Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game

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0:11[Music] [Music] Finkelstein round two maybe let's start off with with that you know how do you think about hustle versus ballads I'm not sure I'm the right person to ask that question to I I think that I'm trying to optimize my entire life for no uh no transition time or low transition time so I either want to be like full-on you know like hustling and building our business at Shopify or I want to be doing things that give me great you know great joy being with my family um you know meeting interesting people having great conversations you know doing the hobbies that I love to do but

1:11I don't want any transition time or I want to have it reduced as much as possible and so I don't necessarily know what the takeaway message there is but I um I remember like when I was in high school the commute from I was living in South Florida that commute from my house to the high school like it was wasn't very far it was probably two or three miles but it took us like 30 or 40 minutes to get there when there was a lot of traffic and I remember thinking that was like the worst part of my day because um I was pretty ambitious in school I

1:40wanted to do well I was also an entrepreneur I had a DJ business in high school but that was the worst part of my day maybe the first week because it was just non-productive time and so I don't think every moment of my day needs to be structured around efficiency or productivity but I don't want to have time where I'm not enjoying or I'm not building and if it's if I'm not doing one of those things like that is bad use of my time and I think I've optimized that as much as possible so I woke up on Monday and for whatever reason I wasn't feeling excited about

2:15work and motivate it so I texted a friend and I was like I have I'm sure like you have like a Founder group chat and I just texted these these Founders and I was like Hey like this is how I'm feeling I don't ever I don't feel like this very often um and I got this really good response that I'd like your opinion on and I tweeted it so one of my Founder's friends says I actually don't think your life will improve much by applying more pressure I think your life will improve most by creating space to think by protecting nurturing your energy by doing the things you take on really

2:52well and by using your capital and consistent manage risk ways that you can basically rinse and repeat you're at the point that if you can use eight to ten hours in a highly leveraged way in a week that creates more return return than 50 hours of hustle strive for those eight to ten hours to be worth five thousand dollars an hour and then do all the things with the rest of your time to keep those hours valuable what do you think about that I think that's great I mean I think you know there's sort of this this Mantra in our in our world in these sort

3:24of Entrepreneurship World which is uh work really really really hard and and then there's this other Mantra which is like work really really really smart and I think by the way I think platitudes are are a silly way to run your life but I I think in particular those two like um it's a false dichotomy it's not either you're working harder working smart I think there are certain times where you just have to do the work um what I'm preparing for earnings call there are I don't know 50 60 metrics that I have to know I just have to do the work I have to memorize those

3:54metrics I have to really understand how we did what the different you know factors that led to those uh the results have been there's no shortcut for that in other times there's a particular goal I want to get I don't know over here Supreme onto Shopify and like that's my goal and in that those cases there's probably a smart way to do it there's also probably a hard way to do it and in that case I find you know the smart way is almost always better so I agree with that and and by the way you waking up on a Monday and you're not feeling great like that

4:27is a very healthy thing nobody work wakes up every single Monday feeling like they have the world uh and and you know by the tail and and that everything is always amazing years ago I remember thinking that um I think it was on a podcast or I was giving a talk and someone said you know uh have you hit your goal of happiness or something like that I was like I was like No And then I don't think happiness is necessarily the goal and the best example I can give you is that you know you may be happy having a great day everything's going your way you stub

5:00your toe and all of a sudden like you know you feel like [ __ ] first for for a few minutes um I think more than for me the more important thing is is meaning am I like do I have a meaningful life am I doing things in my life that are are deeply meaningful to me this podcast this interview with you is deeply meaningful you and I have known each other well before you know you were Greg Eisenberg and and anyone even heard of Shopify um and and but so this is a deeply meaningful you know conversation because you and I knew each other before

5:30anyone else did and watching each other's journey and growth has been I think on both sides of the coin uh there's real Pride for you know it sounds weird because we're in our 30s and like we'd say that but like you know there's a lot of Pride for Mutual Pride for each other's Journeys um that's meaningful to me after this I get back to like my work at Shopify which is deeply meaningful and then I think I told you sort of the pre-show my wife and I are going to spend the weekend just two of us we've had a lot of like we went to Disney World two

5:55weeks ago with the kids it was kind of very kids I don't know there's a lot of kids stuff in our lives right now my wife and I just want to have a weekend just Harley and Lindsay and so we're gonna go away this weekend and just spend some quality time the two of us also very meaningful and I think the more as you look at your calendar and your schedule if there are things in your account on your schedule that you're like that's not meaningful that's not meaningful that's not meaningful then you should make a change but if you wake up on a Monday morning and fundamentally you're

6:20just not feeling yourself like you're not really in that in that zone it doesn't mean you're failing it doesn't mean you should change everything you're just maybe having like a shitty morning and that's okay and I I think um you know one of the things that great um psychologists and great therapists but also great coaches teach you is to name things I am feeling this way what is this oh this is anxiety oh this is depression um so like the naming things really help but also but the reason I think naming things is so is so valuable is that once you name something oh like I'm feeling anxious

6:53now okay what happened in the last two hours that made me feel anxious oh yeah well I had those phone calls and then you begin to sort of pattern match and you're like okay I actually think today is going to be a tough day and I can prepare for a tough day because I've pattern matched it on days like this I usually leave you know I usually leave my desk feeling pretty exhausted and and I think the quicker you begin to be self-aware about those things uh the quicker you're able to identify yeah I'm not feeling great it's Monday morning I'm just not I'm not I'm not the Greg

7:22Eisenberg I want to be um the better off you are and I think that's something that I've only re only recently learned to do I think for a long time I had these blinders on and and you know call them like hustle blinders where it was like like I don't deserve to be anxious I don't deserve to be sad I don't deserve I have to just work and work and work and work because like if I don't everything is going to crumble and that's not the case you can still be highly productive and very very impactful but also have the acknowledgment that like I'm not doing

7:52great at this particular moment there's something about where we grew up and how we grew up that equips us with hustle blinders out of you know out of the womb and I'm curious if you can shed some light around you know how meaningful you know growing up in Montreal being Jewish being Canadian that has you know yeah I'm sure she can just shed some light around what that means to you what have you learned and you know 99.99 of people listening to this you know don't know that you know people from that neighborhood so can you explain a little bit more about that um so first of all there's this very

8:39very famous quote from Alexander Chalmers and it's called the three grand Essentials of happiness uh something you do someone to love and something to hope for or something that you know that that you're excited you're looking forward to and those are sort of what what Alexander Chalmers calls the three grand Essentials of happiness or meaning I guess is where I think there's a fourth one by the way which is um the environment I think you also need to be an environment that inspires you and you and I grew up in an environment that was deeply inspiring to us and for those of you that don't know Montreal is

9:16um the second largest city I think in Canada maybe the third now uh the second or third largest uh it is the only City I think that is fully bilingual uh and I guess Quebec is the only Province or area that is fully bilingual um but more importantly most importantly it is a city of immigrants in the 40s 50s and 60s Montreal was the recipient of hundreds of thousands and millions of immigrants from all over the world from every single background and in the case of my family where we came in 1956 from Hungary Holocaust Survivors uh came after the Holocaust went to Hungary Hungarian Revolution

9:57forced them out of their home again they ended up coming to Canada Canada had a program where they um LED in 40 000 Hungarian refugees in in 1956 my my father and his siblings and my grandparents came to Canada and came to Montreal at that particular time so Montreal has been historically of a city of immigrants full stop but what that has done is it has created a sense of entrepreneurship because of survival uh rather than entrepreneurship because of passion it it created a place in an environment where everybody you knew growing up just about had a small business was an entrepreneur started something um the famous One in Montreal of course

10:44is the shematza company like a clothing business that was there was a big clothing company but it was a city of entrepreneurs and everyone you met generally seemed to be an entrepreneur or a small business owner or in some cases a much larger business owner in fact the heroes of Montreal growing up were people like Sam brothman who created Seagrams again an immigrant that came to Canada from Eastern Europe who created Seagram's or the demere family who again you know came uh came to Quebec I think originally from Sudbury and built this crazy company or the pelidos the Quebec world so two things were just you know you were smacked in

11:24the face with these two these two interesting ideas growing up and one you knew a ton of entrepreneurs and two the heroes of the city they were not fifth or sixth or eighth generation you know Aristocrats they were in Barrens or or tycoons uh the people you look up to were these first or second generation immigrants who happened to build these incredible businesses and then were incredibly generous in helping to build the city and giving back and I think that that instilled the sense of entrepreneurial um DNA but also this identity that if you have an idea for a business and you grow up Montreal there's a very good

12:03likelihood you're going to probably try your hand at that and I don't think that is the case anywhere else uh not not to that extent now I I have I've come to realize because I've said this I've given the story a couple times that there are other cities Chicago La Miami New York like some of the bigger cities have it but there's a grittiness for Montreal that actually I've seen a little bit in New York City and NCAA lived in Chicago um that that seems unique and people that are going to be watching this you're gonna tell me what your city was like that too I I don't doubt that for a

12:33second but in Montreal it was so it was so obvious and so apparent and so I think growing up with that one it gave me the permission to always consider myself an entrepreneur when I moved from Montreal when I was 13 to South Florida um I was like I went to high school I was I went to public high school big high school and I was this short Jewish Canadian kid in school but I was also I I I introduced myself as oh I'm also an entrepreneur I have this DJ company and I'm always you know tinkering on these new business ideas and and for the most

13:06part there wasn't anyone else like that in fact most of my you know classmates in high school thought that was kind of a weird thing that wasn't the case in Montreal and Montreal like a lot of my friends that I grew up with were also like you I mean you had a web website development company I think when you were what 14 15 right so like it just wasn't that uncommon when I went to South Florida it was very uncommon in fact it was it was it was unique and and someone alienated and so that's a long answer short question but I think growing up in a

13:36place like Montreal where we were inspired by the greatest entrepreneurs that we actually knew we were right into them it wasn't like we didn't read them in textbooks we met them at like some some Jewish Delhi uh and we knew their stories our our parents and grandparents told us their stories we were inspired by that and so Montreal entrepreneurship and frankly um that the culture not necessarily the religious aspect of Judaism but the culture of Judaism is a big part of my life in fact so much so that uh I don't know if I said this to you on the last time we were on but Lindsay and

14:10I my wife and I and our and our daughters we were actually moving to Montreal in five months from now full time and part of it was uh after the pandemic Shopify is now digital by Design so we have people all over the world and we began to think about where do we actually want to live live our life and we looked at a number of amazing cities Miami and New York and some other cities like that and ultimately settled on Montreal because we just think it's just very very unique and there's there's nothing like it anywhere in the world and so uh we're moving there so

14:40if you're not from Montreal you're not from Chicago you're not from L.A not from Miami what what are some takeaways for people that they could wake up Monday morning and get into that Montreal mentality okay so I I I've been thinking a lot about this because I live in Ottawa okay I've lived in Ottawa now I moved here in 2005 to go to law school uh that was the year I met Toby became one of the First Merchants on Shopify like that was a you know it was it was important but I came to Ottawa to go to law school because a mentor of mine happened to be teaching

15:10law at the University of Ottawa in 2005 and and he convinced me to go to law school to become a better entrepreneur I think I've told that story on the show before Ottawa is not an entrepreneurial city Ottawa is a government Town one-third of I think it's like 32 to be specific of the residents in this city work for the governance the capital of Canada so inherently there is not an entrepreneurial spirit in this city you don't have the same type of immigrant hustle here you do in Montreal and that was really challenging for me and so what we had to do was because there wasn't organically a tribe around us of

15:46other people like us we had to build our own and that actually led to uh fresh Founders which was the group of of a number of us that got together every Friday and we created a tribe of our own of entrepreneurs in a city that is not inherently entrepreneurial and funny enough that that group that we created ended up building you know get around uh travel pod uh fellow uh fluid surveys Shopify uh it's kind of an amazing interesting group of people um but we had to create our own and so I've thought a lot about if you are not in a city that is especially entrepreneurial if you were

16:23you know you and I were both in Austin two weeks ago right I believe yeah for South by I mean there's this crazy energy in Austin it's unbelievable right and you want to have a lot of mutual friends that have moved there recently like you know every second person you meet is doing like an entrepreneurial podcast and like every second physical retail store is a direct consumer brand I mean like it's unbelievable I walked down I think it was Sixth Street and it was like it was aloe yoga and then James purse and then to covis and then all birds it was like all these amazing

16:51Shopify Brands I was like I felt like I was home most places aren't like that and so if you don't live in a place like that you have to cultivate your own version of that you know smaller subset and you actually have to very intentionally create a community so there's there's two I want to dissect that a little bit so there's two pieces of that so one what you're saying is peers basically having peers that you can that can inspire you essentially um the other piece is mentors and I think you're really interesting person with mentors because you have in my opinion a set of like

17:30yeah I would say obvious mentors like people who like you know Seth Godin someone like that who I'm like yeah like it makes sense that like you you know you would look up to someone like Seth Godin and and he and you guys would get along but then you have a set of non-obvious Tech you know mentors who might be a lot older can you talk more about how you think about mentorship yeah um so I mean like it is it is unbelievable uh to me even to this point that I I have relationships with with these incredible you know like people uh and and some of them are are very well

18:10known you mentioned Seth and uh I'm lucky that I have people like that in my life but there's also um a set of I like your term non-obvious the reason I think that's even more important to talk about is because everyone who is listening has access to non-obvious potential mentors who unequivocally will change their life if all they did was reach out and so part of what I've been trying to do is is just as I've you know as I got married and had kids and and and and our business at Shopify can use to grow is just be on the lookout for people that I

18:43find to be really interesting in one particular aspect so either you know great relationship great parenting uh they have a certain like a joy of Life they have you know um and forget about age forget about their net worth forget about like you know I I I'll say the sentence this isn't just blowing smoke like I really look up to you Greg and what you've done with this show like you have this incredible appetite and desire to share these stories around like the new version of business creation and community building around and using Community to build a great incredible businesses and you're just doing this like you're like [ __ ] it

19:21I'm going to create this incredible where it happens program and I'm gonna do it uh I I I'm gonna do it like all full on so I've just been on the lookout for all these different people and so what I've sort of do more recently is take the next step and say look like I I know this is kind of a weird thing but like I notice how you are you know with your spouse and notice how you are with your son or daughter on the ski hill on Saturday can we can I talk to you about that can I ask you about how you were so

19:53um Mindful and so present with your spouse or like can I ask you about like I noticed you and your wife are always holding hands like that seems so nice and so romantic and my wife and I like the whole hands also but like you guys are always holding hands like what's that about and what you start to realize is that all these people that exist they may be 90 years old or they may be 17 years old they have something to teach you and if you can simply just you know ask them a set of questions that allows you to derive some some value and input from that there

20:26they really like talking about this too these non-obvious mentors by the way they don't have a lot of people asking them for their time in fact I I I've enjoyed this so much that um I recently put together this this project called Big Shot which is me sitting down with these non-obvious for the most case these these older Jewish entrepreneurs in their 70s 80s and 90s and just ask them questions about their life and ended up recording the whole thing because I think that I want to create an archive of these stories but you realize as you meet these people that are again non-obvious mentors how

20:58much they have to teach and how nobody is no one has heard their stories and so non-obvious mentors actually have a non-obvious amount of alpha uh in terms of teaching and insight and impact that you can derive if you simply ask them about it and for me in particular these you know older Jewish entrepreneurs who came to North America with literally nothing and have built multi-billion dollar companies and have have created the largest charities in some cases they bought me they brought Major League Baseball to a new country like Canada uh in the case of of Montreal Expos I want to understand how the hell that happened I want to know

21:37like how that all went down I want to know you know the person that that built you know 20 skyscrapers I want to know how that person first got their their initial round of financing to build their first skyscraper at 24 years old with no experience no one else has been asking those questions no one asks no one else has been going after those people and saying can you tell us your story yeah so love this first of all just absolutely loving this uh thank you I think it's fun yeah this is great so you would love by the way like big shots yeah the first episode

22:10comes out tomorrow uh this is not a plug for big shot but but Greg in particular like you're you're gonna love this because these are people that are like it's like it's it's part documentary and it's part sitting in a Jewish delicatessen like on Second Street in New York and like it's like if the walls can talk at an old school Jewish deli this is what they would say yeah so I'm I'm not going to say where I live but I live in an island where the average age is very high so I spend a lot of my time just sitting in hot tubs with old people

22:43[Laughter] you should turn you should record those conversations from the hot tub yeah and I know that sounds weird but it doesn't sound weird it sounds amazing if they're having instant conversations and you are getting access to those conversations I mean these are people that have had three or four lifetimes compared to us yeah yeah and they have so much to teach um but I mean I I guess to summarize like I'm fascinated by the non-obvious mentors in a way that like I've the obvious mentors that I have I'm grateful for but I've I've read their books and I'm able to choose to hear their stories

23:18and anecdotes across a whole variety of of media podcasts television shows in their books on you know across on social media and and on their blogs but these other people that are equally as interesting um there's a lot of alpha there because they haven't told it and and so back to your earlier Point by the way if you're in a city or in a place where you don't have like it's not Austin Texas and you don't have like you know Tim Ferriss is randomly walking around and and showing up and having a conversation when I was when I was at when I was in South by I

23:50think you know this I interviewed Tim at the Shopify space and Kevin Kelly just walked it like like Kevin Kelly from 1 000 true fans like that he just walked into the shop by space like oh and actually Farhan he works shop like he saw Kevin in line and said I think Kevin Kelly is in line to get into the space like Kevin come in like that doesn't happen in Ottawa right because it doesn't happen in Ottawa Canada where I live I've had to sort of create um versions of that on my own and and it's not easy but it's incredibly rewarding here's I want to double click into the

24:22alpha comment that you made here's why non-obvious mentors provide Alpha is because they're gonna help you create products that go against the grain and when you go against the grain that's where the opportunities lie right they give everyone is saying hey go build a startup like XYZ on Twitter then [Music] the moat you have a smaller moat yeah it's it's you know um after we had our first child after

24:52Bailey was born in 2016. my wife and I would go for these walks every day newborn baby like can't do much uh you know babies like sleeping or eating most of the time so we went for these walks around our neighborhood um here in Ottawa and Lindsay my wife had said hey you know I I would love to go for some great ice cream there's an ice cream shop I'm gonna create an ice cream company I'm gonna create an ice cream retail shop uh called Sunday School and of course like I'm like you know I'm I'm I'm the poster child for entrepreneurship I'm like the physical

25:22manifestation of like the entrepreneurial Spirit uh at least I hope I am or try to be and I was like Glenn's great idea let's do that and she's like great who do I talk to I was like I have no idea I don't know anyone that like I was like maybe we can call Ben and Jerry like I think you know like I I maybe they'll take my call maybe they'll answer my email anyways Lindsay is like leave it to me and she went around she found all these incredible ice cream entrepreneurs and she developed these relationships with them and Sunday at school like was rocking

25:49like like the setup the design the production uh every aspect of Sunday school was like I'm this is like me being very proud of my wife I was [ __ ] perfect it was so well done and the only reason uh but not the only reason but one of the only reason Lindsay was able to get that Insight was because she didn't listen to me she didn't call Ben Jerry she didn't call Haagen-Dazs she didn't call Baskin Robbins she called these like these fairly um unknown or non-obvious ice cream Entre entrepreneurs and she began to network in that community and they gave her all this amazing insight and if

26:22she would have listened to me and she would have called Ben Jerry's because my answer for everything is like who's the biggest ice cream entrepreneur that's who we should talk to she didn't do that she went to these not all these ice cream mentors and she was able to build an incredible business doing it um and they were so happy to hear from her because some of these ice cream entrepreneurs are in their 60s and 70s some of the one of them it was 85 and they were worried that the next generation of of ice cream you know business owners ice cream company business owners wasn't around and so

26:50they were delighted to hear this 35 year old woman from Ottawa Canada really was excited about becoming an ice cream entrepreneur and they gave her um a disproportionate amount of their time relative to what she would have got if she would have called someone that I was going to recommend I think a big takeaway for for people listening to this is you want to surround yourself non-obvious like it's good to have these not obvious for example ice cream entrepreneurs but it's also good to have the Harleys or the Ben and Jerry's also and and thinking about maybe you start not obvious but over time you can scale with

27:27like oh yeah you know now I can call Ben and Jerry's and scale this thing yeah exactly at some point if Lindsay was looking to raise money or you know uh for the ice cream company I think that Ben Jerry's could be helpful um uh I think Ben and Jerry's actually his own Now by by a large cpg I I suspect a big conglomerate but that's exactly right or if she needed to figure out like something really you know complicated like uh dairy uh tariffs in Canada versus the US there's probably a lawyer she would have to call there but but that's exactly right and the cool part

27:59about this non-obvious mentorship and and and and that leading to finding Alpha is that everybody can do it there is someone in your town if you were listening who makes like I don't know um like the caps for water bottles like that person may have a huge company that no one's ever heard of and the stories you will get number one will be so fascinating but more importantly they may teach you way more of a business than you're going to find in any business book yep absolutely I need it I need to share two small but big wins that I've had in the last three weeks with you

28:32that I haven't shared with anywhere wow well with everyone but just something that's related to this so they say don't meet your Heroes but I'm like I made a goal for myself that this month I was going to meet my heroes wow so I dm'd Rivers Cuomo who's the front man of Weezer yeah amazing and to me he's like a non-obvious role model even though he's big like he's not obvious in the sense like you know he's not Tim Ferriss or Seth Godin so I DM to you know if you're watching this on YouTube you know I dm'd him this um I basically said I bet you hear this

29:15a ton your art has been life-changing to me often in La would be cool to hang out sometime and he responded instantly wow and he was like let's do it I'll be here until June what part of the world you're in so I tell I tell him I'm in Miami he's like oh I'm gonna be in Tampa even though that's not even near Miami but I'm going to be in Tampa in a couple weeks come let's come hang out I so I go to Tampa and I have you went to Tampa to meet him I went to Tampa to meet him cool car breaks down Midway through of course you

29:53know just just in the Everglades which for people to know before that's like there's alligators all over yeah it's not a great place to have the car break down that's right no yeah no exactly but I'm doing this right because I'm thinking to myself how could I make 16 year old Greg really proud right now I'm going to the show so go to the show I meet with him backstage and I have this 20 long Co 20 minute 30 minute whatever it was conversation with him around um like rock and roll and music and programming and all these different topics and I left that show just getting

30:33completely inspired and my my biggest takeaway was DM like you'd be surprised who would respond to your DMs quick Interruption from me if you're listening to this on Apple podcast or Spotify you're getting any value you need to come to YouTube and subscribe to the where it happens podcast YouTube channel I promise you the experience is richer more interesting so if you're getting any value just stop what you're doing open up the YouTube app go to the website and press subscribe at where it happens on YouTube and if you're watching this on YouTube and you haven't subscribed what are you doing go go press subscribe thank you enjoy the rest of the show

31:23and by the way that like if if he wouldn't have responded the cost of failure is literally 30 seconds of your time correct that's all it is and I by the way I love I love that I especially love it because what you also realize is that um he probably you know you didn't tell us this point of uh perspective but what he probably learned from you about the future of music and the future distribution and the Weezer community and like what that Weezer you know Africa album did like like I rediscovered Toto through Weezer that's right like it's an unbelievable thing that like like you probably dropped all

31:59this great knowledge inside on him and and he probably feels like he got as much out of that meeting as you did and and everyone listening can do that exact same thing right now um and and again as long as you don't have a fear of failure or a fear of rejection which by the way you should not have like there who cares you may actually build the most like you may have a relationship now uh Greg with him for the rest of your life well that was the cool thing at the end he was like oh I have to you know get back or I'm going

32:28to Orlando right now but like here you know you gotta we gotta hang out soon we're hanging out soon and now he's like I could say like Rivers is my homie you know it's amazing that's amazing I I did something recently uh during the pandemic um I sort of saw or heard that uh Tom Green is moving back uh from from LA to Ottawa his parents live here and I randomly sent him a note and said hey Tom a huge fan I grew up watching MTV and watching the Tom Green Show and I think you're super cool and we we hung up we've hung out a bunch of

33:00times in fact I think I introduced Tom to you yeah as well um and now like Tom is like introduced to me to his friends I've been shooting Tom to my friends like that all happened because of a single Instagram DM and he had not heard about Shopify he didn't know who I was he was like oh this kid from Ottawa where I'm moving to just reached out I'd like to meet new people especially people that seem like they're in Tech and doing interesting things like that is unbelievable and by the way that was impossible 10 years ago so what advice do you have to people who who

33:32you know have a Target list of of people who could be role models and mentors and like like what do they need to type in the DM for for someone like you to open it up and read it and reply I I I find for some um the DM is really really challenging sometimes because they have a lot of things coming in and a lot of people coming in a lot of people messaging them one one other way that's super simple is almost everyone you want to meet has some sort of um not everyone but most people have some sort of philanthropic charity and Foundation they're connected to that

34:08means a lot to them and if you do research on them it is very obvious what that is and if you make a donation it can be literally 18 okay because I've tried this 18 uh to a charity or a foundation that they care about and you put in the memo like I am donating this because I was inspired by this particular thing this particular person did and I'm doing it in in their honor um and then you DM them now it's like now you have two different touch points now all of a sudden like I keep seeing this guy's name like like the [ __ ] is

34:41Harley Finkelstein he gave 18 to this charity I really care about he sent me a DM he also bought something from my merch store he bought like three t-shirts and left a really nice comment a nice review you can create something that is number one very lightweight very inexpensive that can give you a ridiculous amount of reach to the people that you want and then once you have those relationships like that's when the work really starts because it's one thing to get a first Connection in Tampa with you uh you know to have a meeting that's great but the fact that he is now your homie

35:13um means that it means that you have also contributed like you were sending him text messages you were you were reminded of something that was discussed in the conversation and you're like hey this is a cool article you should read this I know you were thinking about this hey by the way I saw this other thing check this out and that is really how you build real relationships now I just want to say this the thing some people will say well isn't that superficial you're sort of like you're using uh tactics to build a relationship no every single friendship every single relationship is built on some sort of

35:41shared experience some sort of shared centerpiece of Interest or connection and so if you marinate that and and and like it is not transactional because ultimately the only thing I want from these people is to get to know them better because I think the more I get to know them the more interesting uh the more interesting they become to me the more I can learn the more I can share with them like that is how you build real Community you don't build real Community by having a one-time let me pick your brain here's 10 questions and then never call them again you know those people are never going to

36:14be quite about your homies um they'll be your homies if you actually are able to create a real dynamic between like what they need what you which you need what you want and and it doesn't have to feel transactional or superficial because some of my you know some of my closest friends today are people that started out as mentors to me and now like they're huge parts of my life and I'm a huge part of their life and I feel very lucky to have that and and but it's it there's it's real like it's authentic even though it may have started from what seems like a business

36:45pitch so Step One is do your research like do do your proper research do your Danny Miranda style research shout out to Daddy Miranda man he does his research the steady Miranda found out where I went to high school uh and drove by the high school before he interviewed me because his grandparents lived nearby like holy [ __ ] that's like next level research that's why I was like I'm not even gonna do research for this just listen I didn't write this podcast exactly so I did that um do your research so no know what's important to them through that step two is I mean you want to craft a short and

37:24sweet message too right like you can't you don't don't have like a null but don't send a novel yeah either not novel is bad and hey can I pick your brain is bad yeah don't write High context like you're right like like high context thoughtful don't waste their time and there's a connection I mean for like the people that reach out to me now like they're like my life is so public right everything I'm interested in whether it's like Shopify or it's fire bellied tea or it's big shot or it's my wife and family like I'm so public like there were so many intersections of me with

37:57pretty much most people that like you can figure it out and and I do the same thing um in fact it's more challenging because I like to figure out you know one of the people that I interviewed recently was this guy named Aldo Ben sedude do you know how old I've been so dude I do yeah uh so this guy's amazing like the guy like he's an immigrant from Morocco comes to Montreal with no money he was given a small little section of a retail store uh where he was able to sell his own shoe sort of a store within a store and turn that little literally a shelf

38:28into a multi-billion Dollar Empire called Aldo the shoe company any city in America in the world you see all the shoes he built that from one single shelf and so like his his story is not out there so having the the way that I was able to First make contact with him was I remembered that I'd met him at a bar mitzvah that I DJ'd literally 22 years ago um listen that 20 years ago um I remember when I was like 18 or 19 or so I DJ the party he was there and he came up to me and he said yeah you're doing a great job or something like that

39:02and so that's how we started this relationship and then I figured out you know retail and commerce and and what he's thinking about and his connection to the Jewish community and that's how I ended up getting him to come on big shot and sit down with me so like there are ways to contact everybody and and and some of these people like no one's ever other people are not contacting them and so there's an opportunity for you listening right now to contact those types of people if you're if you're smart about it I have a fun Aldo story what is it so when I was 18 and this and this this is

39:34all going to relate when I was 18 I cold email to Aldo probably 70 times no literally literally actually didn't get a response so then I went one layer you know I was like okay who's in this circle and I I reached out to their head of marketing at the time rob oppenheim it was she was like director of Market okay okay yeah I've also done the map of the Aldo ecosystem because I was also trying to you know get to meet him so I know some of these people her name was Jillian okay um and I reached out and she gives me the time of day I'm 18 years old

40:11and I'm like I want to redesign all those website I mean they have how many store they had like 1400 stores at the time yeah um I didn't get their peaked ahead for some 50 stores around the world amazing yeah amazing and I was like you know I I earned her trust let's just say I earned her trust I was you know giving her a lot of yeah I earned her trust and then she said you could have a meeting with Aldo so I finally did it and I show up with my two partners who at the time were in their mid-30s because I needed like someone you know I

40:45I dare I still have like a hybrid I was gonna say like gray hair but they didn't have gray hair they're in their 30s and I'm so excited I'm like butterflies in my stomach prepared this whole presentation for for you know for him and it was this you know it was a picture of like a board room there was like 15 people at this meeting and then when I sat down they said Aldo will only show up for two minutes of the meeting and I was like okay are you serious he walks in Aldo goes I'm here for two minutes what do you got my partners

41:23were offended that they they got two minutes I looked at it like I've got two minutes it's amazing you got two minutes with like one of the most iconic entrepreneurs on the planet one of them walked out one of your partners walked out walked out and I was in this position where I was like what do I do right you got the meeting also right like he was it was into your name on the line not theirs not that not exactly and I was like that's not me that's not me I'm I'm here I'm gonna like I'm going to make these two minutes count and I just said okay screw the

41:59presentation I'm just gonna have a conversation with Aldo and it was an incredible conversation so I mean the lesson there and and the metaphor that I think is so valuable is like I never walk out neither do you I I am never offended I don't never walk out like if I can get a minute of someone's time if I can get five seconds someone's time who I otherwise or who's I don't deserve to have their time I'm gonna value that because who knows where that's going to lead and be the person that doesn't walk out of the meeting be the person that's not offended like you know is it shitty that

42:30you drove 40 minutes or 30 minutes for a two minute meeting maybe who cares like the guy is running 1400 stores he doesn't need a website but he's giving you time because you were able to influence one of his you know one of his someone on his team and and and he's giving you two minutes which has an opportunity cost because you can be doing all these other things like be the person that actually says I'm grateful for the two minutes let me see if I can actually get like take the students into four minutes and what I'm gonna say in the next two minutes hopefully gets you

42:58to sit down and spend a little bit more time with me and if it doesn't I just want to say I'm in like I'm super super grateful for the time and frankly I really look up to and admire what you've built and one day I hope to have half your success and like for someone like Aldo who's not an ego guy who's very kind very thoughtful you know immigrant entrepreneur from Montreal just like you were um he probably was like Hey like I'm gonna give Greg some time because I was in I was like Greg Once Upon a Time too and I I think being the guy that doesn't

43:27get it from the person that doesn't get offended and doesn't get up and walk walk out that's the way to win I'm just sorry I'm I I'm just remembering how I was feeling in that boardroom it was I wish I would have known the story before I sat down with Aldo for big shot because I would have told him this particular story um but it's it's you you're sort of we're also kind of in this conversation we're kind of flirting with another kind of topic which is this idea that our personal lives and our professional lives like really are kind of mixed together now right like we started by

43:56saying no we started we started by talking about non-obvious mentors but partially like mentors quote unquote used to be professional business mentors or professional like if I'm a doctor my mentors are going to be other doctors well and I think what a lot of people that listen to this podcast and the show think about is like like there is no separation between work Greg and and and and like non-work rag it's like it's just us right and we want to fill up our lives our buckets with people that are are Inspire us with people that influence us they may be relationship mentors they may be parent mentors they

44:32may be business mentors they may just be life mentors like you and I probably know a bunch of the same people um there's uh there's someone who who you and I both know actually who actually runs a funeral home in Montreal um and I'll say his first time won't say his last name his name is Ross and I think when when you see Ross who works in a funeral home day in day out there's something about this guy where he's kind of floating on air you ever notice that like he's always happy and there's always a smile at his face and this wonderful demeanor and and like I I

45:01don't I don't know exactly everything about his personal life I know very little about his business it's a funeral home uh every time I see him the joke I make is how's business I hear it's dead and he jokes and I laugh and he laughs kind of a dad joke but what I what I love about this particular person is it seems like he's always floating on air in this certain contentment and if I ever had a chance to see him not at a funeral what I'd ask is like can you like can you talk to me about how you you always seem to be so balanced

45:26because I'm I'm an anxious guy I'm you know there's a lot of pressure on me and and obviously you're in a situation which is very stressful you see people when us when uh when a loved one is passed away a but you always seem to be so calm and so collected and so you know content um like is that is that business Harley is that the president of Shopify or is that like Harley the human I'm not really sure but it doesn't really matter I think we're all just trying to construct our own version of of a personal board of directors um and I think you can do that now

45:55better than anyone including you know you know having um the founder of Weezer like you know as one of those people in your life which holy [ __ ] that is so cool I want to double click on the Ross bit just because I find that interesting what is it about what is it about a guy like that that keeps him so balanced like he it's such a hard job to do what he does and maybe the hardest maybe the hardest yeah it's like um I asked in the interview at softball that I do with Tim um I asked him I said you know out of

46:28all the uh out of all the advice you've ever been given uh through all your interviews he's done so or 700 interviews on the Tim Ferriss podcast you know tools of Titans uh tribe of mentors like what's the one thing that like one interview that really sticks out and he talked about this guy who um uh had lost I think he lost three limbs he was paraplegic and he worked in a hospice and the the advice that he basically gave Tim is is given everything I know uh don't believe everything you think that sometimes your mind plays tricks on you anyways that's a that's an aside but

47:05I remember thinking that like this guy and I I didn't really understand what a hospice was I know what it is but so after I spoke to Tim I actually looked up but hospitals like hospice is where people go fundaments ago to die you don't go to a hospice when you're going to recover it is basically saying you are going to pass on at some point soon in in the short in the short run um so this is where you're going to basically live out your days and hearing that this guy works there day in and day out and is is doing interviews with Tim and and and and on

47:38the podcast circuit talking about you know stories and insight and and sharing positive wisdom I was kind of Blown Away by that it's kind of like what what someone like Ross does he's in a funeral home this is where he works day in and day out and yet he is somehow has the ability to when you when you when you show up there he's out there smiling and laughing because it's a somber day you know but but when I saw him recently um after my grandmother died a few weeks ago he just he gave me a big hug it's like how are you doing I was like not

48:09great he's like I get it he's like let me know if you need anything but he had this this certain um devive um that allowed him to be there for people when things were really really challenging and I don't know what it is I'd love to learn more although one thing that I do know is that if you when I have gone into his office at the funeral home do you know this is awesome I made it I was waiting for you to say that let's go so his office is covered with toys There we go toys there there are these toys absolutely everywhere and so he's

48:39figured out a way to despite working in a place where people are constantly you know upset and down they just lost somebody that he's able to recharge his battery because when he goes into his you know his office um is is his Temple at the funeral home for a split second or for a moment he's he looks at these Batman figurines he looks at these you know funny toys and and that's how he's able to refill his own battery so we can be there for people that just lost someone I think that's incredibly thoughtful but more importantly that shows incredible self-awareness that that is what he

49:15requires in order to recharge and um one of the things I've been noticing is is is on days where I've had a really tough day where you know I've had a bunch of meetings and I didn't get the result that I wanted from you know three out of those four meetings I go home and I'm just not I'm not in I'm not my normal self I'm not vibing uh there's something off about me and so now when I feel that way I'll be like well of course that's how I feel I had three meetings and didn't go the way that I wanted uh the next day I have three or

49:43four meetings and they all go the way that I want it I'm home and I've got Swagger and like I'm high-fiving everybody and and and and and once again I remind myself that okay like it's the reason I'm feeling this way is because I had the three or four meetings what I'd like to get to and I'm not there yet is regardless of how my last meeting went how can I be a little bit more even Keel how can be a little more balanced because it is not fair to Lindsay and and Bailey and Zoe my daughter is my wife it's not fair to them that someone

50:11else um that I'm talking to in a professional context is affecting how their dad and Lindsay's husband is showing up at home and I'm not there yet but I think Ross would be the person to learn from in that respect couldn't agree more so happy you share that story and going back to the the feedback that my friend gave me and that founder group chat where he said do all the things with the rest of your time to keep those hours valuable I think he was referring to a little bit of recharging your batteries and have those you know temples to yourself whatever it is toys

50:49Sports whatever it is and go do that so that you can show up um with a game face yeah by the way like the the reason that like this little the space that I'm in right now is sort of it looks like this is is kind of you know I just kind of realized that as I was talking about Ross it's kind of it's the influence of Ross like those are like prototypes for Shopify Awards uh that's a supreme you know uh skateboard to remind Supreme was one of the stores and I always wanted on Shopify like for for decades for us like as long as I've

51:18been in Shopify I wanted Supreme on and and they came on uh on January in January to Shopify and it's a reminder of like how hard I had to work to get that um that's Savio from aloe yoga like uh during Christmas aloe yoga was exploding it was doing amazingly well and I really wanted to like they were worried about whether or not shop was going to keep up and and so I really went deep in helping aloe yoga and and supporting Savio uh who runs technology and digital there and he wrote this amazing see it but this beautiful holiday card thanking me for for um uh for the partnership so all the

51:50things I have here are these little reminders when I walk in after you know I grab a coffee or grab some water or I'm going in between meetings it's a reminder that like you know hey that that went really well that took a long time though really well hey like the merchants on Shopify they're actually my partners like I get to spend time with people that I actually really love and and really deeply respect and I think you need to have that it's not just physical stuff it's also the environment it's also you know you've mentioned sports like your ability to do stuff that recharge your batteries and I

52:19I think that's exactly what that your text was all about I mean proving the point right like you learn something here you are president of a 60 billion dollar company and a funeral home owner taught you like you had such a takeaway right and I mean I can write a book about this guy who by the way has no idea like if if anyone who's listening to this knows who we're talking about here we haven't said his last name yet but like we won't but like if you know we're talking you should call him and have him listen this because I don't think he has any idea of

52:52the influence he's had on me but it's true he has and it's kind of amazing and all of you have all of us have these types of people in our lives where they've influenced influenced us without even knowing it um yeah I don't know chefs do that by the way one of the professions that I find I get most from is is watching a really great chef in a really great kitchen not doesn't have to be 11 Madison Park and I'm in the expensive kitchen but watching a great chef or a great maitre d or a great server or waiter waitress in a great restaurant I

53:21find I get a lot of great inspiration watching someone in their environment particularly in a hot kitchen when it's a packed restaurant and I watch them and I'm like watching how they are under pressure and I look at their shoes are they wearing comfortable shoes and I watch their mannerisms and their voice inflection and I watch how they you know their their non-verbal uh you know non-non-verbal cues with their staff are they showing gratitude are they giving fist bumps what is there was are they smiling are they upset I find that's one of the places where um uh I I gain a lot of inspiration when I go but I love to dine

53:54and so that that's quite helpful I think this is where we end it where it's this needs to end only because I think that people uh it's not at all what we thought we would talk about I think I thought we'd talk more about like you know Lauren Bostick and skinny confidential and uh South by Southwest and the Creator economy but this is uh actually way more fun than that so I hope I hope people got something out of this because this was like you know like this is totally Ren it's like a random show but I I think it was really fun this is this is like uh Tim Ferriss and

54:27Kevin Rose have the random show yeah well actually so uh so I know a lot about that particular show because I know Kevin uh pretty well but I know Tim very very well and I know a lot about that and partially the reason that that goes the way it does and it's so interesting it's a phenomenal you know piece of content they put out is because they have such deep context with each other they knew each other well before either of them had dig or was Tim Ferriss and you and I kind of have that also and in many ways that's like that's the reason why these things flow is

54:55because we have this incredible shared context and if we can shape this context into actual like actionable lessons for people that are listening I think that's really cool while I was uh Brewing my fire belly tea right before this my girlfriend was like oh who are you interviewing and they said you and then she said oh like are you prepared like and I was like to be honest I have a whole list of questions but with Harley I'm just gonna like off the cup and just see what's on his mind and just have a conversation with him that's great I I I love it um and and

55:31thank you for supporting fire belly t uh I too have my fire belly to here uh which I love I mean I'm not supporting fire belly t firebelly's t is supporting me well that's good okay yeah in the sense of like I I believe you were one of the first customers when we when we when we set up fire belly T it's funny what five reality has done for me is like I didn't realize how many people out there actually had never had really great high-end T before and I get so many of those saying like I was a coffee person like when you when when I hear

55:59about tea I think about a gift basket that it was given to me like at some conference or something um it's sort of cool to kind of see how that how T connects people in a unique way I uh I've always been into tea and I used to go to this Chinese tea shop when I was a teenager or traditional tea ceremonies and I love that NDG oh that's very cool in Toronto I I lived in Toronto for a year as a young lawyer um in 2008 and they had something called cold tea do you know what that is yeah so after after the bar scene after the bar is

56:34closed uh you would go to these amazing Chinese restaurants you'd ask for cold tea and they couldn't serve liquor out because it was after serving time was over but they'd put it into these uh teapots they'd serve you beer and you'd have cold tea I mean this wouldn't be a random show with gray guys and we're gonna hardly think Osteen without that exactly a little tidbit if you're ever in Toronto and you're at a bar and it closes and you want to continue your evening go to a great Chinese restaurant and ask for cold tea um and tell them Harley and Greg sent you so I really want people to listen to your

57:06new show where I think people go to do that yeah uh it is uh it is a very personal project I've been working on it on on weekends uh mostly for the last year or so but it comes out this week it's called it's big shot dot show um you can just go there it's on Spotify and and and apple podcast um but it's a deeply personal project where I get to sit down and have these amazing conversations with what I some some of the greatest entrepreneurs that I know they're mostly Jewish entrepreneurs whose stories have never been told um and we just basically record the

57:39conversations and it's part documentary and part as I said kibbetsing in a Jewish deli uh but you can find it at bigshot.show I think if people listen to this and are bought into the idea of non-obvious being a huge unlock which I hope people are that's where you need to yeah it's basically it's an entire it's it's an archive of non-obvious stories but every one of the stories has shaped the world that we live in whether you know it or not and um it's fascinating and also I mean in some cases these are people in their 90s who whose stories you know change the world and and just have not they're

58:16not on the podcast circuit they're not they're on social media all right well so thanks very much thanks for joining of course Greg appreciate it take care