Harley Finkelstein: We Are Living in the Next Renaissance, How The Next Wave of Entrepreneurs Will Change the World as We Know It | E252

Harley Finkelstein: We Are Living in the Next Renaissance, How The Next Wave of Entrepreneurs Will Change the World as We Know It | E252

Harley Finkelstein: We Are Living in the Next Renaissance, How The Next Wave of Entrepreneurs Will Change the World as We Know It | E252

Growing up, Harley Finkelstein had a passion for entrepreneurship. He became one of the first vendors on Shopify, and his T-shirt company became a survival tool for him in college. He realized that he could never see himself working for anyone else. Harley is now the President of Shopify and a respected entrepreneur. In this episode, Harley unpacks his lifelong journey as a serial entrepreneur. He will explain why we are currently in an entrepreneurial renaissance and how to thrive in the new “connect to consumer” world.

Harley Finkelstein is an entrepreneur, lawyer, and the President of Shopify. Harley is an Advisor to Felicis Ventures and one of the “Dragons” on CBC’s Next Gen Den. He received the Canadian Angel Investor of the Year Award, Canada’s Top 40 Under 40 Award, Fortune’s 40 Under 40, and was inducted into the Order of Ottawa. Harley starred on Discovery Channel’s I Quit, and recently co-founded Firebelly, a modern high-end tea brand.


In this episode, Hala and Harley will discuss:

– How Harley came from “forced entrepreneurs”

– Becoming one of the first vendors on Shopify

– How Shopify revolutionized online business

– The Entrepreneurial Renaissance

– Why more women are becoming entrepreneurs

– Reverse engineering your business momentum

– Why Harley co-created Firebelly Tea

– The Connect to Consumer Era

– Why 2023 is the year of the entrepreneur

– And other topics…


Harley Finkelstein is an entrepreneur, lawyer, and the President of Shopify. He founded his first company at age 17 while a student at McGill University. Harley completed his law degree as well as his MBA at the University of Ottawa, where he co-founded the JD/MBA Student Society and the Canadian MBA Oath. Harley is an Advisor to Felicis Ventures and one of the “Dragons” on CBC’s Next Gen Den. He received the Canadian Angel Investor of the Year Award, Canada’s Top 40 Under 40 Award, Fortune’s 40 Under 40, and was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the Board of Directors of the C100, and from 2017 to 2020 he was on the Board of Directors of the Canadian Broadcasting Corporation (CBC). He is currently on the Board of Operation Hope, a nonprofit providing financial literacy empowerment and economic education. Harley starred on Discovery Channel’s “I Quit,” and recently co-founded Firebelly, a modern high-end tea brand.


Resources Mentioned:

Harley’s Website: http://harleyf.com/about/

Harley’s Twitter: https://twitter.com/harleyF

Harley’s Instagram: https://www.instagram.com/harley/

Harley’s Facebook: https://www.facebook.com/HarleyF

Harley’s Podcast “Big Shot”: https://www.bigshot.show/

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[00:00:00] Hala Taha: 

[00:01:48] Hala Taha: Young and profiters. We have a very awesome interview in store for you today. We're talking to Harley Finkelstein, the president of Shopify. And I'm so pumped for this interview because as most of you know, Shopify is one of my longest running sponsors and I use Shopify to sell my LinkedIn secrets masterclass.

[00:02:07] Hala Taha: We absolutely love Shopify at Yap Media. In fact, we're starting a branded series with Shopify. We'll be interviewing entrepreneurs from some of their top shops to learn about their founder stories, how they scaled and how tech like Shopify gives entrepreneurs the opportunity to disrupt industries like never before.

[00:02:26] Hala Taha: Harley, Podcast.

[00:02:29] Harley Finkelstein: Great to be here. Thank you for having me on the show. Very, very honor. 

[00:02:32] Hala Taha: Yeah, I'm really excited about today's show, young and Profits. It's gonna be a great day for all of us side hustlers and entrepreneurs because we have Harley Finklestein in the building.

[00:02:43] Hala Taha: Harley's an entrepreneur, a lawyer, and the president of Shopify, which is a top commerce platform and one of our long-term sponsors at Young and Profiting podcast. Harley is also an advisor to Licious Ventures and one of the Dragons on CBC's. Next, Jen Den. Which is essentially Canada's version of Shark Tank.

[00:03:01] Hala Taha: He also recently co-founded Fire Belly, a modern high end T brand, and is the host of a new podcast called Big Shot. In this episode, we're gonna unpack Harley's lifelong journey as a serial entrepreneur and will learn how he went from being one of the first users on Shopify to eventually leading the company as its president.

[00:03:19] Hala Taha: We'll discover why Harley believes we are currently in an entrepreneurial renaissance. We'll pick his brain on the future of e-commerce and we'll gain insight on how to thrive in our new connect to consumer world. So Harley, let's start off with your background story. You call yourself a lifelong entrepreneur, and it turns out entrepreneurship actually runs in your genes.

[00:03:39] Hala Taha: Can you tell us a bit about your family history and why you call your parents forced entrepreneurs? 

[00:03:44] Harley Finkelstein: Well, entrepreneurship for me, Has always been about solving a problem. It's sort of the tool that I've pulled out of my tool belt since I was a kid because I wanted to do something and, and it was a challenge.

[00:03:54] Harley Finkelstein: And so the tool that I would use to solve that challenge would be entrepreneurship. That is very different than what my, my father, my mother, my grandparents went through. I. My father came to Canada from Hungary in 1956, and his parents were Holocaust survivors. he'd sort of had a rough time growing up, but they immigrated from Hungary, uh, during the Hungarian revolution to come to Canada in when he was a a little boy.

[00:04:15] Harley Finkelstein: And when my grandfather, his father came to Canada, he didn't have a job, obviously. He didn't speak the language. He had no money. And so the only thing that he had that was accessible to him in terms of making money, putting food on the table, was starting a small business, and he spent pretty much his entire life.

[00:04:30] Harley Finkelstein: Until he passed away a few years ago selling eggs at a farmer's market. He, he got a little kiosk and found a couple farmers and began to sell eggs to consumers. My father had sort of a similar, similar experience when after he, he finished, uh, school. After he finished college. He was looking around trying to get a job, couldn't find one, and he himself also used entrepreneurship as a way to solve his problem.

[00:04:51] Harley Finkelstein: In his case, he was starting a young family and he needed to make money, and so it wasn't as dire as my grandfather, but entrepreneurship and, and becoming an entrepreneur for my father was also. About survival. If you fast forward till I guess, 1996 or so, I'm 13 years old. I'm living in Canada at the time, and I want to be a dj.

[00:05:09] Harley Finkelstein: I was going, I'm Jewish. I was going to a lot of bar and batt mitzvah at the time, and I just thought DJs were just the coolest people I'd ever encountered. They were these magicians where they would take a group of people, a couple hundred people that were sitting down that were lethargic, that were eating their dinners, and within a matter of minutes they would have them doing a Congo line.

[00:05:27] Harley Finkelstein: I mean, it was just, to me it was, it was magic. I want to be a dj. And so I called around a couple DJ companies and of course nobody would hire me. I was 13 years old. I had never had, I had no experience as dj. I probably looked like I was eight years old. And so it just, there, there was just no way it was gonna happen.

[00:05:42] Harley Finkelstein: And my father said, well, why don't you start your own DJ company and hire yourself? And I did. And although my parents didn't have a lot of money, the one thing they did help me with was they, they would make me these business cards, every crazy little idea I had as a kid. My dad would print these business cards on, on the family computer.

[00:05:58] Harley Finkelstein: And so that was sort of the first time where I realized that this, this idea, this concept called entrepreneurship is not only a great way to survive and a great way to, you know, put food on the table, but also most things that I wanted to do, most challenges that I encounter. What if I took an entrepreneurial approach to that?

[00:06:14] Harley Finkelstein: And I've been sort of building companies ever since. 

[00:06:17] Hala Taha: I love that. And it's so true what you're saying. Sometimes we're waiting for gatekeepers to tell us yes, or to give us a job, to hire us. But if we take agency over our own lives, start figuring out how we can leverage our passions and our hobbies to create a business, we can go ahead and do what we wanna do, and we don't really need permission from anybody else to 

[00:06:35] Harley Finkelstein: do so.

[00:06:37] Harley Finkelstein: The number one question I get often when people find out that I'm the president of Shopify, you know Shopify, we wanna be the entrepreneurship company. We wanna be the place where people go with an idea and on the other side of our software, they end up with a business, in some cases, maybe a multi-billion dollar business that changes the world or changes their industry like, you know, an Allbirds or a figs or a gym shark has done on Shopify.

[00:06:57] Harley Finkelstein: So the question I often get is, okay, I love the idea of entrepreneurship. I'm creative, I'm ambitious, but I don't know what to start. I dunno what business to go into. And what's so fascinating is after a line of some very simple questioning, it becomes so obvious to them exactly what they should start.

[00:07:13] Harley Finkelstein: And so I, I start by asking them, you know, what are you into? What is your hobby? What do you do on Sunday afternoons when you're tinkering? What do you do, you know, in the shower in the morning? What are you thinking about? I mean, what kind of ideas? And often they're like, well, you know, I've, like, I, I've been tinkering on this, this idea for a while, and I, I think that I wanna make the most beautiful, you know, kitchen appliance.

[00:07:31] Harley Finkelstein: And it's, it's really cool, but I kind of built it for myself and I'm like, well, why don't you consider building that for other people? In other cases, it's something as simple as, I love making beautiful blankets for my grandchildren.

[00:07:44] Harley Finkelstein: obviously the next comment is, well, what if other people would find value in your blankets? And they would say, well, wait a second here, maybe. Maybe that's it. And it's so funny that there's so many people searching for what they can start their entrepreneurial journey doing. When in fact, it's literally right in front of them.

[00:08:00] Harley Finkelstein: And that's not to say that everybody needs to commercialize their hobbies. Something should just be hobbies. I mean, I, I love yory barbecue. I'm not gonna be ever become a Yory chef. It's just not. But I, I love, I enjoy making it for my, for my kids and for my wife and for my friends. So some hobbies can be hobbies by themselves, but a lot of the time, the hobbies, the things that we tinker on, You know, in our garage after work on nights and weekends, that may actually be the thing that becomes your life's work, and it's right in front of you.

[00:08:29] Harley Finkelstein: Yeah, totally. 

[00:08:30] Hala Taha: And sometimes you start a business just to get you by through a certain period. So for example, when you were in business and law school, from my understanding, you had a t-shirt company and that's how you decided to pay your way through school. You weren't getting money from your parents and you also wanted to make sure you were able to go to school full-time.

[00:08:47] Hala Taha: So you decided, I can't get a job. I need to just have my own business. So tell us about this t-shirt company and how it enabled you to thrive during your college 

[00:08:54] Harley Finkelstein: years. So I mentioned when I was 13, I became a dj. Uh, shortly thereafter, my family and I, we've moved, we moved to, uh, we left Canada, moved to South Florida, and I went to high school there.

[00:09:03] Harley Finkelstein: And all throughout high school I was tinkering on this DJ business and was DJing parties for friends and DJing weddings and DJing all types of corporate events. And it was really fun. I made a little bit of money, but more importantly, I really got deep into entrepreneurship. You know, one of my friends were playing sports on weekends.

[00:09:19] Harley Finkelstein: I was trying to figure out, How to expand the business to figure out what new equipment could I buy that I could rent out to, to clients. And in 2001 I finished high school and I moved to Montreal, back to Canada to go to McGill, and that was the year where our family really suffered some, some real hardship.

[00:09:34] Harley Finkelstein: My dad was no longer around and my mom and sisters, I've too much younger sisters, needed support. And so I knew that I wanted to once again use this tool called entrepreneurship that I had been working on all throughout high school to solve that problem. The problem was, was as follows, I wanted, I, I was a, a first year student in a new city and I loved, I loved gonna school.

[00:09:53] Harley Finkelstein: I wanted to be a student. I wanted to be a regular college kid. Uh, meaning I wanna take a full course load, but I also needed to support my mom and sisters and, and without my dad being around, it felt like I had to do something different. Working a part-time job was not gonna pay the bills, and I wasn't willing to take a, a part-time or a reduced course load.

[00:10:10] Harley Finkelstein: So I began to ask around what kind of business do you think I should start? Just like people ask me now. And a friend of mine said, McGill University spends a lot of money making on t-shirts, promotional t-shirts. So the first day of school you got a t-shirt, a bag, and a hat that says McGill, or says whatever school you go to.

[00:10:25] Harley Finkelstein: A friend of mine said, you should consider maybe doing that. And when I thought about it, I had two unfair advantages. The first unfair advantage was I was a student, so therefore I was potentially going to be making t-shirts for myself. Which I thought had the potential, an unfair amount of, of empathy because I literally was in the shoes of the people that were, or I guess in the t-shirts in this, in that case, of the people that I was going to sell t-shirts to.

[00:10:49] Harley Finkelstein: So one, I felt an unfair advantage because I myself was going to be a consumer of the product I was gonna make. And the second thing was Montreal has a very rich industry, garment industry. It's, it's, Some of the biggest clothing companies on the planet were built outta Montreal. So I knew that I had access to screen printing machines, and I had access to people that had been in the business for a long time if I only, you know, I just had to find them.

[00:11:11] Harley Finkelstein: And so all throughout college, all throughout my undergraduate degree, I made t-shirts for universities. It started with McGill and then expanded by the end of. My undergrad, I was making, you know, t-shirts for dozens of universities all across Canada. I would say that was me. Really the focus there was really more on forced entrepreneurship rather than passion driven entrepreneurship.

[00:11:30] Harley Finkelstein: I like t-shirts, but I, that wasn't really what I wanted. That wasn't gonna meant my life's work. It was a means to an end, and I, I needed to make money. And it turned out it was, it was a really good business. We didn't make a ton of money, but we made enough money that I was able to afford tuition and help.

[00:11:43] Harley Finkelstein: My mom and sisters. A mentor of mine convinced me as I was finishing college. To consider going to law school. And the, the hypothesis that he had at the time was law school will be like finishing school for entrepreneurship. You'll learn how to write better, how to be more articulate, how to think differently, how to critical reason.

[00:12:00] Harley Finkelstein: And this particular mentor happened to be teaching law at the University of Ottawa, which is the capital of Canada. And he said, why don't you apply to the University of Ottawa Law School and if you move here, you know, at least you'll have me in town cause I'm gonna be teaching there next year. And so I applied to one school, uh, university of Ottawa, luckily got in and I moved to Ottawa in 2005.

[00:12:18] Harley Finkelstein: Had no friends, had no family here. And the second I moved here, I did what I always had done was I tried to find my tribe. And by that point in my life, I was 21 when I started law school. My tribe were the entrepreneurs. They were the people that I just, I always got along with them. I felt like a real community.

[00:12:35] Harley Finkelstein: And even though all the different entrepreneurs were all in different industries, there's something that like when you start a business and you're responsible for payroll, you're responsible for covering the cost and covering overhead. Something changes, some, some sort of chemical changes in your brain.

[00:12:50] Harley Finkelstein: And the only other people that really can understand you are other entrepreneurs. And so I'd asked where all the, the entrepreneurs hung out and I was directed to a coffee shop. And I met a group of really incredible young entrepreneurs, and one of those entrepreneurs was this programmer, this brilliant programmer named Toby.

[00:13:07] Harley Finkelstein: And he just moved to Canada from Germany. And he was telling me that he had built this online snowboard store. And he thought the snowboards were a good idea, but the software behind the snowboard store was a really great idea. And he was gonna stop selling snowboards and focus on the software and allow other people to build beautiful online stores.

[00:13:23] Harley Finkelstein: And I thought that was an amazing next. Evolution or next edition from my t-shirt business. Moving from promotional t-shirts to direct to consumer retail t-shirts, and I became one of the first customers to use Shopify in 2006. It's so 

[00:13:36] Hala Taha: cool. You know, Shopify is such a big household name now, and to think that it really started off as a shop where Toby was selling snowboards and he just thought, oh, from my understanding, people were asking him, can I use this software for my own business?

[00:13:51] Hala Taha: So let's talk about what it was like to start a business before Shopify. Like how did Shopify really revolutionize small 

[00:13:58] Harley Finkelstein: business? Okay, so let's talk about the history of entrepreneurship. And if you go back, if you think about the history of entrepreneurship, it is the history of currency, which is about as old as time.

[00:14:08] Harley Finkelstein: So the idea of starting a business, the idea of commercializing something, selling something to somebody else goes back thousands and thousands of years. The problem, I think, is that the main ingredient historically starting a business was capital. You needed money. And so if you read any business books about the Rockefellers or the Rothchilds or the standard belts, In every one of those early stories, there's always a banker or a bank involved.

[00:14:34] Harley Finkelstein: Someone goes to the bank and takes that a loan, and then with that loan, with that capital buys infrastructure, buys a building, buys raw materials, hire somebody. And so effectively, up until very recently, you needed money to start a business, which. Okay. If you had access to money, that's great, but most people, I certainly had no access to money.

[00:14:51] Harley Finkelstein: So that was outta the question for me. But it also meant that if you, if the business did not work out, the cost of failure was dramatic. So much so that in many cases, even still today, when people take out these bank loans to start a business, They're leveraging their house. They're taking a second mortgage out.

[00:15:07] Harley Finkelstein: If they don't have a mortgage, they take a mortgage on their house. They're using credit card debt in some cases cuz they have no other access to capital. But that idea that you needed money to start a business is so very much baked into the fabric of entrepreneurship. And what I think changed in the kind of early two thousands as the internet began to become more prevalent as access to the internet from a consumer perspective became more prevalent, was all of a sudden, for the first time maybe in the history of the world, the made ingredient was no longer just capital.

[00:15:37] Harley Finkelstein: It was beginning to shift towards resourcefulness because what happened was technology software in particular gave anyone leverage It gave everyone these superpowers. So here you have this brilliant immigrant from Germany who comes to Canada in the early two thousands, cuz you met a girl here in Ottawa and he needs to, he needs to get a job.

[00:15:58] Harley Finkelstein: He can't get a regular job because he's, he doesn't have his, working papers. He's not a landed citizen of Canada. He doesn't have a social ins insurance or security number. But he's told, Hey, you can go start a business. And he looks around and he sees there's lots of snow in Canada and decides I'm gonna start a snowboard business.

[00:16:12] Harley Finkelstein: And then he looks at what tools are on the market to do so. And you basically have two options. You either have to sell on a marketplace like an eBay or an Etsy type marketplace at the time where it's easy to sell, but you're not really building your own business. You're effectively renting customers from the marketplace.

[00:16:28] Harley Finkelstein: Or you have to spend a million dollars to have a company like IBM build you, uh, an online store. the ingenuity and, and the thoughtfulness of Toby's decision was, I think I can do better. What if I wrote a piece of software myself to allow me to sell these snowboards? I can have independence, I can have a direct relationship.

[00:16:46] Harley Finkelstein: It's not gonna cost me a million dollars. And that was really the genesis of Snow Devil, which was the that original snowboard shop. So now, now you're in 2004, 2005 or so, and there's very few online stores. E-commerce as a percentage of total retail is probably sub 2% at the time, like 98% of retail still happening in brick and mortar stores.

[00:17:06] Harley Finkelstein: Maybe one or 2% is happening online. I'm being generous. There, but Toby has built the software to sell these snowboards and PE and he starts talking about the journey of, of building an online store. And because of his relationships in the Ruby On Rails community and because of his relationships in the entrepreneurship community, he's hearing from all these different entrepreneurs like me saying, Hey, what you built here is dramatically better than anything out there.

[00:17:28] Harley Finkelstein: Maybe I can build an online store. Maybe I can try my hand at modern retail. And so by focusing on the software rather than the snowboards, he's been able to change the, the main ingredients. And Shopify's been able to change the main ingredients in terms of what do you need to build a great business.

[00:17:43] Harley Finkelstein: And effectively the last 15 years or so has been spent on inviting as many people as possible to join this idea of entrepreneurship. If you have an idea in the shower and you have ambition, it's interesting. Nike did this really well. Nike convinced the entire world that if you have a body, like an actual human body, you are an athlete.

[00:18:04] Harley Finkelstein: As opposed to if you get paid to play professional sports, you're an athlete. Or if you play division one football, you're an athlete. Nike convince anyone that if you have a body, you, you are an athlete and therefore, They sold shoes to athletes, which is everybody. what we're trying to do with Shopify is we're trying to, we're trying to do something similar, which is if you have ambition, if you have interesting ideas gnawing at you in the shower and while you're walking to the bus or where you're on your way to work, or in the car sitting in traffic during your morning commute, maybe you are an entrepreneur.

[00:18:33] Harley Finkelstein: And the idea of transitioning from aspirational entrepreneur to actual practical entrepreneur, I think is made possible or made much more possible. Because of software like Shopify, and today we have millions of stores on the platform. I think we're about 10% of all e-commerce in the us. But for anyone listening, if you, you know, if you think about your favorite brands right now, I'm wearing KISS sneakers, James PERS Pants, and a Blue Salt hoodie.

[00:18:56] Harley Finkelstein: All my favorite brands all have beautiful, incredible online stores and, and they're all powered by Shopify. 

[00:19:03] Hala Taha: Yeah. Honestly, guys, I have to say I love Shopify. Shopify is one of my sponsors, and I'm not just saying this because they're one of my sponsors, but I have a Shopify store and it took us a couple hours to put up the store and I sell my masterclass LinkedIn course on it.

[00:19:19] Hala: I'm one of the biggest LinkedIn influencers and we've made over $200,000 in like five months on our Shopify store just using our built-in community. No paid ads, nothing. Just sending people to our Shopify store. That took a couple hours 

[00:19:31] Harley Finkelstein: to put up. And you think about how you think about that, like that was impossible 10 years ago and 20 years ago, that was unfathomable.

[00:19:38] Harley Finkelstein: No one even had the au like audacity to even consider. I can start something at my mom's kitchen table or at a coffee shop, and that may become a multi-billion dollar company. When you look at people like. Trina at Figs, or you look at Ben Francis at Jim Shark, or Tim and Joey at Allbirds or any of these, Richard at Fashion Nova.

[00:19:57] Harley Finkelstein: You look at these brands that didn't exist 10 years ago and today, they're not only great companies, they are leaders in their spaces, in their verticals, in their industries. That never happened before. No one who started a company 10 years earlier was a leader in their space in the history of business and commerce and retail until right now.

[00:20:23] Harley Finkelstein: Yeah, and I 

[00:20:24] Hala Taha: think one of the main things that I, that really stands out with Shopify is the fact that you have direct access to your customers. So if you're on an Etsy or an Amazon or an eBay, you can't really keep track of your customers or retarget them or send them email campaigns, and that's a really big part of the process when you're trying to build a brand.

[00:20:42] Hala Taha: So I think that's a really big differentiator to me. 

[00:20:46] Harley Finkelstein: Well, that's why, you know, you mentioned this earlier, but one of the things that I've been, I've been thinking a lot about and writing a lot about is this idea of, of an entrepreneurial renaissance. And I think the reason that we're living through some of the most interesting times, and if you will, if you'll follow me for a second, we are living through an entrepreneur renaissance, is because for the first time ever, the only thing you need right now is ambition.

[00:21:07] Harley Finkelstein: Now you have to build a great product or a great service. I mean, your course is successful not because of Shopify. Your course is successful because it's a great course and you're delivering a lot of value, but the opportunity or the ability to bring it to market, to do, to have distribution that anybody in the world can buy your course and learn all this amazing new skills that is powered by technology.

[00:21:30] Harley Finkelstein: And Shopify leverages the technology and the software to do this, and. Think about just in terms of geographic distribution, you can sell your, I mean, I don't, I dunno if you know this, but do you, do you know how many countries your course, uh, people buy your courses in? 

[00:21:43] Hala Taha: I can see in Shopify when people are, where people are logging in from and it's like a dopamine 

[00:21:48] Harley Finkelstein: rush.

[00:21:49] Harley Finkelstein: It's amazing, right? You see this incredible map of people all over the world that want to consume your products and your services. Again, go back 20 years ago, in order to do that, you had to open up locations and every one of those countries, and now you don't. And so in many ways, there's a lot more people participating in entrepreneurship today.

[00:22:05] Harley Finkelstein: And so you can sort of say, well, doesn't that mean there's more competition? Well, yeah, certainly there are more people doing it. But if you are ambitious and you have a great product or great service and you want to get into the hands of consumers all over the world, there has never been a better time to do so.

[00:22:18] Harley Finkelstein: And I mean, you're already doing so well, you know, you're running with what you're already working on. But Hal, think about people who fundamentally like don't know what to do or what to try. They can try five different things, and if four fail, that's okay because the cost of failure today is so damn low and they can focus on the one that does work.

[00:22:36] Harley Finkelstein: Or maybe all five fail and they could try another five things. That idea that you can start, try your hand in a business that may change your life, may change the entire world, may change the industry for the price of a couple cups of coffee at Starbucks. I mean, that is incredibly compelling and meaningful to me, and I, I, I think that's remarkable.

[00:22:54] Harley Finkelstein: I. Yeah, 

[00:22:55] Hala Taha: I think that's really amazing, the fact that people can iterate until they find something that sticks and then they can invest in scale and to the thing that actually sticks. And you can fail 10 times and it doesn't really matter. It it, it's not a big investment like you said. I'm gonna touch on that later, but first I wanna understand how you climbed your way to become the president at Shopify.

[00:23:15] Hala Taha: So you were always an entrepreneur. You probably had a couple choices after you graduated school. Start my own company or join Toby. So how did that all come about? 

[00:23:25] Harley Finkelstein: I had this moment. I was sitting in tax law class five minutes from where I'm standing right now in Ottawa and in a matter of, I think the.

[00:23:33] Harley Finkelstein: Course was three hours. It was three hour lecture. In that three hour lecture, I built store 136 on Shopify. It was a T-shirt, t-shirt store. And I remember that feeling of hitting the launch button and then getting my first sale probably an hour or two later. And just to be fully transparent, I, I'm pretty sure the first sale came for, I don't remember exactly, but I'm pretty sure that came from like my mom or a friend of mine who I was talking to.

[00:23:57] Harley Finkelstein: But that feeling that I was able to build a business in a matter of hours. And then by this time I like, I sat down in the tax law class at the beginning of the lecture as an aspiring entrepreneur, and I walked out of that lecture three hours later as an entrepreneur selling t-shirts all over the world.

[00:24:15] Harley Finkelstein: That was incredibly, that changed my life. It changed my life, not just because the t-shirts made money. It changed my life because it opened my eyes to what is possible when you marry ambition and technology. What is possible when you marry a great idea with incredible software. And I think part of it was after that I knew the T-shirt thing was gonna be a good thing for me to do from a financial perspective.

[00:24:37] Harley Finkelstein: You know, law school and, and business school is expensive. And my dad at that point was still not around. I. And so it helped me do all the things I needed to do in the short term. But in the long run, I think it was quite clear to me, now that my life's work, my icky guy, if you will, was going to be helping other people try their hand in entrepreneurship and helping more people experience this idea of self-actualization and independence and survival and creativity through the lens of of, of business creation.

[00:25:05] Harley Finkelstein: And if I want to do that, there's only, there was only one company that I thought was doing it that had any shot at becoming the World entrepreneurship company and it was Toby and it was Shopify. And so I finished school and I called Toby as I was finishing and I asked him if I can come and join him, and a small handful of others, mostly engineers, and I walked in and said, I'm just here to help.

[00:25:24] Harley Finkelstein: I don't care. What you call me, I don't care what my title is, I don't care about anything. I just want to help build this thing. And for the most part, my job for the first couple of years was like this kind of Swiss Army knife. Let the engineers and designers and r and d folks build incredible software and.

[00:25:40] Harley Finkelstein: We haven't have always had some of the smartest people building software here on design, engineering, development, programming side. Incredible product minds getting together. I mean, Toby's vision around product is unrivaled in, in my opinion. But my job was how can I help? How can I commercialize this? How can I get more people to try it?

[00:25:58] Harley Finkelstein: How can I, you know, we didn't have a C F O when I started. We didn't have a cmo. We didn't have a, had a, like, there was nothing. It was just a bunch of people building really great software. 

[00:26:05] Harley Finkelstein: And because I think I found a company whose mission, like if you think about Shopify's mission and like my personal Harley's mission, the Venn diagram overlap is almost entire.

[00:26:15] Harley Finkelstein: It's, it, it almost completely overlaps because I care so deeply about entrepreneurship because of what I've, I've experienced what my grandparents experienced, what my parents experienced. So like, I believe in the value of, of what this is, and there's no company that that allows me to drive that, to have a bigger impact in that vein than Shopify.

[00:26:32] Harley Finkelstein: That was about 14 years ago, and I've been here now for a third of my life. And, and in terms of becoming president, just, I've always sort of looked at my role here as how can I have the biggest impact, whether it's, you know, starting a partner program or a referral program for agencies, or helping to build the first app store or the theme store.

[00:26:50] Harley Finkelstein: For helping to develop Shopify Plus or enterprise offering, going, taking the company public in 2015 on the New York Stock Exchange, I'd never taken a company public before, so therefore my job was given the skills that I have, given the the ways I think I can, I can add value, how can I be as valuable and as impactful as possible through the process and even to this day, my, usually when someone asks me or tells me about a problem, I.

[00:27:12] Harley Finkelstein: My first answer, my first reaction is, how can I help? And I think if you go about, if you find a place that you really love and you feel like you can do your life's work there, I think it behooves all of us to just be too good to ignore, add as much value as you can, and everything kind of takes care of itself that way.

[00:27:28] Harley Finkelstein: Yeah, 

[00:27:28] Hala Taha: I totally agree. And I think something in terms of your journey that I took away from is that you don't need to be an inventor or a founder to be an entrepreneur. Like I very much consider you an entrepreneur as the president of Shopify, even though you didn't necessarily invent or found the company.

[00:27:42] Harley Finkelstein: That's right. Because some, as it doesn't, it doesn't matter necessarily. Right. Like. I think about this a lot. So Shopify, we are about 10,000 people at Shopify. And if you think about it, like a lot of people that work at Shopify really self-identify as entrepreneurs, not just because they think it's cool, because fundamentally, like a lot of us have, like we started companies, we're founders ourselves, we started, we have businesses running.

[00:28:03] Harley Finkelstein: I mean, I had this tea company called Fire Belly that I started a little while ago during the pandemic that I love. So Shopify very much is a company. Building software for founders by founders. So you have so many great entrepreneurs working at Shopify. Now, could all of us go out and build our own small companies, or even medium size companies, probably.

[00:28:22] Harley Finkelstein: But the way to get real scale and real leverage and the way to sort of get the sounds so cheesy, but like the one plus one equals 10 is by all of us sort of combining our efforts, combining our energy, combining our passion, combining our hours in the day. For a single pursuit for a single mission, which is make more entrepreneurs, help more entrepreneurs be successful, and I think that.

[00:28:45] Harley Finkelstein: You can choose to go do your own thing. You know, some of my best friends are one person businesses or two person businesses that they run and they love that. But I wanted to have a bigger impact and specifically around how do I help more people become entrepreneurs? And again, there's no company that does it better.

[00:29:02] Harley Finkelstein: I think you have to sort of like you can work at a company and still be an entrepreneur. Totally. You can feel like this is like shop has always felt like my baby, but I'm not the founder. Toby's the founder. But Toby has always made me feel like this was also my baby. And that's one of the great parts of working for an incredibly inspiring, thoughtful leader.

[00:29:20] Harley Finkelstein: And you wanna seek those out. You wanna, you wanna look at like, Are the people that you're working for, the people you're working with, the people that work for you, are you surrounded by people who have the same ambition, drive, and frankly character? And if you do, why would you ever wanna leave And so dismiss some of the spells of your title or you know where you are in the org chart.

[00:29:41] Harley Finkelstein: I find that stuff works itself out over time. I didn't start out as Shopify's president. I've worked really hard to, to show my values, so, I still believe every single year my job is to requalify for this role, and if next year I don't requalify, then I'm not entitled to have the honor of being the president of this company.

[00:29:59] Harley Finkelstein: I think that's a really great way to think about your careers. 

[00:30:01] Hala Taha: I. Yeah, totally. I know from my own experience, so I'm the president of a company called Yap Media. We're an award-winning social media agency. I have a podcast network and now I have business partners. So I started as the inventor, as a founder by myself, and now I'm giving equity to the people who, like you mentioned, were there to serve from the start.

[00:30:21] Hala Taha: And then eventually, you know, they become your business partners and they're entrepreneurs equally as much as I am, even though they didn't invent the company. 

[00:30:27] Harley Finkelstein: And you can go so much further now because you have deeply committed people around you all rowing in the same direction. You can just do so much more that 

[00:30:35] Hala Taha: way.

[00:30:36] Hala Taha: Yeah, and they fill my gaps, like where I'm not the most operational, I've got the big ideas and you know, they're the ones executing a lot of the times. 

[00:30:43] Harley Finkelstein: It's so interesting you you say that holla, because I actually think a lot about this. One of the other questions I get is, I'm looking to start a business.

[00:30:48] Harley Finkelstein: I need to find a co-founder. I'm thinking, starting with my like, Sister or brother or friend, most people end up starting businesses with people that are just like them. In fact, you notice this, if you look at a lot of early founding teams, they all went to the same high school together or the same college together.

[00:31:05] Harley Finkelstein: They lived in the same dorm together or dorm room together in the case of Facebook, for example. But actually, the people that you want to build a company with, for the most part, need to have very complimentary skill sets. Not the same skill sets, but rather. Like figure out everyone's yin to everyone else's yang.

[00:31:21] Harley Finkelstein: And that is not necessarily the person you were friends with in high school. In fact, it may be the opposite. So if you are, you're a listeners right now, and you're in college and you're in a faculty of management business, or you're in faculty of engineering, you are probably going to have more success starting building, scaling a business with someone who is not currently in your faculty.

[00:31:41] Harley Finkelstein: In fact, I would suggest that it is. You will find more alpha, more leverage, more abilities if you, as the engineering student goes across the street to the law school. And then after the two of you get together, you then go across the street to, I don't know, like the hospitality faculty. And those are the people you sh you should get together because all of you are gonna bring something so different to the table that ultimately you are gonna form an incredible relationship and everyone's gonna kind of know their place and what they can work on in a really nice way.

[00:32:11] Harley Finkelstein: Which I don't think you'd get if you're just gonna start a business with the person that you've hung out with for the last 20 years. 

[00:32:16] Hala Taha: I totally agree. Let's talk about the entrepreneurial renaissance. You say that entrepreneurship is having a Renaissance moment, and you recently tweeted three reasons.

[00:32:25] Hala Taha: Number one, more people are starting businesses than ever. Number two, creators are the next generation of entrepreneurs building brands, and number three, large established businesses are modernizing their tech stack. So I'd love for you to shed more color on each one of these points and tell us why this entrepreneurship renaissance is happening 

[00:32:43] Harley Finkelstein: right now.

[00:32:44] Harley Finkelstein: Well, the fact that more, more people today, so if you look, if you like, don't take my word for it. Let's just look at the actual numbers. If you look at business registrations, the US business registrations, and you go to the Census Bureau, the US Census Bureau, it's all public information. They, they had this great pdf effectively since 2004, till 2018 or 19 or so, you saw approximately 4 million business registrations every year.

[00:33:08] Harley Finkelstein: It was fairly consistent. It's pretty flat. And then something happened as sort of the pandemic kind of came about. You saw this spike. It actually went from 4 million a year to 5 million a year. I mean, that is, that's a fairly large jump. And now we're actually sitting at that 5 million, uh, mark pretty much every single year.

[00:33:26] Harley Finkelstein: So just from a strictly objective criteria perspective, there are more people today, if you just look at the US alone, starting business ever before. Then there's two other things. Then there's sort of the, the philosophy, this idea that failure is the successful discovery of something that didn't work, as opposed to failure being a scarlet letter that you wear with you, that you, you know, it affects your esteem, it affects your ability to function.

[00:33:50] Harley Finkelstein: That is also changing. Because the cost of failure is so small, people are not realizing that they may wanna try two or three things and see what works, and, you know, throw a spaghetti at the wall and see what sticks. And the, the spaghetti noodle that sticks, that's what they double down on. So first of all, there there's less of a connotation, negative connotation that if I start something and, and it fails, it means I'm a failure.

[00:34:09] Harley Finkelstein: Instead, it feels a lot more like if I start something and it fails, maybe it just wasn't the right thing. Let me try something else. That's the first thing. The second thing is you have this new emergent, uh, I actually tweeted also about this, that, you know, the creator economy is fake. It's just the economy, and obviously that's a little bit tongue in cheek.

[00:34:26] Harley Finkelstein: But what I meant by that is usually when you're starting a business, you start with product and then you build an audience. So I want to build the world's greatest pen. And I'm gonna bake this pen and then I'm gonna go and find people that want to buy this pen or using the example earlier I made this new appliance or this new beautiful blanket and I'm gonna make more of it and then I'm gonna go and sell it.

[00:34:44] Harley Finkelstein: Well, for the first time ever, you actually have people now that first have audiences that are thinking about how can I add more value to my audience? And it's not just, you know, obviously all everyone talks about, you know, Mr. Beast and I have some feast balls here. But it's not just Mr. Beast, like all of us are on, not all of us.

[00:35:01] Harley Finkelstein: A lot of us are on social media. We inherently have audiences. You may have a hundred thousand followers or you may have five followers, but you have an audience. And if you are putting out content and you're putting out information that is valuable to them, you have a really good relationship with that audience.

[00:35:17] Harley Finkelstein: They, they trust you. They want to hear from you, they'll understand you. And so now if you are putting out great content about the future of. The skateboard industry. That's one of our new store Supreme, which is one of my, my Moby Dick was Supreme. I really wanted to get Supreme on Shopify for a very, very long time.

[00:35:32] Harley Finkelstein: And finally, now they're, they're on Shopify. If you're putting on great content about the, about the skateboard industry, maybe you should think about designing a skateboard. If you're, if you go a blog about, you know, soccer for example, and how, you know, the soccer industry and soccer come into America versus the World Cup, maybe you should start selling soccer balls because you know, your audience already has an interest in that particular category.

[00:35:52] Harley Finkelstein: So actually, I think this idea of, of the creator economy, it's just the economy except. There's this, this really cool advantage, which is that you have a built-in audience for your products. And maybe third of all, just sort of on the, the larger companies, a lot of companies either never sold direct to consumer.

[00:36:08] Harley Finkelstein: If you think about the CPGs, for example, H'S. Ketchup size, a store on Shopify H's. Ketchup never sold direct to consumer. Hines would sell through a grocery store. But there's some people that really care about, like they're obsessed with ketchup. They love ketchup and they wanna buy direct from Hz called Hines at home.

[00:36:23] Harley Finkelstein: And for the first time ever, those big brands are actually having direct relationship, whether it's through social media. And if remember years ago, the Wendy's account was like had a real personality and, and a lot of these, so social media accounts of big brands actually have personalities to the extent that their fans, their consumers want to inter.

[00:36:39] Harley Finkelstein: Interact with them. And so you have a couple things happening with the big companies. One is the big companies are beginning to act a lot more entrepreneurial. They wanna have a direct relationship than a consumer, but also they're experimenting, they're trying new things. A couple years ago, one of the cool things I thought that Oreo did, which is owned by Mondelez, is you can put for as a Christmas gift or holiday gift, you can personalize Oreos.

[00:37:00] Harley Finkelstein: So there's someone in your life that loves Oreos, you can make Harley's, Oreos, happy holiday, something like that. That is really interesting. So each of those things on their own are kind of interesting. When you combine those things, you see big companies acting very entrepreneurial. You think you see creators just on the creator side think about these artists like these musicians, people like Drew House with Justin Bieber's brand that he built, or O V O with Drake has built.

[00:37:25] Harley Finkelstein: You see, these traditional would be a traditional musician. Completely expand their scope of what they're actually building and selling and creating. When I used to go to a concert when I was a kid, I would go to the merch table. It was usually some sort of like shitty screen print on some basic t-shirts, like Fruited Loom t-shirt, and it said like, I don't know, the Rolling Stones on the back was a bunch of tour tour dates.

[00:37:46] Harley Finkelstein: Well, now you go to these concerts and you go to like a Drake concert and they're selling a Canada Goose OVO collaboration collab jackets, or you go to a Pharrell concert. And you see some of the crazy stuff. He's, he's selling that like cosmetics at the concert that he, that he's created himself. So big companies are actually entrepreneurial artists are now actually expanding from just being, uh, artistic creators around music and art and film to actually creating product.

[00:38:13] Harley Finkelstein: And then of course you have just more people generally becoming entrepreneurs and more people saying, I make amazing chicken soup and now I'm gonna sell that chicken soup to the world.

[00:38:23] Harley Finkelstein: And I think when you combine all those things, you see people that traditionally had not entered entrepreneurship doing so, and they're scaling at a pace that just has never been seen before. And that's why that's a long answer to a very short question, but that's why I think there's an entrepreneurial renaissance happening.

[00:38:46] Harley Finkelstein: Yeah, and 

[00:38:47] Hala Taha: I'm gonna ask some follow up questions and, and you hit a lot of points, and we talked a little bit about this in the beginning in terms of the fact that it's not as costly to launch a business anymore. It's not as risky. You can iterate. There's not a lot of shame around having a failing business anymore.

[00:39:04] Hala Taha: Also the fact that you just need to be creative now to, you just need a good idea to launch a business. So I have a couple follow up questions. One is about women starting businesses. So as I was preparing for this show, I was surprised to learn that more than half of the business owners on Shopify are actually women.

[00:39:21] Hala Taha: 49% of people who started businesses in 2020 were women. So why do you think that women are embracing entrepreneurship? 

[00:39:28] Harley Finkelstein: A couple things. I can tell you just my own, my own experiences. So my grandmother became an entrepreneur in her fifties. My maternal grandmother. She, she started a little textile business because honestly, she want my grandfather's business was not going the way, the way he wanted.

[00:39:42] Harley Finkelstein: And she wants to supplement their income. And she was, she wanted to actually help with that. She wanted to participate in commerce in the economy, and so she did. So in the sort of the vein of forced entrepreneurship in 2016, my wife and I were. We had our, our first child, we had our daughter Bailey in 2016, and we would take these walks around the block near our house every day with Bailey.

[00:40:03] Harley Finkelstein: She was born in June, so summertime in Canada. Very nice. We'd walk around and my wife would say, I wish there was an ice cream shop here. And that conversation sort of evolved into eventually her saying, I'm gonna start an ice cream shop. And she ended up building this great, amazing ice cream shop and, and brand called Sunday School.

[00:40:20] Harley Finkelstein: So, but from a personal perspective, a lot of the women in my life have also become entrepreneurs and have taken an idea or a problem and solved it through entrepreneurship. But I also think that there is far more resources today available to anyone that wants to start an entrepreneur, whether it's a woman or a man or anyone for that matter.

[00:40:38] Harley Finkelstein: That's the first thing. The second thing is, Entrepreneurship can be started from anywhere. And specifically around the time the pandemic where we were all we, we were all sheltering in a place, we're all at home. It became clear to people that they can actually translate their energy at home into building a real business.

[00:40:53] Harley Finkelstein: And I think that's why you sort of have this, you know, that's one of the reasons you see so many more people starting businesses because the pandemic gave us a lot of time at home to think about what do we want to do, what do we wanna create? How can I share my, my gifts with the world? But I think the bigger one is this.

[00:41:08] Harley Finkelstein: I think it has a lot to do with mentorship. And role modeling. Now that you are not, not only is more than half of the entrepreneurs on Shopify women, you see incredible like Hall, like you. You see all these incredible women, female entrepreneurs that are kicking ass right now, and you're like, wow, I think I can do that too.

[00:41:25] Harley Finkelstein: She kind of looks like me, or that person kind of reminds me of me, like you all of a sudden inherit this incredible audacity. And that audacity has allowed more people to participate who otherwise traditionally did not. Whereas in the past, if you think about entrepreneurs, close your eyes, think about entrepreneurs.

[00:41:42] Harley Finkelstein: You think about like Steve Jobs and you think about like people, like, you know, mark Zuckerberg. If, if you're in tech, for example, you think about mostly dudes, because historically those are the ones that were on the front cover of Forbes and Fortune, all these magazines as the world's greatest entrepreneurs.

[00:41:59] Harley Finkelstein: That's no longer the case anymore. Now you see people like Kylie Jenner, who, whether or not you agree that she's self-made or not, that's a different debate. She is now on the cover of Forbes as one of the youngest billionaires for creating a company, Kylie Cosmetics, on her own. And I think that is creating this incredible flywheel of more people, more momentum, more participation.

[00:42:21] Harley Finkelstein: And by the way, it's exactly the reason. What you point out is exactly the reason that I ended up joining the Board of Operation Hope. Because for me, one of the things that I had in my life, even though the entrepreneurs in my life, my grandparents, my parents, they were not successful, quote unquote entrepreneurs.

[00:42:34] Harley Finkelstein: They didn't make a lot of money. I knew enough people in my life that were entrepreneurs, that were small business owners, that it didn't feel foreign to me to actually try my hand at it. What I've realized through John Hope Bryant is the founder of Operation Hope is that that's not the case For more, most people, most people don't know entrepreneurs.

[00:42:51] Harley Finkelstein: They don't know anyone who owns their own business, and because of that, their likelihood to start is far less than it would be for someone who actually does know entrepreneurs. The idea that this program that we've created with Operation Hope called one 1 million Black Businesses, one M B B is by 2030 to create 1 million new black-owned businesses and help create.

[00:43:11] Harley Finkelstein: 1 million more black entrepreneurs. And part of it is that those 1 million entrepreneurs, they build great businesses, they're successful. But it also means that more people in those communities who traditionally don't have a lot of entrepreneurs, see people that look like them, that speak like them, that act like them, try their hand at this thing.

[00:43:27] Harley Finkelstein: And that's what we think will create this incredible flywheel of expanded our entrepreneurship. That's 

[00:43:32] Hala Taha: awesome. And where can people find out about Operation 

[00:43:34] Harley Finkelstein: Hope? If you just look up Operation Hope, just operation hope.com, you can see all about it. It is really amazing. And by the way, it's mentorship, it's education, it's money, it's assistance.

[00:43:45] Harley Finkelstein: If you need an accountant, we can introduce you to one. If you need to talk to someone to do product photography. We have a great list of resources, but it helps more people discover something that has been outta reach for a lot of people for a long time. And I'm here for it because I think. It's not for everyone, but for some people, like entrepreneurship is unequivocally the way they're gonna find their life's work.

[00:44:03] Harley Finkelstein: And I think once you find your life's work and you get a chance to work on it over a period of many decades, man, things get really, really fun. 

[00:44:10] Hala Taha: Yeah, I have to say I love my company and it is so much fun being an entrepreneur compared to working for somebody else, so I totally agree. Okay, one more follow up question.

[00:44:20] Hala Taha: So I'm, I know you mentioned the creator economy and the fact that a lot of people are sort of reverse engineering. They're pathed towards entrepreneurship. So it used to be you create a product, like you said, then you'd go out and try to find an audience. Now a lot of people have built in audiences. And they try to figure out what product that audience would want.

[00:44:36] Hala Taha: What are the benefits or the advantages of being a creator entrepreneur as opposed to starting with 

[00:44:41] Harley Finkelstein: the product first? I think there's something about momentum in business creation, and I think what, what is easier? It's not easy cuz business creation is not easy and frankly, entrepreneur is not easy.

[00:44:50] Harley Finkelstein: Like we're not changing physics here. Most businesses fail. The good news is that now if you fail at something, you can try something else and you're not gonna necessarily lose your house hopefully. But business momentum is a real thing. Here's the best example I can give you during the pandemic. My anxiety levels sort of skyrocketed.

[00:45:05] Harley Finkelstein: I was drinking way too much coffee. I was at home by myself working. So one of my best friends, David Siegel, said, Hey, let me actually get you to start drinking more tea. And I never drank tea before. And he's like, I'm gonna curate and sort of create this box of really high end, like the best green tea on the planet, and I'm gonna create product for you.

[00:45:21] Harley Finkelstein: Like I'm gonna make you a, a special Harley box of tea. And I fell in love with it. I like, I drink tea every afternoon. I drink coffee in the morning, tea in the afternoon. And so I began to tell people, Very slowly, very sel, very, uh, subtly, Hey, you know, I'm thinking about trying my handle. This little tea company.

[00:45:38] Harley Finkelstein: I'd post something on, on Instagram or Twitter or LinkedIn. I'd tell us a few friends and all of a sudden people started asking me weeks later, Hey, like, how's the tea company going? Are you still doing that thing? Is that's, I was like, yeah, it's, I'm working on, it's really cool. Like, I'm gonna start an, you know, my, my second shop, if I store my first one was 2006.

[00:45:53] Harley Finkelstein: My second will be 2020. I'm really excited. And then we launched and I remember when we launched, I had this list in my mind of like, I'm gonna send this the link to like 25 people who've been bugging me for, for all this time, asking when I'm launching. And those are my first 25 customers. And once I got that, I'm not sure all 25 bot, maybe it was like, 18 of them or 12 of them bought.

[00:46:15] Harley Finkelstein: But it just gave me this incredible confidence that, oh, may maybe amount to something now, maybe that was artificial, maybe that was just luck and maybe, but it gave me the drive to keep going to go from chapter one, which is launching to chapter two, which is, okay, now I gotta find a real scalable channel of which to find new customers.

[00:46:34] Harley Finkelstein: And that's what I think is so compelling and so fascinating about the creator, uh, creators turning into entrepreneurs. They have their 1000 true, true fans already, you know, built in. But it has to be authentic. The reason that there's a very famous story, uh, in the eighties of Brad Pitt doing a, uh, creating his own toothpaste, and it failed.

[00:46:54] Harley Finkelstein: Of course it failed because like nobody associates Brad Pitt. I mean, he's great at a lot of things. but no one associates him with having especially good dental hygiene. However, someone like Mr. Beast, who's well known for loving chocolate. Who has to eat a particular type of chocolate because he has certain health issues.

[00:47:10] Harley Finkelstein: Creating something like feast balls and allowing, inviting his audience in to participate in the journey of building it r and d samples, here's what we're gonna do, here's what we do next, and then releasing it. Obviously he is got a huge audience, but it, he turned his subscribers and his audience into consumers, into participants, into fans of what he was making now, Partly starting fire Belly.

[00:47:36] Harley Finkelstein: T versus Mr. Beast could not be more far apart. I mean, that is like, Those are different extremes, but in the middle, I think you have a lot of people who have these built-in audiences and they know what their audience really wants, and if there's something that their audience wants and they want, and they've had dialogue about this, but it doesn't yet exist, that is a perfect opportunity for them to create something brand new and then sell it or offer it to their audience.

[00:47:59] Harley Finkelstein: And maybe it just stays with our audience. Maybe you're, maybe you're only selling pens to the a hundred people in your subreddit pen group because you're in the subreddit pen group and you always talk about the best pens and you think you've created a better pen. And maybe your only, your entire, your total adjustable market is everyone in that subreddit.

[00:48:15] Harley Finkelstein: That's okay, but maybe that gets you going. Now you're making staplers, now you're making all types of, you know, Now you're making notepads and, and pens and paper, and I think that it just gives you a little bit of an early momentum start into entrepreneurship, and I think that's why it's really, really compelling.

[00:48:31] Harley Finkelstein: By the way, it's the reason why I think some of these celebrity brands, even some of 'em that get a bad rap, I don't believe all of them deserve a bad rap. I mean, I was very close to, to Jimmy Butler creating Big Face coffee. I remember like early days when he first contacted Shopify, he was making coffee in the N B A bubble for other basketball players cuz there was no good coffee there.

[00:48:51] Harley Finkelstein: And then decides after the N B A bubble opens up and people go back to their towns and he wants to create big face coffee brand. And then I remember hearing from someone at Shopify who worked, who works very close with him, that he's actually going on a, on a coffee tour to go find better beans and better ingredients and better product and better accessories for the coffee.

[00:49:10] Harley Finkelstein: And I realized that this is not a promotional product. This is not Brad Pitt's selling toothpaste. This is genuinely someone who cares so deeply about coffee, making a better version of coffee and coffee products, and selling to the people that also, like Jimmy. Maybe you only know Jimmy as a basketball player.

[00:49:26] Harley Finkelstein: But now there are people in this world who really only know him as a coffee entrepreneur, and I think that is so cool. 

[00:49:32] Hala Taha: I love the creator economy because I coach people all the time on how to start businesses, and a lot of people just don't have product market fit. That's what I see a lot.

[00:49:41] Hala Taha: They're putting out a product, nobody wants to buy it. They don't have product market fit. When you're a creator, you can pulse your audience. Survey them, get to know what they want. You can pay attention to what they're asking you. You can iterate as you want. You can like build it as you go. So there's a lot of advantages there.

[00:49:57] Hala Taha: So let's talk about another concept that you talk about. and that's connected consumer in the future of e-commerce. So I heard you on Bloomberg. Uh, you talked about the future of e-commerce, moving from D to C, direct to consumer to C to C.

[00:50:09] Hala Taha: Can you talk to us about that and why you think things are changing? 

[00:50:13] Harley Finkelstein: You remember how we talked earlier about that for a period of time there were consumers that were interacting with Wendy's, like the Wendy's, the fast food chain, almost like Wendy was a person. Mm-hmm. So something dramatic has changed and I, I don't think it's, it's obvious, but I do think it's profound.

[00:50:28] Harley Finkelstein: And what has changed is that every time we as a consumer buy a product, we're not just buying it. For consumption reasons. We're also voting with our wallet for that product to exist in the world. The reason that I wear Allbirds, I think they're great shoes, high quality, but I believe what Joey and Tim are doing with Allbirds to create a more sustainable sneaker is fundamentally amazing.

[00:50:49] Harley Finkelstein: And I want to vote with my money, with my wallet for more of that to exist, whether it's Allbirds or it's other brands like Allbirds. The reason I wear James Purse is because I think there's no one who thinks more about black T-shirts than this guy and his team. I love people that are craft people that think so deeply about a particular thing.

[00:51:06] Harley Finkelstein: And so every time I buy out James per t-shirt, which is quite expensive, it feels like I'm endorsing this idea. And so I think today consumers have a very different relationship with the products, the brands, the companies that they buy from far beyond anything we've seen in the past. It actually reminds me of what we used to see 150 years ago where you as the consumer went to the bakery and bought the bread from the baker and you knew the baker's name and you knew their family and you knew what their birthday and or you went to the cobbler to have your shoes fixed and you knew the cobbler's, the cobbler's family.

[00:51:38] Harley Finkelstein: You knew the cobbler's life story. That sort of town square model made commerce and retail very, very personal, very intimate in a really wonderful way. And then frankly, for the last 150 years or so, we had these big department stores, which felt a little bit transactional. Whereas today I think we're coming back to a more personal, intimate, authentic buying experience between consumer and brand or consumer and maker.

[00:52:04] Harley Finkelstein: And for that reason, I think the brands that you and I love so much, it's not just the product that we're buying. We're buying a participation in that community. I mean, it's kind of an amazing thing, but like you buy a pair of sneakers on. Kit, for example, or on Noble, for example, and now you're kind of part of the kit community, now you're following them on Instagram as well.

[00:52:25] Harley Finkelstein: You're gonna, their pop-up events, if they have, you know, some sort of, uh, early release, midnight on a Sunday night, you're, you're staying up late and you're on, you're on the chats and you're on. Social media and you're talking to other people that are waiting for the drop to come. I mean, the Supreme community is a perfect example of that.

[00:52:40] Harley Finkelstein: Every Thursday at 11:00 AM this massive supreme flash sale happens. You're not just buying something from Su, from Supreme. You're participating in the Supreme community in a way that is just unlike anything we've seen in, you know, a hundred for the last a hundred years or so. And so I think the brands that do really well have a deep understanding of that connection, and they connect right to the consumer through multiple touchpoints in store, online, on social media, at farmer's markets, through media, through concerts.

[00:53:08] Harley Finkelstein: I mean brands that are now putting out incre, making these mix tapes effectively on Spotify. I mean, that is like not only do I love Superman, I love their skateboards, and I wear their hoodies, but I'm listening to their playlists, and then I can go on. A community forum. I can go on their Discord channel and I can talk to other people like that, that is connect to consumer.

[00:53:26] Harley Finkelstein: And that, by the way, is a much more interesting and exciting way for retail to operate. And I, I'm here for it. I love it. 

[00:53:32] Hala Taha: That's awesome. Okay. My last question to you is 2023, you call it the year of the entrepreneur. We're approaching a recession. A lot of people you know would assume it's not a good time to start a business, but you say otherwise.

[00:53:44] Hala Taha: Tell us why and your top advice for people starting businesses in 2023. 

[00:53:49] Harley Finkelstein: I think I, I've gone through a couple things that are just, I have to say and I'll, I'll say it again. One is the cost of failure being so low. You can try something today. If it doesn't work, it doesn't matter. Yeah, you may lose $39, but like, think about the impact you might have, like what may be the case if that actually is successful.

[00:54:04] Harley Finkelstein: Cause that's the first thing. The second thing is when I started my t-shirt business store 139 on Shopify in 2006, the main ingredient for me to be successful was I needed a lot of money because I needed to buy ads on AdWords. On Google, and the more money that I made, the more money I spent on AdWords, the more money I made.

[00:54:21] Harley Finkelstein: It was just sort of this, this virtual cycle, back and forth. Today, having more money is not necessarily going to lead to any success whatsoever. What is going to lead to more success is how good your product, how do you connect with your consumers? What kind of community have you built? What kind of content are you creating?

[00:54:36] Harley Finkelstein: That means that more people can participate and can start businesses, but it also means more people can build huge companies with few resources by simply being resourceful. So creativity over capital and resourcefulness over resources. That to me, is an incredibly compelling, and then I'll go one step further, which is that today, if you look at all the surface areas, digital surface areas or physical surface areas where consumers are spending their time from TikTok to Pinterest, from Spotify to YouTube, All of these are these wonderful opportunities to engage, to have conversations.

[00:55:10] Harley Finkelstein: I mean, if I was starting Fire Belly today versus two years ago, I would probably spend a lot more of my time. I know YouTube comments are kind of a weird place sometimes, but I would find some great videos on YouTube where people are talking about getting really geeky and really nerd, like nerding out on tea, and I would participate in those conversations and eventually after.

[00:55:31] Harley Finkelstein: Creating value for that community, I may say, Hey, you should check out what I'm doing with Fyre, be e t. I think it's really compelling. So that is a very different way to build a business. As an aside, I, I started a little personal project, sort of my weekend project for the last couple, the last couple of months has been this podcast called Big Shot.

[00:55:47] Harley Finkelstein: And Big Shot is an archival of some of the greatest Jewish entrepreneurs that have lived in the last a hundred years. And I'm trying to archive these stories before it's too late, before the people aren't around. When you hear these people that have built these crazy companies like Izzy Sharp building Four Seasons, or Aldo bed creating Aldo shoes, you realize that starting a business in the forties and fifties and sixties and frankly even the seventies was really, really tough.

[00:56:12] Harley Finkelstein: I mean, it was a blood bath, and if you didn't, if you didn't succeed, you lost everything. And the only way for you to really build was to bring on partners and raise money in capital. That's not the case anymore. Some of my most favorite stores on Shopify started at their mom's kitchen table. They're totally bootstrapped.

[00:56:28] Harley Finkelstein: They haven't raised any money. They're a one or two person operation and they're taking a, you know, I mean, look at Veri or Aloe Yoga or Gym Shark. Think about how competitive they are to, to Nike, and some of these companies are like five years old. I mean, this is an unbelievable time to start a business and it's because it's easier to start and it's easier to scale, and this is where the advantage goes.

[00:56:49] Harley Finkelstein: To the entrepreneur because if you deeply care about what you are building and providing in terms of value, service, product to the consumer, you're gonna win because it's, it's a lot easier for you to be authentic and for you to be the, like, for you to actually get in front of, of, of potential consumers versus a big company with a big brand.

[00:57:06] Harley Finkelstein: Yeah, 

[00:57:07] Hala Taha: I'm fired up guys. If you don't consider this your sign, I don't know what you're waiting for. Start your small business. Start your small company. If you guys wanna get a $1 per month trial, you can go to shopify.com/profiting, all lowercase Harley, it was such a pleasure. The last question I ask all my guests, two last questions.

[00:57:25] Hala Taha: We do something fun at the end of the year. What is one actionable thing are young and profits can do today to become more profitable tomorrow? 

[00:57:33] Harley Finkelstein: The first thing I would say is try your hand at a couple different things, like this idea of throwing spaghetti at the wall and seeing what sticks. It's not just a, a fun thing to say, like try a bunch of different things.

[00:57:42] Harley Finkelstein: Even if you have a business that, like, I don't know if I'll, if fire belly ever becomes a big company or not, but like at some point I'm gonna try my head at coffee cuz I, I've done the tea thing really well. Maybe we expand to coffee. Do I need to? No, but like who knows? Maybe it's gonna work and if it doesn't work, I can stick to T.

[00:57:57] Harley Finkelstein: And if it does work, now I have two product lines. Try stuff like the fact that you can do so right now with limited risk and you can discover things that don't work as the new definition of failure. Just go ahead and do it. And by the way, if you don't know what to start, you're not really sure what to sell, look at the stuff you're using.

[00:58:13] Harley Finkelstein: Look at your desk right now. Like I got lots of notepads and I got lots of pens here and coffee mugs and stuff. If I were to start something, like I'd look around and be like, I need, like I. Why a post that's not like they're just flimsy. I, I want a better version of a post. I'm gonna go and try to tinker in my garage in my little workshop at home, and I'm gonna try to make a better version of that.

[00:58:31] Harley Finkelstein: But find the stuff that you're already using or the things you're already making and think about would other people wanna consume that as well. Hmm. That's 

[00:58:39] Hala Taha: great advice. And my last question is, what is your secret to profiting in life? And this can be outside of profiting financially. 

[00:58:45] Harley Finkelstein: I think the most important decision any of us make is our spouse or our our life partner, wife, husband, boyfriend, girlfriend, whatever you wanna call that person.

[00:58:53] Harley Finkelstein: A lot of people spend more time contemplating what car they're gonna drive or what kind of sneakers they wanna buy. And not enough time thinking about choosing the right life partner. And I'm fortunate that I have, I think, the greatest life partner for me, uh, in Lindsay, who's my wife, because there's no way I can live at this level of, of energy, of excitement, of just get shit done without having this incredible foundation that is, that is Lindsay.

[00:59:16] Harley Finkelstein: And I would encourage all of you to think deeply about that if you have someone cherish that person, because that's kind of the secret to this whole thing. 

[00:59:23] Hala Taha: That's so funny. People have been mentioning that on my podcast way more frequently. There's always like themes that pop up every year and relationships and picking the right spouse is definitely a theme 

[00:59:33] Harley Finkelstein: it matters. Lindsay and I have been i'll, I'll just, I'll get a little vulnerable for a second before we close. Lindsay and I have been seeing a, we have been seeing a couples therapist since we got married. Like just like you. You go to the gym before you need to go to the gym. Like we've been seeing a couples therapists biweekly for nine years or so, because we really believe that if that centerpiece of our life, which is our marriage, our relationship is not strong and sturdy and durable, nothing else matters.

[00:59:56] Harley Finkelstein: You need to have a foundation of strength to do all this other stuff, whether by the way you're an employee and a founder and entrepreneur, you're a doctor, lawyer, you're. Whatever, you're an artist. Whatever you do, you need to have that strong foundation and, and the more I talk to people about that, the more I realize that most people have not contemplated how important that particular person is in your life.

[01:00:15] Harley Finkelstein: Well, thank 

[01:00:15] Hala Taha: you so much, Harley. This has been such a great conversation. Where can everybody learn more about you and everything that you do? 

[01:00:20] Harley Finkelstein: Uh, Harley at Harley F on Twitter, at Harley on Instagram, and of course, check out shopify.com if I can be helpful to anyone, anyone who's listening that is starting a business now, I can't promise you, I can give you that much time, but please, please send me a tweet at Harley f or an Instagram dm.

[01:00:35] Harley Finkelstein: And I would love to be your first customer. So if you launch something on Shopify, let me be your first customer to send me a, a tweet or a dm, and I'd love to do that for you. What a great 

[01:00:44] Hala Taha: way to close. Thank you so much, Harley, for your time. 

[01:00:47] Harley Finkelstein: Thank you so much for having me.

[01:00:47] Hala Taha: Man, what an amazing episode. Harley was so great to talk to you. I learned so much and I love how passionate he is about Shopify and entrepreneurship, and I totally agree with him. We're in this entrepreneurial renaissance right now. We have access to more resources than ever before to start and grow a business.

[01:01:11] Hala Taha: You should feel really good about this because all you need is an idea and a lot of ambition. You don't need to be rich. You don't need to spend a ton of money on ads and platforms like Shopify have made it super easy for the everyday person to become an entrepreneur or start their side business. I think my biggest takeaway from this conversation is that creators are the next generation of entrepreneurs building brands.

[01:01:34] Hala Taha: Creators have reverse engineered the way that brands are built. Before you built a product and then you went and found an audience. Today, creators build an audience first and then go build a product based on what they know their audience loves. And I love this because when you're a creator, first you can figure out what your customers want, what they want from you specifically and what problems you can solve for them.

[01:01:56] Hala Taha: And then you have built in product market fit, which is one of the biggest challenges when it comes to running a business, actually making sure that there's ample demand for your products and services. And the best part is, taking this approach is basically free. All you need is your phone, a computer, a niche to go after, and your editing softwares of choice.

[01:02:14] Hala Taha: And remember, your audience is your choice too. We had Alex Hormozi on, who's a very successful entrepreneur and marketer, and he told me that you should try to solve rich people's problems because they have the most money. And I say, if you're taking a creator first approach, then try to attract rich people to your online community so then they have money to buy from you down the line.

[01:02:35] Hala Taha: And remember, you don't need to be some huge famous creator in order to start monetizing. The creator economy is estimated to be worth a hundred billion dollars. And yet only 4 percent of creators do it full time. There's plenty of pie to go around, and small creators are all the rage right now when it comes to marketers.

[01:02:51] Hala Taha: If you want to start your side hustle or business, I recommend that you try out Shopify. Don't start something from scratch. Focus on your product. Focus on your marketing. Let Shopify do that hard back end work for you. You can sign up for a 1 per month trial period at shopify. com slash profiting, and that's all lowercase.

[01:03:10] Hala Taha: Again, that's shopify. com slash profiting for a 1 per month trial period. And I want to hear about your businesses. If you start one or want to start one, shoot me a DM on Instagram at yapwithhala. I want to hear all about it. Thank you so much for listening to young and profiting podcast. If you listen, learned and profited, share this episode with your friends and family and do take a minute to drop us a five star review on Apple podcasts.

[01:03:34] Hala Taha: It's the number one way to thank us. If you'd like to watch your podcast, you can check us out on YouTube. All of our videos are uploaded there. You can also find me on Instagram at Yap with Hala or LinkedIn by searching my name, it's Hala Taha. I want to shout out my talented Yap production team as always.

[01:03:49] Hala Taha: You guys are awesome. This is your host, Hala Taha, signing off.


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