Shopify President Harley Finkelstein on AI, Antisemitism, Israel, and Jewish Success

One generation ago, my father was a poor Hungarian immigrant who escaped persecution. His grandparents were Holocaust survivors. They immigrated to Debrecen in Hungary. Then the Hungarian revolution happens in the early to mid-50s. It gets really bad again for Jews. And then in the middle of the night, they escape Hungary and find their way to a boat and spend weeks traveling on this terrible vessel to Canada, which let in 40,000 Hungarian refugees. My father was that person. He gets here. My grandfather tries, doesn't have any money, doesn't speak the language, has no education, and my grandfather opens a little egg stall called La Capien at the Jean Talon Farmers Market here in Montreal.

And he worked seven days a week his entire life. The fact that a generation later, his grandson, my father's son, was able to build a company worth well over a hundred billion dollars makes me really proud. And my grandfather is not around anymore to see this. My paternal grandfather, but my maternal grandfather, who was born here, who was a peddler his whole life, is around in my life. I'm very, very close to him, and he sees my success. I see it in his eyes, just the way that he thinks about our family's journey, that he started with nothing. He sold schmattas in the back of his car. And it changes the dynamics of what it means to be successful. It means it's not just about you. It's about long-term legacy. It's about positioning the family in a way that my grandparents could never even imagine. My wife and I recently moved from Ottawa, Canada, where we started Shopify, to Montreal, which is our favorite city in the whole world. We moved here about two years ago, and our parting gift to Ottawa was we built the Finkelstein Jewish Center. We had the opening in October 2025. We had the ribbon-cutting ceremony at the Finkelstein Jewish Center. My parents were there, my family was there, the prime minister of Canada was there, all the major people, the mayor of the city was there. It was a very special moment. I got on stage, and I had been thinking about this speech for years: what am I going to say when it's finally time to open this? And I asked everyone to look at the building, and I said, 'This building is not a symbol of success. It's not a symbol of hard work. It's not a symbol of entrepreneurial strategy. This building is a symbol of survival.'

Perseverance. This building is the Jewish story: two generations ago, my grandfather was sitting in a concentration camp, and now I'm putting up buildings with our family's name on it.

It is a great pleasure to be here, David. Thank you for having me. You should know that I found out that I was a J100 nominee this year through my mother, through her Facebook Jewish Moms of Montreal group. Someone posted it, and she called to tell me, which is always really nice when she finds out about things before I do, especially for a nomination that makes her as proud as this. So thank you.

I will tell you something that I haven't really shared with anyone, but I deeply believe to be true. When you look at the fact that Jews are about 15 million on the planet, but we are disproportionately successful across almost every vertical of life, of business, of professionals, maybe other than sports. We own the teams, but we're not really great athletes in that way. I know the Maccabiah Games try to prove that wrong, but in truth, we're good at most things. I actually think one of the reasons that we've done so well is... people talk about the grit and the hard work and the work ethic and the multigenerational trauma and all that stuff. I actually think it's much more simple than that. I think one of the reasons that we have been so successful is because we have this super ingredient in us and in our lives known as Jewish mothers. And I think Jewish mothers have given their children chutzpah, audacity, confidence, swagger, and just incredible abilities, because so many of us have these amazing Jewish mothers in our lives who have told us from a very young age that we can do whatever we want. And at some point, I hope someone writes a book about the unfair advantage that Jews have by having Jewish mothers, because I think it is underestimated and undertold.

I mean, it's my favorite speech in the world, the Teddy Roosevelt speech, 'The Man in the Arena.' It is not the critic who counts, but the man in the arena, or the person in the arena, that counts. I think for any leader, whether you're leading in the context of an entrepreneurial venture like a company, or you're leading in the context of an organization, or across any vector, there is no shortage of people to tell you all the things you're doing wrong. And I think having a growth mindset and feeling like you can always do better and learn more is incredibly important. But I do also believe that there are many people out there that are getting whiplash from people's opinions. And I think you started the conversation today in the introduction by saying that I'm a superbench and a proud Jew. Every Friday for the last four years or so, my wife, Lindsay, and I, and our daughters, Bailey and Zoe, put out a message to the world across social media saying, 'We hope you had a great week. We hope you have a great weekend. Shabbat shalom.' When I first started doing that four years ago, I got countless messages from friends, family, and anyone who seemingly cared about my family or purported to care saying, 'Terrible idea. You are putting a Jewish star on your arm and you are identifying yourselves as a Jew. Do not do this. Please stop doing this.' And four years later, I have all those people that told me not to do it tell me how great it is that I do it. My point is that I think you have to take advice. You have to value others' opinions. You have to be ready to change course if someone has an idea for you that can help you and add value. But I think you have to be very careful where that comes from, because ultimately what people are doing is they're exporting their own values to you, but they're also exporting their own BS, their own baggage to you as well. And especially in the entrepreneurial realm, people are very quick to provide opinions and advice. And I think you have to actually ask yourself, is this someone who I should be taking advice from? Is this someone who has the requisite experience where their advice is actually objective and valuable? Many years ago, we talked earlier on about how you're an ex-lawyer and so am I. I never planned to practice law. I'm not sure you did. But I thought law school was incredible. I'm glad I went there. But as part of it, after you finish law school in Canada, you do 10 months of what's called articling to get called to the bar, and you work for a big law firm and you train under them before you get called. And I knew I was never going to practice long term, but in that articling program, I was working for a mid-size firm in Toronto. And I remember someone asking me, 'Hey, how do you know you don't want to practice?' And I said, 'Well, that was never the point. I always want to be an entrepreneur.' And I said, 'But also, when I look up at the top of the firm and I look at who is leading the firm, I ask myself, is that someone I want to be, or someone's life that I want to have in 10, 20, 30 years? And the answer is unequivocally no. They are on the wrong side of the table. They are not building. They're consulting, they're guiding, they're playing the role of...'

That's right. They're not in the arena, and I need to be in the arena. So that's what it meant. And that tweet that you referenced, or that exposé, went viral yesterday, and I think because a lot of people it resonated with. They also believe that they often get caught up in people's advice who should not be giving them advice.

I was at McGill for my undergrad. I finished high school early. I finished high school in Boca Raton at 17 years old. Went to McGill for undergrad because it was cheap. My parents did not have a lot of money, and so because I was born in Canada, McGill offered me in-state tuition, and it was very inexpensive and a great value. So I went there, and I had to start supporting my family. Built a t-shirt business when I was in college, and the t-shirt business did really well for a 20-year-old kid. In the grand scheme of things, probably didn't do as well as relative to now, but at the time, I helped my mom with rent. I helped put my sisters through Jewish private school.

My dad was not around, and a mentor of mine pulled me aside at some point and said, 'This t-shirt business you have is basically a cute business, but it's not going to go anywhere. And actually, you have far more potential than you know doing this. You should go to law school not to become a lawyer. You should go to law school because law school will be like finishing school for an entrepreneur. You will learn how to write, how to think, how to articulate, how to negotiate. You will learn life skills. You will learn how to read 4,000 pages and pick out the one line, the ratio decidendi, in Latin, the one line that matters.' And for me, law school was finishing school for entrepreneurship. I did a joint JD/MBA, so I also went to business school. And I think if I had to do it all over again, I would do the law degree again. I probably would not go to business school unless it was at Harvard or Wharton where the network itself is actually more valuable than the curriculum.

I heard many, many years ago that... I think it was Gates, I think it was Bill Gates who said it, but it was in a conversation with Gates that went something like, 'Whatever you did between the age of 13 and 16 for fun and for free, if you can make a career out of it, you're probably going to find your life's work.' Between the age of 13 and 16, I was in high school, a public high school called Spanish River High School in South Florida. I was starting companies. I had a DJ business. I was always flipping things. I was selling t-shirts and all types of little hustles. I was an entrepreneur.

Sports cards were part of it. The real money in high school was made on DJing bar mitzvahs for wealthy people in Boca Raton. So that's what I was doing. And so I heard that very early on in my life, and I thought a lot about that. I think the path to finding your life's work is to find something that... there's a concept for this called Ikigai. It's a Japanese concept, which is the Venn diagram overlap of what do you love, what is someone going to pay you for, and what's the world going to value. And when you can find that thing in the middle, that is likely going to be your life's work. Not only will that be a lot of fun and an incredible journey of learning and growth, but also you could potentially satisfy all your ambitions. And certainly for me, given my family's background, making money was very, very important to me. Having financial security and creating multigenerational wealth for my children and grandchildren was important. I didn't have that. I wanted that. That's the best advice I think I ever got, although it wasn't direct. The worst advice I ever got actually was less obvious, but it's a little bit like, 'You become the five people you surround yourself with.' And the reason I think that's really bad advice is because I think... my friend John Hope Bryant, a famous entrepreneur out of Atlanta, says that if you hang around with nine broke people, you'll be the 10th, and if you hang around nine successful people, you'll be the 10th successful person. I believe that. I do believe that your community, the people you spend your time with, do help you achieve certain things. But I do think that the corollary to that, the double-edged sword, is that you end up spending your time with the same people over and over again. And the story of my career and the story of Shopify is the story of me and Toby, who was the original founder of Shopify. And we would never have been friends in high school. He was... I was class president, I was on the varsity wrestling team, I was an entrepreneur, and he was coding, and he didn't go to college. So actually, I think that advice, 'Surround yourself with people... you become the five people you surround yourself with,' is good advice generally, except it misses the second line, which is: 'And also get outside your comfort zone to bring in people into that circle of five that you historically would never have spent your time with.' I think they help you grow into new areas, and I think they help you grow as a human.

Yeah, I know exactly what you're talking about in the sense that we need both. We need to surround ourselves with powerful people that share our vision, share our values, that are quality people. At the same time, if we're only limited to that scope, we're going to be depriving ourselves of tremendous potential for partnership and growth and stretching.

You know, Jesse Itzler, because he knows it very well. Jesse is like an early mentor of mine, and I know that's a big line of his also.

Well, that's specifically about the fact that when I look at the people that I admire most, whether they're the people that I interview for Big Shot or they're just mentors in my life, for the most part, they're entrepreneurs because I'm at my core, first and foremost, an entrepreneur. And the entrepreneurs that I admire, they didn't just change their lives, they've changed generational lives. They've changed their children's lives, their grandchildren's lives, and if they're really lucky and really smart and thoughtful about it, their great-grandchildren's lives. And I think as an entrepreneur, that is something wonderful to want to achieve. Not necessarily to achieve, but to want to achieve. I think that forces you as an entrepreneur and a founder to think very long term, to think not in quarters or even years, but truly in decades. And so that's part of it. The other part of it is that two generations ago, or one generation ago, my father was a poor Hungarian immigrant who escaped persecution. His grandparents were Holocaust survivors. They then immigrate to Debrecen in Hungary. Then the Hungarian revolution happens in the early to mid-50s. It gets really bad again for Jews. And then in the middle of the night, they escape Hungary and find their way to a boat and spend weeks traveling on this terrible vessel to Canada, which let in 40,000 Hungarian refugees. My father was that person. He gets here. My grandfather tries, doesn't have any money, doesn't speak the language, has no education, and my grandfather opens a little egg stall called La Capien at the Jean Talon Farmers Market here in Montreal.

And he worked seven days a week his entire life. The fact that a generation later, his grandson, my father's son, was able to build a company worth well over a hundred billion dollars makes me really proud. And my grandfather is not around anymore to see this. My paternal grandfather, but my maternal grandfather, who was born here, who was a peddler his whole life, is around in my life. I'm very, very close to him, and he sees my success. I see it in his eyes, just the way that he thinks about our family's journey, that he started with nothing. He sold schmattas in the back of his car. I posted some videos about this because I actually interviewed him for Big Shot as a sort of private episode which I've not released. But I wanted to record his story, my grandmother's story, before they passed. They're in their early 90s. And it changes the dynamics of what it means to be successful. It means it's not just about you. It's about long-term legacy. It's about positioning the family in a way that my grandparents could never even imagine. I'll tell you a quick anecdote. When we left Ottawa, my wife and I recently moved from Ottawa, Canada, where we started Shopify, to Montreal, which is our favorite city in the whole world. We moved here about two years ago. And our parting gift to Ottawa was we built the Finkelstein Jewish Center. We met a Chabad rabbi when we were in law school, Rabbi Charski, an amazing man. In fact, Lindsay and I met each other through a Jewish student event there. And he never had a building. So he was hosting this out of his house, like a lot of great Chabad rabbis do on campus. And I made a sort of throwaway comment in 2007. I said to him, almost 20 years ago, 'If I ever have any money, I'd love to build you a proper synagogue, a proper Jewish center.' And in 2018 or so, I called him and said, 'I have some money. I want to start building this.' And it's taken five or six years for us to find the property. We built it. It was too small. We built it again, made it even bigger. And we had the opening in October 2025. We had the ribbon-cutting ceremony at the Finkelstein Jewish Center. My parents were there, my family was there, the prime minister of Canada was there, all the major people, the mayor of the city was there. It was a very special moment. I got on stage, and I had been thinking about this speech for years: what am I going to say when it's finally time to open this? And I asked everyone to look at the building, and I said, 'This building is not a symbol of success. It's not a symbol of hard work. It's not a symbol of entrepreneurial strategy. This building is a symbol of survival.'

Perseverance. This building is the Jewish story: two generations ago, my grandfather was sitting in a concentration camp, and now I'm putting up buildings with our family's name on it.

I'm not chilling. There's no... we're not sitting on the couch. My wife is a psychotherapist. She's also an entrepreneur. She's about to start her second company. She had an ice cream company. Now she's starting a high-end gift basket company. What they see, what they are experiencing growing up in our household, is incredibly hardworking, passionate people who are always talking about the next thing and building and community and hard work and grit. And they are growing up in a beautiful home, much bigger than I grew up in. And we have staff and we have people helping us at our home. So I'm not going to say we shouldn't have these things, but there's deep respect. There's deep gratitude. I explain to my kids all the time how we got here, why we have the things we do. And I think ultimately my version of it is probably not on either extreme. It's somewhere in the middle, where I want my kids to find their own version of life's work and be independent. But I think the idea of creating multigenerational safety nets matters a lot to me. And you've heard this too, but they often discuss why Jews, modern Jews, have so much anxiety. And often you hear about well, it's because we're the ones that survived, and the paranoid survived the concentration camps. So what you're left with are not the Jews that were killed, it's the ones that were incredibly anxious and paranoid, and that doesn't go away. It's in our DNA.

So the podcast... so my one of my best friends is David Segal. David is famously the founder of David's Tea. I did not know David growing up. David and I both met in 2015, the year that I was taking Shopify public on the New York Stock Exchange and he was taking David's Tea public on the NASDAQ.

And someone connected us and said, 'You guys don't know each other. You guys are both Jewish entrepreneurs. Whose IPO was more successful?'

He would admit that too. He's done very, very well. He left the company shortly thereafter. But I think we both actually... at the IPO time, I think our IPO we had a billion dollar market cap. I think he had an $800 million market cap. So it's pretty close. Unfortunately, David's left and that company has gone the other way. Well, Shopify has grown 100x since then. But we met, and the centerpiece of our friendship and relationship has always been this incredible curiosity about Jewish entrepreneurship, and specifically the greats, the people that came before us. We've been talking about the Rothschilds since we met and their story. We've read every book possible. We talk about the Bronfman family all the time. We talk about these iconic people, and that's just how we talk. We hear these stories, read a book, and we're always sort of kibitzing about these people.

No, we've not done the Reichmann family, but we talk about the Reichmanns all the time. In fact, the Reichmann family, one of our favorite stories is the Shabbat elevator, where not only they put a... because they had built First Canadian Place, the tallest building in Canada. But they had a Shabbat elevator, but everyone else in the building who was not Jewish had to ride the Shabbat elevator up and down all Saturday, every Saturday for Shabbat.

It's an incredible thing, and they're an amazing family. So that's sort of our... I don't know, that's what we talk about when we hang out. We're not sports guys. We talk about Jewish entrepreneurs. So about a year... so around 2022 or so, we vacation together. We're sitting on the beach in Turks and Caicos, and we're talking about all this stuff too. And it dawned on us that some of these people, some of these Jewish entrepreneurial legends, are in their 80s and 90s and hundreds. And unlike Jesse Itzler or Harley Finkelstein, they're not on the podcast circuit. Their stories have not been captured because the podcast didn't exist until very recently. And maybe they wrote a book, but even their books haven't been updated. So we thought, 'Hey, wouldn't it be cool, just for ourselves, for no one else, if we began to archive the stories of the greatest Jewish entrepreneurs of the last half century?' And we're like, 'Yeah, let's do it.' So we ended up... I called a couple people that I thought would be great. Again, this is the Big Shot podcast started just for David and I, just as a personal interest project. And so I called Charles Bronfman first, because Sam Bronfman is probably, on a North American scale, the godfather of Jewish entrepreneurship. He built Seagram's, but more importantly, he created what is now the community of successful Jewish entrepreneurs. So we called him first. And then second, I'd met many years ago Aldo Bensadoun, who was a very poor Moroccan immigrant who came to Canada and built Aldo Shoes, became a billionaire, amazing story. And then Jonathan Weiner, who created Kanderell. So three Montreal-based Canadian entrepreneurs who I knew really well, and I called them and said, 'Can I record your story?' And Dave and I go to see them at their... I think we did one at Shopify and the rest we did in their homes. And we literally just got whatever camera crew we knew and we said, 'Hey, let's just start filming.' Called it Big Shot, and recorded these three episodes, and we put them on YouTube, just put them on YouTube, and kind of left it there. And it was remarkable. Immediately, we started to get so many people calling us and asking us about these stories and explaining to us how much the stories affected them and how everyone sort of had a different version of having met someone. And it was just the most incredible thing. So from there, we decided, 'Okay, there is a real opportunity for us to continue telling these stories.' Then we went to Toronto and we interviewed Isadore Sharp, who created the Four Seasons, and we interviewed Eddie Sunshine, who created the REIT. And it just started getting bigger and bigger. So we've now done about 30 episodes or so. The archive is stacked. We did Joe Schaefer, 104 years old. We just did Jeffrey Katzenberg, Lloyd Blankfein. We've done Michael Oitz, Steven Ross. We did Don Soffer, who created Aventura, who literally built Aventura, and he unfortunately passed like two or three weeks later, so this was sort of his final interview. Bobby Kotick, Mike Milken, Linda Resnick created Fiji Water and POM Pomegranate Juice, Mickey Drexler, Retail Royalty, Bobbi Brown, Ron Shaich, Leon Cooperman, Larry Silverstein. I mean, you'll know from New York, literally built New York City, these incredible people. And it's just been this incredible labor of love for us. And now Big Shot is in the top 5% of all podcasts. I think it's the only Jewish-related podcast, maybe other than Call Me Back, but I think it's the only Jewish-related podcast in the top 5% of podcasts. Yeah. And so we had Katzenberg last week. Next week we have Barry Diller coming out.

It started as live interviews, and now it's more... now it's virtual. Everything's live.

That's why you don't have a gazillion podcasts. I mean...

I just didn't realize that at all.

Wow, that's incredible. Fiji water, palm pomegranate juice. 75% of every pistachio created like sold in the world, she owns. She, you know, years ago, she owned Franklin Mint, created that really beautiful high-end mahogany monopoly board. I mean, these are, and again, across the board, other than maybe one or two, these were all poor people and they built industries. I mean, Izzy Sharp started with a motel in Toronto and built the Four Seasons hotel chain. And the stories they tell are incredible. And because they're above the age of, you know, 80 years old or Joe Schaefer, 100 years old, they don't hold back. They tell everything. There's no more ego. They're just candid and transparent. And it's a celebration of Jewish survival. It's a demonstration of Jewish success. But also, it's a bit of a Trojan horse. And I don't often share this, but I'll share this. It's a Trojan horse because a lot of non-Jews also listen and watch these shows. And what Big Shot does is, and we've heard this now hundreds of times from non-Jews who don't know these stories, who are not part of the Jewish community, they say, 'We always assumed that all these people were born into it.' That all these people were born on third base or second base. We had no idea that you know Eddie Sunshine who created RioCan, who created the modern day REIT, he was born in a Bergen-Belsen, he was born in a displaced person's camp. For him to go and become one of the wealthiest people in North America, like how does that happen? Well, we explain how it happens. And there's some really cool lessons about family and hard work. And you know, everyone talks about their spouse. And we ask this really interesting question, David. We always say at the end, 'Okay, when did you know that you made it?' And all of them, to a T, other than one which I won't say who, you can go check if you want, all of them have said, 'We have not made it yet.'

And it's just this amazing thing to hear. Some of these people are worth tens of billions of dollars and they still don't think they have enough and haven't made enough and haven't done enough.

That's right. It's the journey less. But actually, that also makes me feel, this is where it's a very personal thing, that makes me feel seen, 'cause I still don't feel like I have enough. Am I doing enough? I've built enough. I'm still grinding every day. But it's a beautiful project because it's the story of survival, just like me putting up that building. Sounds like you're fighting anti-semitism and you're making what we would call in Hebrew parlance like a great Kiddush Hashem, a great sanctification of God's name, because inadvertently you're in essence fighting anti-semitism because you're educating non-Jews or maybe even Jews who have a negative perspective of Jewish wealth, that it came primarily through incredible hard work and diligence and sacrifice, which is incredibly valuable. That's the best part. I get these messages all the time saying, 'I watched the interview with Leo Cooperman' or 'I watched the interview with Michael Milken,' both billionaires, both incredible finance geniuses. And Milken famously is the Bond King. And I'll get these notes from someone and they'll say, 'You know, I'm not Jewish, I'm not an entrepreneur, but I watched the Milken episode. I had no idea how hard it was to get to where he is.' And it creates understanding for us. No longer does this narrative that we're 15 million people in the world out of 8 billion and yet we're disproportionately successful, like we must own the banks or we're bad for doing this, or we've had an... It creates understanding around the world that this is not like we did not have a head start. In fact, just the opposite, that constantly throughout history people have wanted to hurt us and push us down and we've survived and persevered. So, actually, it's interesting because more and more as I get older, I actually think Big Shot will be the thing that will ultimately be my potential legacy. Not Shopify, not my business success, but this Sunday project that I have, and it's all funded by me and David.

Yeah, usually we, I mean, Dave and I both run companies, so we do it on weekends and we fly out to meet them and usually done on the weekends. Sundays is usually the day. And we had this great film crew and then it's funded just by us personally. We don't want to take advertisers. So anyone who's listening who loves the show, please reach out to me because it's supported by people that like it. And frankly, David and I each write checks every year to keep it going personally because it's become so important to us.

Well, part of it is selfishly, my co-host and my co-creator of the show is one of my best friends, so it's really fun to do this together. But David and I are totally different. David will come in with the book of the guest, tabbed, highlighted, knows every single detail. And I'm more big picture. I'm like, no, thematically, I want to understand their relationship with their children. Like in the case of Don Soffer, built Aventura, obviously his children had inherited the businesses. I want to understand that dynamic a little bit better. Or Linda Resnik, her husband is her co-founder, Stuart Resnik, who in his own right is an incredible entrepreneur. I want to understand how that works. Or Mickey Drexler, he wasn't a founder, but he created Old Navy inside of the Gap. I want to understand the dynamics of how do you create, you know, he created Old Navy inside of the Gap working for that family. How does that work? So I think the key to it is to have someone that you know, it's like a marriage in many ways, finding someone that you have...

And every now and then I'm like, 'David, put your notes away, let's just focus on the big picture.' And every now and then he's like, 'Hey, you need to know these facts here.' So it's a wonderful dynamic because we both bring different skills to the table. And it's just more fun to do with a friend.

Yeah, it's always one person. Although I've often said that I have a couple, I have one new idea that I'm sort of working on right now. In fact, if anyone's listening wants to run with it and has time, you should do it. But I have this concept that I love called 'My Best Friend.' Literally, that's a podcast called My Best Friend. And it's you don't interview the person, you interview the person's best friend and you basically figure out what the real story is, because often the subject themselves, we do this, I do this and you probably do this too.

But it's our best friend who's like, 'Well, let me tell you what really happened there.' And so I think that could be, unfortunately I'm out of time and I have to pick the things I want to work on, but I think that could be such an interesting show because it is like the real story as opposed to the story that the...

I mean, and only the spouse, or you can do the subject and the spouse and basically the spouse is just like, 'Well, that's wrong. Let me tell you the real story.' But it's really fun. And the fact that this is a very modern 2026 thing, but the fact that I don't have to ask for permission from a network or from a streaming platform or from anyone to put this show out. I think about 10 or 20 years ago, or 50 years ago, if I wanted to create Big Shot, there were gatekeepers on distribution. I would like Shopify. I mean, we haven't talked about...

That's what I'm able to do through things like YouTube or Spotify or Apple Podcasts. I don't have to ask permission from anyone to publish these things. And if people like it, great. But if they don't like it, I'm okay with that also. I'm not looking for views. I'm not trying to raise money with ad dollars. I'm just trying to put out something that I deeply care about myself. It's very, you know, Rick Rubin's frankly too young for our show yet because...

75? Yeah.

Yeah. We'll make exceptions, like if you're Bobby Kotick who sold his company...

Generally above 75. That's where they tell us the real story of how this all happened. Yeah.

So my connection to Israel is far more symbolic than it is actual. Meaning, I've been to Israel a number of times in my life. I got a chance to go first time on Birthright and I've got a chance to go back a number of times. And to me, my personal connection to it is this is a place that was created in a reaction to what my family went through in the Holocaust. This was a safe haven, fundamentally at its core, that's what it is. I know it's a place of worship and I understand the culture of it and all that comes along with it, but ultimately it is a safe haven. It is unfortunate that we need a safe haven, that we need a place where every Jew around the world can immigrate to just simply by virtue of them being Jewish that can feel safe. Actually, funny enough, I find right now probably the safest place for Jews might not even be Israel, actually might be Miami. I think Miami has...

No joke. I mean, it is remarkable. We spend time there quite a lot. I grew up in South Florida, so we go there a lot. And I think that is the place I, as a Jew, feel the safest. Mostly because the volume of Jews there is remarkable. And frankly, I think the state, the community, the city, just everything makes you feel okay about being Jewish.

And they, I mean, I'm not religious, but some of the things they do, like I was in Surfside a couple Fridays ago walking around with my wife and the fact that they have figured out how to open restaurants on Shabbat.

I mean, they're innovating on Shabbat. They have figured out a way for observing Jews to have dinner on a Friday night at a really great restaurant and observe all the rules and all the laws of Shabbat. But Israel to me is a symbol. It's a symbol of our right to exist in the world. We shouldn't need that. But right now, I think we've all become more Zionistic, and it has less to do about the place itself and more to do with what it stands for for us. It is our safe haven. And I was born in the early 80s. I'm an older millennial. I'm 42. I was born in 83.

Well, but I'm an older millennial. Sorry. In terms of millennials, I think I'm one of the oldest millennials by age. So...

True. I went through my entire life hearing about anti-semitism, hearing why Israel was important, celebrating Yom Ha'atzmaut, going on Birthright. I went to Jewish summer camp and I went to Jewish elementary school and we planted trees every year. And Israel was this thing I was related to but never really understood. And that all changed after October 7th. It's now sort of common to say this, but I do believe in this idea of October 8th Jews. I don't think people that were not Jews became Jews. October 7th became an October 8th. I do believe October 8th simply just turned up the volume for all of us because it was a reminder of how all those stories you heard from your grandparents, all those warnings you heard from your crazy great aunt about be careful wearing a kippah when you're walking down this street, and you're like, 'What are you talking about? I live in Boca Raton, I live in Montreal, I'm in Toronto now, I'm in New York City. What are you talking about? That is your own baggage.' I now understand that baggage. I now understand the importance of protecting this thing, the Jewish homeland. And I think that it is as fragile as it's ever been and therefore it requires full unequivocal support. Now that being said, I think you should be allowed to criticize politics in Israel. I don't think you have to agree on everything the government is doing. I think you should be able to say this shouldn't be done this way without feeling like you have to be an absolutist. But I think for the first time in my entire life, the last couple years, I've begun to understand why the protection of the Jewish state of Israel is paramount.

Yeah.

And it is unbelievable that that happened in my life. I thought we were sort of past that. We have not. I will tell you something that has affected me more than anything else. There's been a couple times, I actually wrote an op-ed about this, January 1st, in the National Post, which got a lot of attention and went viral. And it was about my experiences as a Canadian Jew, my lived experiences. And I told two stories. The first one I've already mentioned, which is that sitting on stage opening the Finkelstein Jewish... which had nothing to do with Israel. Zero to do with Israel. It was about my family. It was about this rabbi who was kind to me when he didn't have to be. It was about the Jewish community in Ottawa saying thank you. It was about the fact that a G7 capital did not have a synagogue downtown or a Jewish presence downtown. That is the capital of the country of Canada, a G7 country. There were all these things it was about. What it was not about was Israel. It had nothing to do with Israel. And yet I had protests interrupting this speech that I had thought about for 20 years, giving in front of my children and in front of my grandparents. And the other time it happened was we never do Big Shot live, but it's done with no audience. It's me and David and the guests and our film crew.

So we did one event. It was in Montreal. It was for a woman, incredible woman named Heather Reisman, who is the founder of Indigo Books, which is like the Chapters or Borders of Canada. Her husband is Gerry Schwartz, Onex, probably one of the greatest entrepreneurs on the planet, Jewish entrepreneurs on the planet. They are a power couple. She is incredible. She's a self-made billionaire. She's awesome. And Dave and I were interviewing her on stage, Big Shot, celebration of Jewish entrepreneurship in Montreal. We did it at a conference called Startup Festival, which is this massive entrepreneurship startup festival here in Montreal in the Old Port in a beautiful location. And we had people rushing the stage, yelling horrible things at Heather, at me and David. And those two incidents again had nothing to do with Israel. And yet the things that were being yelled at us, these beautiful moments were just disturbed simply because we were Jewish. Now it was under the guise of some sort of advocacy, right? If you ask these protesters, they all gave interviews afterwards why they did that. It was all about advocacy. They were advocating for people that couldn't help themselves. They were advocating against the Israeli government. They all had their reasons for it, but it was bullshit. It was hatred and anti-semitism disguised as some version of advocacy.

And those two things happened to me personally in the last 12 months. I could not have expected that five years ago. That was not on my bingo card of things that were going to happen in my life. And it's activated me in a way that I don't think I've been activated before. It's created, I mean if you thought I was ambitious before about building Big Shot, like I don't know if I can swear on this show, but like let's fucking go, because now I want Big Shot to be as big as possible and I want as many people to listen to it and I want to celebrate as many Jewish entrepreneurs as I can. My vehicle for fixing this, I don't have a lot of, I'm not a politician. I don't write legislation. I'm not an author. I don't write books. I am an entrepreneur. But I have this new tool that I've been architecting and developing called Big Shot. And now I'm going to use my tool that I've built to be as loud and as proud about being Jewish as ever. So if you are one of those protesters that disturbed either of those events, that threw horrible words at me and my family, and somehow you've heard this, all I can say is all you've done is activate me even further, because now I really want to make this big.

Yeah. No, I mean, rabbis are, I think...

I actually think they are the most wonderful. I am so pro, I'm so Chabad-pilled. I think these people are so entrepreneurial, so caring. I'm sure there are others that maybe, I haven't met any ones that...

That's an amazing thing because Tucker Carlson blamed Chabad for a whole bunch of horrible things and I just went on X and went on Instagram and said Lindsay and I are going to donate to every single Chabad house on campus because of this.

Same thing. But there are 19 Chabads on campuses from British Columbia to Prince Edward Island, all across Canada.

That's right. And so I said, Lindsay and I donate to everyone. I have had dozens of people jump on this and say, 'We're in.' Also, entrepreneurs from all over the world said, 'We're going to match whatever you're doing.' So this horrible thing that Tucker said about Chabad turned into the greatest fundraising campaign in Chabad history. And it was this amazing thing that is so symbolic, that epitomizes what we are as Jews. Throw at us your worst and we will turn it around and make it positive. But back to the Chabad thing. Actually, I never really ran away from Chabad. Sometimes I find they could be overly aggressive, but I love their hustle. I love their ambition.

And it's entrepreneurial. And not just that, what Chabad Rabbi in Ottawa who married me, an amazing man, will tell you is he used to come in the middle of law school and he'd want to wrap tefillin. And I say, 'Sure.' And he'd say, 'Let's go in a room.' I said, 'No, we're going to wrap tefillin in the middle of the entire law school.' Okay. And then, I don't know if you know this guy Yossi who goes around the world?

So Yossi I guess heard the story or knew about the story. And so in my world in retail, he made a career out of it. In my world, the biggest conference of the year is NRF, National Retail Federation. It's at the Javits Center. It's every January. There are 40,000 people that are there. It is the retail conference on the planet.

And a couple years ago, Yossi showed up and he messaged me. He says, 'Hey, I know you're here. I'd love to wrap tefillin with you.' I was like, 'Great.' So he comes in and literally in the middle of the Javits Center in front of 40,000 people, we wrapped tefillin. Guess what happened? Another Jew came over and then another Jew came over and then all these people came over. And Yossi has now come back, I think every year to NRF to wrap tefillin with me. In fact, this year we did it in the middle of the Shopify booth and all these Shopify merchants and partners who were Jewish were wrapping tefillin and those who weren't Jewish were there asking questions. This is who we are, David. We are activists. Entrepreneurship doesn't really describe it, but we have something in us whereby we are survivors and that is multigenerational. And that hopefully is something that I want for my children. Forget their inheritance and forget the things they're going to have or not have. What I want my children to inherit is that grit. I want them to inherit that instinct of survival. And I know what comes along with it is also some anxiety and I can't sit still. My mother would say I'm sitting on schpilkes, whatever the hell that means. But I want my children to inherit that sense of community and purpose because that is how we've survived and that is how we will continue to survive.

Sure.

Look, I think we are living in the era of founder leaders. Brian from Airbnb had this great line...

Brian Chesky, yeah. Had this great line maybe a year or two ago where he said, 'It's time for founder mode.' And I love this idea that obviously Steve Jobs wasn't able to see, he passed away, and I think he found the closest thing he could find to a quasi-founder in Tim Cook. Tim kind of operated like that. You see Satya Nadella also at Microsoft. He obviously wasn't the founder of Microsoft but he operates like a quasi-founder. I think we are living in an era right now unlike...

Yeah, that's right. Yeah. I was the first customer. And then I joined Tobi very early on and been with Tobi now for 20 years building the company. But companies like Shopify, historically 10 years, 20 years, 50 years, 100 years ago, at some point we would have got tapped on the shoulder by the board or some investor and said, 'Hey kids, it's time to let the adults in the room and let them take over.' That is not the case anymore. Now founders are leading their companies from inception all the way to full scale. And I don't think there's anyone on the planet that cares more about the business than the founder. So, I think Steve Jobs, those are massive shoes to fill. I think Tim Cook did an amazing job. We have a great partnership with Apple. They're an amazing company. I think their new CEO, who is also homegrown as well, is probably the right pick as opposed to an outsider. But I think we are living right now in this era of founder mode. And I think it is leading to companies that, you can tell when it's a founder leading the company. Even if you don't know them, you can see from the product. Steve Jobs famously cared about the chips inside the computer and how they were designed. If you broke open the hardware and looked inside of the computer, which no one saw, you would see all the wiring was perfectly, beautifully designed and architected. Steve would talk about the back of the bookcase that no one saw, but he cared deeply about it. I think you're seeing a lot more attention to detail and a much higher give-a-shit quotient from these founder-led companies. Big shoes to fill, but I think Tim did an incredible job.

I think this generation now has probably the greatest opportunity to build something in history. I think both the barrier to entry and the time to scale have completely collapsed. There are companies on Shopify, there's a company called Gruns for example, that was built two years ago on Shopify, it's a supplement company, they just got sold to Unilever for a billion dollars. Gymshark, Olipop, On Running, these businesses didn't exist 10 years ago and now they're the dominant in their verticals. We have never seen so... It's never been more affordable to start and I think time to scale has collapsed because of it as well. But I think ultimately what AI is delivering for entrepreneurs is this uncapped reach and uncapped resources. There was a proverbial, metaphorical sound barrier to entrepreneurship, which is you could only grow so big and eventually you had to raise a ton of money or go hire a massive team. There are teams now that are three people strong that are doing a billion dollars in annual revenue. I think also from the job market perspective, AI certainly does shake up the job market. But I think the reputation of entrepreneurship as a gamble will be reframed. I think a lot more people will say, 'I want to try my hand at this. The thing that I loved between 13 years old and 16 years old, I want to try my hand at doing this.' And back to my grandfather where we started the conversation, if his egg stall would have failed, he would have had to sell his house or not put food on the table. The barrier to entry and the cost of failure were so high. That's all been taken down. So I think the skill set of all the best entrepreneurs I know is what AI cannot replace. Things like taste and judgment and discernment and ambition, that's a human thing. But I think now is really the time to take advantage of that. So this next era of entrepreneurship may very well be the golden age of entrepreneurship and I think it's going to be human ambition married with the greatest superpower technologies ever. And I think anyone who's listening needs to be a techno-optimist right now. What that means is you're going to use one of these agentic applications. You're going to use one of these large language models and you're going to see something that doesn't look right or you're going to see some sort of hallucination. You're going to be like, 'Ah, this is terrible. I can't believe it.' And then a week later that mistake will be fixed or a day later that mistake will be fixed. Or you're going to give it a project to do for you and it's going to come out, it's not going to be great. If you try it again 24 hours later, it may be exceptional. That is the pace of change right now. You have to be a techno-optimist and you have to believe in the fact that this is going to be, Steve Jobs back to him for a second, talked about the computer being a bicycle for the mind.

And I think if the computer is a bicycle for the mind, AI is like an F1 car for the mind. This is unbelievable what we can do here. So I'm incredibly optimistic about...

You'd be surprised, but I mean a lot of people, and that's why I'm saying, I know a lot of the technology doomers out there or people that are worried. I think anytime there's big change, there's always going to be concern, but I think you have to be a techno-optimist. I think all of you listening need to play with these tools and tinker and toil and build something cool and go try something. A friend of mine was looking at a house on my street and he wasn't sure. And I literally just went into my Claude and I said, 'Hey, here's the house from Google Maps. My friend's really into more modernist design, some Scandinavian design, a little bit of Japanese design. Give me five mock-ups of what the house could look like.' And I sent him a deck with the five mock-ups. And he's like, 'Blown away.' He's like, 'I can't believe this. This is exactly what I want.' Anyways, hopefully it leads to him building the house, but that would have taken 3 weeks and $30,000 from an architect just to get some inspiration. And the same way that Big Shot couldn't have existed 10 years ago because the technology wasn't there. And now anyone listening, if there's a story you want to tell, if there's a project you want to embark on, there are no more gatekeepers. We all can do this. So, it's an exciting time right now.

I've had anxiety my entire life. I still have anxiety. I still wake up every single morning anxious. And I've been able to tune that with things like meditation and exercise and frankly a cold plunge has been one of the greatest new things in my life. I take a cold plunge every morning.

I know, well I still have a cold plunge in the gym. And I don't think that goes away. And as I get older, what I realize is it's not going to go away. That's deep in me. And so for those of you that have something, whether it's your own anxiety or it's some form of depression, I think it's easy to look at people that have had any success whatsoever and think that they've had it all figured out. I do not have it figured out. I'm still anxious about a lot of things, including my own business and my own entrepreneurial ventures. I think you embrace these things. I think we often as entrepreneurs tell all the highlight reels and forget about the blooper reels. But the best, and you hear this in the Big Shot podcast also, the people that you talk to and you ask them again, 'When do you know that you made it?' The fact that David Rubenstein still doesn't know he made it yet, or Charles Bronfman is still trying to prove to his dad that he's a great entrepreneur in his own right. It humanizes these people. It makes us all feel a little bit more connected. I think Sheryl Sandberg and Adam Grant in their book Option B, I think they have a phrase I read a long time ago. I think it's 'embrace the suck.' I think that's what they call.

That's why every morning I get into the cold plunge and I say this is going to suck and I still get in it anyway.