Why Success Makes You Lonely (And How Andrew Wilkinson Avoids It)

I sat down with Andrew Wilkinson, co-founder of Tiny, a holding company often called the Berkshire Hathaway of the internet. Now, I've known Andrew for well over a decade, and I've listened to every interview he's done, and he's usually asked things like his thoughts on investing, how does he run a portfolio of companies, how does he manage his wealth? People rarely ask about how he navigates relationships. I think that is the most fascinating thing about him and one of the biggest reasons for his success. Now I featured Andrew in my book community made but we only scratched the surface. So I flew halfway across the country to sit down with him and ladies and gentlemen he did not disappoint. That discussion was wide-ranging, but we talk about how to build a network from scratch, how to use cold outreach to open almost any door, and the one question Andrew asks before he trusts anyone, especially when the stakes are high. And finally, the hidden cost of money and status that nobody warns you about, and most importantly, what to do about it. What I love most about Andrew, both in this discussion and in reading his book, Never Enough, is his honesty. It's refreshing and rare, especially at the highest levels of success. So enjoy. If you could take me back to the Andrew of 2006, 2007, 2008, my biggest question is, were you relationally focused at the time? Like did you understand that relationships were going to be the key to kind of bridge the gap from where you were to where you want to go, or is that something you stumbled upon? So, um, first of all, so fun to be chatting with you and I wish we got a chance to sit down more. So, I'm so excited to do this and that we get to actually record it and share it with other people. Um, I remember I did an event a couple years ago and I'd been to I think I've been to one of your mastermind talks events and I invited you to the event that I was doing, my interesting people conference three years ago and you complimented me on my event and I was just like, "Oh my god, we've done it. This is high praise." So, I'm excited that you're now attending the event and uh and that you see that because I that was like really really crazy high praise for me. I appreciate that. Um, so you know, in 2004, 2005, I was like a journalism school dropout. I kind of done some entrepreneurial stuff when I was a teenager. I'd started like a tech news website out of my bedroom, but I never really made the connection that I like business. And so when I dropped out of university, I got a job as a barista literally just cuz I like coffee and I like talking to people. And I actually love being a barista. you know, being a bista for someone like me or even for you is kind of the best job ever. You just chat with people all day. Um, I did a personality test last year and it said on the extraversion scale, I'm like 96th percentile. So, for me, a good day is a day filled with people, especially random people who I can learn from. And I would just learn from all the people that would come in and chat with them. And I think that if I didn't have to take the bus and I didn't have to wake up at 5 in the morning and I didn't get paid $6 an hour, there's a world where I'm still working in a coffee shop or owning a coffee shop or something. And I think my whole entrepreneurial journey has just been realizing the thing I love is people and finding a really profitable high leverage way to use that skill set. So for me um I don't think I consciously knew that. I just went, "Oh, I like talking to people and I seem to be good at that." And so whether it was selling a website or buying a business or doing a podcast, I that's kind of my my happy place. Um so I I don't think like you know I I would read these books like um Keith Fazi has that book Never Eat Alone or whatever and like there's the whole kind of tactical strategy. I was never like that. I would just go what am I really interested in and how do I meet the most interesting people in that world? Um, and most of that was through attending in the early days, attending events, really fishing where the fish are, where do the interesting people hang out. I'm going to put myself there even though I don't deserve to be there. Uh, and I'm just going to ask a lot of questions. I would never talk about myself. I just ask people questions. And an interesting thing happens, as you know, when you do that, you just compound. Your network builds and builds and builds and suddenly you have friends in every city in the world. And before you know it, people go, "Oh, you should talk to Andrew or you should meet Andrew." And so now, 20 years later, I don't really go to events or anything. I just get amazing people introduced to me all the time. Um, and if I'm interested in a topic, whether it's movies or music or business or whatever it is, I just cold email or find someone in common with the person I want to meet and I try and basically scoop all the interesting stuff out of their brain and learn from them. So, did you find yourself when you were going to those events having to go to a lot of those big cities? Uh, or were you doing most of your kind of focus kind of locally? >> I didn't know anybody locally. I didn't have any entrepreneur friends until >> probably 2012 maybe when I started meeting other local entrepreneurs through EO. I think you're a EO member as well. Um, and so what I found was, um, I could meet whoever I wanted to meet by just traveling to other cities and going to conferences and that sort of thing. But I also realized that, um, people in big cities are incredibly ambitious. And sometimes they're so ambitious to the point where um, their life isn't that interesting, right? They're like a shark. They have to keep swimming forward. They aren't self-examining. they're just ruthlessly trying to make money or build a business. And so what happened for me is over time I realized that those people are really interesting to visit. It's like going to the zoo and seeing the tiger in the cage. I don't really want to get in the tiger cage. Um in Victoria I ended up building this network of other entrepreneurs and friends and some of them had really impressive businesses and some of them ran small businesses that were equally impressive to me. And I realized that those people had just as much depth or if not more than the, you know, uber billionaire types. And so over time, I would say over the last 20 years, I really have gravitated more and more and more to just really deep relationships with people in Victoria. Um, and I don't what I like about that too is I don't do business in Victoria. So it's pure like there's no money involved in my relationships as much in Victoria. So you had that almost that discernment of not writing people off early. >> Never. I I you could I can be fascinated by somebody who runs a dry cleaner. Like I I don't care what they do. I I will find the thing that is interesting about someone and whatever they're passionate about and I will get them talking about that and I find that interesting. That's interesting to me because for me when I started out I was deeply influenced by uh Tony Robbins and like Jim Ran's philosophy of you're the average of the five people you spend the most time with. So naturally you want to surround yourself with people who are more successful, in better shape, whatever the case may be. Um and I did that for many years. Not like tossing away relationships per se, but just constantly focused on like trying to forge relationships with people um that um yeah had what I was aspiring to have. And it created that gap. One of the beautiful things is when you spend your time with all those people, uh, it creates this gap that you don't feel like you're enough. So, you're like trying to like catch up to them all the time. So, it was dirty fuel, but it was fuel nonetheless. That served me for a point in time. But then the challenge is is when you're always measuring up, inevitably you feel like crap. Um, and it took me probably 8 n years to actually start to have more of an appreciation for the problem with those people is most of them have a personality disorder or a deep trauma that's caused a personality disorder. And I don't hold it against those people. I think if you learn about the context of their life and where they came from, it almost is always really rough. And it makes a lot of sense why they've built this narcissistic shield or or why they're a sociopath or whatever it is. Um, and I'm not saying all successful people are like that, but I'd say most people that are still obsessed with money and growth and all that stuff are broken in some fundamental way. Um, and so for me, um, I don't enjoy hanging out with those people as much because they usually, while they're really interesting in a niche, it's it's like a being a professional tennis player, right? Uh, if you're a professional tennis player, your entire life has been dedicated to hitting the ball in the right way. And usually that's to the detriment of your social life, your friends, your family, all these other parts, your hobbies, all these other parts of life that are really important and interesting. And I just find those people are often very unbalanced. And so I've learned a lot from them. And I enjoy there's many, many people that I think are wonderful that are uber successful, but I often find that the people that are able to actually connect on an emotional level, they're not those people. I just think it's it's uh incredibly impressive that you had that level of maturity. One could say, >> "Well, >> I didn't. I thought I was just like you. I mean, I wrote a book about it. I I literally I thought everyone's everyone's having a better life than me. Uh when you get rich, like life becomes amazing. It's like entourage. You're suddenly like Vinnie Chase and you have an amazing life and and everything's great." And I would say money is actually uh and success is antithetical to having close friends and community and all those things because you other yourself. Yeah. Well, there was I don't know where I caught it from. I think it was maybe your interview with Sam Parr uh where you shared about this whole idea of like renting a yacht and how like expensive it is. Do you want to share the story? Do you know where I'm going with this? Okay. So, so basically, um, I'd say I'd say until about 2020, um, you know, I was making a lot of a lot of money. Um, but I was mostly just investing it all and living, you know, pretty normal. I lived in a middle-ass neighborhood. I had a relatively normal house. I had a nice car, but that was it. And so, I hadn't really otherred myself, uh, which was nice. So, I remember like having this moment where I was like, okay, I'm making all this money. What am I doing with it? It's like I've got this warehouse full of of credits that are supposed to transfer into an amazing life. How do I take those credits and do something cool with it? And so I started, you know, trying to go on crazy expensive vacations and chartered a yacht with some friends and all all these things you're supposed to do, you know, buy a wine collection, all the things you're supposed to do when you're rich. And I found the yacht thing especially was just like bizarre because it's like first of all, you're taking your friends on this boat, which is immediately kind of weird, right? If they're not from that world, they're like, "What is this place?" Right? What what is this? We're on this crazy yacht and we have people serving us all over the place. Um and and it costs a fortune and it's just weird. And so you immediately are just different from all your friends and there's this weird status thing which I don't like. And then I also found myself going, "Okay, so we're in the middle of the ocean away from everyone. Why would I want that? Why wouldn't I want to be in a hotel with random people at the bar and restaurants to go to and and f, you know, new friends to make?" And so I just found it like kind of isolating. And I realized most of the the rich people things isolate you. So it's like you take a private jet, you don't get to sit next to the random person uh in the aisle row and strike up a conversation. um you know, you you use uh you have someone else shop for you or cook for you. You don't go to a restaurant and meet people or you don't go to the grocery store and bump into others. And so what I found was those things they they make other people uncomfortable because you're rubbing, you know, your money in in their face or they feel like, you know, otherred. Um and then also you're just wasting a lot of money for something that doesn't necessarily make, at least for me, make me feel good uh or connect with others. So for me, I found like there's very few things that are expensive that are actually worth it and make your life better. >> There's the obviously the dark side of what money can do to relationships. Um, specifically when you have like long-standing friendships and what does that look like when it comes to you potentially supporting them, uh, maybe lending money, uh, and that kind of stuff. Are those some of those are those some of the things that you've had to explore, create rules around uh and that kind of stuff? >> Yeah, I mean I think um when I was growing up um the whole reason I think I was obsessed with making money was because when I was a kid uh my parents would always fight about money. It was always the stress and if we went on you know we went on a vacation or we did anything if it was expensive my parents are just stressed out and miserable and at each other. And so when I was a kid I decided I'm going to save my family. I'm going to make so much money that no one can ever fight again and I'm going to solve all these problems. And in doing so, it actually caused more problems in my family. It caused, you know, there's strange resentments that pop up. There's gifting people money. There's expectation. Um there's again this othering, this idea of othering yourself. you know, in a family, like if everyone is not equal, it can kind of create this weird thing where even with your siblings, it's like, oh, well, you're you're the patriarch. You got to take care of everyone. And I find that um >> Are you the oldest in your family? >> I'm the oldest. I've met a lot of rich people. And I would say a lot of people who don't come from money think, "Okay, I'm going to I'm going to save my family. I'm going to make sure my kids grow up wanting for nothing, and I'm going to make sure they're taken care of." And often it backfires. um you know, if you don't give them the money, they resent you for that. If you give them the money, then you ruin them and they don't have any ambition. And I'd say that a lot of really wealthy kids are in a very difficult position. Um and it's not something that I envy. I I don't know many people that are second or third generation where it's worked out smoothly. It's not the worst thing. Obviously, it's a great privilege. Um but I wouldn't say it creates family harmony. When you look at your passing, one could say, I believe I read somewhere that the the die with zero philosophy at least at least at this point in time in your life speaks to you. Is that still the case? What I would say is not um I know the whole I read the Bill Perkins book and I think that um I don't know that I agree with him that you should you know book a 737 and fly a hundred of your friends around because I still think that is othering. I still think that's like your big daddy and you're taking care of all your friends. Uh and I've found that really uncomfortable. Like I now if I'm hanging out with people um that have less money, I I'm I just go where do you guys want to stay and I make sure everyone pays for their own thing because I don't want it to be some weird dynamic where I'm paying for everyone and everyone thinks they have to be nice to me or something. Um but in terms of the money, I mean, I'm I've communicated to the kids that, you know, it's all being given away. They'll be taken care of, but I think it'll be like social security plus. A friend of mine has a really interesting um approach. He he's a multi-billionaire, but when his kids were young, he basically said, um, I've given away all the money into a foundation. >> Yeah. >> I've retained a small amount for um for him and his wife where they get they get to live really nicely. They get an income from it. And the moment they die, it goes to the foundation, and then there's a small amount of money, small, it's a large amount of money, but not billions. It's $10 million per kid, and it goes to each kid when they're 35. and they can borrow against it to start a business or go to school or pursue projects, but that's it. And the interesting thing is he doesn't decide whether or not they get the money to start the business. Uh he got a third party to do that. So the idea is basically he's washed his hands of the money. It's they're not a dynastic family. The money will go back to society. And I I I really admire that. Um, I still haven't figured out all the mechanics because my kids are so little, but um, I think it's just such a deeply corrosive thing to do to your kids. >> Is there, you've mentioned othering a few times now. Is there a specific instance without sharing anything too vulnerable that really stands out when it became very apparent that you're almost treated differently? >> I was reading uh, Lena Dunham. Do you know who Lena Dunham is? She wrote a really amazing memoir recently and she talked about this phenomenon of her phone stop. The more successful she got, the fewer phone calls and invites she got. And she said that she would go out for dinner with her friends and they would say, "Well, we didn't invite you because, you know, we thought you you're too busy or um she'd talk about a problem. You know, she has these really fancy problems, right?" So, you try and share a problem and people kind of make they roll their eyes or must be nice or those sorts of things. And so um I really related to that phenomenon. I noticed that the more you know the more the more I had a a big house and you know the more you know I wrote my book and I kind of came out got more press I noticed that people stopped inviting me to things and when I thought about it I went it makes sense because when I would meet really impressive business people as and I'm sure you've had this phenomenon as well. I wouldn't want to invite them to my house. I'd suddenly be embarrassed of my house. my house would be tiny compared to theirs. Um, and so I just wouldn't invite them. I'd have all my friends that are at my level over and that was very comfortable. And I I really I've really realized this over the last couple years that, you know, I do not want that. Like imagine if I'd rolled in here and I was wearing a $100,000 gold watch and I'm decked out in like designer clothes or something. I'm communicating something to you whether I intend to or not, right? I'm othering myself in the room. And I think that same phenomenon plays out with cars and houses and how you talk about your problems. And this is why so many rich people become totally disconnected from reality because they end up not being able to talk to to their their normal friends about it. And so they have to hang out with the people at the country club who they can talk about which private jet to fly on and how hard it is to manage a fleet of nannies or whatever whatever problem they have. And then they just become more and more disconnected from reality. So, I've really fought to not do that and not become like that. >> I have a little bit of a vulnerable emission. Um, this is probably one of my biggest growth edges in the context of relationships right now where I have friends that are getting increasingly more successful and there's there's like the scarcityminded individuals that would be like, you know, you know, putting them on a pedestal and that kind of stuff and or trying to tear them down. Uh I am obviously incredibly happy when a friend is becomes more successful in those kind of things. However, I noticed a natural distancing between me and them. Uh and this has happened consistently and the narrative for me is they have a lot going on and I want to be respectful of their time and all that kind of stuff. Uh and I know it puts tension on on my relationships. I'm thinking you you know uh Shep Chef Gordon in and Maui. Uh that's one of those relationships that he as time has gone on and more I know more about the intricacies of his life every time he reaches out of like hey you should come over you know stay with us for a few days I always brush it off. Um so to just hear the opposite side of it you sharing that like your book came out and like suddenly like people aren't calling or or inviting you to things as much uh is almost like a hard pill to swallow. Well, it's you're getting invited, but you're not getting invited to what you want. What I want is I want to go over to my best friend's house for a home-cooked meal, and I want to joke around, but instead, I get invited to some fancy business conference or some elite dinner. And that's cool to get invited to, don't get me wrong. There's like the feeling of like, you know, I was a nerd in high school. Now I'm at the cool kids table. There there's that. But I really miss having the that. And I do have that with the way that I've we'll talk about this later, but like I have worked really hard to build community that is not status-based. And that's where I get to have those friendships. But it was really intentional. There's years where I was kind of going like, why am I not is everyone hanging out without me? What's going on? >> Yeah. When you mentioned of like if you're going on a trip with friends, you my understanding from what you said is you tell them you pick the place, whatever it is, and I'm I'm down for it. Is that fair? Well, I learned the lesson cuz so because I I was the kid at school where I'd say, "Hey, can I bum 10 bucks? I want to buy a Coke from the vending machine cuz I'm always broke." And so when I started making money, I would take all my friends out for steak dinner. I'd buy drinks, whatever. There's two reactions. Like when when the bill comes, let's say I'm on a double day with a friend, the bill comes. If I don't pay, well, I'm rich. I should pay. I'm an right? If I do pay, then I'm like I'm like aling the guy, right? I'm saying you can't you can't afford it or something, right? And so you're in this weird awkward situation. And so, you know, I'd be very generous and and do that. And again, distances and then I would even go on trips with close friends and I'd say private jet, fancy hotel, I'm covering everything. And I noticed that it just shifts the dynamic in subtle ways and people feel uncomfortable. And so I just don't I don't enjoy that. >> Yeah, it's tough. Another friend of mine had a an exit uh of $200 million and he's super he's a beautiful man. super humble. He still lives in the same two-bedroom apartment that he rents uh that he had well prior to his big exit. Uh because for him like the the social disparity of just very similar uh experiences to what you are navigating and for him one of the areas of tension was you know he he wanted to go on trips with his friends um and was trying to figure out how to kind of navigate that and the only solution he was able to get to was um he go to a friend and say hey you plan the trip I'll pay for the trip uh and that worked for them but I can still see that creates some of that uh tension. There's a friend of mine who he took his business public and he made I don't know 70 $80 million or something overnight. So went from having 500k in the bank to 80 million. And he lived in a really nice uh neighborhood. He had great friends. Culdeac. All the kids played together. His whole social network was, you know, normal people, teachers and doctors and lawyers and that kind of stuff. And um my advice to him is do not. He was he was willing to buy a new Porsche. I said don't do anything. Like don't if you're going to do it like buy the Porsche, keep it in a garage secretly and then drive it on the weekend. Like do not do that because the moment that Porsche rolls in must be nice, you know? And it's it's a natural tendency like I I'm the kind of person where like you when my friends do well I feel very positively and I go I can learn from what they did and I can reverse engineer it and do the same if I want to and I can just be happy for them because it doesn't take away from me. But I do think that um if I don't know someone very well I will have a lot of negative correlation with that. So, let's say that um there's there's number there's a number of people in town where they drive a Ferrari around and there's one guy in particular, he drove a red Ferrari around and I just thought he was the biggest in the world. I never met him, never talked to him. I just see him in his Ferrari with, you know, his hair going and and I'm like, "Fuck that guy. I hope he, you know, something bad happens to him." Well, I met him 10 years later. He's the nicest guy ever. And so I understand that urge to not to to want to see the successful people fall in the mud, the tall poppy syndrome as they call it in Australia, right? To cut down the tallest blade of grass. Um, and it's a sad reality of humanity. So when it comes to stuff like uh this hasn't happened to me, well maybe on a very very small scale, but like friends pitching you ideas and again the idea of loaning money or whatever the case may be. Have you created rules around that? um where it's like I have a blanket rule. I do not invest in friends businesses or something like that. >> So I I would say um if a friend uh if a friend's starting a business by default if they're a close friend and I think it's they're you know a good entrepreneur I will just put a small amount in not like a you know life-changing amount and I'll make sure I'm not a big investor in the business ideally. Um, and um, generally I will, if I'm co-investing with someone, I'll make sure that we both are coming from the same place because a great way to lose a friend is to, you know, they say, "Hey, I'm going to start the business. I'll put in all the sweat equity, you put in the cash, and then they do it and and you're misaligned because to you, like, let's say I put in 50 grand, right?" For me, I'm like, "Okay, no big deal. If it fails, that's fine. And I'm not going to put much energy into it." to them. If that business fails, maybe that's catastrophic. And when you get those misalignments, that can be really bad because you can have horrible resentment. Where it has worked for me is there's a business, we're both investing an equal amount of money into it. We're both playing the same role and if it fails, it's fine. That I can keep friends, but whenever there's a misalignment like that, it can cause really big problems. >> There's obviously benefits as well to having more resources. Is there something that you've done to that has helped kind of bring relationships closer? >> Yeah, I mean I would say that um I do I have an amazing lake house where I invite friends up to all the time and there's something about hey come over to my h come stay at my house. There's no awkwardness to that really because you know I'm staying there anyway. It doesn't cost me anything to have more people and I'll do like weekends with close friends there and that kind of stuff and that has been wonderful. Um, most things I've spent money on have not um not brought me closer together with others. What has brought me closer is facilitating deep connection in a way that is equal to everybody. So, for example, I do like forum groups like EO. I've spun out. I do my own forums. I run five forums. So, I do one a week basically or two sometimes. >> Five forums active. So, I love I love forum and and you know, in those forums, we all chip in and we all rent the room. Um, and there's a format and we have really amazing like some of my closest friends are in my forums. Um, and I've been doing those for 20 years. Forum, um, pickle ball, um, I do entrepreneurs lunch club. So, once a month we invite all entrepreneurs from around the city, big and small, to come and just have lunch in a kind of facilitated way. Um, and then what else do I do? And then I do interesting people obviously. Um, but all those things, you know, it's it's not like I'm saying like, "Hey, everyone come and have caviar and oysters or something like that." It's like, "Hey, let's just all hang out." And I'm just the host. >> Well, that's one of the things uh I got from the Nick interview uh on your your podcast uh Never Enough where he shared creating ho making hosting a habit and I love that frame and that's something you do beautifully. Uh, so you just touched on the entrepreneur lunch club. Um, can you tell us a little bit more about that and I'd love to hear some of the other habits that you have? >> Yeah, so that was really simple. It was um I rented out a restaurant. I invited um initially about 20 entrepreneurs and I I hated these network event networking events where you go and it's just small talk or dick measuring or bragging and that kind of stuff. And so we basically um I was very careful to invite people I really thought highly of and you sit down and the only rule is no small talk. And so we have prompts on the table and we start by everyone going around the room and saying wins, what's going well in your business and then people share what's a problem you could use help with from the group. And so we kind of start off with that and then um we have lunch and on the table yeah there's like five questions. So it'll be like who's your biggest cheerleader right now? um what's the most difficult problem in your life right now? Um outside of your business, what is chaotic? Um and it just ends up resulting in these really interesting deep conversations. And I Nick has this concept of a friendship funnel. And so the idea is basically like it's all the nerds love this because it's like marketing, right? It's like you have this big broad funnel, all these events where you're meeting people and then over time you're bringing them closer and closer where you go, "Oh, I really like that person. I want to build a closer relationship." So, if I like someone at ELC, I might invite them to my pickle ball group and there we're going to spend way more time together. And then I'll introduce them to a bunch of my friends. And if my friends like them, then maybe I'll um bring them into one of my forum groups or something like that. And and it's it for me it's just been this way I think in your I'm 40 now and I find in midlife with kids and stuff, you kind of need these rituals or ways of forcing yourself to be social. And for me, I have so little time to do that that I want it to be really intentional. It's funny cuz most of my socializing is forum, which is a very controlled in environment, but I end up just only hearing like fascinating things that are going on. >> Yeah. The the importance of creating almost like forcing functions uh in your life, similar to I go see a personal trainer and we work out pretty exclusively my legs because left to my own devices, I will not work out my legs. And similarly something like forum is such a powerful tool because it's on the calendar once a month or in your case your case five times a month >> and uh yeah you can't miss it. You show up it's inevitable in a space like that you're going to even if you you're reticent to talk about your problems being in a safe space where other people are sharing you'll naturally feel much more inclined to kind of uh share as well. So you have the entrepreneur lunch club you have the form groups that uh you put together. Anything else? >> I do I do an event called think week. So once we started doing it this year, but I basically invite 20 people up to my lake house and we just >> was that the AI one? >> No, it was just it was it was literally just the idea is you come, you put your phone in a box for 3 days and you just enjoy yourself at the lake and we facilitate everybody breaking into small groups and connecting so everyone gets comfortable. But it's literally just how do I how do I take all my amazing people that I know and how do I get them all to become friends? And so there's so many great friendships that have come out of that. The other event I started doing is camp dad. I, you know, I take my kids up to the lake all the time and we do activities, but when I really think about the memories that stuck with me from childhood, it's often been a trip or a unique place. And so basically, a bunch of my friends all expressed this this desire of, yeah, I want to take my kids on more trips. I want more quality time. And so, you know, before we started recording, I used the word jobs to be done. When I hear a job to be done, that doesn't have to be a business thing. It could be an emotional thing. And so, the job to be done was, how do I create core memories for my kids and a bunch of other kids and and their dads? And so, we started this thing called Camp Dad. And we all just go to a resort or an island or wherever and we just hang out. There's no programming. It's just hang out, eat good food, kids run around in a pack, everyone makes friends. And uh and that's been amazing, too. >> I'm moving to Victoria. You'd be welcome. You should. Absolutely. >> Dude, this is amazing. I had no clue. Um, even like it seems like hikes and that kind of stuff. >> Hike club. Yeah. >> Things that you're integrating. >> I'm I'm like sure I'm forgetting because there's more. >> The the thing that's coming up for me is this is a tremendous amount of like time and energy. I guess you have support to like put them on and that kind of stuff, but you're initiating all this stuff, which I think is I mean taking ownership of like your relationships is a is a huge factor. Well, it's it's a business in and of itself because, you know, I have ADHD. I'm not good at details. And so, I fortunately, it started out with just my assistant managing it all. And then now we actually have a team that runs the events. And so, I can basically say like, "Hey, here's what I want to do. Here's who I want to come." And like, I'll host it or Nick will host it or whoever or Ben will do it sometimes, but um other than that, we show up and we just enjoy ourselves. And don't get me wrong, there's lots of little details that we end up thinking through, but it means that um I never want to I remember there's this amazing book called The Goal. Have you read it? >> No. >> Basically, the idea is >> it. really good and it's it's a quick read, but the idea is um it's a fac it's about a factory and in the factory the whole idea of the of the whole thing is how do you not limit throughput which is sounds kind of nerdy but think of it as like if you're building a plumbing system and you got a lot of water you want to flow through it don't have a tiny pipe have a big fat pipe that can tolerate a lot and so for me I just want to put as much stuff into this machine all my ideas for socializing and then have the ability to do anything without it causing my life to become miserable. And so I've delegated a lot when it comes to this and my businesses and everything else where I can just have raw ideas and relationships. And that's really my thing. So if you think about tiny even, it's like I storytell, I set like highle strategy. Um, and I just build relationships. That's it. Like literally that's it. Whereas in old me 10 years ago, it'd be like, oh, I'm also running marketing. I'm also doing sales. I'm also doing admin and HR and all sorts of other stuff. And I've realized like my zone of genius, I hate that term, but it's like the thing I'm good at are those three things. And so I just apply that to any anything I'm doing. >> And given the impulsivities that can come with like ADHD, do you find yourself stretched too thin? >> Are you an ADHD guy, by the way? >> Uh yes. And actually, you know what? I referenced you uh in the context of ADHD because we had an event two years ago with a gentleman named Dr. Ned Hollowell. Oh, amazing. >> Yeah. Who's like one of the OGs in the space? >> One of two basically. >> Yeah, exactly. And uh I was going to interview him because obviously facilitating a room full of entrepreneurs, majority of people struggle with it and may not be aware of it. Misdiagnosed and a lot of adults and and women specifically uh >> it's one in three entrepreneurs. >> Yeah. So it's it's it's uh so my brother was diagnosed when we were young. I was not. Uh but I had all the hallmarks and I came up with all the coping mechanisms to like to uh to make do one could say because I always said there's only two places for me either be in business or prison. There's nothing in between. Uh and it's even like I've done a bunch of coaching things in prison meeting inmates and that kind of stuff. And I I while I'm talking to them I'm like you are just like me just the wrong environment. Uh but I share this because within two minutes of meeting Ned he's like you know you have ADHD. Like I know, but I was scared of uh medication. >> Uh I grew up unfortunately a lot of uh addiction in my family and prescription addiction and alcohol addiction, all this kind of stuff. Um so any semblance of like a stimulant or or that kind of stuff I've I've kept far away. >> You still are unmedicated. >> So funny story. Uh so when Ned told me, "You have ADHD," I'm like, "I know." And he made me feel more comfortable with the idea of medication. So I came back, I got assessed, I was nine out of nine. Uh, and then I took a medication called Viviance, which is >> I'm on it right now. >> Well, so the thing thing was they assessed me. They're like, okay, you're nine out of nine ADHD. That's clear. You're also you also have severe generalized anxiety. >> And I was like, I know about the anxiety. And they're like, well, we can we can do something for that. And I said, don't worry about it. The reason I'm anxious is because I can't get work done. So, if I can get work done, then I won't be anxious. Turns out that wasn't the case. So, I started taking Viviance, which has anamines in it. And ultimately, my nervous system was already at a low simmer and the Viveance just threw me into a panic attack. Uh, >> I have I had the exact same experience. And I also have crippling anxiety, but my anxiety was never um it was never normal. Like I describe it to the doctor as like an itch. >> Yeah, >> it's like an itch. And I feel like I'm always forgetting something. I'm always letting someone down and someone's going to be mad. I can't relax otherwise something bad will happen. Um, and so I I had this exact same experience. I took the Viveance. revved me up and we'll talk after this because there's lots of I I've cracked it. >> Yeah. Um >> well, I was reading through your newsletters and I stumbled across a piece where you talked about um having success uh in that in that realm. So, >> I mean, and it's a gift and a challenge, right? It makes you amazing at so many things. And it also I I mean for me, I would rather let's say they discovered that um the medication shortened your life by 10 years, I'd still take it. like I'm that much happier because now with the right treatment, the anxietyy's gone. And when I think about what caused me to be so maniacal and miserable growing my business, it was the ADHD and the anxiety. >> Well, I appreciate that. Um because hearing friends initially who were taking ADHD medication and seeing success gave me almost like the permission to like lean into it. Uh, and it was reading your newsletter this morning about anxiety medication that I was like >> maybe I'll explore that. So, I really I really really appreciate that. One thing I I have to touch on cuz I think you are super unique in this sense >> and it's something I wish I did more of >> is this idea of cold outreach. Sounds like it's been something that you've been leveraging for a long long time if I'm not mistaken. Uh, and it's opened some incredible doors. So, can you take me back to maybe one of your first cold outreaches that you can remember um where you got a yes on the back end of that and what happened? >> So, um when I was 9 years old, I I was a huge nerd. I was obsessed with Apple. I was obsessed with Steve Jobs and I read uh I read this huge biography of Steve Jobs and I kept watching this movie called Pirates of Silicon Valley. Have you ever seen it? It's like a terrible made for TV movie with Noah Wy. Um, but I' I'd watch it over and over and over again. And I became totally obsessed with Steve Jobs. And I wrote this email, a letter. I was gonna send the letter, this letter to Steve Jobs saying like, I want to be like you. You know, all all I want to run Apple someday, all this stuff. And so I I ended up going, well, he must have an email address. And so I I guessed I was like, okay, s jobs at Apple, Steve Jobs at Apple. I typed in all the different ones and I sent this letter to every single address, maybe 10 different addresses. 30 minutes later, I get an email back from S Jobs and Apple and it just says, "Follow your own course, Steve." And I was like, "Oh my god." Like, "This is crazy." Like, I'm a 9-year-old boy and I was able to get in direct contact with the most powerful CEO in the world. And for me, that was like this crazy thing. I got lucky. The first cold email I ever sent worked. And of all the cold emails to work, like that's crazy, right? And so, um, I got in the habit of even when I was in journalism school, um, I would reach out to like famous journalists in Toronto and usually I would say, um, hey, like I'm good with websites. Can I help you with your website or is there or can I just take you out for coffee or whatever it is? And if I'd sent 20, I would probably get one back, but I'd still get one back with someone that I would never otherwise meet. Um, and so when I started my business, I just got in the habit of doing that. And a lot of the way that we grew Metalab in the early days was I would see a cool company like a startup in Silicon Valley and I would send a oneline email to the founder. I'd say we should work together. That's it. And they're so cocky and random that even if they thought I was an they'd be like, "Who are you? Like what what's your deal?" And then often that would lead to a coffee. Um and so I've done that with I mean multiple billionaires um you know all sorts of people. And now it's become easier as I can reference like let's say I reach out to like um the other day I reached out to um a very famous actress that I wanted to come to the interesting people event and I just said I'm the owner of letter boxed. People know letter box now and so immediately I got a response um and she wasn't able to come but uh still got a response and you you realize like everyone has an email and you can find the email quite easily. Um, and so what I do is I'll basically go, um, what's their company domain? What's their family office or their production company or whatever, and then I'll use a tool called Hunter, hunter.io. And you just type in the name and the domain, and I'd say like 60% of the time you get a hit. And people don't always respond, but I've had a lot of really interesting meetings as a result. >> Can you share the Dan Gilbert story? >> Yeah. So, um I was reading the New York Times and I was thinking a lot about philanthropy um in Victoria especially and I was starting to do some stuff locally. Um and one of my biggest critiques of rich people is that they don't do very interesting things with their money. So, they'll make a billion dollars. They start what's called a family office, which is like a douchy rich person term for a holding company for their money. and they'll usually invest it in stocks and bonds and real estate and you know save it for their kids. And I read this article about Dan Gilbert and basically um he owns Rocket Mortgage which is like the biggest mortgage originator in the states. He's a multi-billionaire and in 2008 when Detroit almost went into bankruptcy or did go into bankruptcy, he basically said, "I'm saving Detroit." And so he's done all sorts of amazing things like he he took um there's a ton of people who are very poor and they had big tax payments to the city. He paid them all. He bought downtown uh all the bunch of skyscrapers, refurbished them, was just doing all this amazing stuff. Um and I really admired that. And so I just sent him a cold email. 30 minutes later, this at 1:00 a.m. 30 minutes later, he's randomly up at like 4 in the morning. And he literally just goes, "Yeah, come to Detroit." And CC's his assistant. And I ended up getting an amazing tour of Detroit. Dan spent 3 hours with me and it was just a reminder of like, yeah, there's there's always someone on the other end of of an email. And most powerful people, they don't delegate their email. They usually check it. >> Do you remember how you position that email? >> I think I said, um, hey, you know, here's here's some of the things I'm doing. And I I if I'm going to email someone, I usually figure out, um, what are they passionate about and interested in. I knew he was interested in investing in tech and startups. So, I mentioned some of the businesses I had invested in that we I think he had mutual interest in. And then I also talked about some of the work I was doing in Victoria. And uh I find like when someone emails me um the biggest mistake is they write like a big long email. And so I just was really to the point and I was really again going back to that like be confident in what you're saying and act. It's like it's like asking out a girl and saying like, "Hey, um I'm a really good successful guy. Um please can we please I'll go out with you anytime." You know, it's like that's not going to work. You have to walk up and be like, "Hey, you're really beautiful." And like we both like soccer. Can we go out for a drink or something? And so I think it's the same with cold email. It's got to be very direct. It has to go straight to the point of the commonality or how you might be able to help them or their interest. Um and and it has to be super short cuz like I get I get emails every day that are like 10 paragraphs. I just I archive them. >> Yeah. >> I think that's the mistake. I've made that mistake before sending cold emails that were way too long because then it I think unconsciously gives off the vibe that their response then needs to be thorough. Um and I don't know your stance on in that initial email. Well, I know it's context dependent, but like how likely are you to be transparent or like show that humility? Um like do you do you say, "Hey, listen. I know you're super busy and super successful." Or you almost treat them like, "Hey, we're I'm just a guy. You're just a guy." And they they are the biggest mistake with successful people is acting differential and weird, right? Um you know, I think people like to be respected. They like to know that you researched them and you know maybe you read their book or you you read an article about them or you know their business. Um but but I think being differential and creating a weird dynamic where you're you know there to kiss your their feet or something like that it doesn't go well. >> Damn it. I'm learning so much. I uh using claude a lot to like reflect back patterns I have in my day-to-day life and one of them is hedging. The only the only thing I will say that's interesting is like a guy emailed me, a local entrepreneur emailed me and he said, um, "Hey, um, you know, I run an HRA company. I know you're interested in local businesses," which I am. I I invest in lots of local businesses. And so, okay, Tick, um, maybe I invest in his business or help him in some way. He said, um, I read your book and here's what resonated. Okay, the guy's done his homework. And then he goes, um, and I know you own some buildings and and you have houses. I could help you with HVAC stuff if there's ever anything. And I just happened I probably would have said yes regardless, but I also was like, "Oh my god, I need HVAC in my basement. I need to install it." And I've been dealing with this other company and they've been bad. And so it was like the next day I'm like, "Come over. Let's hang out." Um, and that there there are rare moments where it's maybe a little bit transactional, but I'd say usually it's not likely that someone's going to offer me something that is like quid proquo or something. It's uh it's I can't stress the doors it's opened for me to do cold outreach because sometimes you'll forget and then you look at like it's always a fascinating exercise to look back of what was the first interaction you had with that person. Uh and to realize it was based off a cold random email like hey I saw you a magazine. I thought you're fascinating. Know you're working on a book. Maybe I can support you with some things I learned or whatever the case may be. Uh and how those relationships compound over time into some extraordinary things. And uh I think for for people, especially if they're starting out, that's there's no excuse. And like you're still doing cold outreach to this day. If you need any like validation of the power of cold outreach, you're still doing it to this day at this level of scale, success, the amount of relationships you have, that's wild. >> Another really interesting technique that um I've used is sometimes in the back like 1015 years ago, I would meet someone where I'm like I have no right to meet this person. Like I am like I am like so far down the ladder and I'd be so nervous and so I would take a beta blocker. I remember I was nervous to do a public speaking thing once and my doctor's like, "Oh, here take a beta blocker." And they've done studies with beta blockers. They basically like neutralize your cortisol, right? So you don't have the physical sensation of being anxious. And so, um, they've done studies where people are terrified of spiders or whatever it is and they'll give them a beta blocker and then they'll expose them and they get exposed and their brain goes not scary anymore if you do it a couple times. And so when I was really terrified, I would take a beta blocker before and I was like so confident like I'd be in these meetings with these super crazy billionaires even when they're skeptical of me and kind of looking at me like who the are you? I would just be like totally confident, calm, and uh I think that's there's there's some neat tools like that to help not freak out. >> Well, and the thing is is once you once you start and you get that feedback loop that it works >> totally, >> then you just continue to do it. And the hardest thing for me at this stage of my life is just creating a practice around it. So what I try to do now is like a onein one out philosophy. Like if I'm investing in a relationship, uh like an existing one, I'm deepening a relationship that's an in I'll also try to use that energy and reach out to somebody who I don't know and I usually create keep like a running list. If I hear somebody on a podcast, I find them interesting and they said something that was impactful. Um like I'll jot it down and I just keep that running list and I'll use that list to send outreaches. The hard part is I find when there's people who are like they're on a podcast or they're someone that's on TV a lot and they have a talk track and the question is do you get the real person? So like I've had meetings where I've heard a bunch of podcasts and I see them and I'm like I'm not meeting the real you, I'm getting your talk track. Um my favorite is when I meet someone like Dan Gilbert who is just like he'll say anything, right? Or Charlie Mer. These guys would just like you know they'd make crazy comments about things that it's like I'm not supposed to know that. That's that's amazing. like I'm learning so much. You're like uh you know these other guys are 12 bar blues, you're jazz, you'll go anywhere. The other thing I've experienced too though is >> um I remember there was this very you know very famous um guy in finance who I had watched all his his YouTube videos and thought he was really interesting and I saw that he was speaking at a conference that I was going to go to and so I did. The mistake is I emailed him and I said I will meet you anywhere anytime. I will take the taxi back from the airport and so he goes yeah fine. you know, come in the the taxi back or come in my limo to the to my plane. And I get in the car and he's like, "So, what do you want?" Like total 180, right? Like totally different kind of personality than what's on screen. And I'm kind of talking and talking about myself and trying to tell my story. And he's just on his phone. He's totally distracted. And then as we go, he's like, "Do you want me to drop you off at the commercial terminal?" And I'm like, "Oh, no. My plane my plane's over here, too." And he's like, "Oh." and he's all of a sudden nice and I was like, "Fuck that." Like, "Fuck that guy." Right? Like I I hate when people treat you differently based on status and and that stuff. And like that's one thing like again like I don't care if I'm meeting a local dry cleaner or a random teacher or a billionaire. Like I'm just going to treat them the same cuz like I hate those experiences. I think it's horrible. >> Yeah. And that's uh I mean there's that rule of thumb of paying attention to how somebody treats a server or that kind of stuff which obviously tells a tremendous amount about uh >> well you said in the beginning right it's like money magnifies. >> Yeah. Yeah. Well and this is actually one of the the most beautiful gifts I ever got from uh Shep Gordon. So he wrote a book called They Call Me Super Mench and Mike Myers did a >> amazing documentary. >> Yeah. And I never had the desire to ever like meet a celebrity, but what happened was two or three friends of mine saw the documentary and they're like, "Hey, you have to watch this." Uh, and after a couple of nudges, I ended up watching it. And within a few minutes, I was like, "If I ever have the opportunity to be just in this guy's proximity and see how he navigates the world, um, I would love that. Think about what you can tell about him, right? So, he lives in a normal house. He's not surrounded by a cabal of terrified servants. He's not in a super yacht." Maybe maybe he goes and I'm sure he does fancy things, but he lives his life in a normal way. And I think you can tell so much about someone based on when you go to their house, what is the vibe? How do how do the pe if there's people that work for them, are they terrified of them or not? Like, and I watched that movie, too, and I was like, "This is the north star." Like, that guy has it figured out. >> He and the thing is like he is what he is. Like how he's portrayed in the documentary is truly how he is. had so many opportunities just spend good quality time with him and meet random people in Maui that are like massage therapists or and they sing his praises everybody. Um they'll invite he'll and he'll host dinners at his house all the time and it'll be like Stephen Tyler from Aerosmith and like somebody who works at the food bank and then like somebody else in town um and he treats everybody the same. He actually would do this big annual fundraiser every year um to raise money for the food bank and they'd have all kinds of acts that would they Willie Nelson and all these people perform and in the leadup he would always be more excited because he always would feature some like local talent that nobody knew and had like in theory no they shouldn't be on stage. um he was so excited to put him on stage and um he just he's taught me so much about relationships at that level and that you can do it in a really kind of beautiful way. >> Yeah, he seems like an amazing guy and like there's I when Chris and I we talked about in the book, but like we went out and we tried to meet as many people that had been very very successful as possible and pretty quickly you realize Steve Jobs was right. you got to follow your own path because people um a I've seen like a lot of these people are not happy and don't have interesting lives. They're they're lonely, they're isolated, they're obsessed with money, you know, all the personality problems, all that stuff. Um or they've built a life that is suitable for them but not for you. And I'd say like there's probably two two people that I've seen that I've been like that are like um where I'd go, yeah, you know, I could see being like 75, 80 and wanting that life. And one of them is Shep and the other is my friend Tim Kerr. Did you meet Tim? No. >> Tim Kerr. Tim Kerr is a uh he's an entrepreneur. He had a family business which he sold. It was a lumber business. I met him because he him and I invested in a in the same business and he I think he's like 78 and he just spends his time on relationships. He's got he lives on an island near near here, really small island with about 20,000 people and he just invites friends. He has three houses side by side. He invites young, old, famous, not famous and he spends all his time on connecting with people. And I I look at him and I just go like that is a good life. >> And there's not many people I know a lot of people deeply. There's not that many people that I go like I trade lives with them, you know. >> Has he been to your event? >> Mhm. He was there last year. He'll be here this year. I'll make sure you guys meet. >> This is a wonderful segue. I was hoping we'd get uh a nice segue into obviously what you're building with interesting people. So you shared at the beginning that uh I complimented you on the first event I attended which was IP2 uh and it is I'm I've been in this space for a long time 14 years now. Uh in theory could attend a lot of the events out there the Teds of the world and that kind of stuff. I'm very selective of my time. This has been the only event I've gone to three years in a row, and I will continue to go as long as you'll have me. It is so rare when you find yourself in a space that is curated with care and designed with care, and it's truly palpable. So, I I definitely want to shed a spotlight on what you're doing there. We talked a lot about, you know, the the habits of hosting. Uh, and this is arguably the biggest thing that you host once a year that happens in Victoria. I'm dying to know what made you want to take this on and what has it evolved to? >> Well, first of all, that's so nice and like I said in the beginning, I'm so honored that you've continued to come and that's high praise. I can't think of someone uh someone else who runs such amazing events to compliment who would want to like the event. So, that's amazing. Um, I hate conferences. I have gone to so many conferences where, you know, if you don't do your homework and figure out who's in the room, you'll never meet them. And I feel like it rewards people who are hustly extroverts. You have these desperate moments where most of the day is uh you're in this fascinating room and you're all sitting in the dark staring at up at a a PowerPoint presentation. You might as well be watching a YouTube video or something together. And then you're out in the coffee uh area afterwards and you have this brief moment to go and try and talk to people and you're entirely on your own. There's no work to go who are these people? What do they like to talk about? And uh it's not facilitated in any way. And so um after having that experience so many times I said like I would like to try and do this myself. It started kind of randomly. Originally, the first one was just um I had I was experimenting with like Twitter subscribers and I said, "Oh, anyone who's a Twitter subscriber, let's do like a big meetup or whatever." And then the one you went to, I'm glad you didn't go to the first one because it was a bit of a mess, but it was still fun. But but we really have um centered on this idea of I there's so many people I love all over the world who I wish knew each other. And so the idea is like um it's like FedEx, you know, FedEx, they basically the way they deliver packages is planes from New Zealand and uh Europe and everywhere. They all meet at one place. I think it's in Alaska. They exchange packages and then they go back. And so the idea is how do I get all my friends into one place in a small room that's very intimate where everyone knows who everyone is and their job is actually to connect and then how do I get them to go back and become friends? Um, and to me that's probably the most satisfying thing I could possibly do. And I think a lot of events also are focused on business or a certain topic. And I'm an inch deep in a mile wide. Like I love movies, I love music, um, I love storytelling, I love comedy. There's all these worlds that I love and I have interesting friends in. And so what I really try and do is not make it like a tech bro conference. I really just want um, you know, small local entrepreneurs. I want musicians. I want actors. I want, you know, everyone in one room and no status. So, you'll notice like on the lanyards, we don't say your company name. You're just Jason. Um, and uh, and then we really just try and connect everybody. Um, so I'd say it's well, you know this, but it's like 70 or 80% talking and 20% listening. So, and most of the listening is designed to simply just shed a spotlight on who's actually in the room. So you know who you really want to connect with and you have something to talk to them about. >> I think I stole that from you. Uh one of the things I thought you did brilliantly. I don't know if it was at you did at your first the first event I attended IP2 as well, but I think you leaned into it more uh even more so at the last event was those quick like spotlights like you on stage just saying like you're fascinating for like these reasons pass on the mic then to the next person and that kind of stuff. And in an intimate room, you know, over the course of those two, three days, everybody's like have a good understanding of who's in the room, which is obviously one of the biggest challenges of an event historically is the only people you connect with are the people you seat next to, maybe at dinner, maybe you'll bump into two, three other people, and then naturally also you feel incredibly comfortable with a group of people. So, you build these like clicks, and that is where your MC Nick Gray is world class at breaking people up. Amazing. Uh, I've taken a bunch of tips from him. >> Another thing that he does that I find so interesting is I'll go to him and I'll be like, "Okay, Nick, like you know, 10 to 10:30 we're going to do this and this." And he goes, "No, no, no. Just don't worry. Just give me give me I'll have a playlist and I'm just going to riff. I'm going to choose the things that feel right in the moment." And so he'll go with the energy. And if the energy in the room, like people are starting to cough and go quiet and touch their neck, he'll be like, "Everyone stand up. Do five jumping jacks or get in groups and, you know, in order of where you live or whatever it is." And I just find he's he's like an amazing um what do they call it? Like a what's or a conductor. He's an amazing conductor. Um so I'm so lucky to get to have him. And I also love that because then I become more of an attendee. Yes. Right. I'm not totally st like I have someone who's thinking about logistics and then Nick is mostly conducting and then I'm only getting up on stage and doing stuff when I really want to. >> So that has been great. >> Yeah. He is uh he's world class at being like in the moment which to me is not how I operate. I like to have like everything like planned and if I'm doing an exercise, it's well thought out and that kind of stuff. Um, but what he's able to do is awesome. And the one thing I value about him and his style immensely, he does it in a beautiful way where he can keep things on time without hurting people's feelings. >> He's so good at that. >> I'm the worst. I'm the worst. I let people go go on for too long cuz I feel bad and that kind of stuff. And he just him and his harmonica has become, you know, a great little tool. So, um, the event I and even the contrast I'm excited to see who's going to be there this year. Um, but there was a pretty big shift, I'd say, between IP2 and IP3 because I I my experience IP2 was like if you had to pick a predominant group, it would have been tech. Uh, but again, it was, you know, a wide variety. Um, last year there was a lot more people in film and comedy and I was like I was taken back by that. I was like, this is not what I was expecting uh in the best way possible. So, how does that look like every year for you? Like, do you do you just it's whoever is you feel that's alive in you that you're like, I would just love to have this person in my life uh and love to have him at the event or do you look at specific industries and do you look at balance? >> I would say it's um whatever I'm obsessed with or interested in. So, it's like this year, okay, last year for example, a friend of mine, a really close friend of mine messaged me and he goes, "Hey, you should have this guy Jason. He's an amazing uh magician. And I was like, "Magician, you know, that can go a lot of ways. Sometimes it's great, sometimes it's not." And um I walk in on the first day um we have an opening party and then the next morning we're kind of going into this building and as I walk in my friend Caleb walks out and he looks like he's just seen a ghost and he goes, "Whoever that magician is, he's a demon. You need to burn him." and and this guy's going around and he's pulling tic tacs out of his eye and he's doing all sorts of crazy stuff and it was such an interesting thing to add to the event and and it really made me think about um jobs to be done, right? I'm big fan of jobs to be done. So, do you know about that framework? So, for anyone that doesn't, it's like the idea is you don't go to Starbucks to drink coffee. You go to Starbucks because you want to sit in the sun, you want to read the newspaper, you might want to have a quiet conversation with a friend. And if you break a business down to the jobs to be done, you can do a really good job of delivering whatever that is. And so we after IP3, we went, okay, why did this work? What were the what were the boxes that were checked in people's heads? And so it was like, I want one moment where you get tingles up your spine, right? So that could be a great song or an amazing story or something like that. I want one moment of complete shock. So Jason did some crazy tricks that people were just totally shocked by. I want someone to be in nature and feel a reverence for the natural world. Well, they get that when we go up to the lake. And I want them to do one thing they've never done before. Um, people were, you know, going tubing and doing all sorts just high moments. I want them to leave with one friend at least. Um, and and there's a bunch of other ones we came up with, but by following those, I can be like, okay, like how do we deliver on all those things by filling the room with the right people? And I mean the other thing we do is we we don't really have speakers. So people that come, there's some people who I might subsidize coming or they come for free, but even the people who are performing or speaking or talking about anything, everyone is an attendee. They're there the entire time. Um, and so it really feels like you're just in this big community of interesting people and people are just randomly getting up on stage and doing something. And there's quite a few moments where there'd be someone in the in the audience where I'm I'm going like, "Oh my god, I can't believe people aren't freaking out. This person's here, but they don't know who this person is." So like last year we had Dan Mangan, who is like an amazing singer songwriter. Um and he got up on stage and just, you know, people are crying. Every everyone's crying or or Matt Dicks gets up and tells a story and and everyone's laughing their ass off. Like those moments are to me what makes it special. And I think most conferences don't do that. >> How do you balance new members or new attendees versus returning? >> That's really hard. Um I'd say we have a really high bar like if there's somebody and it's hard because I always want to have random people come. So there there's people that they wrote me a nice message on Instagram and they're totally random and I said, "Okay, sure you can come." I usually try and keep those people to like less than 5%. And most of the people in the room um like when I look at the list, I just grin because it's like all my all my best friends and stuff, but I really uh I've struggled to keep it at 150. We've chosen like the the tribal 150 number as the number. And we've had to be pretty ruthless about cutting and um you know, not letting people in and all that kind of thing. But it's always nerve-wracking because, you know, there's always 10 or 15 random people and I don't know how they're going to be. >> Yeah. Yeah. It's uh having experience as well, I treat them as wild cards and sometimes it works out famously and sometimes you take a chance and and it doesn't. >> Well, how do you think about that? cuz like if you you you can end up in molasses a little bit where it's like if the event is the same always the same group of people that's special and people build bonds and stuff but those new people also add some friction and yeah I mean I think one of the distinctions potentially between like an MMT and interesting people is for us we do position it more as a community. Um, and for the first couple years of MMT, I was using Jack Welch's like philosophy of management and hiring where I'd knock out like the bottom two/irds every year and just only keep like the cream of the crop and that kind of stuff. Uh, and after doing that for a couple years, I realized a it created this like um culture of fear uh of like am I on a chopping block? on some of it was good because people were on their best behavior but at the same time we want to create a space where they can remove the mask and be themselves and that was kind of inhibiting that. So for us we changed to uh a model where we allow 70% of the people to come back >> uh and 30% are new people. So the 70% of people carry that culture year-over-year which is important for us. We we curate based on a set of core values. Um, so they carry that culture every year and then the the new people kind of just bring that infusion of like energy and excitement uh and that kind of stuff and that's been it's worked well. Yeah, it's worked well for us as a as as a balance. >> But I will say like if there was one or two comments about oh that you know that person rubbed me the wrong way or they made me feel small or whatever it is. It's those those people are the ones that get cut. >> Yeah. Well, to one of the things that we we instituted years ago and it's been such a just game changer. Um, I struggled a long time with figuring out like who we were going to have back at the event and all that kind of stuff and kicking people out. Um, and then I just realized like how you run a community of 150 people is exactly how you run a company of the same size. So, you keep core values at the forefront of the selection process and you coach people up or you coach the people out based on their core values or them breaking their core values. And being somebody who's a people pleaser, it depersonalizes it because by the time they sit down with me and they know something's up. I can point to a core value and be like, we both know, you know, uh, you're out for this reason. But, uh, one of the cool things we instituted maybe four or five years ago, feedback forms. We do intake forms, which are critical to designing our experience, but feedback forms as well are are critical. And two questions we added, one was, um, who are some of the members that you really hit it off with? because then you get to see the ones like pe sometimes people who are like introverted and that kind of stuff get referenced the most and you get to really see like who are like the culture carriers or really the gems of the community so you can you know do everything you can to to to keep those individuals in the community. Uh and then the other question is was there an individual that you uh had an experience with where you felt like they didn't fit the core values? Uh, and as a rule, if somebody's name comes up once, we get interested. Uh, or we take it as data. Uh, if it comes up twice, we start to get a little interested. If it comes up three times, as a rule, doesn't matter who it is, they're out. Um, and that has that self policing, uh, has worked really kind of well for us. For you guys, do you see this continuing on in this form? Um, do you have ideas like making it bigger multiple times a year? you're keeping constraints on it. >> I think it's one once a year and I think there's lots of other formats and ways to connect the community and I know you've experimented with this where it's like take a subset of those people and go do something. Like this year we were like we should do summer camp. We'll rent out a summer camp and anyone that wants to stay we'll have 50 people come and go to summer camp for a week and just put their phones away and hang out. Yeah, it's just too much logistically. And so I'm more interested in um taking like the dedicated groups that are either like something like think week would just be like people that I think are interesting and kind and inquisitive. But there's also the idea of being like okay for AI maybe I would do something or for um movies or whatever. But at this point it's so much work to do a good uh event as you know that all you can do is dilute. So I'm very very cautious to do that too much. >> You've invest a lot in community and locally and businesses and all that kind of stuff. Was there a moment in time when that became in focus or has that always been did you see yourself being in Victoria forever and you wanted to make this the best place it could possibly be? >> Yeah, I have and I realized it's really hard. It's not really um Dan Gilbert is a good example where if you go to Detroit and you say Dan's name, half the people will say he's amazing and half the people will hate him and think that he's trying to control the city. For me, I've realized I actually don't want to um I don't want to get that involved locally. What I want to do is quietly support things that I think are good um and not make a big thing out of it. And so we do some philanthropy. We invest in some local businesses. We own some restaurants. We own um the biggest news site in town, but um I don't really um I don't do it very loudly and it's to be honest, it's not like it's not my number one priority. Um you know, it's just it it feels like a good thing to do, but it mostly results in negativity. You know, it people are you go on Reddit and you know, anything any story on Reddit in the local Reddit about me, it's like people people are very negative on it. So really Yeah. like like I did a I started um I saw the local newspaper was kind of dying and so I was like, "Oh, I'm going to start my own um news news uh newsletter and um I funded, you know, I put $7 million into funding it and building it up and building this whole team and the model didn't work and so we had to let a few people go and when we fired people it was like you're what an How dare you do this?" You know, it was it was like just a bizarre experience to try and do something good and then see that you will ultimately be seen as some out of touch rich tech bro guy. Um, so it doesn't mean I wouldn't do good things. It's more I just do them more quietly now. >> Got it. That must have been hard with your love for journalism and wanting to bring the community together. I mean, I we uh I believe you know Nathan Barry, he's done that with with Boise with a newsletter there. Um, and I remember when you were leaning into that newsletter, there was like a lot of excitement in that kind of stuff. So, to know that that uh that's how things kind of landed in the end and kind of sucks. >> It it's um and it's, you know, it's it still exists and we have a lot of journalists working for us and I think we're doing a lot of great reporting. Um, it's more just like if you do anything loudly um there's always a negative, there's a shadow side to it. There's a a quote I heard that I liked which was uh whales only get harpooned when they surface. And so, you know, the more loudly you surface, you know, book, you know, making a splash or or hey, look, I'm going to go and save journalism in Victoria or do these things, um, or I'm going to fund a wing of a hospital or whatever those things are, there's always going to be a contingent of people that want to hate on you. And so, I just, it's not, it's not to say like don't do those things. It's just you don't need to surface. You don't need to brag about it and talk about it so loudly. And I think one of my biggest lessons over the last five years is everything doesn't need to be a story to be told. you know, it's like I can just do it and not tell anyone about it. >> Well, this is uh this is a topic or question I really wanted to dig on because I know we're we're wrapping up here. Um, one of your philosophies is hire smart people, pay them well, and leave them alone. Leaving them alone sticks out to me because in order to leave someone alone, you need to trust them. Uh it's funny when I wrote started writing my book community made there's a a saying I think it was from James Clear who I know is a mutual friend where he says like the book that changes you is the one you write. Um and I thought I knew a lot about relationships has been my life for the last 10 15 years in some capacity. But as I was writing this book I realized like the notion of trust wasn't even on my radar. And once I started going down those rabbit holes, I'm like, this is this is the book. It's foundational to kind of all relationships. Um, with that said, I mean, we all have a unique relationship to trust. And I'm there's almost like two different ways that people tend to operate uh with trust. Uh they're almost like their opening bid uh when they meet somebody new. Either they will give them full trust and that's their trust to lose or they give them no trust and they need to build trust over time. Um, where do you fall on that spectrum? >> I would tell um any random person on on an airplane my entire life story and all my secrets. Um, I default to that. And I think when I meet people who are the opposite, I think they usually have good reason. You know, they had a parent they couldn't trust or they had a friend they couldn't trust or something happened. And I think that um for me, it's just made my life so much bigger. when I go out for lunch with someone and you know someone says I got divorced and I instead of holding back say I went through a really tough divorce too and if they ask me questions I'll open right up and I find that finding those areas of commonality and sharing usually not always creates a lot of mutual trust because you've been vulnerable and often people are vulnerable back and so for me I've definitely gotten burned by it many times or I've been too vocal or too open about something but I'd say like 80% of the time it pays off. And so I don't want to be the type of person that worries about the 20%. And for those 20% of people, you can stop responding to their texts or you can fire them or whatever it is you need to do. Um, in terms of figuring out who to trust, um, I think that usually I can evaluate that by meeting their friends, hearing about how they've behaved in the past, testing them in small ways. is I mean there's all sorts of there's all sorts of um of ways that Chris and I will do it when we're hiring somebody. Um but for the most part you're taking a you're taking a leap of faith with with uh with any anybody. And I think you want to rule out the really bad stuff, right? So if I'm hiring a CEO, I want to make sure they haven't been involved in three subsequent frauds or something like that. I want to know that they have a um you know they have good friends and that they um they have a good reputation and some of those things. But otherwise, um, I'm really taking a trust fall and I'm while I'm leaving them alone, I'm watching carefully. So, for me, it's similar to your events. It's like if I have three or four employees make comments to me about somebody, not that they're a hard boss, but that they're being manipulative or or um treating people badly. Usually, that's an immediate um fire. Um, because we've learned we've learned the lesson of not wanting to work with brilliant jerks. they're not worth it. >> Can you think back to a time, I think we both probably have a handful, where you made a bet on somebody and it didn't work out. Um, what was some of the takeaways from that that you applied in the future when it comes to vetting people? >> So, there's this story there's a story I tell in my book about this executive who we'll call Brian. And this guy um he came in into my network as like a mentor figure. At the time I really didn't understand very much about business. Um and he seemed to have it all figured out. You know, he's sold a company before. He has an answer for everything. And he just blindly wanted to help me with my business. And over time, Chris and I started trusting him and giving him more and more stuff until eventually he was running a division of one of our businesses. And the my I remember my brother said, you know, I don't know about this guy. He's a bit of a shark. And I said, he's a shark, but he's our shark. You know, it's kind of like that idea like you want an lawyer. You don't want to you don't want to be friends with the lawyer, but maybe you want the lawyer to represent you. And so we put him into the business. Um, and I kind of left him alone and the numbers just went up up and up and up. The business grew and grew and grew and I'd hear weird little things here and there. Um, and then one day my brother said, "Um, yeah, weird thing happened. Um, we're opening a new office in Vancouver. We're having trouble with the permits." And Brian told me to bribe the city building inspector to get that done. And and I remember my blood just went cold. I was like, "What what's going on?" Like, "Who is this guy?" We started digging in and we found that this, you know, he'd been spending money like crazy. You know, spending $30,000 at hotels and having parties. he had been um uh hiring friends of his who weren't doing anything and giving them you know $50 $100,000 and ultimately he'd actually started siphoning off our clients into a new agency that he had started and so going through that experience um it was a good reminder of just like you you cannot swim with the sharks without getting bit and ultimately now um when I when I'm interviewing someone or thinking about trust trusting someone, I'm looking for their humanity. Like, I'm going like, are they sweating? Are they nervous about something? Are they how do they talk about their wife and kids? Like, it's those things. I want to see the humanity before I work with someone. And I'd much rather have someone who's imperfect but human than the, you know, crazy um, you know, who knows, some sort of personality disorder type. And there's many of them in business. I think it's roughly 5 to 7% of all CEOs are sociopaths. Um, and so they're out there and they're very effective, but um, life is too short to work with somebody who would do that to you. So that experience was horrible and that was probably the most foundational uh, breach of trust that I've ever had and it took me a long time to rebuild trusting people again. Um but now you know I've realized trust but verify >> the So in hindsight with him in that particular situation you would have invested more energy where >> I think diligence like if I had just called his ex- business partner or the person he said that you know he'd sold his company to they would have told me a very different story. I eventually reached out to all those people and they went oh my god I'm so sorry that you're going through this. I went through the same thing. Um, and I think just basic diligence is very important. And so now in a professional context, if I'm meeting someone socially, I just I'm I'll trust them. I'll watch their behavior. I won't tell them something that can really, you know, they can use against me. But if I'm hiring someone to run a business, we'll actually hire a background checking firm called Business Intelligence Adviserss. It's a bunch of former intelligence guys, and they just go deep on people. And so, um, you know, they'll call the school they said they went to, they'll call all the companies they said they went to, they'll interview them, they'll do a deep deep dig, and usually if something gets flagged there, I won't hire them. And if they say they won't do the the um background check, immediately I I wouldn't work with them. >> Got it. >> But that, you know, it's the sad reality of just like there's a lot of these people out there. They're they're incredibly charming. They're incredibly fun to talk to. They're very smart. Um and uh you know they're like a snake and they'll eat your eggs. >> It's one of those situation everybody will have many stories of getting burned and betrayal and it's what you do after the fact. A lot of people will just some people will take a stance of like I don't trust anybody and that's a way of operating the world and I get it. It totally I totally makes sense but it leads to smaller relationships, smaller opportunities and all that kind of stuff. If I were to meet somebody and like out of the gate there's like they want me to earn trust like I don't have time for this like I have a good reputation and all that kind of stuff. Um I I I don't need to you know jump through hoops so to speak. So the fact that uh you know you got burned in such a significant way and went back to the drawing board and got re-evaluated your relationship with trust and figured out what are some things that to do in the in the future to alleviate that. I was talking to someone um recently and they were telling me that the person they were dating was exhibiting all these traits and because I've hired so many wacky people, I've studied psychology a lot and I immediately flagged, okay, this pro person is a narcissist. Um I kind of gently said a few things and they didn't want to hear it. And I realized that if I had met someone who had met and a few people did meet this this Brian guy and said, "Hey, this guy's no good and whatever," I wouldn't have listened because I didn't understand the reality of what it meant to work with someone like that. In the same way that somebody doesn't understand what it means to date a narcissist until they do it. And so I don't know. I think if you read a lot of books, you can learn about other people's mistakes and hopefully avoid some of these things. But a lot of people um you just kind of have to go through these things and you just have to hope that they're not existential because no one can tell you how horrible it is to you know be in debt or deal with a psychopath or have an employee sue you or whatever those things are until you've been through them once. >> Yeah. There's a a friend of mine uh out in Colona has a philosophy of never make a deal that could put you out on the streets. Uh so like he has his like his nest egg or his goose egg or something like that and he protects that like like nothing else. um and is just very cautious around that. And then outside of that, he's willing to like make some bets and he takes some losses and and those kind of things. But it's one of those I just I've seen so many friends of mine who are incredibly smart entrepreneurs uh invest in businesses and start partnerships and it's easy to look at a financials of a business and and test its viability. It's not so easy necessarily to vet the individual. Uh, so to hear things like uh, you know, obviously looking at their their track record, trying to find their humanity in conversation, >> the most the to cut to the core, the most important question that me and Chris ask each other is would I let this person babysit my kids? >> Yeah. >> Right. And if the answer to that is no, you might not know why. It might be a gut feel. There's something weird or they I don't know, they they're not soft or whatever it is, but to me it's like I won't work with someone I wouldn't let babysit my kids. Yeah, that reminds me of a a saying of a friend of mine years ago. She said, uh, I won't go into a business partnership with somebody unless I could u have them over to my house for a weekend. But that was the actual test. Like she had to have them over at their house. And there was this one gentleman I was going to start a business with. And we went to it was to buy real estate in the Bahamas. And we decided to go together. And we've been friends for years. And we're like seven hours into this. and we went to this island uh on the outskirts of of Aluthra uh and we the boat didn't start and I was starting to see him get really aggravated. So we finally get onto the island, we walk around the island and then when we get back the boat won't start at all. The poor Bohemian guy can't get the boat started and like this friend of mine starts flipping out uh in like these times of adversity, one could say. And I was like, "Thank God I'm seeing this now instead of like two three years down the road when we're actually in some kind of partnership." So even like putting little tests like that out in the water um is uh is a good strategy. But uh yeah, I appreciate the I mean the share around that. And dude, this has been awesome. >> This was so fun, man. This is my favorite thing to talk about. >> I appreciate it. We covered like all the ground and uh yeah, it's it's like I said, I've listened to so many interviews of yours over the years and they're all brilliant in their own ways, but sometimes you just scratch the the the the tip of relationships and like there's so much more to learn from them. There's a really, you know, Morgan Hel wrote the psychology of money. He had this great, I think it was, it was in his new book. Um, >> and it's it's about how people think they want, what is it? They think getting money will gain others respect and admiration, aka like friendship and community. And in reality, that's not it at all. And the way more interesting skill set is the thing I'm obsessed with and you're obsessed with, which is how do you build amazing community? How do you connect with others? How do you have deep relationships so that when you're 75 and whether you're rich or poor, you have a million friends? Like that's all I want. I want my kids to think I was a good dad and I want to have a lot of friends. >> Well, you have a big couple days ahead of you putting your final touches on the event. I'm very excited. So, we'll put a a pin in it here. Maybe we'll revisit some of these in the future. But again, I appreciate you, man. >> Yeah. Thanks, dude. Good to see you.