

• 38:42Speaker 00

  It was clear I was in the wrong year and it was Toby that identified it and said, "There's this other thing. We could find someone to be the Chief Operating Officer." And it was actually between myself and Kaz taken it was Toby Shannon who initially took in. He was a great Chief Operating Officer, Chief COO as well. Toby almost gave me the permission to say, "This other thing that you think is maybe not enough, it's like, it's totally enough. Like, this is super important. And more importantly, you can be world-class at this thing." And that was this like huge aha moment. That was, it reminded me that, okay, the Venn diagram of what I love doing, you know, like, it's like the ikigai,

• 39:26Speaker 00

  almost perfectly described. Like, what do you love? What does the world value? What can you get paid for? What, like, I forget all the different components of it, but that's generally the ikigai. Immediately as I began to even understand what ikigai was, I was like, "That's it for me." It's like, this role, the storyteller, the president of the company, where my job is to infect in the most positive way the world with the Shopify message. That every enterprise merchant on the planet that should be on Shopify, I'm going to convince them to do so. That every partner that should work with us, I'm going to convince them. That every investor knows exactly how great of a company this is. That every media opportunity I have, I'm going to talk about the, this journey, this product,

• 40:06Speaker 00

  this incredible piece of software we've built, why it is so important. Why it is so dramatically different than everything else that has come before us. I don't know, it was four or five years ago.

• 40:22Speaker 00

  It completely changed my energy levels. It made me exothermic again. It made me excited again. It wanted, it made me want to recommit year after year after year to Shopify and to Toby and to, and to this mission that we're on. I fell in love with the mission again. I almost forgot about the mission for a while. It became so operational. And what it also substantiated was that...

• 40:45Speaker 00

  I didn't have to be good at all these different things. If the one thing that I feel I can be world-class, to go back to that concept, is sufficiently value-add that will change the company, that will change the direction of the company, that's enough. I am enough to do that. And I, I really think that most companies end up looking at a buffet of their leaders and looking at the slots that are available and just go like, like, go here, go here, go there. And I think it takes a very thoughtful and very often founder, CEO, or founder leader like Toby, someone like that to say, okay, here are the players I have, here are the things that are most important.

• 41:29Speaker 00

  I'm going to skill match. So it isn't who's been there the longest or who's had that job somewhere else. It is who is the very best person on the planet, not in the company, on the planet for this job. And that person exists here, that's the job they should do. It allowed me to recommit for a lot longer to Shopify, to, to working here, to helping to build this company. It's made me a lot happier. Even Lindsay would say that between 2020 and 2022, which I use those years because we're still in COVID and like we're still work from home and, and I wasn't around a lot of people and as a power extrovert, that was challenging for me. But simply changing my area's responsibility completely re-engaged me. And it's, it feels like this is a job that I always should have had.

• 42:14Speaker 00

  I think Shopify, I think Shopify had to get to a particular size and place for me to do this. It almost feels like Shopify kind of grew into the company that would allow me to be its storyteller. I couldn't have done this in 2010 or 2013 or 2018. It had to happen at the right time and I'm super fortunate that it did, grateful that it did.

• 42:33Shane Parrish?

  I feel like you've had more of an impact than you think, not only on Shopify, but on other companies. I feel like the storytelling and getting out there more, like you've really changed. The bar for a lot of other companies as well. So not only Shopify, but you've sort of set. Other people didn't even know it was possible to have that sort of impact.

• 42:53Speaker 00

  I mean, that means a great deal to me. That goes back to that industry, you know, conference that we talked about as a metaphor that, you know, I try to stand, I, I want to be able to stand up at, at the conference of every chief storyteller, every, you know, president of any, of any company in the world and say, here's, I'm doing it differently. Um, you know, Lulu is on our board. He was amazing. Uh, probably one of the greatest comms geniuses on the planet. Talks about this go to rec. She has a famous go to rec manifesto. That's kind of what I've always been doing. This idea that even the way that I, I treat earnings, it's not, it's not an earnings call for me. It's a storytelling opportunity.

• 43:28Shane Parrish?

  Yeah.

• 43:29Speaker 00

  And, um, I love seeing all these companies now, you know, now you see a bunch of tech companies turning the camera around and them being like, here's how the earnings went. Like, I've been doing that for a while now. And so I'm,

• 43:39Shane Parrish?

  That's what I mean.

• 43:39Speaker 00

  I'm, uh, it's, I think it's really fun and I, and because I'm now seeing other companies do that. I'm like, okay. So like, now how can I keep going from here? How do I, like, what's the next step here? How do I requalify? I've done that already. I've done the like go direct to one earnings. Like what's the, what's the 10x version of that? What's the global maximum version of that? And that makes it really fun.

• 43:59Shane Parrish?

  Despite what you, uh, may think of yourself, I think of you as a world-class storyteller.

• 44:06Speaker 00

  Thank you.

• 44:06Shane Parrish?

  How, how did you develop that skill? What does that look like? Like, how do we make other people world-class or better at storytelling?

• 44:14Speaker 00

  Practice really helps. You know, now I get to do like the knowledge projects. It's like, this is a big podcast. I'm not trying to, you know, blow a smoke or flatter you, but this is a big podcast. Um, I didn't start by doing the Shane Parrish podcast. I started by doing a lot of tiny little local podcasts and watching them over and over again. You know, I know there's some people that, that hate watching themselves on camera. Uh, maybe this sounds like narcissistic or something, but I, I don't mind. I actually like the, I like watching it because I was able to remove connector words, for example. I say, um, a lot less than most people do because I've watched myself do it a lot. And I'm like, I'm going to fix this particular issue. That's the first thing. The second thing is I think a lot of people end up trying to emulate other speakers.

• 44:55Speaker 00

  I see a lot of in tech in particular, there was an era where like everyone kind of sounded like Gary Vaynerchuk for a little bit. I know Gary well. He's a friend. I think Gary is incredible, you know, speaker and, and his keynotes are, are legendary, but that's his style. And then you see other people that try to do the whole Rogan thing, or the Shane thing, or the Tim Ferriss thing. And I don't, I never tried to be somebody else. I wanted to be my, the version of me, which is a little bit excited, not always as perfectly articulate. I speak very quickly. I want to make sure everyone understands me, but I've sort of developed my own style of it. And maybe the third thing, which is probably obvious, but great mentors,

• 45:35Speaker 00

  people that I deeply look up to when it comes to speaking. And I think the person that has probably done the most for me in terms of watching how he speaks, how he captures the attention of a crowd with story is Seth, Seth Godin. I think Seth Godin is the world's greatest storyteller. He can tell a story about Brussels sprouts, I have a great story about Brussels sprouts, but he talks about, he could tell a story about coffee or purple cows, and, and watching him and talking to him and learning from him. And then it's just reps. How many reps have you done? I mean, the reason that, you know, Toby is such a great coder is he's written more code than probably anyone else at Shopify, even now. I mean, he doesn't write as much code now as he once did, but just in terms of longevity

• 46:20Speaker 00

  of software development, he's had more reps than other people have done. We hear this about athletes all the time, that like, the greatest athletes were the ones that got up early, that went to the gym before everyone else got to the gym. Like, they had a double workout. That's a big part of it. I think the other thing is, the, the content you talk about. I think it is really easy to talk about stories that are your stories. When I, when I tell a story, whether it's about Shopify, or it's about my life, or my family, or DJing, or something like that, I always start with my experience. When I was 13, when I was 18, when I traveled here. I think by starting with you, and you putting

• 47:05Speaker 00

  yourself into the story, one, it can't be wrong, because it's your story, like, it happened to you. But two, it immediately invokes, if, if it's true, you can speak with such conviction, with such passion.

• 47:22Speaker 00

  The easiest story for me to tell is out of Shopify because the story of Shopify is a story of entrepreneurship. And but my story is also of entrepreneurship, my family story about entrepreneurship. My friends around me, you know, you know, almost every one of my best friends, they're all entrepreneurs. Some of them are in the restaurant business and some of them are in fintech and some of them are lawyers, but what they all have in common is they all are first and foremost entrepreneurs. So the storyline that I've chosen is entrepreneurship.

• 47:54Speaker 00

  And it's not an accident that the company that I've committed to for so long, for decades, is the entrepreneurship company. Could I sell cars or could I sell biotech? Maybe I don't think I can be, I can tell the, the story in that way. I think part of what isn't wonderful about modern day business leadership is that we are not selling widgets. I think, I don't know if you ever watched like some of the old, like Glenn Gary, Glenn Ross movies or I mean, frankly, like Always be selling. Oh, yeah, ABC, right, closing. Always be closing. Always be closing, you know, coffees for closers. You watch some of these old school business or even

• 48:40Speaker 00

  Wall Street. Michael Douglas, amazing movie. You watch these movies and you see these like business owners in these movies. And it's a reflection, of course, of, of the society at the time, but they were selling widgets. The executive could be selling tires or the executive could be selling soda water or they can be selling whatever. It didn't matter. They were implementing the same strategies to sell one widget as they would any other. In many ways, business is now way more personal. And I think one of the advantages of it being more personal is that you're able as a like the company can attract people whose personal mission is tied into the company's mission. I don't think that there are any, when I look at every leader that I admire, business leader that I admire, entrepreneur that I admire.

• 49:26Speaker 00

  There's no accident for why they're at their company or why they built their company. Either they experienced a problem themselves and they went to solve the problem, or they had something happen to them when they were younger in life and that kind of changed their mindset around that product. There is a deep connection to it. There's, I mean, Fire Belly Tea, my little tea company that started with Dave Siegel that you're now involved with a little bit. The reason I wanted to start this company with Dave is like, there was no one on the planet more passionate about tea. The fact that David Siegel, who created David's Tea, was not running a tea company, you know, in the modern world was ridiculous. All he cares about is tea.

• 50:11Speaker 00

  Of course he should be, he should start a tea company. He already started one because of, you know, some interpersonal issues, he ended up leaving his company. Of course you should start it. If you are deeply passionate about something, I wear a James Purse t-shirt every day and today I'm wearing all James Purse. Of course James Purse is successful because no one thinks about GSM counts or rib more than he does. No one thinks about Japanese cotton versus American cotton more than he does. No one thinks about, actually, these are called the parachute pants, these are his favorite pants. I hung out with him a couple of weeks ago and we both literally walked in wearing the exact same thing. Of course his pants are amazing because he made these pants for himself.

• 50:53Speaker 00

  It just turns out that thousands of other people also want to wear those pants. The idea that the people that are running businesses are deeply connected to those businesses and the products they're creating, I think is a new way to run companies that our parents and grandparents didn't have. Some, you know, go back 150 years, some of the bakers truly loved baking, but some of them just did so because they had to survive. My grandfather had no interest in eggs whatsoever. Anytime I tried to engage him on eggs, I got a blank stare. He wasn't selling eggs because he cared about eggs. He was selling eggs as a means of survival.

• 51:30Speaker 00

  Forced entrepreneurship and passion-based entrepreneurship are very, very different things. And the idea of us, you doing your life's work and me doing my life's work, that is a concept that was foreign to our parents and grandparents.

• 51:43Shane Parrish?

  Totally. They did sort of what they had to to.

• 51:46Speaker 00

  Life's work. That's a nice, you know, like, I can, I never said that to my grandfather.

• 51:49Shane Parrish?

  That's a luxury.

• 51:50Speaker 00

  That's a luxury, young man, you know. Wow, aren't you lucky? That sounds like a hobby to me. You know, as opposed to, they were rough and tumble. They were like, do whatever we needed to do to survive. If it was eggs or it was garments or whatever, you know, we're sitting in Montreal right now and about 10 kilometers north of here is the Chabanel Garment District. The Chabanel Garment District is an iconic area. It's probably four streets by four streets. And American Apparel, Buffalo Jeans, Algo Industries, so many companies, Kipar Suko, more, more modern companies, Essence is based there now, Moose Knuckles is based there.

• 52:34Speaker 00

  It's this tiny little area that so much of the apparel industries that we know today were created out of. Why did that exist? It existed because it was the lowest barrier to entry. The needle trade or the shemata business, which is sort of the Jewish version of that. The reason you see so many Jewish immigrants go into the shemata business, the needle trade, is because low barrier to entry. They couldn't go to biotech. Biotech had a high barrier to entry. You couldn't be, you couldn't have no money and start a biotech company or start a pharmaceutical company or start a technology company. But the clothing business, you need a sewing machine and that's it. And I, it's wonderful that we have that industry that's been built here.

• 53:18Speaker 00

  But there's a lot of people that ended up building those companies that built it because they had no choice. As opposed to because they chose to be, like James chose to be in this industry.

• 53:27Shane Parrish?

  You're the second person in the last month who's mentioned him and his shirts. I gotta check these.

• 53:32Speaker 00

  Yeah, check them out. They're, they're great.

• 53:34Shane Parrish?

  I want to come back to mentors for a second. So Seth Godin is one of your mentors. You have a personal board of directors in different aspects of your life. Whether it's relationship, business, storytelling. Walk me through some of the categories you have and some of the people that are in those categories.

• 53:52Speaker 00

  One thing that I think a lot of people, and I myself made this mistake, was that you end up, when you think about the idea of a mentor, you end up thinking about the 360 of the mentor. Like, I'm going to emulate everything about the mentor. My experience has been that, back to the spiky object thing, that any mentors that anyone watching or listening have in their lives, they probably are really good at something, like really good, obviously they wouldn't be a mentor otherwise, but they're probably lacking in other areas entirely. And I had a mentor early on in my life that ended up convincing me to go to law school. And I won't say his name now because I'm about to say something fairly, well, he won't mind, but I won't say his name anyway. He's ended up convincing me to move to Ottawa to go to law school.

• 54:35Speaker 00

  He convinced me to go to law school to become a better entrepreneur, not become a lawyer. Great man, I've known him since I was a child. I was actually, years before, I was the ring bearer at his first or second, I think his first wedding or second wedding. Which brings me to my point is that, like, this guy's an amazing career mentor and helped me more than almost anyone else. He's not what I would call a marriage or relationship mentor. He's on his third marriage now. And he's happily married now, but he's on his third marriage. If you try to cargo-cult everything about one particular person, you're going to adopt all their good stuff and all their bad stuff. Instead, it's much easier to figure out, what are the couple things I want to get good at?

• 55:17Speaker 00

  Entrepreneurship, being a great dad, being a great philanthropist, a great DJ, I want to be a great tea entrepreneur. And then looking at who's really good at that and ask them specifically to help you with that narrow category, as opposed to being a lot more broad. The other thing that happens is that there's a timeliness to these mentors, meaning someone that was your mentor, I don't know if you've ever had any business coaches or any coaches in your life?

• 55:46Shane Parrish?

  Yeah.

• 55:47Speaker 00

  So I think, I have a great coach in my life right now. It's probably my third or fourth coach that I've had. One of the things I think about coaching business coaches in particular is, at some point, you end up hearing a lot of the same stories or lessons or tools. Meaning, they have this wonderful toolbox, and part of what you're paying them to be your coaches, for them to open their toolbox and show you all their tools, and you can adopt some of them for yourself. But eventually you've seen the entire toolbox and that's a really good time and it's not a negative thing. It's not a criticism. It's a really good time to sort of move on to the next coach. The same thing goes with mentors that I don't think with very few exception, there's probably not going to be any one mentor that's going to be your life mentor in perpetuity because ultimately you are going to change, they're going to

• 56:32Speaker 00

  change, you're going to want some new perspectives. But one of the things that Lindsay and I did before we got married was we began to look at the couples we knew, most of them meaningfully older than us and saying, who do we think has a really good relationship, a really good marriage? How can we kind of emulate that? And we didn't say anything to them at the time, but then after we got married, we began to nonchalantly start spending time with them, like double dates with them and kind of seeing how they interact with each other and, and what their, like what their style was with each other. And we ended up developing kind of these relationship mentors. We ended up developing parental mentors and it's been, it's been awesome. It's been this incredible thing. And some of these

• 57:16Speaker 00

  people that are sort of quote unquote mentors are famous people. Lindsay and I recently created our family foundation and we want to have a real impact on our foundation. I got a chance to, to meet David Rubenstein, who created Carlisle Group and interviewed him for Big Shog, which is my, my little Jewish podcast archive that I have with David. And David Rubenstein talked about the rules of how he does philanthropy. So as an example, he talks about like, he'll only write a big check for an organization or a foundation or a charity where I'm going to get these kind of wrong, but effectively it's the project wouldn't start without him, or the project wouldn't end without him, where he can see

• 57:56Speaker 00

  the efficacy of the investment in his, in 10 year period and it's deeply personal to him. And so he sort of puts up these kind of, these, these, this rubric and, and if it fits those categories he's in, he'll, he'll give, in David Rubenstein's case, he'll give like 10 million or a hundred million dollars. So I began to ask David about philanthropy well after the interview happened. Tell me about this and how you look at that as well. I'm not necessarily sure David Rubenstein is, is a mentor per se, but he has helped me shape my own understanding of, of philanthropy.

• 58:31Speaker 00

  So he's sort of one that's quite famous. But we also have some friends here in Montreal who are not well known. No one knows them. They're very quiet philanthropists, but they, the way they do it is kind of strange. It's, it's all about like, like some people talk about impact investing. They kind of take this entrepreneurial approach to philanthropy, meaning they'll be very precise about what they donate to. So they'll say, they'll walk into a hospital and they'll say, why is there a lineup here? And the foundation people, the hospital will be like, well, unfortunately, there's only one machine. And this is very popular. This is a cancer screening machine. They'll say, great, how much is the second machine? They'll be like, it's $2 million. Okay, do you have capacity for it? Not really. What do you need? Well, I need a radiologist for it. Well, how much is that? And then these people will sort of go in, they'll come back to the hospital, literally a week later, they'll say, great.

• 59:16Speaker 00

  We figured out that you need a radiologist, you need a machine, you need a new location. You all seem to change some power to sort of, for this all to work because you don't have enough power supply here. So we think it's four and a half million dollars. We're going to go and raise four and a half million dollars for this exact thing, this precise thing. And lo and behold, six months later, you walk into this hospital, the machine is there, there's no lineup anymore and everything is solved. So they are not doing this sort of blanket philanthropy. They're very, being very precise. And so we've, we've done, we've been able to kind of find these different people in these different categories. And it's, it's amazing because you get this cheat sheet for anything you want to get good at. I started DJing again recently and I, so I began talking to, there's this amazing shop here called Moog, M-O-O-G, Moog Audio.

• 59:58Speaker 00

  Amazing, like legendary music shop in, in, in the world, but certainly here in Montreal. And so I started going to the shop more often, hanging out there and like, listening to the DJs. I ended up meeting one of the DJs, guy Alex, who runs the shop and asking him like, so how do you think about like, when you beat mix? What do you do? Is it eight beat counts or are you using new technology? How do you think about fading? There's, there's something called stems in DJing. So you take a song, there are three stems. There's basically the drum, bass, like the beat, there's the vocals and there's the instrumentals. And I was like, when I was DJing, we couldn't necessarily identify or isolate stems. I was like, but you seem to be doing that a lot when you're DJing. And I listened to your SoundCloud stuff and he's like, well, here's how it, you can do this in every category of your life. And it doesn't have to be these famous people.

• 1:00:43Speaker 00

  It can be a random person you end up meeting at the DJ shop. And it's been, it's been amazing for me and Lindsay. It's been amazing for my, my own life.

• 1:00:54Speaker 00

  But I will say that a lot of, a lot of people try to emulate something like that. And there's this cringe factor involved that I find that most people can't get over. And the cringe factor is often, I have to send a lot of text messages and a lot of emails and a lot of, even now that, you know, a lot, some people know me, I still, like I have zero cringe in my life. I don't worry about cringe at all. I never feel that way at all. So if there's someone that I really want to get, you know, intro to and start working with and start getting mentorship from, I will like, I will go full on and I will never be disrespectful, but I have no issue with rejection whatsoever. And I think that's

• 1:01:36Speaker 00

  the largest blocker of why more people don't create these personal boards of directors.

• 1:01:40Shane Parrish?

  Let's go deeper on that for a second. I think you hit on a really key point, which is, I, I kind of think of this as like, most people don't want to look like an idiot in the short term, to look like a genius in the long term. And because they're unwilling to do something where somebody might say no, or it might make them look, you know, you want to start skateboarding, well, you, you've got to get on a skateboard to actually start skateboarding, but you're going to look like a fool for the first few months, or maybe weeks, or years, or whatever, but you're unwilling to do that. And so you never get better at these things.

• 1:02:11Speaker 00

  I have very high cringe, pain tolerance, whatever you want to call it. I have no issue with that whatsoever. I think that there is this, this gets easier also with age, I find. The older I get, the less I really, I really care about that stuff. But yeah, I think most people are not willing to look stupid for a period of time. I think the other thing is that, I think about this all from the, the concept of like entrepreneurship. In my office, here, here in Montreal, Shopify office, I have the original screen print that Ben Francis used to create Jim Shark. It was a gift. It's a super meaningful gift that he gave me. I love it. I have it hung up in my office. Part of the reason why it's up there is because I think that it's an amazing gift and Jim Shark is this homegrown success story on Shopify. It exemplifies everything we stand for. It's incredible.

• 1:02:55Speaker 00

  But the other reason I have it up there is because what most people don't know is that that was not Ben Francis's first company. That Ben Francis actually had a bunch of failed companies before he landed on Jim Shark. And I think about this idea of this cost of failure, not just from entrepreneurship perspective, but in general, you have to basically figure out. With anything you're doing, what is the cost of failure here? If the cost of failure is really high, you really have to think about it. It's, you have to sort of do a little bit of like the math of is the cost of, is, is the benefit of success worth the cost of failure? In some ways, it's just not. But, I mean, for $39 a month, you can build a store. It's not a pitch for ShopPlay, but $39, you can build a store. If it works, blow it up. If it doesn't work, try something else.

• 1:03:38Speaker 00

  There are still too many people that are apprehensive, that, that, that don't want to put themselves out there because of this fear of failure. And I've long believed that, you know, getting really, really comfortable with being uncomfortable is magic. It's totally magic. And I wasn't always good at that. I don't think you can be born with that. I think you can learn that. I think you can learn resilience.

• 1:04:04Speaker 00

  But I don't, I don't know anyone that I admire who's had success, who has not gone through that period of making kind of, looking kind of dumb. And if you've watched the first interview you've ever done.

• 1:04:17Shane Parrish?

  Me? Oh, God, yeah.

• 1:04:19Speaker 00

  What was that?

• 1:04:20Shane Parrish?

  I wouldn't listen to the first, I think, like 20 or 30 of them. I wanted to get a catalog and then I wanted to listen to them.

• 1:04:26Speaker 00

  Sure.

• 1:04:26Shane Parrish?

  And then I went for like a really long run and I started listening to them and I was like, oh my God. And it's like, I should have asked this follow-up and why did I phrase it that way? And like you, I'm incredibly hard on myself. Came back, went through every transcript and like, I was like, I want to get better at this for everybody else, but yeah.

• 1:04:45Speaker 00

  There is no secrets to why you've been so successful. In my, in my view, I've known you now for a number of years. You, you simply out care other people. And I think that out caring thing

• 1:04:59Speaker 00

  supersedes IQ, EQ, raw talent.

• 1:05:04Shane Parrish?

  Double click on that for a second.

• 1:05:06Speaker 00

  I think that. I will take someone, it's the reason why I like entrepreneurs so much, that I think entrepreneurs, the right entrepreneurs, the best entrepreneurs, they just simply out care other people. They are willing to, if you put two people in a room, one person has 50% capacity, another person 100% capacity, but that 100% capacity person is just not caring as much as 50%. I think I can help that 50% person get more skill. I'm not sure I can change their level of ambition. I think you can change ambition, but I think like sheer innate, deep rooted ambition, uh, which call it care, whatever, whatever nomenclature you want to use. I think that is a superpower.

• 1:05:49Speaker 00

  And it's also the reason why, when I meet someone, they say, what do you think I should do with my life? I often ask them, what do you do for fun? Because often the what you do for fun question ends up turning into, I really want to be a fashion designer. And I'm like, you should go be a fashion designer. Even if you've ever done it, you may not have the raw skills, you will learn those skills, but you seem to really care about this thing. You're probably going to be good at it.

• 1:06:14Shane Parrish?

  Is there a difference between who cares the most and who wants it more? Or the, like, how do you see that nuance?

• 1:06:20Speaker 00

  I look at them the same, in my view. Usually, high care comes from high intent, or high, uh, an elevated level of desire to succeed. I'm trying to teach my kids that right now. I, I spend a lot of, you know, this is kind of weird, but I kind of wish I had kids pre-IPO rather than post-IPO.

• 1:06:41Shane Parrish?

  Why?

• 1:06:43Speaker 00

  I think,

• 1:06:46Speaker 00

  whatever success that I've had and success of, of, of things I've been involved with,

• 1:06:52Speaker 00

  they are more meaningful to me because obviously I know where I come from, I know how hard it was. But I also see how Lindsay, how my wife, sees my relationship with things that I've done, in particular with Shopify. Lindsay has great.

• 1:07:09Speaker 00

  A wonderful emotional connection. Shopify for Lindsay, even my wife, is not just a company. She remembers, you know, those early days. She remembers those, like, being on top of Tucker's Marketplace in the Byward Market, the office stunk like the buffet restaurant and struggling. This is pre-Series A even. And I like that. I love that she knows that. She knows how meaningful it is because she's seen the entire journey. My kids were born in the last eight years or so. They kind of only know our life being pretty good. Our lives changed post-IPO. I don't think that's a secret. Financially, my life changed.

• 1:07:50Speaker 00

  And I don't take it for granted, but I kind of wish they knew what Lindsay and my first apartment looked like in Ottawa, Canada, and how gross it was. It wasn't gross because it was dirty. It was just, it was a nice apartment because we couldn't afford anything else. And so what Lindsay often tells me is just like, yeah, the kids didn't see that, but tell them those stories. And so I do. I tell those kids. I tell my daughters the stories of those early days and how scary it was. And we didn't know if it was going to succeed or not. And I want them to see that. I think, I don't want them to think any of this came simply because it was fate or just kind of happened.

• 1:08:27Speaker 00

  Or, you know, I mean, luck plays a role here, but this was sheer grit and willpower. And it still is. Part of the reason why I like starting these small projects like Big Shot or Fire Belly is I want the kids to see that. I want the kids to see this thing that, you know, that first episode of Big Shot we did was, it was Charles Bronfman. It didn't do very well. I wasn't very good at it. I wasn't a good interviewer. I didn't know what questions to ask. Dave and I were kind of awkward, fumbling along together. And Bailey, my eldest, has sort of memorized most of that episode. And now she watches that. They love watching Big Shot. They also watched the most recent episode,

• 1:09:10Speaker 00

  Bobby Kotick, who built Activision Blizzard. We put that out last week. And I love watching her see the difference in style and the articulation because I want her to know that, like, all the things she wants in her life, she can have, but it won't be easy. No one's going to give it to her. And it's going to kind of suck at the beginning.

• 1:09:35Speaker 02

  This episode is brought to you by Michelob Ultra. Good times mean competitions between you and your friends. Like seeing who can throw some pigskin the farthest or rush the field the fastest. Winner gets an ultra because it's not just a superior like beer. It's also giving fans superior access to their favorite sporting events. Superior is worth playing for. Visit michelobultra.com/superioraccess to enter. Enjoy responsibly. Copyright 2026 Anheuser Busch InBev Michelob Ultra Beer, St. Louis, Missouri.

• 1:10:04Speaker 03

  This episode is brought to you by Subaru. You know that place your mind always wanders to? The lake, the mountains, the homes of the people you love most? The completely redesigned 2026 Subaru Outback is built to help you get there. With legendary capabilities, standard symmetrical all wheel drive and the confidence to go further. The 2026 Subaru Outback. Love never looked so good. Visit subaru.com/outback to learn more.

• 1:10:30Shane Parrish?

  Go a little bit deeper on that because you know what came to mind when you were saying that? Is this conversation I have with Chris Bosch?

• 1:10:38Shane Parrish?

  And the thing about that entire interview that sticks out with me even to this day is he told me this story about how growing up they had nothing. And he loved to play the private school kids.

• 1:10:51Speaker 00

  Yeah, and beat them.

• 1:10:52Shane Parrish?

  Because they're so entitled. He's like, they had air conditioning. They don't know what it's like to work out in a gym when it's 110 degrees.

• 1:11:01Speaker 00

  Yeah.

• 1:11:01Shane Parrish?

  They have no idea and I love to go in there and I love to win. And then at the end, he sort of like twisted this around. He's like, now my kids are those private school kids.

• 1:11:11Speaker 00

  It's really hard. I mean, I don't want to create artificial scarcity or artificial, you know?

• 1:11:22Speaker 00

  I don't want to create things that don't exist for my kids and pretend like our life is different than it is.

• 1:11:29Speaker 00

  This is where Lindsay's really great. Lindsay's a psychotherapist, so she thinks a lot more about this than I do. But she'll often remind me that like, it's not what you say, it's what you do, it's what they see. And so, you know, for example, we're fortunate to have some help at the house. But like Bailey makes her bed every day. Bailey puts her dishes away. Now, that's very different than, you know, what Chris Bosch said about like, you know, where how he grew up. But there's a certain level of like, respect that we show the people that have helped us. There's a certain level of care that we show the people that are around us. I'm not sure that I can invent

• 1:12:03Speaker 00

  some sort of, some version of poverty for my children. I think that would, that would

• 1:12:08Speaker 00

  part of why I work hard is so my, my, my kids can have, you know, less of that multi-generational trauma that I have felt. Yeah. But I want them to be grateful and hardworking and have conviction. I want them to work on projects together. I want them to fall on their face when, when they haven't done the right thing. And I want, I want to celebrate them when they work really, really hard. The type of school my, my, my daughters go to now was the type of school that my mom said I could, she couldn't afford to send me to.

• 1:12:40Speaker 00

  And that, that's one of the reasons why I, I worry about, am I doing all the right things? Am I a great, great parent? Am I a great father? I, I don't know that I am. I, I like, you know, Sundays here at Shopify. We have something called Builder Sundays. So we open up the offices. It's done in Montreal and Toronto. So anyone in the city that's an entrepreneur can come in and work from here. And I come in almost every Sunday and I often will bring, bring the kids. Usually I'll bring Bailey with me. And I'll just walk around and I'll talk to people and ask them how they can be helpful and stuff. And I see Bailey watching me do this and she's like, well, like, what's that person doing? I was like, well, that person's building a Shopify app. And she's like, well, what did he ask? And I was like, well, he asked, you know, once the app is built, how does he get people to use the app? And she said, well, what'd you say?

• 1:13:24Speaker 00

  And I said, well, you know, like, make sure the app adds a lot of value. And then the first five people that installed it, like, call them and ask them how you can make it better. And if you've made it better and they're happy, ask them to write a review. And, and so I'm beginning to think that parenting is not that complicated, that we complicate it. We try all these devices and, and, and, and these techniques and these.

• 1:13:48Speaker 00

  Programs and all these sort of things, but ultimately they're just watching us. And they're going to, they're going to copy and they're going to emulate the behavior they see from us. And if we're respectful, they're going to be respectful. And if we're hardworking, they're going to be hardworking. I think part of that, back to that family model of how you do anything is how you do everything. I don't actually care what my kids end up doing professionally, whether they're entrepreneurs or they're musicians or they're, you know, they're, they're trade, they have a trade that they work on. I just want them to have intentionality. I don't want them to do something just because, well, this is kind of where life brought me. I hate that. The opposite of how you do anything is how you do everything is this other term that I hate.

• 1:14:33Speaker 00

  I hate when anyone says, which is, it is what it is. I don't believe that to be true. I hate that expression is what it is. What does it even mean? It is what it is. It means that like somehow you were just, this thing happened, you're just accepting it. You can change your own fate. You can change your own life. You can change everything about everything around you. I want my kids to see that that is not the way to live, that living with great intentionality is important. And anyway, jury's still out on that. We'll see what, how, how, how they turn out, but so far they're pretty good kids.

• 1:15:03Shane Parrish?

  I think you're, you're really hard on yourself. What does high agency mean to you?

• 1:15:09Speaker 00

  I don't think you have to have the glory without the, the high agency. Meaning I like people that take deep responsibility for things. This idea, you know, back to expressions that I hate, well, that's not my job. That is an expression I loathe, especially like in, in a setting of a company. I, I just, I don't believe that. I don't think that's, and frankly, at any stage of company. I mean, there are sometimes where like that literally is someone else's job. I get that. But high agency is someone that sees a problem and says, I'm going to fix it. And then fixes it themselves, that they take, they put themselves in, into the role of single threaded owner, responsible person.

• 1:15:51Speaker 00

  I take high agency in everything that I have. It's actually a great term. I actually don't think about that term that often. I love that term. I think the people I admire most all have high agency. They see something, they, they take responsibility for it. Which means that if it goes well, it's, it's, it's their win. It doesn't go well, it's their loss. But they're able to, they have the levers in their hand. They're able to maneuver those levers however they best see fit and they're willing to accept the consequences of those results.

• 1:16:27Shane Parrish?

  Funny anecdote tying together parenting and it's not my job, which triggered this memory. I mean, I once asked my kids, I think they were seven and eight at the time. I was like, okay, go clean the bathrooms in the house and they knew how to do it. So asking them seemed appropriate. And my eight year old looked at me and he's like, uh, that's not my job. Tess, who was our house, you know, the lady who cleaned our house every couple of weeks. He's like, that's Tess's job. And I remember just sitting there for like a brief second and I was like, what do I do in this situation? So I like picked up my phone. I called Tess and I said, Tess, you don't have to come in tomorrow. Don't worry about it.

• 1:17:11Shane Parrish?

  You're going to get paid and the kids have volunteered to do all of your, all of the stuff that you normally do for us.

• 1:17:18Speaker 00

  Amazing.

• 1:17:19Shane Parrish?

  And so I made this list and it was like long and I was like, you can't do any iPad, no movies, no anything until this list is complete.

• 1:17:28Speaker 00

  Guess what? Now it is your job.

• 1:17:29Shane Parrish?

  And not once since that day have they ever pushed back when I asked them to do anything around the house or help out. They're like, no problem.

• 1:17:36Speaker 00

  Yeah.

• 1:17:37Shane Parrish?

  Of course.

• 1:17:38Speaker 00

  I think it's, look, and it's not that your, your son was saying something wrong.

• 1:17:42Shane Parrish?

  No.

• 1:17:43Speaker 00

  He actually thought it was.

• 1:17:44Shane Parrish?

  A hundred percent.

• 1:17:45Speaker 00

  Which is why again, like. It's this crazy paradox, like we work so hard to give our kids these great, these great lives and make their lives better. But ultimately, we don't want to deprive them from the things that actually will give them their own satisfaction later on. I have, you know, without naming any names, I have two, two people that are close to me that are both third generation. Kind of big families, meaning, you know, each of their parents, I think, were billionaires. Okay, very wealthy people. And in both cases, so I know the third gen in both cases. One of them is one of the hardest working people I know. The other one is not at all, like the opposite, super laid backs. And they're both very happy people. They're both wonderful people.

• 1:18:30Speaker 00

  But it's fascinating to me. How both of them are third gen, yet. Completely different. And it's all about the values they set. One really wants to prove that. He was able to, you know, he benefited from the past two generations, but he's going to make his own mark in the world. Making his own mark is deeply important to him because he wants to have personal meaning, personal accomplishment. The other one is like, look. I basically won the lottery, so I'm going to, I'm going to enjoy life more than anybody else because like. I don't even know how this happened, but I'm going to enjoy it. Neither of them are wrong or right.

• 1:19:10Speaker 00

  But I'm fascinated by how parenting translate into ambition and translate into meaning and conviction. I think a lot about that.

• 1:19:19Shane Parrish?

  I don't know. I definitely, I'm a little ahead of you with the kids' ages, but I definitely do not have any answers to that. One of the only pieces of advice Charlie Munger gave me about parenting over dinner once was. The parents that try to artificially impose a different lifestyle on their kids than they are living. Uh, and he gave an extreme example of a guy getting like chauffeured to work with a driver and then telling his kids to get a job.

• 1:19:46Speaker 00

  Very Charlie Munger version of this.

• 1:19:48Shane Parrish?

  Uh, McDonald's, right? And he said that that does nothing but cause resentment.

• 1:19:52Speaker 00

  Yeah, because then again, now you're creating something artificial. It's not, it's not, it's not real. I want them, you know, I, I want them to, I want it to be real. I see that, actually. I set up my new DJ booth in my house. And every time I DJ, I can almost count it. Like, within 30 seconds, both kids will come up and say, "I want to DJ too."

• 1:20:11Shane Parrish?

  Amaze me.

• 1:20:12Speaker 00

  I could have bought them DJ equipment for themselves. That's sort of a, I don't know, like a rich dad thing to do. Like, "I'm DJing. I got DJ equipment." No, instead, they see how much fun I'm having DJing. And I love DJing. I put it on Instagram stories every Sunday. A couple different mixes that I do. But they watch how much fun I have, and then they want to do it. And now they're asking me, "Do I have DJ equipment?" And of course, my answer is, "Well, you should save your money." Like, you can do chores, and you have birthday money, and all that. Eventually, you can save your money. And I will go with you to the store. We'll buy, we can buy DJ equipment for you. But I never would have been able to to inspire them to think about this thing called DJing and music if I was just throwing it at them.

• 1:20:56Speaker 00

  Rather, by showing them how much I enjoy it, they seem to gravitate to it way more.

• 1:21:01Shane Parrish?

  I love that.

• 1:21:01Speaker 00

  Yep.

• 1:21:02Shane Parrish?

  I want to come back to something we talked about earlier in terms of trying to be great and intentional at everything you do, which means you have to pick and choose what you do. One of the things that you've talked about in the past, we've never talked about, but you've talked about in the past, is sort of your calendar management system for prioritization. And I often had this theory before I heard your story. And I, people would, when I ran a team for the government, people would tell me their priorities. And I'd be like, "Show me your calendar." "Don't tell me your priorities. Show me your calendar." Talk to me about how you use that to set priorities and then audit that you're spending time on the right things.

• 1:21:46Speaker 00

  Well, the audit's an easy one, because I'm fairly compulsive about auditing my calendar once a quarter. And I do that with my team here at Shopify. I also do it with Lindsay, with my wife. So like, Lindsay is also deeply involved in sort of in diarizing my priorities. I calendar everything. I calendar this interview we're doing together. I calendar what I'm doing between now and our dinner tonight. I calendar our dinner tonight.

• 1:22:13Speaker 00

  I find that putting everything into my calendar, even though it sounds ridiculous to have like walk with wife or meditation. I want to meditate more. I have anxiety. I've managed it really well, but part of how I manage is through meditation. Show me, you want to see my priorities? Show my calendar. Every morning, there's a calendar. I do eight minutes a morning. There's a calendar reminder about meditation. It's in the calendar. It's permanent. It's always in there. It's been there for years. So I think most people use their calendar professionally, but they don't want to use it personally.

• 1:22:53Speaker 00

  It almost feels, I don't know, it feels icky to them or it feels too overly prescriptive and formal. It's not me. Everything is in there. It's really, really important. Years ago, someone sent me the Paul Graham Makers vs. Managers time, which effectively is that, you know, the way that at least Paul Graham describes it is that he's got these blocks called managers time, like they're 30 minute blocks, and he has makers times, which are a lot longer for deeper thinking times. So I do that quite a bit and I try to kind of bundle my meeting days on certain days, usually Monday, Wednesday, Fridays, and then more of my like my maker days, Tuesdays and Thursdays, where I can have long form blocks of time to do thinking, to do writing, if I'm writing a speech, or I'm now preparing for Shopify Summit, which will bring a whole

• 1:23:38Speaker 00

  team together, I have to write my keynote. I'm just, I'm intentional about that stuff. I don't think there's any other way to do it. What I also find is that I color code everything. And so what I can do by color coding everything is that I can see like, last night, Lindsay and I had dinner with another couple, it was really great, but that was color coding in purple, sort of social dinners. And when I'm looking on a Sunday night reviewing my week and I see a lot of those social dinners, I'm like, I think this week is a little too heavy. And so now I can sort of adjust, okay, like I'm okay to have one social dinner during the week. I can have two or three of those. I'll just like, I need to, I need to preserve my own energies as well. The color coding thing is really helpful because you can see visually that like where are my, where's my time going?

• 1:24:20Speaker 00

  Jesse Itzler, I don't even know Jesse, he's the founder of Marquee Jet. He's married to Sarah Blakely, who created Spanx. But I did an endurance race that he created called 2929. It's called Everesting. Effectively, you, there's like 12 of them, but you climb these mountains and you emulate climbing Everest, which is 29,929 feet. And I did the Everesting race last September, I'm doing it again this year in Mont Tremblanc. And so I got a chance to meet Jesse and spend some time with him and also kind of I now follow him on social media. And he's got this thing called the big ass calendar. It's literally a big ass calendar. And part of the reason why, it's actually, he sells it on Shopify, it's pretty cool. But the reason why he does it is because it's in his office on the wall and he can see literally 365 days,

• 1:25:05Speaker 00

  everything visually. And what he starts doing, which I really love, and I've tried this a little bit, although I don't have it on printed out, is he'll start the year by saying, okay, what are the most important things? So we'll put in like, like school graduations, or birthdays, or earnings calls, or whatever is important then. And then he'll add to, okay, trips, add the trips in. And once you actually have everything visually in front of you, now you're able to sort of take a stab at it and say like, okay, now you see my calendar, do you see my priorities? If I want to, if I want to get better at like running, where's the running stuff in there? If it's sporadic, it's obviously not a priority. And there is this, you know, I think lying to yourself is like, is kind of insane. That's really where stress comes from, I find, I think that stressing, stress like comes from like,

• 1:25:50Speaker 00

  when like fundamentally your mind and like your body like are just not aligned very well. And when you look at something and you keep saying, I'm really going to get into tennis in 2026, and you're looking at your calendar and there's like not much tennis on it, you're like, obviously, it's bullshit. Like, I'm lying to myself, it's not that important. And I think the calendar, and especially like, the great part about a digital calendar is you have it always on you. It's always synced everywhere, your iPad, your desktop, your laptop, your phone. You have it everywhere available to you, you can add people to it as well. It just makes everything so much easier. Now, now for the downside. It can also be a burden. I'm taking the kids, it's a long weekend here, and I'm taking the kids, Lindsay and I and the kids are going to New York this weekend.

• 1:26:34Speaker 00

  And we want to go see Broadway shows and like, we're huge foodies, wanting some great restaurants. Taylor Swift's new restaurant, favorite restaurant is going to Corner Store, I want to go there. And my wife and I like, I want to do a spin class and all that. So if you were to look at my New York calendar coming up for this weekend, you would look and you're like, dude, like you're missing out on life. There's no room for serendipity. There's no room for you just getting lost in Central Park. There's no room for you just turning down the wrong street in Soho and finding a really cool boutique and a great sneaker shop. There's no room for, you know, I don't know, your kids like you taking a nap randomly. And that's true. That's not me. I'm not the sobriety guy. I'm not the serendipity guy.

• 1:27:18Speaker 00

  I know who I am. I'm the type of person that wants to see my calendar for the next four days and be like, it's all on there. Because that's what gives me joy. And for other people, they would find it to be completely anxiety inducing, but that's not who I am. So I think being honest about the types of things that like you're into and how you want to live your life and then reflecting it and manifesting it in a way that like actually allows you to create these guardrails is super, super helpful.

• 1:27:44Shane Parrish?

  I appreciate that as a

• 1:27:46Speaker 00

  You do that as well?

• 1:27:46Shane Parrish?

  Yeah, I don't calendar sort of like go for a coffee, but you know, every morning nine to 12 is usually blocked off. There's no meetings. I tend to schedule things around energy. So like things I don't appreciate or like doing as much tend to go in the afternoon when I'm lower energy than in the morning.

• 1:28:05Speaker 00

  I'm glad we're recording this in the afternoon.

• 1:28:07Shane Parrish?

  Yeah, that's what I meant. I mean, like lawyers or accountants or like reviewing things, you know, those are high energy tasks for me. And but I've never thought about sort of like starting the year and putting in the most important dates first. I don't really use color coding to the extent that I probably should.

• 1:28:25Speaker 00

  And it just helps on the visual side of it. Like why is there so much green this week? You're like, what's green? Oh yeah, green is like, whatever, you know, extracurricular, like there's too much green, like, you know, I, I, something's wrong here. It just allows you to just have the like holy shit moment. Something is off here. There's no balance here. For me, my calendar needs to look like a rainbow. If it looks like a rainbow, I know that I have this balance like that I'm I myself I'm looking for.

• 1:28:51Shane Parrish?

  I love that. I want to come to AI and how it's impacting the workforce that you guys have, how it's impacting other things. But let's start with Toby put out a memo. And we've talked about this sort of like texting and so the memo came out and he put it out there. He said, basically, if you're not AI by default, you're in a lot of trouble.

• 1:29:12Speaker 00

  Yep.

• 1:29:13Shane Parrish?

  Talk to me about that.

• 1:29:14Speaker 00

  He actually said something different, which he said that if you are not using AI reflexively, which is a very interesting term to use, right? By default is one thing, reflexively is different, meaning in your jobs, everyone that's listening and watching, when you have a problem, you're working on a challenge, a project, are you reflexively thinking about what tool exists right now that I can pull down to help me do my job better? And that's, I mean, that memo obviously got leaked. It was an internal memo that he sent to the whole team. And he's done this before. I mean, you know, historically, I guess quasi famously, he did a memo about Shopify mobile, that like, we were still living kind of in like the desktop world.

• 1:29:56Speaker 00

  And it was clear that e-commerce in particular was moving more to a mobile device, that more traffic was coming. And but Shopify was still building kind of in this like web browser based, you know, desktop world. And so he wrote this, he wrote a memo to the company and eventually it also got leaked. So maybe the story here is that a lot of things when you're a big company, you get getting leaked. But it was an important memo because it was a reminder to the company that like, look, this isn't just some random new tool. This is a new type of programming language. This is a fundamental paradigm shift in the way we all work. And whether you are a storyteller where before I'm preparing for something and I'm like, hey, I just, I want to check a couple of things, like here's the stats that I have. I can throw it into, I like to use perplexity or I actually really love Claude for projects.

• 1:30:41Speaker 00

  I'm personally use Claude, but for Claude, what I do is I have like, I have a project for like health and wellness. So every blood test I have, I upload there. Actually, Toby kind of showed me how to like, how to create these projects in a really interesting way that has these great triggers. And so somebody comes in over email from my doctor, blood test, I put it in there. Or I'll have one around speaking. So I've uploaded every one of my transcripts of speaking. And so I can write something and I can put it into Claude and I can say, from a tone perspective, does this sound like me? Like what parts of this doesn't, doesn't, you know, doesn't feel like my other talks? Or have I told this story before? It's this amazing tool. So I think what, what he does so well is like, he is the

• 1:31:22Speaker 00

  He's the Overton window shifter and he like, he kicks that window hard. And so he just wanted to make sure that at Shopify, if you work here, you are within the like, the origin window of AI like being reflexive is deeply met in the culture. Something else happened. Um, in February of this year, I had our, um, we did our Q4 earnings call. So Jeff and I, our CFO, were on the earnings call. And then there were a bunch of reports, the analyst reports come out after the earnings call and stuff. I think we have like 46 or 47 analysts covering Shopify. And a bunch of the reports mentioned on the, actually criticized me for saying, and also we were surprised that Harley did not talk more about AI.

• 1:32:07Speaker 00

  And I was like, it's like, this is weird. Like, what, like two or three reports came out like that. I was like, this is strange. So I listened to the call again and I listened to a lot of other calls too. What I realized was, I get it. All these other companies that reported around the same time as we did, they basically spent 50% of the call talking about AI. Our AI investments, what AI is going to do for our customers. It was like, if you sort of word clouded the earnings call scripts, by far AI would have been the largest cloud. And it wasn't for us. It was, I mentioned, I talked about Shopify magic and all that. And it dawned on me that the reason that we were, I was criticized, we were criticized for this was that like, I think a lot of companies are very hand-wavy about AI.

• 1:32:52Speaker 00

  Like AI is going to change our company and, and it's going to like, you know, it's like that poster of like an eagle with leadership underneath and people like, what's our culture? It's that poster. No, that's not like, that's a stupid poster. Culture is like what people do, how people feel, what, what, what happens when no one's watching. What is, what does the team do? That's real culture. Putting a sign up is, is, is completely superficial nonsense. Well, a lot of companies are sort of talking about AI right now in a similar sort of superficial con, like nonsense kind of way.

• 1:33:24Speaker 00

  Ultimately, if you think about the mission of Shopify, it's we want to create more entrepreneurs. We want to make entrepreneurship more accessible. We want more people to use it to whatever their version of success is. Maybe it's to be the youngest billionaire in the UK like Ben Francis and Jim Shark, or maybe it's just to afford, you know, hockey equipment. But we think that entrepreneurship allows anyone to do that. It's the great equalizer.

• 1:33:49Speaker 00

  The unfair advantage that like unfair, like big unfair advantage that large companies have over small companies is headcount. That they have a lot of people. And so they have a lot of people doing a lot of different jobs.

• 1:34:07Speaker 00

  As easy as we've made entrepreneurship, there's still that.

• 1:34:11Speaker 00

  There's still a resource constraint if you are a one man or one woman or a one person operation. You don't have a lot of different teams.

• 1:34:20Speaker 00

  What we think is so fundamentally game changing and, and mind blowing about AI is that

• 1:34:30Speaker 00

  we are actually one of the companies, I think, that's best positioned to utilize it to create this like step function advantage for the people that you shop with, especially the small businesses. This idea that we don't have an AI product, or rather AI is built in all across Shopify, I think is absolutely incredible. On Big Shot, I interviewed Mickey Drexler. Mickey Drexler ran The Gap for 20 years. Do you know Mickey? Yeah. Have you had him on the show? Yeah. You have him? Okay. Amazing guy. As you know, he can tell stories forever. So Mickey told me that when he was at The Gap, The Gap had these like massive merchandising teams and product photography teams. And as he was telling me this, the first thing I thought about was, oh my God.

• 1:35:13Speaker 00

  If you compare Mickey Drexler running The Gap in 1997, 1998, doing billions of dollars, a one person operation at their mom's kitchen table right now on Shopify, who needs to write a product description, who needs to do product photography? I suspect that today they can have a higher converting, a higher, a highly optimized or higher optimized product description and a better product photography taken. than Mickey's 300 person team. That to me is like the ultimate, that's what like, that's why AI matters to Shopify. It's not about the hand wavy, all this stuff and earnings call, word, word cloud bubble stuff.

• 1:35:56Speaker 00

  It's about can we actually even further bend like the learning curve and the barrier to entry into entrepreneurship? Nothing quite does this like AI does. Now, it doesn't mean you can effectively set it like, set it and forget it, but it just means that it's going to be a huge mass advantage. And I think the way that we're doing it is not simply by having one AI product, but rather literally embedding it across all of Shopify. I think that's going to be. From a trajectory perspective, you will see a pre and a post trajectory of business growth, particularly small business growth because of AI relative to almost every other technology that came out.

• 1:36:34Speaker 00

  I mean, it is, it is so substantially valuable for small teams because it puts so much of their, it gives them so many more resources in a way that they would never have unless they had bigger teams. And ultimately, if you think about like, as a consumer, you are buying a T-shirt, you want to buy the very, very best T-shirt. You don't really care if the T-shirt company has 300 people or three people, you care about the T-shirt itself. But unfortunately, that 300 person company historically was able to get in front of more customers because they had merchandising teams and marketing teams and product photography teams and all types of other teams. But now that three person team can actually do as much as the 300 person, in fact, maybe they can do it better. And I think that is going to be remarkable.

• 1:37:18Speaker 00

  So I think from, I think from a Shopify perspective, I think our merchants will get a lot better and grow a lot faster because of it. But I think the companies that are able to adopt, and this is really the like, the crux of the, like, everyone was surprised by that memo that Toby sent out. We were not, like, most people at Shopify were not surprised by that. It was the most Toby memo. It was like, I want to be clear, everyone's talking about AI, but what does it really mean? It means that if you work at Shopify, the expectation is that you use it reflexively. The expectation is before you go and try to hire another person for your team, you ask yourself and you, you test whether or not some sort of AI tool can actually do it better for you. And if it can, that's what you should be doing. I mean, the teams and the companies that embrace that are going to be far more successful than ones that.

• 1:38:03Speaker 00

  Adopt it with some, you know, mediocre energy.

• 1:38:08Shane Parrish?

  I was talking to my kids the other day and I was like, you have a thousand employees at your fingertips.

• 1:38:12Speaker 00

  Yes.

• 1:38:13Shane Parrish?

  And they were like, what do you mean? It was like, all these GPUs, they work for you.

• 1:38:16Speaker 00

  Yes.

• 1:38:17Shane Parrish?

  They do exactly what you ask them to do and they do it better.

• 1:38:20Speaker 00

  For 20 bucks.

• 1:38:20Shane Parrish?

  In a lot of ways than most humans do at this point.

• 1:38:23Speaker 00

  A hundred percent.

• 1:38:24Shane Parrish?

  And especially with different models coming out and evolving.

• 1:38:28Speaker 00

  That's right.

• 1:38:28Shane Parrish?

  It's fascinating to me. What do you think the impact will be on Shopify in five years? Like internally, not for your merchants, but like, do you need 10,000 employees? Do you need like, how does this change the, the dynamic?

• 1:38:43Speaker 00

  I mean, in terms of size of company, I, I think the size of our company right now and the shape of our company right now is, is, is, it's really good. Like, we are very happy with the size. It means we can do more with, with, with the same amount of people. It means we can go into new areas. It means we can build faster. I think, not just for Shopify, but I think the companies that are going to be, that are going to embrace it, not utilize it, but truly embrace it and make it part of their daily flow. I mean, look, we talked about schedules and, and, and prioritization just before. Once a quarter, when I had time, I, I go and look through my calendar. I can now create a very simple, like, agentic tool that basically looks at my calendar every week. And on Sunday it says, dude, you've got too many social things, or dude, you've got too many one-on-one meetings, or like, whatever it is. I can be, all the things that I want to do in my life, I think can be made better for that.

• 1:39:29Speaker 00

  One of my mentors is a guy named Aldo Benson. Aldo's 85 years old. He was a Moroccan immigrant to Canada. He built Aldo Shoes. He's, you know, he's, he's built a multi-billion dollar company. And Aldo and I were giving a talk together. At, he just gave a bunch of money to McGill to create the Benson School of Retail. Faculty of Retail at McGill, which is, I'm involved with a really, really cool faculty. And we're on stage and I said to Aldo, I'm sort of like, Aldo's kind of an old school guy. And I said, Aldo, what do you think of AI? And I was kind of like, it was a bit of a joke. I was kind of poking fun of like the young guy, like the young retail guy poking the old retail guy. And Aldo, without skipping a beat, says it's like having a best friend in your pocket.

• 1:40:13Speaker 00

  This is an 85-year-old man. He's seen, you know, he's seen everything. He's seen all new technology for the last, you know, in and a half decades. But even the fact that he can appreciate how much leverage you get with this new technology, I think, I think is amazing. So I think it'll make us move faster. I think it'll allow us to build stuff with smaller teams. I think it'll allow our merchants to make better decisions. I, I think you're going to see, you know, I'm, I'm blown away even pre kind of some of these large language models and AI tools coming out in the last four or five years.

• 1:40:48Speaker 00

  I'd been, I've, I've, I've found it to be remarkable that these companies have started in 2014 and become billion-dollar companies in the last 10 or 11 years. Typically, business doesn't happen like that. It took decades to become hegemonic, to become the leader in your category. And now you have companies like, I don't know what to go to, Viori, ALO Yoga. These companies didn't exist a decade ago, and now they are absolutely unequivocal category leaders. It's wild. It took them like less than 10 years. Figs completely disrupted Trina and Heather completely disrupted the hospital scrub industry. You walk in any hospital in North America, maybe in the world, and you look around and see like what most doctors are wearing or nurses are wearing, it's Figs.

• 1:41:31Speaker 00

  That didn't exist a decade ago, and now they're publicly traded, multi-billion dollar company. So I've already been, it's been astonishing for me to watch from this perspective. Shopify basically runs about 12% of all US e-commerce. So if you were to think about like, just in terms of size-wise, like we're like the second largest checkout on the internet, in the US at least, but in other countries, maybe even more so than that.

• 1:41:55Speaker 00

  The trajectory of business growth has been so remarkable, so fast. 10 years, you go from an idea to a multi-billion dollar publicly traded company. Now you add on this like layer of AI, which means you can make better decisions faster. You can make smaller teams way more productive. I think you're going to have another step function. Like I think that you will have this incredible hockey stick curve of businesses that grow from zero to $100 million in GMV inside of three years instead of, instead of, inside of like 10 years. And I mean, I pray at the altar of entrepreneurship and there's been a couple of things over the last, you know, 50 years that has made it much better. Obviously, the internet's made it much better.

• 1:42:36Speaker 00

  Obviously, things like Shopify has made it much better, but I think like this new era where you have all these things stacked with AI.

• 1:42:45Speaker 00

  It is the golden age of entrepreneurship and I'm I'm here for it.

• 1:42:48Shane Parrish?

  I think a lot of people our age are in more trouble than they realize if they're not using it. And I say this because I had dinner with a few friends the other night and the subject came up and I was like, how is everybody using AI? Like, I'm always interested in how other people, like you were talking about sort of like putting your blood test results in a project and I'm like, I'm trying to learn from other people. And almost all of them were like, oh, it hallucinates, so I don't use it very much. And I'm just like, wow, like that's. And then they're like, what are you doing with it? And I go on for like 10 minutes, right? Like I'm coding, I haven't done that in like 10 years. I'm doing all these things with it and they're just like, wow.

• 1:43:27Speaker 00

  I mean, you can literally generate a Python script right now in a matter of 30 seconds with OpenAI right now. You can generate, you can build an app in a matter of like, I mean, back to what you just said.

• 1:43:39Speaker 00

  That reaction of I tried it once, it hallucinated.

• 1:43:44Speaker 00

  I think one of the things that you have to have if you're going to be successful in this new era of business and and actually in any in any era with all this technology is you have to be a techno optimist. You have to believe that things are getting so good at such a quick pace that it doesn't matter that it hallucinated, that the next time you use it, it probably won't hallucinate. And I think if you get stuck in this trap of it hallucinated once, therefore I now have scar tissue, I'm not going to use it. You're going to fall behind. It's one of the reasons why one of my mentors has, I think one of the reasons he spends time with me is he loves hanging out with people younger than him, much younger than him. Forty, thirty years younger than him. And he used to run one of the largest companies in Canada. He's an amazing man.

• 1:44:29Speaker 00

  And I always noticed that, that like, he's always hanging out with younger people. And I had someone, I said, "You seem to like, you know, you seem to like hanging out with younger people." "Is it because you guys teach me stuff?" He's like, "My friends don't teach me as much." "These, my friends are in their sixties and seventies. We talk about golf, we talk about whiskey or wine, whatever." "But when I hang out with you, Harley, you tell me about like, the new DJ equipment and how like, it's all powered by AI." "And you tell me about this new stuff." And then he goes one step further. He's like, "And he also has friends that are in their twenties." "And they tell me about all types of new technology." "And I think there is this, there's something, maybe this is one of the great parts, but, but like, one of the advantages of having kids, "is you see how they're interacting. You see what they're doing." You know, I sent a note over to David, who's the CEO of Roblox.

• 1:45:10Speaker 00

  And I was just explaining to them that the way my kids use Roblox is actually, "Yes, they're playing a game, but rather, the game is almost passively in the background." "They're having a conversation, and rather than looking at each other, they're looking at this game together, kind of playing." "But the actual, in, in, at least for my kids, who are, you know, who's a Bailey's eight years old, "Roblox for her is simply a central chatroom."

• 1:45:34Shane Parrish?

  Yep.

• 1:45:35Speaker 00

  "It is not actually about the game itself." "And rather than staring at the person's face on screen as being the main focal point, "you know, the face is kind of in the bottom right corner, the main focal point is in some random game." "And, and rather, you know, it's maybe, and David, of course, knows this, but, "I was like, what you've created is like, a social network." "And like, you call it a, you know, a game ecosystem and all that, but, "watching how people are using this technology is remarkable." "And it's, I think if you are a techno-optimist and you're paying attention to all these things that are happening, "it is tough not to be incredibly optimistic about like, where we are and the world we're living in right now." "It's, it's amazing."

• 1:46:16Shane Parrish?

  I could go on for another couple hours. I think this is probably a good moment to sort of wrap this up. We always end with the same question, which is, "What a success for you."

• 1:46:26Speaker 00

  I think about this term, I mentioned a few times, life's work. I think about this term joie de vivre, which is joy of life, which is a beautiful French term that is, you know, for me, like Montreal is the joie de vivre capital.

• 1:46:41Speaker 00

  I want more of those things in my life. I want to do more of my life's work. I want to have more joie de vivre in my life. And I don't want to, I don't want to sacrifice either of those things.

• 1:46:53Speaker 00

  I think that's what success looks like. The, the harmonization of joie de vivre and life's work would be,

• 1:47:02Speaker 00

  that would make me successful, I think.

• 1:47:04Shane Parrish?

  That's a beautiful answer. And we'll have to do part two because I got a million more questions.

• 1:47:08Speaker 00

  Thank you, Sharon.

• 1:47:09Shane Parrish?

  I appreciate it.

• 1:47:09Speaker 00

  Appreciate it.

• 1:47:10Shane Parrish?

  Thanks for listening and learning with us. Be sure to sign up for my free weekly newsletter at fs.blog/newsletter. The Farnham Street website is also where you can get more info on our membership program, which includes access to episode transcripts, my repository, ad-free episodes, and more. Follow myself and Farnham Street on X, Instagram, and LinkedIn to stay in the loop. Plus, you can watch full episodes on our YouTube channel. If you like what we're doing here, leaving a rating and review would mean the world. And if you really like us, sharing with a friend is the best way to grow this community. Until next time.