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one of the greatest hacks for being an ambitious hard driving entrepreneur and
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that's why it's Kylie Jenner is nothing short of burlesque Harley Finkelstein he's the president of Shopify one of the
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largest e-commerce platforms worth over 60 billion dollars he's helped scale brands worldwide and he's now on a
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mission to help you start your own business about a month into college I got a call from my mom and said Dad's
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been arrested and he's going to jail college is over and I was shifted into this survival mode I had no choice and
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it's a very powerful driver I met Toby around that time the initial idea had lots of other competitors this was not
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this massive novel thing we just did it better and that was how shot that was born there's a perception that entrepreneurship is very expensive
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that's not true it's less than a couple Starbucks coffees to go start a business today there's so far too many people that work at a job they absolutely hate
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because they think they have no choice no one had this massive 80-page business plan and then got started that's not how
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businesses are created they're created based on this nugget of an idea and they're explored and you get curious about you try this other stuff and
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that's how you build companies that changed the world I wake up every morning encouraging more entrepreneurship creating tools that
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help entrepreneurs start scale and build faster that drives me to keep building and keep growing the stores that we are
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most proud of are the Homegrown success stories that grew to be multi-billion dollar businesses if I give you three million dollars who would you invest it
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in I would definitely put one of those millions of dollars into the hands of a Creator who's the second one I think
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would be the third one would be someone oh really yeah those are the types of people that I would back
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would you like to go for dinner with me and my guests here on the diver CEO we are holding dinner parties all around
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the world over the coming months and our subscribers on this YouTube channel are invited we're inviting 20 subscribers to
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every dinner so if you'd like to come for dinner with me and my guests here on the diver CEO I have a favor to ask you
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all you've got to do is hit the Subscribe button and I hope to see you at dinner somewhere around the world
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very soon [Music]
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Polly in your own words who are you what do you do and what
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mission are you on I've always self-identified as an entrepreneur full stop
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um that's kind of the tool that I use to solve every problem in my life and to have fun is always through the lens of
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Entrepreneurship what do I do um I mean I think technically I'm the
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president of Shopify but I view my role as being the chief Storyteller how can I get the world to know that Shopify is
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the entrepreneurship company and invite more people to participate in that the mission that I'm on this is going to sound really repetitive now but is I
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want more people to try their hand at this thing that that I call business creation or entrepreneurship and I don't
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think right now most people consider entrepreneurship as a thing that they can do to self-actualize
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why does it matter if they if more people become entrepreneurs I think the world is far more colorful
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and I think humans are far more interesting when they commercialize their hobby for example I
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think there's still far too many people that work at a job they absolutely hate in fact I would say that they loathe because they think they have no choice
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and that was the case for a long time you go back 40 years 50 years not everyone could be an entrepreneur
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that is different and I'm not saying that everyone that has a great hobby should commercialize it hobby some Hobbies should stay Hobbies but there
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are a ton of people who work at a job they they despise they go home at night they go to the garage or their workshop
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or their kitchen table and they Tinker on cool stuff but they don't share that with the world
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if they did that consumers would get really better stuff that they can purchase and they can use but those particular people behind those
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businesses can find their life's work and this concept of life's work is not something
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that my parents my grandparents my great-grandparents even had in their lexicon but I think the idea of finding
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your life's work I think you have done that Steve and I hope that I've done that too that is a life-changing moment there's
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there's going to be potentially millions of people listening to this now that resonate with what you're saying they
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are in situations that are not serving them on some kind of psychological fulfillment level
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um why aren't those people in your view pursuing what their life work is I'm
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trying to like create some I guess some Nuance or trying to step into their mindset so that they feel understood
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what is the the the Gap the Grand Canyon that they need to cross in their mind to get to that
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other side which is their life's work why don't people do it I think a big part of it is perception I
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think a lot of people perceive entrepreneurship as something that's Out Of Reach for usually one of
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two reasons the first reason is is financial they have a family member or a friend or
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they've heard an anecdote of someone who started a business that was not successful and ultimately it cost them
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their entire life they couldn't you know they lost their house they couldn't put food on their table and so there's a perception that entrepreneurship is very
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expensive if you don't have money you cannot start and actually I would say that for vast majority of the time that
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entrepreneurship or business has been available in the world which is you know entrepreneurship business is about as
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old as currency so thousands and thousands of years the main ingredient in starting a business was capital and if you didn't
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have Capital you couldn't start and I think that's changed and we can get back to that in a second the second part is
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the understanding or the experience or the know-how to begin and I think that also has changed I think now you don't
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have to go to business school you don't have to you know have have grown up in a in a home with entrepreneurs to start a
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business I think that anyone can start and so on both those things I think the cost of failure is as close to zeros has
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ever been right now like as we sit here and the second part is I think that if you try something that doesn't work you
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can try it again and that may be you know your gym shark your aloe yoga
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you're James purse from a psychological perspective some people you know they often say well you
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know it requires a lot of self-belief they talk about self-belief and confidence as being this kind of macro
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force that drives people to to start and I was sat here the other day with an entrepreneur who's built multiple companies and been very very successful
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and he was saying to me he said something to me like when the it's actually pain the pain of his
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current situation which drove him to take the leap as it relates to people's
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like psychology and their self-belief and their self-confidence um when you're trying to get people to
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become entrepreneurs what can we do there to get them to take the leap is there anything that can be done I mean
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first of all I think that there's two types of catalysts for starting a business one is passion and the other is
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disparity or being desperate and actually I think entrepreneurs by necessity are a big part of the the
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greatest companies ever been created the reason I became an entrepreneur I mean I I told you that as a kid but but when I
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really became an entrepreneur it was because I had no choice and it's a very powerful driver it wasn't about my self-confidence or my
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Swagger whether or not I thought I could I had no choice in terms of you know you had Richard Branson on he has this
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famous line scroo just do it I think that plays in sort of the passion side of things not necessarily
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in the disparity kind of things I didn't say screw just do it I was like I have no choice what am I gonna do right now
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either have to like move back home to South Florida and live at home with my mom and my mom
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and sister's dad wasn't around or I can actually figure this out on my own and I can pay for school and I can help
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support my family and so it wasn't about scroo just do it that like it wasn't about self-confidence it was here's a way for me to actually survive
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and that thing that matters the role of passion in entrepreneurship you know you'll you'll know that a lot of
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entrepreneurs they are so um in love with the idea of being rich and
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successful that they'll kind of try and reverse engineer a passion into this their Journey being rich and successful
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so they'll sit down and say what do I think is going to make me Rich and successful this happens all the time you know entrepreneurs will come up to me
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and say I've got three ideas and they'll name three random things I'm gonna start a hair care business I might do a coffee
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company or I might do crypto for example and you look at that and go like it's gonna get so difficult for you in year
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one you're gonna quit all of these things what role do you think passion plays an eventual success I think you
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have to actually like the thing you're doing to do it over a long period of time my my first when I was 13 years old
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um I grew up in Montreal I'm Jewish I went to a lot of bar in bar mitzvahs that thing you do and you know 13 year
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old kids uh 12 years old if you're a girl 13 years old if you're a boy you go to these Bar Mitzvah parties and I
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remember seeing the DJs at these parties on stage playing I don't know cheesy
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music very cheesy music but I was just enthralled with them I thought they were the coolest people in the world because in a matter of minutes they would take a
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group of 300 sleepy people eating rubber chicken dinner and like a minute later a
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couple days later they'd be doing the conga lion and it looked like magic to me and I really thought that would be super cool for me to partake in and so
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there was a passion for me to I want to be a DJ turned out nobody would hire me because I wasn't
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really a DJ I didn't know how to DJ and I looked like I was eight years old I mean I've always been a little bit short
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I'm so short but I looked I was really sure when I was 13. and so there was no way anyone would hire me and I decided I
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would just start my own DJ company and hire myself so there's some passion to it when I was
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17 years old and I moved from we moved to South Florida when I was around that time moved back to Montreal when I was
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17 to go to McGill University my dad was no longer around we can get into that if you want to but I at that point it
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wasn't like I'm gonna go back to DJing it was okay things are really bad right now like dad's not around I have too
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much younger sisters mom needs help what am I gonna do and I started selling T-shirts to universities across Canada
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I had very little passion towards t-shirts I like wearing t-shirts as we talked about earlier like black t-shirts
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are something that I like but I was not a passionate t-shirt entrepreneur manufacturer I was passionate about
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survival I was passionate about supporting my mom and my sisters and so I don't think that t-shirt business was
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going to be something that I would I was going to be doing the rest of my life that was not my life's work
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fast forward until today leading Shopify with with our team I'm very passionate
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with shopify's Mission this idea that more people can be entrepreneurs because of the work we do at Shopify I can do
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this the rest of my life if if the board will have me um so I think there's a time and a place
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for passion in these things but I don't think it's the only reason to start you referenced a few things there that I
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thought were quite interesting and that made my mind wander onto um adjacent subject matter one of those is
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that you're talking there about what's driving us at different moments in our life one of the um conversations I had
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on this podcast with Barbara Cochrane the shark over here in the US uh she said to me that her best investments she
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makes in entrepreneurs they tend to have some kind of underlying trauma
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and and that ends up being fuel in their engine so when things get
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really really hard they're driven and in such an obsessive way and I remember then listening and I've always thought this I've always thought that insecurity
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and shame and these kinds of things are unbelievably unappreciated drivers and people For
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Better or For Worse it comes with a downside um do you think entrepreneurs should and
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Founders should go to therapy uh I think some should I think entrepreneurs and Founders need to be
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self-aware I think that that's the first thing once they're self-aware and they understand hey there are some things
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that going on in my mind in my personality in my whatever my my being I don't know how to describe it that I
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need to work on I think therapy is a hack to get there faster you can do it on your own and some people do some
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people do it through books and they did through meditation and they go do you know Ayahuasca in a in a desert somewhere but
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I think if you have if you have the means to go to therapy how could you not there is someone whose
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job it is to make you better now I think a lot of people make a mistake where they go to see one therapists they're
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like this doesn't work for me yeah and they're like therapy doesn't work no that therapist didn't work if you date
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somebody and the relation doesn't work doesn't mean you're never gonna date again it means I was the wrong person for you and so one thing I think about is whether it's coaching or it's mentors
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or it's something like a therapist or a psychologist in your life or psychiatrist you need to find the right fit but if
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you have the means to do so it just it's the greatest hack ever to just know more
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to realize more is it going to be painful unequivocally the joke that I have with with my therapist is I know
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it's been a good session if I feel worse after than when I did coming in because as I come into these sessions and I got
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Swagger and I just had a great day and things are going oh things are going my way then an hour later I leave and I'm
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like oh my God I'm still like I'm still such a work in progress you know one but
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but that's I think what we're all choosing here there's this great my favorite poem or speech ever is this
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Teddy Roosevelt speech the man in the arena did you know it no I'm gonna butcher it but it's effective
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like it is not the critic that counts but the the man or the woman or the human in the arena that matters and the
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reason I love that speech so much is because if you don't want any of the stuff you like you can you can be a
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Critic you can be a spectator but if you're an entrepreneur or you're you're a doer or a builder or someone
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that deeply wants to do cool [ __ ] and build something for yourself for your family for the world you got to be in
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the arena and in the arena there's a lot of fighting and there's a it's tough but I think it's a better way to live that's
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the reason why the best articulation of all this is is this term entrepreneurship because entrepreneurship is fundamentally you
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have a problem and you were solving in a way that uses the least amount of resources but has the highest amount of
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output and that's the reason why I love entrepreneurship I love we have millions of stores on Shopify some of them
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started because they were passionate about commercializing their their craft in some cases they started because they
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had no choice but the end result is they built something that is of value and they've shared it with everybody else
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and so that's what I signed up for but if I'm going to check that box this is the life I'm going to be the man in the
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arena I need to acknowledge there's going to be critics who are going to try to tear me down there's going to be internal
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critics that are going to try to mess that up and I'm still going to pursue I'm still going to move forward in progress
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um and I think therapy helps with that what's your relationship like with failure we talked a little bit about the
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idea of failure at the start of this conversation why people don't take the leap from that you know a miserable certain situation into an uncertain
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situation that might make give them a better life but what's your relationship been like with failure because everybody knows to be a successful entrepreneur to
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build great products you have to fail fast um but if you're struggling with you
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know enoughness then it seems like that might limit your ability to want to fail fast you know it
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it is certain that the more the more successes you have on your belt the easier it is to fail because you
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feel like if you've had you know nine out of ten things have been successful and that tenth is not it doesn't mean you are a failure so one thing is I
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think separating like you being a failure versus the project or the the particular thing being a failure is very
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very different which is hot which is very hard um Toby uh who you know is found or Shopify and person I spend most of my
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time with um building this coming over the last 13 or 14 years he has this great line which is that failure is the discovery of
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something that that didn't work when I think when you use that lens that failure is the Discovery or something that didn't work which he taught me that
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made failure totally different so now it's no longer about failing it's like what did I actually get from that that's
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going to make it better the next time and Shopify puts out a lot of products we
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had our uh we had something called Shopify editions which happened in February where we twice a year we basically do almost like the fashion
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industry we do like our spring collection and our winter collection so we do these things called editions where
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we put out all of the products and features we built over the last six months we do about a hundred of them
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each time which is a lot not every one of them is going to be a huge success
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but some of those will be a complete game changer for our business but also in the lives of the people that use our
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product and I think we have a courage about that I'm trying to have more of a courage about that myself if I take on new
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responsibilities or new roles am I going to be a failure and and the best example I can give you is for about
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five years or so I was shoplife's Chief Operating Officer and I don't think I was ever the most
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operationally minded person meaning I didn't necessarily live in the details I didn't necessarily live in spreadsheets
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but when Toby and the board asked me to be the Chief Operating Officer it was a huge it was a huge honor I mean shot play is
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such a great company wow like that's what they're asking me and I worked really really hard to be the best version of a chief operating officer
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and it was only three years ago or so that at some point it was obvious to me that like that's not really my skill set
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but I didn't want to say anything about that because I really believe that like I can figure it out I think I did a good job but maybe not the best job ever
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and once I began to talk about hey this is probably not the right role for me where I can be the best in the world at
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there's this other role which traditionally is called the president role which is very external facing
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maybe I can beat the best of world at that thing I'm not there yet but like that is a journey I can get on and maybe I don't have to be well-rounded maybe I
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can actually be spiky and instead of actually trying to be a well-rounded leader maybe I can focus on sharpening
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that point and sharpening that point over and over again and that's when you know I had a conversation with with Toby
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and and and and and the team said look there is this other role and we need to bring someone in whose life's work it
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would be to be a great Chief Operating Officer I mean we have that now but man Steve I did not want to admit
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that I was not the right CEO for Shopify because ego right total and and ego and
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insecurity one I'm admitting failure the other one is I like this role it's very important role but it was only when I
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sort of began to be honest about is this the right role for me that I began to say hey there's this other
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thing and I can tell you I am not a little bit happier now in my current role and not not and and and more like
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it is so much more meaningful for me to have this role today because I feel like this is really where Shopify will
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benefit the most from what is my superpower which is really storytelling and
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the company's better I like it better the currency was so much better than I was ever
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everything kind of came came about but it took it probably took too long I I think that story is an incredibly
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powerful one because they're I come across people all the time within my own companies but also just people that will send me messages who are currently in a
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role um maybe they're being offered a promotion into another role and because it's a bigger role with a bigger salary
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they are inclined to take it but there's that missing pause of sort of self-awareness where you've got your ego
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pulling you because I'm gonna have you know higher status in this company I'm gonna get more pay people are going to think I'm cooler and more impressive but
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then the most important long-term questions of course like am I good at this and do I would I really love my life more you see that a lot don't you
00:19:04
when someone gets promoted to a management position and suddenly the group of friends they have are now the people that they have to manage that
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point of self-awareness is so incredible I I reflect on a guy called Pete
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who I offered a promotion to one day and he was like
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no I'm not ready this must have been like what what
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I'm offering you more money the chance to become a director in the business and
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he'd been with the business for four years at that point um he stayed for two years after I even left he was just like I'm not quite
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ready yet he goes I've still got a lot left to learn a lot of skills um I like really like my current job
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yeah I like Pete Pete is the happiest guy I know he has his [ __ ] together way more
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than I do not is he happy but he also he he's great he's got great self-awareness you know one change that we recently
00:19:54
made at Shopify was we realized that a lot of people as they were going through the IC track or individual contributor track eventually just leads to a manager
00:20:01
track and so the upward mobility of your career ended up being you actually at some point if you're really good stop
00:20:07
doing the thing you're really good at and so very recently we put out uh sort of a new operating model for our team
00:20:14
for organization and I think I think it's been I think it got leaked to the Press so it's this is all public information but
00:20:20
if you want to be an incredible senior independent contributor because in your IC we will pay you the same rate that we
00:20:28
would pay a senior manager and that if you actually like your craft whether you're a developer or a marketer or a
00:20:33
salesperson or you're you're you're doing um data analysis or a data scientist if
00:20:38
you love your craft and I know some people who love their craft they've been doing it for 30 years you do not necessarily need to leave that craft to
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be a manager to get some sort of additional seniority or additional compensation and dispelling some of that
00:20:53
frankly like the [ __ ] around the only way to be successful is to be a manager is to lead people not everyone
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needs to lead people some people should be a coach other people should just continue becoming like the greatest
00:21:04
player on the field ever and making that okay I think is going to make shop play a much better company but one thing you
00:21:10
need to talk about that you sort of raise it that that that got me thinking about like the self-identity thing is
00:21:15
that I think a lot of times for this guy Pete Pete may really just be ambitious about
00:21:22
perfecting his craft and his skill set and he doesn't necessarily believe he's ready yet to leave that because there's
00:21:28
still work to be done I love that and I think in most companies what you end up with is the pizza the world when they
00:21:35
say we don't they don't want a promotion they often get to get taken out completely well Pete's not ambitious Pete's not going to be someone who's
00:21:41
going to be you know a real contributor longer term here maybe he's lazy Pete's not lazy he has a deep understanding I
00:21:47
don't know Pete is it's going to be hilarious yeah um I do know Pete but but Pete is obviously a clear understanding
00:21:53
of hey there's this thing there's this spiky object Don't Make Me a River Stone I don't want to be well-rounded I want
00:21:59
to be so good at this and by the way if I do this the company is going to get better I'm going to be happier our
00:22:05
customers are going to be happier it all kind of works out I think most companies turn their employees ultimately into
00:22:11
River Stones they say you got to be better here better there and I think instead this sort of t-shaped you've heard this
00:22:17
sort of t-shaped model of skill set I think the t-shaped is much better where you can go broad on a lot of different things but you go deep on one and then
00:22:24
one thing for me is the storytelling aspect of my job is making sure investors the public are Merchants media
00:22:32
everyone in the world knows what Shopify is up to and understands what our Ambitions are and so I'm trying to get really deep on the storytelling but I
00:22:38
also need to understand our apis I need to understand our infrastructure I need to understand you know how we how we build product and how we get [ __ ] done
00:22:44
at Shopify so I understand all those things because I need to tell speak to it intelligently and with conviction and
00:22:49
with a deep understanding but I'm never going to write code because there are people that should write code that are
00:22:55
going to be so much better than I'll ever be you do you did now Pete I remember him saying one of the things I
00:23:00
do remember in that meeting I remember where I was sat it's so funny because it was such a interesting moment for me I was very young in my career as like a
00:23:06
CEO and I remember where I sat when he said and what I recall is he was referencing that he still felt that
00:23:13
there was work to be done in his role and that he didn't want to move up into this I think it was a global role we're
00:23:18
offering him because he didn't feel like he'd quite finished the work in his current role which was just in the UK
00:23:24
um you reference spikiness you know you said you and that gave me
00:23:30
flashbacks to the conversation I had with um Jimmy Carter he said we don't need more people that are [ __ ] at physics find the thing you'll get out
00:23:36
and like double down there as career advice for an entrepreneur also when that's not an entrepreneur what do you mean by spikiness and why is
00:23:43
it important oh so this is going to be uh a long-window way to get there but I think it's important
00:23:49
um I um when I was building that t-shirt business in college
00:23:54
a mentor of mine say his name his name is Philip Reimer he's a senior partner at a very prestigious law firm called
00:24:00
Dentons they're in the UK they're everywhere all over the world he's like you know he's had this incredible white shoe Law Firm career
00:24:06
he basically convinced me to go to law school and he commits me to go to law school not to become a lawyer he's like the
00:24:13
skill set that you need given what I think your Ambitions are around business creation business building
00:24:18
entrepreneurship you are lacking some sophistication you're you're always going to struggle with these sort of
00:24:24
things he's like but I have this idea which is go to law school not to get good grades
00:24:29
necessarily not to get not to become a lawyer but to effectively selfishly
00:24:35
disseminate all this information from your classes to make you a better entrepreneur and I think because I sort of had a very
00:24:42
clear view that I wasn't sure at that time I was 21 when I started law school I didn't know exactly what my spiky
00:24:47
point was but I knew it had to do with entrepreneurship and so Phil when you're 21 I didn't know very much at 21. um I
00:24:53
thought this t-shirt business would just be the thing I'd keep doing for for many more years but Phil had this idea that actually to
00:25:00
sharpen your point you should do something that is not obvious and in hindsight it really feels like what Phil
00:25:05
was helping me to figure out was finding more Alpha in terms of Entrepreneurship
00:25:10
finding some Arbitrage opportunity something that that is that exists that no one is looking at but that I can take
00:25:16
advantage of something unique is that what you're saying yes exactly something really unique that hey you're a good entrepreneur you're not a great
00:25:21
entrepreneur you're not sophisticated you you don't understand you don't understand all these different aspects of Entrepreneurship you should go to law
00:25:28
school to not to be a lawyer but to be a better entrepreneur and you should be selfish in law school and in that in in
00:25:34
your curriculum in deriving as much insight as possible so when you leave Law School you can return to
00:25:39
entrepreneurship in a much better version of yourself because you'll have something that the competitor set other
00:25:45
ones wouldn't have wouldn't have that's right so you could have gone like you know Steve Jobs did that like typography class that's right and that's where we
00:25:50
have these incredible devices in front of us that's right so it's an unobvious skill that's complementary and that's why I say sort of funny alpha or an
00:25:56
Arbitrage opportunity because it know it's something that is not obvious to most people but now in hindsight when you think about it you're like well that
00:26:02
makes total sense look I I went to like I went to public high school and it was a good school but I didn't learn how to
00:26:07
write very well then I went to Mcgill and economics I didn't learn how to write very well I learned how to write really well in law school because all
00:26:13
you're doing is writing factums and memos all day you know all day long I learned how to negotiate and how to do a
00:26:19
real critical debate and critical reasoning I learned how to read 2 000 pages and pick up the one line that matters
00:26:25
all these things on their own doesn't seem like it would create the curriculum of a great long-term
00:26:32
entrepreneur but it did and I think part of the reason why I allowed myself to go through that process of law school was I
00:26:38
didn't know exactly what my spiky point was but it felt like it's it's definitely in the realm of
00:26:43
Entrepreneurship I didn't realize that I I would help build a company that would create millions of new entrepreneurs but
00:26:48
I knew entrepreneurship was deeply personal to me because it helped me it was my family Story of Survival it just
00:26:55
felt like this incredible tool that that most people had not discovered yet and so on that spiky point I think the
00:27:01
sooner you figure out that spiky point you don't have to be precise I didn't know I was going to run a software company but I knew that entrepreneurship
00:27:07
was deeply important to me and so as I made decisions starting at 21 years old every decision was under the lens of is
00:27:14
this going to help sharpen my my my points is this going to make me a better entrepreneur and
00:27:20
I think if I would have realized that 10 or 15 years later um it still would have been fine but it
00:27:26
may have not have happened as it wouldn't have happened the same way and it may have not led me to join a group
00:27:32
of you know a handful of really smart Engineers building this crazy piece of software called Shopify 14 years ago I
00:27:38
think this is an exceptionally un under spoken about point which is this idea of like skill stacking but stacking skills
00:27:44
that are unobvious and rare within an industry so if we take and I think we should go through this in a little bit
00:27:49
more detail because I think it can really have a profound impact on people I read about how um the best people in
00:27:55
the world I think it's a mathematical equation where I feel the best at six skills in an industry that are like unobvious you actually are the best in a
00:28:02
million people at that thing so I mean if there's a village of a million people and they showed this little graph I remember seeing it and writing about it
00:28:08
a little bit where if you just if you're just in the top 10 at six complementary skills you're the best in the village at
00:28:13
that particular thing like Cristiano Ronaldo the football player he's not the best he's not the fastest player in the
00:28:18
world he's not the the the um the best shooter in the world he doesn't take the best free kicks in the world doesn't
00:28:24
head the ball the best in the world he's considered the best player in the world by many because he indexes High the top
00:28:30
10 of various things I think about Jack he records this podcast now if Jack was uh wanted to be a podcast director what
00:28:37
all podcast directors or producers do is they'll go learn how to do microphones and cameras now interestingly I don't
00:28:45
think that's the the place to be placing your time to become the best in the world as we saw in the case of Steve
00:28:50
Jobs he went into typography and design and then made these beautiful devices which actually probably go and try and
00:28:56
get an unobvious but I skill that would be in high demand
00:29:03
and low Supply in this industry so if Jack went into theater he would learn maybe about how to
00:29:09
construct a story arc or if he went and did like I don't know is that set design also yeah or DJing he
00:29:15
went and learned to be a DJ then he would learn about stems and musics and whatever else or set design if he went
00:29:21
and did a theory so and and that would make him be I'm not using I'm just saying someone in Jack's position that
00:29:27
would make them be a real [ __ ] hard to find talent but it's funny because we can in Industries like I always think
00:29:33
this about um coders and I don't hate to sort of generalize here but it probably doesn't sound like a generalization
00:29:39
um it's sometimes hard to find someone who can code who's also an exceptional
00:29:45
Storyteller and visionary often in companies they're two separate roles right so if you're if you're a
00:29:51
coder instead of becoming even better at coding for example going and doing those little like public speaking sessions is
00:29:58
probably an unbelievable hack because then you can build and sell sure and actually that brings up two points one
00:30:03
is most people start companies with people just like them yeah yeah most people start companies of people that
00:30:08
they would have been friends with in high school I think that's a terrible idea in fact if you are in college right
00:30:13
now listening or watching this and you're in the business program Commerce or you're in the engineering program don't start a company with the person
00:30:20
sitting next to you walk across the street go to a different faculty go to faculty of Arts or the faculty of
00:30:25
philosophy or the faculty of engineering and find someone there to start a company with I think some of the best
00:30:31
Partnerships and relationships that I've seen that have built things that are that change the world from a company perspective philanthropically whatever
00:30:38
the whatever they're trying to build might be building with other people with complementary skill sets is incredibly
00:30:44
valuable in fact I think you get a much richer set of stacking of skills you
00:30:49
mentioned DJing in terms of skill set I never appreciated ever
00:30:55
how important my experience DJ and teaches like hundreds and hundreds of bar mitzvahs over my time hundreds I
00:31:01
never appreciated what I learned from as a DJ and how I'm how I apply to running a large public company but the truth is
00:31:07
there's all these different things so for example something I noticed early on it's like 14 or 15 years old if the
00:31:13
pre-meeting went really well with the clients no matter how the party went it was going to be a great result because I
00:31:20
had a good relationship a good connection with the client even if half the party didn't want to dance the
00:31:25
client knew me and knew enough about me and knew that I was going to try my best that even if half the party was dancing
00:31:30
they were happy about that and they were in your sign and they were on my side there was this immediate connection and so now before I go into any any you know
00:31:38
serious negotiation I try to get to know the person on the other side of the table I try to find some common ground where both dads or both parents or both
00:31:45
you know uh whatever we're both from the same place the first thing the second thing is read the room so one of the things about
00:31:51
DJing you have to do is you have to read the audience and if the audience you know is clearly if you're if you're
00:31:58
playing disco and no one's dancing and you got to make you know like a hard right into hip-hop or a rap or something
00:32:04
or top 40 like you can see glimpses of that you try one song you see how people you watch their faces how do people
00:32:10
resonate oh they really like this song great I'm gonna go like Mo Money Mo Problems from Notorious B.I.G and the
00:32:15
whole crowd erupts things like that really do make a difference um you know there is instead of asking
00:32:22
people to get up from their chairs and come onto the Dance Floor which is an awkward thing to ask people to do after
00:32:27
dinner instead have something in the middle of the dance where the people want to see so maybe for example one of
00:32:33
the people that is hosting makes a speech and you say ladies and gentlemen at this point please please get up in
00:32:38
your chairs and take 10 steps forward because the Father of the Bride is gonna say a few words and everyone gets up and
00:32:44
comes on the dance floor and then when that speech is done everyone's already on the dance floor and so finding these
00:32:49
hacks and these these sort of ways to um not manipulate but but but find better strategies for getting the thing
00:32:56
accomplished I learned all that in DJing and I can apply all that to running a large public company today
00:33:01
this um you know when we start businesses and stuff go back to that point again like we we tend to go deep
00:33:07
on the subject matter but what I've heard from that is our hobbies and the things and the Curiosity we have outside
00:33:12
of the area that we're building in is equally important then like if I'm
00:33:17
building up like I don't know if I'm building a um I'm building mugs for people to drink tea out of
00:33:23
much of my inspiration will come from all the other things I do in my part and the problem is we kind of de-prioritize that part of our Lives to focus on this
00:33:30
thing but taking a step away from the painting allows us to see the picture a bit clearer and also to to create that
00:33:36
picture a bit clearer which I think is a conversation people don't have enough because they think their hobbies are again deductive toys or games yeah yeah
00:33:42
I totally agree yeah I mean look I mean this is what a polymath is a polymath understands a lot of different areas of the world uh or comprehensivist
00:33:48
understand a lot of hair and pulls those different things in my um what's the polymath sorry uh polymath is someone
00:33:54
who knows a lot about a lot of different things okay now there are two things that I've done
00:33:59
that were hobbies that ended up being hugely valuable is one my wife started an ice cream company in 2016 after we
00:34:06
had our first daughter uh after our first child my wife really wanted to start an ice cream shop in our in our in
00:34:12
our neighborhood there was an ice cream shop and so it was clear it was her business not mine she was very clear
00:34:17
about that she wanted Independence but even just helping her on things like accounting or um accounts payable or
00:34:23
accounts receivable or helping your procure ice cream from the ice cream makers that was super valuable because
00:34:28
one it built huge empathy for the people that you shop that are starting out the second thing I did was
00:34:34
um during the pandemic I was all by myself I'm an extrovert as as you probably can tell
00:34:40
um my anxiety had had increased to a degree that I had not felt in many many years and what I realized was I was
00:34:47
drinking so much more coffee when I was by myself at home way more like double or even triple the
00:34:52
consumption and my best friend um who's a sort of a Teague you know T
00:34:58
guy loves tea said to me I'm gonna actually get you to stop drinking coffee in the afternoon and replace your coffee
00:35:04
with really great green tea I wasn't really a tea drinker and so David started to bring me this great tea and
00:35:10
at some point I was like you know David I want to actually experiment with more of the features on Shopify and I think
00:35:15
this tea thing I think most people's experience with tea was like someone getting like this gift basket and it was some bunch of crappy team there I was
00:35:21
like people don't know like about this really great tea they don't know how to make it they don't know what to use it
00:35:27
for when to drink it and so we created this this little tea business called fire belly and both both those things
00:35:33
were sort of hobbies in my life they were sort of Sunday afternoon activities I don't really watch sports on Sunday afternoons I like to Tinker and and try
00:35:39
different business ideas both those things have made me as a leader Shopify so much more valuable I understand
00:35:45
pretty much every feature and functionality that Shopify has because I tried for myself
00:35:50
and initially when I told people that I was starting a little tea business the answer was I don't like why are you
00:35:56
doing that that seems silly you're not going to change your life financially it feels like a distraction and I would say
00:36:01
that's one of the greatest tools that I've ever greatest things that I've ever done that has made me a better leader at
00:36:06
Shopify and it's just a hobby there's something really really powerful in that
00:36:12
because when we when I started this conversation I asked you why people don't take the leap and a lot of the reason why I think is because and we
00:36:17
talked about the psychology is when I think about starting a business like a tea business or any business I'm stood at the bottom
00:36:24
of Mount Everest looking out thinking Jesus Christ like I've got to find a website as you said I think I need loads
00:36:30
of money who's going to work for me where do I get the tea from how do I send it in the post um what's the packaging I need to do
00:36:35
branding and I need to do it all now and and also there's this other thing which
00:36:42
in our minds we think of success as being me making millions or me making a ton of
00:36:47
money what what I almost heard as you're telling that t-story was like have this passion
00:36:53
remove the expectation which so David brailles would told me about really well just remove the expectation if you have ever been anything more than a hobby and
00:37:00
just get going and you'll you'll stumble forward along the way and and that's okay I think if more entrepreneurs could
00:37:05
see that Mount Everest there's just a bunch of Pebbles and there's and remove the time frame where possible remove the
00:37:11
expectation of huge success and just stumble forward through the process we'd have so many great great more businesses
00:37:16
than we do now and everyone listening to this has that they have the hobby they have the they love tea or they love I
00:37:22
know coffee or matcha or whatever it is that perspective change of like okay well today I'm going to start my Shopify
00:37:28
store tomorrow I'll think of the name I won't I won't even tell anybody just to remove even more expectation and I'll just stumble forward through in my hobby
00:37:34
and see where we get to in 10 years most people on Shopify don't register their business until weeks after they sign up
00:37:40
for Shopify so most people don't even assume they're going to need to register a business and
00:37:45
that's okay and it's not to say that every idea you have in the shower needs to be commercialized needs to see the
00:37:51
light of day but if if there's an idea you have in the shower and you're having it a couple days in a row
00:37:56
try it out like I mean this isn't a pitch for Shopify but like it's it's less than a couple Starbucks
00:38:03
coffees to go start a business today and if you fail the cost of failure is as close to zero as it's ever been you
00:38:10
don't have to take a loan out of you don't have to mortgage your house you don't have to take food off the table hopefully and if it works you try it and if it
00:38:16
doesn't work you try something different but this idea of yeah there's like this barrier to
00:38:22
getting started and I think you know one of the reasons that I think one of the best times to start your entrepreneurial
00:38:28
career or your entrepreneurial you know business isn't isn't School the reason I think is
00:38:34
because when you're in school as a student there's very few expectations on you that this is going to be a huge success so it's kind of the perfect time
00:38:41
to get started whether you're in high school like with my DJ business or in college with my with when I sold
00:38:46
t-shirts there was very little expectation on me no one thought it was going to be successful anyway you still want
00:38:52
everyone in class yeah they're like great you're that's so cool you have a business no one asked me what my revenue is no one's asking about my ibit of
00:38:57
margins I think it is a lot easier to get started on a business when you're in school or you're where you have a job
00:39:04
and this is sort of your side Hustle the amount of people shop by right now is about 10 of all
00:39:10
e-commerce in the United States in places like Australia it's even way more than that um
00:39:15
I know most of our largest Merchants because I'm obsessed with this stuff I love it most of the businesses on
00:39:21
Shopify that are really successful the Homegrown success stories they were accidental it was Heather and Sharina
00:39:27
sitting at a coffee shop not too far from here with a friend of theirs I was a doctor who was wearing these hospital
00:39:32
scrubs that just looked like [ __ ] they're like we can do this better and that's what figs was born it was Ben
00:39:37
Francis who said why is there no clothes for just regular gym people either it's like gym rat stuff like bodybuilders or
00:39:43
it's yoga and that was the that's how gymshark came to the world or it's Tim and Joey and Albert saying why is there
00:39:50
no really great sustainable sneaker that feels good that's washable that costs this amount of money that was that that's how Alberts got started so most
00:39:57
no one had this massive 80-page business plan and then got started that's not how businesses are created in modern times
00:40:03
they're created based on this nugget of an idea and they're explored and you have and you get curious about you try
00:40:08
this other stuff and that's how you build companies that are long lasting that change the [ __ ] world and that's
00:40:14
how Shopify was started as well indeed indeed it was an immigrant from Germany
00:40:19
coming to Canada because he fell in love with a girl and got to got to this new country and couldn't get a job because
00:40:24
he didn't have his working papers and was told he can start a business and he looks around and he sees snow everywhere
00:40:30
and he says I'm going to start a snowboard company and in 2004 there's two ways to sell a
00:40:35
product on the Internet one way you sell them in a Marketplace which is very cheap very inexpensive like eBay or
00:40:41
something exactly but you're renting customers from that Marketplace they're not your customers the other way was to spend seven figures
00:40:48
no exaggeration and have one of these big Enterprise companies build you an online store
00:40:54
I didn't have that kind of money he didn't like those options so you wrote a piece of software and started selling
00:40:59
snowboards and the snowboard shop was called snow devil and very quickly people started asking him if they can
00:41:05
use the software to sell their own products and he decided snowboard store was a good idea but the software behind it was a great idea and that was how
00:41:12
shop I was born and I met Toby around that time when he was transitioning from snowboards into software and I became
00:41:18
one of the first customers to do Shopify in 2006. and then you were the first non-technical employee as well that's
00:41:24
right yeah and a couple years later after Law School uh I called him and said I want to join
00:41:29
you in a small handful of Engineers smartest people I've ever met in my life still to this day and said let me let me
00:41:35
be your Swiss army knife let me come in I don't care what you call me I'll be sales I'll be Finance I'll be marketing
00:41:40
I'll form Partnerships I'll do uh I'll do anything and everything you need because I believe the world will be
00:41:46
better if we actually get this thing off the ground and we've been working at this for you know it's my 14th year now
00:41:52
when people hear their stories of these you know couple of a couple of women a couple of men a
00:41:57
couple of people who had an idea they saw a kind of Gap in the market they pivoted into it seamlessly and here we are today you
00:42:04
know it's worth tens of billions of dollars whatever that I want to zoom in on a particular thing which is at that time because I hear
00:42:10
this all the time from entrepreneurs it's one of again one of the barriers for them starting is well someone's already doing it there's competition and
00:42:17
I think about every business that I've been involved in that's been successful and at the time when I did it there was someone that was way further down the
00:42:23
head than me and probably better capitalize better capitalized information that's right yeah smarter
00:42:29
yeah all those things and it never has mattered and I I can't quite articulate
00:42:34
why it doesn't matter I could probably try but I want you to um when Toby that small group of people yourself
00:42:41
went off on that Journey was their competitors totally tons very well big ones too Yahoo stores
00:42:48
no idea in 2006 Yahoo is a really big company Yahoo stores existed there were
00:42:55
companies called Magento which isn't still around today uh yeah not not as prevalent but that was around there were
00:43:00
major competitors out there but the idea wasn't necessarily to to try to do something no one else was doing it was
00:43:06
try to do it better and that I think is the difference between the great companies and and just the
00:43:12
good companies that there are always going to be good companies out there but most of them are not necessarily trying
00:43:17
to completely you know like move the needle on like what is possible
00:43:23
um all of those companies by the way that existed when Shopify was just getting started served a particular segment it was
00:43:30
either for you know like arts and crafts like an Etsy kind of style or for big companies IBM sap
00:43:36
Oracle had competitors there uh Yahoo store is focused on very very small businesses but
00:43:43
we never gave ourselves those constraints it was let's allow people and enable them to build beautiful
00:43:48
online stores quickly effectively that were customized for their particular brand and and try to bend the learning
00:43:55
curve around entrepreneurship and over time like over many you know oh it's it's now almost 20 years over time we're
00:44:03
like let's add payments let's add Capital Let's help with fulfillment we should do point of sale because physical
00:44:08
retail is important what if we also help them with things like cross-selling across different markets what if we create sort of a bank account to help
00:44:15
them manage their cash flow over time it sort of evolved from that but the initial idea had lots of other
00:44:22
competitors in the space this was not this massive novel thing we just did it better and it's funny because a lot of
00:44:27
those competitors we absolutely do not remember now because you did it better and that's the really important perspective shift which is not like am I
00:44:33
the only one with this idea there's probably not a lot of value in the idea itself but the execution of that idea can I do it better is really where
00:44:40
winners and losers are established so that begs the question how what's the philosophy and I'm very
00:44:47
intentional with the word philosophy there that enables a team to take a challenge where there's multiple competitors in your view and just do it
00:44:54
better I mean it's gonna sound trade but but you know having deep empathy for health
00:44:59
merchants and help your customer use your product is very very important and I think a lot of companies lose out of that they pre they focus on what you
00:45:06
know what is what is known as like Wales like who are the power users let's focus on that but we never did that we actually think
00:45:13
that the all of the merchants that I brought up so far in our conversation were Merchants that started at their mom's
00:45:20
kitchen table that grew to be multi-billion dollar you know hegemonic um incumbents
00:45:26
it's great I love that we have Staples and I love that we have Spanx and I love that we have you know uh um uh Black and
00:45:33
Decker and Mattel using Shopify but but those are companies that were already successful before they started using
00:45:39
Shopify the stores that we are most proud of that we love to talk about are the Homegrown success stories because
00:45:44
even though we are not responsible for their success we simply made the journey a little bit less difficult over time
00:45:50
but the way that we think about these sort of things are can we use software can we use technology to make things better and by
00:45:57
doing by adding more value A dispatch amount of value every single step of the way we think we build a lot of loyalty
00:46:02
with our merchants and that what then happens is the ones that do become successful never leave Shopify so there
00:46:08
are people that start a business that that fails um and and they decide to either shut it
00:46:13
down or they decide to Pivot to a different business we're okay with that we're not changing physics we know that that most small businesses will not be
00:46:19
multi-millionaire companies over time but key for us is that the ones that do succeed never have to leave the platform
00:46:25
so it's almost like when you start on Shopify it's super easy super simple in an hour or two you can build a beautiful
00:46:31
online store but over time as the complexity of your business increases the solutions on Shopify sort of reveals
00:46:38
itself over time but it does so at the right time so you are not overwhelmed and I think we are very hard on
00:46:43
ourselves and I mean that's the right term we're hard on ourselves that we really want to
00:46:49
continue to push the envelope here's a very simple example um everyone right now is talking about AI everyone's obviously chat EBT is
00:46:55
really really cool we were using it already in a couple different ways but the way we thought about it when it first came out was this is all great
00:47:01
very cool technology what is it going to do for merchants what is the Practical implications of AI
00:47:09
on the lives of of the merchants and for us was like well wouldn't be cool if AI helped Merchants write product
00:47:14
descriptions so you you put in your product photography or some meta tags and chat
00:47:20
gbt helps you write a product description that will convert better that is really practical
00:47:26
um you know obviously in web 3 for example we always thought about this is all cool technology the blockchain is amazing what can we do with it what if
00:47:32
we can do token gated Commerce so that you can reward your most loyal customers with new opportunities new discounts new
00:47:38
events we use this lens of of of practicality across every single feature we have and
00:47:45
we also think about well what happens if this particular Merchant gets really really big um I have a bit of a Moby Dick story
00:47:52
um my Moby Dick in terms of Shopify the the one brand Merchant that I've wanted
00:47:57
on Shopify for so damn long is a company called Supreme they're incredible the Supreme story is
00:48:04
amazing but the reason I wanted Supreme on Shopify so badly more than almost every other any other brand
00:48:10
um is because I knew that they would test the limits of Shopify their flash
00:48:15
sales are probably the largest flash sales across the entire internet which means they're probably the largest flash
00:48:20
sales across all of retail and I knew that if we got them on it would pull Shopify into a new category of
00:48:26
resiliency of performance most companies would have shot away from that most companies have been like we
00:48:31
don't want Supreme we know they're a great brand but they're gonna break this place they're gonna break our product they're gonna break our infrastructure
00:48:37
we invite that in we want Supreme to be on because we know that if we can handle an iconic Supreme flash sale we can
00:48:44
handle anything else and there's a little bit of like a there's a great book by Nissim tele called anti-fragile
00:48:50
are you familiar with that I love that book and and oh yeah for those that haven't read the book All you have to understand is that
00:48:55
there are three systems there's the fragile system I take this glass I drop it it breaks there's a robust system I
00:49:02
take this I drop it it stays stays as a glass but there's a third system like the immune system where if you break it
00:49:08
it actually rebuilds itself better stronger faster and shopify's fundamentally an anti-fragile company
00:49:15
and I think you your companies are the same way you guys invite what called pain called challenge
00:49:21
because ultimately you want to come out the other side better and most companies like literally 95 percent of companies
00:49:27
out there maybe more don't want that pain they want to be copacetic and they
00:49:32
want to continue the status quo really interesting you know I I mean my
00:49:38
head went all over the place when you're just going through those stories because I remember when this podcast started to grow our provider actually told us to
00:49:44
leave because we're bringing too much traffic so that provider is never going to have incredibly sexual successful
00:49:50
podcast ever again because they told you to leave what if they would have invited you to stay and said we're going to build more resiliency yeah for you they
00:49:57
were like complaining about us they were like shame on this shame on them yeah so we we moved to a different um someone
00:50:02
else that could host us because they said that there we had too many downloads or something you have too many deaths that is literally saying you were
00:50:09
too successful am I right jack I want to make sure I'm correct because you dealt with them yeah
00:50:14
we were causing them I mean we're not costing them too much money by the way most companies are like that they fire customers that pull
00:50:21
them in in different directions as opposed to the best companies Embrace
00:50:26
that and say come break our stuff it's going to make us better if you believe like and by the way anti-fragility is
00:50:33
not just something for companies also for human beings I think all the stuff we talked about about my upbringing made
00:50:38
me better Made Me Stronger do I wish if those things wouldn't have happened potentially I mean in hindsight I wish I
00:50:44
would have had less anxiety maybe but maybe I would be sitting here with with you Steve today if those things wouldn't
00:50:49
have happened it's resilience the antidote for that and and if so then how do we Foster resilience in teams and people because if you're at Shopify and
00:50:56
you're an ambitious company as I know you guys are and you're saying you know AI comes out and you're saying to the team listen forward let's figure this
00:51:03
thing out let's let's build some stuff and let's try it let's go forward you're gonna have to bring people along with you and those people are gonna go I
00:51:09
just got comfortable with with what we're doing now Harley and now you're telling me to so do you how do you
00:51:14
create that culture that Fosters that sense of like resiliency and positive attitude towards change okay two things
00:51:20
one is resiliency can be taught you're not born resilient you can actually learn resiliency you can learn from your
00:51:25
experiences you can learn it from practice but resiliency I don't believe if some of you either have or you don't you can actually build resiliency in
00:51:32
fact I think people the most interesting people that I know that are resilient have had something happen to them that
00:51:38
allowed them to build resilience on their own some of them you know cracked but others actually it's like you know
00:51:44
the the the metaphor that I love to use like a huge tidal wave is coming some people grab their surfboards and some
00:51:49
people run for the beach get the towel I like to surfboard people the surfboard people are my people those are the entrepreneurs
00:51:55
in terms of how we do it at Shopify is Shopify as a company building software for entrepreneurs that is built by
00:52:01
entrepreneurs the like the amount of people at Shopify who had a business have a business are about to start a
00:52:08
business have side hustles anyone you've ever met that works at Shopify because I know the people you've met at Shopify Steve they're also entrepreneurs and
00:52:15
actually rather than on doing their own Ventures we are collectively coming together to build something much bigger
00:52:21
together like one plus one equals ten um and I think one of the ways that you Foster a culture of resiliency is look
00:52:28
for the entrepreneurs the reason I met Toby in 2005 was I moved to Ottawa to go
00:52:34
to law school had no friends no family never been to the city I only went there because a mentor told me to go to law
00:52:39
school and he was teaching law at the University of Ottawa that's how I got there and I asked one simple question anyone I met where do the entrepreneurs
00:52:46
hang out and I found this coffee shop with five other entrepreneurs who every Friday night got together and spent time
00:52:52
learning from each other and sharing War Stories and sharing tactics and that became my tribe one of those
00:52:57
entrepreneurs was Toby so I love entrepreneurial people I love resilient people and so you can search those
00:53:05
people out when you're building your company or trying to create a culture that is you know super effective that
00:53:11
has it looks for it looks for the alpha opportunities that is very ambitious that works hard
00:53:17
invite entrepreneurs into your company create an environment that entrepreneurs want to be there and and I think that's
00:53:23
what we've done and I think we've met 10 000 people at Shopify and I would say the vast majority of them would say
00:53:28
they're either entrepreneurs or aspiring entrepreneurs but every single person at Shopify is very entrepreneurial and it's
00:53:34
the same reason where you told me a story earlier About You Know Jack taking a photo of
00:53:40
the of the bookshelf yeah I mean I'm not just saying because he's filming us and he's got to make me look good here but like that's the
00:53:47
entrepreneurial way to do it the non-entrepreneur way to do it is to be like yeah we need some books you have
00:53:52
the exact same books behind you here as you do in London most people won't notice that but I
00:53:58
noticed the amount of attention and to detail you have and the care you've taken that every that that b is exactly
00:54:03
where the B is on the shelf behind you that matters it doesn't matter to everybody but it matters to the right types of people and when you do that you
00:54:10
invite more of those people into your life do you think as well though that
00:54:16
when you think about companies and leaders and how the culture is set and how that philosophy of like attention to detail is set I've often thought that
00:54:24
you might get like a group of people like Disciples of the culture maybe the original Founders or something and they said they set that philosophy they go
00:54:30
this is who we are we care about the bookshelf being the same no matter where we are in the world and then you have
00:54:35
this other type of people who are susceptible to go either way depending on the culture they're in and if a culture is strong those people
00:54:42
become the culture the cultures if they went somewhere else they'd probably behave differently and but that comes down to the culture
00:54:48
just being absolutely crystal clear and the hiring of that culture being disciplined and the firing yeah I mean
00:54:55
let me let me disagree with you on one point I don't think culture should be static I actually think that every new person that joins your company or my
00:55:02
company the culture should change slightly and hopefully it gets better over time but I think there's a lot of
00:55:07
companies that they put a a poster of an eagle up on the wall that says leadership underneath and they call that culture
00:55:13
or they say you know they're famously Patty McCormick created what's what's now damn soon as the Netflix culture
00:55:19
guide yeah I remember and what was cool about that was the talent team recruiting team at Netflix gave out this
00:55:25
culture guide in advance of you even applying to Netflix it was a public document so you can read this and if
00:55:30
this does not resonate or this is offensive to you don't even apply I think it's actually a very good thing to do because it's just it's very honest
00:55:37
about this is the type of place I think one of the one of the funniest lines in there was um uh mediocre performance will lead to
00:55:44
uh Superior Severance I love that right it's super super cool so
00:55:50
there's there's that aspect which I think is is really interesting but I think the culture should continue to
00:55:55
evolve and everyone that joins it should get better and better but I want to just say something like this is this Narrative of the early days
00:56:02
I think it's [ __ ] like this is a better version of Shopify right now than we've ever had our team is better our
00:56:08
leaders are better yeah there's some Romanticism about the early days where
00:56:13
you know like there's a photo that floats around every now and then of me sweeping the floors I get it that was kind of romantic that we sleep the
00:56:19
floors ourselves but I actually think over time you can have a fat if you like
00:56:26
part of this is like is your company founder-led or professionally managed and those are fine things but it I don't
00:56:31
actually think you need to actually have a Founder there to be to have a Founder mindset I think you actually need to
00:56:38
have if your culture is strong and people do the right thing when no one is watching and people are constantly challenging
00:56:44
each other and people are constantly trying to like pull the product in in a really unique positive way
00:56:50
that's a place where more people like us want to work and therefore other people like us want to work as well and
00:56:57
that's why I love the idea of like building a company for entrepreneurs built by entrepreneurs that is really
00:57:03
compelling when I when I when I speak about culture I think I'm kind of using the word interchangeably with the word um in that particular case maybe the
00:57:09
word values but let's if we think about company culture in the context you're describing it I was um I was doing some
00:57:15
writing over New Years and I was looking at the life cycles of companies and they they often start like Cults and I went
00:57:22
through I think IBM Instagram all of these huge companies and I found quotes of the founders describing the early
00:57:28
days like a cult and then they go into this kind of growth phase where because everything is
00:57:33
breaking and they're trying to keep up with the market demand they're having to like rapidly install processes this is usually where Founders like hire someone
00:57:39
who's got like gray hair who's done it before and they sit them down with the little cult and they're like hump in that growth phase and then they get to
00:57:45
kind of like this Enterprise phase where the processes are in place work-life balance has kind of been restored they
00:57:51
have a lot of people so now they have like a HR department and things are different now
00:57:56
going back to that first phase that cult phase it seemed pretty clear to me even like Peter there was a quote from Peter Thiel
00:58:02
where he was like you know um see what's the effect of the start
00:58:08
should resemble a cult do you believe that it's something I've pondered because the word go is such a toxic word
00:58:14
so be careful yeah I mean I I I yeah I don't know I'm not sure if cult's word I
00:58:19
would use what I do think is that you need to have like and this is not just in early days it's at every stage of a
00:58:25
great company you have to have a strong mission and part of the reason that I think Shopify
00:58:31
for me at least is the place where I can do my best work is because the mission
00:58:36
is not interesting or cool or it really hits home for me
00:58:42
I'm not it's not to say that I wouldn't be a good a good president of of Pepsi I'm sure Pepsi's Mission I don't know
00:58:48
what it is but I assume it's something like do something with the world and make people happy or something like that ultimately they're selling products
00:58:54
they're selling sugar water and they're selling candy and they're selling chips and whatever they whatever Pepsi sells
00:59:01
I don't think I can do my life's work at Pepsi I don't because ultimately at the end of the day the mission of the
00:59:06
company even if you add all types of you know rose petal glasses and and you say well we're not it's we're not selling
00:59:12
Cola we are you know we are nourishing the Youth of the world to pursue their
00:59:18
you're selling something that like I like but I don't really love
00:59:23
and I think if you're if you have the ability to find a company whose mission
00:59:29
you believe in in every in any stage really hits you hard that's probably the
00:59:35
company you should go work at and you've probably seen that for a very long time and even the fact that
00:59:40
not every not every person needs to say to every company forever not everyone's gonna be a lifer that's okay people want
00:59:45
to jump on the bus and or the rocket ship at different times that's fine but I think you do your best work when the mission of the company deeply reflects
00:59:52
your own life's Mission if I wasn't at Shopify if Shopify didn't exist I
00:59:57
probably would be doing something around encouraging more entrepreneurship inspiring more entrepreneurs creating
01:00:04
tools that help entrepreneurs start scale and build faster I just found this this vehicle that does
01:00:09
it way more efficiently than I ever could do on my own it's called Shopify so you damn right I'm going to want to be on that bus or that rocket ship
01:00:16
but I don't think it has anything to do with what's on the wall I think it has to do with the fact like what is the
01:00:21
company actually doing if you strip away all the marketing speak and all the brands speak what is the point of the
01:00:26
company what's the objective and I think that's that really matters for those entrepreneurs then that
01:00:32
Shopify supports when we talked about this Mount Everest analogy where you're you're thinking about starting a
01:00:38
business you're looking up it feels super intimidating we talked about how you can break that down into simpler steps focusing on turning your hobby
01:00:43
into a into a small business you gave the example that many of shopify's merchants don't even register the
01:00:50
company by the time they start the store the other part that's um intimidating when I'm thinking about starting a
01:00:55
business if I'm a startup entrepreneur it's just information and you used a word earlier on use the word mentorship
01:01:02
now okay I've got a philosophy to how I'm going to start it I'm going to focus on a hobby Harley
01:01:08
um I don't need a ton of capital as you've outlined but then there's this information piece which it may be the
01:01:13
most important piece because information for example is even the knowledge that a Shopify exists it's also like how do I
01:01:19
find where I'm gonna get this tea from how would you recommend an entrepreneur solve the information problem
01:01:25
and if you could give me some kind of reference to your framework on on mentorship that'd be super helpful yeah
01:01:30
I mean the mentorship framework that I use it's actually really simple it's that I don't think any any one particular Mentor is going to be uh you
01:01:37
should wholesale take everything they say um Lindsay and I got married in 2013 and
01:01:43
I thought about who are all the people that I perceived to have a really great
01:01:49
relationship with our spouses and I went through the list and I kind of laughed I was like okay like
01:01:55
am I really gonna ask that person who my mentor like I don't really respect that person in any other Avenue in their life
01:02:00
so like why would that person be my mentor so I went through this list and I realized you know what like I'm I'm doing this all wrong if I want to be a
01:02:06
really good husband a really good father a really good leader of Shopify I want to be a really good human being from a
01:02:12
charity or philanthropy perspective instead of trying to find one size fits all like one person does all those
01:02:19
things where it all comes together it would be so much better for me actually to just focus on verticals so in the
01:02:25
vertical of parenting who's someone that I think does a really good job in parenting
01:02:30
three or four people I'll give them a call the neat part about doing it that way as opposed to saying and by the way the person that like
01:02:37
can't believe I'm sharing this but this is kind of funny um I told you about a mentor of mine that convinced me to go to law school
01:02:44
I love that guy he's a huge part of my life he's on his third marriage yeah he's not going to be my marriage Mentor
01:02:50
he'll be a divorcement maybe yeah but he's really good about understanding skill set or skill stacking as we talked
01:02:56
about there was someone that I called when I was about to get married to Lindsay who I just felt had the most
01:03:01
special relationship with his wife and I began meeting him and asking questions about how do you cultivate that the same
01:03:08
thing with parenting but all of these mentors in each of these verticals they're not the same people now the
01:03:13
reason that's that's that's important is because like that like a video game or like any skill set you can't be good at
01:03:19
everything and so I'm able to derive different things from each of these mentors and then create my own version of it but the second reason is so it's a
01:03:25
really cool way to do it is that person who is a really great husband but maybe not a great entrepreneur a lot of people like no one
01:03:33
else is calling him to ask for his advice on parenting because most people are like well he's not someone I'd want to emulate because in business he's not
01:03:39
that successful or or in other aspects of Life he's not someone who had wanna Who had who I admire
01:03:45
and so the way that I've always thought of mentoring is find these different people for different aspects of your life and then as as your
01:03:52
as you evolve you may have to replace them and bring them in bring them out some people may be around for a long
01:03:58
time other people after two years I mean I had a really good Mentor around parenting who was really only valuable
01:04:04
for newborns and it turned out that couple years you know as the kids grew it wasn't doing a very good job he wasn't teaching his kids all the cool
01:04:10
stuff that I want to teach my kids like skiing for example so that's part of my philosophy on on
01:04:15
mentorship um more generally I think there's sort of two sides so you have mentorship on this side which is like people you want to emulate but there's also sort of the
01:04:22
tribe side of things and the one thing that I don't think enough people take advantage of is whatever company you're
01:04:27
trying to build in whatever vertical or geography or or you know whatever place there are probably dozens of other
01:04:33
people doing that exact same thing whether you're in London or you're in like Ottawa Canada
01:04:39
and finding a group of people who are at a similar stage even if they're not doing the same like if I'm building a
01:04:45
t-shirt business and you're building a DJ company like but I'm just getting started you're just getting started we probably both need to figure out like
01:04:51
how to set up a bank accounts and how to get our first sale and we probably have to figure out like simple bookkeeping for example so finding people that
01:04:58
actually are the similar stage even if they're not the same vertical as you are is super valuable and those people exist they're everywhere but finding them used
01:05:05
to be really difficult I think now it's much easier go to Reddit look on YouTube like you can literally go there's a
01:05:11
video about bookkeeping for DJ companies there's probably a video on YouTube Somewhere go look at the comments who's
01:05:17
engaging the comments there who's replying to those comments or on Reddit who's sort of a power user in a particular subreddit you can find those
01:05:24
people either online or or in person and you can build yourself and informal board of directors when you're getting
01:05:30
started now if one of you eclipses the other in terms of growth you're probably not going to find as much value from
01:05:35
that particular tribe as you as you previously did you're going on a different tribe but if you do this over time you actually end up with far more
01:05:45
the acquisition of information gets much easier over time and I don't think enough people take advantage of that if
01:05:51
I if I gave you um if I give you three million dollars and I said Harley you've got to invest
01:05:56
one million dollars in three companies more specifically three founders that
01:06:02
are currently Shopify customers who would you invest it in and why would you choose those entrepreneurs and founders
01:06:10
it's like asking me like you know choose your babies yeah choose your favorite child yeah really I'm trying to get the
01:06:16
characteristics of the founders that you back you know I I know right now it's almost uh if you saw a word clouded
01:06:22
social media right now the term content creator would come up probably more than another other tournament I think actually it is completely misguided of
01:06:30
what people think content creators are or do I think a lot of people assume that what's happening right now in sort of the content creation spaces you have
01:06:36
someone that has a super successful podcast for example or a super successful blog or super successful you
01:06:43
know YouTube channel and they want to they want to expand their monetization
01:06:48
so they do something like they make t-shirts with you know the dire with Co
01:06:53
on it the greatest content creators now that I see really building their brands are doing something totally different
01:07:00
and I know this is an obvious example but
01:07:05
what Kylie Jenner did with Kylie Cosmetics is nothing short of brilliant now it's not to say that that you know
01:07:12
she came with a built-in audience she was on this crazy TV show for her whole childhood
01:07:18
she was someone who if you followed her on social media eight years ago eight
01:07:23
years ago you would have seen she really cares about makeup she was in makeup tutorials and she was doing makeup
01:07:29
classes and she was giving tips and tricks about makeup and then eventually she's like you know what I want to create a better version
01:07:34
of makeup for myself and so she went into the lab I know where the lab is not too far from here I know the store
01:07:40
really well and she went and she created what she believed was a better version of makeup called Kylie cosmetics and
01:07:47
then she brought it to the world what Jimmy did with like Beast burgers or with feastables Mr
01:07:54
Beast Mr Pizza yeah Mr Beast did with with with with Beast burger or feasible he didn't just go and go to a chocolate
01:08:00
company and say I want to create a Mr Beast chocolate bar he went he loves
01:08:05
chocolate he loves chocolate he also love burgers and he said let's create a Better Burger than I can get right now on Uber Eats and he went and he
01:08:12
cultivated it he said this is [ __ ] delicious and now he's going to actually distribute it he's going to actually
01:08:17
scale it those are I would definitely put one of those millions of dollars into the hands of a Creator who's on the
01:08:24
precipice of figuring out what exactly does my audience like and then creating a better version of that
01:08:30
because I think that most of the content creators out there do create promotional products where they put their sticker on
01:08:36
something that already exists but the good ones the great ones they actually improve on what already exists in the
01:08:41
world and then they have a built-in distribution Channel because they already have an audience so that would be the first one the second one I think
01:08:47
would be someone who does something very nichy um you and I are both in black t-shirts in
01:08:53
my opinion there's someone who thinks about black t-shirts more than anybody else on the planet his name is James
01:09:00
James purse James purse is obsessed with black t-shirts and so I love wearing
01:09:06
black t-shirts so this is maybe a selfish one but I'd put a million dollars out of the three million that you're you're giving me metaphorically
01:09:11
into James and I would say go do more of this because I actually now I'm not sure
01:09:16
he needs my money I'm certainly Mr Beast doesn't eat my money either but I love the idea of someone going super deep on
01:09:22
one particular thing and building the best version of it on the planet I don't think most people do it I think most
01:09:28
people start with something like a t-shirt and they go very very Broad and James hasn't I mean he has he makes
01:09:34
other clothing but he has a ping pong table I'm not joking that he makes which is the most beautiful ping pong table
01:09:40
he's ever I've ever seen he he has a couple of these sort of villa rentals in Mexico
01:09:46
um which he designed himself but he's he it's one particular vertical that I think is really really cool maybe the
01:09:52
third thing that I would uh that I'd invest in so content creator be first someone like James purse who does one
01:09:57
vertical really well be the second the third one would be someone who is trying to bring something that was
01:10:03
unattainable for the masses into their hands so this microphone that we're using right
01:10:08
now is a sure sm7b and from everything I've read because I like this type of
01:10:15
stuff it is like one of the greatest pieces of engineering audio engineering ever created which is why sure who makes
01:10:20
the microphone hasn't really changed it much this is a great microphone it's expensive
01:10:27
someone who is taking a microphone like this this type of quality and creating a less expensive version of this so more
01:10:33
people can try their head at podcasting that would be really cool too interesting making light quality more
01:10:39
accessible to the masses right that's right and I don't just mean like there are other good microphones out there but you know the difference between a DSLR
01:10:47
camera that we're using now versus a webcam of course and in terms of the
01:10:53
characteristics of the human what what do you bet on I mean we talked about this a lot so
01:10:59
it's going to sound repetitive but it's resiliency I'm looking for those surfboard people the people that see
01:11:06
that wave and grab the surfboard I want people that are optimistic but I think generally the people that are that grab the surfboard are optimistic I want
01:11:13
people that are hard working but I find generally the people that grab the surfboard are also hard working I want people that are High character I think
01:11:18
those are often the same people but I want someone who um
01:11:24
if you were to give them a million dollars or 10 million or 100 million dollars they would still do the exact same thing the day later because that is
01:11:30
their mission that is their life's work and I think if you find that you should cherish that anyone who's watching that has found that thing that no matter what
01:11:37
they had or don't have would do this particular thing those are the types of people that I would back I don't really
01:11:42
care where they're based I don't really care what their experience is um I care about are they the surfboard
01:11:47
people because I think surfboard people are deeply curious and deeply ambitious we spoke to your team and asked them
01:11:53
what you in particular were good at um oh God they um they did not tell me you did that did
01:11:59
they not they did not we said we said could you tell us everything Harley's good at and there was like a big sort of 30 second pause and then they just hung
01:12:05
up the phone and so we couldn't so we'll move on um I Heard the gas but backstage here yeah
01:12:13
I probably couldn't hear that on the mic so everyone everyone that like Works closely on my team uh are all also all
01:12:18
entrepreneurs himself they all have side hustles oh really cool yeah no they said lots of many many amazing things about
01:12:24
you um many many amazing things the the one that I wanted to focus in on because I couldn't quite I wanted you to kind of
01:12:31
explain this is one of your team members said he's very very good at the telescope process of
01:12:36
effective prioritization what What on earth does that mean a calendar everything
01:12:43
well they made it sound much better maybe they should be the storytelligence I I truly like before I came here I want
01:12:51
to grab a quick coffee um that was in the calendar my my meditation this morning is in the
01:12:57
calendar the things that I really really care about I diarize and I stick to that diarization and because of that I think
01:13:02
it's easier for me to prioritize what's important in my life both professionally and personally than most people who they
01:13:08
try to fit things in um I often don't walk into a place you know you ever meet those people that are
01:13:13
like they're always kind of in a rush me okay I'm not I'm usually not a rush I'm I'm hard driving and I'm like I'm always
01:13:19
you know super go go go all the time but I'm not usually not a Russian and the reason is because the things that are deeply important to me
01:13:26
are in the calendar and I think most people don't I think the user I think a lot of people use their calendar for diarizing a zoom call or diarizer you
01:13:33
know scheduling I don't know like lunch I I this is gonna sound maybe lame to some people it's worked well for me in
01:13:40
my calendar you will see walk with Lindsay like walk with my wife you will see like ski time with Bailey or Zoe
01:13:47
um everything is in the calendar every person that I want to hang out with that I want to actually a mentor of mine that
01:13:52
I don't think I'm spending enough time with they go in the calendar every four weeks and I commit to that that helps me
01:13:57
I'm not sure I'm like the world's greatest prioritizer but because that I'm able to prioritize things in a way
01:14:03
that that I think most people may not always be able to do so that that's one thing in
01:14:09
terms of the other prioritization um there's very few things that are like nice to haves in my life I I don't do
01:14:16
the nice to have thing these are things that are in my life are must-haves and um
01:14:22
Shopify is very important to me Lindsay and the girls are very important to me um like some of the charity projects
01:14:29
we're doing particularly some some of the um uh some of the Jewish charity projects we're doing right now in Canada
01:14:34
are very important to me there's not much else I'm not trying to also qualify
01:14:39
for a marathon I'm not also trying to um you know do research on some other
01:14:45
topic like this is kind of the stuff that matters and so when when our when we first you and I first
01:14:51
connected I knew that I would one day would love to be on your show why because like when
01:14:57
I think about do you know the concept icky guy yeah yeah so when I think about the ikigai concept which is really life's work by the way just a Japanese a
01:15:04
Japanese version of it which is far more uh elegant than than the term life's work but what am I good at what is the
01:15:10
world going to find Value in what can I get paid for and and um and what what adds the most amount of
01:15:15
value I think generally I forgot the exact terms this conversation with you hits a bunch
01:15:21
of those like the intersections of Venn diagram this hits you're a great entrepreneur your audience are great
01:15:27
entrepreneurs I knew the conversation would be interesting because I listened to this podcast and I love your show
01:15:32
um it was obvious to say yes if someone else asked me to to to do a conversation for a couple
01:15:38
of hours like we are today I have to put it through the filter of like where does this hit on the ikigai Spectrum or on
01:15:44
the life's work Spectrum I think that's why they say that as you'll know if you've listened to the last few episodes of this podcast we're
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01:17:42
has been your most difficult personal challenge like what
01:17:47
was the day or the period where you had your hardest time I think it was
01:17:52
um on a personal level it was probably the pandemic I felt very very lonely
01:17:59
um I I just I was low on energy I was high in anxiety and I wasn't making time it was like the
01:18:08
pandemic was crazy for Shopify overnight every physical retailer shut down and we were really lucky in that a lot
01:18:15
of them ended up coming online with Shopify that was really cool but we ended up hiring a ton of people very very quickly we were always by ourselves
01:18:21
we were fully you know fully remote at that point and I I was not in a good place
01:18:26
um what'd you mean you went in a good place um I wasn't present at all for my I don't think I was present for my team
01:18:33
and I don't think I was present at home I felt like I was simply just trying to tread water and I wasn't making time I had this sort
01:18:40
of great I talked about my calendar efficiency I had this great sort of plan usually and then the pandemic hit and
01:18:45
like everything changed and scheduling all this time I didn't replace the time with mentors that I meet in person with
01:18:52
with virtual coffees I just canceled it and so I just it was a very
01:18:58
um reactive period for me where I don't think I was mindful of what I needed to be a good leader and we were just hiring
01:19:04
a ton of people and I was lonely I was really [ __ ] lonely that was a low point on a professional
01:19:10
side on a personal side it actually happened a couple years prior to that and it was really around the transition from being sort of Co to
01:19:18
being president um I felt like I was letting down the
01:19:23
company I was letting down Toby I was letting down myself if I if I didn't have a particular role at the company and that role came with a huge head
01:19:30
count like all these different teams reported up to me um from a headcount perspective there were like six thousand people that
01:19:36
reported to me it was kind of a crazy thing and and but I knew it wasn't the right job for me but I did not have the
01:19:41
self-confidence nor do I nor did I have the um
01:19:46
enough introspection to say I'm in the wrong job and I was fortunate that other people
01:19:52
especially Toby kind of pulled me into this new thing and said hey there's a role here that is different than what you're doing and if you can just get
01:19:58
over the fact that you're not going to be you're not going to have 6 000 direct reports but rather you're going to have a couple hundred record ports or maybe
01:20:04
less than that even but you're going to do more of the stuff you want which also happens to be more valuable for Shopify
01:20:10
that we're gonna have a new phase we have this thing in Shopify called tours of Duty it's every three years and um a
01:20:16
tour of Duty is you know it's a new new mandate new objective and for the most part most my tours of Duty up until this
01:20:22
this most recent one I was doing the same thing I was just grabbing as much as I can trying like Swiss army knife stuff
01:20:28
but I never kind of settled in to say where do I actually want to do like like
01:20:34
what is my craft here I always love storytelling but I was never I think I was too caught up
01:20:42
with ego and insecurity to admit this is the [ __ ] I want to do I don't want this
01:20:47
rest of my life I want to get so good at this and it was really with help with coaching and and the
01:20:53
people around me that I was like Hey what if I actually just did this thing what if I took this other role called the president of Shopify and I just
01:20:59
focused on this one aspect versus all the other things I was doing and turned out not only is it okay but it's way
01:21:06
more valuable and and I think I'm a much more valuable member of our team because I've I've sharpened my point rather than
01:21:12
become a well-rounded Riverstone in those dark moments and those hard times did you did you speak to anybody as in
01:21:19
what I'm saying I mean speak to the people that were next to you did you speak to Toby did you tell your wife how you were feeling my wife knew I wasn't
01:21:26
happy did you have a conversation um no I don't think I was able I don't
01:21:31
think at that particular moment I was able to actually even see it I was like look I've been here for a long time
01:21:37
maybe this is it maybe I've hit I've hit the my Max here right I mean I've been
01:21:43
here for a third of my life maybe this is it maybe like I should just quit while I'm ahead and what I didn't fully
01:21:48
appreciate is that the thing that I really want to do is also the thing that everyone else really
01:21:54
wants me to do it's also really the thing that is most valuable to the company at this particular but that's not enough yeah
01:22:02
I'm not doing enough am I contributing enough and what does that mean about me and myself that's right like I'm not I obviously I'm not
01:22:08
enough I am the happiest I'm not just saying that uh because Ron camera at this
01:22:14
particular moment I'm the happiest and most fulfilled and I find the most meaning in my work that I have in a very very long time and it's because
01:22:23
I'm doing the thing I should be doing which is this particular skill this particular role that I have
01:22:30
is kind of built perfectly for me and I need to be okay with the fact that I
01:22:35
don't have the largest head count and most of them doesn't report to me and I don't really care about that what I care about is am I adding the most amount of
01:22:41
value and I might I might do I feel like I'm growing do I feel like I'm actually contributing both to the company but
01:22:47
also to my own developments and I think that's if you can find that if you have people
01:22:54
around you your partners your colleagues your your board whatever it is that
01:23:00
give you the permission to do that again you can't just do what you want like you know if I want to like if I just want to
01:23:07
be the chef at Shopify it's not really going to add much value but if it turns out
01:23:12
and and that that the van diagram will wrap of what am I really good at what does a company value for me
01:23:18
and what is something that is uniquely in my skill set if wherever that Venn diagram overlaps if you can do that
01:23:25
you win what about in the pandemic when you're struggling did you did you have a actual
01:23:30
conversation this I'm asking this question because I'm so compelled by like when specifically with some men who are
01:23:38
often a little bit more hesitant to talk I'm compelled by this idea of like when we speak when we reach out to a friend a
01:23:45
wife a partner to say listen I'm struggling here and do we do it after do we do it during when did you do it I I did it way too
01:23:52
late I waited way too long for that and I wish I had and I think it would have saved a lot of grief um it would have I would have been
01:23:59
I don't think the pandemic was especially great for anyone all of us sort of dealt with it in our own in our own way but I think that I I made it way
01:24:05
more difficult on myself because I I was lonely and unhappy and maybe had
01:24:10
some sort of you know maybe there was I talked about anxiety but maybe there's a bit depression there as well however I
01:24:17
didn't talk to anyone about it because I didn't feel like I had the right to complain
01:24:22
I didn't feel like I had enough yeah that I had enough permission to
01:24:27
complain like there were people that were losing their jobs and they're people that were dying they were sick like I'm gonna complain about the fact
01:24:34
that like I'm a bit lonely and in hindsight I should have done it
01:24:39
differently I should have said look I recognize that I'm very fortunate very blessed but I also recognize that I'm
01:24:46
also really lonely right now and I think what that would have by by telling people that by saying it out loud you
01:24:51
know there's that whole theory about don't tell people your goals I think it's ridiculous don't tell me
01:24:58
your goals I think you tell everybody your goals because the cool part is if you have people around you that are good
01:25:03
people they're gonna hold you accountable and you may actually eat your goals way faster more effectively and it's fun to share in a celebration
01:25:09
and celebrate someone you know who deeply wanted to do something who actually ends up doing that thing
01:25:15
so it's funny because if you feel like you can't share with people people your goals it's really what you should do is get new friends totally I mean like why
01:25:22
wouldn't you want to tell your friends and the people around you you have Ambitions well the common critique of telling people your goals is that when
01:25:27
you tell someone your goal you as an individual you get something from that
01:25:33
the critique of it is you don't deserve anything by just saying something out loud that I think it's complete [ __ ]
01:25:39
I think if you want to do something and you tell put it on social media in 12 months from now I'm gonna run a marathon
01:25:44
or ultra marathon in 10 months from now I'm gonna have you know two million dollars of sales in my online store in 10 months from now I'm gonna you know do
01:25:51
something really challenging difficult especially in social media where people love to rip into each other that may
01:25:56
hold you accountable so I did not do the right thing at that particular time I hesitated and it's because of some weird
01:26:03
bravado that like I'm strong I'm capable and I'm fortunate and therefore I don't deserve to be unhappy or depressed or
01:26:10
anxious and I actually think my biggest lesson from all of that is
01:26:16
vulnerability for the right people to your point good friends good family
01:26:22
good colleagues good partners it shows strength it does not show weakness and I was very weak and I didn't want to
01:26:29
show vulnerability I wrote in my diary the other day that vulnerability is a magnet not a repellent and I think in our in our masculinity and our toxic
01:26:36
masculinity sometimes in our sense of wanting to be what we think strong is the sort of misrepresentation of
01:26:42
strength we see being vulnerable as a repellent as in I will lose things people will will leave me they'll think
01:26:49
I'm weird or weak whatever and then every time I've ran the experiment of vulnerability and when I say experiment I mean because it feels a little risky
01:26:55
sometimes it's a magnet everything almost always it's like the antidote for loneliness in many respects and there's
01:27:01
another really important thing to say because you um in that basement during the pandemic your family were there in
01:27:07
the house and we often confuse this idea of being alone with loneliness totally and Simon cynics actually I've given
01:27:14
credit he came on the podcast the other day and he said he talked about how lonely he is right now and the Brain goes you don't have any
01:27:21
friends he goes I have loads of friends I have loads of people around me I have a big team but I'm lonely there's an important distinction to make
01:27:27
um which I'm sure you can speak to me because I think where you had your family had your wife but I was like no Steve you're falling into the
01:27:33
Trap again he wasn't alone so I was not alone but I was lonely and actually this
01:27:38
is where going back to your your point earlier which is a great point about entrepreneurship being a lonely activity
01:27:44
or a lonely sport by having more people around you on the journey with you even if they're on
01:27:49
their own Journeys but they're sort of tangential to your journey it's a little bit less lonely yeah and
01:27:54
if you do that across a couple different areas of your life like if you work out at a gym or you go
01:28:00
for runs in the morning finding someone else to run with you is one thing but finding someone else to
01:28:06
run with you who's sort of going through the same like I want to run five kilometers and it's tough for me right now you do it with somebody else who also wants to run five kilometers and
01:28:12
stuff for them too there's an immediate connection there so in one case you may be not like you're
01:28:18
not alone because you have someone running with you but you're lonely another case if you're on a similar journey together and you have a shared
01:28:24
experience or you're sharing an experience that takes away from the loneliness how does that square with shopify's approach to remote working
01:28:31
because I've this is a debate I've pondered over and over and over again in my head which is like there's no correct
01:28:36
answer here we all know that everyone's got a different Mission every company's got a different Mission but one of my reasons against
01:28:44
um this total remote work scenario is because I think there's been a decay in Institute Community institutions in our
01:28:50
world so in the UK like all the pubs are shutting down we don't have community centers churches Etc work seems to be
01:28:56
one of those institutions that remains that does bring us together although that's a dangerous thing also right of course yeah and it's also age and
01:29:03
demographic specific and there's a little bit of privilege in there as well because you know everyone's situation is different this is something I'm evolving
01:29:09
on but when I'm like an 18 19 year old just left University
01:29:15
when I'm 21 years old and I've just left University I want to be do I not want to be around
01:29:20
people um to build connections to build skills for synchronous work
01:29:27
will I not be more lonely doing remote work potentially from my studio apartment in the middle of the city where I live in a cardboard box
01:29:34
um as I used to Once Upon a Time how do you square all of that together
01:29:39
so the reason that we're not fully remote is because of that exact reason we had about I don't know 10 10 or 11
01:29:47
something like that offices around the world and we were full-time in the office pre-pandemic
01:29:52
and now we sort of have this model which we refer to as digital by Design which means that office centricity is over
01:30:00
and the reason that's important for us is that we've been building this company out of Canada you know for almost two
01:30:05
decades now and so in every single job offer we gave there was an asterisk that said it's part of this offer there's a
01:30:11
condition you have to move to Canada and so that immediately limited the type of talent of the people that come to
01:30:17
Shopify and so there's a real advantage to the fact that now you can work anywhere you want so that's that's
01:30:22
that's really valuable for us first time that you know our new CFO is based in New York our new GC is based in
01:30:29
DC um our chief operating officers is is down south that is great people can live wherever
01:30:35
they want however we didn't close the offices we converted them from quote-un offices to more of these we call burst
01:30:41
bursting locations where you can come in for a burst which is just an on-site and we actually not only like the idea of
01:30:48
people coming in we've forced people to spend time with their teams in person at least once a quarter
01:30:53
and what you see is the healthiest teams um may not have to meet as regularly
01:30:58
because there's enough of a trust battery where the residue of the truss battery can be you know can be distributed but for teams that are just
01:31:05
forming it is really important for them to be in person we really encourage that so we're not really hybrid because it's
01:31:11
not three days in two days out or anything like that it's it's just work from anywhere you want with the condition that you must spend time
01:31:18
together with your team in person at least once a quarter in some cases once every month every solution every ounce
01:31:24
has a downside for sure office centricity has a downside of clear one what's the downside in your view of that
01:31:30
work from wherever you want but once a quarter uh it's that not it depends on if your manager really likes the idea of
01:31:37
being in person you're probably gonna be in person more often and if your manager does not you may be less
01:31:42
um so we're trying to work around that and create some guard rails there but I don't think there's any perfect solution
01:31:48
um a lot of companies have going the opposite way now you're hearing like Snapchat and Twitter on Twitter yeah they're all going they seem to be going
01:31:54
back to like 80 in the office Etc the good news are the bad news I don't think anyone's got this right yeah in the companies that will get it right longer
01:32:00
term are going to be the ones that are most introspective about this what's working what's not be honest about it so we know that being fully remote doesn't
01:32:06
work for us we need to be in person sometimes we also realize that it's really an amazing opportunity for
01:32:11
someone to come to Shopify who can have an incredible role building great product or doing something at the company it's very valuable and live
01:32:18
anywhere they want that is an amazing art like you know in the early days of shop I moved to Ottawa
01:32:23
Canada for Shopify and that's that's a that's a big thing for my family so the
01:32:29
fact that they can live anywhere I think is really great but I don't think anyone has really knocked it out of the park just yet um what I would also say is that
01:32:36
just back to the Simon cynic uh quote uh or or philosophy
01:32:41
I think we all need like we may not go to church as much anymore or youth groups or you know organized Sports I
01:32:49
think we all need our own version of that tribe and I think developing your own community in your own tribe even if
01:32:55
you guys sit around and stare at screens you're playing video games together I think having these rituals
01:33:01
um I'm not religious I'm Jewish but I'm not religious but every Friday night we have a Sabbath dinner Shabbat dinner and
01:33:07
we say sort of the the very basic Jewish prayers but this ritual that my kids look forward to where they you know they
01:33:14
say shabbat shalom and my wife you know makes this amazing like home-cooked dinner
01:33:19
I mean no matter what happens I'm home Friday nights even if I have to travel I'll go home then I'll leave Saturday morning because that is a ritual that I
01:33:26
think is important but I think we all need rituals in our lives and I think the cool part of rituals is like you can
01:33:31
create new ones all the time the key though is consistency and and the direction of travel at a
01:33:37
very macro level with all these things that are happening in technology seems to be um one in which
01:33:43
where we're being stripped of community and in-person connection which
01:33:49
seems to humans aren't changing technology is but our innate fundamental maslovian or like psychological needs
01:33:55
aren't changing but the society we live in I think is optimizing against our um
01:34:01
against Natural connection living in you know four white walls in the middle of a big city alone swiping on Tinder
01:34:06
ordering your food using a piece of glass screen all of these things seem to be robbing us with that connection and I reflect on this a lot I go the reason
01:34:12
why the diversity is successful and the reason why a lot of the things we've done have really worked well in terms of like the content in the media is because
01:34:18
we without really being that intentional about it to be honest have created a sense of connection for people they will
01:34:23
hear your story about your own insecurities or about the things you struggled with and that'll make them
01:34:29
feel heard and understood and connected in some way um I love that I actually think that that is one of the most this sort of
01:34:35
shared experience even if I don't know you yeah is really impactful we may not know each other we may have never met
01:34:42
before people that are watching but if you if anything that I said anything in my story resembles your own
01:34:47
or resonates with you um hopefully all I can what you take from this is that like there is a way to
01:34:54
get over some of these things some things you don't get over you simply manage it better but there's no there's no one like I
01:34:59
have not met I've got a chance to meet pretty much anyone I want just like you do nobody has it figured out nobody is 100
01:35:07
happy all the time no one has a great relationship great career great health great family we're like really no one
01:35:13
has that we're all but the best ones in my view are the ones that are self-aware
01:35:18
of where what to work on and they have tactics and tools and traits to sort of move towards a better version of
01:35:26
themselves they grab their surfboard when things come on the resiliency side they're very honest about the like when
01:35:32
they're lonely they say I'm lonely hear the changes I have to make but no one has it all figured out and I think that in itself is when I figured out when I
01:35:40
had to sort of epiphany that holy [ __ ] no one has their [ __ ] together we're all trying to figure it out in our own ways
01:35:46
it was freeing for me it's so true that nobody's there it's like a party that you're striving towards that actually
01:35:52
nobody's out you know everyone I mean you know more people than I like the people that sit in this chair that you know are way more successful than I am
01:36:00
I've listened to a lot of your your interviews we're all kind of working on our own [ __ ] yeah everyone is and the
01:36:06
ones that say that they're good I don't know I think they're lying on that point then so we've we made
01:36:13
these cards they're actually on sale on Shopify we um we use Shopify to sell these cards and it's very much I'm glad
01:36:19
you said I didn't want to say that they're called The Diary of a SEO conversation cards and um what we've
01:36:25
done is we've taken all of the questions that all of our guests have left in the famous Diary of a CEO all of the amazing
01:36:31
guests we've had on the show we've always ask them to write a question that helps people to to go a little bit deeper and we've made them into these
01:36:38
cards on the front of the cards you'll see the question and the person who wrote the question on the back you have a QR
01:36:43
code scanner you can see that the next guest that had to answer it so we're really letting the cat out of the bag here cool I picked three cards for you
01:36:50
the idea is that people will buy these and then play them at home with their friends and connect because vulnerability is the daughter connection you just have to pick one sure
01:37:01
Gary Neville tell me something you've never told anyone before
01:37:09
I don't think I'm a great father I want to be a great father but I don't
01:37:15
feel I'm a great father I feel like I only have I have like 10 units of energy and if I give you this energy somewhere
01:37:21
else then I don't give it to that and I haven't figured out the right Dynamic yet and I I worry that at some point
01:37:29
uh my kids will be too old they'll be out of the house and it'll be too late
01:37:35
and um and I really want to be a great father so
01:37:41
that's kind of it's quite a vulnerable but that's the truth um yeah
01:37:47
mission of what great father looks like is maybe not fitting the great father that you are
01:37:53
um potentially uh you see what I mean by that yeah I I do um because you're an
01:37:58
inspiration so I mean this goes back to am I am I enough of enough of a father am I enough right
01:38:03
um but the thing about the the like being a great father is
01:38:09
there is a limited time component to it I don't know how much like Bailey is six in 12 years she's going to be off out of
01:38:16
the house somewhere I suspect I got 12 years to become a great father and
01:38:22
I don't know exactly the right path to get there I I know what my weaknesses
01:38:27
are but they're a little bit elusive it's it's am I present with them am I mindful to their needs
01:38:32
um but that's something that that I I struggle with and I'd like to
01:38:37
be if I sort of think of a three or four things elements in my life that I want to be world class my work
01:38:43
um my relationship to Lindsay my contribution to the world a charity perspective that fourth bucket is is can
01:38:50
I be a really great dad and and I don't also know how to gauge that a lot of the other metrics I can gauge Lindsay was
01:38:58
very clear to say like you're a great husband or like you weren't a great husband this week my work can be reflected by my
01:39:04
performance I don't think the stock price is exactly directly you know I don't think they're I think that's more
01:39:10
um correlation versus causation but the other points in my life my contributions to the community I can measure those
01:39:15
things I don't know if I can measure if I'm a great father or not because of that it makes the whole thing
01:39:21
really challenging maybe like the other things we've spoken about this great father party is a party
01:39:27
that nobody's at potentially um I've never met someone that says I am
01:39:33
a great father yeah you may be right um now maybe actually
01:39:39
the pursuit of that is in itself what I'm trying to do
01:39:44
as is the case with the life right right exactly exactly right um
01:39:49
but by the way even like okay go back to vulnerability millions of people are going to watch this and maybe there is someone who's
01:39:56
watching that actually it's like hey I actually think I am a great father and here are the couple things that I use to gauge that interesting how my you know
01:40:03
one of my uh a friend of mine who he's not really my parent role model but maybe he comes out at some point I asked
01:40:09
him what a great father or great parent does and he says one thing Independence are your children able to
01:40:16
be truly independent I thought that was really interesting as sort of a metric for gauging whether or not you've raised
01:40:23
you you you're a good parent um another one says like you know there's a famous quote which is you're
01:40:29
only as happy as your least happy child um I've actually heard the corporate
01:40:35
version that which is like your only successful is your least successful division of your company which is also really interesting way to
01:40:41
kind of put that um but I I that would sort of be the one that that I don't think I've admitted that because
01:40:48
um I haven't really had a venue to actually say something like that before we have a closing tradition on this podcast where the last guest asks a
01:40:54
question for the next guest we'll see that's what becomes these conversation cards um the question that's been left for you interesting one because it's a
01:40:59
bit left field but what's a common misconception people have about you
01:41:05
and more importantly how does it make you feel
01:41:11
because I talk so much about entrepreneurship there is I've heard this now from a number of people that um
01:41:20
I don't ever talk about the failures that I've had from a business perspective
01:41:25
and partially I don't do that because I don't think it's they're they're necessarily that valuable relative to
01:41:31
some of the successes we talk about DJing and t-shirts and and Shopify there are literally 20 other companies that
01:41:37
I've started that have been total [ __ ] failures and I think the common misconception is
01:41:43
that the stuff that I've worked on have all been not huge success but generally successful because I talk about them so
01:41:49
much and I it makes me feel sometimes like
01:41:54
I'm not more recently that I'm not being as helpful or honest as I as I should be
01:42:01
because I just don't have I don't have the space or the venue to talk about the slipper company the poker
01:42:07
chip company the nurse uniform company like those are all real companies that I started when I was in college or
01:42:12
undergrad or when I was a teenager that failed miserably and the misconception is that I I think
01:42:19
that that everything that I've worked on has turned out to be good or successful when you look at yourself in the mirror
01:42:24
and that's I'm just saying that as a metaphor and then you look at the perception of you does that create a certain dissonance or a feeling of like
01:42:33
I don't know people call it imposter syndrome which is the time I don't love but you know often when you become when you reach high places because you're
01:42:39
involved in very successful Ventures and Pursuits there's this kind of like perception which might not match the
01:42:45
perception or the voice that Whispers in your head when you're alone I have I have that so here's another way to put
01:42:51
sort of the the failure thing um I do a lot of TV and and
01:42:56
um and I'll get feedback that you know that was really great I saw you in the show
01:43:01
where I saw you do this interview or saw you on on on Squawk Box um and I'm like great yeah thanks you
01:43:07
know I appreciate the common stuff um sometimes I want to tell them I don't often tell them do you know that I put
01:43:13
in five hours of work memorizing those data points I think sometimes I like to
01:43:19
pretend like it comes easy to me it does not come easy to me I work
01:43:24
really really hard in my craft my if you think I'm a good Storyteller you don't think I'm good story like I put a
01:43:30
lot of time into preparing for my conversation with you today a lot of time I've watched all your interviews I
01:43:36
literally as I told you like I I didn't finish my run until I listened to the entire Seth Rogen interview um
01:43:42
I don't think I do have I don't I do a disservice I think to a lot of people and I'm working on this already around
01:43:47
vulnerability of actually sharing this is not easy for me I'm not naturally I can naturally memorize I'm
01:43:54
not I don't have a photographic memory what I do have is a really good work ethic and I should be talking more about
01:43:59
that than actually showing my work more than just the result of my work so when I look in the mirror and I think to
01:44:05
myself where is the dissonance it's that sometimes less less recently but but certainly
01:44:11
often time previously in the past years I've made it seem like this is easy for
01:44:16
me and it's not easy for me and I was never the smartest kid in any
01:44:22
of my classes I never got I probably made it seem like I was you know smarter than I was in the classes
01:44:28
when I wanted to do on a class I just outworked everybody else and I think if if you should if anyone
01:44:35
out there wants to emulate anything that I've done emulate my work ethic
01:44:40
and the journey not the destination because it's been [ __ ] hard and still [ __ ] hard and I I embrace it and I
01:44:47
enjoy it and I I wouldn't trade for anything else in the world but
01:44:54
I've had tons of failures and I work really hard to make sure that I fewer of those over time but it doesn't come easy
01:45:00
to me Holly thank you so much incredibly enjoyable conversation I've learned so much but I've
01:45:06
um it's funny though I've done this I've done so many of these podcasts and I still continue to learn from every single individual and so many incredibly
01:45:11
unique and and um for me really defining ways I wanted to close with just one
01:45:17
thing because I think I'm thinking forward at the guest we've got coming up and the guests we've had previously and
01:45:22
maybe you're the guest best place to answer this this started as a very business-centric Show Business Centric
01:45:28
podcast started as a me as a young entrepreneur building a company et cetera Etc there's a huge part of my audience base
01:45:35
that are doing exactly that right now like they're like maybe they've started their Shopify store
01:45:41
um maybe it's day one they know what they want to sell maybe they don't maybe they're not quite there yet
01:45:46
but if there were a piece of advice you could lend to someone who wants to go on that journey of Entrepreneurship of all
01:45:52
the things we've discussed today what would that closing remark be remember
01:45:57
that the cost of failure right now is the lowest it's ever been in the history
01:46:02
of the world and because you if you if you can remember that it means that
01:46:08
there's absolutely no reason why you shouldn't keep trying and if it doesn't actually work try something else
01:46:15
I think this idea of cost of failure is a fascinating one because it's never going to be zero right because ultimately like there is an opportunity
01:46:21
costing your time you could be doing something else you could be watching TV you could be playing video game you could have a job
01:46:27
but knowing that you are interested in entrepreneurship and at the same time in
01:46:33
modern day you also realize that the cost of failure is as close to zero as it's ever been means that if you have
01:46:39
any instinct to start a business in the shower when you're driving when you're on a walk randomly you have this like
01:46:44
this would be a cool idea try it when you look across the millions of stores on Shopify who've now sold more than
01:46:52
half a trillion dollars on Shopify the vast majority of them
01:46:57
did not wake up and say I'm going to be a great entrepreneur they tried something it worked they scaled it they
01:47:03
tried something it didn't work they tried something else that was one when they scale when you look across the stores on shop that have been successful
01:47:09
all of them didn't start out with this this vision of building a billion dollar company at some point and I think that
01:47:16
the fact that we can start a business now for the price of a couple cups of coffee and that business can grow to be
01:47:22
a large multinational multi-billion dollar company if that's what you want
01:47:27
that did not happen and it certainly did not happen in the time span that's
01:47:32
happening right now the companies now there's there are companies on shop like today where they're doing a billion dollars or
01:47:39
more in sales that didn't exist six years ago six years ago was a shower idea and now they're a multi-billion
01:47:46
dollar company or if you don't care about building a billion dollar company they've changed their entire vertical
01:47:51
their entire the the their world whatever that their whatever the world they're in they've changed it entirely
01:47:57
and it'll never be the same again and so what a time to be alive what a time to be alive what a time to be
01:48:03
someone who actually has an idea and wants to share that idea with the world and if you're not sure about an idea
01:48:09
what you could sell how you could start think about something you already do there is a store on Shopify that sells
01:48:15
the most delicious matzo ball soup is a is a Jewish chicken soup okay um
01:48:20
it's just matzo ball it's like a uh if you go to Jewish deli you should actually try this there's a store in shopline this is matzo ball soups and
01:48:27
when you look at the story of how of how it got there they were just making matzo ball soup for their friends and family and at some point they realize maybe I
01:48:33
can share this with the world and they do and now they have a real business doing the thing they already were doing except now someone is paying
01:48:40
them for that that is incredible and that's the time we're living right now what a time to be alive Harley thank you so much for your
01:48:46
time and your generosity it means the world to me it's been an incredibly important conversation great conversation thank you for inviting me
01:48:52
[Music] over the last couple of how long maybe four months I've been changing my diet
01:48:59
shall I say many of you have really been paying attention to this podcast will know why I've sat here with some
01:49:04
incredible Health experts and one of the things that's really come through for me which has caused a big change in my life is the need for us to have these
01:49:12
superfoods these green Foods these vegetables and then a company I love so
01:49:17
much and the company I'm an investor in and then a company that sponsors this podcast and I'm on the board of recently
01:49:23
announced a new product which absolutely spoke to exactly where I was in my life and that is huel and they announced
01:49:29
Daily Greens Daily Greens is a product that contains 91 superfoods nutrients
01:49:35
and plant-based ingredients which helps me meet that dietary requirement with the convenience that he will these
01:49:42
offers unfortunately it's only currently available in the US but I hope pray that it'll be with you guys in the
01:49:49
UK too so if you're in the US check it out it's an incredible product I've been having it here in La for the last couple of weeks and it's a game changer
01:49:55
[Music]
01:50:16
oh
