Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee! E245

one of the greatest hacks for being an ambitious hard driving entrepreneur and that's why it's Kylie Jenner is nothing short of burlesque Harley Finkelstein he's the president of Shopify one of the largest e-commerce platforms worth over 60 billion dollars he's helped scale brands worldwide and he's now on a mission to help you start your own business about a month into college I got a call from my mom and said Dad's been arrested and he's going to jail college is over and I was shifted into this survival mode I had no choice and it's a very

powerful driver I met Toby around that time the initial idea had lots of other competitors this was not 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 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 because they think they have no choice no one had this massive 80-page business plan and then got started that's not how 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 that's how you build companies that changed the world I wake up every morning encouraging more entrepreneurship creating tools that help entrepreneurs start scale and build faster that drives me to keep building and keep growing the stores that we are 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 in I would definitely put one of those millions of

dollars into the hands of a Creator who's the second one I think would be the third one would be someone oh really yeah those are the types of people that I would back would you like to go for dinner with me and my guests here on the diver CEO we are holding dinner parties all around the world over the coming months and our subscribers on this YouTube channel are invited we're inviting 20 subscribers to 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 all you've got to do is hit the Subscribe button and I hope to see you at dinner somewhere around the world very soon [Music] Polly in your own words who are you what do you do and what mission are you on I've always self-identified as an entrepreneur full stop 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 Entrepreneurship what do I do um I mean I think technically I'm the president of Shopify but I

view my role as being the chief Storyteller how can I get the world to know that Shopify is 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 want more people to try their hand at this thing that that I call business creation or entrepreneurship and I don't think right now most people consider entrepreneurship as a thing that they can do to self-actualize why does it matter if they if more people become entrepreneurs I think the world is far

more colorful and I think humans are far more interesting when they commercialize their hobby for example I 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 and that was the case for a long time you go back 40 years 50 years not everyone could be an entrepreneur 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 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 or their kitchen table and they Tinker on cool stuff but they don't share that with the world if they did that consumers would get really better stuff that they can purchase and they can use but those particular people behind those businesses can find their life's work and this concept of life's work is not something that my parents my grandparents my great-grandparents even had in their lexicon but I think the idea of finding 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 there's going to be potentially millions of people listening to this now that resonate with what you're saying they are in situations that are not serving them on some kind of psychological fulfillment level um why aren't those people in your view pursuing what their life work is I'm trying to like create some I guess some Nuance or trying to step into their mindset so that they feel understood what is the the the Gap the Grand Canyon

that they need to cross in their mind to get to that other side which is their life's work why don't people do it I think a big part of it is perception I think a lot of people perceive entrepreneurship as something that's Out Of Reach for usually one of two reasons the first reason is is financial they have a family member or a friend or they've heard an anecdote of someone who started a business that was not successful and ultimately it cost them 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 expensive if you don't have money you cannot start and actually I would say that for vast majority of the time that entrepreneurship or business has been available in the world which is you know entrepreneurship business is about as old as currency so thousands and thousands of years the main ingredient in starting a business was capital and if you didn't 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

the understanding or the experience or the know-how to begin and I think that also has changed I think now you don't 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 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 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 can try

it again and that may be you know your gym shark your aloe yoga you're James purse from a psychological perspective some people you know they often say well you know it requires a lot of self-belief they talk about self-belief and confidence as being this kind of macro 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 and he was saying to me he said something to me like when the it's actually pain the pain of his current situation which

drove him to take the leap as it relates to people's like psychology and their self-belief and their self-confidence um when you're trying to get people to become entrepreneurs what can we do there to get them to take the leap is there anything that can be done I mean first of all I think that there's two types of catalysts for starting a business one is passion and the other is disparity or being desperate and actually I think entrepreneurs by necessity are a big part of the the 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 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 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 famous line scroo just do it I think that plays in sort of the passion side of things not necessarily 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 either have to like move back home to South Florida and live at home with my mom and my mom 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 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 and that thing that matters the role of passion in entrepreneurship you know you'll you'll know

that a lot of entrepreneurs they are so um in love with the idea of being rich and successful that they'll kind of try and reverse engineer a passion into this their Journey being rich and successful 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 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 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 one you're gonna quit all of these things what role do you think passion plays an eventual success I think you 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 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 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 remember seeing the DJs at these parties on stage playing I don't know cheesy 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 group of 300 sleepy people eating rubber chicken dinner and like a minute later a 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 there was a passion for me to I want to be a DJ turned out nobody would hire me because I wasn't 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 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 would just start my own DJ company and hire myself so there's some passion

to it when I was 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 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 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 much younger sisters mom needs help what am I gonna do and I started selling T-shirts to universities across

Canada I had very little passion towards t-shirts I like wearing t-shirts as we talked about earlier like black t-shirts are something that I like but I was not a passionate t-shirt entrepreneur manufacturer I was passionate about survival I was passionate about supporting my mom and my sisters and so I don't think that t-shirt business was 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 fast forward until today leading Shopify with with our team I'm very passionate with shopify's Mission this idea

that more people can be entrepreneurs because of the work we do at Shopify I can do this the rest of my life if if the board will have me um so I think there's a time and a place 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 thought were quite interesting and that made my mind wander onto um adjacent subject matter one of those is that you're talking there about what's driving us at different moments in our life one of the um

conversations I had on this podcast with Barbara Cochrane the shark over here in the US uh she said to me that her best investments she makes in entrepreneurs they tend to have some kind of underlying trauma and and that ends up being fuel in their engine so when things get 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 and shame and these kinds of things are unbelievably unappreciated drivers and people For Better or For Worse it comes with a

downside um do you think entrepreneurs should and Founders should go to therapy uh I think some should I think entrepreneurs and Founders need to be self-aware I think that that's the first thing once they're self-aware and they understand hey there are some things 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 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 people do it through books

and they did through meditation and they go do you know Ayahuasca in a in a desert somewhere but I think if you have if you have the means to go to therapy how could you not there is someone whose 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 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 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 or it's something like a therapist or a psychologist in your life or psychiatrist you need to find the right fit but if you have the means to do so it just it's the greatest hack ever to just know more to realize more is it going to be painful unequivocally the joke that I have with with my therapist is I know 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 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 like oh my God I'm still like I'm still such a work in progress you know one but but that's I think what we're all choosing here there's this great my favorite poem or speech ever is this Teddy Roosevelt speech the man in the arena did you know it no I'm gonna butcher it but it's effective 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 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 Critic you can be a spectator but if you're an entrepreneur or you're you're a doer or a builder or someone that deeply wants to do cool [ __ ] and build something for yourself for your family for the world you got to be in 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 the reason why the best articulation of all this is is this term entrepreneurship because entrepreneurship is fundamentally you have a problem and you were solving in a way that uses the least amount of resources but has the highest amount of output and that's the reason why I love entrepreneurship I love we have millions of stores on Shopify some of them started because they were passionate about commercializing their their craft in some cases they started because they had no

choice but the end result is they built something that is of value and they've shared it with everybody else 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 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 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 um and I think

therapy helps with that what's your relationship like with failure we talked a little bit about the 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 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 build great products you have to fail fast um but if you're struggling with you know enoughness then it seems like that might limit your ability to want to fail fast

you know it it is certain that the more the more successes you have on your belt the easier it is to fail because you 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 think separating like you being a failure versus the project or the the particular thing being a failure is very 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 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 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 made failure totally different so now it's no longer about failing it's like what did I actually get from that that's going to make it better the next time and Shopify puts out a lot of products we 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 industry we do like our spring collection and our winter collection so we do these things called editions where we put out all of the products and features we built over the last six months we do about a hundred of them each time which is a lot not every one of them is going to be a huge success but some of those will be a complete game changer for our business but also in the lives of the

people that use our 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 responsibilities or new roles am I going to be a failure and and the best example I can give you is for about five years or so I was shoplife's Chief Operating Officer and I don't think I was ever the most operationally minded person meaning I didn't necessarily live in the details I didn't necessarily live in spreadsheets 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 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 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 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 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 there's this other role which traditionally is called the president role which is very external facing 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 can actually be spiky and instead of actually trying to be a well-rounded leader maybe I can focus

on sharpening that point and sharpening that point over and over again and that's when you know I had a conversation with with Toby 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 would be to be a great Chief Operating Officer I mean we have that now but man Steve I did not want to admit that I was not the right CEO for Shopify because ego right total and and ego and 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 sort of began to be honest about is this the right role for me that I began to say hey there's this other 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 it is so much more meaningful for me to have this role today because I feel like this is really where Shopify will benefit the most from what is my superpower which is really storytelling and the company's

better I like it better the currency was so much better than I was ever everything kind of came came about but it took it probably took too long I I think that story is an incredibly 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 role um maybe they're being offered a promotion into another role and because it's a bigger role with a bigger salary they are inclined to take it but there's that missing pause of sort

of self-awareness where you've got your ego 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 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 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 point of self-awareness is so incredible I

I reflect on a guy called Pete who I offered a promotion to one day and he was like no I'm not ready this must have been like what what I'm offering you more money the chance to become a director in the business and 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 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 yeah I like

Pete Pete is the happiest guy I know he has his [ __ ] together way more 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 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 track and so the upward mobility of your career ended up being you actually at some point if you're really good stop 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 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 if you want to be an incredible senior independent contributor because in your IC we will pay you the same rate that we would pay a senior manager and that if you actually like your craft whether you're a developer or a marketer or a salesperson or you're you're you're doing um data analysis or a data scientist if

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 be a manager to get some sort of additional seniority or additional compensation and dispelling some of that frankly like the [ __ ] around the only way to be successful is to be a manager is to lead people not everyone needs to lead people some people should be a coach other people should just continue becoming like the greatest 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 need to talk about that you sort of raise it that that that got me thinking about like the self-identity thing is that I think a lot of times for this guy Pete Pete may really just be ambitious about perfecting his craft and his skill set and he doesn't necessarily believe he's ready yet to leave that because there's 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 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 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 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 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 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 customers are going to be happier it all kind of works out I think most companies turn their employees ultimately into 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 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 one thing for me is the storytelling aspect of my job is making sure investors the public are Merchants media 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 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 at Shopify so I understand all those things because I need to tell speak to it intelligently

and with conviction and with a deep understanding but I'm never going to write code because there are people that should write code that are 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 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 CEO and I remember where I sat when he said and what I recall is he was

referencing that he still felt that 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 offering him because he didn't feel like he'd quite finished the work in his current role which was just in the UK um you reference spikiness you know you said you and that gave me 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 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 it important oh so this is going to be uh a long-window way to get there but I think it's important um I um when I was building that t-shirt business in college a mentor of mine say his name his name is Philip Reimer he's a senior partner at a very prestigious law firm called 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 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 skill set that you need given what I think your Ambitions are around business creation business building entrepreneurship you are lacking some sophistication you're you're always going to struggle with these sort of things he's like but I have this idea which is go to law school not to get good grades necessarily not to get not to become a lawyer but to effectively selfishly disseminate all this information from

your classes to make you a better entrepreneur and I think because I sort of had a very 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 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 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 sharpen your point you should do something

that is not obvious and in hindsight it really feels like what Phil was helping me to figure out was finding more Alpha in terms of Entrepreneurship finding some Arbitrage opportunity something that that is that exists that no one is looking at but that I can take 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 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 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 your curriculum in deriving as much insight as possible so when you leave Law School you can return to entrepreneurship in a much better version of yourself because you'll have something that the competitor set other 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 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 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 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 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 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 real critical debate and critical reasoning I learned how to read 2 000 pages and pick up the one line that matters all these things on their own doesn't seem like it would create the curriculum of a great long-term 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 didn't know exactly what my spiky point was but it felt like it's it's definitely

in the realm of Entrepreneurship I didn't realize that I I would help build a company that would create millions of new entrepreneurs but I knew entrepreneurship was deeply personal to me because it helped me it was my family Story of Survival it just felt like this incredible tool that that most people had not discovered yet and so on that spiky point I think the 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 was deeply important to

me and so as I made decisions starting at 21 years old every decision was under the lens of is this going to help sharpen my my my points is this going to make me a better entrepreneur and I think if I would have realized that 10 or 15 years later um it still would have been fine but it 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 of you know a handful of really smart Engineers building this crazy piece of software

called Shopify 14 years ago I think this is an exceptionally un under spoken about point which is this idea of like skill stacking but stacking skills that are unobvious and rare within an industry so if we take and I think we should go through this in a little bit more detail because I think it can really have a profound impact on people I read about how um the best people in 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 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 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 that particular thing like Cristiano Ronaldo the football player he's not the best he's not the fastest player in the 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 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 10 of various things I think about Jack he records this podcast now if Jack was uh wanted to be a podcast director what all podcast directors or producers do is they'll go learn how to do microphones and cameras now interestingly I don't 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 Jobs he went into

typography and design and then made these beautiful devices which actually probably go and try and get an unobvious but I skill that would be in high demand and low Supply in this industry so if Jack went into theater he would learn maybe about how to construct a story arc or if he went and did like I don't know is that set design also yeah or DJing he went and learned to be a DJ then he would learn about stems and musics and whatever else or set design if he went 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 would make them be a real [ __ ] hard to find talent but it's funny because we can in Industries like I always think this about um coders and I don't hate to sort of generalize here but it probably doesn't sound like a generalization um it's sometimes hard to find someone who can code who's also an exceptional Storyteller and visionary often in companies they're two separate roles right so if you're if you're a coder instead of becoming even better

at coding for example going and doing those little like public speaking sessions is probably an unbelievable hack because then you can build and sell sure and actually that brings up two points one is most people start companies with people just like them yeah yeah most people start companies of people that they would have been friends with in high school I think that's a terrible idea in fact if you are in college right 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 sitting next to you walk across the street go to a different faculty go to faculty of Arts or the faculty of philosophy or the faculty of engineering and find someone there to start a company with I think some of the best Partnerships and relationships that I've seen that have built things that are that change the world from a company perspective philanthropically whatever the whatever they're trying to build might be building with other people with complementary skill sets is incredibly valuable in fact I think you get a much richer set of stacking of skills you

mentioned DJing in terms of skill set I never appreciated ever how important my experience DJ and teaches like hundreds and hundreds of bar mitzvahs over my time hundreds I 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 there's all these different things so for example something I noticed early on it's like 14 or 15 years old if the pre-meeting went really well with the clients no matter how the party went it was going to be a great result because I

had a good relationship a good connection with the client even if half the party didn't want to dance the 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 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 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 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 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 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 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 resonate oh they really like this song great I'm gonna go like Mo Money Mo Problems from Notorious B.I.G and the whole crowd erupts things like that really do make a difference um you know there is instead of asking people to get up from their chairs and come onto the Dance Floor which is an awkward thing to ask people to do after dinner instead have something in the middle of the dance where the people want to see so maybe for example one of the people that is

hosting makes a speech and you say ladies and gentlemen at this point please please get up in your chairs and take 10 steps forward because the Father of the Bride is gonna say a few words and everyone gets up and comes on the dance floor and then when that speech is done everyone's already on the dance floor and so finding these hacks and these these sort of ways to um not manipulate but but but find better strategies for getting the thing accomplished I learned all that in DJing and I can apply all that to running

a large public company today this um you know when we start businesses and stuff go back to that point again like we we tend to go deep on the subject matter but what I've heard from that is our hobbies and the things and the Curiosity we have outside of the area that we're building in is equally important then like if I'm building up like I don't know if I'm building a um I'm building mugs for people to drink tea out of 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 thing but taking a step away from the painting allows us to see the picture a bit clearer and also to to create that 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 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 understand a

lot of hair and pulls those different things in my um what's the polymath sorry uh polymath is someone who knows a lot about a lot of different things okay now there are two things that I've done that were hobbies that ended up being hugely valuable is one my wife started an ice cream company in 2016 after we had our first daughter uh after our first child my wife really wanted to start an ice cream shop in our in our in our neighborhood there was an ice cream shop and so it was clear it was her

business not mine she was very clear about that she wanted Independence but even just helping her on things like accounting or um accounts payable or accounts receivable or helping your procure ice cream from the ice cream makers that was super valuable because one it built huge empathy for the people that you shop that are starting out the second thing I did was um during the pandemic I was all by myself I'm an extrovert as as you probably can tell 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 drinking so much more coffee when I was by myself at home way more like double or even triple the consumption and my best friend um who's a sort of a Teague you know T guy loves tea said to me I'm gonna actually get you to stop drinking coffee in the afternoon and replace your coffee with really great green tea I wasn't really a tea drinker and so David started to bring me this great tea and at some point I was like you know David I want to actually

experiment with more of the features on Shopify and I think 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 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 for when to drink it and so we created this this little tea business called fire belly and both both those things 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 different business ideas both those things have made me as a leader Shopify so much more valuable I understand pretty much every feature and functionality that Shopify has because I tried for myself and initially when I told people that I was starting a little tea business the answer was I don't like why are you doing that that seems silly you're not going to change your life financially it feels like a distraction and I would say 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 Shopify and it's just a hobby there's something really really powerful in that 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 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 of Mount Everest looking out thinking Jesus Christ like I've got to find a website as you

said I think I need loads 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 branding and I need to do it all now and and also there's this other thing which in our minds we think of success as being me making millions or me making a ton of money what what I almost heard as you're telling that t-story was like have this passion 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 just get going and you'll you'll stumble forward along the way and and that's okay I think if more entrepreneurs could see that Mount Everest there's just a bunch of Pebbles and there's and remove the time frame where possible remove the expectation of huge success and just stumble forward through the process we'd have so many great great more businesses 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 know coffee or matcha or whatever it is that perspective change of like okay well today I'm going to start my Shopify 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 and see where we get to in 10 years most people on Shopify don't register their business until weeks after they sign up for Shopify so most people don't even assume they're going to need to register a business and 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 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 try it out like I mean this isn't a pitch for Shopify but like it's it's less than a couple Starbucks 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 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 doesn't work you try something different but this idea of yeah there's like this barrier to getting started and I think you know one of the reasons that I think one of the best times to start your entrepreneurial career or your entrepreneurial you know business isn't isn't School the reason I think is 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 to get started whether you're in high school like with my DJ business or in college with my with when I sold t-shirts there was very little expectation on me no one thought it was going to be successful anyway you still want 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 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 and this is sort of your side Hustle the amount of people shop by right now is about 10 of all e-commerce in the United States in places like Australia it's even way more than that um I know most of our largest Merchants because I'm obsessed with this stuff I love it most of the businesses on Shopify that are really successful the Homegrown success stories they were accidental it was Heather and Sharina sitting at a coffee shop not too far from here with a friend of theirs I was a doctor who was wearing

these hospital scrubs that just looked like [ __ ] they're like we can do this better and that's what figs was born it was Ben Francis who said why is there no clothes for just regular gym people either it's like gym rat stuff like bodybuilders or 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 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 no one

had this massive 80-page business plan and then got started that's not how businesses are created in modern times they're created based on this nugget of an idea and they're explored and you have and you get curious about you try this other stuff and that's how you build companies that are long lasting that change the [ __ ] world and that's how Shopify was started as well indeed indeed it was an immigrant from Germany 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 he didn't have his working papers and was told he can start a business and he looks around and he sees snow everywhere and he says I'm going to start a snowboard company and in 2004 there's two ways to sell a product on the Internet one way you sell them in a Marketplace which is very cheap very inexpensive like eBay or something exactly but you're renting customers from that Marketplace they're not your customers the other way was to spend seven figures no exaggeration and have one of these big Enterprise companies build you an online

store I didn't have that kind of money he didn't like those options so you wrote a piece of software and started selling snowboards and the snowboard shop was called snow devil and very quickly people started asking him if they can 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 shop I was born and I met Toby around that time when he was transitioning from snowboards into software and I became one of the first customers to

do Shopify in 2006. and then you were the first non-technical employee as well that's right yeah and a couple years later after Law School uh I called him and said I want to join 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 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 I'll form Partnerships I'll do uh I'll do anything and everything you need because I

believe the world will be 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 when people hear their stories of these you know couple of a couple of women a couple of men a 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 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 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 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 head than me and probably better capitalize better capitalized information that's right yeah smarter yeah all those things and it never has mattered and I I can't quite articulate why it doesn't matter I could probably try but I want you

to um when Toby that small group of people yourself went off on that Journey was their competitors totally tons very well big ones too Yahoo stores no idea in 2006 Yahoo is a really big company Yahoo stores existed there were companies called Magento which isn't still around today uh yeah not not as prevalent but that was around there were major competitors out there but the idea wasn't necessarily to to try to do something no one else was doing it was try to do it better and that I think is the difference between the great companies

and and just the good companies that there are always going to be good companies out there but most of them are not necessarily trying to completely you know like move the needle on like what is possible um all of those companies by the way that existed when Shopify was just getting started served a particular segment it was either for you know like arts and crafts like an Etsy kind of style or for big companies IBM sap Oracle had competitors there uh Yahoo store is focused on very very small businesses but we never gave ourselves those

constraints it was let's allow people and enable them to build beautiful online stores quickly effectively that were customized for their particular brand and and try to bend the learning curve around entrepreneurship and over time like over many you know oh it's it's now almost 20 years over time we're like let's add payments let's add Capital Let's help with fulfillment we should do point of sale because physical 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 them manage their

cash flow over time it sort of evolved from that but the initial idea had lots of other competitors in the space this was not this massive novel thing we just did it better and it's funny because a lot of 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 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 winners and

losers are established so that begs the question how what's the philosophy and I'm very 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 better I mean it's gonna sound trade but but you know having deep empathy for health 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 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 that the all of the merchants that I brought up so far in our conversation were Merchants that started at their mom's kitchen table that grew to be multi-billion dollar you know hegemonic um incumbents 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 Decker and Mattel using Shopify but but those are companies that were already successful before they started using Shopify the stores that we are

most proud of that we love to talk about are the Homegrown success stories because even though we are not responsible for their success we simply made the journey a little bit less difficult over time 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 doing by adding more value A dispatch amount of value every single step of the way we think we build a lot of loyalty with our merchants and that what then happens is the ones that do become

successful never leave Shopify so there are people that start a business that that fails um and and they decide to either shut it 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 multi-millionaire companies over time but key for us is that the ones that do succeed never have to leave the platform 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 online store but

over time as the complexity of your business increases the solutions on Shopify sort of reveals itself over time but it does so at the right time so you are not overwhelmed and I think we are very hard on ourselves and I mean that's the right term we're hard on ourselves that we really want to 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 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 very cool technology what is it going to do for merchants what is the Practical implications of AI on the lives of of the merchants and for us was like well wouldn't be cool if AI helped Merchants write product descriptions so you you put in your product photography or some meta tags and chat gbt helps you write a product description that will convert better that is really practical 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 we can do token gated Commerce so that you can reward your most loyal customers with new opportunities new discounts new events we use this lens of of of practicality across every single feature we have and 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 um my Moby Dick in terms of Shopify the the one brand Merchant that I've wanted on Shopify for so damn long is a company called Supreme they're

incredible the Supreme story is amazing but the reason I wanted Supreme on Shopify so badly more than almost every other any other brand um is because I knew that they would test the limits of Shopify their flash sales are probably the largest flash sales across the entire internet which means they're probably the largest flash sales across all of retail and I knew that if we got them on it would pull Shopify into a new category of resiliency of performance most companies would have shot away from that most companies have been like we 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 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 handle anything else and there's a little bit of like a there's a great book by Nissim tele called anti-fragile 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 there are three systems there's the

fragile system I take this glass I drop it it breaks there's a robust system I 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 it actually rebuilds itself better stronger faster and shopify's fundamentally an anti-fragile company and I think you your companies are the same way you guys invite what called pain called challenge because ultimately you want to come out the other side better and most companies like literally 95 percent of companies out there maybe more don't want that pain

they want to be copacetic and they want to continue the status quo really interesting you know I I mean my 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 leave because we're bringing too much traffic so that provider is never going to have incredibly sexual successful 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 were like complaining

about us they were like shame on this shame on them yeah so we we moved to a different um someone 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 too successful am I right jack I want to make sure I'm correct because you dealt with them yeah 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 them in in different directions as

opposed to the best companies Embrace 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 not just something for companies also for human beings I think all the stuff we talked about about my upbringing made me better Made Me Stronger do I wish if those things wouldn't have happened potentially I mean in hindsight I wish I would have had less anxiety maybe but maybe I would be sitting here with with you Steve today if those things wouldn't 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 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 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 just got comfortable with with what we're doing now Harley and now you're telling me to so do you

how do you create that culture that Fosters that sense of like resiliency and positive attitude towards change okay two things one is resiliency can be taught you're not born resilient you can actually learn resiliency you can learn from your 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 fact I think people the most interesting people that I know that are resilient have had something happen to them that allowed them to build resilience on their own some of them

you know cracked but others actually it's like you know the the the metaphor that I love to use like a huge tidal wave is coming some people grab their surfboards and some people run for the beach get the towel I like to surfboard people the surfboard people are my people those are the entrepreneurs in terms of how we do it at Shopify is Shopify as a company building software for entrepreneurs that is built by entrepreneurs the like the amount of people at Shopify who had a business have a business are about to start a 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 actually rather than on doing their own Ventures we are collectively coming together to build something much bigger together like one plus one equals ten um and I think one of the ways that you Foster a culture of resiliency is look for the entrepreneurs the reason I met Toby in 2005 was I moved to Ottawa to go 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 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 hang out and I found this coffee shop with five other entrepreneurs who every Friday night got together and spent time learning from each other and sharing War Stories and sharing tactics and that became my tribe one of those entrepreneurs was Toby so I love entrepreneurial people I love resilient people and so you can search those people out when

you're building your company or trying to create a culture that is you know super effective that has it looks for it looks for the alpha opportunities that is very ambitious that works hard invite entrepreneurs into your company create an environment that entrepreneurs want to be there and and I think that's 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 they're either entrepreneurs or aspiring entrepreneurs but every single person at Shopify is very entrepreneurial and it's the same reason where you told

me a story earlier About You Know Jack taking a photo of 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 entrepreneurial way to do it the non-entrepreneur way to do it is to be like yeah we need some books you have the exact same books behind you here as you do in London most people won't notice that but I noticed the amount of attention and to detail you have and the care you've taken that every that that

b is exactly 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 invite more of those people into your life do you think as well though that 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 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 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 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 become the culture the cultures if they went somewhere else they'd probably behave differently and but that comes down to the culture just being absolutely crystal clear and the hiring of that culture being disciplined and the firing yeah I mean 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 company the culture should change slightly and hopefully it gets better over time but I think there's a lot of companies that they put a a poster of an eagle up on the wall that says leadership underneath and they call that culture or they say you know they're famously Patty McCormick created what's what's now damn soon as the Netflix culture guide yeah I remember and what was cool about that was

the talent team recruiting team at Netflix gave out this culture guide in advance of you even applying to Netflix it was a public document so you can read this and if 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 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 uh Superior Severance I love that right it's super super cool so

there's there's that aspect which I think is is really interesting but I think the culture should continue to 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 I think it's [ __ ] like this is a better version of Shopify right now than we've ever had our team is better our leaders are better yeah there's some Romanticism about the early days where 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 floors ourselves but I actually think over time you can have a fat if you like part of this is like is your company founder-led or professionally managed and those are fine things but it I don't actually think you need to actually have a Founder there to be to have a Founder mindset I think you actually need to have if your culture is strong and people do the right thing when no one is watching and people are constantly challenging each other and people are

constantly trying to like pull the product in in a really unique positive way that's a place where more people like us want to work and therefore other people like us want to work as well and that's why I love the idea of like building a company for entrepreneurs built by entrepreneurs that is really 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 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 writing over New Years and I was looking at the life cycles of companies and they they often start like Cults and I went through I think IBM Instagram all of these huge companies and I found quotes of the founders describing the early days like a cult and then they go into this kind of growth phase where because everything is 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 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 kind of like this Enterprise phase where the processes are in place work-life balance has kind of been restored they have a lot of people so now they have like a HR department and things are different now 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 where he was like you know um see what's the

effect of the start should resemble a cult do you believe that it's something I've pondered because the word go is such a toxic word so be careful yeah I mean I I I yeah I don't know I'm not sure if cult's word I 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 great company you have to have a strong mission and part of the reason that I think Shopify for me at least is the place where I can

do my best work is because the mission is not interesting or cool or it really hits home for me 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 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 they're selling sugar water and they're selling candy and they're selling chips and whatever they whatever Pepsi sells 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 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 Cola we are you know we are nourishing the Youth of the world to pursue their you're selling something that like I like but I don't really love and I think if you're if you have the ability to find a company whose mission you believe in in every in any stage really hits you hard that's probably the company you should

go work at and you've probably seen that for a very long time and even the fact that not every not every person needs to say to every company forever not everyone's gonna be a lifer that's okay people want 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 your own life's Mission if I wasn't at Shopify if Shopify didn't exist I probably would be doing something around encouraging more entrepreneurship inspiring more entrepreneurs creating tools that

help entrepreneurs start scale and build faster I just found this this vehicle that does 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 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 company actually doing if you strip away all the marketing speak and all the brands speak what is the point of the company what's the objective

and I think that's that really matters for those entrepreneurs then that Shopify supports when we talked about this Mount Everest analogy where you're you're thinking about starting a 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 into a into a small business you gave the example that many of shopify's merchants don't even register the company by the time they start the store the other part that's um intimidating when I'm thinking about starting a business if I'm a startup entrepreneur it's

just information and you used a word earlier on use the word mentorship now okay I've got a philosophy to how I'm going to start it I'm going to focus on a hobby Harley 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 most important piece because information for example is even the knowledge that a Shopify exists it's also like how do I find where I'm gonna get this tea from how would you recommend an entrepreneur solve the information problem and if you could give

me some kind of reference to your framework on on mentorship that'd be super helpful yeah 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 should wholesale take everything they say um Lindsay and I got married in 2013 and I thought about who are all the people that I perceived to have a really great relationship with our spouses and I went through the list and I kind of laughed I was like okay like 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 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 really good husband a really good father a really good leader of Shopify I want to be a really good human being from a charity or philanthropy perspective instead of trying to find one size fits all like one person does all those things where it all

comes together it would be so much better for me actually to just focus on verticals so in the vertical of parenting who's someone that I think does a really good job in parenting 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 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 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 he'll be a divorcement maybe yeah but he's really good about understanding skill set or skill stacking as we talked about there was someone that I called when I was about to get married to Lindsay who I just felt had the most special relationship with his wife and I began meeting him and asking questions about how do you cultivate that the same thing with parenting but all of these mentors in each of these verticals they're not the same people now the

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 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 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 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 that successful or or in other aspects of Life he's not someone who had wanna Who had who I admire 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 as you evolve you may have to replace them and bring them in bring them out some people may be around for a long time other people after two years I mean I had a really good Mentor around parenting who was really only

valuable 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 stuff that I want to teach my kids like skiing for example so that's part of my philosophy on on 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 tribe side of things and the one thing that I don't think enough people take advantage of

is whatever company you're trying to build in whatever vertical or geography or or you know whatever place there are probably dozens of other people doing that exact same thing whether you're in London or you're in like Ottawa Canada 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 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 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 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 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 video about bookkeeping for DJ companies there's probably a video on YouTube Somewhere go look at the comments who's 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 people either online or or in person and you can build yourself and informal board of directors when you're getting started now if one of you eclipses the other in terms of growth you're probably not going to find as much value from 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 the acquisition of information gets much easier over time and I don't

think enough people take advantage of that if I if I gave you um if I give you three million dollars and I said Harley you've got to invest one million dollars in three companies more specifically three founders that are currently Shopify customers who would you invest it in and why would you choose those entrepreneurs and founders it's like asking me like you know choose your babies yeah choose your favorite child yeah really I'm trying to get the characteristics of the founders that you back you know I I know right now it's almost uh if you

saw a word clouded 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 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 someone that has a super successful podcast for example or a super successful blog or super successful you know YouTube channel and they want to they want to expand their monetization so they do something like they make t-shirts with you know

the dire with Co on it the greatest content creators now that I see really building their brands are doing something totally different and I know this is an obvious example but what Kylie Jenner did with Kylie Cosmetics is nothing short of brilliant now it's not to say that that you know she came with a built-in audience she was on this crazy TV show for her whole childhood she was someone who if you followed her on social media eight years ago eight years ago you would have seen she really cares about makeup she was in makeup

tutorials and she was doing makeup 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 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 really well and she went and she created what she believed was a better version of makeup called Kylie cosmetics and then she brought it to the world what Jimmy did with like Beast burgers or with feastables Mr 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 company and say I want to create a Mr Beast chocolate bar he went he loves 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 cultivated it he said this is [ __ ] delicious and now he's going to actually distribute it he's going to actually scale it those are I would definitely put one of those millions

of dollars into the hands of a Creator who's on the precipice of figuring out what exactly does my audience like and then creating a better version of that because I think that most of the content creators out there do create promotional products where they put their sticker on something that already exists but the good ones the great ones they actually improve on what already exists in the 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 would be someone

who does something very nichy um you and I are both in black t-shirts in my opinion there's someone who thinks about black t-shirts more than anybody else on the planet his name is James James purse James purse is obsessed with black t-shirts and so I love wearing 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 into James and I would say go do more of this because I actually now I'm not sure 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 one particular thing and building the best version of it on the planet I don't think most people do it I think most people start with something like a t-shirt and they go very very Broad and James hasn't I mean he has he makes other clothing but he has a ping pong table I'm not joking that he makes which is the most beautiful ping pong table he's ever I've ever seen he he has a couple of these sort of villa

rentals in Mexico um which he designed himself but he's he it's one particular vertical that I think is really really cool maybe the third thing that I would uh that I'd invest in so content creator be first someone like James purse who does one vertical really well be the second the third one would be someone who is trying to bring something that was unattainable for the masses into their hands so this microphone that we're using right now is a sure sm7b and from everything I've read because I like this type of stuff it is like

one of the greatest pieces of engineering audio engineering ever created which is why sure who makes the microphone hasn't really changed it much this is a great microphone it's expensive someone who is taking a microphone like this this type of quality and creating a less expensive version of this so more people can try their head at podcasting that would be really cool too interesting making light quality more 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 camera

that we're using now versus a webcam of course and in terms of the characteristics of the human what what do you bet on I mean we talked about this a lot so it's going to sound repetitive but it's resiliency I'm looking for those surfboard people the people that see 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 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 those are often the same people but I want someone who um 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 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 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 care where they're based I don't really care what their experience is um I care about are they the surfboard people because I think surfboard people are deeply curious and deeply ambitious we spoke to your team and asked them what you in particular were good at um oh God they um they did not tell me you did that did 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 up the phone and

so we couldn't so we'll move on um I Heard the gas but backstage here yeah I probably couldn't hear that on the mic so everyone everyone that like Works closely on my team uh are all also all entrepreneurs himself they all have side hustles oh really cool yeah no they said lots of many many amazing things about 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 explain this is one of your team members said he's very very good at

the telescope process of effective prioritization what What on earth does that mean a calendar everything well they made it sound much better maybe they should be the storytelligence I I truly like before I came here I want to grab a quick coffee um that was in the calendar my my meditation this morning is in the calendar the things that I really really care about I diarize and I stick to that diarization and because of that I think it's easier for me to prioritize what's important in my life both professionally and personally than most people who

they try to fit things in um I often don't walk into a place you know you ever meet those people that are 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 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 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 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 my calendar you will see walk with Lindsay like walk with my wife you will see like ski time with Bailey or Zoe 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 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 I'm not sure I'm like the world's greatest prioritizer but because that I'm able to prioritize things in a way that that I think most people may not always be able to do so that that's one thing in 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 the nice to have thing these are things that are in my life are must-haves and um Shopify is very important to me Lindsay and the girls are very important to me um

like some of the charity projects we're doing particularly some some of the um uh some of the Jewish charity projects we're doing right now in Canada are very important to me there's not much else I'm not trying to also qualify for a marathon I'm not also trying to um you know do research on some other topic like this is kind of the stuff that matters and so when when our when we first you and I first connected I knew that I would one day would love to be on your show why because like when 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 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 world going to find Value in what can I get paid for and and um and what what adds the most amount of value I think generally I forgot the exact terms this conversation with you hits a bunch of those like the intersections

of Venn diagram this hits you're a great entrepreneur your audience are great entrepreneurs I knew the conversation would be interesting because I listened to this podcast and I love your show um it was obvious to say yes if someone else asked me to to to do a conversation for a couple 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 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

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on during your time at Shopify what has been your most difficult personal challenge like what was the day or the period where you had your hardest time I think it was um on a personal level it was probably the pandemic I felt very very lonely um I I just I was low on energy I was high in anxiety and I wasn't making time it was like the pandemic was crazy for Shopify overnight every physical retailer shut down and we were really lucky in that a lot 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 we were fully you know fully remote at that point and I I was not in a good place 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 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 of great I talked about my

calendar efficiency I had this great sort of plan usually and then the pandemic hit and like everything changed and scheduling all this time I didn't replace the time with mentors that I meet in person with with virtual coffees I just canceled it and so I just it was a very 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 a ton of people and I was lonely I was really [ __ ] lonely that was a low point on a

professional 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 being president um I felt like I was letting down the 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 count like all these different teams reported up to me um from a headcount perspective there were like six thousand people that 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 self-confidence nor do I nor did I have the um enough introspection to say I'm in the wrong job and I was fortunate that other people 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 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 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 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 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 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 but I never kind of settled in to say where do I actually want to do like like what is my craft here I always love storytelling but I was never I think I was too caught up with ego and insecurity to admit this is the [ __ ] I want to do I don't want this rest of my life I want to get so good at this and it was really with help with coaching and and the 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 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 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 become a well-rounded Riverstone in those dark moments and those hard times did you did you speak to anybody as in 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 happy did you have a conversation um no I don't think I was able I don't 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 maybe this is it maybe I've hit I've hit the my Max here right I mean I've been 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 appreciate is that the thing that I really want to do is also the thing that everyone else really 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 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 enough I am the happiest I'm not just saying that uh because Ron camera at this 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 I'm doing the thing I should be doing which is this particular skill this particular role that I have is kind of built perfectly for me and I need to be okay with the fact that I 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 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 also to my own developments and I think that's if you can find that if you have people around you your partners your colleagues your your board whatever it is that 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 be the chef at Shopify it's not really going to add much value but if it turns out and and that that the van diagram will wrap of what am I

really good at what does a company value for me and what is something that is uniquely in my skill set if wherever that Venn diagram overlaps if you can do that you win what about in the pandemic when you're struggling did you did you have a actual conversation this I'm asking this question because I'm so compelled by like when specifically with some men who are 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 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 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 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 more difficult on myself because I I was lonely

and unhappy and maybe had some sort of you know maybe there was I talked about anxiety but maybe there's a bit depression there as well however I didn't talk to anyone about it because I didn't feel like I had the right to complain I didn't feel like I had enough yeah that I had enough permission to 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 that like I'm a bit lonely and in hindsight I should have done it differently

I should have said look I recognize that I'm very fortunate very blessed but I also recognize that I'm also really lonely right now and I think what that would have by by telling people that by saying it out loud you know there's that whole theory about don't tell people your goals I think it's ridiculous don't tell me your goals I think you tell everybody your goals because the cool part is if you have people around you that are good 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 and celebrate someone you know who deeply wanted to do something who actually ends up doing that thing 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 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 you tell someone your goal you as an individual you get something from that the critique

of it is you don't deserve anything by just saying something out loud that I think it's complete [ __ ] 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 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 something really challenging difficult especially in social media where people love to rip into each other that may hold you accountable

so I did not do the right thing at that particular time I hesitated and it's because of some weird 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 anxious and I actually think my biggest lesson from all of that is vulnerability for the right people to your point good friends good family good colleagues good partners it shows strength it does not show weakness and I was very weak and I didn't want to 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 masculinity sometimes in our sense of wanting to be what we think strong is the sort of misrepresentation of strength we see being vulnerable as a repellent as in I will lose things people will will leave me they'll think 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 sometimes it's a magnet everything almost always it's like the antidote for loneliness in many

respects and there's another really important thing to say because you um in that basement during the pandemic your family were there in the house and we often confuse this idea of being alone with loneliness totally and Simon cynics actually I've given 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 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 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 Trap again he wasn't alone so I was not alone but I was lonely and actually this is where going back to your your point earlier which is a great point about entrepreneurship being a lonely activity or a lonely sport by having more people around you on the journey with you even if they're on their own Journeys but they're sort of tangential to your journey it's a

little bit less lonely yeah and if you do that across a couple different areas of your life like if you work out at a gym or you go for runs in the morning finding someone else to run with you is one thing but finding someone else to 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 stuff for them too there's an immediate connection there so in one case

you may be not like you're 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 experience or you're sharing an experience that takes away from the loneliness how does that square with shopify's approach to remote working 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 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

um this total remote work scenario is because I think there's been a decay in Institute Community institutions in our world so in the UK like all the pubs are shutting down we don't have community centers churches Etc work seems to be 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 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 on but when I'm like an

18 19 year old just left University when I'm 21 years old and I've just left University I want to be do I not want to be around people um to build connections to build skills for synchronous work 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 um as I used to Once Upon a Time how do you square all of that together 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 something like that offices around the world and we were full-time in the office pre-pandemic and now we sort of have this model which we refer to as digital by Design which means that office centricity is over and the reason that's important for us is that we've been building this company out of Canada you know for almost two 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 condition you have to move to Canada and so

that immediately limited the type of talent of the people that come to Shopify and so there's a real advantage to the fact that now you can work anywhere you want so that's that's 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 DC um our chief operating officers is is down south that is great people can live wherever they want however we didn't close the offices we converted them from quote-un offices to more of these we call burst 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 people coming in we've forced people to spend time with their teams in person at least once a quarter and what you see is the healthiest teams um may not have to meet as regularly 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 forming it is really important for them to be in person we really encourage that so we're not

really hybrid because it's 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 together with your team in person at least once a quarter in some cases once every month every solution every ounce has a downside for sure office centricity has a downside of clear one what's the downside in your view of that 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 being in person

you're probably gonna be in person more often and if your manager does not you may be less 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 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 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

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 work for us we need to be in person sometimes we also realize that it's really an amazing opportunity for 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 anywhere they want that is an amazing art like you know in the early days of shop I moved to Ottawa Canada for Shopify and that's

that's a that's a big thing for my family so the 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 just back to the Simon cynic uh quote uh or or philosophy I think we all need like we may not go to church as much anymore or youth groups or you know organized Sports I think we all need our own version of that tribe and I think developing your own community in your

own tribe even if you guys sit around and stare at screens you're playing video games together I think having these rituals 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 we say sort of the the very basic Jewish prayers but this ritual that my kids look forward to where they you know they say shabbat shalom and my wife you know makes this amazing like home-cooked dinner 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 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 create new ones all the time the key though is consistency and and the direction of travel at a very macro level with all these things that are happening in technology seems to be um one in which where we're being stripped of community and in-person connection which seems to humans aren't changing technology is but our innate fundamental maslovian or like

psychological needs aren't changing but the society we live in I think is optimizing against our um against Natural connection living in you know four white walls in the middle of a big city alone swiping on Tinder 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 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 we without really being that intentional about it to be honest have created a sense of connection for people they will hear your story about your own insecurities or about the things you struggled with and that'll make them 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 shared experience even if I don't know you yeah is really impactful we may not know each other we may have never met before people that are watching but if you if anything that

I said anything in my story resembles your own or resonates with you um hopefully all I can what you take from this is that like there is a way to 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 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 happy all the time no one has a great relationship great career great health great family we're like

really no one has that we're all but the best ones in my view are the ones that are self-aware of where what to work on and they have tactics and tools and traits to sort of move towards a better version of themselves they grab their surfboard when things come on the resiliency side they're very honest about the like when 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 had to sort of

epiphany that holy [ __ ] no one has their [ __ ] together we're all trying to figure it out in our own ways 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 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 I've listened to a lot of your your interviews we're all kind of working on our own [ __ ] yeah everyone is

and the 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 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 you said I didn't want to say that they're called The Diary of a SEO conversation cards and um what we've 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 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 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 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 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 Gary Neville tell me something you've never told anyone before I don't think I'm a great father I want to be a great father but I don't 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 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 uh my kids will be too old they'll be out

of the house and it'll be too late and um and I really want to be a great father so that's kind of it's quite a vulnerable but that's the truth um yeah mission of what great father looks like is maybe not fitting the great father that you are um potentially uh you see what I mean by that yeah I I do um because you're an inspiration so I mean this goes back to am I am I enough of enough of a father am I enough right um but the thing about the the like being a

great father is 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 the house somewhere I suspect I got 12 years to become a great father and I don't know exactly the right path to get there I I know what my weaknesses are but they're a little bit elusive it's it's am I present with them am I mindful to their needs um but that's something that that I I struggle with and I'd like to 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 um my relationship to Lindsay my contribution to the world a charity perspective that fourth bucket is is can 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 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 performance I don't think the stock price is exactly

directly you know I don't think they're I think that's more um correlation versus causation but the other points in my life my contributions to the community I can measure those 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 really challenging maybe like the other things we've spoken about this great father party is a party that nobody's at potentially um I've never met someone that says I am a great father yeah you may be right um now maybe actually the pursuit of that

is in itself what I'm trying to do as is the case with the life right right exactly exactly right um 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 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 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 him what a great father or great parent does and he says one thing Independence are your children able to be truly independent I thought that was really interesting as sort of a metric for gauging whether or not you've raised you you you're a good parent um another one says like you know there's a famous quote which is you're only as happy as your least happy child um I've actually heard the corporate version that which is like your only successful is your least successful division of your company which is also really interesting way

to 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 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 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 bit left field but what's a common misconception people have about you and more importantly how does it make you feel

because I talk so much about entrepreneurship there is I've heard this now from a number of people that um I don't ever talk about the failures that I've had from a business perspective and partially I don't do that because I don't think it's they're they're necessarily that valuable relative to some of the successes we talk about DJing and t-shirts and and Shopify there are literally 20 other companies that I've started that have been total [ __ ] failures and I think the common misconception is that the stuff that I've worked on have all been not

huge success but generally successful because I talk about them so much and I it makes me feel sometimes like I'm not more recently that I'm not being as helpful or honest as I as I should be because I just don't have I don't have the space or the venue to talk about the slipper company the poker chip company the nurse uniform company like those are all real companies that I started when I was in college or undergrad or when I was a teenager that failed miserably and the misconception is that I I think that that

everything that I've worked on has turned out to be good or successful when you look at yourself in the mirror 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 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 involved in very successful Ventures and Pursuits there's this kind of like perception which might not match the 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 sort of the the failure thing um I do a lot of TV and and um and I'll get feedback that you know that was really great I saw you in the show where I saw you do this interview or saw you on on on Squawk Box um and I'm like great yeah thanks you 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

in five hours of work memorizing those data points I think sometimes I like to pretend like it comes easy to me it does not come easy to me I work 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 lot of time into preparing for my conversation with you today a lot of time I've watched all your interviews I literally as I told you like I I didn't finish my run until I listened to the entire Seth Rogen interview um 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 vulnerability of actually sharing this is not easy for me I'm not naturally I can naturally memorize I'm 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 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 myself where is the dissonance it's that sometimes less

less recently but but certainly often time previously in the past years I've made it seem like this is easy for me and it's not easy for me and I was never the smartest kid in any of my classes I never got I probably made it seem like I was you know smarter than I was in the classes when I wanted to do on a class I just outworked everybody else and I think if if you should if anyone out there wants to emulate anything that I've done emulate my work ethic and the journey not the

destination because it's been [ __ ] hard and still [ __ ] hard and I I embrace it and I enjoy it and I I wouldn't trade for anything else in the world but 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 to me Holly thank you so much incredibly enjoyable conversation I've learned so much but I've 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 unique and and um for me really defining ways I wanted to close with just one thing because I think I'm thinking forward at the guest we've got coming up and the guests we've had previously and maybe you're the guest best place to answer this this started as a very business-centric Show Business Centric podcast started as a me as a young entrepreneur building a company et cetera Etc there's a huge part of my audience base that are doing exactly that right now like they're like maybe they've started their Shopify store um maybe

it's day one they know what they want to sell maybe they don't maybe they're not quite there yet but if there were a piece of advice you could lend to someone who wants to go on that journey of Entrepreneurship of all the things we've discussed today what would that closing remark be remember that the cost of failure right now is the lowest it's ever been in the history of the world and because you if you if you can remember that it means that there's absolutely no reason why you shouldn't keep trying and if it doesn't

actually work try something else 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 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 but knowing that you are interested in entrepreneurship and at the same time in 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 any instinct to start a

business in the shower when you're driving when you're on a walk randomly you have this like this would be a cool idea try it when you look across the millions of stores on Shopify who've now sold more than half a trillion dollars on Shopify the vast majority of them did not wake up and say I'm going to be a great entrepreneur they tried something it worked they scaled it they 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

all of them didn't start out with this this vision of building a billion dollar company at some point and I think that 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 a large multinational multi-billion dollar company if that's what you want that did not happen and it certainly did not happen in the time span that's happening right now the companies now there's there are companies on shop like today where they're doing a billion dollars or more in sales that didn't

exist six years ago six years ago was a shower idea and now they're a multi-billion dollar company or if you don't care about building a billion dollar company they've changed their entire vertical their entire the the their world whatever that their whatever the world they're in they've changed it entirely 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 someone who actually has an idea and wants to share that idea with the world and if you're not sure about an

idea what you could sell how you could start think about something you already do there is a store on Shopify that sells the most delicious matzo ball soup is a is a Jewish chicken soup okay um 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 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 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 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 time and your generosity it means the world to me it's been an incredibly important conversation great conversation thank you for inviting me [Music] over the last couple of how long maybe four months I've been changing my diet shall I say many of

you have really been paying attention to this podcast will know why I've sat here with some 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 superfoods these green Foods these vegetables and then a company I love so 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 announced a new product which absolutely spoke to exactly where I was in my life and

that is huel and they announced Daily Greens Daily Greens is a product that contains 91 superfoods nutrients and plant-based ingredients which helps me meet that dietary requirement with the convenience that he will these offers unfortunately it's only currently available in the US but I hope pray that it'll be with you guys in the 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 [Music] oh