How to Network with Billionaires with Andrew Wilkinson | My First Million Ep. #174

Hey everyone, we have a special episode with Andrew Wilkinson. I'm going to tell you about him in a second. I think you're going to like this episode, but I have a huge favor. So look, Sean and I, we spend a ton of time preparing for this podcast, like hours, tens of hours a week, 20, 30 hours a week preparing just for these two episodes. And I know it sounds like we're kind of shooting the shit and in a way we are, but we actually work so hard at it and I need a favor from you. I'm begging you, please leave us a review in iTunes. So if you're listening to this on Spotify, just click, click your podcast app or whatever it's called on Android and go to the iTunes store and just leave us a review. Click 5 stars and just click like, I really like it, or leave 1 star and be like, hey Sam, you suck, whatever. But we need reviews. And the reason why we need reviews is we go higher up in the charts, and the higher up in the charts we go, the more listeners we get. And the more listeners we get, the more ad revenue or HubSpot money we can make, which we can then put back into the show and do more stuff. If you notice, we've hired a team to create videos. We've done that because we've been getting more views and we're able to invest more into this podcast. And we want to do more stuff. We actually want to go on a live tour this summer and we want to come to you. We'll do it for free, but we need to get more listeners. And the easiest way to do that is just to leave a review. I know you hear a lot of podcasts saying do this. Most of you are just like kind of skip this part, but for real, do it. In fact, if you do do it and you send me an email, sam@thehustle.co, or I prefer you do this, you tweet at me @TheSamParr and take a screenshot of your review and make sure I see it. And I'm going to call all of you out. Everyone who leaves a review, I'm going to call you out. I'll either do it on Twitter or I'll do this on the podcast, but I'm going to recognize you for doing it. So please, make that happen. I have a feeling that this podcast is going to get listened by a lot of people, and so, um, get that in sooner rather than later so I don't miss it. But go ahead and do that, uh, and it'll be a really big deal for us. So leave a review, please. Now let's talk about today's episode. So today we have Andrew Wilkinson. Andrew Wilkinson is a good friend of ours. He's really interesting because he does everything. So basically, Andrew started with this design agency called Meta Lab. He grew Meta Lab to like $50 million in revenue out of— based out of Canada, and it was very profitable, something like $20-30 million of profit on like $50 million in sales, something like that. And using that profit, he went and bought a variety of companies. And at this point they own like 20 different companies ranging from a bakery up to different types of software. So he just bought this company called Girlboss. He bought a few others. And on this podcast, we're going to talk about what companies he's buying and why he's buying them. He's also done a few interesting things. Like, you ever read about how someone bought a lunch with Warren Buffett? Well, he did that with a bunch of different investors, and that's really fascinating. So give the episode a listen. Look up Andrew Wilkinson, and he's on Twitter. He's very active. If you tweet at him, he'll reply. If you tweet at me, @TheSamParr, I'll reply as well. Shawn did not make this episode because Shawn has a 4-week-old baby. So that's why we're doing some of these extra episodes without him. But please leave us a review. Let me know what you think. Abreu, how did you rate this episode? I forget what you, you gave it.

I think this was definitely in the A's. We, we covered a lot of ground, a bunch of stuff. Andrew brought the heat as always, a bunch of opportunities. I think everyone's gonna like it.

A's. Today's episode is an A. Uh, that's good, I'll take it. What was your favorite part?

Uh, he had a ton of stuff on how he grows his network. Andrew's super smart. He has like a bunch of billionaire friends and kind of lays out his strategy of meeting all these people. And I think that's applicable to just about anybody listening.

All right. Well, everyone, give it a listen. Please, please, please give us a review. I'm telling you, I'll owe you big time. And it actually makes a huge difference. And me and Sean, we read every review and we actually talk about all of them. We'll say, is this person right? Should we keep doing this? Or this guy, uh, tease us for doing X, Y, and Z. Should we actually stop doing that? What should we do? So we read all of them. Leave us a review. Listen up. See ya. I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back. All right. What's going on?

Not too much, man. Beautiful day here in Victoria. What about you?

Nothing. We— I've been spending all my time on this podcast trying to make it huge. We've got some really cool stuff planned, and I'm excited to see it work out.

Yeah, I feel like you guys are really ramping up. There's a new episode in my inbox like every single day.

Well, what's— yes, it's going really well. And we did the math and we're like, if it grows, if the last 16 months repeats itself, um, it'll be— we'll be at a million downloads a month by like, uh, December-ish, uh, which is fine, which is great. But figuring out how to like hack this has been really hard. And so we're just trying to figure out how to make it huge.

Well, what's HubSpot? What's their goal?

Their goal— so HubSpot has a bunch of cool stuff that they're launching, basically like a bunch, a bunch of content initiatives including podcasts. And their goal is to reach a certain number. Like, I don't remember the exact number, but they say like, how do we get to 100 million monthly newsletter reads, podcast listens, things like that? So 100 million monthly audience.

And they've just done the math on, you know, if 5% of those people convert into HubSpot customers then it makes— it pays back the acquisition or something?

Well, no, that's across— that $100 million, that $100 million is across all their content. Um, it's not just The Hustle. And The Hustle right now, The Hustle, we have close to 2 million monthly or 2 million subscribers, of which like 50-60% open rate. So that adds to the, uh, $100 million. Um, and so this podcast accounts for right now $400,000-$500,000. Eventually it'll be $1 million a month. And then if they have other podcasts, that's another, let's say, $10 million. So then we're at $50 million. And then where's the other $50 million going to come from? And so that's kind of how they're doing the math. But how's it—

how's it changed for you going from like staring at your P&L every month, looking at the bank account, freaking out about invoices not getting paid, to suddenly going, oh, I don't have to do that, I just have to focus on growing the audience?

Yeah, so it's pretty great. Like a lot of people HubSpot never said this, but a lot of people were like, man, you're only going to work there for like a few months or a year and then you're going to want to bail. And frankly, I'm having a great time. Like, I think I'm meant to start a company again. And I— this is my first job I've ever had, but it's been really great. And I can see myself doing this for a little while because it's awesome. Like, and like, let's like talk about the obvious, which is like I made money for myself. So like I can relax a little bit. I— it's not as hard. Like I'm working a lot, long hours, but it's not as hard because if I fail or screw up, like I'm not going to like cost people their jobs, do you know what I mean? Like if I make a wrong decision, I'm not necessarily going to lose a lot, a significant amount of money or someone's going to have to be fired because I can't make payroll. So that the lack of stress is so good. Have you ever—

Have you noticed? Have you noticed like your cortisol levels are dropping and you're just more chill? Interesting, dude. I've never felt that. I've never felt that because I've always had— there's always been so many different businesses that anytime we've sold one, I've been neglecting another one for a year and then that blows up and I get all stressed out. So it's been I've been thinking about this a lot, but I've been going from stress to stress for, man, like 7 or 8 years probably since we sold one of our first companies. And I've been thinking lately, I'm going like, holy crap, I got to de-stress. And that sounds really nice to not have to think about any of that stuff.

Well, the way I described it, so when I described, when I moved out to San Francisco and put my stake in the ground, like, all right, I'm going to figure this out. I felt like I'd been living with poor eyesight and I finally put glasses on and I'm like, oh, this is the world. I can do anything. I could do this. I could finally see. Now after selling, it's like a different— put my glasses on and realize I had poor eyesight where I'm like to my wife now, I'm like, oh my gosh, is this how you feel all the time? Like you don't have to worry about X, Y, and Z. What a crazy feeling. This is actually quite nice. Now I want to put that stress level back on again eventually, but it's nice having that break. And what I think about with you is I am envious of what you have in some regards, right? I think we're always envious of other people, especially our friends. I'm envious that you've built this huge, awesome empire that you own nearly all of it, that you have virtually all the control. That's very— most people envy you because of that. But I also think to myself, wow, Andrew also hasn't chilled probably for a minute. And that's definitely the downsides. And so like, in order to be the best, you definitely got to wear that, which you are. You have to worry, uh, carry that worry backpack a fair bit.

Oh yeah, it's crazy. I mean, it's so funny, like the numbers just get bigger, right? So it's like, I, you know, I, I remember in like 2012, one time we like did payroll and we didn't have enough money. And my business partner literally lent me money out of his personal account to close payroll. Right. So we've been at that level of stress and I never feel that now. We have enough money to go for years or whatever. It's a very different thing. But there's still that feeling of like, oh, fuck, there's like 600, 700 people relying on me to pay for their meal ticket every single month. And there's just constantly people problems. Right. So, yeah, I've got a lot of control and buck stops with me and a lot of the things that people might envy. But at the same time, we've got 30-plus companies and there's always a problem to think about or whatever. And I'm realizing I'm just constantly— I think I'm addicted to cortisol and stress. And this year has been extra difficult because what I used to do is I'd work at a cafe. I'd wake up pounding stress, cortisol. I'd be all pumped up. I'd do 3 or 4 hours of focused work, get all the stuff I need to get done. But then I'd go work at a cafe and my buddies would show up and we'd start shooting the shit and go for a walk. And play tennis and just kind of fuck off. And now with COVID it's like I'm in a house from 8:30 in the morning until 5:00, and then I go see my kids. And it's crazy that just the importance of distraction, you don't get that. Right now, working remotely in a house, you just don't get those moments, the automatic breaks and stuff. And so I'm realizing, man, if I'm left to my own devices, I'll just stress to the nth degree. And just keep working.

Do you think— this is the last question I asked about this because I think I always try to be self-aware where it's like, oh, a bunch of dudes complaining about shit that maybe like, is it like—

it's problems, right?

Yeah, well, my reply to that is it is a great problem. It's— but great problems are still problems. First world problems are still problems, but they are first world problems. But, um, do you think that it will ever get not sure or ever not be stressful? Like You know, we, you talked about Dan Gilbert last time, this billionaire guy who's got all this stuff going on. You said that he was pretty calm and present. Do you think that even a guy like him who kind of has it all, or I mean, people think you and I have it all, I imagine, but a guy like him who we think has it all, do you think that they still stress?

I think it's interesting. I think Dan's probably really stressed out, or at least was, because he has so many different things that he's responsible for where if he doesn't intervene, it messes up. There's different versions of really successful people though. Think about it. Is someone who runs a private equity firm where they have this big pool of capital they oversee and they just buy businesses and they oversee them or whatever, or someone who, like a hedge fund manager who buys stocks, right? You can have 20 employees, you invest in Apple and all these companies, and at the end of the day, Apple does well or it doesn't, and you don't influence that, right? I think the number of things you influence is what causes the stress. And I think in our business, we go, Oh, man, if I'm not scanning the sky for issues in all of our businesses, we could lose something or mess up. And I don't know, it's a double-edged sword because think about your parents or old people and they get upset about, oh, the neighbor moved in who doesn't want to water their lawn, or someone's dog keeps pooping on their front step or whatever it is that stresses them out as much as you and I get stressed out about business stuff. So I think everyone's programmed to be stressed, and I think it's more about what tools do you have to distract yourself from the stress? And if you got a lot of those, then you're happy.

Okay, so let's— we're— here's the tool that we're going to de-stress you. Perfect segue. So for the first topic today, we are going to talk about things that both you and I have invested in. Most of them are going to be things that you've invested in, and we're going to spend— we have 1, 2, 3, 4, 5, 6. Okay, we're going to spend about 3 to 5 minutes depending on how interesting they are, where each other, whoever listed it on here, we'll say what it is and why it's interesting. And then I want to comment and tell you what I would do if I was you and you and vice versa. Um, but I want to hear your intel or your, your, your behind the scenes look as to why you are investing in this and why it might not work and why it will work, like why it could work. And so, uh, does that sound good?

Yeah, sounds great.

All right. The first one, you bought this company who we've had Sophia Amorosa on the podcast. You bought her old company called Girlboss. Is it just girlboss.com? Is that the URL? Girlboss.com. Yeah. And what is it?

So Girlboss is like a media company for women. So Sophia started it about 6 years ago and built up this massive following, started doing amazing events, podcasts, built like a social network. And she— I met her when she was first starting it, and she'd done Nasty Gal, which was like this big Flameout, where she built a really amazing business, was doing $30 million a year doing online e-commerce, selling used clothes, doing really, really well, right? She didn't need the money, and she ended up raising from venture to take a little bit of money off the table. And then the venture investors got in and were like, hey, you got to 20x this, go take risks, start retail stores. She starts the retail stores and it all blows up. A really horrible story where she had a good thing and then she risked it and then it blew up. And so she was fresh off of that and she said, look, I'm starting this company, Girlboss. I think I want to bootstrap it and I might raise a little tiny round, but I'm not going to raise venture again. And so we ended up investing and following along and she ended up raising venture again. I don't know what it was specifically. I think she saw a bigger opportunity and decided to do it and the terms were great. But so she raised venture and decided to build all this stuff, like a social network for women, building an app, all these really expensive R&D projects. And it got to a point where it just wasn't working and it wasn't venture scale. And so she sold it to these guys, Attention Capital, in New York. And they—

they're Joe and Nick, right? I think they're—

yeah, great guys. Yeah. And they Yeah, they basically focused on the event business. They had all these massive contracts that were booked, and then COVID hit, and they just got themselves into a pickle where they just couldn't— the numbers didn't make sense. They were burning too much money. They lost all these contracts. And so they nudged me and said, "Hey, would you be interested in buying this?" And I said, "Look, I will buy it only if I can just buy the assets," because we looked at it and we said, "Hey, they've got 2 million social followers, they've got a huge newsletter, they've got a massive podcast feed. All the pieces are there, but the cost structure was venture, right? So they had a big P&L, they had a ton of employees. And we looked at it, we went, okay, what if this company had 5 employees? Could you run it with 5 employees?

Is that how many you have now?

Now I think there's maybe 7 or 8 or something like that. But we started with basically one person doing newsletter, one person doing podcast, one person doing social. And then we just said, as we sell more ads, we'll hire more people. And we ran it like a bootstrap business. And so that's what we've been doing. And I think, you know, Sophia was pretty nervous when we bought it, right? She's like, don't embarrass me, you know, make sure you hire the right people. And so we worked, you know, in close partnership with her. And she's actually been really stoked about what we've been doing. So that's been awesome.

Yeah, I just— you just, you just announced a new CEO, I think you hired.

Yeah, totally.

So, okay. So can you talk about any of the, like the size? So he has 2 million subscribers, 2 million social followers. How many email subscribers?

About 250,000. So I can't share the acquisition price. That's fine. But it was, you know, it was, let's say, I felt it was a value investment based on the social followers. But if you looked at it on a P&L basis, it was like, holy crap, this is a mess, right? Because they had been losing a lot of money.

Okay. What would you be happy with this company in 2 years? Like how much monthly revenue?

Yeah. What's cool about it is when we buy a business, we're generally going, if we're wrong about all the big opportunities and we're only right about just base hits, so like, hey, we've got 250,000 newsletter subscribers, can we sell $40,000 or $50,000 a month of ads on that? If we do that, we've got a good little business. And then if we do that on the podcast, we've got a really good little business. And then if we do that on social, again, it's bigger and bigger and bigger. It doesn't need to be huge. Based on the price we paid, it could do $3 million a year in revenue and be an amazing business and give us a good return. I think it's a $20 or $30 or $50 million a year business once we kind of do the events. We've been thinking about all sorts of opportunities within the business. But what I like about it is, you know, if we don't do well, if we don't grow it into a huge company, we'll still, we'll still do just fine.

So I agree with that assessment. I actually think that so long as you're mildly competent, which you are, the worst case scenario is $2 million a year. I would say $160,000 a month. Yeah. Based off of a quarter of a million email subscribers, 2 million social followers. Now it won't— wouldn't exactly be exciting or it wouldn't be the most fun thing. And that would be a, like, if that was the worst case scenario, it'd be like, man, we really missed, missed the mark on this. But you're not going to go out of business and you're probably not going to lose, which is pretty good. So I actually agree with that assessment. I think that if in 10 years, if you were at $30 million a year in revenue, I wouldn't be surprised. It would probably be It would probably be 15, uh, it'd probably be $20 million a year in advertising and $10 million a year in, uh, user revenue. So ticket sales, more likely than not. I don't know if you'd be able to get subscriptions to this. Maybe. I actually do think that there's— I know a few, uh, people who have, uh, female-focused communities and they do like $3 million a year in revenue. Oh yeah.

I'm seeing like much smaller communities doing way higher revenue. Like we've looked at a lot of stuff for M&A, like for even for Girlboss. And there's, there's definitely some people doing really, really well with small communities. So the way I'm kind of feeling right now, like everything I look at, and we're— I don't know if people, how familiar they are with our structure, but we mostly buy majority control of businesses and usually we're buying them from founders. And then off the side of our desk, we also do a little bit of venture investing, maybe like $2 or $3 million a year. We've got an angel list rolling fund for another, I think, $11 million or something like that. So my world is generally buying— So you have an $11 million—

Wait, hold on. You have an $11 million rolling fund?

Yeah.

That's crazy, right?

Yeah, it was insane. We literally were like, we tweeted it out as like an afterthought and we raised it in like 4 hours. It was totally insane.

$11 million?

Yeah, I think we're one of the biggest ones.

I think so. I think that, um, you might be like the second or third biggest. I think I heard of a $16 million one, but you might— you guys might be number 2.

We might actually size it up because you can— it's limited just by the number of people. And if you have, uh, there's no amount. So if someone wants to do $5 million, they can do that. Um, so there's some people operating more. Uh, we've got, uh, AngelList doing it. They administer everything.

And then who's—

I just Well, I decide, right? So basically, I already make probably one or two venture investments a month, and it's usually like a friend of mine emails me and says, hey, I'm starting a company, or one of our agencies is working with a company that we think is cool or something, and I just go, okay, well, I'll put in $100 grand. And now instead of putting in $100 grand, I put in $500 or $1 million via the rolling fund, and I just invest my personal money into the rolling fund. So anyway, so, so we do venture investing. I look at that as like a hobby. It's kind of like roulette, right? It's just betting on friends, having fun looking at companies. What I'm seeing in venture is absolutely insane. So I've seen companies of, with, with a founder who's a first-time founder with an idea, and they're raising at a $40 million pre valuation, right? Like just totally crazy stuff. And in the private market, there's all this crazy, just endless money and low interest rates and stuff. And almost everything we look at is just bid up like crazy to the point where we look at it and we go, I don't see any world, even if everything goes right, where we can make our money back at this price. And so for most of this year, we've basically just been sitting on our hands and waiting and trying to find hidden value. And the way I think about hidden value is kind of like Girlboss, where you look at the P&L, and it looks like, oh, whoa, this is losing a lot of money. I don't know how to value this. But you look at it and go, under our ownership, what can this do? And you make a new P&L in your head where you're like, oh, I actually need 5 people. My only costs are AWS and Mailchimp and stuff. And so we've been doing a bunch of that. And then really, we've just been kind of sitting and waiting and getting creative. Right. And I'll talk about this guy, Henry Singleton, later. But we really are just trying to issue stock when it's highly valued and buy stuff back when it's cheap. And so we've been looking across our portfolio and just going like, how can we do M&A with our stock? Or how can we buy cheap businesses and bolt them in that people don't understand? But it's crazy out there right now. Okay.

But to play devil's advocate, and this is something that I'm playing with in my head of like, what do I stand for? What's going to be my principles for investing? And I haven't settled on what those are yet. Though. I have some guiding principles. They're not solidified entirely. And a good friend of mine, Andreessen Horowitz, said, don't worry too much about valuation because whatever's hot will continue to be hot. And you're going to— like, a lot of times the valuations looking back will be like, oh, that was cheap. But then in the middle of it, it always appears to be expensive, but the real winners, it won't matter that much. Of course, his I think his lens to looking at that is quite narrow, albeit effective, but narrow. But what's your take on that?

Well, I think I'm assuming Andrew Chen, because I know you're friends with him. I think they're amazing investors, some of the best in venture. I think the hard part is if you'd taken that same approach in 1999, it'd be really hard to be a winner, right? Because you see the same kind of stuff happening where Historically, I think we're at an all-time high in terms of just pre-money valuations. But back then, I mean, there was companies that were pre-revenue selling for billions of dollars and all the same crazy stuff. And the problem is that within that haystack, there's an Amazon or an eBay or a Google, but you just don't know which one they are. And so I think if you were to go out and index and buy 100 random startups in 1999, you'd probably lose money. And I'd argue you'd probably lose money today if you went out and you indexed. And to me, the only way I'll bet on someone at a high valuation is if I know that they're a proven operator. Like if they're a founder who's done really well historically and I have a lot of trust and think they're amazingly smart, I don't worry too much about valuation. But dude, some of the stuff I'm seeing is just wacky, just crazy, crazy stuff.

Is there one thing that you are seeing that that interests you a ton that you've had the chance to invest in or you passed on, but you still think it's quite amazing? So you're saying that like you've seen, and I have too, like ideas from people who don't know what they're doing, or at least you don't know if they know what they're doing and they're these huge valuations. Is there anything that you've seen lately where you're like, oh my gosh, this thing potentially could be the coolest thing I've ever seen?

Well, I think if there's one thing I've learned over the last 10 years, it's when you see something and you get lit up about it, ignore the valuation and just invest, right? There's lots of companies that I was super excited about, but I was like, "Oh, I'm a value investor. I'm not going to do this on these terms." Like what? And I should have. I mean, I've got the ultimate anti-portfolio of Coinbase and Slack and all sorts of other stuff. I mean, running an agency in Silicon Valley for 10 years, you see all sorts of stuff, right? That turns out to be big. I think the thing I'm most excited about and nervous about at the same time right now is crypto stuff. And there's a company I saw recently that I didn't get the opportunity to invest in, but I think is genius. So the crazy thing about crypto is, at least theoretically, historically, if you were a member of a website like Reddit, let's say, and you're an early user, let's say you're the first 100 users of Reddit and you built it into something, you actually derive no value, right? You don't get paid. You're like a Wikipedia contributor, and then Reddit makes billions of dollars.

I know where you're going with this one.

For the first time ever, I could start up Andrew Reddit and I could say, hey, uh, all the people who move over from Reddit, uh, based on the number of followers you have or whatever your rankings are, I'm gonna issue coin in Andrew Reddit And as everyone moves over and posts more, you become more valuable, kind of like the Bitcloud thing. Now Bitcloud's kind of whatever BS, but I think for the first time, social networks and network effects are actually vulnerable to this. And one of the businesses I saw that I thought was fascinating was a company called Braintrust. And what they've done is they've basically created a really nice Upwork So it's like, uh, you go to the website, it looks like a really well-designed version of Upwork.

Is this Gabe?

Yes.

I know Gabe. I, uh, I know him too. He called me, uh, a year ago when he was about to launch this and he told me all about it because he was hiring a content person. Um, I have not checked in on this. Okay, so go ahead.

So I don't know what he was doing a year ago, but basically you go to this website and it looks like, um, you know, Upwork. It's like, hey, hire contractors for design and development, whatever you need. But then it says no fees. And I was like, well, how the hell do they have no fees? That's crazy because Upwork charges like 5 or 10% of all the projects. And what they do very quietly is they have a coin. And so they have a Braintrust coin and they have people who their job is to basically be a project manager on there. Those people get paid in the coin. All the transactions occur in the coin. It's almost like if Uber had issued a coin to all their early drivers, And then as they participate in the network, they get rich. And so they don't go to Lyft because they're already rich in Uber coin, right? And so it creates this lock-in and it aligns incentives. And before it was always this thing where it's like labor versus capital. And this is the first time it's all aligned. It's all, um, you know, very theoretical and early. And I don't know whether it's a good time to invest right now, but it's obviously the future to me.

Interesting. And so let's talk about this. So for the listeners, the guy who started this, his name is, uh, Gabe— what's his last name? Asta— uh, Astiokota.

He's got two—

he's got two last names, him and his wife. They've like hyphenated it, so I forget his full name. Anyway, he started a company called Luna Osta Seki or something. Yes, yes, yes. Um, he started this thing called called Cal— I forget what it was called. Caltech or no, not, uh, something, um, where it was like a lead gen site for like roofers and, uh, home services. And it grew to like $30 million a year in revenue. Um, I don't know how, but in some way he cashed out. Maybe his partners bought him out or something like that. And he started this thing, uh, Braintrust about 18 months ago, I think. And so I actually would email him after this and be like, hey, what's going on, uh, you raisin? Because this is really cool. Um, I think I agree with you, this is really cool. And he's a very proven entrepreneur. Now the thing I get nervous about when it comes to people like him, um, is that will they be hungry enough to make it big? I get nervous about that. Do you?

I don't really think too much about that because I think we all know like You know, you, you're going to have this exit and you won't be hungry in the same way where you're like, you'll claw someone's eyes out to, you know, to be successful. You've already become successful. But I think like over time, it's just like you start going like, okay, I proved it once. Now I have to do it again at double the size. And it's the same thing that everyone says where it's like, what's the perfect amount of money? It's like 2 or 3 times whatever you currently have. So if you exited for $30 this time, you got to exit for $90 next time. It's just, it's just the way people seem to work.

God, that's great. All right, let's talk about another one. Let's do— all right, I'll tell you this one that I just did the other day. And this one I actually think has more reasons why it will fail than why it will not fail, why it will win. It's called Tails. Let me find the URL. I don't even know. I don't remember. Tailswriters.com. So I just— I'm gonna text it to you. So on the surface, this has a lot of things that I don't like. It could— it's kind of like an iPhone game type of thing. Um, it's pretty hit-driven, but I'm interested for— in this for a couple reasons. The first, basically what it is, is, um, it's this technology where authors can upload their books that they've already written, and they've made it so they can turn a pre-written book into an interactive story, which is kind of interesting. Um, but I invested it for a couple reasons. One, I've been crazy fascinated with how authors can make more money because I think books traditionally are a horrible way to make money off of someone who spends like, you know, 2 years of their life writing something. Like it's pretty shitty. Like the different, like our friend Jack Butcher probably makes more money off his one course, which impacts probably 10,000 people than a book that is read by a million people, which is pretty crazy when you think.

I think this is fascinating though, because like I'm writing a book right now. I don't know if I'm even going to release it. I might just turn it into a bunch of Twitter tweetstorms or blog posts or something, or make a podcast out of it. Or that's what's interesting too, is when you have all that content, you can take it and put it across all the different channels, right? Like build it once, put it everywhere, and monetize it across all those different places. But there is a legitimacy. There's a legitimacy around being able to hand someone a book and say, this is my story as I want. You know, to, to, for you to understand it. And, you know, it's like Phil Knight is like the man because of Shoe Dog, right?

I agree. So that, that, like, I don't think a book is going to go away, but I think that what you should do is write a book as like a loss leader and then do all this other stuff, of which tales is one of those things. And the reason why this business fascinated me is because I think that romance novels and, um, anime and like entertainment like that for amongst young folks and particularly women. It's like one of the biggest genres there is. I mean, it's just a rabid fan base. People love this stuff. I invested in this thing because I think an author can charge like $30 for an interactive book and people will read it a lot and consume it a ton. And there's a company in China. I'm always fascinated with how the Chinese monetize content. There is a company in China called— well, the American translation is just called China Literature. It's an $80 billion publicly traded company that does something just like this in China. And I'm fascinated with how authors can make more money. I'm fascinated with bringing the Chinese habits to America. Also, the founder of this company had invested like $800,000 or something like that of his own money into the business. And I was like, oh, that's cool. Like you're, you're betting it. I'm interested. So that's a recent one I did, but there's so many reasons why this can fail. It could be incredibly expensive to acquire users. I don't know if the users are going to even stay for that long, and it could be a total hits-driven business. So this actually has a lot of reasons why it could fail and has a couple reasons why it could work.

I think the hard part about this though is that you've got to do all this custom work on each book. Like, I get they've built the framework, but you've probably got to have someone illustrate like a comic almost for every single—

So that's the technology that they've built is like they make it really easy for yourself, like you're the author, to make it interactive. So that's like the whole point. That's like the technology behind it. But we'll see if they can pull it off. It's been around for 12 months, so it's a working MVP, but TBD to see if this is going to pull— they're going to pull it off. But that's one thing I've just invested in. All right, your turn. What do you got? What do you want to go over? Which one?

So we just, we just, we keep investing in this business and it's a lot of people don't understand it. It's called MediMap. Medimap. All right, let's talk about Medimap. Can you spell it? Yeah, M-E-D-I-M-A-P. So up in Canada, we have socialized healthcare, so the government pays for it. And if you want to get care, you can't just call any doctor and get in, right? So there's this whole system. If you want to see a dermatologist, you have to go to a general practitioner, get a referral. It takes 6 months. In many ways, it's better because anyone who wants it gets healthcare. but the quality of care is probably lower overall. What it's resulted in is a system where a lot of people don't have doctors and you have to go to a walk-in clinic. There's all these walk-in clinics all over Canada. This guy came to me 5 years ago because I had invested in a few other healthcare businesses, and he goes, "Hey, I'm going to build this business called MediMap." Basically, You're going to be able to go to the website and you're going to see the wait times at every single clinic in Canada. And I was like, well, who's going to fill out the times? And he goes, well, I'm going to convince the clinic owners that they want to be on this site and they should punch in the wait times every hour. And I was like, this seems insane. Like, fuck off. I'm not going to invest. Comes back 6 months later and he goes, hey, I've got 25% of all clinics in Canada using this. And I'm like, well, how did you do that? And it turns out that every single clinic every day gets 10 phone calls a minute, and all the phone calls are is, hey, what's the wait time? Because everyone's trying to go where the lowest wait time is. And so there's this huge incentive. All the clinic owners went, oh my God, I don't have to have 2 medical office assistants. I can just have one, and that one can just punch in the wait time. Now, this business has 86% of all medical walk-in clinics in Canada, and every single one has software installed, WaitTime software installed on their computers. So we've been investing in this business. It's been losing money, and we've been building out this network. And our thinking is, once we have the network, there's a lot of really interesting things we can do with the network, and we've started expanding that. So it started as a venture investment, Then we ended up buying— we now have a control position in it. We're about to buy even more of it. There's a lot of models globally for this, like Zocdoc and other folks. So now that we've got the network established, we have no competitors. Even if someone raised $100 million, I don't know how you go out and convince every walk-in clinic owner in Canada to switch to your software over ours. So we're starting to now layer in physiotherapy, naturopaths, massage, all sorts of other services. And then we're also integrating into the booking engines for all of these. And these people can pay to promote their clinic and get more bookings and stuff like that. So I'm super excited about it. And it's one of those businesses you might look at and go, I don't get it, where's the value? But it's really, really cool and we're super excited about it.

Well, I'm on the site and I typed in my location. I'm like, oh wait, they're just in Canada.

Yeah, like type in Vancouver or something.

I did. I just typed in Vancouver. Okay, so, so the way it works is I typed in Vancouver, it says Crossroads Walk-In Clinic closes at 7 PM. As of right now, they've got a 30-minute wait time. I can click and I can join waitlist. And then I tell— I select what I'm going to tell the doctor and how I want to do the visit, yada yada yada. So how do they make money? Does the doctor pay per lead?

No, no, the doctor is totally free to use. And the doctor can— I believe the doctor can like make a nicer profile so they can upload their logo and stuff. But we don't make any money off of that, right? So the idea is over time we make a stronger and stronger network and we can start to get directly— like, like that one, you can click to join the waitlist immediately and do that. That's all free. What we make money on is when you go and you say, oh, I want a chiropractor, or I need to find a pharmacy and send in a prescription or something, we can do referral agreements with all those different clinics or pharmacies. But right as of right now, we haven't monetized it. Like, this is like—

how many people work there?

Uh, like 5 or 6. It's very small.

Oh, it's small. And it looks like you got, like, according to SimilarWeb, you guys are getting like 100-ish, 50 to 100-ish thousand, uh, visitors a month. And the traffic is mostly search and direct, which is like the greatest thing ever. I mean, that's exactly what you'd want. Um, so I imagine you are spending—

it's a unique database, right? Like, there's nowhere else you can go in Canada to get weightless time.

And I can't— I'm— so you're probably spending $0 on advertising, is that right?

Yeah, we, we've experimented a little bit with it, but we, we spend very little at this point. So it's going back to like understanding a moat and going like, oh, this is like, no one can compete with this. We spent the last 5 years losing money and building the network, and now it's like there's no way to disrupt this. And think of all the different things you can build in this. I always like to, um, say, you know, we like to buy airport businesses. And an airport is, you know, there's one, there's airport in a city, if you want to go somewhere and fly, you've got to go and sit in the lobby for an hour. And when you're sitting in the lobby, I'm going to try and sell you a bunch of stuff. So I've got all the stalls and I can put in a massage place and I can put in a bookstore, somewhere to sell sandwiches, whatever. And this is an airport business. And right now all the stalls are empty and we're going to start monetizing it and filling in all the stalls.

That's a great analogy or a great story. Where did you learn that one? Because before you had New Zealand businesses, which I like, where— who taught you? I made it up. You made it up. That's a good one. I like that one. That's really good. Uh, I'm going to steal that one. Uh, so like, yeah, MediMap, I could see how this is going to work. If I had to guess, I would say you've lost maybe $6 million on this so far.

Like, uh, yeah, I think that's, that's, I think exactly how much we put in. That was a good guess.

Yeah. Uh, I, I'm just doing the math as to you're not spending, you're probably only spending money on 5 or 6 salaries a month plus hosting, which comes out to be probably $85,000 to $95,000 a month. You've done it for 5 years. I just made that number up.

When it goes back to if that was in the States, it would have been more competitive, right? Because Canada— in Canada, healthcare is not privatized. Not a lot of people are moving into it, and there's just not a lot of venture competition. So if we're in the States, we would have had to raise $30 million, move super fast, be really aggressive. But we're able to kind of quietly go out and do this and build the network.

Is Zocdoc the nearest competitor? I mean, Zocdoc I think they're a multi-billion dollar company. Is that right?

Well, they're only in the States, right? And so I think they would be a logical— if they were ever to move international, they'd be a logical acquirer of MediMap. And I think that they're a great model. Right now we're looking at it and going, okay, how do we roll out the Zocdoc playbook or find similar businesses elsewhere?

I don't mean competitor, but I mean it's the Zoc— Exactly. Yeah, the nearest comparable is Zocdoc, and that's a multi-billion dollar company, I think. Yeah, that's pretty cool. I'm looking— I would imagine the thing with, with this company is going to be backlinks. And what's interesting about you guys is I'm looking at it, I'm looking at now you've got 750 referring domains, which is actually lower than I thought. You've got 7,100 backlinks. But here's why it's kind of actually interesting the way that you're doing it. None of your all your traffic, I imagine, is going to be search. Like, uh, it's going to type it— you're going to— someone's going to type in like, this clinic wait time, or this clinic phone number, and you're going to show up like, don't call, just click to see the wait time. But what's weird to me is, in Canada, do you guys have.gov websites? Is.gov only an American thing?

No, we have that.

It's like—

well, it's like gov.ca or something, but I think, I think we have.gov.

The reason I'm asking is is if this is— if most of your traffic is going to come from search, you are gonna— and all the— if some of these clinics are— I don't know how the Canadian, uh, I don't know how your guys's healthcare system is, but if they're a government-sponsored or a government-owned healthcare clinic, I would imagine it would have a dot gov.

This is the important distinction, is they're not government-owned, they're government-regulated. So the way it works is a clinic up— and they're, they're challenging businesses because the government basically dictates how much you can charge per visit. And the government has to approve them. They have to be run by a doctor. So it's basically like you can make sliver-thin margins. And that's again why having someone calling all the time, saving money on not having someone on the phone all the time is massive for a clinic owner.

But here's what I'm getting at. What I'm getting at is this actually could be a much bigger moat than I realized because if you're getting a bunch of.gov websites linking back to you, a.gov URL is worth— the SEOs out there will correct me— but something like 100 times more valuable than a.com. And so I'm looking at this website. If you could talk— if though, if I'm looking at your Medi— what's it called? MediMap. I'm looking at the clinics. If they all link back to you and many of them are.govs or.orgs or whatever, or.edus, if they're like— you're going to have a stupid amount of backlinks and you're going to have a significant advantage over anyone because you're just going to crush on search. Because Google, uh, any.govs are significantly higher ranked than a dot, uh, a.com and a.edu. So let's say you can get a university clinic or something to refer back to you. It's going to be actually quite amazing, I think. And I would imagine this is the type of company that's going to be slow, slow, slow, slow, slow, and then all of a sudden it's, it's just good. It's going to be like, oh, like no one's going to catch us.

Like nobody, nobody gets this and they go, oh, you know, there's all these virtual care, like Teladoc kind of stuff in Canada. And I just keep saying, like, well, when you break your arm, you're not going to go on Teladoc, right? That's a— this is like a certainty, like death and taxes certainty, is people will always need physical doctors. And yeah, virtual will be 20%, 30%, whatever, but it's, uh, it's not going away.

It's gonna— yeah, you don't— you— I'm not gonna call the doctor when I have a kidney stone. Um, so what—

why don't you tell me about, uh, Hustle+. I don't know, I don't want to—

I want to, I want to, I want to Do you want to do Hustle+ or can we talk about, uh, bakery and then cybersecurity and then—

Yeah, yeah, sure.

Is that okay? Totally. I want to talk about bakeries. So you— is this the bakery that you've already bought?

So no. So I own, I own a bakery. Um, I— when I grew up, my little brother worked at a local bakery just down the street from our house. And, uh, yeah, it was his first job and I used to go there all the time. I got to know the owner. I used to help him with his computer when I was 14. And he maybe 4 years ago said, "Hey, look, my parents are getting old. I want to retire. I'm thinking about selling my business." And I was like, "Well, I don't know the first thing about bakeries, but he's got a really good manager in place and I don't want this to go to the wrong people. I literally grew up going to this bakery. It's an institution in my city. I love it." "Fuck it." And so I said, "Fuck it, I'll buy it." And so I bought it and now I own an Italian bakery in Delhi and it's actually a good little business. It's like that thing I always think back to of like, if all this technology stuff fails and all my stocks go to zero, I always have a bakery. That's not going to go anywhere for 40 years. But the idea with the bakery, so basically a couple months ago, some friends and I did a paleo diet challenge. I felt amazing, but I had crazy carb and sugar cravings. I just wanted a treat, basically. And when you're doing paleo, you're not allowed any grains or sugar, and there's hacks around that, right? So you can be like, "Okay, I'm having something that's sweetened with honey or coconut flour or maple syrup or whatever." Those are all total BS, right? Those all still spike your blood sugar. If you eat a spoonful of table sugar versus a spoonful of maple syrup, It's pretty much maybe a little better, but equally bad for you. And so, I started researching non—

Who convinced you otherwise?

What do you mean?

I would've thought that that was obvious.

Yeah. I mean, a lot of people think like— I talk to friends of mine and they're like, "Oh, I gave my kids these really great snacks. They're sweetened with coconut sugar." And I'm just like, "Dude, sugar is sugar. And if you wear a blood glucose monitor, it's insane." So anyway, so I started researching all these non-sugar sweeteners and trying to think about how to hack this and make some snacks that I could eat. Like stevia, aspartame, all that stuff. And I realized there's this whole new generation of these. So a lot of the old ones, they have stomach problems, they cause dysbiosis or stomach cramps and other stuff. But there's new ones that actually taste really, really good, don't cause any blood sugar spikes, and are relatively healthy, like allulose and stevia and xylitol. And so I actually found a baker baker. I contracted the baker and I just said, "Hey, make me 5 or 6 different things. I want to see if I can make something interesting." And I started making these chocolate chip cookies and blueberry walnut cookies and all this other stuff, and they were insanely good. And so what I would do is I would give them to my friends and say, "Hey, I baked these cookies. Let me know what you think." And they'd eat them and say they were really good. And I'd say, "Well, there's no sugar and they don't spike your blood sugar and they're all healthy ingredients like almond flour and almond butter and stuff." And And so I started thinking about it and I was like, everyone wants to be healthy right now and they're used to going to a bakery and eating something unhealthy. Given the option, would they choose something that's higher end and healthy but still tastes the same or better? So think about McDonald's. McDonald's was the standard in the '90s. Now there's Chipotle. If you're a little more health conscious, you go to Chipotle. And so I was like, holy crap, I don't really want to get in the bakery business, but this seems like a great opportunity. So, I've been working on developing all these recipes and I've started making— Are you kidding me?

God, you are so funny.

Yeah. So, I'm literally starting a bakery. It's going to be delivery only to start just as a beta test, and I'm calling it Euphoria. And the idea is basically taste as good as a normal bakery, but it's actually really healthy for you. And I've worn a glucose monitor. I've done all these experiments.

Are you doing levels? What are you using?

I'm not doing Levels. I just use a Dexcom. But anyway, I'm beta testing it with a bunch of friends right now. And then in a couple of weeks, I'm launching it on DoorDash and going to experiment. But it's just like one of those random, you know, when like a business just like slaps you in the face. Yeah. And you're like, I want this for myself.

That's so silly. I can't believe this is so— this is very you.

This is—

I find this to be— I'm very envious of you for doing this. I think this is so freaking cool. How much— did you employ this baker full-time, or what are you doing with them?

You just contract. I found someone who can work part-time, and I'm just doing that to start. It's very like 80/20. I'm like, how do I invest as little amount of money as possible and as little time as possible to do it? So I hired a designer to do a logo and a simple website, and then I hired a baker to do the baking, and then a photographer to photograph everything, and that's it.

What's your startup cost gonna be?

Uh, $5,000 or $10,000 probably, maybe a little more than that. So again, this is probably a nothing, but it's one of those things like, at the very least, I just think it's something.

Yeah, it's definitely gonna be a something. I mean, is it gonna be like the thing? Who knows? It's definitely gonna be a thing. I mean, like, you— I feel like you kind of, you If you screw this up, you're kind of an idiot.

Like, yeah, well, it goes back to like, if I just called it a paleo bakery, even if it was unhealthy and shitty, it would do well, right? And then you add on to that, like, that, you know, the— all the glucose stuff and all the other stuff that's getting hot right now. I think it's quite interesting.

To summarize, I think this is such a great idea. Um, I think it will be fun. I think that it will make life worth— like, little stuff like this is life worth living. But maybe it could be immensely profitable. This is really smart. I have a friend named David Hauser who started Grasshopper. Grasshopper.

I know him.

Grasshopper. Everyone knows Dave. He's a good guy. Grasshopper was the software company that he sold, I think, for $200 million, entirely bootstrapped. It was basically like a small business phone service. You pay $10 or something a month and you get a phone line. He started this thing called Nut Butter. Is that what you know? What's it called? Called?

Uh, it's like a peanut butter pouch, right?

It's like a peanut butter— it's a keto thing. Um, and the business is so much harder than a software company, but he's having so much fun and it seems exciting.

Um, I think, I think like there's a— it's a double-edged sword, right? So, um, I, I used to always, I used to always ask people, like, you always get all these tech people who make tons of money or whatever, and you're like, well, you know, what are you doing with your money? Like, are you starting any weird things? Like, you know, I love Dan Gilbert, which I talked about in the last episode because he went, "How do I make my city better?" It's like doing the fun stuff with money. And the way I look at this is like, "Hey, I'm scratching an itch for something I want, my friends might want, but I make my city better." And it's a cool, fun thing to play with. I think the fun part of entrepreneurship is going, "This should exist," and making it exist. But at the same time, I've done stupid stuff like that. I started a pizza restaurant and I lost $800,000 doing it. It was a total disaster. I was getting phone calls. We had an alcoholic manager who was sleeping in the restaurant. We had a sketchy landlord. We had just endless stress and bullshit. And so this stuff is fun to a point. And the key that I've learned is just hiring amazing people. So I only like the beginning. This part is fun, but I got to get out really quick.

Have you heard of the Barber Motorsports Museum and Racetrack? No. So there's this guy in Alabama. Where is it? Somewhere in Alabama. Let's see. It's in Birmingham, Alabama, but it's in the country, I think, of Birmingham, Alabama. His name is George Barber. He's probably 80 years old now. His father— this guy's 80, and then his father started a dairy company. So like farming dairy company. Just like imagine like an Alabama dairy company. That's what it was. Sold it to Dean Foods for $500 million or something like that. And they were probably breaking it in throughout the entire 50-year period in which they owned it. He went with all the money, he went and started this thing called the Barber Track and Barber Motorcycle and Car Museum. And he has something like 1,000 or 2,000 cars. I believe it's the largest collection of motorcycles in the whole world. and he has this world-class track where IndyCars, um, um, like Rolex-sponsored Formula 1, uh, races take place on this. Like, people from all over Europe, Monaco, all come to Birmingham, Alabama to start and go to— or to go to this, uh, Barber racetrack. And it's done so much for the community. I think he invested probably $50 million to make it because it's a nonprofit, and you can look at how many assets they have and how much cash have and, uh, what their revenue is. And it's amazing. And it's similar to your bakery thing. Now, a lot of people, like, you think like, oh, how much can a car museum and a track help the community? Well, it actually helps it a ton because people all— everyone— I'm gonna go to Barber soon and take this lesson, yada yada yada. And, uh, that's my version of a, of a, of a bakery or saving Detroit is I want to start like a car museum and a car track. I think that—

I was talking to a friend about this yesterday, but Do you remember 10 or 15 years ago Portland was suddenly cool? Everyone's saying, "Oh my God, you got to go to Portland," or whatever. The reason Portland became cool was because of the Ace Hotel. The Ace Hotel was just kind of a funky hotel and had a photo booth and a good bar in it and all this other stuff. It was kind of new. And I always think, what's the Ace Hotel that you can add to your own city? In Victoria, it's like, what's the thing that people come to see? And right now it's like some twee English shops and there's a beautiful garden here and a few other historical things. There's nothing cool. And so I've been thinking a lot about this. Is it like a crazy bar or a music venue or a hotel or something like that? But what makes this place the destination? Because I think something as simple as that can change an entire city. I don't know what the answer is, but that kind of stuff is really interesting to Earlier you brought up Henry Singleton.

I like Henry Singleton. I've read this really good book called The Outsiders. I know that's probably your Bible, is that right?

I love that book.

Okay, so The Outsiders, um, it's a great book. It's about 12 CEOs who are quote outsiders. The, the commonalities is they are like kind of quiet, they're kind of afraid of the press, they are typically in locations like Nebraska or, uh, somewhere not Silicon Valley or New York, and they just get pretty good results, but they get it every single year for like 50 years. So they'll like grow something by like 20% or 15%, but they do it every year for so long that by year 20, 30, 40, it's like, oh my gosh, they're Warren Buffett, they're Henry Singleton, yada, yada, yada. Who is this guy?

So yeah, and the idea is basically that they're capital allocators, which is kind of a weird nerdy term, but it basically just means they, they're really good at putting their money into buckets where they can make a lot more of it versus investing in the wrong thing. And what a lot of people miss is you can have the most innovative CEO in the world, but if they misallocate their dollars and they put it into low-return R&D versus high-return acquisitions or whatever, you can have a very bad result despite being very innovative and a great leader and manager. So Henry Singleton is like— everyone thinks Warren Buffett's the greatest investor of all time, Henry Singleton, I think he died in the '80s, but I'm pretty sure he actually has a better record than Warren Buffett, and nobody really knows his name. They only know it because of The Outsiders. There's been one other book written about him, but he basically got into these very niche, very technical fields where they would do— It'd be navigation equipment that's on a fighter jet or random little diodes for circuitry and all this kind of stuff, but he'd find these niches where they could kind of own it or have a very dominant position in it. There's this very simple way of thinking about investing, and his whole thing was when the market is overvalued and crazy, that's a great time to issue stock and to sell things. And when the market is undervalued, you want to be not only buying back your own company, so if you don't own your entire company, you want to go and buy back more stock, and you want to be investing then. So that approach is very simple. It doesn't sound like rocket science, but I think it's a really important thing for people to be thinking about right now. And I think now is a great time to be scanning your portfolio or businesses and going, how can I basically take advantage of valuations right now and either issue stock or use my stock in my business to go buy stuff or just wait for opportunities? Because right now it's like a crazy seller's market.

Which is shockingly the hardest part. Is the not doing anything. So in time, like, you have far more perspective in this. You're more successful than I am, and you're a couple years older than I am. So you just a little— everything that I am interested in, you are, but more. How are you and other people who you've met that buy into this? How do you guys just sit and chill? How do you not do new stuff? Because I say to myself all the time, I'm gonna— I'm not gonna like pounce on X, Y, and Z. I got to wait. I got to wait. I got to wait. I get so antsy and I can't— it's hard.

Well, there's a reason I'm starting a sugar-free bakery, right? That's the stuff. That's honestly my secret to not doing too much is I distract myself. And before COVID it would be distracting myself with sports and playing bridge and hanging out with friends and going on walks and stuff. Now it's starting businesses and they're really small little businesses, they're like hobby businesses. You know, it's like me just kind of playing with $10,000 or $20,000, but it's enough to keep me distracted and happy and active and feel like I'm doing something. But in reality, I'm sitting on my hands and building up cash.

And what, like, you're— so you still have enough time to do that and do the e-commerce thing, which for those of you who don't know, Andrew, I don't know how you describe it, if you started it which you owned it. I don't know what the right terminology is, but you have this thing that went public and is currently like, I don't know what it is today, but like many hundreds of millions of dollars in market cap.

Yeah, we started a business about 10 years ago. We met the founder of Shopify, and at the time we were running a design agency, and he said, hey, we want to launch themes on our platform. We want people to be able to sign up and have different designs they can choose "and we'll let you guys sell these themes on the platform for $150 to $250." And so we were kind of thinking like, "Hey, it's a small little Canadian company. These guys seem nice. Let's do it." And we started doing it and Shopify just grew into a behemoth and we rode the whale and did really well. And we actually sold the business in 2013. We didn't realize how big Shopify would get. And then we bought the business back in 2019. We did a buyback—

Did you buy it back for more than you sold Way more.

Yeah, I think it was 5 times, 6 times. Damn. So we bought it back and we said, we're just making a big bet. We think Shopify is going to get a hell of a lot bigger. And we made a holding company called WeCommerce and we started buying businesses and kind of building a mini version of Tiny within the Shopify ecosystem. And then we took it public in December and we're listed on the TSX Venture Exchange up in Canada. Canada.

And as of right now, I don't know if this is in Canadian dollars or American, but it's $663 million market cap. I think that's US.

Yeah, I think Canadian.

That's Canadian. So $663 million Canadian dollars. So it's pretty big. How, but I mean, like you're saying you're like just sitting there not doing anything, just waiting and waiting, waiting. It seems like you're doing something.

Well, I mean, I'm, we started this podcast by me saying I'm stressed out and busy, right? So I think I don't want anyone to get the wrong idea that it's more I'm filling my time when I have it by distracting myself with this other stuff. And that all of the things I'm focused on right now, for the most part, while I'm looking at buying businesses, everything's so overpriced that I don't want to make a swing on the wrong thing. So I'm filling the rest of my time with other things.

And one of those things is not email. You told me the other day that you— For the first time ever, which is actually shocking to me, that's the first time ever you've hired someone or you've asked your assistant to completely manage your email. And you said something like, this is the first day I've tried it, TBD if it actually works. Is it working? And what are you doing?

Yeah, so I'm doing two things that are kind of interesting. So one, I fully delegated my email to my assistant. So I've started getting over the last couple years like 200 or 300 emails a day. Honestly, it was just making me kind of miserable. I've tried all the best practices and we even built a company called Mailman that basically slows down your email and does do not disturb on it and stuff, but it just wasn't enough. I hit my breaking point a couple weeks ago. I was just spending 5 hours a day doing email and I set up tech support software. I pipe my email into it and I have my assistant and then we have another assistant we have in the Philippines and they basically monitor the email and they have a set of rules. So I I wrote out, like, if someone asks me to sign a document, send it to this person on our legal team, they'll review it. And then if they say yes, you can sign it as long as it's below this amount. If someone requests an interview, go and look at the podcast, see how many downloads it gets. And if it's above this, you can schedule it or whatever. And so I made like 10 of these rules and now I'm getting like 20 emails a day because the only ones that come through to me are the ones where it's a friend asking me a direct question or it's one of our CEOs or a go/no-go on an investment. And so it just freed me up by like 2 or 3 hours. And it's a classic example of like the E-Myth kind of where you're like desperately doing all this stuff that you don't really need to be doing because you've always done it. So that's been awesome. What's the E-Myth?

I don't know what the E-Myth is.

Oh, you don't know that book?

I've seen it. I don't know what the myth is. I've never actually read it.

The E-Myth, The Entrepreneur Myth, I think it is. But I think that's the best— See, I always thought it meant electric Electronik. No, it's an amazingly badly written book, but it's a very important message. It was transformational for me 12 years ago. And the idea is basically when people start businesses, they don't build systems and they don't delegate, right? So the person who loves baking starts a bakery, and then before they know it, they're staying up until 2 baking, and then they wake up at 7 in the morning to mop the floor, and then they're behind the till all day. They're miserable, they're stressed, and thought they were creating this utopian business that they wanted, and in reality it just sucks and they're miserable. And the reason it sucks and they're miserable is because they don't delegate, they don't build process, they don't hire people. When they do hire people, they don't give them a chance. And so it's all about how to delegate.

Got it. Okay. And what were you saying about the email thing?

So, and then the other thing I did, which has been really fun, I used to like I used to do this myself. So I used to cold email, I still do it actually, I still cold email entrepreneurs that I think are really cool and I want to meet or ask some questions. And 5 years ago, I started getting emails from young entrepreneurs saying, "Hey, can you look at my startup or can you give me an opinion on this?" And I used to write really thoughtful responses. And then as I got more email, I just couldn't respond. And I felt really, really guilty about this. And I was just like— 100%.

Same.

I'd like delete it. Sometimes I just like delete, and other times I'd be like one-line response, and I'd be like, fuck, they think I'm an asshole.

100% same, dude. I've done that with some people, and then I've eventually become friends with them. And you know how like on Twitter you can see, like, you recognize people's thumbnail over and over? There's this one guy the other day that I've seen him talk to me all the time, and then I've been hanging out with this other person like through a friend of a friend like 3 different times now, and I knew his name and And I'm like, fuck, you're the guy I've been ignoring. I'm so sorry, man. I'm so sorry. I didn't realize it. So anyway, I do the same thing and it kills me.

Well, you never know who they're going to become, or they could have this great idea if you just talk to them and get on the phone. And so what I ended up doing, I realized I was actually doing myself a disservice by responding because I just say like, this is too long, write me a shorter question or whatever it is. You know, the douchey, like, I'm too busy stuff.

Yeah, yeah, like, I don't know what you're asking.

So now I write them back, I have a template, or my assistant writes them back and just says, hey, I don't respond to these via email. What I like to do is I do an AMA, ask me anything, every month. And if you can afford to, donate to charity just as a way of paying it forward or whatever. And so if someone's rich, if someone has a big company already, I'm like, hey, go donate some money. If they're a first-time entrepreneur, we don't expect them to. And then Chris and I just do a monthly AMA, and then everyone gets to enjoy the answer we do. So it's been crazy. So we've already donated $58,000 to charity from this. So we basically, whatever the community donates, we double it and then we donate it to a local charity. So we've donated $58K, half of which came from people who donated. And then it's probably saved me 2 or 3 hours a month of just not responding to these emails. So it's like a really great hack.

Should I copy that? I think that's great.

Totally. Yeah. Yeah, I think we made it up.

That's wonderful. That is such a good idea. Where'd you send the $56K to? Have you picked your thing yet?

We did one. One was like a— it's called Bridges for Women, I think it was. And it's for women that are transitioning out of abusive households. And then the other one was a gym, a local gym. Some guy set up a gym for handicapped people because there's no equipment for handicapped people in town. And so it's somewhere you can go and work out if you're paraplegic or something. Something.

What's the most amount of money you've ever donated or given? Can you reveal that?

Uh, I, I've given away probably like $3 or $4 million, I think, so far.

Wow, that's crazy, isn't it?

It's really, um, it's, it's really crazy. And I'm just kind of learning. I'm learning. I'm going like, how— what's the most effective thing to do? Because there's everything from like local feel-good, right, where you can help a small number of people, but you know, you're making their life 10% better, but you're not saving a life versus if you put the money into malaria medication or bed nets or that sort of thing in the third world. I think that's what I'm kind of debating right now is how to be most effective with my altruism.

I can't believe though, like you've given away that much money. That's a huge amount. I haven't done really much of anything and I want to.

The way I started was I, I just started donating to science. So I'd be like, as I was researching different medical things, I'd be like, "Oh, this researcher is really cool. I'm going to start donating monthly," and I just fund their work. And then over time, I just put more and more into it. And then over the last year, I started the Tiny Foundation. I don't know if you've seen that, but about a year ago, I started doing this thing where I would just find people who I thought were smart in fields that I thought were important. And I'd say, here's $100,000 to $300,000, you choose where it goes. So you donate it, it can go to your own research, it can go to a friend's, anything you think is important. And it just saves me from having to do all the diligence and work.

So I'm looking at it now. Even your foundation website looks pretty badass, which is awesome.

Yeah, we hired some really awesome designers for that.

Yeah, it looks really good. So for this, this, wow, besides just like doing good, which is like the most important thing, but let's just be real. Is there anything that you're getting out of this?

I mean, what I get out of it is—

Other than feeling good.

Well, for example, so I don't think I've talked about it on here, but I had acid reflux, like horrible acid reflux for 8 years. And I started researching it and I read tons of research about and I was like, "Holy crap, if you get esophageal cancer, you die. There's literally no treatment." And so I actually, one of the things I'm funding is an esophageal cancer research center at UBC. And so you could argue maybe I'm trying to save myself in the future, maybe if I get this. But other than that, it's a great way to meet interesting people as well. I've met all sorts of amazing researchers and doctors and all sorts of other stuff as a result But no, I mean, it's just I'm trying to figure out how to convert money into something other than more money and more problems.

Last topic, something I want to ask you about. I think it was a friend. I forget who, Nick or my friend Nick Gray, or I don't know who, I forget who said something about how one time you bought a charity dinner or charity lunch with actor Bill Ackman. And at the time everyone like made fun of you. Like, who's this idiot from Canada that would spend $50,000 on a lunch? I mean, they don't realize that that money actually goes to a charity as well, but they're like, oh my gosh, like this is so stupid. Yada, yada, yada. Turns out you actually became friends with Bill, I think. I don't know him, but I'm going to call him Bill like I do. And you guys have like done business together and I'm sure you've made that money back many times over, but you have this interesting way of networking. You have this interesting way of getting your foot in the door. One time on this podcast, you told a story about Warren Buffett. You've told me a couple people that you've been hanging out with, like, and like you've had, you're like, oh my gosh, I just did a Zoom with X, Y, and Z. And they're like pretty big deal people. What is your whole thing about networking? I mean, you were just talking about cold emailing. What, you have this weird philosophy about this.

Yeah. So I'm going to first to start with, I think networking is really fun if you're an extrovert and I'm an extreme extrovert, right? So when I feel depressed or sad, I want to be around people. I want to share my problems. I want to connect with people, right? So I by default do this. And I would say like starting about 15 years ago, I just started, I started seeing all these interesting people on the internet and going, wow, they seem amazing. I want to do business with them. I want to become friends with them. And specifically, there's all these people in New York who are big Tumblr users who just seem super cool, the founders of CollegeHumor and Vimeo and all those people. And so I started doing a couple of things. One of them was I never eat alone. So pre-COVID, I'd always have lunch with somebody, usually locally, and I'd almost always do at least one call with a random person who I either haven't met or I'm just building a relationship with, even if if it's like 30 minutes first thing in the morning. The other thing I did is I started paying to be in the right room. So I remember telling someone 10 years ago, I wasn't doing super well. I maybe was doing $15,000, $20,000 a month of revenue or something like that. And I paid $10,000 to go to the TED Conference. And all my friends were like, what the hell are you thinking? You're spending all this money on this. When I went to the TED, I have this whole thing about paying to be in the right room, right? So when you go to TED, it's like a secret club. If you get into TED, every single person that's there is someone interesting, and at the very least, they've paid a lot of money to be there, so they're legit. And being in the room, if you're in the room, everyone goes, oh, they're legit too. And so I was this twerp with this tiny little business, and I'm talking to Al Gore and the founders of Google and all these amazing people. And just being in a room with those people, you naturally, over the course of going consistently for years, you end up meeting all these amazing people and making connections. You end up doing business with them. And so my doing that, just going to TED and probably spending $30K on tickets for 3 years, I think it ended up resulting in $10 or $20 million of revenue for my various businesses. And so I'm a big fan of doing The other thing I like to do is host events. So I try and bring someone really interesting to town in Victoria, and then I invite a whole bunch of other people who I think are interesting. And then by doing that, you've basically made this collection of people where you're the host and you're kind of in charge of the whole group, and you get to meet the speaker and other stuff. And so an example of that is I thought Shane Parrish from Farnam Street was super interesting, and brought him out to do a speaking event, brought out all my favorite people from Victoria and elsewhere, and I ended up becoming friends with Shane. And now Shane is an investor with us, and we've done a whole bunch of deals, and he's a good friend. And so I think one of the things no one recognizes is there's an insane amount of optionality and upside in just knowing great people, both personally. You make great friends, but when you have a problem or you want to build a business or you need investors, Being able to call a bunch of amazing people is the ultimate hack. And so yeah, that same thing happened with Bill. I went into that charity lunch actually looking at it as a diligence thing. I'd invested in his company and I was going, "Well, if I don't like him, I'll sell it, and if I like him, I'll hold it." Yeah, yeah, yeah.

How much money had you invested? What was it called?

I had $5 million invested in his holding company, Pershing Square Holdings. Pershing, yeah. Yeah. And I don't do—

he's not a tech guy. Like, what the hell angle is this?

He's not a tech guy. I honestly didn't really think of it as like, oh, this is super strategic. I was going with, he's a really smart investor. This was in 2017, I think, or 2016.

And so that was 5 years ago. So you were like, what, 30, 31?

Yeah, 31 or so.

So $5 million, no matter what, is a lot of money, but at 31, that must have been a significant amount of your wealth.

It is my largest investment outside of the tech businesses.

And you put it all in his fund?

Well, I saw it was basically like Bill had a series of challenging investments, and so his stock traded way down. And when I looked at it, I was like, okay, I can buy a dollar of amazing It's really simple. It's a holding company that owned about 10 stocks. And if you looked at the stocks, it was Lowe's, Howard Hughes Corp, which is a real estate business, Chipotle, really good blue-chip businesses. And for every dollar of stock that was sitting in the holding company, you could buy it for 65 cents because the stock had traded down so much. So it was like buying a dollar for 65 cents. So I didn't necessarily think Bill was a genius. I thought he was a very smart investor. I just thought it was a very cheap stock, and so I bought it. And then when I saw this charity lunch come up, I was like, "Oh, sweet. I can grill this guy and see if I like him." And the upside is— How much did you pay? $57,000. And the upside is he's just a really smart investor, and maybe I can learn something from him. But he doesn't invest in tech, or at least I didn't know he did. So I didn't think I'd be doing business with him. It was like a pinch-me moment when we ended up investing in stuff together.

Um, what happened to the, the stock?

Uh, went up a lot. Uh, it went up, doubled or more, tripled or something since I bought it. So it's just done really well.

It's tripled. So the $5 million went to $15 million in a matter of 6 years?

Yeah, I, I think, I think I actually, it might have been 2018. It's either 2017 or 2018 I had lunch. Over the last, over the last few, few years, it, it traded way way up. He's done amazingly well. I don't know if you saw, I think you guys talked about it on the pod, but he had a bet where he invested $25 million and it turned into $2.7 billion. And that was in that holding company that I'm an investor in.

Oh my gosh, that is so funny. Um, um, but so back to the networking stuff, I got distracted.

The payoff is that's so cool. I mean, obviously for business, it's great. I really believe you're the sum of the 5 or 10 best friends or most interesting people around you, so I think it influences you really positively. But the cool thing that's happened is now it compounds. So now I don't actually do cold emails very often. I don't really consciously network. I just naturally every week or two, I get introduced to someone really interesting. And so now it's this like, uh, I planted the garden and now I'm enjoying the fruits from it.

My issue is I don't really want to talk to people like that much. Uh, like you and I text message, um, and I'm okay with text— like, I'll text— like, there's like 10 people who I'll text, uh, you're one of them. It's like, other than that, like, I really don't want to talk to anyone. And it kind of actually stresses me out because I don't— it doesn't stress me out because in one regard it doesn't stress me out because I don't want to talk people. Like, I really only want like a small group and I only want to be with them. And like, you're one of those people where I'll just text you and be like, hey, did you see the new 9/11 get released? Or like, we just bullshit, right? We don't talk about work. We just talk about, just bought this car, does this, this, check out this video, listen to it, it's cool. But then I feel left out because I'm like, I'm like, Sean does this a lot. Sean networks with everyone and he gets access to all this cool stuff. And I'm like, I want that access, but I don't want to spend the time talking to these people because I just get nervous.

Or you have the ultimate— you have the ultimate hack though, which is you, you have this platform, right? I've started realizing this too. There's a reason I come on. I have a lot of fun talking to you guys, but at the same time, there's 10,000 people listening and a whole bunch of them are super fascinating, and they're going to email both of us and say, hey dude, I'd love to do something with you, uh, or whatever. So we just bypassed The problem with networking is you do 5 boring calls and then 1 amazing one, right? So you're constantly talking to people you don't necessarily want to talk to, or they don't turn out to be that interesting when you think they will be. But it's worth it because there's a diamond in the rough. And I think podcasting is interesting because it lets you— you basically have 10,000 people who kind of learn what you're about, and they can either decide if they like you or not. And if they opt in and they like you, you've already pre- you've pre-sold them almost, right? When I get on the phone with someone fresh, I actually tell a story about this is how I started and this is my company and this is what we do. And it's not a sales pitch, but it's really like, hey, here's who I am. And you can just bypass all of that via a podcast or something.

Yeah, I hear you. And what I usually, when I'll talk to people, I'll be like, hey, I don't want to be pretentious or anything, but do you know I am. Um, yeah, because like I can save us time and I won't like do the spiel. Uh, they're like, oh, I listen to the podcast. I'm like, sick, I'm not gonna tell you anything. What's going on? How are you? Um, the other day I had this guy named Michael Loeb. Do you know who Michael Loeb is?

Yeah, he, um, he has an incubator, like a big, big incubator. His house is the house in Billions, the Hamptons house.

Yeah, so I like this guy. I don't know him other than the few minutes that I just talked to him, but I knew about him and I actually admire what I read about him. He started this thing called Synapse, I think, which he sold to Meredith— some— or Time magazine for, uh, $800 million. Then with that money, he started Priceline. Uh, he started with this guy named Jay Walker, and I think they sold that for billions of dollars. And I think it was the fastest time anyone has ever made a billion dollars, like from launch to like the sale or the, the public markets. It was like, uh, like a year or something like stupidly crazy. He got— made all of his money there, bought this huge house in the Hamptons, which if you watch the TV show Billions, Axelrod, Bobby Axelrod buys this house for like $100 million, like something crazy. And it's like, the whole point is it's supposed to be like the, the representation of greed and, and too much money. And that's the house that he buys. Well, that's Michael Loeb's house. And a couple years ago, he throws this party or a charity, actually a charity event and they raised like $350,000 for this event. But one of his sons has a friend over who gets drunk and says something smart to him. So Michael punches him in the face and gets arrested. So he's got this— if you Google Michael Loeb arrested, you'll see his mugshot. He's got like a white t-shirt on, like they clearly like pulled him out of bed. So anyway, and they found out that, you know, Michael Loeb is like this rich guy. So the dad of the son probably sued him, yada, yada, yada. Well, anyway, he heard— he didn't, but one of his assistants, someone someone must make a list of every young entrepreneur who sold a company, and they send you this email from Michael, and it's like, hey, I'm Michael Loeb, I'm such a fan. And like, I know this guy's like 60-something years old. I'm like, I don't think this is you, but that's cool. Like, it's your assistant. And he goes, hey, let's talk. So I talked to him and I could tell he doesn't know who I am, and it's no big deal. It wasn't like a disrespect or anything. But I was honored that he even reached out, or his people did. And he's like, so I'm thinking about hosting this event for entrepreneurs. Are you interested in coming? I'm like, dude, I'm not going to be pretentious here. I'm sorry if I come off that way, but like, you're talking to like the guy. I host these things called HustleCon. I do this, I got this podcast thing, I've got this email thing. Like, I've got your target demographic. And he goes, yeah, well, like, I'm wanting to host an event at my house. Have you seen, have you heard of my house? I go, yeah, I've heard of your house. Obviously I've heard of your house. It's like the house. And I've tried to convince him now to make me a co-host, and I don't think he's going to make me a co-host, but I hope he'll invite me to come to his house in the Hamptons where he wants to have like 50 or 100 young entrepreneurs. And I have a feeling what this guy does is he owns this thing called Loeb Enterprises, and I think he owns 100% of it. And it's very much like Tiny, where they invest a small sum of money into interesting ideas and they'll co-own the business with the entrepreneur starting running it, um, or they'll own it wholly and give the entrepreneur a salary. And they build up these companies and then they eventually sell them. And they've had some great success. They built up, I think, this thing called Script Relief, uh, did $100 million a year in profit. Um, they built up a bunch of interesting things, but related to networking, that, that's my networking story. And maybe I'll be hanging out with Michael Loeb and whoever he hangs out with. I don't know who he hangs out with.

That's so cool. I want an invite to that event. That sounds awesome.

I got you.

We got introduced to him when we were in New York last time. So Chris and I go to his office and he's like an old school, almost like a car salesman, right? We sit down and he's like, "Hi guys, I'm Michael Loeb." And he pulls out a slide deck, but it's not on a screen. It's literally a printed slide deck. And he goes, "This is my story." He has no idea who I am. He just goes through this slide deck and he starts going line by line about about it. I thought it was really charming and he seemed like a cool guy, but it was crazy. He definitely has a shtick and he has a system for this stuff. It was really interesting because his house is crazy. I haven't been to it, but I've seen photos and watched it on Billions. You go to his office and you're like, "Oh, it's just a New York office." It's some random crappy office. It's like chaos. There's like, you know, weird desks everywhere and like shitty chairs and disgusting carpet. It's funny, like seeing, um, you know, these— in New York you can be the richest person in the world, but it's like you still have to ride the subway, you're still— you still— you still have a cramped office, all this other stuff. It's funny.

Yes, I saw he videoed me and I could see in his office and it looked like, uh, all of his employees were at home except for his crew, and he clearly had like this very stereotypical— like, I didn't actually see this woman, but this is like— I could kind of tell that this person was in the background. This very typical, like, 50-year-old secretary who's had for, like, 30 years, who, like, I can just imagine her with her flats and, like, dress on, handing him coffee, and, like, she's this nice lady. I just— like, everything about him fit the stereotype, and frankly, I loved it. I think this guy is incredibly interesting. Uh, is Loeb Enterprises— is that— I think they're really legit. They've created a couple of really interesting things.

Yeah, I mean, it's very legit and it's one of those things where you go in and he's like, "Oh, we've got this company and this company and this company, and one of them sends direct mail wine and the other one does receipts and you take a photo of your receipt and send it." And you're kind of going like, I don't know what the BS is versus what the big businesses are. They throw a lot of spaghetti against the wall and they incubate a lot of businesses. And like you said, they have an amazing track record of making some of these big businesses But, uh, but yeah, he's, he's a total character.

Yes, that guy is crazy interesting. I'm so happy I got to talk to that guy. Um, I, I have another meeting with those folks, um, um, and I'm looking forward to talking to him. And if I host that dinner, or even if I get to attend the dinner and he lets me invite people, I'm gonna invite you because, um, inviting you and a few other people, that's like, maybe that's like how I'm gonna look legit to this person. Um, super fascinating. Catching feels when I let the mic go. Uh-huh. Yeah, yeah, yeah. Feel like I can rule the world. I can rule the world. Yeah, yeah, yeah. Like I'm on top of the world.