August 25, 2020 • 47 mins
Harley Finkelstein is an entrepreneur, lawyer, and the Chief Operating Officer of Shopify.
He founded his first company at age 17 while a student at McGill. Harley completed his law degree and 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 recently received the Canadian Angel Investor of the Year Award, Canada's Top 40 Under 40 Award, and was inducted into the Order of Ottawa.
From 2014 to 2017, Harley was on the Board of the C100; from 2017 to 2020, he was on to the Board of Directors of the Canadian Broadcasting Corporation (CBC).
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Episode Transcript
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Speaker 1 (00:01):
Art of the Hustle is a production of I Heart Radio.
You're listening to the Art of the Hustle, the show
that breaks down how some of the world's most fascinating
people have hustled and learned their way into achieving great things.
(00:21):
I'm your host Jeff Rosenthal, co founder of Summit, and
on today's episode, I had the pleasure to interview my
friend Harley Finkelstein, CEO of Shopify, Canadian entrepreneur and just
all around great guy. We discussed his amazing journey from
two thousand eight joining a small startup at Shopify, and
then growing it to a publicly traded company with over
(00:41):
six thousand employees, a hundred and thirty billion dollar market cap,
and over one million entrepreneurs operating stores on their platform.
I was pretty blown away to learn how Shopify has
maintained its culture over the last fourteen years, it's innovative
and experimental edge even as they've achieved massive success, and
(01:01):
how they've always seemed to be way ahead of the
curve when it comes to channel partnerships, technology and new
resources for its user base. And just simply get to
know Harley better, who is honestly a role model for
me and how he carries himself and how he approaches
his work. So please enjoy my conversation with Harley Finkelstein.
Thank you so much. I really appreciate it. I know
(01:23):
that you're you must be you know, slam the the
moment that we're in with with the pandemic and COVID
and just you know, I was reading some of the
stuff you've been, you know, saying in public recently and
the interviews have been doing just on the decade that
we jumped in terms of you know, bringing twenty I
imagine that you know, has a direct impact on the
(01:44):
amount of work that you have on a daily basis. Yeah,
you think about e commerce, So did like online commerce
as a percentage of total commerce went from someone like
five percent in two thousand eight until like eighteen, So
it took about ten years to get there. And we
basically have gone from fifteen percent uh to about twenty
(02:04):
five in the last ten or twelve weeks. So we've
seen effectively a decade worth of conversion to digital commerce
and retail um in the last you know, three three
four months, and it's it's been dramatic and frankly, what
we see is a sort of a tale of two worlds.
And you can use this lens for not just retail,
but you can use it for entrepreneurship or business in general.
(02:24):
You see a resiliency on one side, and you see
a reluctancy or or a resistance on the other side.
Some retailers and businesses have been resistant to change, and
they have floundered, and they have they've they've suffered some
really tough times, and others have just become incredibly resilient
and have changed their business for the better indefinitely. Yeah,
this is one of the things that Simon Sinek was
(02:45):
actually talking about on the podcast. Those that survive are
the ones that can pivot their way out of It's
just an incredible moment in time. And you know, we've
been friends now for I guess close to a decade.
We started Shop A five two eight. Correct. The story
of company actually goes back even further. It goes back
to around two thousand five or so. Actually two thousand four.
Toby had moved from Germany to Canada for the best
(03:08):
reason possible because he met a girl who's now his wife.
Came to Canada's new immigrant didn't wasn't able to work
because you didn't have any type of uh working papers,
and so someone had told him that the only way
he can make some money would be to sort of business,
and being a German immigrant coming to Canada, uh presumably
like where it's pretty cold relative to where he comes from,
he decided he wants those snowboards on the internet. And
(03:30):
when he began to look at how to sell a
product online back in two thousand four or so, there
were really two ways to do so. One way was
you would you would posted on a marketplace like an
eBay or an Amazon or an Etsy something like that,
which it was inexpensive but did not allow you to
build a real business if it was almost like you
were renting customers from that marketplace. But the other way
(03:50):
was you could build an online store. You could use
s a p or or Cole or a Magenta or
one of these sort of big enterprise piece of software
that I was like a million dollars to do, and
so uh disappointed with that With those options, he just
wrote a piece of software to sell his own snowboards
and created this snowboard shop called snow Devil, and very
(04:12):
quickly he realized that a lot of people like me
wanted to use the software to build their own businesses.
My sort of introduction to Toby was was actually through
my becoming what what what is now? I want to
shopifyes first customers. I had a T shirt shop that
I launched around two thousand and six. So just to
sort of jump around a little bit, so, I was
born in Montreal and Canada, grew up in South Florida,
bok Raton I went. I went to went to school
(04:33):
there as a kid. And then because I was born
in Montreal, my uh sort of the the equivalent of
in state tuition at McGill University was like eightellars a year,
which was just incredibly you know from a a bank
for buck perspective was it was amazing. So I ended
up going to going to mcgil for undergrad and I
was seventeen when I started and started a little T
shirt business selling T shirts universities and that was a
(04:55):
way to support myself and and and at a certain
point in undergrad a mentor of mine convinced me to
go to law school, not to become a lawyer, but
rather to become a better entrepreneur. To become an entrepreneur,
he sort of looked at law school is finishing school.
Um and and actually he was completely right about that.
And this particular mentor just happened to be teaching at
the University of Ottawa. So I applied to one school,
(05:16):
moved to Ottawa, had no friends, met Toby. He was
transitioning out of snowboards into software, and I said, Hey,
I'd love to start a T shirt business that would
run concurrently well in the school. And I set up
a T shirt shop online and and and then realized
there's no way I was going to practice law for
more than I think. I lasted ten months and then
called Toby in two thousand eight and said, I'm done.
(05:37):
I want to come join you, and and and uh
a handful of other engineers. I I was sort of
the first non engineer UH and and helped build this
great company called Shopify. And that was That was over
a decade ago. Law school is the finishing school. And
none of my mentors would have said that I am
not that type of entrepreneur because I'm not really that organized.
You know, I'm very dependent on folks like yourself who
can be a Chief platform officer a CEO. I'm desperate
(05:59):
for folks that around me. I'm curious, like, was that
already there were these characteristics that have ended up, you know,
leading you to be able to lead this organization through
its stages of growth. Young Harley had a ton of energy,
um and probably was a ball of untapped potential. I
talked about my first real business being you know, this
teacher business at mcgil that made you know, promotional teachers
(06:19):
for universities. But that's not actually completely true. Um. The
truth is my first business was a business I started
back in probably six. I was, you know, thirteen years old,
and I want to be a DJ. And I know
you DJ, and I know that or you you you're
around DJs a lot. I should say I actually I
DJ the situational tunes. I'm a big playlist playlist designer.
(06:41):
But I said that because I actually follow you and
Spotify and so I I sort of I wasn't sure
if you you would self identifies DJ or not, but
you certainly are into music. I know Brett actually is
a DJ now, and um, so I want to be
a DJ. I thought it was a really cool thing
to do. Like most other thirteen year ol Jewish kids,
I went to Bar Mitzvah's and I saw these DJs
and I just thought they were the coolest thing in
the world, not because they looked a certain way, but
(07:03):
because it felt like they were um creating energy from nothing.
They were able to put on a particular sequence of songs,
and the sequence of songs would lead to a change,
a dramatic change and energy that they can take someone.
They can take three people that are sitting down in
tuxedos having some rubber chicken. It's some you know, some
hull or some synagogue, and ten minutes later can have
(07:25):
every single person having a tie around their head, just
freaking out and dancing and having the time of their life.
And I thought that was such an interesting energy shift,
that was such an interesting way to uh, such an
interesting thing to do, and and I just wanted to
be a DJ, so I didn't. I called around a
bunch of DJ companies and said, hey, you know, like
I'm thirteen years old, I don't know much about djaying,
(07:46):
but I'd like to learn. And of course they said,
you know, get lost. UM. And so I decided that, um,
I would start my own DJ company, and I should
say one of the lenses that I should tell you
is that I'd always been very enterprising. Um but one
thing that my parents and stad my parents didn't didn't
have very much money. But one thing my my dad
in particular did was every single crazy little business idea
(08:06):
that I had, no matter how dumb it was, he
would make me business cards with my name on it
and that business name. And so from a very early age,
I always felt like even though these things some cases
never made any money um or they were not profitable,
my dad always made me feel like they were real.
And so I started this DJ company, ended up that
year moving from Montreal to to South Florida, and ended
(08:27):
up deejaying like five hundred bar Mitzvah's between like thirteen
years old and seventeen years old. And that was really
my first sort of business. And it didn't make that
much money, I think, you know, the equipment cost me
a lot. I had to pay staff and stuff, but
it was it was a great entrepreneur experience. So I
was always very entrepreneurial. And then when I got to
McGill it was two thousand one. My dad um had
(08:48):
just my parents never had a lot, but they lost
everything in in in the and sort of that that
sort of post nine eleven a couple of months and
they had no money. My mom actually called and asked
me to move back down to stuff sort of. And
I if any if you or any listeners have ever
been to Montreal in the summertime, It's just the most amazing,
magical place. It's sort of a mix of Europe and
(09:10):
has this great kind of vibe to it, the French
Canadian vibe is almost has a Latin feel to it.
It's just it's an interesting place. And I was not
going to leave Montreal, and so I just told my
mom that I will figure it out and I will
support myself and I will help support them if I could.
And I ended up building this T shirt business, making
t shirts for UM universities around Canada. And so I
(09:30):
don't think I was ever particularly organized, but I sort
of always had this insatiable growth mindset, the sensatiable desire
to learn, to build, to do stuff that I felt
a lot of meaning around. The reason that this, this
this particular suggestion of going to law school was so
interesting to me was because it's it's it actually, in hindsight,
(09:51):
is exactly the advice I would give someone today. Is.
Someone today said, what would prepare me to run a
company of the size of shop If I Shopify, you know,
is is almost a hundred billion dollar company depending on
what day you look. Um, So we were one of
the largest companies, certainly one of the largest tech companies
on the planet, but also one of the largest companies
on the planet. I would say that law school was
far more instructive, and it was far more valuable to
(10:14):
me than something like I also went to business did
a joint law and b A business school was not instructive,
was not helpful. It was all pedagogical, it was all
case studies. But law school taught me how to write.
It taught me how to think. It taught me how
to debate something as simple as being able to read,
you know, a thousand pages and pick up the one
single line that is the most important line. They call
it the ratio decidentity in in sort of Latin. But
(10:36):
that's the most important, that's the crux of the entire thing.
That is a skill that I never learned really up
until law school, and so it was really valuable for me. Well,
and we know so many stories of founders that don't
have that skill set who you know, uh, you know,
lost on a technicality or you know, signed a deal
or negotiated something but didn't do this type of review
(10:56):
for themselves ended up paying the price. So I imagine
when you know, join Shopify UM and in those early
early years and you know started you know, helping lead
the organization, I imagine that was a really valuable skill
set to bring to the co founders. And two, we
raise our first round of financing. It was a Series A.
It was led by Bessemer um by Jeremy Levine, who
(11:16):
is still on our board. Is one of the most
important people UM in my life. Professionally. He's just been
a huge mentor and he's been a great board member
for us. But we didn't have a CFO at that point,
and I think Toby and I sort of looked at
the docks and I think what law school gave me
was it didn't necessarily give me a playbook on how
to do a series A financing, but it gave me
the confidence that I would I'd be able to figure out, Okay,
(11:39):
what exactly is this? How do I what is a
liquidation preference? How do I look this up? How do
I how do I how do I explain it in
a way that makes makes sense, and so um that
I thought was really valuable, and the same sort of thing,
I mean, the things that we raised our series in
twenty ten. We took the company public um both in
New York and Toronto, dual listing in two thousand fifteen,
and now you know where we're six thousand people. One
(12:00):
of the things that I feel strongly about is that
a company like Shopify or any high growth company, the
people that are leading have to requalify for their job
every single year. And I think requalifying for your job
every single year puts the onus on you as the
individual that you just you gotta always be better. If
there is someone out there right now who's a better
CEO for Shopify, that person deserves the job. But I
(12:24):
I I want, I want the job, and I'm willing
to requalify for the job every year so that there's
no way there is a better candidate out there than me,
and the onus is on me to do than not
on Shopify, to sift through or to vet me. And
that's sort of what law school did for me, was
it gave me this um, this curiosity about exploring things
on a much deeper level. And uh, and that's it's
(12:45):
been instrumental. And so I know that I'm sort of
throwing shade a little bit of business school, but I
just especially in sort of a post COVID world, especially
when all these universities are going to a remote structure,
I simply don't think that I think you need to
go to university. You need to go to school to
take the skills out of it, not because you were
getting some sort of uh you know, some sort of
degree or piece of paper. I just that's just not
(13:05):
that valuable anymore. Really really appreciate you given us that
insight into the way that you think about this stuff.
And to your point, you know, it's pretty rare where
the founders and early operators of a of a startup
precede are the same guys around the time of the
Series B financing or C financing or the bigger later
stage financings. Let alone, once it's a publicly traded company
(13:26):
with you know, thousands and thousands of employees, I'm sure
that there's been some major growing pains. But you know,
talk us through that a little bit, because I'm sure
that you've learned a lot along the journey. Yeah, it's
what's cool about being in a place. So I'm I'm
thirty six years old. I think you're around my age,
maybe a couple of years younger older. So, um, I've
spent over ten years, over a decade a shop with that,
(13:46):
which which is, you know, like almost a third of
my life. And there's something about being at a particular
place for that long And one thing I think that
it does allow for is is really really high levels
of context. I mean, you've been you founded, but also
have been running Summit for I think a decade as well,
maybe more right, since she has eight you guys started
something like that. Well and and and that's the counterpoint.
(14:08):
I am still very involved in Summit, and I have
that cultural knowledge, but I am not the best guy
to operate, you know, a mountain development operation. So that's
that's why I'm so curious. Most of us who start
these companies don't have the same skill sets to operate
at scale um and that's something that gets lost. It's
like as these companies scale and you add you know,
you go from ten to fifty people, you lose culture,
(14:30):
let alone you know, fifty to five thousands, so to
have the founders in the positions. To have early leaders
in the positions that you guys have them certain has
a huge impact on the culture. So you're obviously right.
So in the context side one, it means that just
like you a summit um, I have a really really
great understanding of every aspect of Shopify, And that is
so right now. Shopify has you know, you know, over
(14:52):
six thousand people, we have over a million stores on
the platform. If you were to aggregate our stores just
in the US, for example, Shopify were not a retailer,
but if you pretend for a second that we are
a retailer, we would be the second largest online retailer
in America. There'd be Amazon and then Shopify, and then
like after that you'd see eBay and and best Buy
and home Depot and Walmart dot Com and all those.
(15:12):
But shopol is the second large zoneline retailer in aggregate.
And I think what comes with that is we have
a lot of different areas of our business. We have
a capital business. We've GETTN like over a billion dollars
withorth of cash advances. We have a payments business. We
have a logistics business of shipping business. We have a retail,
physical retail business, shopol point of sale, and and that's
just a slice of it. One of the benefits of
being at a place for a very long period of
(15:32):
time if you if you're curious about that place, and
you have a real um and you and and and
and and that place is something that you deeply care
about as as it is for me and it is
for you. With Summon, you do get a benefit in
that you sort of know exactly you're able to navigate
the company in a much more um in a much
better way, in a much more effective way. However, the
key to it, I think has always been you know
(15:54):
what our strengths are and know what our weaknesses are.
We like to hire people at Shopify for their strengths,
not their lack of weaknesses, which we've said publicly, and
that's something that is fairly well known. And so you
often have these like strength finder diagrams where you sort
of see they kind of look like stars almost like
people are very strong here but very weak in other places.
We're okay with people having weaknesses. In fact, in some
cases big weaknesses as long as our strengths are make
(16:17):
them really really unique. And so that's something we we
we use as a hiring metric or hiring a vector,
but we also think about it internally. I I am
actually not a very organized, not a detail oriented person.
I like the big picture, and so the people that
work with me, I need them to be incredibly detail
oriented because that's just not my skill set. On the
flip side, if there's a particular the business that I
(16:40):
simply don't think I have requalified to run UM. So
if you take any any area of our business at
the beginning, I'm an entrepreneur, I'm a founder. I'm a
startup guy. I love the early days and stuff, but
as particular perspective, I need to hand that off to
someone who's better suited for it. Um we we we um.
One of the things that I am most proud of
a Shoplin is building shop if I p us, which
is our our enterprise product, and we have you know,
(17:02):
everyone from from Kylie to Jim Shark to Bombs to
All Birds to like a ton of the biggest DTC
brands on the planet, all you Shopify plus UM. I
was totally the right person to get that started, but
at a particular point, running a two or three hundred,
you know, person effectively sales marketing and enterprise product division
wasn't for me. It's important. I think that leaders know
(17:24):
when they need to bring in someone else to to
help run that, and that that I think is just
self awareness. I think self awareness is probably the most
important thing of UM, at least for me, has been
the most important skill set to develop. Over time, we'll
be back with more out of the hustle after the break.
(17:48):
Like when I look at you know, the big sort
of incumbent power players and in the industry typically really
lack innovation. They can't really build like what's next, but
they can they can copy it really fast. So if
you look at like a Facebook and like, you know,
the best features on Snapchat are going to be on
Facebook as soon as they can do it right, or
on Instagram or whatever. And and you guys kept on succeeding,
(18:08):
you kept on growing. You were you're you're making money,
being experimental, being sort of front of the marketplace. I
want to know why talk to us a little bit
about that. I would love to understand what separated Shopify
to make it so this was the culture there. When
you sort of look through the review mirror, things do
a little bit things do look rosy, and certainly building
(18:29):
in an app store and a partner program, um you know,
a decade ago turned out turned out to be a
really great idea for a bunch of reasons that we
can get into um. But that actually came from a
very simple thing, a very simple decision, which is that
we did not want to build everything for everyone. We
wanted to create products that most people need most of
the time. And back in two thousands, ten or two eleven,
(18:50):
when really the partner program, we were just setting it up.
In the first place, we were building e commerce software
for small businesses that sold physical products online, and that
was it. And so if you needed us to convert
shoe sizes from American sizes to European sizes, yeah, maybe
that's something that you know, some people need some of
the time or some people need most of the time,
but that's not what most the most most people most
(19:11):
of the time don't need that. And so instead of
actually building out every feature under the sun, we said, well,
what if we did this. What if we said Shopify
is going to provide the use case, the product market
fit for eight percent of what everybody needs that wants
to sell physical products online in a small business context,
and what if we allowed third parties to build that
last what would happen? Well, the result of it is
(19:33):
that one these third parties can now build something and
they can make real money, they can create We can
create more value for them than we capture for ourselves.
I've said this a bunch of times publicly, but you
know there's sort of that that famous Bill Gates line,
which is you know, you've built a platform where you're
able to create more value for the platform for the
third parties and you capture for yourself. I mean Shopify,
(19:53):
you know last year did a billion and a half dollars,
but the ecosystem made close to six billion dollars last year.
And some of the are big companies, but a lot
of them are you know, two three single person shops
that just build apps for Shopify. So we've always sort
of took a bit of a more platform approach to
to building software and and and to building the product.
And now the result of it is that no matter
(20:15):
what your your use cases, you can get just about
product market fit on Shopify, regardless of what are the
particular nuances of your business, because our eight percent gives
you coverage, but the other really customizes it for you.
And then as we sort of continued, it became clear
that Grand two thousand thirteen that Okay, we're not really
in the e commerce business. We're actually the commerce business.
(20:37):
And then you have to sort of think, Okay, what
does the future of commerce look like? Is the future
of commerce going to be some omni channel It's gonna
be uh, some sort of um, you know, combination of
online and offline. Our view was no, actually, it's not
going to be that the future of commerce is gonna
be retail everywhere that in the future, unlike the past,
the consumer is gonna dictate to the retailer, the brand,
(20:58):
or the or the business how they want to purchase.
And if a consumer says I want to buy on
Facebook or Instagram, that's the way you have to sell it.
And if the consumers is I want to buy offline
and physical beautiful you know, downtown boutique, that's we have
to sell it. And it might be online and it
maybe on Pinterest or house or wherever and so around too.
Doesn't thirteen are objective change from building beside this sort
(21:20):
of being the best e commerce software for small businesses
to really just being commerce software, and we began to
sort of use the term retail operating system that what
if we were the world's first retail operating system. And
then around two fift and camera and sort of pre
i PO, something else happened, which is dramatic, which was
that some of those businesses that started on Shopify at
(21:42):
their mom's kitchen table, very very small businesses. In some
cases they grew to be category leaders. They grew to
be the the They were no longer the insurgents. They
became the incumbents. And give us, give us some examples. Yeah,
this is sort of Jim Shark movement watches um. These
type of businesses that simply almost overnight became truly leaders.
(22:03):
Um and all birds and bombs didn't come to a
little bit later, Tommy John. Some of these businesses got
really really big on Shopify, really really quickly. And the
interesting part there, the the insight was if you think
about software as an industry generally, what you tend to
see is this if you just take some like email marketing,
when you sort of the pro sumer starts using the
BCC line in in email, and then that prosumer becomes
(22:26):
a small business, a very small business, a micro business,
and they maybe start using something like male Chimp, or
they start using constant Contact. Eventually they may upgrade to
exact target, and eventually they may use they may use
some sort of like Oracle version of that UM. But
there tends to be a transition or a graduation in
software as you get bigger. What we encountered sort of
pre I p o um Or in fourteen was that
(22:48):
the businesses that had been starting on Shopify, they were
growing really really big and they were not leaving the platform.
And so again there was a new thing to think about.
There was a new um, a new piece of insight,
which is, wait a second, maybe we're not just e
commerce software or commerce software, and maybe we're not just
for small businesses, but maybe actually larger companies can use
as well. And that really was the formation of Shopify
(23:08):
plus and and and shopy plus was really just created
as a place for the most successful businesses to graduate
two as they got really really big and and and
and that was happening. But then something else happened, which
is that a bunch of really large companies, whether it's
you know, brands like Yeasy or was Procturing Gambler or
Unilever and Nestle or Heinz, ketchup Um or Nutrogena. They
(23:30):
began to come to shopify Plus and say, hey, look,
we don't want a six month sales cycle. We don't
want to spend fifteen million dollars. We just want to
get something up right away that's super scalable, that's super beautiful,
and we want to have modern technology. And so Shopify
Plus became a landing pad for a lot of those companies.
And some of them actually, uh, you know when I
met Blake from Tom Shoes at at a summit and
(23:52):
and what Blake said to me was and funny enough,
Andy from from UM from Manobos also the same thing.
That these were sort of version one or sort of
the first era, the first gen of DTC brands, and
Blake had no choice but to build custom software, so
did so did Bonobo's UM. But what was happening was
Auntie dozen fifteen. These companies are like, why do I
(24:13):
have three engineers when I can gc Shopify Plus and
actually talk. So Tom Shoes that came over, and Rebecca
Minkoff came over, and Steve Madden came over, Nicole Miller,
And so that's a long answer to very short question.
But that sort of does paint the picture of why
I think we've been able to innovate is because we
just were always questioning past assumptions. Are we really e commerce?
What is commerce? Are we really small business? What a
(24:35):
small businesses look like? And I think we've been able
to do a pretty good job of staying ahead. Um,
lots more to do, but that's sort of how we
look at the world. You mentioned Blake, you mentioned Andy
at Bonobos, like, these are companies that specialize in shoes
and pants, not technology. So here we are like they
they have to now make that jump to the next
level of their software to empower their business, and they
(24:57):
certainly aren't going to do it in the house, and
if they do, it's going to slow them down tremendously.
Whereas with you guys, it sounds like you. The reason
that you kept on innovating, the reason you kept on
adding these partner programs and projects and you know support
system that ecosystem approach is because um, this is the
life cycle of I just never knew that. That's amazing. Well,
I mean, I think the contract we have with like
not not the legal contract. But but but actually the um
(25:20):
the agreement we have with our merchants, these million stores
is that when you hear something that comes out in commerce,
whether it's Facebook announcing shops, or it's Pinterests adding Bible pins,
or it's Instagram doing um, you know, direct purchase UM
right on Instagram, Uh that day you If you're on Shopify,
we have a responsive and make sure that you're able
(25:42):
to use that technology that but by by choosing Shopify,
you will always ensure you have the most modern version
of whatever commerce is, whether that's Apple Pay or Shopify pay,
or it's Android pay or for for the accelerated checkout,
or it's cross posting on different marketplaces or cross posts.
I mean we just didn't. I announced the deal couple
WEE with Walmart because Walmart dot com is now a
lot of congartulation, which is really cool. Now, most of
(26:04):
the stores on shop if I don't necessarily want or
need to sell on Walmart dot com, but there are
thousands of stores that absolutely would love to cross sell
their products UM and and and and their brands on
on Walmart dot com. And so five years ago or
ten years ago that would have to be flying them
flying out to Bednville, Arkansas and meeting a retail buyer.
Now they don't have to do that. Now they're using
by being on Shopify, through the Shopify dashboard, the admin,
(26:26):
they can simply activate that channel and and and and
get UM hopefully get approved to to cross sell. So
that's the covenant we have with them where which is
I think why you've seen so many folks come over
to us UM and we wear that responsibility really heavily.
That that that's that is what I think is is
is what makes us a good company. But it also
means that it also there's a great deal responsibility when
(26:48):
you take that on. And I think that's the reason
why some of the biggest brands on the planet trust us.
Shifting Gears here a little bit to talk a little
bit more about you and a little bit more about you, know,
your style, leadership and both person only and professionally. I'm
sure it's felt inside your company as it is outside.
But like you're such a humble dude. You and Tobias
are like so kind, so nice, so generous, Like in
(27:10):
all your conversations, one would forget that you're running you know,
a hundred thirty billion dollar company with six thousand employees.
And I want to know, like, you know, do you
have like a daily practice, are you meditating? Like how?
And has this been has this been an active pursuit
for you guys to not let you know the success
of this go to your head or is it just
(27:32):
sort of your personalities? I mean, I think building a
company like Shopify in Canada, Um, I just I gotta
spend a moment on sort of geography because I think, um, again,
I sort of had a taste of both worlds. You know,
born in Canada, but I sort of feel like I
spent my formutive years in the US and Canada to
me is is Canada sort of like America for Europeans.
(27:52):
Is kind of the best way that I can put
I know, you spent some time up here in Toronto,
out of places, but um, there is a little bit
of um. One of the best parts of Anada is
sort of this this modesty that is just in the
air that it is not cool to be boastful, it
is not cool to uh to kind of lose yourself
in your own ego. UM. And I think now, by
the way, that's not always a good thing either. Um.
(28:12):
Sometimes Canadians generally are are overly humble. They don't you know,
our Prime Minister Um talks about that candidates more swagger.
I think that's right. I think we do need more swagger. Um.
You know, if I ask your name five tech companies
from Canada, you can name Shopify and maybe you'd say
something like Nortell or BlackBerry, which are both really not
not around anymore. UM. We tend to be on the
acquiring side of the of the book, not the acquirers,
(28:35):
which is because I think there's a little bit of
an inferiority inferiority complex that exists up here. UM. But
I didn't grow up here and so I have less
of that, and Toby grew up in Germany so he
is less of that also. But in terms of you know,
keeping uh, keeping our focus, I think the best thing
that that certainly Toby and I would both agree on
is um are our our partners, are our our our wives,
(28:55):
UM our life partners. Have been incredibly instrumental in that
because I've been with Lindsay since well before Shopify, and
and Toby has been Fiona for for this the same
the same thing. So there's a little bit of of
there are people around us that holds accountable. There are
some people that call us out on our our our
bullshit when when that exists, UM, similar to you. I
know you have a similar dynamic. But my best friends
today are still the best friends that I had when
(29:16):
I was a kid. Um. And and no matter you know,
how well I'm doing or how well the company is doing,
they're still gonna call me out of my on my stuff. UM.
But we've also, you know, Toby and I started seeing
a coach back in two thousand and eleven, or I
would say, um on on a recommendation of a of
a mutual friend, and um. We ended up loving coaching
so much that we ended up hiring the coach full time.
(29:37):
His name is Cam and then he came into the
Shopify and we asked him build a coaching practice. And
so there are sixteen or so full time coaches UM
staff at Shopify. And we actually we had a coach
on staff before we had a CMO, I think even
before we had a CFO potentially. So that sort of
performance management, growth, leadership growth thing is sort of embedded
in our culture, but it's just it's not the type
(29:58):
of place where you know, walking around um, like you know,
with with with a big head and walking around the
modest gets you very far. In fact, I think the
anti antibodies that Shopify sort of reject those things. They
sort of push you out and and we we don't
necessarily um people have come into our company that have
had ridiculously impressive backgrounds and cvs and have built huge
(30:18):
companies and made tons of money. And it doesn't always
work out because sometimes they simply, um, they they don't
come in as with the right curiosity, they don't come
in as an anthropologist who kind of needs to look
at Shopify and understand it before they can have an impact.
And then on the sort of you know, mental health
side of things, um, you know, frankly, it's it's been
tough for me. I'm a you know, Tim Ferris calls
me a power extrovert, and I think that's probably accurate.
(30:40):
I I love being around people. That's where I get
my energy. On a on almost every Friday night you
can have you can find my wife and I hosting
you know, shove at dinners at our at our home
with tons and tons of friends, and and that's just
kind of how we've always lived, and it's been I've
had anxiety since I was a kid. I feel like
my anxiety has been accelerated far more than sort of
co bit hit and and I've just sort of been
(31:02):
doubling down with things that keep me grounded. And probably
the most important thing other than just a daily ten
minute uh inside tim er mindfulness practice has been time
with the kids. UM. And I have two daughters, Bailey's
four and Zolway's one and a half. And and I've
I've rescheduled my life and so I start my day,
you know, walking the dog with the girls. I finished
(31:22):
my day walking with the whole family. UM. I've tried
to be very intentional about how to kind of make
this all work, because the truth is, I've been really lonely.
I've been more lonely in the last three months. And
I have you know, any any time I can remember. UM.
But I'm also talking. I mean the reason that I'm
I'm I'm okay with talking about it on on on
on your podcast, if is that I think it's important
that we all kind of share not just the highlight
(31:43):
reels of what's going on, but also those tough days. UM,
because I think there's a little bit of bravado that happens,
particularly in tech Um and it's a little bit easier
to be outside of the valley and outside of the States,
but there's a bit of bravado that happens um and
not every day I'm feeling my best um. So yeah,
that's that's kind of how we do it. And I
think the other thing is, you know, taking you back
(32:03):
to Summit for a second. One of the reasons that
I went to Summit was surround myself with people that
were better, smarter, faster than I was. And that's what
Summit did for me for for many many years. It
allowed me to sit at a table and meet asked
so like, you know, who are you, what do you do?
I'm chef, You're the supermantion. Yes, Like, just having conversations
like that are just so mind blowing. I remember I
(32:26):
remember meeting Robin Arson at at one of someone that
sees before Peloton had blown up, and just hearing her
story her transition from law into you know, like basically
helping to curate a curriculum for this small company called
called Peloton that I think is so valuable and I
think a lot of us, despite my saying that my
best friends are so most the best friends since I
was a kid. My network, the people that I I
(32:48):
speak to on a daily basis sort of these mentors
in my life. Um. One of them is the best
father I've ever met, and I want to emulate the
way he is a father. He's actually not very good
at many other things, which he would admit to, but
he's just the world's greatest dad. I have another friend
who just really understands, like, really family dynamics really well,
particularly when you know when when money is involved, and
and I really want to emulate the way he structured
(33:10):
his family. And another one it's just the most amazing, um,
you know, philanthropist and loves to give his time and
his money to charities and make a real impact. And
so I've been able to curate a group of sort
of mentors that I kind of swapped in and out
depending on what I'm focused on, who are so much
better than I am at those things, and um, and
that really helps. I had a friend who gave me this,
this piece of advice, and he was a very successful
(33:32):
real estate developer and he had retired in his late
thirties to spend time with his family and his friends,
and he got presented this amazing opportunity to do this
development that he had dreamed of. And so he was
coming back out of retirement and like raised more money
and was like building the team and getting excited, and uh,
his wife pulled him aside and was just like, hey man,
just so you know, no one that you love the
(33:54):
most or that loves you the most, will care or
will love you anymore or less based on your success
or failure of this venture, right, and so having people
in your life that aren't measuring you by that yardstick
is just like so important. And I think for you guys,
I don't even know if you ever like, you know,
built that. A lot of us just have that, you
know around us, you know, and you desire it. At
(34:14):
least I did. I. I had, you know, an ego.
I wanted to feel special or valuable or successful or
any of those they are looked at that way, you know,
in my in my twenties of course. And so that's
that's a that's a tough thing, right, Like it it's tough.
And and you know, I, uh, I grew up with
two very loving parents, parents that also believe I can
do anything. And I'm not sure coddling is the right word,
(34:36):
but I was sort of always I was, you know,
I was really lucky that I had very supportive people
around me. The problem was, um, like most of us
when you know, in my in my early twenties, I
kind of thought I knew what I was doing. I
kind of thought when I built this T shirt business,
I made a little bit of money, and I did
this other thing, and I made some you know, I
got to law school and I did all these things,
and it was really cool. That's the value of surrounding
yourself with people that are truly better than you in
(34:57):
in in a whole bunch of different categories, because you
begin to it's like, you know, it's we use it.
We use the metaphor of boxes at Shopify that um
the sort of a series of box. At the bottom
of every box, you're shaky, you're uncertain, things are not
necessarily um, you're not confident. And then eventually get to
the top of that next box, that box, and that's
where you start. You begin to get that swagger. You
begin to get confident, maybe even cocky. If you have
(35:19):
people around either reach their hand down and then bring
you into that next box, even though the bottom of
the next box you're going to be incredibly shaky. That
is super valuable. And UM, I think that is the
value of having, you know, a tribe or a community
around you to kind of help you with with that process.
But I gotta tell you, like I, UM, my biggest
challenge when I first joined Shopify wasn't the work. It
(35:40):
wasn't the company. It was myself. It was that I
didn't I I didn't I wasn't self aware. I didn't
necessarily have this insatiable growth mentality or this curiosity. I
felt like whatever I had done, UM, I was able
to you know, I was. I was proud of that,
but I thought that that mattered. UM And I didn't
certainly did not have this idea that I'm gonna have
to read qualify for the things that I currently have
(36:02):
professionally every single year. UM. And I gotta tell you,
I'm a lot happier now, I'm a lot more mindful now.
My relationships are richer now, and I'm I'm just I'm
I'm happy. I'm a better human being now than I
was then. And and the way it manifested itself was
in the early days, remember not wanting to hire anyone
better than me because I thought that if I hired
something better than me, uh, it meant that I was
(36:23):
less valuable or less valued. And it just that's the
furthest thing from the truth. Now, like everyone who I've
hired is so much better than me, and that makes
me better and that makes me very proud. The journey
has been great. Art of the hustle will be right
back after this short break. I'm curious, you know, for you, now,
(36:48):
what do you still do too much of? It's a
good question. Um, I think I probably spend uh too much.
So it's funny if you sort of think about like
work as being kind of three different UM categories, sort
of um in the weeds, um kind of the middle work,
and then sort of up top is kind of the
large strategy stuff. I tend to kind of operate in
(37:08):
either the bottom or the top. I tend not to
do the middle stuff UM, and I probably should be
a little more balanced, But I do get into the
weeds sometimes and things that I just I just I
care a lot about. Um. There are particular areas of
Shopify that I'm so um. Maybe two to the detriment
of the group and that made a detriment of me.
I'm overly attached to and I need folks to basically say, hey,
(37:29):
look I got this. Uh. And it's not to say
like I know that's a sort of a tip prototypical
you know thing where I'm too I'm too focused, none
of that crap. I just sometimes I get too far
into the weeds on something that I sort of forget
the bigger picture. And UM, that's sort of where UM
curating my calendar in a way that actually allows me
to have the highest impact that I think is is
(37:50):
really important. But one thing that I did do UM,
I brought some more things in my life that I
just are just fun for me. UM. I still take
calls with certain merchants that are thinking of migrating over
or that are thinking of launching on Shopify, because what
I realized was there are certain things I just I
don't need to be involved in everything, because there's no
way to run a company at our scale if you're
If you're involved in too many things, I become a bottleneck.
I never want to be a bottleneck. But there are
(38:11):
something that are fun for me and the things that
are and I believe that, Um, I believe that we
all need to kind of figure out what those things are.
For you. Maybe it's something as simple as the music
at an event for summit. And you may be like,
I know, we have like the greatest music producers like
on on retainer on standby, like the most famous you know,
I think you guys basically like quest Love on retainer
at some which is amazing. But sometimes I bet you so,
(38:34):
you know, I like, let let Jeff just deal with
this because I just want to do this. I think
it's important to remain to have some fun and um
and not lose that sense of of of fun and
and so I allow myself, um, the opportunity or or
the freedom to kind of get into the weeds sometimes,
but I think I probably do it too much. My
worry is, like there's the funny the podcast called The
(38:56):
Art of the Hustle, and that is such like a
you know, twenties mentality from me right where it's like
you hustle, hustle, hustle in terms of like the the
language that we're that we're using to describe it. And
and there's a limitation to what that can get you, right,
and then you have to gain wisdom not from your experiences,
but ideally from reflection. And I have an issue where
(39:17):
I'll just end up scheduling my days so packed so
repeatedly and not really save time for reflection when I'm
in like a work mindset. And so that's what I'm
trying to get more of for myself. Then that leads
me to my next question for you. You know, I
want to know what do you want more of right now? Yeah?
I am, I'm fairly type A UM and I find
(39:38):
and I'm sort of incredibly goal oriented. I'm I'm trying
to look for things right now that I actually can
just um can just be at so UM. I started
running two years ago. I always want to run, never
figured out a way to run it, just I was
always sore, like I would. I can cycle for you know,
hundred and two hundred k, but I was never able
to run. So I got a coach and began to
(39:59):
sort of in going about running and running technique. And
then of course that always leads to the uh the
next stage, which is, okay, when are we gonna run
a half marathon? Or when are we gonna run a marathon?
It just like I feel like I'm always in conversations
with sort of my running group about that particular thing.
And I actually decided to um to sit out and said, hey,
I'm not going to run a half marathon. I don't
(40:20):
want to run a marathon. I just want to enjoy
going for a run. You know. I bought the garment watch,
and I made sure that I was tracking everything on Strava,
and I, you know, I was, I was being a
really good type a entrepreneur, and I just started enjoying
it less um or or you know, the same thing
with cooking. I got really into cooking a couple of
years ago. My wife as a food entrepreneur. She also,
you know, is a has been a fairly well known
(40:42):
blogger and the Canadian food scene for a long time.
And so I was like, you know, I'm gonna cook.
And then it was a matter of like, I'm gonna cook,
and I'm gonna I'm gonna play it in a particular
way that just looks so amazing and and and I
stopped enjoying so in the same way that I stopped
enjoying running once I started to think about the marathon
or half marathon, I stopped doing cooking when I sort
of felt that I'm doing it for the destination, and
(41:02):
some things, I just want to enjoy the journey. And
I know that sounds, you know, cliche, but some things
like I just want to go out for a run
sometimes and if I run for ten minutes or thirty minutes, uh,
they listen to music or a podcast, whatever it is.
I just want to enjoy that. And um, I'm not
necessarily I'm not good at that. I'm actually really bad
at that. Um. And so I'm intentionally now saying I'm
gonna cook and like, if it looks great, whatever. If
(41:24):
it doesn't look great, that's okay too. It'll be delicious,
and I'm going to enjoy the process and my family
is gonna absolutely love it. Being more mindful about that stuff,
I think is really important. And because everything in my
life is basically quantified, whether it's you know, the stuff
and doing at the office, or it's the stuff that
I'm doing, you know, on on sort of the the
investment side or on the on the philanthropic side, it's
(41:45):
all quantifiable. I want to have some stuff that is
a little bit more um right brained in my life.
And and so I'm really struggling to kind of pull
back from some of those things as much as possible.
But one thing I don't want to say, just coming
on the previous comedy made around sort of the art
of the hust soul, is this. Have you actually scrolled
back through my timeline for like three hours and you
get to like two thousand thirteen, you're gonna you would
(42:07):
see basicuteen two dozen eleven. It doesn't thirteen. Almost every
single tweet that I had ended with hashtag hustle. It's
sort of a It was a personal philosophy for me.
Um I had learned it from from from Gary v
and and and and um I'd spent some time understanding
his philosophy around you know, perseverance and just you know,
running through walls at all costs. And it was just
(42:28):
it was an interesting kind of life philosophy for me.
And actually Tina Eisenberg Swiss Smiths, who has a great
company called Tatley Check, she made me as a gift
after sort of seeing this all um all emerge Um.
She made me a gift business cards that that also
doubled as a temporary tattoo that said hashtag hustle and
and and um and yeah and and and so I
just I probably gave out those business cards at a
(42:49):
bunch of summits UM and and at some point it
became sort of UM synonymous with Harley at least a
Shopify that you know, Harley was kind of this hashtag
hustle guy. And one of the as I realized was
people began to misinterpret it, and I actually realized that
what was happening was UM. People interpreted hashtag hustle as
this kind of strange UM work hard mentality. They they
(43:14):
there was no there was no room for nuanced, there
was no room for optimization. It was if you have
to get something done and it's gonna take a hundred
phone calls, you do the hunter phone calls. And actually
that's never what I meant. What I meant by it
was you actually figure out who are the three people
who are most likely going to lead to UM an
affirmative answer or or or a yes in the other line,
and you call those three people. And so funny enough,
(43:36):
I'm glad you're you're you're thinking about sort of the
history of the term, because at shopify, I actually it
became UM. It became something that I actually regretted introduced
with the company, and so at some point I almost
had a funeral for it at the company. I did, uh.
I gave it's hawk at a town hall and I said,
I'm actually retiring hashtag hustle because it's been it's been misinterpreted,
and it's not really just about working hard. It's also
(43:57):
about working smart. It's about being strategic Western things. It's
about um, you know, finding hacks and finding ways to
kind of skip the queue and and um so I'm
just I thought that was an interesting kind of segue.
And what got you here won't get you there. It's funny.
I'm sitting here at my desk in my office talking
to you about it. And I have a momento more
eye skull sculpture that says, never put off tomorrow what
(44:17):
you can do today, And it's the only words they're
looking at me on my desk, and so here I
am being like, yeah, man, you know, I really want
more reflection. But the the the mementos, the totems that
I have around me are still towards the temple of
the hustle, you know what. And I actually I changed
the artifacts in the in my office around on video now.
But if you were to see in my office here
I'm at my house. My artifacts changed from like you know,
(44:40):
I had like a Morgan Stanley made like the skateboard,
uh sort of deal tombs and we did a fund
raise um post I p O and they made me
sort of the deal tombstone was actually a skateboard because
they know I skateboarded. And actually I used to have
that up my office and I'd actually changed it now,
um with with actually pictures that my kids have made
for me. So like these are like crayon drawings, and honestly,
it makes me so much happier to have those in
(45:01):
my office. Is my backdrop than something like these sort
of three hundred million dollar deal tombstones. Um. So hey,
look I'm I'm going through what you're going through also,
which is that I think we're all trying to figure
out what how we operate in this new world, how
we find time for mindfulness and how we find time
for just being. But it's difficult because you know, to
your point, what got you here won't get you there.
(45:21):
What got us here is it's very much in our firm,
where it's it's you know, it's it's our Um, it's
not our prefrontal cortex working, it's our amygdala working. In
many cases, it's our lizard brain. And for a lot
of entrepreneurs that are listening to it, our lizard brain
is the reason that we got here, and not not entirely,
but some parts of it our desire, our ambition, our
work ethic And so it's very difficult to get to
(45:42):
a particular point and say, Okay, now I'm gonna stop. Now,
I really want to just double down on my mindfulness
practice in my yoga, and I want to make sure
that I i you know, I'm able to be artsy,
and I want to be able to live in the moment.
And it's just really difficult because we've been sort of
you know, we've we've had hundreds of years of of
of of breeding on this. But so for those entrepreneurs,
at some point you were doing everything yourself, and so
(46:03):
at some point just deciding you're not gonna do everything yourself,
you're gonna get out of the details of the weeds.
It's just not an easy thing to do sometimes. Thank
you for the time, Harley. I love you. You're incredible.
You're such an amazing dude. You're such a like, great,
great person and clearly just like it. For me, it's
like you said, you know, coming to summit and getting
to meet people that are brilliant and wonderful people and
(46:25):
wonderful entrepreneurs and you know, learning from them, you know,
like you I was, you know, as a decade ago.
So I was in my early twenties, which means by
definition you pretty much don't know ship and you know it.
For for me and for my partners, to see what
you guys have been able to do and how you
carry yourselves and what you value has been really inspiring
(46:46):
and really impactful for us. So thanks again for being
on the podcast, Thanks everyone for listening, and Harley Man
keep rocking, dude. Oh thanks Jeff. Appreciated For more podcasts
(47:13):
for my Heart Radio, visit the I Heart Radio app,
Apple podcast, or wherever you listen to your favorite shows
Art of the Hustle is a production of I Heart Radio.
You're listening to the Art of the Hustle, the show
that breaks down how some of the world's most fascinating
people have hustled and learned their way into achieving great things.
(00:21):
I'm your host Jeff Rosenthal, co founder of Summit, and
on today's episode, I had the pleasure to interview my
friend Harley Finkelstein, CEO of Shopify, Canadian entrepreneur and just
all around great guy. We discussed his amazing journey from
two thousand eight joining a small startup at Shopify, and
then growing it to a publicly traded company with over
(00:41):
six thousand employees, a hundred and thirty billion dollar market cap,
and over one million entrepreneurs operating stores on their platform.
I was pretty blown away to learn how Shopify has
maintained its culture over the last fourteen years, it's innovative
and experimental edge even as they've achieved massive success, and
(01:01):
how they've always seemed to be way ahead of the
curve when it comes to channel partnerships, technology and new
resources for its user base. And just simply get to
know Harley better, who is honestly a role model for
me and how he carries himself and how he approaches
his work. So please enjoy my conversation with Harley Finkelstein.
Thank you so much. I really appreciate it. I know
(01:23):
that you're you must be you know, slam the the
moment that we're in with with the pandemic and COVID
and just you know, I was reading some of the
stuff you've been, you know, saying in public recently and
the interviews have been doing just on the decade that
we jumped in terms of you know, bringing twenty I
imagine that you know, has a direct impact on the
(01:44):
amount of work that you have on a daily basis. Yeah,
you think about e commerce, So did like online commerce
as a percentage of total commerce went from someone like
five percent in two thousand eight until like eighteen, So
it took about ten years to get there. And we
basically have gone from fifteen percent uh to about twenty
(02:04):
five in the last ten or twelve weeks. So we've
seen effectively a decade worth of conversion to digital commerce
and retail um in the last you know, three three
four months, and it's it's been dramatic and frankly, what
we see is a sort of a tale of two worlds.
And you can use this lens for not just retail,
but you can use it for entrepreneurship or business in general.
(02:24):
You see a resiliency on one side, and you see
a reluctancy or or a resistance on the other side.
Some retailers and businesses have been resistant to change, and
they have floundered, and they have they've they've suffered some
really tough times, and others have just become incredibly resilient
and have changed their business for the better indefinitely. Yeah,
this is one of the things that Simon Sinek was
(02:45):
actually talking about on the podcast. Those that survive are
the ones that can pivot their way out of It's
just an incredible moment in time. And you know, we've
been friends now for I guess close to a decade.
We started Shop A five two eight. Correct. The story
of company actually goes back even further. It goes back
to around two thousand five or so. Actually two thousand four.
Toby had moved from Germany to Canada for the best
(03:08):
reason possible because he met a girl who's now his wife.
Came to Canada's new immigrant didn't wasn't able to work
because you didn't have any type of uh working papers,
and so someone had told him that the only way
he can make some money would be to sort of business,
and being a German immigrant coming to Canada, uh presumably
like where it's pretty cold relative to where he comes from,
he decided he wants those snowboards on the internet. And
(03:30):
when he began to look at how to sell a
product online back in two thousand four or so, there
were really two ways to do so. One way was
you would you would posted on a marketplace like an
eBay or an Amazon or an Etsy something like that,
which it was inexpensive but did not allow you to
build a real business if it was almost like you
were renting customers from that marketplace. But the other way
(03:50):
was you could build an online store. You could use
s a p or or Cole or a Magenta or
one of these sort of big enterprise piece of software
that I was like a million dollars to do, and
so uh disappointed with that With those options, he just
wrote a piece of software to sell his own snowboards
and created this snowboard shop called snow Devil, and very
(04:12):
quickly he realized that a lot of people like me
wanted to use the software to build their own businesses.
My sort of introduction to Toby was was actually through
my becoming what what what is now? I want to
shopifyes first customers. I had a T shirt shop that
I launched around two thousand and six. So just to
sort of jump around a little bit, so, I was
born in Montreal and Canada, grew up in South Florida,
bok Raton I went. I went to went to school
(04:33):
there as a kid. And then because I was born
in Montreal, my uh sort of the the equivalent of
in state tuition at McGill University was like eightellars a year,
which was just incredibly you know from a a bank
for buck perspective was it was amazing. So I ended
up going to going to mcgil for undergrad and I
was seventeen when I started and started a little T
shirt business selling T shirts universities and that was a
(04:55):
way to support myself and and and at a certain
point in undergrad a mentor of mine convinced me to
go to law school, not to become a lawyer, but
rather to become a better entrepreneur. To become an entrepreneur,
he sort of looked at law school is finishing school.
Um and and actually he was completely right about that.
And this particular mentor just happened to be teaching at
the University of Ottawa. So I applied to one school,
(05:16):
moved to Ottawa, had no friends, met Toby. He was
transitioning out of snowboards into software, and I said, Hey,
I'd love to start a T shirt business that would
run concurrently well in the school. And I set up
a T shirt shop online and and and then realized
there's no way I was going to practice law for
more than I think. I lasted ten months and then
called Toby in two thousand eight and said, I'm done.
(05:37):
I want to come join you, and and and uh
a handful of other engineers. I I was sort of
the first non engineer UH and and helped build this
great company called Shopify. And that was That was over
a decade ago. Law school is the finishing school. And
none of my mentors would have said that I am
not that type of entrepreneur because I'm not really that organized.
You know, I'm very dependent on folks like yourself who
can be a Chief platform officer a CEO. I'm desperate
(05:59):
for folks that around me. I'm curious, like, was that
already there were these characteristics that have ended up, you know,
leading you to be able to lead this organization through
its stages of growth. Young Harley had a ton of energy,
um and probably was a ball of untapped potential. I
talked about my first real business being you know, this
teacher business at mcgil that made you know, promotional teachers
(06:19):
for universities. But that's not actually completely true. Um. The
truth is my first business was a business I started
back in probably six. I was, you know, thirteen years old,
and I want to be a DJ. And I know
you DJ, and I know that or you you you're
around DJs a lot. I should say I actually I
DJ the situational tunes. I'm a big playlist playlist designer.
(06:41):
But I said that because I actually follow you and
Spotify and so I I sort of I wasn't sure
if you you would self identifies DJ or not, but
you certainly are into music. I know Brett actually is
a DJ now, and um, so I want to be
a DJ. I thought it was a really cool thing
to do. Like most other thirteen year ol Jewish kids,
I went to Bar Mitzvah's and I saw these DJs
and I just thought they were the coolest thing in
the world, not because they looked a certain way, but
(07:03):
because it felt like they were um creating energy from nothing.
They were able to put on a particular sequence of songs,
and the sequence of songs would lead to a change,
a dramatic change and energy that they can take someone.
They can take three people that are sitting down in
tuxedos having some rubber chicken. It's some you know, some
hull or some synagogue, and ten minutes later can have
(07:25):
every single person having a tie around their head, just
freaking out and dancing and having the time of their life.
And I thought that was such an interesting energy shift,
that was such an interesting way to uh, such an
interesting thing to do, and and I just wanted to
be a DJ, so I didn't. I called around a
bunch of DJ companies and said, hey, you know, like
I'm thirteen years old, I don't know much about djaying,
(07:46):
but I'd like to learn. And of course they said,
you know, get lost. UM. And so I decided that, um,
I would start my own DJ company, and I should
say one of the lenses that I should tell you
is that I'd always been very enterprising. Um but one
thing that my parents and stad my parents didn't didn't
have very much money. But one thing my my dad
in particular did was every single crazy little business idea
(08:06):
that I had, no matter how dumb it was, he
would make me business cards with my name on it
and that business name. And so from a very early age,
I always felt like even though these things some cases
never made any money um or they were not profitable,
my dad always made me feel like they were real.
And so I started this DJ company, ended up that
year moving from Montreal to to South Florida, and ended
(08:27):
up deejaying like five hundred bar Mitzvah's between like thirteen
years old and seventeen years old. And that was really
my first sort of business. And it didn't make that
much money, I think, you know, the equipment cost me
a lot. I had to pay staff and stuff, but
it was it was a great entrepreneur experience. So I
was always very entrepreneurial. And then when I got to
McGill it was two thousand one. My dad um had
(08:48):
just my parents never had a lot, but they lost
everything in in in the and sort of that that
sort of post nine eleven a couple of months and
they had no money. My mom actually called and asked
me to move back down to stuff sort of. And
I if any if you or any listeners have ever
been to Montreal in the summertime, It's just the most amazing,
magical place. It's sort of a mix of Europe and
(09:10):
has this great kind of vibe to it, the French
Canadian vibe is almost has a Latin feel to it.
It's just it's an interesting place. And I was not
going to leave Montreal, and so I just told my
mom that I will figure it out and I will
support myself and I will help support them if I could.
And I ended up building this T shirt business, making
t shirts for UM universities around Canada. And so I
(09:30):
don't think I was ever particularly organized, but I sort
of always had this insatiable growth mindset, the sensatiable desire
to learn, to build, to do stuff that I felt
a lot of meaning around. The reason that this, this
this particular suggestion of going to law school was so
interesting to me was because it's it's it actually, in hindsight,
(09:51):
is exactly the advice I would give someone today. Is.
Someone today said, what would prepare me to run a
company of the size of shop If I Shopify, you know,
is is almost a hundred billion dollar company depending on
what day you look. Um, So we were one of
the largest companies, certainly one of the largest tech companies
on the planet, but also one of the largest companies
on the planet. I would say that law school was
far more instructive, and it was far more valuable to
(10:14):
me than something like I also went to business did
a joint law and b A business school was not instructive,
was not helpful. It was all pedagogical, it was all
case studies. But law school taught me how to write.
It taught me how to think. It taught me how
to debate something as simple as being able to read,
you know, a thousand pages and pick up the one
single line that is the most important line. They call
it the ratio decidentity in in sort of Latin. But
(10:36):
that's the most important, that's the crux of the entire thing.
That is a skill that I never learned really up
until law school, and so it was really valuable for me. Well,
and we know so many stories of founders that don't
have that skill set who you know, uh, you know,
lost on a technicality or you know, signed a deal
or negotiated something but didn't do this type of review
(10:56):
for themselves ended up paying the price. So I imagine
when you know, join Shopify UM and in those early
early years and you know started you know, helping lead
the organization, I imagine that was a really valuable skill
set to bring to the co founders. And two, we
raise our first round of financing. It was a Series A.
It was led by Bessemer um by Jeremy Levine, who
(11:16):
is still on our board. Is one of the most
important people UM in my life. Professionally. He's just been
a huge mentor and he's been a great board member
for us. But we didn't have a CFO at that point,
and I think Toby and I sort of looked at
the docks and I think what law school gave me
was it didn't necessarily give me a playbook on how
to do a series A financing, but it gave me
the confidence that I would I'd be able to figure out, Okay,
(11:39):
what exactly is this? How do I what is a
liquidation preference? How do I look this up? How do
I how do I how do I explain it in
a way that makes makes sense, and so um that
I thought was really valuable, and the same sort of thing,
I mean, the things that we raised our series in
twenty ten. We took the company public um both in
New York and Toronto, dual listing in two thousand fifteen,
and now you know where we're six thousand people. One
(12:00):
of the things that I feel strongly about is that
a company like Shopify or any high growth company, the
people that are leading have to requalify for their job
every single year. And I think requalifying for your job
every single year puts the onus on you as the
individual that you just you gotta always be better. If
there is someone out there right now who's a better
CEO for Shopify, that person deserves the job. But I
(12:24):
I I want, I want the job, and I'm willing
to requalify for the job every year so that there's
no way there is a better candidate out there than me,
and the onus is on me to do than not
on Shopify, to sift through or to vet me. And
that's sort of what law school did for me, was
it gave me this um, this curiosity about exploring things
on a much deeper level. And uh, and that's it's
(12:45):
been instrumental. And so I know that I'm sort of
throwing shade a little bit of business school, but I
just especially in sort of a post COVID world, especially
when all these universities are going to a remote structure,
I simply don't think that I think you need to
go to university. You need to go to school to
take the skills out of it, not because you were
getting some sort of uh you know, some sort of
degree or piece of paper. I just that's just not
(13:05):
that valuable anymore. Really really appreciate you given us that
insight into the way that you think about this stuff.
And to your point, you know, it's pretty rare where
the founders and early operators of a of a startup
precede are the same guys around the time of the
Series B financing or C financing or the bigger later
stage financings. Let alone, once it's a publicly traded company
(13:26):
with you know, thousands and thousands of employees, I'm sure
that there's been some major growing pains. But you know,
talk us through that a little bit, because I'm sure
that you've learned a lot along the journey. Yeah, it's
what's cool about being in a place. So I'm I'm
thirty six years old. I think you're around my age,
maybe a couple of years younger older. So, um, I've
spent over ten years, over a decade a shop with that,
(13:46):
which which is, you know, like almost a third of
my life. And there's something about being at a particular
place for that long And one thing I think that
it does allow for is is really really high levels
of context. I mean, you've been you founded, but also
have been running Summit for I think a decade as well,
maybe more right, since she has eight you guys started
something like that. Well and and and that's the counterpoint.
(14:08):
I am still very involved in Summit, and I have
that cultural knowledge, but I am not the best guy
to operate, you know, a mountain development operation. So that's
that's why I'm so curious. Most of us who start
these companies don't have the same skill sets to operate
at scale um and that's something that gets lost. It's
like as these companies scale and you add you know,
you go from ten to fifty people, you lose culture,
(14:30):
let alone you know, fifty to five thousands, so to
have the founders in the positions. To have early leaders
in the positions that you guys have them certain has
a huge impact on the culture. So you're obviously right.
So in the context side one, it means that just
like you a summit um, I have a really really
great understanding of every aspect of Shopify, And that is
so right now. Shopify has you know, you know, over
(14:52):
six thousand people, we have over a million stores on
the platform. If you were to aggregate our stores just
in the US, for example, Shopify were not a retailer,
but if you pretend for a second that we are
a retailer, we would be the second largest online retailer
in America. There'd be Amazon and then Shopify, and then
like after that you'd see eBay and and best Buy
and home Depot and Walmart dot Com and all those.
(15:12):
But shopol is the second large zoneline retailer in aggregate.
And I think what comes with that is we have
a lot of different areas of our business. We have
a capital business. We've GETTN like over a billion dollars
withorth of cash advances. We have a payments business. We
have a logistics business of shipping business. We have a retail,
physical retail business, shopol point of sale, and and that's
just a slice of it. One of the benefits of
being at a place for a very long period of
(15:32):
time if you if you're curious about that place, and
you have a real um and you and and and
and and that place is something that you deeply care
about as as it is for me and it is
for you. With Summon, you do get a benefit in
that you sort of know exactly you're able to navigate
the company in a much more um in a much
better way, in a much more effective way. However, the
key to it, I think has always been you know
(15:54):
what our strengths are and know what our weaknesses are.
We like to hire people at Shopify for their strengths,
not their lack of weaknesses, which we've said publicly, and
that's something that is fairly well known. And so you
often have these like strength finder diagrams where you sort
of see they kind of look like stars almost like
people are very strong here but very weak in other places.
We're okay with people having weaknesses. In fact, in some
cases big weaknesses as long as our strengths are make
(16:17):
them really really unique. And so that's something we we
we use as a hiring metric or hiring a vector,
but we also think about it internally. I I am
actually not a very organized, not a detail oriented person.
I like the big picture, and so the people that
work with me, I need them to be incredibly detail
oriented because that's just not my skill set. On the
flip side, if there's a particular the business that I
(16:40):
simply don't think I have requalified to run UM. So
if you take any any area of our business at
the beginning, I'm an entrepreneur, I'm a founder. I'm a
startup guy. I love the early days and stuff, but
as particular perspective, I need to hand that off to
someone who's better suited for it. Um we we we um.
One of the things that I am most proud of
a Shoplin is building shop if I p us, which
is our our enterprise product, and we have you know,
(17:02):
everyone from from Kylie to Jim Shark to Bombs to
All Birds to like a ton of the biggest DTC
brands on the planet, all you Shopify plus UM. I
was totally the right person to get that started, but
at a particular point, running a two or three hundred,
you know, person effectively sales marketing and enterprise product division
wasn't for me. It's important. I think that leaders know
(17:24):
when they need to bring in someone else to to
help run that, and that that I think is just
self awareness. I think self awareness is probably the most
important thing of UM, at least for me, has been
the most important skill set to develop. Over time, we'll
be back with more out of the hustle after the break.
(17:48):
Like when I look at you know, the big sort
of incumbent power players and in the industry typically really
lack innovation. They can't really build like what's next, but
they can they can copy it really fast. So if
you look at like a Facebook and like, you know,
the best features on Snapchat are going to be on
Facebook as soon as they can do it right, or
on Instagram or whatever. And and you guys kept on succeeding,
(18:08):
you kept on growing. You were you're you're making money,
being experimental, being sort of front of the marketplace. I
want to know why talk to us a little bit
about that. I would love to understand what separated Shopify
to make it so this was the culture there. When
you sort of look through the review mirror, things do
a little bit things do look rosy, and certainly building
(18:29):
in an app store and a partner program, um you know,
a decade ago turned out turned out to be a
really great idea for a bunch of reasons that we
can get into um. But that actually came from a
very simple thing, a very simple decision, which is that
we did not want to build everything for everyone. We
wanted to create products that most people need most of
the time. And back in two thousands, ten or two eleven,
(18:50):
when really the partner program, we were just setting it up.
In the first place, we were building e commerce software
for small businesses that sold physical products online, and that
was it. And so if you needed us to convert
shoe sizes from American sizes to European sizes, yeah, maybe
that's something that you know, some people need some of
the time or some people need most of the time,
but that's not what most the most most people most
(19:11):
of the time don't need that. And so instead of
actually building out every feature under the sun, we said, well,
what if we did this. What if we said Shopify
is going to provide the use case, the product market
fit for eight percent of what everybody needs that wants
to sell physical products online in a small business context,
and what if we allowed third parties to build that
last what would happen? Well, the result of it is
(19:33):
that one these third parties can now build something and
they can make real money, they can create We can
create more value for them than we capture for ourselves.
I've said this a bunch of times publicly, but you
know there's sort of that that famous Bill Gates line,
which is you know, you've built a platform where you're
able to create more value for the platform for the
third parties and you capture for yourself. I mean Shopify,
(19:53):
you know last year did a billion and a half dollars,
but the ecosystem made close to six billion dollars last year.
And some of the are big companies, but a lot
of them are you know, two three single person shops
that just build apps for Shopify. So we've always sort
of took a bit of a more platform approach to
to building software and and and to building the product.
And now the result of it is that no matter
(20:15):
what your your use cases, you can get just about
product market fit on Shopify, regardless of what are the
particular nuances of your business, because our eight percent gives
you coverage, but the other really customizes it for you.
And then as we sort of continued, it became clear
that Grand two thousand thirteen that Okay, we're not really
in the e commerce business. We're actually the commerce business.
(20:37):
And then you have to sort of think, Okay, what
does the future of commerce look like? Is the future
of commerce going to be some omni channel It's gonna
be uh, some sort of um, you know, combination of
online and offline. Our view was no, actually, it's not
going to be that the future of commerce is gonna
be retail everywhere that in the future, unlike the past,
the consumer is gonna dictate to the retailer, the brand,
(20:58):
or the or the business how they want to purchase.
And if a consumer says I want to buy on
Facebook or Instagram, that's the way you have to sell it.
And if the consumers is I want to buy offline
and physical beautiful you know, downtown boutique, that's we have
to sell it. And it might be online and it
maybe on Pinterest or house or wherever and so around too.
Doesn't thirteen are objective change from building beside this sort
(21:20):
of being the best e commerce software for small businesses
to really just being commerce software, and we began to
sort of use the term retail operating system that what
if we were the world's first retail operating system. And
then around two fift and camera and sort of pre
i PO, something else happened, which is dramatic, which was
that some of those businesses that started on Shopify at
(21:42):
their mom's kitchen table, very very small businesses. In some
cases they grew to be category leaders. They grew to
be the the They were no longer the insurgents. They
became the incumbents. And give us, give us some examples. Yeah,
this is sort of Jim Shark movement watches um. These
type of businesses that simply almost overnight became truly leaders.
(22:03):
Um and all birds and bombs didn't come to a
little bit later, Tommy John. Some of these businesses got
really really big on Shopify, really really quickly. And the
interesting part there, the the insight was if you think
about software as an industry generally, what you tend to
see is this if you just take some like email marketing,
when you sort of the pro sumer starts using the
BCC line in in email, and then that prosumer becomes
(22:26):
a small business, a very small business, a micro business,
and they maybe start using something like male Chimp, or
they start using constant Contact. Eventually they may upgrade to
exact target, and eventually they may use they may use
some sort of like Oracle version of that UM. But
there tends to be a transition or a graduation in
software as you get bigger. What we encountered sort of
pre I p o um Or in fourteen was that
(22:48):
the businesses that had been starting on Shopify, they were
growing really really big and they were not leaving the platform.
And so again there was a new thing to think about.
There was a new um, a new piece of insight,
which is, wait a second, maybe we're not just e
commerce software or commerce software, and maybe we're not just
for small businesses, but maybe actually larger companies can use
as well. And that really was the formation of Shopify
(23:08):
plus and and and shopy plus was really just created
as a place for the most successful businesses to graduate
two as they got really really big and and and
and that was happening. But then something else happened, which
is that a bunch of really large companies, whether it's
you know, brands like Yeasy or was Procturing Gambler or
Unilever and Nestle or Heinz, ketchup Um or Nutrogena. They
(23:30):
began to come to shopify Plus and say, hey, look,
we don't want a six month sales cycle. We don't
want to spend fifteen million dollars. We just want to
get something up right away that's super scalable, that's super beautiful,
and we want to have modern technology. And so Shopify
Plus became a landing pad for a lot of those companies.
And some of them actually, uh, you know when I
met Blake from Tom Shoes at at a summit and
(23:52):
and what Blake said to me was and funny enough,
Andy from from UM from Manobos also the same thing.
That these were sort of version one or sort of
the first era, the first gen of DTC brands, and
Blake had no choice but to build custom software, so
did so did Bonobo's UM. But what was happening was
Auntie dozen fifteen. These companies are like, why do I
(24:13):
have three engineers when I can gc Shopify Plus and
actually talk. So Tom Shoes that came over, and Rebecca
Minkoff came over, and Steve Madden came over, Nicole Miller,
And so that's a long answer to very short question.
But that sort of does paint the picture of why
I think we've been able to innovate is because we
just were always questioning past assumptions. Are we really e commerce?
What is commerce? Are we really small business? What a
(24:35):
small businesses look like? And I think we've been able
to do a pretty good job of staying ahead. Um,
lots more to do, but that's sort of how we
look at the world. You mentioned Blake, you mentioned Andy
at Bonobos, like, these are companies that specialize in shoes
and pants, not technology. So here we are like they
they have to now make that jump to the next
level of their software to empower their business, and they
(24:57):
certainly aren't going to do it in the house, and
if they do, it's going to slow them down tremendously.
Whereas with you guys, it sounds like you. The reason
that you kept on innovating, the reason you kept on
adding these partner programs and projects and you know support
system that ecosystem approach is because um, this is the
life cycle of I just never knew that. That's amazing. Well,
I mean, I think the contract we have with like
not not the legal contract. But but but actually the um
(25:20):
the agreement we have with our merchants, these million stores
is that when you hear something that comes out in commerce,
whether it's Facebook announcing shops, or it's Pinterests adding Bible pins,
or it's Instagram doing um, you know, direct purchase UM
right on Instagram, Uh that day you If you're on Shopify,
we have a responsive and make sure that you're able
(25:42):
to use that technology that but by by choosing Shopify,
you will always ensure you have the most modern version
of whatever commerce is, whether that's Apple Pay or Shopify pay,
or it's Android pay or for for the accelerated checkout,
or it's cross posting on different marketplaces or cross posts.
I mean we just didn't. I announced the deal couple
WEE with Walmart because Walmart dot com is now a
lot of congartulation, which is really cool. Now, most of
(26:04):
the stores on shop if I don't necessarily want or
need to sell on Walmart dot com, but there are
thousands of stores that absolutely would love to cross sell
their products UM and and and and their brands on
on Walmart dot com. And so five years ago or
ten years ago that would have to be flying them
flying out to Bednville, Arkansas and meeting a retail buyer.
Now they don't have to do that. Now they're using
by being on Shopify, through the Shopify dashboard, the admin,
(26:26):
they can simply activate that channel and and and and
get UM hopefully get approved to to cross sell. So
that's the covenant we have with them where which is
I think why you've seen so many folks come over
to us UM and we wear that responsibility really heavily.
That that that's that is what I think is is
is what makes us a good company. But it also
means that it also there's a great deal responsibility when
(26:48):
you take that on. And I think that's the reason
why some of the biggest brands on the planet trust us.
Shifting Gears here a little bit to talk a little
bit more about you and a little bit more about you, know,
your style, leadership and both person only and professionally. I'm
sure it's felt inside your company as it is outside.
But like you're such a humble dude. You and Tobias
are like so kind, so nice, so generous, Like in
(27:10):
all your conversations, one would forget that you're running you know,
a hundred thirty billion dollar company with six thousand employees.
And I want to know, like, you know, do you
have like a daily practice, are you meditating? Like how?
And has this been has this been an active pursuit
for you guys to not let you know the success
of this go to your head or is it just
(27:32):
sort of your personalities? I mean, I think building a
company like Shopify in Canada, Um, I just I gotta
spend a moment on sort of geography because I think, um, again,
I sort of had a taste of both worlds. You know,
born in Canada, but I sort of feel like I
spent my formutive years in the US and Canada to
me is is Canada sort of like America for Europeans.
(27:52):
Is kind of the best way that I can put
I know, you spent some time up here in Toronto,
out of places, but um, there is a little bit
of um. One of the best parts of Anada is
sort of this this modesty that is just in the
air that it is not cool to be boastful, it
is not cool to uh to kind of lose yourself
in your own ego. UM. And I think now, by
the way, that's not always a good thing either. Um.
(28:12):
Sometimes Canadians generally are are overly humble. They don't you know,
our Prime Minister Um talks about that candidates more swagger.
I think that's right. I think we do need more swagger. Um.
You know, if I ask your name five tech companies
from Canada, you can name Shopify and maybe you'd say
something like Nortell or BlackBerry, which are both really not
not around anymore. UM. We tend to be on the
acquiring side of the of the book, not the acquirers,
(28:35):
which is because I think there's a little bit of
an inferiority inferiority complex that exists up here. UM. But
I didn't grow up here and so I have less
of that, and Toby grew up in Germany so he
is less of that also. But in terms of you know,
keeping uh, keeping our focus, I think the best thing
that that certainly Toby and I would both agree on
is um are our our partners, are our our our wives,
(28:55):
UM our life partners. Have been incredibly instrumental in that
because I've been with Lindsay since well before Shopify, and
and Toby has been Fiona for for this the same
the same thing. So there's a little bit of of
there are people around us that holds accountable. There are
some people that call us out on our our our
bullshit when when that exists, UM, similar to you. I
know you have a similar dynamic. But my best friends
today are still the best friends that I had when
(29:16):
I was a kid. Um. And and no matter you know,
how well I'm doing or how well the company is doing,
they're still gonna call me out of my on my stuff. UM.
But we've also, you know, Toby and I started seeing
a coach back in two thousand and eleven, or I
would say, um on on a recommendation of a of
a mutual friend, and um. We ended up loving coaching
so much that we ended up hiring the coach full time.
(29:37):
His name is Cam and then he came into the
Shopify and we asked him build a coaching practice. And
so there are sixteen or so full time coaches UM
staff at Shopify. And we actually we had a coach
on staff before we had a CMO, I think even
before we had a CFO potentially. So that sort of
performance management, growth, leadership growth thing is sort of embedded
in our culture, but it's just it's not the type
(29:58):
of place where you know, walking around um, like you know,
with with with a big head and walking around the
modest gets you very far. In fact, I think the
anti antibodies that Shopify sort of reject those things. They
sort of push you out and and we we don't
necessarily um people have come into our company that have
had ridiculously impressive backgrounds and cvs and have built huge
(30:18):
companies and made tons of money. And it doesn't always
work out because sometimes they simply, um, they they don't
come in as with the right curiosity, they don't come
in as an anthropologist who kind of needs to look
at Shopify and understand it before they can have an impact.
And then on the sort of you know, mental health
side of things, um, you know, frankly, it's it's been
tough for me. I'm a you know, Tim Ferris calls
me a power extrovert, and I think that's probably accurate.
(30:40):
I I love being around people. That's where I get
my energy. On a on almost every Friday night you
can have you can find my wife and I hosting
you know, shove at dinners at our at our home
with tons and tons of friends, and and that's just
kind of how we've always lived, and it's been I've
had anxiety since I was a kid. I feel like
my anxiety has been accelerated far more than sort of
co bit hit and and I've just sort of been
(31:02):
doubling down with things that keep me grounded. And probably
the most important thing other than just a daily ten
minute uh inside tim er mindfulness practice has been time
with the kids. UM. And I have two daughters, Bailey's
four and Zolway's one and a half. And and I've
I've rescheduled my life and so I start my day,
you know, walking the dog with the girls. I finished
(31:22):
my day walking with the whole family. UM. I've tried
to be very intentional about how to kind of make
this all work, because the truth is, I've been really lonely.
I've been more lonely in the last three months. And
I have you know, any any time I can remember. UM.
But I'm also talking. I mean the reason that I'm
I'm I'm okay with talking about it on on on
on your podcast, if is that I think it's important
that we all kind of share not just the highlight
(31:43):
reels of what's going on, but also those tough days. UM,
because I think there's a little bit of bravado that happens,
particularly in tech Um and it's a little bit easier
to be outside of the valley and outside of the States,
but there's a bit of bravado that happens um and
not every day I'm feeling my best um. So yeah,
that's that's kind of how we do it. And I
think the other thing is, you know, taking you back
(32:03):
to Summit for a second. One of the reasons that
I went to Summit was surround myself with people that
were better, smarter, faster than I was. And that's what
Summit did for me for for many many years. It
allowed me to sit at a table and meet asked
so like, you know, who are you, what do you do?
I'm chef, You're the supermantion. Yes, Like, just having conversations
like that are just so mind blowing. I remember I
(32:26):
remember meeting Robin Arson at at one of someone that
sees before Peloton had blown up, and just hearing her
story her transition from law into you know, like basically
helping to curate a curriculum for this small company called
called Peloton that I think is so valuable and I
think a lot of us, despite my saying that my
best friends are so most the best friends since I
was a kid. My network, the people that I I
(32:48):
speak to on a daily basis sort of these mentors
in my life. Um. One of them is the best
father I've ever met, and I want to emulate the
way he is a father. He's actually not very good
at many other things, which he would admit to, but
he's just the world's greatest dad. I have another friend
who just really understands, like, really family dynamics really well,
particularly when you know when when money is involved, and
and I really want to emulate the way he structured
(33:10):
his family. And another one it's just the most amazing, um,
you know, philanthropist and loves to give his time and
his money to charities and make a real impact. And
so I've been able to curate a group of sort
of mentors that I kind of swapped in and out
depending on what I'm focused on, who are so much
better than I am at those things, and um, and
that really helps. I had a friend who gave me this,
this piece of advice, and he was a very successful
(33:32):
real estate developer and he had retired in his late
thirties to spend time with his family and his friends,
and he got presented this amazing opportunity to do this
development that he had dreamed of. And so he was
coming back out of retirement and like raised more money
and was like building the team and getting excited, and uh,
his wife pulled him aside and was just like, hey man,
just so you know, no one that you love the
(33:54):
most or that loves you the most, will care or
will love you anymore or less based on your success
or failure of this venture, right, and so having people
in your life that aren't measuring you by that yardstick
is just like so important. And I think for you guys,
I don't even know if you ever like, you know,
built that. A lot of us just have that, you
know around us, you know, and you desire it. At
(34:14):
least I did. I. I had, you know, an ego.
I wanted to feel special or valuable or successful or
any of those they are looked at that way, you know,
in my in my twenties of course. And so that's
that's a that's a tough thing, right, Like it it's tough.
And and you know, I, uh, I grew up with
two very loving parents, parents that also believe I can
do anything. And I'm not sure coddling is the right word,
(34:36):
but I was sort of always I was, you know,
I was really lucky that I had very supportive people
around me. The problem was, um, like most of us
when you know, in my in my early twenties, I
kind of thought I knew what I was doing. I
kind of thought when I built this T shirt business,
I made a little bit of money, and I did
this other thing, and I made some you know, I
got to law school and I did all these things,
and it was really cool. That's the value of surrounding
yourself with people that are truly better than you in
(34:57):
in in a whole bunch of different categories, because you
begin to it's like, you know, it's we use it.
We use the metaphor of boxes at Shopify that um
the sort of a series of box. At the bottom
of every box, you're shaky, you're uncertain, things are not
necessarily um, you're not confident. And then eventually get to
the top of that next box, that box, and that's
where you start. You begin to get that swagger. You
begin to get confident, maybe even cocky. If you have
(35:19):
people around either reach their hand down and then bring
you into that next box, even though the bottom of
the next box you're going to be incredibly shaky. That
is super valuable. And UM, I think that is the
value of having, you know, a tribe or a community
around you to kind of help you with with that process.
But I gotta tell you, like I, UM, my biggest
challenge when I first joined Shopify wasn't the work. It
(35:40):
wasn't the company. It was myself. It was that I
didn't I I didn't I wasn't self aware. I didn't
necessarily have this insatiable growth mentality or this curiosity. I
felt like whatever I had done, UM, I was able
to you know, I was. I was proud of that,
but I thought that that mattered. UM And I didn't
certainly did not have this idea that I'm gonna have
to read qualify for the things that I currently have
(36:02):
professionally every single year. UM. And I gotta tell you,
I'm a lot happier now, I'm a lot more mindful now.
My relationships are richer now, and I'm I'm just I'm
I'm happy. I'm a better human being now than I
was then. And and the way it manifested itself was
in the early days, remember not wanting to hire anyone
better than me because I thought that if I hired
something better than me, uh, it meant that I was
(36:23):
less valuable or less valued. And it just that's the
furthest thing from the truth. Now, like everyone who I've
hired is so much better than me, and that makes
me better and that makes me very proud. The journey
has been great. Art of the hustle will be right
back after this short break. I'm curious, you know, for you, now,
(36:48):
what do you still do too much of? It's a
good question. Um, I think I probably spend uh too much.
So it's funny if you sort of think about like
work as being kind of three different UM categories, sort
of um in the weeds, um kind of the middle work,
and then sort of up top is kind of the
large strategy stuff. I tend to kind of operate in
(37:08):
either the bottom or the top. I tend not to
do the middle stuff UM, and I probably should be
a little more balanced, But I do get into the
weeds sometimes and things that I just I just I
care a lot about. Um. There are particular areas of
Shopify that I'm so um. Maybe two to the detriment
of the group and that made a detriment of me.
I'm overly attached to and I need folks to basically say, hey,
(37:29):
look I got this. Uh. And it's not to say
like I know that's a sort of a tip prototypical
you know thing where I'm too I'm too focused, none
of that crap. I just sometimes I get too far
into the weeds on something that I sort of forget
the bigger picture. And UM, that's sort of where UM
curating my calendar in a way that actually allows me
to have the highest impact that I think is is
(37:50):
really important. But one thing that I did do UM,
I brought some more things in my life that I
just are just fun for me. UM. I still take
calls with certain merchants that are thinking of migrating over
or that are thinking of launching on Shopify, because what
I realized was there are certain things I just I
don't need to be involved in everything, because there's no
way to run a company at our scale if you're
If you're involved in too many things, I become a bottleneck.
I never want to be a bottleneck. But there are
(38:11):
something that are fun for me and the things that
are and I believe that, Um, I believe that we
all need to kind of figure out what those things are.
For you. Maybe it's something as simple as the music
at an event for summit. And you may be like,
I know, we have like the greatest music producers like
on on retainer on standby, like the most famous you know,
I think you guys basically like quest Love on retainer
at some which is amazing. But sometimes I bet you so,
(38:34):
you know, I like, let let Jeff just deal with
this because I just want to do this. I think
it's important to remain to have some fun and um
and not lose that sense of of of fun and
and so I allow myself, um, the opportunity or or
the freedom to kind of get into the weeds sometimes,
but I think I probably do it too much. My
worry is, like there's the funny the podcast called The
(38:56):
Art of the Hustle, and that is such like a
you know, twenties mentality from me right where it's like
you hustle, hustle, hustle in terms of like the the
language that we're that we're using to describe it. And
and there's a limitation to what that can get you, right,
and then you have to gain wisdom not from your experiences,
but ideally from reflection. And I have an issue where
(39:17):
I'll just end up scheduling my days so packed so
repeatedly and not really save time for reflection when I'm
in like a work mindset. And so that's what I'm
trying to get more of for myself. Then that leads
me to my next question for you. You know, I
want to know what do you want more of right now? Yeah?
I am, I'm fairly type A UM and I find
(39:38):
and I'm sort of incredibly goal oriented. I'm I'm trying
to look for things right now that I actually can
just um can just be at so UM. I started
running two years ago. I always want to run, never
figured out a way to run it, just I was
always sore, like I would. I can cycle for you know,
hundred and two hundred k, but I was never able
to run. So I got a coach and began to
(39:59):
sort of in going about running and running technique. And
then of course that always leads to the uh the
next stage, which is, okay, when are we gonna run
a half marathon? Or when are we gonna run a marathon?
It just like I feel like I'm always in conversations
with sort of my running group about that particular thing.
And I actually decided to um to sit out and said, hey,
I'm not going to run a half marathon. I don't
(40:20):
want to run a marathon. I just want to enjoy
going for a run. You know. I bought the garment watch,
and I made sure that I was tracking everything on Strava,
and I, you know, I was, I was being a
really good type a entrepreneur, and I just started enjoying
it less um or or you know, the same thing
with cooking. I got really into cooking a couple of
years ago. My wife as a food entrepreneur. She also,
you know, is a has been a fairly well known
(40:42):
blogger and the Canadian food scene for a long time.
And so I was like, you know, I'm gonna cook.
And then it was a matter of like, I'm gonna cook,
and I'm gonna I'm gonna play it in a particular
way that just looks so amazing and and and I
stopped enjoying so in the same way that I stopped
enjoying running once I started to think about the marathon
or half marathon, I stopped doing cooking when I sort
of felt that I'm doing it for the destination, and
(41:02):
some things, I just want to enjoy the journey. And
I know that sounds, you know, cliche, but some things
like I just want to go out for a run
sometimes and if I run for ten minutes or thirty minutes, uh,
they listen to music or a podcast, whatever it is.
I just want to enjoy that. And um, I'm not
necessarily I'm not good at that. I'm actually really bad
at that. Um. And so I'm intentionally now saying I'm
gonna cook and like, if it looks great, whatever. If
(41:24):
it doesn't look great, that's okay too. It'll be delicious,
and I'm going to enjoy the process and my family
is gonna absolutely love it. Being more mindful about that stuff,
I think is really important. And because everything in my
life is basically quantified, whether it's you know, the stuff
and doing at the office, or it's the stuff that
I'm doing, you know, on on sort of the the
investment side or on the on the philanthropic side, it's
(41:45):
all quantifiable. I want to have some stuff that is
a little bit more um right brained in my life.
And and so I'm really struggling to kind of pull
back from some of those things as much as possible.
But one thing I don't want to say, just coming
on the previous comedy made around sort of the art
of the hust soul, is this. Have you actually scrolled
back through my timeline for like three hours and you
get to like two thousand thirteen, you're gonna you would
(42:07):
see basicuteen two dozen eleven. It doesn't thirteen. Almost every
single tweet that I had ended with hashtag hustle. It's
sort of a It was a personal philosophy for me.
Um I had learned it from from from Gary v
and and and and um I'd spent some time understanding
his philosophy around you know, perseverance and just you know,
running through walls at all costs. And it was just
(42:28):
it was an interesting kind of life philosophy for me.
And actually Tina Eisenberg Swiss Smiths, who has a great
company called Tatley Check, she made me as a gift
after sort of seeing this all um all emerge Um.
She made me a gift business cards that that also
doubled as a temporary tattoo that said hashtag hustle and
and and um and yeah and and and so I
just I probably gave out those business cards at a
(42:49):
bunch of summits UM and and at some point it
became sort of UM synonymous with Harley at least a
Shopify that you know, Harley was kind of this hashtag
hustle guy. And one of the as I realized was
people began to misinterpret it, and I actually realized that
what was happening was UM. People interpreted hashtag hustle as
this kind of strange UM work hard mentality. They they
(43:14):
there was no there was no room for nuanced, there
was no room for optimization. It was if you have
to get something done and it's gonna take a hundred
phone calls, you do the hunter phone calls. And actually
that's never what I meant. What I meant by it
was you actually figure out who are the three people
who are most likely going to lead to UM an
affirmative answer or or or a yes in the other line,
and you call those three people. And so funny enough,
(43:36):
I'm glad you're you're you're thinking about sort of the
history of the term, because at shopify, I actually it
became UM. It became something that I actually regretted introduced
with the company, and so at some point I almost
had a funeral for it at the company. I did, uh.
I gave it's hawk at a town hall and I said,
I'm actually retiring hashtag hustle because it's been it's been misinterpreted,
and it's not really just about working hard. It's also
(43:57):
about working smart. It's about being strategic Western things. It's
about um, you know, finding hacks and finding ways to
kind of skip the queue and and um so I'm
just I thought that was an interesting kind of segue.
And what got you here won't get you there. It's funny.
I'm sitting here at my desk in my office talking
to you about it. And I have a momento more
eye skull sculpture that says, never put off tomorrow what
(44:17):
you can do today, And it's the only words they're
looking at me on my desk, and so here I
am being like, yeah, man, you know, I really want
more reflection. But the the the mementos, the totems that
I have around me are still towards the temple of
the hustle, you know what. And I actually I changed
the artifacts in the in my office around on video now.
But if you were to see in my office here
I'm at my house. My artifacts changed from like you know,
(44:40):
I had like a Morgan Stanley made like the skateboard,
uh sort of deal tombs and we did a fund
raise um post I p O and they made me
sort of the deal tombstone was actually a skateboard because
they know I skateboarded. And actually I used to have
that up my office and I'd actually changed it now,
um with with actually pictures that my kids have made
for me. So like these are like crayon drawings, and honestly,
it makes me so much happier to have those in
(45:01):
my office. Is my backdrop than something like these sort
of three hundred million dollar deal tombstones. Um. So hey,
look I'm I'm going through what you're going through also,
which is that I think we're all trying to figure
out what how we operate in this new world, how
we find time for mindfulness and how we find time
for just being. But it's difficult because you know, to
your point, what got you here won't get you there.
(45:21):
What got us here is it's very much in our firm,
where it's it's you know, it's it's our Um, it's
not our prefrontal cortex working, it's our amygdala working. In
many cases, it's our lizard brain. And for a lot
of entrepreneurs that are listening to it, our lizard brain
is the reason that we got here, and not not entirely,
but some parts of it our desire, our ambition, our
work ethic And so it's very difficult to get to
(45:42):
a particular point and say, Okay, now I'm gonna stop. Now,
I really want to just double down on my mindfulness
practice in my yoga, and I want to make sure
that I i you know, I'm able to be artsy,
and I want to be able to live in the moment.
And it's just really difficult because we've been sort of
you know, we've we've had hundreds of years of of
of of breeding on this. But so for those entrepreneurs,
at some point you were doing everything yourself, and so
(46:03):
at some point just deciding you're not gonna do everything yourself,
you're gonna get out of the details of the weeds.
It's just not an easy thing to do sometimes. Thank
you for the time, Harley. I love you. You're incredible.
You're such an amazing dude. You're such a like, great,
great person and clearly just like it. For me, it's
like you said, you know, coming to summit and getting
to meet people that are brilliant and wonderful people and
(46:25):
wonderful entrepreneurs and you know, learning from them, you know,
like you I was, you know, as a decade ago.
So I was in my early twenties, which means by
definition you pretty much don't know ship and you know it.
For for me and for my partners, to see what
you guys have been able to do and how you
carry yourselves and what you value has been really inspiring
(46:46):
and really impactful for us. So thanks again for being
on the podcast, Thanks everyone for listening, and Harley Man
keep rocking, dude. Oh thanks Jeff. Appreciated For more podcasts
(47:13):
for my Heart Radio, visit the I Heart Radio app,
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