The President of Shopify on AI, Scaling, & High Agency | Harley Finkelstein

Finkelstein predicts that AI-enabled businesses will achieve hockey-stick growth curves much faster than the current baseline—going from zero to $100M GMV in 3 years instead of 10 years, creating a new generation of category leaders.

“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 hund00 million in GMV inside of three years instead instead of inside of like 10 years. And I mean I pray at the altar of entrepreneurship and there's been a couple things over the last you know 50 years that has made it much better.”

Young brands (Viori, Alo Yoga, Figs) that didn't exist a decade ago are now billion-dollar public companies and category leaders, proving the acceleration of entrepreneurial success timelines.

“companies like I don't want to Viori, Alo Yoga. These companies didn't exist a decade ago and now they are absolutely unequivocal category leaders... Figs completely disrupted... the hospital scrub industry... it didn't exist a decade ago and now they're publicly traded multi-billion dollar company”

Shopify's core mission is to make entrepreneurship more accessible as 'the great equalizer,' enabling anyone regardless of background to achieve their version of success.

“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 think that entrepreneurship allows anyone to do that. It's the great equalizer”

Moving to Boca Raton, Florida at age 12 was the first time Finkelstein realized that other people had substantially more wealth than his family, triggering a competitive chip on his shoulder and driving his subsequent ambition and insecurity.

“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. 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.”

The Montreal Chauvanel garment district existed as a concentration of Jewish and immigrant apparel makers because the needle trade had the lowest barrier to entry—a sewing machine was all that was required, unlike biotech or pharma which required capital and education.

“The reason you see so many Jewish immigrants go into the schmata business, the needle trade is because low barrier entry. They couldn't go to biotech. Biotech had a high barrier 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 snow a sewing machine and that's it.”

Finkelstein watches his early interviews and is highly self-critical, deliberately studying them to remove verbal tics like 'um' and improve his craft as a speaker.

“now I get to do like the knowledge project. This is like this is a big podcast... I didn't start by doing the Shane Parish podcast. I started by doing a lot of tiny little local podcasts and watching them over and over again... 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 gonna fix this particular issue”

Modern business leadership has shifted from selling commodities (widgets, tires, soda) with interchangeable executives to selling missions and values where the company attracts people whose personal mission aligns with the company's mission.

“Part of what is wonderful about modernday business leadership is that we are not selling widgets. You watch these old school business or even um uh shoot Wall Street uh 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 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.”

Finkelstein's father created business cards for every business idea he proposed as a child, embodying a message that he absolutely had the capacity, willpower, and permission to pursue any entrepreneurial venture, which became foundational to Finkelstein's confidence and willingness to take action.

“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 device that was the equivalent of him saying, 'You absolutely can do this. You are you you have the capacity. You have the willpower. You are you have the entitlement. Like you are you can do this. You have the permission to go do this.'”

The best stories Finkelstein tells start with his personal experience and embed his own narrative (stories from age 13, 18, travel), because personal stories cannot be wrong, are told with authentic conviction and passion, and immediately resonate with audiences.

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

Mentors should not be emulated holistically; instead, identify specific competencies you want and find mentors who excel in those narrow categories, then learn from them in that domain specifically.

“you end up thinking about the idea of a mentor, you end up thinking about the 360 of the mentor... My experience has been that... any any mentors that anyone watching or listening have in their lives, they probably are really good at something like really good... they're probably lacking in other areas entirely... Instead, it's much easier to figure out what are the couple things I want to get good at... and then looking at who's really good at that and ask them specifically”

Finkelstein's family motto 'How you do anything is how you do everything' reflects a philosophy of intentionality in all life domains, from leading a company to cooking dinner to selecting wine.

“our family motto is... how you do anything is how you do everything... There is an intentionality about everything that we do in our lives. The way that I think about um leading this incredible company... to the way Lindsay thinks about cooking dinner to um the wine that I've been thinking about you and I are going to drink later tonight. There's a great intentionality about all these things”

Finkelstein aspires to implement the 'go direct' manifesto in corporate communication, where company leaders directly communicate value to stakeholders (investors, customers, media) rather than relying on intermediaries.

“Lulu is on our board, who's an amazing, uh, probably one of the greatest comm's geniuses on the planet talks about this go direct. She has a famous go direct 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 a it's not an earnings call for me. It's a storytelling opportunity.”

Finkelstein sent a note to David Karp (CEO of Roblox) explaining that how his children use Roblox is not primarily game-play but rather Roblox serves as a social/chat hub where they talk to friends while the game runs passively in the background.

“I sent a note over to David who's a CEO of Roblox 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. They're kind of playing. But the actual in in at least for my kids who are, you know, who's Bailey's 8 years old, Roblox for her is simply a central chat room. Yep. 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, the, you know, the face is kind of in the bottom right corner. the main focal point isn't in some random game”

The unfair advantage large companies have over small entrepreneurs is headcount (large teams doing specialized work), and AI is a game-changer because it lets a one-person or three-person operation have the same productive capacity as a 300-person company in merchandising, photography, marketing.

“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. As easy as we've made entrepreneurship, there's still that 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. What we think is so fundamentally gamechanging and and mindblowing about AI is that 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 use Shopify especially the small businesses.”

Finkelstein notes that companies that merely talk about AI in earnings calls and marketing (using it as a word cloud) without actually embedding it into operations are missing the point—Shopify embeds AI across all products rather than creating one 'AI product.'

“I think a lot of companies are sort of talking about AI right now in a similar sort of superficial like nonsense kind of way. 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 Gym 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...I think Shopify is one of the companies I think that's best positioned to utilize it to create this like step function advantage for the people that use Shopify especially the small businesses. This idea that we don't have an AI product but rather AI is built all across Shopify I think is absolutely incredible.”

Finkelstein doesn't care what his children do professionally (entrepreneur, musician, tradesperson) but demands they have intentionality in their choices; he hates the phrase 'it is what it is' because it implies passive acceptance rather than active agency.

“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 have a 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. I hate when anyone says it, which is it is what it is.”

Being a world-class husband requires overriding his natural tendency to go into problem-solving mode when his wife shares a problem; instead, she often just wants to be listened to, so he created a mnemonic device where he asks her 'Do you want me to solve this or do you want me to listen?' to interrupt his reflex.

“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 it's my whether it's my amydala or my lizard brain, but there's some my reflexively I 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 pneummonic devices which is like I now ask her, do you want me to solve this problem or do you want me to just listen?”

Shopify has a 'trust battery' metaphor where people with high autonomy have a very high trust battery, while people whose batteries have drained cannot be recharged, signaling they should no longer lead.

“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 lead the company it's because their trust battery is so low that like an old cell phone it just cannot be recharged. You don't know exactly are you at 46% or 66%. But you know direction where you're at.”

Finkelstein and his wife Lindsay deliberately studied couples they admired to create relationship mentors—they identified couples with great marriages, spent time with them via double dates to observe their interaction styles, and learned from their example.

“One of the things that Lindsay and I did before we got married was we began to look at the 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.”

Finkelstein and Toby adopted a principle that every Shopify employee should be able to give a keynote at their industry conference about how they do their job completely differently than everybody else—targeting global maximum, not local maximum.

“Every person that works at Shopify should be able to go to their industry conference whatever their cate 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. It is like the local maxima is like like you know you're at the top of the mountain you're doing better than everyone else is doing your job. the global maximum which is like Toby in a nutshell is there's a whole other man over here that's where that's how you re-qualify”

Finkelstein's mentors and role models tend to be 'spiky objects'—people with one or two areas of exceptional mastery and significant gaps elsewhere—rather than well-rounded generalists, and Shopify intentionally builds a team of spiky objects.

“I don't know anyone who is great at everything um the mentors in my life the the role models in my life they tend to be spiky objects”

Toby's feedback style is 'German'—or as Finkelstein says, the 'Jewish mother' version—where when you achieve 98% he asks 'what happened to the other 2%?' This is described as an immigrant trait: compliment coupled with always pushing for more.

“He's much more German about it. Um, 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%.' Um, which actually I've now learned, it's actually very much a um, 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?”

Many speakers try to emulate other successful speakers (Gary Vaynerchuk, Joe Rogan, Tim Ferriss) rather than developing their own authentic voice, but Finkelstein intentionally developed his own style—excited, imperfect, quick-talking, genuine.

“A lot of people end up trying to emulate other speakers. 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 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.”

Finkelstein told his 7 and 8-year-old children to clean the bathrooms; when his 8-year-old said 'that's not my job,' he called the housekeeper, suspended her service for the day, and gave the children a full list of household duties—after that day, the children never again questioned doing chores.

“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 8-year-old looked at me and he's like uh that's not my job. Tess who is our house you know the lady who cleaned our house every couple weeks. He's like, 'That's Tessa'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, uh, you don't have to come in tomorrow. Don't worry about it. 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.' Amazing. 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. Guess what? Now it is your job. 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. Of course.'”

Jesse Iller (founder of Marquee Jet, married to Sarah Blakeley of Spanx) created a 'big ass calendar' where he maps the entire year visually, pre-populates it with non-negotiable events (graduations, birthdays, earnings calls), then layers in secondary commitments to achieve visual balance.

“Jesse Iller, I don't if you know Jesse, he's the founder of Marquee Jet. Um he's married to Sarah Blakeley who created Spanx, but I I did um an endurance race that he created called 2929. It's called Everesting. Effectively, you there's like 12 of them, but you you climb these mountains and you emulate climbing Ever Mount Everest, which is 29,029 ft. Yes. And I did the Evering race last September. I'm doing again this year uh in Mont Trrombla. And so I got a chance to meet Jesse and spend some time with him and also kind of I now follow him on 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 everything visually.”

Getting comfortable with being uncomfortable is a form of magic that Finkelstein has consciously developed—he wasn't born with it, but learned it, and he doesn't know anyone he admires who has succeeded without going through a period of looking dumb.

“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 need to be born with that. I think you can learn that. I think you you can learn resilience, 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 look looking kind of dumb.”

To be successful in the era of AI and new technology, you must be a 'techno optimist'—believing that things are getting so good at such quick pace that one hallucination or limitation doesn't define the tool's future usefulness.

“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 new 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.”

Finkelstein has a mentor (age ~85) who used to run one of Canada's largest companies and deliberately spends time with much younger people (Finkelstein at 41, and people in their 20s) because they teach him new things, while his same-age peers only discuss golf and wine.

“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. I'm I'm 40 30 years younger than him. Uh and he used to run one of the largest companies in Canada. He's an amazing man. 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, uh, you seem to like hanging out with with other people.' He's like, 'Cuz you guys teach me stuff.' He's like, 'My friends don't teach me as much.' He's like, 'My friends are in their 60s and 70s. 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 and then he goes one step further. He's like, and he also has friends that are in their 20s and they tell me about all types of new technology.”

Some Montreal philanthropists use 'entrepreneur approach to philanthropy': they identify specific problems (like a hospital's equipment shortage), calculate total cost including staffing and infrastructure, then raise and implement the precise solution.

“They kind of take this entrepreneur 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'... They'll say 'Great. How much is a second machine?' They'll be like 'It's $2 million'... these people will sort of go away. They'll come back to the hospital. Literally a week later, they'll say 'Great. We figured out that you need a radiologist, need a machine... we think it's $4.5 million'”

Finkelstein believed his father took massive personal risks and risked 5–6 years of federal prison time to provide a better life for him and his siblings, which shifted his emotional relationship from anger and disappointment to deep admiration and empathy.

“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 two much younger one of my sisters is 10 years younger, the other is 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 of federal prison time to provide that for us.”

Finkelstein also wants to be a world-class father and husband, which is more difficult to measure than storytelling because he can't get objective third-party feedback, but it's deeply important that his kids and wife believe he excels in these roles.

“You also want to be a world-class father and husband. 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 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.”

Toby gives compliments sparingly and only when someone has clearly exceeded industry expectations and reset what's possible in their domain, treating baseline performance as non-complimentable and exceptional performance as the only worthy of recognition.

“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 and doing my job really well is the expectation. knocking out of the park going like resetting what corporate storytelling looks like or how to do you know earnings when you do that exceptionally well that's when he says that was a great job”

Finkelstein and his wife avoid creating artificial scarcity or hardship for their children because that would be inauthentic to their actual lives; instead, they model intentionality, respect for service workers, and high standards through behavior that children observe and emulate.

“Lindsay is 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, um we're fortunate to have um 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.”

Finkelstein audits his calendar once a quarter with his team and his wife Lindsay to ensure alignment between stated priorities and actual time allocation, because calendar does not lie—it reveals true priorities.

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

Shopify runs 12% of all US e-commerce, making it the second-largest checkout platform after Amazon, and AI will accelerate the trajectory of business growth because small entrepreneurs can make better decisions faster with less human capital.

“Shopplay 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.”

Finkelstein uses Perplexity and Claude (with Claude Projects featuring health/wellness and speaking transcripts) to enhance his work—asking Claude whether his writing 'sounds like him' or comparing if he's told a story before.

“I like to use Perplexity or um I actually really love Claude for projects on personal views 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 something comes in over email from my doctor blood test I put it in there. Um 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?”

Finkelstein created 'Firebelly Tea' with David Seagull (founder of David's Tea) because Seagull is the most passionate person about tea; once you identify someone deeply passionate about something, they should build a company in that domain.

“Firebelly Tea, my little tea uh uh tea company that I started Dave Seagull... the reason I wanted to start this company with Dave is like there was no one on the planet more passionate about tea. And the fact that David Seagull, who created David's Tea, was not running a tea company... was ridiculous”

Finkelstein wears James Perse t-shirts every day because James Perse himself is obsessed with Japanese cotton, American cotton, GSM counts—he made the products for himself first, so thousands of others now want them too.

“I wear a James Purse t-shirt every day. And today, I'm wearing all James Purse. Of course, James Pur is successful because no one thinks about GSM counts or ri more than he does. No one thinks about Japanese cotton versus American cotton more than he does.”

Finkelstein became visibly unhappy and 'non-exothermic' as COO—not energized as usual—and lost his signature high energy when meeting merchants, causing Toby to notice and suggest a transition to a role better suited to Finkelstein's strengths.

“Actually, I think it became obvious to Toby that like I wasn't very happy. I wasn't being my exothermic self. Mhm. And for someone that's always been exothermic, that's always been high energy, um, in those sort of at the end of my of my, you know, 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 it was clear I was in the wrong gear and it was Toby that identified it and said there's this other thing we could find someone to be the chief operating officer”

Finkelstein has coaches and mentors for specific skill areas, but at some point you stop learning new frameworks from any given coach—you've seen the entire 'toolbox'—and that's a good time to move on to the next coach, which is not a criticism but a natural lifecycle.

“I have a great coach in my life right now. Um it's probably my third or fourth coach that I've had. One of the things I think about coaching and 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 coach is 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.”

Finkelstein became happier and more engaged once he stepped into the storyteller role, and this change was visible enough that his wife Lindsay noticed—even during the COVID period when he was working from home, the role change re-engaged him completely.

“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. Um, even Lindsay would say that between 2020 and 2022, which I use those years because we're still in COVID and like we were 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 areas of responsibility completely re-engaged me”

Finkelstein uses 're-qualification' to describe the expectation at Shopify that because the company is growing rapidly across products, merchants, geographies, and impact, each leader must continuously improve and prove they can keep up; stasis and resting on last year's achievements are unacceptable.

“When you look at the growth of Shopify, which it grows, you know, we've we're growing a lot. Forget sort of the the topline revenue or free cash margin growth or anything like that, 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 may have got you a high five and a boy and a pat on the back and and and a and a whatever all the great stuff that comes along with that, that is not good enough anymore.”

Finkelstein noticed that Cass, who was running Shopify's payments team and reporting to him, seemed to genuinely love operations and was naturally in his flow state with operations—something Finkelstein realized he was not.

“I had someone that that we had hired that that was reporting to me who was running our payments team, Cass. And in almost every interaction I had, it did sort of feel like, man, Cass really likes operations. Like like he just it feels like his ground state. He's kind of always doing it. and and and so I I I saw glimmers of like what people that are truly operationally minded look like.”

Shopify's timing was critical to Finkelstein's ability to become chief storyteller—he could not have done this in 2010, 2013, or 2018 when the company was smaller, but had to reach a particular size where storytelling became a distinct, high-value function.

“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.”

Finkelstein served as Chief Operating Officer of Shopify from post-IPO until around 2021 (approximately six years) because Toby asked him to, not because it came naturally; he was never in his flow state, though he felt important managing large teams.

“I became chief operating officer around the just just post IPO until around 2021 I think so for six years. I did it because that's what Toby asked me to do. Um we'd never had a COO before and and and it was sort of this way of me looking after operations specifically business operations. It didn't come naturally to me. Um, but back to sort of the, you know, lifelong learner and the global maxima thing and Toby pushing me into different directions. I was like, I'm going to 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. Um, I felt very important.”

Every business leader Finkelstein admires is at their company or built their company because they had a personal problem they wanted to solve or a personal experience that shaped their worldview around that product—there is no accident in the alignment.

“There is a deep connection to it. There's I mean Firebelly Tea, my little tea uh uh tea company that I started Dave Seagull that you you're now involved with a little bit. Um, the reason I wanted to start this company with Dave is like there was no one on the planet more passionate about tea. And the fact that David Seagull, who created David's Tea, was not running a tea company, you know, in in in the modern world was ridiculous. All he cares about is tea. Of course, he should be he should start a company. He already started one”

Finkelstein color-codes his calendar to visualize time distribution by category; when he sees too much of one color (e.g., purple for social dinners), he knows the week is out of balance and he needs to adjust.

“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 um last night Lindsay and I had dinner with another couple. It was really great, but that that was color coded in purple. Um 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't have two or three of those. I'll just like like I need to I need to preserve my own energies as well.”

Finkelstein interviewed David Rubenstein about his philanthropy approach and learned that he only funds organizations/projects where he's personally essential (wouldn't start without him, wouldn't end without him, or he can measure impact in a 10-year period), and this informed Finkelstein's own foundation strategy.

“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 or he can see the efficacy of the investment in his in 10-year period and it's deeply personal to him.”

Most people have too much 'cringe pain tolerance'—they avoid reaching out to mentors or asking for help because they worry about appearing foolish or facing rejection—and this fear is the largest blocker preventing people from creating personal boards of directors.

“I will say that uh 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...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 fullon and I will never be disrespectful. But I have zero cringe in my life...And I think that's the largest blocker of why more people don't create these personal boards of directors.”

Finkelstein keeps the original screen print that Ben Francis used to create Gym Shark in his office as a reminder that Francis had multiple failed companies before Gym Shark, illustrating that entrepreneurial success is iterative and that visibility of early failure helps normalize it.

“In my office uh here here in Montreal, Shopify office, I have the original screen print uh that Ben Francis used to create Gym 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. 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 Gym Shark.”

His role at Shopify shifted from Chief Operating Officer (which did not align with his natural strengths) to President and Chief Storyteller (which does), resulting in dramatic re-engagement after years of misalignment.

“I became chief operating officer around the just just post IPO until around 2021 I think so for six years... It didn't come naturally to me... It was never natural to me. Never felt like I was in my flow state... Around 2021/2022... it completely changed my energy levels. It made me exothermic again. It made me excited again”

Toby's internal memo about AI stated that if you're not using AI 'reflexively,' you're in trouble—meaning reflexively applying AI tools to challenges should be the default practice, not an afterthought.

“He actually said something slightly different which he said that if you were 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 that 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?”

Finkelstein's chosen storyline is entrepreneurship (his family story, his friends' stories, Shopify's story all align with this theme); he couldn't effectively tell stories about cars or biotech because they're not his authentic storyline.

“the storyline that I've chosen is entrepreneurship. 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 the story in that way”

Finkelstein aspires to be world-class at storytelling—specifically at taking brilliant things Toby built and communicating their value to investors, media, merchants, and partners—which he believes is the greatest value-add he brings to Shopify.

“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. Um, 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.”

In Street Fighter, characters have trade-off attributes—some are great at defense but bad at offense, some great at jumping but bad at kicking—and life is similar: you cannot be good at jumping, defense, offense, and kicking simultaneously, so you must choose what you want to be good at.

“When I was younger, I used to play Street Fighter. And Street Fighter, uh, 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 in 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.”

Toby's greatest gift to Finkelstein over nearly two decades of partnership is consistently seeing a better version of Finkelstein than Finkelstein sees himself, and reminding him of his untapped potential.

“The gift that he has given me in my career is that he's consistently over uh 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 weeks ago. We run an offsite that there is another gear in me.”

Forced entrepreneurship (survival-driven, like his grandfather's egg stand) and passion-based entrepreneurship are fundamentally different, and modern entrepreneurship has shifted toward the latter as a luxury that previous generations didn't have.

“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. Totally. They did sort of what they had to to life's work. That's a nice, you know, like I can I never said that to my grand ex. 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.”

Some people are 'energy vampires' and others are 'energy catalysts'; geography also has this property (Montreal is an energy catalyst for Finkelstein and his wife), and deliberate selection of whom and where to spend time with matters strategically.

“there are genuinely energy vampires and energy catalysts in humans. Um, there's also energy vampires and energy catalysts even in in geographies... 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”

Finkelstein intentionally sets up his DJ booth at home and DJs every Sunday, posting videos to Instagram stories, partly because he loves DJing but also because he wants his children to see him enjoying something and naturally want to participate, rather than buying them DJ equipment directly.

“I see it actually. I set up my my new DJ booth um 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. Amazing. 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 you DJ equipment. No, instead they see how much fun I'm having DJing and I love DJing. I B I put it on Instagram stories every Sunday. Uh 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 they're asking me about DJ equipment. And of course my answer is well you should save your money.”

Finkelstein believes this is the 'golden age of entrepreneurship' because the stack of enabling technologies (internet, Shopify, AI) combined creates unprecedented opportunity and leverage for founders.

“I mean I pray at the altar of entrepreneurship and there's been a couple things over the last you know 50 years that has made it much better. Obviously the internet has made it much better. 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. Um it is the golden age of entrepreneurship and I'm I'm here for it.”

Finkelstein defines 'high agency' as seeing a problem and saying 'I'm going to fix it' and then fixing it yourself—taking personal responsibility as a single-threaded owner rather than saying 'that's not my job.'

“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 in into the role of singlethreaded owner, responsible person.”

Aldo Bensadun (85, founder of Aldo shoes, Moroccan immigrant) described AI as 'like having a best friend in your pocket'; this shows that even older generations can appreciate AI's potential.

“Aldo Bensadun. Aldo's 85 years old. Um he was um a Moroccan immigrant to Canada. He built Aldo shoes... I said Aldo what do you think of AI... Aldo without skipping a beat says it's like having a best friend in your pocket... He's seen you know he's seen all new technology for the last... eight and a half decades. But even the fact that he can appreciate... how much leverage you get with this new technology”

Finkelstein recently started DJing again and developed mentorship with Alex at Moog Audio shop in Montreal, learning modern DJing techniques like stem isolation (separating drums, bass, vocals, and instrumentals) rather than the beat-counting approach he learned 20+ years ago.

“I started DJing again recently and I so I began talking to there's this amazing shop here called Moog. M OG Moo Audio 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 and ended up meeting one of the DJ guy, Alex, who runs a 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 using new technology? How do you think about fading?' Um, there's something called um 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.”

Finkelstein wished he had children pre-IPO rather than post-IPO so they could see the struggle and understand the difficulty of building something from nothing, rather than only knowing post-success life.

“I I spent a lot of, you know, this is kind of weird, but I kind of wish I had kids preipo rather than post IPO. Why? I think whatever success that I've had and success of of of the things I've been involved with, 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 I've done in particular with Shopify.”

Finkelstein believes people of his age (40s) who aren't using AI are in 'more trouble than they realize' because adoption is moving fast and those who don't experiment now will fall behind.

“I think a lot of people our age are in more trouble than they realize if they're not using it.”

Finkelstein notes that many people dismiss AI because they tried it once, it hallucinated, and they decided it's unreliable—but this misses the point that AI is rapidly improving and the next time they use it, it probably won't hallucinate.

“I had dinner with a few friends the other night and this 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 include and I'm like I'm trying to learn from other people and almost all of them were like ah it hallucinates so I I like 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 I'm coding. I haven't done that in like 10 years. I'm doing all these things with it.”

Toby is the source of the re-qualification energy at Shopify—he relentlessly pushes himself to be the very best at product and technology, and this pushes everyone else to continuously ask 'is there another gear in me?' and improve.

“The source of that energy is Toby. There is probably no one that I've ever met on the planet. I've worked with Toby now for almost two decades. You know him very well, too. He's a friend of yours as well. There is no one that pushes himself to be the very best at product and technology the way he does. And so, he inspires all of us to to just continuously say, 'Okay, last year was pretty good. This next year, I think I can like I think there's another another year left.'”

Finkelstein's Builder Sundays initiative opens Shopify offices to outside entrepreneurs, and his children observe him asking people how he can help, demonstrating problem-solving and entrepreneurial thinking in action.

“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 uh that's an entrepreneur can come in and work from here. And I come in almost every Sunday. And I bring 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.”

Toby gave Finkelstein permission to step down from COO by validating that storytelling was 'totally enough' and 'super important,' allowing Finkelstein to recognize that the Venn diagram of what he loves, what the world values, and what he can be paid for all overlapped perfectly in the storyteller role.

“Toby almost gave me the permission to say this other thing that you think is maybe not enough, it's like it's 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 ven diagram of what I love doing, you know, like it's like the icky guy almost perfectly described like what do you love? What is the world value? What can you get paid for?”

Toby's mobile memo (from when Shopify was still web-focused) signaled a paradigm shift—that mobile wasn't just a channel but a fundamental platform change—and the memo (which leaked) was a reminder that major technology shifts require active cultural re-orientation.

“Historic I've guess quas famously he did a memo about Shopify mobile that like we were still living kind of in like the desktop world and it was clear that e-commerce in particular was moving more to a mobile device that more traffic was coming and but Shopee was still building kind of in this like web browserbased 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 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”