The Formula Rhode & Skims Use To Win (and how you can do it too!) Shopify President
1h 18m 32s
Entrepreneurship is not about fame or following a celebrity model, but about solving real personal problems. The transcript emphasizes that successful businesses often begin with small, authentic ideas—like a T-shirt business or homemade pancakes—rooted in lived experience. Today’s low barriers to entry, powered by tools like Shopify, mean anyone can start a business affordably and scale with minimal risk. Grit, resilience, and the ability to keep going through rejection are more critical than initial success or followers. The key insight is that most top-performing brands didn’t have grand visions—they solved problems they personally faced. Authenticity and deep community connection matter far more than follower counts, as loyalty breeds long-term growth. Emerging technologies like AI and agentic shopping are democratizing commerce, enabling personalized, merit-based shopping experiences that help small brands get found. These tools don’t replace human influence but expand opportunities for discovery. Ultimately, the path to entrepreneurship lies in self-awareness: identifying your passion, purpose, and value, and building a business that aligns with your life’s work. Whether it’s through a startup or a side project, the journey begins with a simple, personal idea—and the courage to act on it.
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Haley and the team at Rode, Allo, Gymshark, none of them thought 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 emotional here. 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 years ago.
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.
And thank you.
In case you missed it, you're allowed to be hot, smart, and rich. So let's get into it.
Carly Finkelstein, 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 there was something about
my journey where I was like, I'm going to do this. I'm going to do this. I'm
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 is 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 Le Capitaine. He came to entrepreneurship
through the lens of what I call now forced entrepreneurship. He had no choice.
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 or self-identify as
an entrepreneur because in your mind, you had some other vision of like 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 of 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 you're doing, is that you're doing a lot of work. And I think you're doing a
lot of work. And we'll get to AI later on. But I think two things have changed since my
grandfather started that ag 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 barrier to 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. I 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, owner of Lemonade Stand. He made
these ideas throughout my life real for me by literally creating like the physical manifestation
of my idea in a business card form. So I'm 13 years old, 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,
bat mitzvah, wedding, birthday party, neighborhood barbecue in my area, my community in Montreal in
Canada, I was involved. 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, this mind blowing experience that like I was able to turn a problem. I want to be a
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, they don't really know what their path might be, they don't really know what
to them 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 your question. No,
I do not think everyone should be an entrepreneur. But I do think more people should try to 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 US ecommerce. 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 G.A.
in the My Sales volume,
almost all of them
If I would have asked them when they were 20 years old, if entrepreneurship or 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 Viore and Fashion Nova and Gymshark 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.
And when I was in college at McGill, my dad wasn't around anymore.
I had to support my mom and I have two much younger sisters.
So I started selling T-shirts to universities across Canada.
It's not a great business, but it 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.
At that coffee shop, I would end up meeting Toby, who 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 are 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, in 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 at a WeWork, whatever you want to do.
But spend time with people that are on a similar journey, maybe at different steps of the journey, but a similar journey.
That's first.
The second thing is, okay, I 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 hundred stores on Shopify.
The business they created.
Solved their own problem.
Trina at Figs 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 Gymshark 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 up, go down all of those different brands, same thing with Danny and Aloe, 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 and 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 out 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, I make beautiful.
Blankets, but I really just make it for my nieces and nephews.
Like no one's going to want that.
And it's bullshit.
And that's self 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, 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.
It didn't have your success.
And, 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,
you're literally one of the first merchants ever on Shopify.
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 no's, 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, the egg that he didn't care about eggs.
He cared about his family.
He cared about philanthropy, 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 am 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 like the term icky guy.
Which is, okay, wow.
Prepared for you.
Wow.
I was really excited about this.
So icky guy, so can you actually articulate the exact?
Don't look at my questions, Harlan.
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 not 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 consigliere.
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, 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.
We started as a tiny little company in Ottawa, Canada, four people.
Now we're 8,000 people were publicly traded.
We have a very large market cap, you know, over a hundred billion dollars of market cap.
Now I have to be good at being a public company leader.
I have to get good at storytelling.
I have to get good at like culture.
I think a 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 that I get to try all these new things.
If for me, it's a little bit of a personal growth journey disguised as 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 shop plays about 22 years old.
I've been there for almost two decades, every, 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 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 want me to move ahead?
Completely.
I am going to be very honest and 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.
Cause 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 hot, smart, rich.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 a hundred billion dollars.
It's like 155.48 billion today.
Yeah.
And that's why I'm so proud of you.
can do in the workplace. It's not just a podcast recording. It's a statement. And I just, 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 and
what Shopify 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 with Barry Diller.
Barry Diller created IAC. He was at 32 years old. He was the chairman of Paramount.
IAC obviously owns Expedia and 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 Shopify. I did not know that,
Meg, I swear. 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. I tried a business, it 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
if you 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 first sales. At least one of those will likely be a million dollar company
at some point.
Hiring now? 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 Bryan. 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 you surround yourself with people that you want to emulate.
And. I still. 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 me because he
didn't want to meet with me. I just kept going. I was polite. I didn't 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. I'm 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 use, but there's a give a shit
quotient. There's EQ, IQ, give a shit. 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 about 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 be.
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So Katie pulled in a hand-vetted freelancer from Fiverr Pro, who delivered to such a high standard
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It's so true what you said, surrounding 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 you.
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 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. Know 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 in 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 some, 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 of 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 this 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 Renfri in my head. Put that one line in the subject.
And that's it. I'll tell you an interesting story. I don't share, I haven't shared this in a long time.
Years ago, like 2011 or 2012, we were, we had this thing called the Shopify 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 a hundred thousand dollars. That was 2010. Turned out
that like the winner of these competitions, we're making, we're building a billion dollar
companies. A hundred grand wasn't 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 to get involved and Seth Godin. And, but I really
wanted Gary Vaynerchuk at the time he was like peaking. It was like Pete Gary, right? And he was,
I wasn't getting his attention. And he just put out a book at that point called crush it. I think
it was called crushes 2011 or so. And there was this website that I don't think it's still available.
It's called one 800 CEO reads.com. And it showed you how far every book was from hitting the New
York times bestseller list. And it showed the number of how many books is left. It was like
a sliding scale. So I knew the crush. It was 3,872 books away from hitting the bestseller list.
And I ended up emailing Gary with a subject line. I want to buy 3,872 books. And that was
something like, I don't think there was any body. There was no written body in the email. And of
course, he just put out a book, knows exactly how far they are from that. And he responded and we
ended up having him and he, he was a mentor for the build a business conscious 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 3000 books at that point from him over, over the years. But I knew that if I
would have created this beautifully crafted articulate pitch about the 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 meet, one, they're probably not going
for the first five or 10 messages, but second, you have to like, you know, I'm in LA now doing,
doing your show. And I knew I was here. So 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 LA 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. 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-umnus. 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 most
remarkable about Mr. Beast, and most people don't know, is he effectively has like, it's kind of
like these boxes. He's got 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 peaking 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 that box. And
you're like, well, he's peaking. You're like, 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 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 good at it, they're going to
really thoughtful, they find a new box. For Mr. Beast, for example, like the Feastable stuff is
really incredible. He just bought a fintech company, a bank, a new bank. 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 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 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 have. I
require and underestimate the idea of a thousand true fans. 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 are 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 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 all these incredible, going back to Ben Francis' Gymshark, you hear how big Gymshark
is now. And Ben literally started just by sending Gymshark 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 has kind of been owned by Gymshark
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, in some cases, single million dollar companies, just selling something to someone who
really values it. And I had this thing I started in the pandemic called Firebelly Tea. I started
with my best friend, David Siegel.
So David's Tea and Shopify, 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. Because like his, 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 Sencha Tea 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 every one of the first customers of Firebelly, asked them what they thought,
tried to figure out a way to make it better. And Firebelly,
he's 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. Beast. You just have to
over deliver to those 1000 true fans, you know, direct to consumer as a business model. It seems
like it seems like a nothing. Well, yeah, 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, you know, you're not going to be able to do that. You're not going to be able to do that.
You're not going to
beg a retail buyer to put their products on the shelf anymore. Anyone can now just do it on 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
traditional celebrity Hollywood brands and like the creator brands, the brands 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 always was built historically since the beginning of,
like, commerce and retail. So thousands of years, the sequence was build the product first and then
build an audience or find 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, we're posting on social media,
people that are making videos, people 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
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, like they know the OVO audience. They know the
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 Chamberlain Coffee would never
work. Jimmy created Feastables because he himself wanted a particular brand. And he wanted a
particular type of chocolate. 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. Like Skims was made
because they wanted to do shapewear in a particular way. And they didn't like, they were spanks. And
therefore they created Skims and it worked really well. There's this amazing teenager named 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,
loves 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. And she's like,
tell me what you think. Hey, I'm going to try this other thing. 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 she allowed people to follow 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 in the history of
commerce that you've seen this flip from product first audience second and and 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's 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 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 k 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
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sponsored jobs 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 name from kimono 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 i love i love saunas like i just i'm high energy and high
anxiety so i love saunas you know jesse itzler 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 29 0 29 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 and i was like i need a sauna hat
the first person i thought about when i thought of a sauna was i went to jesse's profile on
instagram and i was like what is because i was even sauna hat i was like what is he 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 type of brand that will have longevity because it was
for him and his community in a very authentic way and i also think about on the athlete 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 sense of the brand and he couldn't make sense of the brand
he needed distribution and nike has distribution and i think what's so cool right now is
distribution has been democratized so now when you see these athlete brands we did this thing
with luca donchik here in la 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
uh it was like a trick shot you get a discount on all the products
it's amazing
it was really really neat but it was so amazing because like luca has a huge following he's 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 badly or 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
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 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 the how fast things are changing
a week ago i installed open claw on my phone on my on telegram and i've been playing with it it's
really cool it's 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've been playing with it for a long time and i've been
playing with it for a long time and i've been playing with it for a long time and i've been
able to and it's it runs 24 7 you know when i shut down like if you use chat gbt close your
computer it stops running open clause is 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 the things i was
frustrated about a week ago i've all been fixed i mean think about that in in less than a week
like this thing has gotten materially better i'll give you another example i went out for dinner a
in 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 this huge company and he asked what who's
my best customer gave it right away i said great now ask a sidekick what should i sell next to this
customer and he did it right away it's like this customer has bought these things therefore we
think these skews should be sold to that particular customer she is most likely to buy these skews
two things happened one i mean 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 in fact it's a great way to democratize leverage and in fact it's a great way to democratize
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 or 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
that a big company can, but now you have Sidekiq.
Now you have these tools.
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 ChatGPT 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 at 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 LA, it's not on commission. It's merit-based. This idea of agentic shopping also
means that you're not going to be able to buy a lot of stuff. You're going to be able to buy a lot
of stuff. You're going to be found even if you're a smaller business, because
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 next couple of months
called agentic. And I think from a consumer perspective, it's going to make shopping very
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 the online store. One spoke is if you have an offline store. One spoke may be
a pop-up. Maybe you also sell on, you know, you have a wholesale business, you sell in other
places. And then you have the agentic, which effectively allows consumers to buy directly on
all these amazing new tools. And I think 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
to describe it 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?
There's always going to be a place for that. Back to the agentic side, if the chat knows that
you, you know, you follow, what's a good example?
Paige Lorenz.
Yeah, Paige Lorenz, who has an amazing store.
Love her.
Yeah. If the chat application knows that you think Paige 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 show up and think
about how important that is. And I think that's going to be a place for that.
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 walked into a store and the store
clerk says, we think like you should buy this. And you're like, what is this? 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 sell on any
of those areas. The Roblox channel in particular, when it came out, I talked about it and a bunch of
people had asked me, I think we 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 Fenty's, you know, incredible Sapna who runs Fenty Beauty, to her credit, she's like,
you know what? I'm going to get this thing a try. And Sapna and her team and Fenty built this
Fenty store inside of Roblox. And we power the checkout and all that for her. We power the checkout
and we make it really easy. It's an amazing new channel for her and for Fenty. So do most brands,
should they sell on 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 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 in our
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. So 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 HotSmartRich
because this is the first time I've been on a show where I've been on a show where I've been on a show
where I've been on a show where I've been on a show where I've been on a show where I've been on a
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
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So head to joinbuilt.com slash HSR to sign up and start getting rewarded on one of life's
biggest expenses. That's joinbuilt.com slash HSR. Make sure you use our URL so that they know we
sent you. Hiring now? 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.
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, hundred million dollar,
million dollar, whatever they choose to build businesses in the future?
So one daughter here clearly wants to start dance class for toddlers.
The other one wants to do a lemonade stand.
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.
My dad 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. It was
almost ignorant for him to say that. He didn't know. My father doesn't know anything about DJing.
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 immediate thing I think about because this is where my head goes is like
well what's your 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 law 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 it the swagger the 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 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
you
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 you know I do that with like with
Lindsay too Lindsay decided after she had she gave birth to a baby and she was like I'm going to
be an ice cream 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 in the right way
really really matters and um I love this this is amazing
wow Harley I have to do some rapid fire last thing you put on your credit card
well it's a soul cycle this morning so probably soul cycle yeah I love yeah yeah okay last most
expensive thing I love 11t do you know 11t no great brand I just bought a jacket a bomber jacket
from them okay uh 11t I it's spelled 11t ty but uh amazing brand shopify brand shopify brand that's
not a picture shop but yeah I bought a jacket from them I love them I love them I love them I love them
they're amazing I wear James purse basically every day okay I think James purse is incredible
what else I like I like watches um but I haven't bought a watch in a while okay
um but I want to give you a fun one um do you tie expensive purchases like a watch to
accomplishments milestones usually yeah yeah when something really special in my life happens
because I find it's it's a nice reminder I bought this watch at the IPO to Daytona and
every time I look at it reminds me of that you know you and I are both skiers I just bought
I bought a helmet uh a pock helmet with bluetooth built in and I really love that send me the link
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 that's awesome speaking of skiing
or building businesses oh both I don't think again you have to there's now and it's an off
at fire building businesses it's just that's that is my it's my greatest joy in the world is
is is building is there a brand out there that doesn't use shopify
that you want to before the end of 2026 Brunello Cuccinelli
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 support ad 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 Horowitz is incredible as well yeah actually you know I'll give you a controversial one maybe
not controversial but a really important one it's called anti-fragile the Simtel ape 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 uh it's 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 of 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 be more resilient and the anti-fragile book itself anti-fragility
does a really good job of embedding that into your psyche beyond that 1000 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
where huge food is sold and I love restaurants where huge food is sold and I love restaurants
I love foodies I don't I know nothing about it and in fact I can see myself wanting to get into
the restaurant business because we love restaurants we love my wife and I love dining it's like our
it's our favorite thing in the world to go to a great restaurant in 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 costs 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 are rather are based on like I'm like let's expand because I want more people here and they're
like no I'm not going to do that I'm going to do it I'm going to do it I'm going to do it
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 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 the 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 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 now 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 picking 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 schlump like I can do this better so I think that's incredibly
innovative I think yes there's some brands on 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 um the team Mattel and
and everyone everyone there and Mattel was created in 1945 somehow like they keep innovating like for
me I don't get the Barbie movie I just Mattel creations they do drops I was driving here today
I drove by the Supreme store 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 Purse store
you can hide all the logos you can hide the name you smell it you're like James Purse star 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 God and I pray at the altar of God and 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's
it doesn't have to be fancy I like these bracelets from M. Cohen because like he cares about
bracelets I know the Bombas the Bombas socks guys for a long time like 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 experience this every single day do you know Takovas yeah the
yeah so like I spent a lot of time with Kevin team Takovas 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 Takovas store in New York City or in San Diego or in
Austin or anywhere LA or wherever the stores are you walk in you're like this is Takovas there's
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 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 personalized
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 a Starbucks is closer they still go there because
they know the person there just they the size 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 Shopify 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 engineering.
And I thought that's what I have to be.
And it was only a couple of years ago that,
and 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
and 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 points.
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 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 Harley 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 cases 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?
And these are people like Linda Resnick,
who created Fiji Water,
or Izzy Sharp, who created The Four Seasons,
or Vicky Drexler, who basically created The Gap
and founder of the Old Navy.
Like really iconic people.
And I just say, when did 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 The 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 Bailey 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 era where, you know,
my spiky point era, spiky object era,
where I like, I want to grow.
I'm not the best storyteller.
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?
And 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 think I would be,
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 like, 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.
If 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 memento.
You get the video afterwards.
Maybe it's on YouTube.
Maybe it's they sent you a file
on Dropbox, 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 like, ask your mom
to come and record that
and then watch that video.
You know, every amazing athlete
that I've met who like is
like superstar athletes
all tell me they watch their tapes.
They re-watch their tapes.
We've been public now for 11 years,
so I've done 44,
not only do 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
was I repeat myself now.
Q4 2025's revenue
was more than all of 2020.
I heard that stat.
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'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
or 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 small or as large as they are,
that is an incredible hack
to just a true self-improvement.
Harley, I really meant what I said
at the beginning of this interview.
Like I have a big,
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,
outside 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
any time you invite me.
You know, Instagram,
I'm just at Harley.
I'm lucky I have one 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.show.
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.
Like,
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 so much for coming on.
Thank you so much.
Y'all know I love a mood board.
So everything that relates
to the creative,
the name, the brand,
the website, the vision board.
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for founders who want to launch
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Podcast Summary
Key Points:
Entrepreneurship is rooted in solving personal problems, not status, and many successful founders started with small, authentic ideas like pancake batter or T-shirt sales.
The barrier to entry in starting a business is lower than ever, thanks to affordable tools like Shopify, making it possible for anyone to launch a business with minimal upfront cost.
Success often stems from grit, resilience, and persistence—many founders face rejections, but those who keep going eventually build something impactful.
The best business ideas arise from personal experiences and genuine needs, not grand visions; most top brands on Shopify solved problems they personally faced.
Authenticity and deep customer connection are more valuable than follower counts—loyal, engaged communities can grow a business without massive hype.
AI and agentic shopping are democratizing commerce, empowering small businesses to compete by offering personalized, context-aware shopping experiences.
Surrounding yourself with entrepreneurs fosters growth and inspiration, as proximity to similar journeys fuels motivation and innovation.
Founders should start by identifying their "life’s work"—a mission where passion, purpose, and profit align—rather than chasing trends or external validation.
Summary:
Entrepreneurship is not about fame or following a celebrity model, but about solving real personal problems. The transcript emphasizes that successful businesses often begin with small, authentic ideas—like a T-shirt business or homemade pancakes—rooted in lived experience. Today’s low barriers to entry, powered by tools like Shopify, mean anyone can start a business affordably and scale with minimal risk.
Grit, resilience, and the ability to keep going through rejection are more critical than initial success or followers. The key insight is that most top-performing brands didn’t have grand visions—they solved problems they personally faced. Authenticity and deep community connection matter far more than follower counts, as loyalty breeds long-term growth.
Emerging technologies like AI and agentic shopping are democratizing commerce, enabling personalized, merit-based shopping experiences that help small brands get found. These tools don’t replace human influence but expand opportunities for discovery. Ultimately, the path to entrepreneurship lies in self-awareness: identifying your passion, purpose, and value, and building a business that aligns with your life’s work.
Whether it’s through a startup or a side project, the journey begins with a simple, personal idea—and the courage to act on it.
FAQs
The key is grit and resilience—maintaining energy after rejection or failure. Many successful entrepreneurs, including Shopify's founder, faced multiple rejections before success, proving that persistence is more important than initial success or popularity.
Yes. The barrier to entry is extremely low; for example, starting a business for $39 a month on platforms like Shopify makes it possible for anyone to begin, with unlimited potential to scale and grow.
It means you don’t need a large audience to succeed—just 1,000 loyal customers who deeply value your product. This loyal community creates a flywheel effect, driving growth through word-of-mouth and repeat purchases.
Look at a personal problem or need you've experienced—like making pancakes or organizing a community event—and build a solution around it. Most successful businesses start by solving a personal problem.
Being around other entrepreneurs fosters inspiration, accountability, and learning. It’s a proven way to develop grit, gain new perspectives, and increase your chances of success through proximity and shared experience.
AI is an opportunity. It democratizes access to tools and insights, allowing small businesses to compete with larger ones by providing real-time, personalized advice and customer insights.
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