April 13, 2023

Making the Most Out of Life and Business with the President of Shopify

Making the Most Out of Life and Business with the President of Shopify

Today Greg is joined by Harley Finkelstein, the President of Shopify. In this episode, Greg and Harley talk about growing up in a predominantly immigrant neighborhood in Canada, getting mentors and finding joie de vivre.

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Production Team:
Harley Finkelstein:

0:00 - Intro
5:49 - Growing up in Montreal as a Jewish Canadian
10:56 - Finding peers that inspire you
18:29 - The benefits of non-obvious mentors
26:06 - How to DM your heroes


Greg: -Welcome to the show, Harley Finklestein, round two.

Harley: Round two. What I think the last time we, we spoke, it was sort of like middle of Covid.

Greg: Middle Covid. Life was different.

Harley: You were living, I think, in the mountains at that point in the

Greg: I was living in the mountains. I was a mountain man. I was growing my beard. Now I'm

Harley: Now you're in Miami and like much

Greg: yeah, mostly in Miami and, and sometimes in the mountains when I want that peace. And,

so I woke up on Monday and for whatever reason I wasn't feeling excited about work and motivated. 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. This is how I'm feeling. I don't feel like this very often.

Um, and I got this really good response that I'd like your opinion on, . 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 well, and by using your capital in consistent manage risk.

You can basically rinse and repeat. You're at the point that if you can use eight to 10 hours in a highly leveraged way in a week, that creates more Return than 50 hours of hustle. Strive for those eight to 10 hours to be worth $5,000 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?

Harley: you know, there's sort of this, this mantra in our, in our world, in these sort of entrepreneurship, 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, I think, by the way, I think platitudes are, are a silly way to run your life, but I think in in particular, those two, it's a false dichotomy.

It's not either you're working hard or you're working smart. I think there are certain times where you just have to do the work. Um, what I'm preparing for an earnings. 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 metrics. I have to really understand how we did what the different, you know, factors that led to those, 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, a, a hard way to do it. And in the, in that case, I find, you know, the smart way is almost always better.

So I, I agree with that. And, and, and by the way, you wake it up on a Monday, and you not feeling great. Like that is a very healthy thing. Nobody wakes up every single Monday feeling like they have the world. by the tail and, 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, Have you hit your goal of happiness or something like that?

I was like, I was like, no. And, and 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 your toe and all of a sudden, like, you know, you feel like shit for a, for, for a few minutes. Um, for me, the mo more important thing is, is meaning 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, and anyone even heard of Shopify. so this is a deeply meaningful, you know, conversation because you and I knew each other before.

Anyone else did. And watching each other's journey and growth has been, I think, on both sides of the coin. Uh, there, there's real pride for, you know, it sounds weird cuz we're in our thirties and like, it's weird to 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 gonna spend the weekend, just the two of us. We've had a lot of, like, we went to Disney World two weeks 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 wanna 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 calendar, 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 just 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. 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. the naming things really help, but also, The reason I think naming things is so valuable is that once you name something, oh, like I'm feeling anxious now. 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 gonna be a tough day and I can prepare for a tough day because I've pattern matched. And on days like this, I usually leave my desk feeling pretty exhausted. 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 Eisenberg I wanna be. Um, The better off you are. And I think that's something that I've 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 gonna crumble. And that's not the case. You can still be highly productive and very, very impactful, but also have the acknowledgement that like, I'm not doing great at this particular.

Greg: There's something about where we grew up and how we grew up that equips us with hustle blinders you know, out of the wo. , and I'm curious if you can shed some light around, how meaningful, you know, growing up in Montreal, being Jewish, being Canadian, and, you know, 99.999% of the people listening to this, don't know. people from that neighborhood. So can you explain a little bit, a bit more about.

Harley: Um, so first of all, there's this very, very 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 something that, you know, that, that you're excited, you're looking forward to.

And those are sort of what, Alexander Chalmers calls the three grand essentials of happiness or meaning, I guess is the way I would put it. I think there's a fourth one by the way, which is, the environment. I think you all seem to be in 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. second largest city, I think in Canada, maybe the third now, uh, but second or third largest, uh, it is the only city I think that is fully bilingual. Uh, 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 forties, fifties and sixties, 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, forced them outta their home again.

They ended up coming to Canada. Canada had a program where they. Led in 40,000 Hungarian refugees in in 19 50, 56. my father and his siblings, my grandparents came to Canada and came to Montreal at that particular time. So Montreal has been historically a, 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 created a place and 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 course is the schmatta company, like a clothing business that was, there was a big clothing company, but it was a city of entrepreneurs.

And In fact, the heroes of Montreal growing up were people like Sam Bronfman, who created Seagrams. Again, an immigrant that came to Canada, uh, from Eastern Europe, who created Seagrams or the Demore family who again, came to Quebec, uh, I think originally from Sudbury and built this crazy company, or the pedo, the Quebecor.

So, you were smacked in the face with these two, interesting ideas growing up, that 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, uh, aristocrats. They weren't Barrons or, or, or, or tycoons.

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. And I think that that instilled the sense of entrepreneurial, um, D n A, but also this identity that if you have an idea for a business and you grow up in Montreal, there's a very good likelihood that you're gonna probably try your hand at that.

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 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 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 part, 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. In 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, when?

14, 15.

Greg: Mm-hmm.

Harley: Right. So like, it just wasn't that uncommon when I went to South Florida. It was very uncommon. it was unique and, and, and somewhat alien.

Greg: So if you're not from Montreal or you're not from Chicago, you're not from la, you're not from Miami. what are some takeaways for people that they could wake up Monday morning and get into that Montreal mentality?

Harley: Okay, so I, I lo 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 law at the University of Ottawa in 2005, and, 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 a 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 other people like us. We had to build our own. And that actually led to, uh, fresh Founders, which was the group 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. Travel pod, uh, fellow, uh, fluid surveys, Shopify. Uh, it, it's kind of an amazing, interesting group of people. but we had to create our own, and so I've thought a lot about. you are not in a city that is especially entrepreneurial, know, you and I were both in Austin two weeks ago, right? I believe for for South by, I mean, there's this crazy energy in Austin. It's unbelievable. Right? And you and I have a lot of mutual friends that have moved there recently.

Like, you know, every second person you meet is doing a, like an entrepreneurial podcast and like every second, Physical retail store is a direct to consumer brand. I mean, like, it's unbelievable. I, I walked down, I think it was sixth Street and it was like, it was Aloe Yoga and then James per, and then tacos, and then All Birds.

It was like all these amazing Shopify 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 in a smaller subset, and you actually have to very intentionally create.

Greg: I wanna dissect that a little bit. So there's two pieces of that. So one, what you're saying is peers, basically having peers that can inspire you essentially. Um, the other piece is mentors, and I think you're a really interesting person with mentors because you have, in my opinion, a set of.

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, look up to someone like Seth Godden and, you guys would get along, but then you have a set of non-obvious tech, you know, mentors

Harley: Yeah. it is unbelievable, uh, to me, even to this point that I, I have relationships with, with these incredible, people, and some of them are, are very well known. You mentioned Seth and, uh, I, 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 listen, access to non-obvious potential mentors who unequivocally will change their life if all they did was reach out. And so, as I got married and had kids and, our business at Shopify continue to grow, is just beyond the lookout for people that I find to be really interesting in one particular aspect.

So either, you know, great relationship, great parenting, uh, they have a certain ua de Viv, like a, a joy of life. and forget about age. Forget about their net worth. Forget about like I'll say this sentence isn't just blowing smoke. Like I really look up to you, Greg, and, 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, of business creation and community building around and, and using community to build and incredible businesses. And you're just doing this, like, you're like, fuck it, I'm going to create this incredible where it happens program and I'm gonna do it.

full on. I've just on, been on the lookout for all these different people, and so what I've started to do more recently is take the next step and say, look, like I, I, I know this is kind of a weird thing, but like I notice how you are. You know, with your spouse, I 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 are so, mindful and so present with your spouse? 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 to hold hands also, but like, you guys are always holding hands like, what's that?

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. They're, they 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've enjoyed this so much that, um, I recently put together 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 seventies, eighties, and nineties, and just ask them questions about their life and ended up recording the whole thing.

Because I think that I wanna create an archive of these stories, but you realize as you meet these people that are again, non-obvious mentors, how much they have to teach and how nobody. Is no one has heard their stories and so non-obvious mentors actually, A non-obvious amount of alpha, 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, older Jewish entrepreneurs who came to North America with literally nothing and have built multi-billion dollar companies and have, have, have created the largest charities. In some cases, they brought Major League baseball to a new country like Canada.

Uh, in the case of, of, of Montreal expos. I wanna understand how the hell that happened. I want to know like how that all went down. I want to know, you know, the person that that built, you know, 20 skyscrapers. I wanna know how that person first got their, their initial round of financing to build their first skyscraper at 24 years old with no experience. one else has been asking those questions. no one else has been going after those people and saying, can you tell us your.

Greg: Yeah, so love this. First of all, just absolutely loving in this. I think, uh, yeah, this is great.

Harley: You would love, by the way, like big shots not out yet. The first episode comes out tomorrow. Uh, and 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 delicate contestant, 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.

Greg: Yeah, so I'm not gonna say where I live, but I live in an island where the average age is very. So I spend a lot of my time just sitting in hot tubs with old people,

Harley: You should turn, you should record those conversations from the hot.

Greg: And I know that sounds weird,

Harley: No, it, it doesn't sound weird. It sounds amazing. If they're, if they're having interesting conversations and you are getting access to those conversations, I mean, these are people that have had three, four lifetimes compared to us.

Greg: Yeah. Yeah.

I wanna double click into the alpha 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? Like if everyone is saying, Hey, go build a startup like X, Y, Z on Twitter, then.

you have a smaller moat.

Harley: Yeah, you know, um, after we had our first child, after Bailey was born in 2016, My wife and I would go for these walks every day. Newborn baby, like can't do much. So we went for these walks around our neighborhood, um, here in Ottawa and Lindsay, my wife had said, Hey, you know, I, I, I would love to go for some great ice cream.

There's no ice cream shop. I'm gonna create an ice cream company. I'm gonna create an ice cream retail shop, uh, called Sunday. And of course, like, I'm like, I'm, I'm the poster child for entrepreneurship. I'm like the physical manifestation of like the entrepreneurial spirit. Uh, at least I hope I am or try to be.

And I was like, Lynn's great idea. Let's do that. And she's like, great, who do I talk to? I was like, I have no idea. Lindsay's 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 school like was rocking like, the setup, the design, the production, uh, every aspect of Sunday school was like, This is like me being very proud of my wife. Like it was fucking perfect.

It was so well done. And one of the only reason that Lindsay was able to get that insight was because she didn't listen to me. She didn't call Ben and Jerry. She didn't call Hogan das. She didn't call Baskin Robbins. She called these like, These fairly, unknown or non-obvious ice cream entrepreneurs, and she began to network in that community and they gave her all this amazing insight.

And if she would've listened to me and she would've called Ben and 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 non-obvious ice cream mentors and she was able to build an incredible business doing it. And they were so happy to hear from her because some of these ice cream entrepreneurs are in their sixties and seventies, some of them. One, one of 'em was in, uh, was 85 and they were worried that there the next generation of ice cream, business owners, ice cream company, business owners wasn't around.

And so they 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, a disproportionate amount of their time relative to what she would've got if she would've called someone that I was gonna recommend.

Greg: I think a big takeaway for, for people listening to this is you wanna surround yourself non-obvious. Like it's good to have these non-obvious, for example, ice cream entrepreneurs, but it's also good to have the Harleys or the Ben and Jerry's also, and. thinking about, maybe you start not obvious, but over time you can scale with like, oh yeah, I, you know, now I can call Ben and Jerry's and scale this thing.

Harley: Yeah, exactly. At some point if, if Lindsay was looking to raise money or, you know, uh, for, for the ice cream company, I think that Ben and Jerry's could be helpful. Um, uh, I think Ben and Jerry's actually is owned now by, by, by a large C P G 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 about this non-obvious mentorship 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, 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 gonna find in any business Book

Greg: Yep. Absolutely. I need to, I need to share two small but big wins that I've had in the last three weeks with you that I, I

Harley: with me. Wow.

Greg: 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 gonna meet my heroes.

So I dmd Rivers Cuomo, who's the front man of Weezer

Harley: Yeah. Amazing.

Greg: 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 Ferris or Seth goin. So I dmd it, , I basically said, I bet you hear this a ton.

Your art has been life changing to me often in LA would be cool to hang out sometime. And he responded instantly

Harley: Wow,

Greg: 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 gonna be in Tampa in a couple weeks.

come hang. So I go to Tampa and I

Harley: You, you went to Tampa to meet him.

Greg: I went to Tampa to meet him. Car breaks down midway through, of course, you know, just, just in the Everglades, which for, for people who know Florida, it's like there's alligators

Harley: Yeah, is, it's

not a great place to have the car break down,

Greg: no 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?

I'm going to the show. So I go to the show, I meet with him backstage, and I have this 20 minute, 30 minute, whatever it was, conversation with him around, like rock and roll and music and programming and all these different topics. And I left that show just being completely inspired. And my, biggest takeaway was you'd be surprised who would respond to your dms.

Harley: And by the way, that like if, if you wouldn't have responded, the cost of failure is literally 30 seconds of your time.

Greg: correct.

Harley: That's all it is. And I, by the way, I love, I love that. I, I especially love it because what you also realize is that. what he probably learned from you about the future of music and the future of distribution and the Weezer community and like what that Weezer, you know, Africa, uh, album did like, like I rediscovered toto through Weezer. right? Like it's an unbelievable thing that like, like he, you probably dropped all this great knowledge, insight 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. 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.

Greg: Well that was the cool thing at the end, he was like, I'm gonna Orlando right now, but we gotta hang out soon. We're hanging out soon. And now he's like, I, I could say like, rivers is my homie, you know?

Harley: That's amazing. That's amazing. I, I, I did swimming recently, uh, during the pandemic, um, I sort of saw or heard that, uh, Tom Green was moving back, uh, from, from LA to Ottawa. His parents live here, and I ran. We sent him a note and said, Hey, Tom, a huge fan. I grew up watching M T V and watching the Tom Green Show, and I think you're super cool.

And we, we, we hung out. We've hung out a bunch of times. In fact, I think I introduced Tom to. As well. Um, and now like Tom is like introduced me to his friends. I'm introducing 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.

Greg: So what advice do you have to people who, you know, have a target list of, people who could be role models and mentors and like, , like, what? What do they need to type in the DM for? For someone like you to open it up and read it and reply.

Harley: I find for some, um, the DM is really, really challenging sometimes because they have a lot of things coming in and, and a lot of people coming in and a lot of people messaging them one, one other way. That's super simple. almost everyone you want to meet has some sort of, um, not everyone, but most people have some sort of philanthropic charity foundation they're connected to.

That means 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. Cuz I've, I've tried this $18, uh, to a, 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, in their honor.

and then you DM them. Now it's like, now, now you have two different touchpoints. Now all of a sudden they're like, I keep seeing this guy's name. Like, like who the, who the fuck is Harley 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 and a nice review. You can create something that is number. 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. Means that it means that you have also contributed. Like you were sending 'em text messages, you were, you were reminded of something that 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 wanna 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 shared experience, some sort of shared centerpiece of interest or connection. And so if you marinate that 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 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, a one time. Let me pick your brain. Here's 10 questions and then never call them again.

those people are never gonna be, quote unquote, 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, what 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, 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, it's authentic even though it may have started from what seems like a business pitch.

Greg: So step one is do your research. Like do do your proper research. Do your Danny Miranda style research

Harley: Dan, shout out Danny Miranda, man. He does his research. Danny Miranda found out where I went to high school, uh, and drove by the high school before he interviewed me cuz his grandparents lived nearby. Like, holy shit, that's like next level research.

Greg: That's why I was like, I'm not even gonna do research for

Harley: Don't just, just listen to Danny Miranda's podcast.

Greg: Exactly. So I did that. Um, do your research, so know, know what's important to them through that. Step two is, I mean, you want to craft a short and sweet message too, right? Like you can't, you don't, don't have like a novel, don't send a novel.

Harley: Yeah, no novel is bad. And hey, can I pick your brain as.

Greg: Yeah. Don't, yeah.

Harley: High context, like Yeah, right. Like, like high context, thoughtful. Don't waste their time. And if there's a connection, I mean, 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 Bell E Tea, or it's big shot, or it's my wife and family, like I'm so public.

There are so many intersections of me with pretty 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 had to figure out, you know, one of the people that I interviewed recently was this guy named Aldo Benun. Do you know Aldo Benson?

Greg: I do. Yeah.

Harley: 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 into a multi-billion dollar empire called Aldo, the shoe company.

Any city in America, in the world, you see Aldo Shoes. He built that from one single shelf and. His, his story is not out there. So having the, the, the way that I was able to first make contact with him was I remembered that I'd met him at a, at a bar mitzvah that I DJ'ed literally 22 years ago. I remember when I was like 18 or 19 or so, I deed a party. He was there and he came up to me and he said, you know, you're doing a great job or something like that. And 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, sit down with me.

So like. There are ways to contact everybody and, 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, if you're, if you're smart about it,

Greg: I have a fun Aldo story.

Harley: what, what is it

Greg: So when I was 18 and this and this, this is all gonna relate. When I was 18, I cold emailed Aldo probably 70 times.


Harley: literally like


Greg: n actually N didn't get a response. So then I went one layer, you know, I was like, okay, who's in his circle? And I, I reached out to their head of marketing.

At the time

I reached out and she gives me the time of day. Sh I'm 18 years old and I'm like, I wanna redesign all those website. I mean, they have how many store? They had, like 1400 stores at the time.

Harley: Yeah, I think at their peak they had 14 some of 1500 stores around the world.

Greg: Yeah. Amazing. And. . I, I earned her trust.

And then she said, you can 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 thirties, cuz I needed, like someone, you know, I, I bar, I still had like a

Harley: I was gonna say like gray hair, but they didn't have gray hair. They're in their thirties.

Greg: and I'm so excited. I'm like butterflies in my stomach. Prepared this whole presentation for him. a picture of like a boardroom. 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 were offended. That he, they got two minutes. I looked at it like, I've got two minutes.

Harley: It's amazing. Are you kidding? You got two minutes with one of the most iconic entrepreneurs on the planet.

Greg: one of them walked out,

Harley: One of your partners walked

Greg: walked out, and I was in this position where I was like, what do I do? Right?

Harley: mean, you got the meeting also, right? Like it was, it was, it's your name on the line, not theirs.

Greg: Not the, 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 gonna make these two minutes count. And I just said, okay, screw the presentation. I'm just gonna have a conversation with Aldo.

And it was an incredible conversation.

Harley: So, I mean, the lesson there and, 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, uh, five seconds someone's time, who 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, is it shitty that you 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 someone on his team and he's giving you two minutes, which has an opportunity cost because you can do, 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 two minutes into four minutes and, and what I'm gonna say in the next two minutes, hopefully gets you to sit down and spend a little bit more time with me. And if it doesn't, I just wanna say I'm super, super grateful for the time and frankly, I really look up to you and admire what you've built. And one day I hope to have half your. 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, I think being the guy that doesn't get, or the person that doesn't get offended and doesn't get up and walk, walk out, that's the way.

Greg: I think this is where we end it so. I really want people to listen to your new show. Where could people go to do that?

Harley: Yeah. 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 Bigshot 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 some of the greatest entrepreneurs that I know, they're mostly Jewish entrepreneurs whose stories have never been told.

Um, We just basically record the conversations and it's part documentary and part, as I said, kibitzing in a Jewish deli. Uh, but you can find it at Big Shot Show.

Greg: 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, you

Harley: Yeah, it, it, it's, it's basically, it's, 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, and also, I mean, in some cases, these are people in their nineties who, whose stories, you know, change the world and, and they're not on the podcast circuit.

They're not, they're, they're on social media.

Greg: All right. Take care.

Harley: Thanks, Greg. Appreciate.