Hot Smart Rich with Maggie Sellers Reum - The Formula Rhode & Skims Use To Win (and how you can do it too!) Shopify President

Episode Date: March 25, 2026

Why is Hailey Bieber’s Rhode a $1B empire while other celebrity brands feel like "cash grabs"?  Shopify President, Harley Finkelstein, breaks down the elite playbook behind Rhode, Skims, Kylie Cosmetics, Gymshark, and Chamberlain Coffee. From the “9 Person Rule” (why your friends are keeping you broke) to the “3,872 Books” email hack that caught Gary Vee’s attention, Harley explains how the world's most successful founders actually think! No more waiting for a sign, a mentor, or 'perfect' timing. The cost of entry is $39 and a 'stupid' idea that you’re finally brave enough to start. The golden age of entrepreneurship is here - don't let it happen without you! Timestamps: 00:00:00 Intro00:02:18 Why You Don’t See Yourself As An Entrepreneur00:05:17 Should Everyone Try Entrepreneurship?00:07:53 Why Most People Never Start00:09:07 The One Thing That Creates Billion Dollar Businesses00:12:50 Motivation Doesn’t Last… This Does00:13:56 Finding Your Ikigai (Life’s Work)00:16:32 “You’re Changing Women’s Lives”00:18:18 Chasing People You Admire00:22:31 Fiverr Ad00:23:42 How To Get Anyone’s Attention00:27:42 Do Creators Have A Peak?00:30:26 Do You Need An Audience To Win?00:33:59 Why Kardashian Brands Actually Work00:39:36 Will Celebrity Brands Keep Winning?00:43:08 Should We Be Scared Of AI?00:47:31 What Is AI Shopping?00:49:48 Will AI Replace Influencers?00:50:59 Will AI Replace Everything?00:53:07 Shopify Ad00:54:04 Bilt Ad00:55:13 A Letter From Harley’s Daughters00:55:51 Raising Future Entrepreneurs00:58:53 What He Spends His Money On01:00:06 Skiing vs Building Businesses01:00:19 Best Books For Entrepreneurs01:01:46 Industries To Avoid01:02:25 The Most Innovative Product He’s Seen01:03:30 What Makes A Brand Truly Great01:06:53 His “Spiky” Career Strategy01:07:45 The One Belief That Changed Everything01:10:22 How To Become A Better Storyteller01:12:32 Where To Find Harley ⸻ Sponsors: Fiverr - If you are scaling a business, then you need to visit https://pro.fiverr.com     Shopify - http://Shopify.com/HSR Bilt - http://joinbilt.com/hsr ⸻ Follow Harley Finkelstein:  Instagram: www.instagram.com/harley Shopify: https://www.shopify.com/ ⸻ Hot Smart Rich: Your Business & Culture Gossip For ambitious women wanting to own the room, gain power, and build wealth. Subscribe to the Hot Smart Rich newsletter: https://hotsmartrich.com/subscribe  Instagram: https://www.instagram.com/hotsmartrich/ Tiktok: https://www.tiktok.com/@hotsmartrich Maggie Sellers Reum: Instagram: https://www.instagram.com/maggiesellersreum/ Tiktok: https://www.tiktok.com/@maggiesellersreum LinkedIn: https://www.linkedin.com/in/sellersmaggie/ Locker: https://www.wantlocker.com/users/maggiesellers ShopMy: https://shopmy.us/maggiesellers Amazon Storefront: https://www.amazon.com/shop/maggiesellers Learn more about your ad choices. Visit megaphone.fm/adchoices

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Haley and the team at Road, Allo, Jim Shark, none of them thought that. they were going to build a billion-dollar company. The only thing you actually need is just... Period. You coming on the show today as the president of Shopify, it's not just a podcast recording. It's a statement. Sorry, I'm getting a little bit of a motion to hear.

I met the founder of Shopify at a coffee shop. Now over $100 billion of market cap. I actually wasn't going to say this, but I'm going to. I was rejected from Shopify 11 times to work there. I did not know that. What can everyone listening to this right now do to get to be the next billion dollar company on Shopify? I think...

Is there something you're already doing or something that you're feeling in a very personal way that you think you have a solution to? That is almost always going to be the best chance you have of starting your first business or your 10th business. You don't need to be Mr. Beast. I think people overestimate how many followers they require and underestimate the idea of... In the world of AI. Is there an industry that you would never start a business in? Oh, there's no debate. Hi, Angels. Did you know that subscribing to our channel is free? And it's the simplest way that you can support our show and help us grow. If you do this, we can bring you even more of the content and the guests that you love. All you have to do is just hit the subscribe button below. So please, if you wouldn't mind, subscribe to the channel and thank you. In case you missed it, you're allowed to be hot, smart, and rich. So let's get into it.

Harley, Thinklestein, are you ready to get Hot Smart Rich? Let's go. What does entrepreneurship mean if we really distill it down? I think for some, it's status. They become an entrepreneur because they want to be an entrepreneur. They want to tell people they're an entrepreneur. For me, entrepreneurship is a way to solve whatever problem you have. And I think most people don't even realize it.

And I get to see it every day at Shopify. Every 26 seconds, a brand new entrepreneur gets their first sale on Shopify. And when I look back across the millions of stores, everyone had a different reason for entering entrepreneurship. But every one of them made their lives better through that journey. When I was seven, I started my first business, Maggie's pet business, taking care of my neighbor's pets. And like there was something about my journey where whether it was like wrapping Christmas

gifts with my sister during college or doing calligraphy or being a promoter in college. It was always entrepreneurial. But it was interesting because I went into the startup world. I went into the corporate world. And I think that title of entrepreneurship became so big in my head as a balloon and something that was like almost unachievable. And it took me honestly until about six months ago to identify as being an entrepreneur. Why is that? So my story as a, like as a human being is a story of entrepreneurship going back generations.

My grandparents were Holocaust survivors. My grandfather gets to Canada in 56 Has no money, can't get a job, doesn't speak the language. The only thing he could do was to start a business. So he starts this little egg stall called La Capitaine. He came to entrepreneurship through the lens of what I call now forced entrepreneurship. He had no choice. There's another segment which is that they don't feel like they belong.

They feel like outsiders like you're describing. You didn't feel like you could articulate or self-identify as an entrepreneur because in your mind you had some other vision of what an entrepreneur was. And it probably looked like, I don't know, a Mark Zuckerberg or a Bezos or someone like that. And there's sort of a third one which is like, I have a hobby. On Saturday mornings, I make the most delicious pancakes and pancake batter for my kids. And on Monday morning, I go to a job that I hate. And all I wish I could do is I wish I can make that pancake batter business into my life's work.

Instead, it's just going to be a hobby. And there's probably 10 other sort of categories of kind of pre-entrepreneurship. But the journey is the exact same. They see something, they need something, and they use the idea of starting as a way to make their life better. And I think one of the things that you're doing, and I think we'll get to AI later on, but I think like two things have changed since my grandfather started that egg business till today. The first is the barrier to entry into entrepreneurship is as low as it's ever been. This isn't a pitch for Shopify, but for 39 bucks a month, you can start a business,

and that business could become a $10 billion a year company. I've seen it on Shopify. And because of the technology and the tools and the ability to scale is unlimited. So you have low-barrett entry, you have unlimited scale opportunity, and, if it doesn't work, you can try something different. In many ways, when you bring all these elements together, what you're left with is this might be the golden age of entrepreneurship. And most people have no idea. With that thesis, do you believe that every single person should at least try to become an entrepreneur?

No, I don't think it's for everyone. Some people have no choice. They have to do it. My grandfather. Some people want to do it. That was me. The only thing in the world that I wanted to do at 13 years old was be a DJ. And I applied to every DJ company that, frankly, I'd ever heard of.

Like literally yellow pages and asking friends and I applied everywhere and no one would hire me. My dad had this really interesting tactic. Every time I came home with a silly business idea from school or from whatever, my dad would immediately go to the home computer and he would make me a business card. And it said Harley Finkelstein, you know, DJ or Harley Finkelstein. or Harley Finkelstein owner of lemonade stand. He made these ideas throughout my life real for me by literally creating the physical manifestation

of my idea in a business card form. So I'm 13 years old and want to be a DJ, nobody will hire me. I end up telling my dad, no one will hire me. And he says, go start your own DJ company, hire yourself. So I do that. And I end up DJing 500 parties before the age of 18 years old. Every bar mitzvah, butt mitzvah wedding,

birthday party, neighborhood barbecue. In my area, my community in Montreal, in Canada, I was involved with. I was DJ. I didn't make a lot of money. I mean, I was literally, you know, like 17 years old or 15 years old or 13 years old when I was doing it. But it was so incredible. It was like this mind-blowing experience that, like, I was able to turn a problem.

I want to be a DJ. Nobody will hire me into a solution, build my own company. And what I realized then is I was entrepreneurial. You were entrepreneurial also doing stuff at seven years old. Some people are like that. Not everyone else is like that. And if you don't have it in you, I don't think you need to do it. But I would also suggest that for those that are listening that are in a job they don't like

or they don't really know what their path might be, that even though entrepreneurship doesn't seem native to them in the way that it was to you and I, Maggie, that it could actually be something for them. And I would suggest to them they should give it a try. If this was 50 years ago, giving it a try would mean taking a loan out from a bank. And if it didn't work, it would mean potentially losing your house or going to some debt. That's not the case anymore. So long answer to short question, no, I do not think everyone should be an entrepreneur.

But I do think more people should try it who probably don't even consider it. Why do those people not try? One of two reasons, I think. The first is I think it's too complicated or too expensive. or they have people in their lives that are not supportive. We have millions of stores on Shopify to level set for a second. We are about 14% of U.S. e-commerce. Okay, so other than Amazon, we are the largest checkout on the Internet in America,

which is massive, right? Crazy. When I look at the top 100 merchants on Shopify by GMV, my sales volume, almost all of them, if I would have asked them when they were 20 years old, if entrepreneurship were building a company like this was in their manifestation journal or was in their vision board I think they'd say no

not a single one of them and I'm talking about aloe and Viori and Faschenova and Jim Shark and figs and on running and I'm talking about like big big brands and I would say almost to a T none of them would say this is what they thought they were going to do what does that do that suggests that there are way more people out there

that should start businesses but are probably not because someone told them they're not good enough or can't do it or it's self-talk that they don't believe they can do it on their own. It's so interesting because I think there are so many people that genuinely feel like that. And it's like what is that pivotal moment or that pivotal thing that everyone listening to this right now can take to get to be the next billion dollar company on Shopify? Pure group really matters. When I was in college of McGill, my dad wasn't around. anymore. I had to support my mom and I have too much younger sisters. So I started selling

T-shirts to universities across Canada. It's not a great business, but allowed me to pay the bills. A mentor of mine convinced me to go to law school. His advice was, you're 20 years old, you have this T-shirt business, you know nothing about real business, no sophistication. Go to law school as finishing school for entrepreneurship. And so I applied to one law school, just that school, University of Ottawa. When I got to Ottawa, I asked where the entrepreneurs hung out, and I was directed to a coffee shop. At that coffee shop, I would end up meeting Toby. I was the founder of Shopify, and I would become one of the first merchants to use Shopify, and that sort of started our 20-year history and partnership and career together.

So the first thing you can do is I think if you were surrounded by other people that are entrepreneur or entrepreneurial, there is this osmosis that happens. If you want to be a podcaster, go hang out with other podcasters. If you want to be, you know, an incredible shape, spend more time at the gym. Proximity does matter. If you're thinking about this, find a group of entrepreneurs, hackathons, like meetups, go hang out in a we work, whatever you want to do, but spend time with people that are on a similar journey, maybe a different steps of the journey, but a similar journey. That's first. The second thing is, okay, hardly I now want to be an entrepreneur.

What am I going to sell? This is way easier than people think. Almost to a T, every one of those top 100 stores on Shopify, the business they created solved their own. own problem. Trina at Figgs had a friend who was a doctor in Los Angeles who was wearing shitty scrubs and she's like, I can do this better. Ben Francis, who created Gymschark, wanted to work out and he felt it was either bodybuilder gear or it was yoga gear.

There was nothing in the middle. And if you go down all of those different brands, same thing with Danny and Allo, same thing. Like all the brands you're talking about, they were solving a problem that they had encountered on their own. So you don't have to go in like go on some sort of, you know, mystical journey, you know, to the other side of the world to go like have a vision quest to go figure what you're going to sell. Is there something you're already doing or something that you're feeling in a very personal way that you think you have a solution to? That is almost always going to be the best chance you have of starting your first business or your 10th business.

And I think most people discount the pancake batter or they say, well, yeah, but I may. beautiful blankets, but I really just make it from my nieces and nephews, like, no one's going to want that. And it's bullshit. And that's bad self-talk. And you're right. Maybe not everyone's going to want it, but you owe it to yourself to at least give it a try because, like, look what you've built.

Like, you started with an iPhone. Like, look at what we're sitting in right now. It's unbelievable. And it's simply because you believe that this thing, I think you enjoyed it yourself, right? But you also felt, hey, this could have some value. And there's a lot of people that started podcasts and didn't have your success. And that could be the case. But it may be that you started this podcast.

It didn't work. But something, you know, you're like, actually, I made these pillows for the podcast. And now, like, you have a million dollar pillow company. That's the best part of building right now in modern times that the cost of failure is almost zero. And you have unlimited potential to scale. That's not a pitch. That is actually what is happening. I love reading your story because as someone who started.

a t-shirt business. You were literally one of the first merchants ever on Shopify. Yep. How do you still have the conviction and the passion to do what you do today all these years later when you've probably run into so many walls, so many problems, so many knows, how do you keep that passion alive decades later? I think one of the great things about careers now is that if you're thoughtful about it, you can actually build your life's work into a career, which is very different than, going back to my grandfather, he didn't care about eggs. He cared about his family. He cared

about philanthropy, he cared about charity, he cared about his community. The egg thing was just a means to an end. I don't have two things. I have one thing. It's Shopify. I love entrepreneurship. It's my life's work. And I'm able to lead a company that does more of that, causes more of that to happen. So I don't know what you want to. You can call it. There's a lot of like the term icky guy, which is, okay, wow. Prepared for you. Wow. I was really excited about this.

So Ike guy, so can you actually articulate the exact? Don't look at my questions, Harley. I won't. You can look at that. What do you love? What does the world need? What can you be paid for? And what are you good at?

And when it all comes together, passion, mission, vocation profession, that's icky guy. So I learned that term years ago, and I love that term. But here's a better version of that, which is a little bit less, I don't know, pretentious. Life's work, where the thing you love and the thing you can make money for and the thing that the world will value for me is the same thing. I think that is. And for some people, my best friend is a big corporate lawyer at some big, you know, fancy law firm. And honestly, he found his icky guy at this big law firm.

And every time we talk, I'm like, dude, like, what are you doing here? He's like, this is it. I love it. He loves being a consigliary. He loves being a coach and a mentor and an advisor for his clients. I think finding that as early as you possibly can is incredibly valuable because the earlier you figure out your life's work, your icky guy, whatever you want to call it, the longer you can practice it.

And then the longer you can get good at it. So Shopify is the only company in my view that like I could spend my life at. But also it's really, really fucking hard. And I really like that because it means that every year my relationship to my work, my job, the craft that I have to develop changes. started as a tiny little company in Ottawa, Canada, four people. Now we're 8,000 people, we're publicly traded. We have a very large market cap, you know, over $100 billion of market cap. Now I have to be good at being a public company leader. I have to go to storytelling. I have to

get good at like culture. I have to get good at like enterprise sales. I didn't know these things. So one of the reasons that I really love it, especially right now is it's at a point where there's so many interesting problems to solve and I get to try all these new things. For me, it's a little bit of a personal growth journey disguises a company. I don't think I've ever said that before, but it's true. It's a personal growth journey for me that I have like different phases, Shopify is about 22 years old. I've been there for almost two decades. Maybe not every year, maybe every two years, it's a, there's a new phase of the company that requires a different skill set. And I love that. I love that I get to keep developing these new skill sets. And

think if you find something like that, your Monday mornings and your Saturday mornings feel exactly the same. And I think it's a strange thing to say, but like when your Saturday mornings, your Monday mornings feel exactly the same, you are onto something. Do you join me about that? Completely. I am going to be very honest and I actually wasn't going to say this, but I'm going to. I think you are changing women's lives more than you know, and I'm going to tell you why. So I was rejected from Shopify 11 times to work there. Hilarious. I did not know. that 11 times? Because I'm from Toronto. Like, I made a TikTok video about this.

When I got on the Shopify Masters podcast, I was like, guys, I was denied 11 times. I kept trying and now I'm on the podcast. And I saw you a year and a half, two years ago. And I was so nervous because I really wanted you on my podcast. And I was just about to launch it. And I was like, oh, my God, like, that's Harley. And I remember took all the guts to go up to you and be like, hi, I'm Maggie. And like, I have this company called Hot Smart Rich. And I had been met from a. lot of other very successful men and or people that had worked at big family offices or big private equity that would hear the name Hot Smart Rich and would either like roll their eyes or say you can't send me an email because your email address is at hotsmartritch.com.

And you were so friendly and open and like I didn't even have anything yet. And you coming on the show today as a publicly traded president, your market cap is over $100 billion. It's like $155.48 billion today. Standing behind the women that need hot, smart, rich to exist to change their trajectory of what they can do in the workplace, it's not just a podcast recording. It's a statement. And I was going to skip over that because I think it's hard to be vulnerable like that. Like I feel I'm almost like about to cry, but I just have to say thank you because I think what you're doing is. and what Shrabify has done

and why I kept applying and kept applying is just like it does change people's lives. And I think it follows one of the principles that you have, which is getting the attention of someone that you admire and want to learn from. I'm so interested. When was the last time that you felt inspired by someone that you admire?

I had a chance yesterday to spend a couple hours of Barry Diller. Barry Diller created IAC. He was at 32 years old, he was the chairman of Paramount. IAC obviously owns Expedia. and like he's one of the most important entrepreneurs on the planet. And I've been trying to get time with Barry Diller for five years. I went through his wife. His wife is Diane Van Furstenberg, DVF.

I've tried everything. I still have that hustle, whatever you want to call it, just like you do. You applied 11 fucking times to shop. I did not know that, Meg, I swear. That like, no, that wasn't my prep notes. So what does that tell me? You could have stopped at number two, three, four, all the way to 11. There is something about grit, resiliency.

And if you're listening to this and you're like, I'm not an entrepreneur, it's not for me, no one ever, I tried a business had failed. Maybe all you have is grit. To be very, very candid and honest, that's the only thing you actually need. And I don't know this, but more than half of Shopify's merchants are women.

True. And again, every 26 seconds, a brand new entrepreneur gets their first sale. since we've been sitting here, there's been a couple dozen for sales. At least one of those will likely be a million dollar company at some point. The difference between

the one that will be a million dollar company, the one that will have this huge successful podcast and ones that won't is just grit. Every time they get rejected or fail, does it reduce their energy or can they maintain it? And ultimately, if you can just maintain your energy, eventually you become too good to ignore. You have become too good to ignore.

That is the key to this whole thing. I have this really good friend John Hope Brian. He runs Operation Hope. He says, if you hang out with nine broke people, you'll be the 10th broke person. Okay, well, let me flip it. That's a little more of John's thing. My thing is, if you hang out with nine entrepreneurs,

you will be the 10th entrepreneur in the group. And I think you have figured that out really, really well, that not only do you have grit, do you not get discouraged, but also like you surround yourself with people that you want to emulate and I still do that now. There are still people that I'm trying to spend time with who don't want to spend time with me. My email address buys me a lot right now because of Shopify and people know who I am. I feel really fortunate.

But I still like Barry didn't want to meet with me until yesterday after years and years. And I'm okay. The meeting with him meant more to meet because he didn't want to meet with me. I just kept going. I was polite. want to be disrespectful or obnoxious, but I made it very clear that he is someone that I really want to learn from. I think he's had an incredible life, incredible career, and I just, I really admire him, and I do that all the time. There's a lot of brands that I think are iconic that are not on Shopify

that don't have really good online shopping experiences. So I'm beginning now to spend more time with some of those luxury brands, the European luxury brands, and they don't care, they don't even know what Shopify is. They think it's Spotify, a lot of them. I will get these brands on Shopify. Not only do I think our product is perfect for them and I can help them with their business and maintain their brand and culture. But I'm just going to outwork everyone else to do it. And I outworked them 20 years ago. I'm going to outwork them now. Give me another 10 years. I'll still be outworking others. I have no choice. That's my operating model. That's my blueprint. This is a weird term to to use, but like there's a give a shit quotient. There's like EQ IQ IQ, give a shit. Like my give a shit

quotient is really, really high. And what it does allow is I get to do cool stuff, but it also allows for a very, very fun life. And I think there's an internet meme, but like it's tough to compete with someone having fun, especially someone who really gives a shit and is having fun. That's the type of entrepreneur I'm trying to beat. I have a confession. Until recently, I had no idea that we've been using FiverPro, our sponsor across Hot Smart Rich, because Katie, who you know and love, handles all of our operations, she has been quietly running HsR like a well-oiled machine. She delegates because she understands that our job isn't to do everything. It's to stay focused on what we do best and bring in the right expertise when we need it.

So a bet a month ago, we had this really complex project that required specific skills. So Katie pulled in a hand-vetted freelancer from FiverPro, who delivered to such a high standard that I didn't even realize it wasn't Katie. Fiverr Pro connects us with the best of the best freelancers working across so many categories, including emerging skills like AI Native expertise. They help us tackle big problems, and they enable us to continue moving while we do.

So if you're scaling a business, then you need to visit pro.fiver.com. It's so true what you said, surround yourself with entrepreneurs, because even like being around you, like, I feel excited, you know? And it's like you want to just go and work so much harder. And I think it's so amazing for you to even say as the president of Shopify, like there are people that still don't want to meet with.

A lot of people really brings me to attention. Because I think for so long we have demonized the word attention. Like it's a bad thing. Oh, she just wants attention. She's an attention seeker. But I think you win in the world if you can garner people's attention. When you're trying to get someone's attention, what is the, the best way, a formula, a framework, an email subject line, like you are trying to get someone's

attention. What is your go-to? Figure out what they care about. No what you care about. No one cares about what you care about. In the case of the people that I've, you know, the names that I brought up on this podcast, the way that I've got in front of them was I found something that they wanted. It had nothing to do with me. And it's somebody's, it's as easy as, you know, a quick search, which is like, you know, what was the last charity they gave to? or what's something interesting that they've done the last couple weeks

what's a movie they just put out what's a business they just invested in if there's someone you want to meet and they just gave a speech at some event

and there's just one and you listen to the speech there's this one line that really matters and you're like wow that line is like mind blowing it's like living

run free in my head put that one line in the subject and that's it I'll tell you an interesting story I haven't shared this in a long time years ago

like 2011 or 2012 we were We had this thing called the Shoplade build a business competition. Do you remember that? Basically, it was start a new business on Shopify. Whoever has the most sales after a year wins $100,000. That was 2010. Turned out that, like, the winner of these competitions were making,

we're building a billion more companies, 100 grand, was it enough? So the idea was, let's give them something as a prize they cannot buy. Let's introduce them to really incredible people. And we brought in like Richard Branson, and I convinced Tim Ferriss get involved and Seth Godin but I really wanted Gary Vaynerchuk at the time he was like peaking

it was like Pete Gary right and he was just I wasn't getting his attention and he just put out a book at that point called Crush It I think it was called Crush It was 2011 or so and there was this website that I don't think it's still available was called 1,800 CEO Reads.com and it showed you how far every book

was from hitting the New York Times Bethlehers list and it showed the number of how many books is left It was like a sliding scale. So I knew that crush it was 3,872 books away from hitting the bestseller list. And I ended up emailing Gary with the subject line.

I want to buy 3,872 books. And that was a subject line like, I don't think there was any body. There was no written body in the email. And of course, anyone who just put out a book knows exactly how far they are from that. And he responded,

and we ended up having him and he was a mentor for the build a business contest for years. He became a friend. I think he's an amazing entrepreneur. I didn't necessarily have any additional resources relative to anyone else to get Gary engaged. What I had was just this idea that like figure out what he needs and what he wants and how can I, how can I offer it? And we ended up buying, I think, 3,000 books at that point from him over

the years. But I knew that if I would have asked him, if I would have created this beautifully crafted, articulated pitch about build a business, why it's so great and why Shopify needs him and all. He would have been like, yeah, that's another email I'm getting, but I knew that by focusing on the thing that he wanted specifically, it would get much easier. That's the way I think to do it is. And I think that is available to absolutely anyone. One thing that I want to say here, because I don't want to mislead anyone. Those emails you send out to people that you want to, you want to meet, one, they're probably not going to respond to you for the first five or 10 messages. But second, you have to, like, you know, I'm in L.A. now doing your show, and I knew I was here.

I was like, who do I want to meet? And I knew I was coming here months ago. So I've been emailing people that I want to meet in L.A. for months now. But I also emailed a lot of people. And I think that is the work that's required to meet these incredible people. Shots on goal. Exactly.

And most people don't want to do that. Being rejected is one of the best blessings I think anyone can ever have because you learn the muscle that it's not so bad. But you just said something so interesting that I think an. expert can only answer to have a validated POV-UMness. You said peak Gary. And I think there's a large conversation, which we're going to get into this creator economy. Is there a peak life cycle for a creator in terms of relevancy over a span of a certain amount of years? No.

I think there's a peak on a per phase basis. We are very close with Jimmy, with the Mr. Beast team. I think Jimmy is amazing I think Mr. Beast is incredible. One of the things that's the most remarkable Mr. Beast and most people don't know is he effectively has

like it's kind of like these boxes like he's got like box one which is like scrap YouTube videos and he gets to the top of that box and then you're like oh he's peeking in that but then what you don't realize is there's another box here and now he's at the bottom of this box

and he goes to the top of this box and you're like well he's peeking like no no no there's another box there are some creators the best ones in my view who are constantly figuring out their next box. And this is very different than, and I think what it was like 10 or 20 years ago,

where athletes, for example, you have these sort of athletes that would have these incredible careers, and then as part of their next phase, they would put their name on, like, I don't know, toothpaste or something, or some, like, random product. And it made sense kind of, if you squinted, but, like, then eventually they kind of just faded out. I think actually what's happening now is you have much more, these creators, the ones that are entrepreneurial, these athletes, the one that are that are entrepreneurial, they have multiple phases of their lives. And I think there's an opportunity to keep reinventing themselves. So yes, it is true that at any one particular phase, you can peak and there's not really anywhere to go, but the ones that are really good that are really thoughtful, they find a new box. For Mr. B's, for example, like the feastable stuff is really incredible.

He just bought a fintech company, a bank, a neobank. It's so remarkable. His business partner house, Jeff, like the way they're thinking about the future of like beast enterprises, like they're already thinking about like the box up here. Therefore, if he's down here, he comes from here, but he's here now and they're already thinking about up here, they have so much room to grow. And I think those are the creators, the entrepreneurs, the makers that have longevity. The ones that I think flame out are the ones that don't get to the top of the box and there's no second act.

Do you believe that every single person that wants to be an entrepreneur selling a company on Shopify needs to have the distribution and the audience, not necessarily even Mr. Beast, but someone to sell to? I think people overestimate how many followers they require and underestimate the idea of a thousand true. My favorite blog post ever written, Kevin Kelly, is called 1,000 true fans. And I think it's like a must read for any entrepreneur. What Kevin Kelly articulates in this blog post is like, that's all you really need. 1,000 people loving what you were doing is sufficient to create this kind of flywheel. And I think a lot of people look at their follower count or something and they're like, 200 followers is not going to work.

Well, if half of those people who follow you are just, are betting on you, care about you, want to support you, that's almost all you need. And it always starts small. I mean, you hear about, you know, all these incredible, going back to Ben Francis, Jim Shark. You hear how big Jim Shark is now. And Ben literally started just by sending Jim Shark T-shirts, not to the biggest fitness influencers, but to people that had like 500 followers, 5,000 followers. And actually, that 5,000 to 50,000 follower band on Instagram for fitness, it's kind of been owned by Jim Shark. because Ben couldn't afford the 5 million follower fitness people. I don't think you need the Mr. B stuff.

I think people have built incredible companies, in some cases, billion-dollar companies, some cases single-million-dollar companies, just selling something to someone who really values it. And, you know, I had this thing. I started the pandemic called Firebelly Tea. I started my best friend, David Siegel. So David's tea and shop, we took our companies public

at the exact same year, 2015. And I met David that year, so it was like 11 years ago. and he took David's tea public on the NASDAQ, and we met, they ended up leaving David's tea, and he kept a bunch of tea in, like, his drawer that only he was really consuming. Like, it was literally it was like David's private collection. And in the pandemic,

I convinced him to build a store on Shopify, and him and I kind of partnered up, and we built Firebelly tea, and it's like, it's like very high-end green tea. Like, it's great tea for people like me that are very high energy. I can't really drink coffee in the afternoon, but like Senta T is perfect for me.

The story and the experience we've had with Firebelly is that you actually don't need Mr. Beast type followers. What you need is a core group of loyal customers. And David literally called everyone of the first customers of Firebelly, asked them what they thought, tried to figure out a way to make it better. And Firebelly is not a huge company,

but it's for the people that buy it, they love it. And I think we live in an era, now where like you anyone can do that you don't need to be mr beast you just have to over deliver to those 1,000 true fans you know direct to consumer as a as a business model it seems like it seems like a nothing well yeah all we basically we cut out the wholesale and now we go direct it's actually a remarkable innovation in entrepreneurship because it means that nobody ever has to beg a retail buyer to put their products on the shelf anymore anyone can now just do it on the their own. And if it works, you scale it. If it doesn't, try something else. It's so true. And it's

like from even working in the celebrity world in the past, like, I think people would be so surprised to see sales results from creator celebrities specifically that have millions of followers that do not get the sales as some of these like homegrown brands that have a diehard community that have a lineup out the door at the Shopify store. Like there are so many of those success stories, which I think I'm so interested on your tape between tradition. celebrity Hollywood brands and like the creator brands, the brand that start with a thousand true fans and why we've seen such success more so with the latter than the former group. It's actually quite simple. It is all about deep empathy for their followers. Okay, so this is kind of

the way business is always was built historically since the beginning of like commerce and retail. So thousands of years. The sequence was build a product first and then build a product first and then build an audience or fight customers. That is swapped, and that's only been very, very recently, like in the last 10 years. Because what happened was you had this concept of people of influence. I don't call them influencers per se, but people that were, you know, were posting on social media, people that were making videos, people that making content on their own in their, living room, wherever.

And they began to realize that this audience that they had was a very loyal audience. And they began to understand that audience and spend time with that audience. and they realized what that audience actually wanted. Everyone brings up Chamberlain Coffee, Emma Chamberlain. If you actually know the story of Chamberlain Coffee, it's very simple. Emma started by building this great community, deeply authentically connected, and began to talk about coffee and began to realize that actually, this community doesn't think there's great coffee beans out there. I'm going to go do something for this community. I'm going to create Chamberlain Coffee, and obviously it's become a huge success.

When you used to go to a concert as a kid, you go to the merch table. And it used to be shitty t-shirts with a shitty screen print. I recently went to a Drake show. We had this great partnership with Drake and the OVO team. And I looked at the merch table. It was a Canada Goose collab jacket. Why? Because Drake, and specifically his team,

Ollie and Matt Babel, they know the OVO audience. They know the Drake audience. And they know that they don't want a shitty screen printed t-shirt. They want an incredibly, well-designed, well-developed manufactured jacket, like a Canada Goose jacket, and they want the

branding like this. And so the celebrities that have had the most success with their own brands, they're the ones that actually understand their audience better than anybody else. And it's worked really, really well, but some random influencer creating a coffee company and trying to be chairman of coffee would never work.

Jimmy created feastables because he himself wanted a particular type of chocolates. That works. You know, people give Kylie a hard time, but Kylie cosmetics is brilliant and it has longevity. Why? Because she started by creating these videos of her trying other people's cosmetics and realizing she can do it better herself. That's why there's longevity. Same thing with Kim on Skims and Emma on Skims. Skims was made because they wanted to do shapewear in a particular way and they didn't like, they were Spanx and they were like,

that's not for me. My community wants something different. Therefore, they created skims and it worked really well. There's this amazing teenager. name Salish Matters. You know Salish? Oh, yeah. Okay. So you know her company? Yeah, sincerely yours.

Sincerely yours. The reason it works is because first she built this authentic connection with this community of like, you know, preteens, like 10 year old, 12 year old, 14 year olds. My daughter, who's nine, love Salish. And then she's like, look, I'm going to create this thing. And she also allowed them to follow the journey. Hey, I'm going to go try this thing. Tell me what you think. Hey, I'm going to try this other thing.

Tell me what you think. Okay, guys, I have a prototype. Hey guys, I have my first samples. Hey, guys, I just created my online store. Okay, guys, guess what? We're live. And by saying it, not only did she create pent-up demand for her products and that she allowed people to follow them the journey by leaving these breadcrumbs,

but she had an audience first and then built a product specifically for that audience. And it was deeply interconnected. And that's the first time the history of commerce that you've seen this flip from product first, audience second. and this is the way it looks. That is very different than the old school Hollywood influencer, sponsor. Like, you know, there's this famous ad in the 80s of Brad Pitt. I think it was Colgate.

He did like a deal with Colgate. It's taught in business school as something it didn't work. But the reason it didn't work because he is not connected to toothpaste. His teeth look fine, but like no one that likes Brad Pitt cares about what toothpaste he's using. And so I think. think at the core of all this is authenticity. The reason that your show works is because you're not acting. Like, I've met you in random coffee shops. You weren't exactly like this. And that's why it works.

And so it's inviting more people into entrepreneurship through this idea of, I have a small community. I'm going to make something specifically for them. And now it's ours. It's not mine. It's ours to share. Do you think that there are anomaly talent, celebrities, creators? So let's take Kim Kaye, for example. Like she has one of the most successful creator brands in the world that I would say is just a global behemoth brand now on Shopify. She just launched Update, like an energy drink brand. But Kim was so known for her silhouette and her shape and like her look that it was a no-brainer for those hundreds of millions of fans to go and buy skims when it launched. Do you believe that she will have the same effect with something like update because she's not necessarily known like the Brad Pitt example for. energy drinks.

If she did update because her community, the people that look to her for influence, have told her either directly or indirectly that they want an energy drink, then it's going to work. And if they haven't, it won't work. But I think in particular when it comes to skims, which I think was called kimono originally, I think all of us kind of follow these breadcrumbs of the story. We remember when the name was, like, I don't really follow all these things, but like, I remember when they switched the name from Komoda to skims. I remember meeting Emma and hearing about how that was going to work. I think good American, another great example. Good American is an incredible business because it feels like it was built for the community that Chloe had cultivated. So I don't know if every one of them is going to work. What I do know is, though, is that we are going to stop calling them creator brands very, very soon if we haven't already because they're just really, really great brands. And I think, the ones that lack authenticity will almost always fail.

They may have a bit of a spike quickly, but if you look back the ones that have been around for a very, very long time, those are the ones that have deep authenticity. And as they evolve, you know, I love saunas, like just some high energy and high anxiety,

so I love sonnas. You know Jesse Hitzler? Yeah. So I love Jesse. He's a great guy. I had a chance to spend a lot of time with him. I did his race 29029 a couple of times. And I got this new sauna,

and I've been loving it. It's been great for me and my anxiety. I was like, I need a sauna hat. The first person I thought about, when I thought about a sauna hat was I went to Jesse's profile on Instagram and I was like, because I was given a sauna hat, I was like, what is you wearing? What turns out all day sauna company is his company?

So of course, like he, like knowing him on a personal level, of course he should create a sauna hat company. It makes total sense. He also owns all day running company because he also loves to run. That's not a promotional product. That's not a one time, one and done type of brand. that will have longevity because it was built for him and his community in a very authentic way.

And I also think about on the athlete's side, you know, the canonical example of athlete-created brand is the Jordan brand. I always thought it was strange that Michael Jordan doesn't own the Jordan brand. I think he gets a royalty and he may own a tiny percentage, but it's owned by Nike. I think part of the reason why that happened, in the 80s when the Jordan brand was being created, he did not have a direct-to-fan highway. There was no connection. Like, he couldn't make something and sell it to his fans.

He needed distribution. And Nike has distribution. And I think what's so cool to right now is distribution has been democratized. So now when you see these athlete brands, we did this thing with Luca Adoncheck here in L.A. It was during NBA All-Star Weekend. So we helped him do this, create this cool pop-up where basically, like, he sold his shoes and his gear. But if you hit a basket, it was like a trick shot.

You get a discount on all the product. It's amazing. It was really, really neat. But it was so amazing because, like, Luca has a huge following. He's a very, very famous, well-known basketball player. He doesn't have to go to some big company. He owns 100% of it himself because distribution for these people is now direct.

When I was growing up, I hated being called a creative. When I was in business, like, I wanted to be Chip Wilson when I was growing up. I wanted to be Chip Wilson so bad that you're Brian Hill. And when someone would call me a creative, I would be like, oh my God, like, I do not. I am not a creative. I'm really good in Excel. I'm very smart. I'm very good at math.

What I love about this evolution of entrepreneurship today is like being a creative is a badge of honor. And I think that couldn't be more important in the world of AI. Should entrepreneurs be scared or excited about AI? Oh, there's no debate. Absolutely has to be excited. So first of all, if you're an entrepreneur, you have to be an optimist. There's no doubt. There's that great quote that pessimists look smart, optimists win.

You have to be an optimist if you're an entrepreneur. There's no room for pessimism. You have to be realistic. and you have to know, you know, when to pivot or make a change, you can't be naive, but you have to be an optimist generally if you're going to be an entrepreneur. I think in this current kind of wave of technology, you have to be a technical optimist. The reason is when you look at how fast things are changing, a week ago I installed OpenClaw on my phone, on Telegram, and I've been playing with it.

It's really cool. This new, like, I think they were just acquired by Open AI, but it was like literally this thing that controls my whole computer and I'm able to, and it runs 24-7. You know, when I shut down, like if you use chat, GBT, you close your computer, it stops running. OpenClauses, this huge evolution. And there was all these things I was frustrated about a week ago. On the way over here, I was playing with it.

Half of things I was frustrated about a week ago, I've all been fixed. I mean, think about that. In less than a week, like, this thing has gotten materially better. Give me another example. I went out for dinner a couple nights ago with Rich from Fashion Nova. And he was asking me about AI in general. And he said, you know, one of you had your mind blown with AI is what he asked me. I said, okay, take out your phone.

And he opened up the Shopify app. And I had him click on Sidekick, which is our AI tool inside of Shopify. Okay, so just to be clear, FashionOva is a huge team. Like, they have a full data analytics team. They're very sophisticated, very, very smart. I know the whole team, like, they're smart people. Ricky and Roger are, like, best of what they do. I think he said, I wonder what is the most popular first name

of on fashionable. Every customer ever, what are the most popular their first name? And I was like, type it in. He typed it in. He got in a second. I said, okay, ask now,

what is your number one customer? Again, this huge company. And he asked, who is my best customer? Give it right away. I said, great. Now ask a sidekick, what should I sell next to this customer? And he did it, and right away,

it's like, this customer's bought these things, therefore we think these skews should be sold to them. that particular customer, she is most likely to buy these skews. Two things happen. One, he was mind-blown. This was happening literally in like milliseconds. But he also said he's like, wow, he's like, I have a huge team of people running my analytics department outside of Fashion Nova. And this tool is available to everybody that uses Shopify. That is why I'm so optimistic. Because in the same way that we have democratized commerce and retail, AI is,

democratizing leverage and information and insights. This idea that everyone has a co-founder, we call it Sidekick, that knows everything about Shopify, everything about your business, everything about retail, knows everything about the world, and it's literally in your pocket, anyone can leverage it. That is really cool. Because if we made it easy to start, AI makes it easy to grow way faster than ever before. So in my view, like, there is no way to be anything but optimistic about what is happening,

especially if you're watching like, you know, podcasts like this and you're entrepreneurial. Maybe you're not an entrepreneur yet looking at you. You should become one soon, okay? But for those that are entrepreneurs are entrepreneurial, this is massive human leverage. And I think anyone who feels, you know, I know there's like the doomers that are like they're worried about all that. I don't believe that to be true. I believe that like this thing is such an incredible new tool that we all have that you may not be able to afford the massive team of data analytic experts that a big company can. But now you have sidekick.

Now you have these tools that are readily available. I mean, I think that's so cool. I think the other term that I'm so interested to hear from you, because I actually haven't spent that much time with this, is agentic shopping. First of all, what is that? So, agentic shopping is just this new front door that you can go to Chatsubit or, you know, Gemini, and you can start shopping there as a new surface area. As a consumer, it's like having a personal shopper. And is it accurate? It's getting much better.

I mean, we're helping to build a lot of that Shopify. So we're trying to make it so that not only is it accurate, but also it has real context of what you care about. If months ago, you did a search for hiking boots and you typed in, I want really light hiking boots. In three months from now, when you go looking for hiking boots, it should only show you really light hiking boots because it knows everything about you. And unlike a personal shopper at a boutique here in L.A., it's, Not on commission. It's merit-based. This idea of agentic shopping also means that you're going to be found, even if you're a smaller business, because, you know, on some of the search engines, it's whoever pays more gets found.

Merit-based shopping is part of the agentic advantage. And I think agentic commerce is actually, like, you have online, you have offline, you have like marketplaces. You have this new thing, I think, called, that is, it's already coming, but it'll get way better the next couple of months, called, called And I think from a consumer perspective, it's going to make shopping very enjoyable a lot easier. From a merchant perspective, it means that it's one more place you can get found. And more and more, the way that I think about Shopify is less about like an e-commerce company and more like a retail operating system where you have this hub. And the hub is Shopify.

And that's where you have your inventory, your customer. It's where you go to do all your work. And this hub is here. Then one spoke is if you have an offline store. One spoke is if you have an offline store. One spoke maybe a pop up. Maybe you also sell on, you know, you have a wholesale business. You sell on other people's stores.

But you have a new spoke called Agenic, which effectively allows consumers to buy directly on all these amazing new tools. And I think it's going to be, it's going to be amazing for consumers. I think it's going to be really amazing for, you know, smaller merchants who may not otherwise get found. I like described as a personal shopper, but it's a personal shopper that only has one objective, which is to delight you as a consumer. That's very cool. What do you think that that means for influencer recommendations? I think there's always going to be a place for that. Back to the agenic side, if the chat knows that you follow, you know, you follow, what's a good example?

Paige Lorenz. Yeah, Paige Lorraine. Yeah, Paige Lorraine. Yeah. If the chat application knows that you light thing page is amazing and you trust her and you follow her stuff, the next time you try to find, you're searching for a sweatshirt or some sort of outfit. for a particular outing, it should know that, like, dairy boy should chill up and think about how incredible that is.

So that's the idea of merit-based shopping with agentic, is that it's not about what it makes an assumption, you know, I'm sure you're walking to a store, and the store clerk says, we think, like, you should buy this. And you're like, I would never wear this. That doesn't happen with agentic commerce. Agentic commerce, agentic shopping is all about what it knows you're going to like because of your entire history of searching. for it. I think that's like,

I don't know, that's really exciting to me. And it's also, it's one more distribution channel. It's like one more way that any brand, even tiny little brands can get found. So is it your thesis that it's not going to replace things? Because I think that's why people are so afraid about this word AI.

It's replacing me. It's replacing the influencer. Your thesis is what with AI? It's a new channel. It's a new place to sell. Look, we have a partnership with Roblox. Where through Shopify, just like you can build an online store and you can sell offline. You can also sell on Roblox.

You can also sell on Instagram. You can also, you can sell in any surface area. The Roblox channel in particular, when it came out, I talked about it. And a bunch of people had asked me, I think I did an interview, like, who's ever going to use it? I was like, some merchants are going to find it to be incredibly effective. And others won't. And that's okay. And to Fenti's, you know, incredible Sopna who runs Fenty Beauty, to her credit, she's like,

you know what? I'm going to get this thing to try. And Sopna and our team and Fenty built this Fenty store inside of Roblox. And we power the checkout and all that for her. We make it really easy. It's an amazing new channel for her and for Fenty. So do most brands should they sell in Roblox? No, not all brands should do that.

But this idea that some brands will have their consumer spending time in different surface areas. Like we have a Spotify channel. Okay. So from Shopify, you can push products to your Spotify artist page if you're an artist. For most merchants in the Shopify, that doesn't make any sense. But Beyonce has Sacred, which is her cosmetics company. She's a huge following, of course, on Spotify. So the fact that now she can deliver her products inside of Spotify to her listeners,

who also love her as an artist and love her as a brand, the more surface areas that exist, the more opportunity that exists. And I think what we're trying to do is we know that with more opportunity, nor surface areas, the complexity goes up. Shopify's job in all, of this, our role in all of this, is to continue to simplify it so that you don't have to worry about it. We will future-proof your business. We will make sure that whatever new surface areas pop up you can sell into with the click of a button. And I, again, you can hear my voice. I don't

think there's anything to worry about other than not playing with these incredible tools. Angels, I hope you are loving today's episode with Harley, the president of Shopify. I was so excited to have Harley on HsR, and I wanted to bring you behind the scenes into the room where the future of commerce actually happens. I am so proud to have Shopify as a sponsor of Hot Smart Rich because this platform is all about empowering entrepreneurs and providing them with the tools to start, build and grow their businesses. Whether you want to sell online or in person, Shopify has everything you could ever need to make that happen. When everything else feels out of your control as an entrepreneur, Shopify acts like a reliable business partner, taking care of the entire backend for

you, your inventory, payments, shipping, orders, and reporting. Literally all of it. So if you haven't already, sign up for your $1 per month trial at Shopify.com slash hsr. That's shopify.com slash hsr. I'm obsessed with anything that makes my money work harder without me doing any more work. Last month, I told you about our incredible sponsor built, which lets you earn points on every rent payment you make to use on flights, hotels, lift rides, Amazon.com purchases, and so much more. Well, as of now, built members can now earn points on mortgage payments too. Crazy. So whether you own or rent your home, you'll get rewarded.

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that fuels your lifestyle because it's expensive. So head to joinbilt.com slash hsr to sign up and start getting rewarded on one of life's biggest expenses. That's joinbilt.com slash hsr. Make sure you use our URL so that they know we sent you. Okay. When I sell my business, I want the best tax and investment advice. I want to help my kids, and I want to give back to the community. Ooh, then it's the vacation of a lifetime. I wonder if my head of office has a forever setting. An IG private wealth advisor creates the clarity you need with plans that harmonize your business, your family, and your dreams. Get financial advice that puts you at the center.

Find your advisor at IGPrivatewealth.com. Amazon presents Jeff versus Taco Truck Salsa, whether it's Verde, Roja, or the orange one. For Jeff, trying any salsa is like playing Russian roulette with a flamethrower. Luckily, Jeff saved with Amazon and stocked up on antacids, ginger tea, and milk. Haboniero, more like Habinier, yes. Save the Everyday with Amazon. As the father of two young girls that want to be entrepreneurs, which I'm going to ask you to read this little letter from your daughters.

Is this real? Yeah. Oh, my God. The last one is the entrepreneur, I think. From Bailey, Harley's eldest daughter nine years old. Dear daddy, guess what? I'm so excited to open a tap and acro jazz dance class for toddlers. I'm going to do with me and Frankie.

I love you so much, Bailey. Wow. From Zoe, Harley's youngest daughter, seven years old. Dear Daddy, I'm so excited to have a lemonade stand when I'm 10. I love you so much, Zoe. So as a father of two daughters that want to be and are entrepreneurs, how are you future-proofing them to be able to build billion-dollar, $100 million, million,

whatever they choose to build businesses in the future? So one daughter here clearly wants to start Dan's class for toddlers. The other one wants to do a lemonade stand. Sorry, I'm getting a little bit of motion to her. I want to do for them what my dad did for me. My dad didn't have a lot of money. My dad was an entrepreneur and he'll probably see this and he won't love this, but it's honest. Mighta wasn't a very good entrepreneur necessarily.

He never made a lot of money. But what he did for me was he made me feel like I can do it. He made me feel like saying I want to be a DJ. he's like, you can do that. It was kind of blind naivete. He was almost ignorant for him to say that. He didn't know, my father doesn't know anything about DJ. But he gave me this confidence that, like, that could be a real thing.

And so rather than go back to my kids, again, nine and seven and say, you know, a dance class for toddlers is not a great idea or a lemonade stand is not, you know, like the meaty thing I think about because this is where my head goes is like, well, what's her differentiation? is it the best lemons? Is it going to be like, what's their distribution like? How do we accept payments? Is there a subscription lot?

No, none of that matters. What matters for Bailey and Zoe is that I just say, yes, and how can I help you? And let them try and let them fail and just give them the whatever you want to call, the swagger, the confidence to just go and try those things. That's the way to do it. Because that business, I still have the business card in my home office. Like those silly business cards changed my entire life. It made me feel like these things were real. And I have friends who, when they've heard the story with the business cards, say to me that when they had crazy ideas, their parents told them they were stupid ideas.

And they weren't trying to be mean. In fact, their parents thought they were helping them. Don't get distracted by these silly ideas. You know, focus on studying, focus on sports. Because that's what their parents thought. I think this idea of defaulting to yes, defaulting to support as parents really, really matter.

And I do that with Lindsay too. Lindsay decided after she gave birth to Bailey, she's like, I want to be an ice cream on ship on her. And I'm like, let's fucking go. Like, how can I help? What do you need from me? And actually, she didn't need anything from me. She actually wanted me to do, like, she wanted me out of the way.

She's like, I got this. I want this to be my thing. I had a tough time with that because I was like, well, what if we, like, she's like, I want to open one store. I'm like, let's open 10 stores. Like, no. So. I think the idea of like knowing how to encourage at the right time and the right way really, really matters.

And I love this. This is amazing. Wow. Harley, I have to do some rabbit fire. Last thing you put on your credit card. Oh, it's a soul cycle this morning. So probably soul cycle. Yeah.

Yeah. Okay. Last most expensive thing. I love 11ty. Do you know 11thi? No. Great brand. I just bought a jack, a bomber jack from them.

Okay. 11T I've it's spelled 11 T Y but amazing brand Shopify brand Shopify brand

that's not a picture for shopper but yeah I bought a jacket from them I love them and they're amazing I wear James purse

basically every day I think James purse is incredible what else I like I like watches but I haven't bought a watch in a while okay

but I want to give you a fun one do you tie expensive purchases like a watch to accomplishments milestones usually yeah

yeah when something really special my life happens because I find it's a nice reminder I bought this watch at the IPO Daytona and every time I look at it reminds me of that you know you and I are both skiers yeah I just bought recently I bought a helmet a pock helmet with Bluetooth built in and I really love that send me to like yeah it's really good actually I don't I know it sounds like I use it's just for music I love listen music when I ski and uh it's a great helmet uh so that's awesome speaking of skiing or building businesses oh both I don't think, again,

You have to be fine, it's a profit fire. Building businesses. That is my, it's my greatest joy in the world is building. Is there a brand out there that doesn't use Shopify that you want to before the end of 2026? Brenelo Cucinelli. Period. Book that every single entrepreneur should read. Early entrepreneur, I think rich dad, poor dad is really great.

Not just for an entrepreneur. I think actually everyone should read your superfood. word at. If you are, like, I read that when I was 13, it changed my view of money and how to manage money. High output management, if you're running a company with a team, is really, really great. Andy Grove, who built hard things, but hard things. Ben Harowitz is incredible as well. Actually, you know, I'll give you a controversial one, may not controversial, but a really important one. It's called anti-fragile. The Simtaleep. There's this idea that if you have something delicate and you drop it, it breaks it's fragile. And if you drop it and doesn't break, it's

durable. There's a third system called an anti-fragility system, like the immune system, where if it breaks, it actually reassembles better, stronger, faster. And actually, I think this whole book basically talks about the system with the anti-fragile system. I think it's an amazing way to go through life, to think about life, that if you look at failure as the discovery of something that did not work, you end up trying a lot more things and being more resilient. And the anti-fragile book itself, anti-fragility, does a really good job of embedding. heading that into your psyche. Beyond that, 1,000 true fans is incredible. It's just a blog, but it's not a book, but I think it's really, really important. Those are the ones.

Is there an industry that you would never start a business in? I love restaurants. We're huge foodies. I know nothing about it. In fact, I can see myself wanting to get into the restaurant business because we love restaurants. My wife and I love dining. It's like our, it's our favorite thing in the world is go to a great restaurant and a great place with a great chef and have a great Saturday night or Friday night or whatever, but I just, I will not get into it. That's probably the one that I would avoid at all cost, mostly because I like it so much

and I know that I'll be very bad at it because I will make bad decisions that are not objective, but rather are based on like, I'm like, let's expand because I want more people here. And they're like, no, no, no, so I'll stay away from restaurants. Okay. One word to describe how revolutionary this product was on Shopify. Brilliant.

because what Road did when Haley did is this to me is more than just you know a piece of silicon and a you know and a lip tint this is empathy this is Haley and the team at Road watching millions and millions of customers all over the world at a coffee shop

at a restaurant having their phone here and their lip kit here or their lip tint here and saying like we can do this better and saying actually the way we'll do it is because the innovation is is not just this, it's also this, right? It's how it actually all fits in together. It's the way it slides out.

This speaks to me of like, they deserve all the success they've had because this tells me that they listen to customers in a way that no one else did. Like, when you see this net, you're like, this is so obvious, but how come no one figured it out? Because they didn't listen the way they did. Road and Haley and the team, they deserve

all the credit they get for this. This is incredible. For non-life-saving products on Shopify, is that one of the most innovative you've ever seen? Oh, that's asking a lot. It's like pig of my favorite child. This is pretty damn innovative. But, you know, that there are like, figs is also incredibly innovative. Trina has become a friend and she's an incredible entrepreneur. She doesn't come from that world. It was a friend of hers who was a doctor. And she's like, I can't believe you're this great doctor at this great hospital and you look like a slump. Like, I can do this better. So I think that's incredibly innovative. I think, yes, there's some brands I'm just, there's some brands. I'm just, there's some brands. I'm just, I'm just, I'm just, I'm just, Shopify, like, I look at Birkenstock, built in the 1700s. They're still innovating. Or I look at Mattel. I've got a chance to meet the team of Mattel and Yonan and everyone there. Mattel was created in 1945. Somehow, like, they keep innovating. Like, forget the Barbie movie. I just, Mattel creations, they do drops. I was driving here today. I drove by the Supreme Star,

which is on Shopify. The lineup at Supreme is still insane. What Kith is doing, with Kith treats, and their collaborations, absolutely insane. Walk into a James Pears store, you can hide all the logos, you can hide the name, you smell it, you're like, James Perstor. How does that happen? Thoughtfulness, people that really, really care. That's why, like, I started the conversation by saying, I pray at the altar of entrepreneurship. I pray at the altar of people that have a really, really high give a shit quotient.

And they make products for people that appreciate that give a shit quotient. And it doesn't have to be fancy. I like these bracelets from M. Cohen because, like, He cares about bracelets. I know the Bombus socks guys for a long time. I think Bombas is so interesting because, like, they thought about small things, like that little rubber inside of the sock so it doesn't slip off. I get to experiences every single day.

Do you know Tukovas? Yeah, the Cowboy Company. Yeah, so, like, I spent a lot of time with Kevin, Team Tukovas. Like, who would have thought that there was room for a modern cowboy boot, direct-to-consumer business model in 2026? And here we are. Why? Because, again, same reason. When you walk into a Toccovis store in New York City or in San Diego or in Austin or anywhere, L.A. or wherever the stores are, you walk in, you're like, this is Tocovus.

Like, you walk in, it's a bar. People are just having tequila shots or having a drink. They're hanging out there. There's people just like having conversations. Companies that really have a deep understanding of who they're serving, of any size, win. And those that don't lose. and I just, I don't know, I'm blown away by the people we get to serve every day. And that's like, it's easy for this to be my life's work. It's easier for me to support you when I first met you because it was so obvious that like, you just really cared. You wanted to have longevity, but you wanted to do in a way that was deeply personal, authentically to you.

And people, the world, the public, the media, investors, and more support your customers, we feel that, we see that. We want to vote with our wallets to buy from companies. that we admire. Small ones and very, very large ones. It's the reason why so many people go out of their way to go to their favorite coffee shop, even though Starwax is closer,

they still go there because they know the person there. The size of the ice cubes are a little bit different, and they really care about those ice cubes. And I think people notice these things. Care more. Care more. If you could title this season of your life, what would it be called?

I am embracing my spiky object. What I mean by that is throughout my life, I thought I had to be well-rounded. When I looked up to see who were running companies of shop device size that we are today, 10 years ago, I saw a lot of very well-rounded people. They were good at finance and product, and they were good at PR and IR, and they were good at business and sales and marketing, and they were good at technology, and engineering, they were good at everything. And I thought that's what I have to be. And it was only a couple years ago that, I think for Toby, this is the same thing. We both sort of embraced our spiky object. He is the greatest product mind, I think, in the world.

certainly in commerce. And I'm a storyteller. And so I'm embracing my spiky object. I'm not well rounded. I'm like this. And I'm just trying to sharpen my point. So I think this is my spiky object era. I love that so much. Okay. Last one. I do these things on Instagram. Have you seen my HsR love notes? So I do have a very toxic brain. And I have to retrain it every single day, this negative self-bad talk. And so an example would be like, I'm going to crush my interview with partly today, even though I'm very nervous and I'm very sweaty. I'm going to have an incredible night of sleep because I'm having trouble sleeping. If you could tell yourself one HSR love note for the rest of your life, what would it be? I am enough. I do this thing called Big Shot. It's this little

weekend project. I'm creating an archive of the greatest Jewish entrepreneurs. And we interview these people in their 80s, 90s, in some case, in their hundreds, self-made billionaires that I really admire people I deeply, you know, look up to. And one of the questions I ask at the end of the interview is, when did you know that you made it? These are people like Linda Resnick who created Fiji Water or Izzy Sharp who created The Four Seasons or Mickey Drexer who basically created the Gap and founder of the Old Navy, like really iconic people. And I just say, when do you know that you made it? And none of them have ever said that they believe they've made it. And it's inspiring, but I also, I'm like, are you crazy?

Like, you created the four seasons, not one hotel, like the entire four seasons hotel chain. Like the brand, the most unbelievable, I think the most legendary luxury run of the planet is four seasons. Totally. And they don't know that they've made it yet. And I would like at the end of my life to say, I made it when this happened, or I felt like I made it when this happened, or when Baylor started, you know, her dance school for toddlers or Zoe did this. And so I think a lot of this content of enough, doing enough, being enough, having enough. And I think that's a double-edged sword back to your question earlier, which is that ambition is really good. But there is a point

where you have to be like, that's good. Like, I'm enough. I've done enough right now. And I don't need that right now. I'm still kind of in my, in my era where, you know, my spiky point era, spiky object era, where I like, I want to grow. I'm not the best storyteller in the world. And I'd like to be. It may take 10 years or 30 years, but by the time I am of the age that I would be interviewed for Big Shot for my own show, and someone says to me, when did you know that you made it? I want to say, I was 65 years old or 75 years old, and I was, you know, sitting on the porch with my grandkids, and I look around and I feel totally and utterly complete. Okay, I have one more question for you. I hope. I think I would be so stupid.

to have one of the best storytellers that I've had on the show, and from one storyteller to another, what is one thing that I could do to improve moving forward as an interviewer? Watch all your interviews. It's hard. I bet you have a tough time doing that. Watch them. Think about your voice inflections. Think about your ums.

Think about, not that you do that, but that's what I do. No, but it's good to get feedback. And I watch all that stuff too. And actually, I'll say this to anyone who's watching. If anyone who's watching wants to become a better storyteller, you know, it's hard to get on the HSR podcast, but there are 700,000 other podcasts. There are plenty of people that would love to have everyone watching on their show.

And if you go on someone's podcast, even a tiny little podcast, you get this momentum. You get the video afterwards. Maybe it's on YouTube. Maybe it's they sent to you a file on Dropbox or whatever. You get to watch it. I actually think one of the greatest ways to become a better storyteller now, in modern days is reps.

And you can do high leverage, low consequential reps by being on all types of random podcasts. Next time a high school tells you they want you to talk to their class about your baked goods business. Do it. But ask your mom to come and record that

and then watch that video. Every amazing athlete that I've met who like is superstar athletes all tell me they watch their tapes. They rewatched their tapes. We've been public now for 11 years. I've done 44 earnings calls. Not only I listen to all of my earnings calls that I've done,

I listen to everyone else's earnings calls too. What they do differently here? You know, one of the things I started doing in the earnings call is I repeat myself now. Q4 2025 revenue was more than all of 2020. I heard that sad. I was blown away by it. So I said that on the earnings call and I said, I'm going to repeat that.

Our Q4 revenue was more than the entire year in 2020. Stop. Pause. Now continue. I learned that by listening to other people. people's earnings calls. Now, a lot of the stuff I listen to other people's earnings calls are terrible. People are inarticulate or they're nervous, but I am able to pick up these little things here and there. And just like an athlete, entrepreneurs are athletes. We just have to train in a

very different way. We can't just go to the gym. But watching the tapes, things we've already done, as smaller as large as they are, that is an incredible hack to just a true self-improvement. Harley, I really met what I said at the beginning of this interview. Like, I have a big vision and it's bold and it always has been, but it really does take people like you to let me interview you without my shoes on, out of my house, and I'm just like truly so grateful that you made the time. So where can people find you? Where can they listen to Big Shot?

When are you coming back on? I'll come back on the time you'll invite me. You know, Instagram, I'm just at Harley. I'm lucky everyone of those first name Instagram handles. You know some people? And yes, I was able to get that. And Big Shot, if you're interested, whether you're Jewish or an entrepreneur or both, bigshot. It's my weekend project.

It's a labor of love. And let me say this. I think what you are doing with the show is more than just you creating a show. You are effectively, you've manifested this. And there's no other way to describe it. You have manifested what you have here. Like you said you want to do it and you're just doing it. But I think what you're also doing, you're showing people that this is possible.

And this idea, like, we cannot do what we don't see. The reason I want people to go to a local meetup, a local entrepreneurial hackathon, whatever it might be, is because when you see back to what my friend John O'Brien says, like, if you hang out with nine entrepreneurs, you will be the 10th. And if you hang out with nine complainers and pessimists, you will also be the 10th. I can't thank you enough. Thank you, gosh, for coming on. Thank you so much.