How I Built a $180M/Year Business Without Making Myself Miserable

There's a lot of people that are suffering. So many entrepreneurs create prisons of their own making and one of the prisons you can make is your own narratives. The areas where you can make the most money are not the sexy ones. That was the moment where I was like I need to be an investor. When you're invested in a business is now one of the questions you ask yourself like how can AI disrupt this? People have so much scaffolding protecting them from real connection. When I talk to most entrepreneurs it's about freedom. I think all

businesses should be lifestyle businesses ultimately because what is a business if it's not improving your lifestyle? I was pouring my heart out and saying, "Oh my god, I'm running five businesses and I hate my life. Just so stressed out I almost break." And my friend just stops me and he looks at me and he goes, "I think let's just continue talking about where we just left off. Like how do you use money in interesting ways? You've got the people conference. You probably do a lot of other interesting things. Like let's let's talk about that. I

think that's fascinating." Yeah. So I mean when I first started making money um I went out and did all the things that every 20, you know, 22-year-old wants to do, right? I like went and bought big screen TV and like a sports car and like you know a house and all that stuff and I found ultimately it was really hollow. Like don't get me wrong like driving a nice car is nice and having a house is nice and stuff but total diminishing returns and what I when I actually pulled the thread on like why do

I like business? Business for me is a way to a like tweak things and make them better. So, like I'm the kind of person where like here's an example. Like I have a cafe I go to every day and I'm always looking at it and being like why is the lighting not better? Like why is that art on the wall? How why isn't the food better? Like I just want to make everything 20% better. Um I'm always a little dissatisfied. Um and so that's really fun. But the real reason I like business is that I

get to meet interesting people um and connect with others. And so I think business is a really great hack to make friends basically. And fortunately you get to um because business is this universal language, you can apply it to almost anything. Uh you know you could do restaurants, you could do journalism, you can do software companies, AI, like whatever you're interested in. You just kind of go down the rabbit hole. Um and so I've used it a lot in that way. And one of the things that I've done to invest in meeting interesting people is

just um basically creating events where I can connect with people. Like I basically one of the one of the things I started doing about six or seven years ago is I would just find people that I thought were fascinating and I would just cold email them and I'd say, "Hey, look, if I donated $25,000 to the charity of your choice, would you come and speak to me and some friends in Victoria?" And so it's great. I get all my friends together so I get to hang out with all my friends. We get to meet an

amazing person often because it's an amazing person. I can get even more interesting people who I have never met to come to the event and meet them. And then usually like I have dinner with the person who comes to speak or whatever. And so for me that's actually been this incredibly enjoyable way of using money to just meet all these fascinating people and it's resulted in this very broad network of friends. Um, and you know, when I was younger, so that's like later stage when I had, you know, more money to throw around to do

that kind of stuff. How did you do that initially? Like are there stages to like now you're throwing conferences and events, right? Like what are those stages? Well, at first it was like going to rooms that I didn't deserve to be in. So like when I had like a $1 million a year business, I um I think I spent $20,000 or something to go to the TED conference and like I was a nobody. like I was shocked I got in and um through that like you know we were talking earlier before we started recording about

Derek Civers who if people don't know they need to look him up he's such a fascinating character um but when I was at the TED conference um I was lucky enough to sit next to Derek and I said hey I've read your blog for a long time and he was so incredibly sweet he introed me to all his friends and we went out for lunch and I made more great friends from that and I just started going to TED every year and through that again it's just if you put yourself in a room of interesting

people you naturally a you get business opportunities and we were talking about um you know you increase your opportunity surface area but then you also just make all these incredible friends so now I have friends in the world of science and you know AI and uh music and all all these places I never would have before. Yeah. And you get to learn through them. Are there are there like any memorable moments like the Derek Civers connection like early on where like holy [ __ ] like I'm getting an insane arbitrage here like just by spending

a little bit of money and a little bit of effort and I just get to meet all these really interesting people like was the TED conference probably one of the biggest moments where like this is something I can start doing or Well, I remember I walked into an elevator at TED and I'm you know I'm not really paying attention. And I walk in the elevator, I press the button, and I just look to my right and it's Al Gore. And it's like, this guy was running the United States like 3 years before, and here I

am chatting with him. Or another time I was at a dinner, and I got sat at a table with Sergey Brin, and I talked to Sergey Brin for 2 hours. And it's like those opportunities where I'm just like, this would never ever happen to me. Um, and and frankly, I don't deserve to be here. But what I realized is if you're just interested, people are generally nice. If you're I mean one thing is like often people are like oh you know some gazillionaire or super successful person won't people people who are at the later stage

of their career love people who are at the early stage cuz they remember what it's like to be at that stage and if they don't they're a dick. Like I've definitely had that experience too. But um but most people will actually they want to buy into you. They're like how can I help you? Tell me about yourself. Uh, and they're excited because while they're, you know, all the fire's gone out of their eyes and they've been through everything, they love the start of stuff, right? So, they're they love meeting young entrepreneurs and and one you're

doing and exactly. Yeah. What are you most interested at the moment? Totally. Is that a big like, you know, talk to me about specifically about you do this yearly conference, I think, is it the the interesting people's uh conference or is that what it's called? like talk to me about that and the people that come to that cuz you've I know you talk to a lot of young investors and founders as well and I think you do a lot of like even just having the opportunity to talk to you here like that's giving back in

a way right so I really appreciate that and I think talk to me a little bit about that conference well um so in 2010 I went to this tech conference uh it was my first I think it was my first one of my first tech conferences and I'm sitting at one of those circular you know those horrible circular conference tables they put you at with like 12 people loud, you know, loud room and you can't really hear anyone except the person next to you. And I notice that the guy sitting to my right is a

big VC, someone whose name I recognize. And he looks to me and he says, "What what's your startup called?" He just assumes cuz I'm, you know, 22 or whatever. And I say, "Oh, actually I don't have a startup. I um I bootstrap my business. I started an agency and then I used the money doing that. started a software company and I start walking him through that and he just looks at me with this withering look and he goes, "Oh, a lifestyle business." And then he just turns just turns away from me. Just ended the conversation.

End of conversation. And he goes to the much more interesting founder on the other side. And so, you know, I'm left cheeks burning sandwiched between two people and just feeling like absolute garbage. Um, and I never forget that feeling. Um, so and then I contrast that against Derek Civers. Derek Civers was worth $20 million, super successful entrepreneur. He uh was kind of famous at this conference. And when some kid walked up to him and said, "I'm a big fan." He took hours of his time to connect with me. And I'll never forget that. And so

I think a lot of that um you know, I think paying it forward is super important and like connecting with young entrepreneurs and and helping them. And so what I do is actually um I try and create a few different kind of buckets for how I connect with people. And I've realized that you know as you get older um when you're in college or something you're just mashed together with people and you meet people naturally. But um when you get older that doesn't happen. You end up meeting a lot of the same type of person

or just the same people over and over again. And so, um, Nick Gray, uh, my friend who billionaire, the friend billionaire, I call him the friend billionaire. Um, Nick Gray is like my, uh, my my friend, and he, he has this whole system that he uses to make friends. I find this fascinating. So, he basically has, um, an email newsletter that he calls his friends newsletter. And what he does is he just signs people up for it uh, when he meets them. So, if you meet if you meet Nick or you follow Nick on Twitter

or whatever, you're going to get signed up for this newsletter. And he just says every month, uh, hey, I went to Hawaii. Here are my thoughts on all the best resorts in Hawaii. Um, hey, I started wearing, um, those weird open toe shoes. Here's the best type. Um, lately I'm thinking about how to invest in stocks, whatever it is. Yeah. And he shows his whole portfolio and totally. And so Nick just starts sharing, hey, here's who I am. So he puts that out in the world and there he starts to go on this list and

I got a list of people in New York and so he says oh I'm going to host an event. So he takes 40 of those people in New York based on how everyone interfaces at the event. He decides who do I want to be closer with and then basically he has this funnel that progresses to like really interesting and deep friendships. And so I've kind of stolen that in some ways. So, I have um I also have a friends newsletter and I've got uh 38,000 friends on it. So, it's like basically anyone who's ever signed

up for my newsletter, followed me or whatever is on there. Um but I use that as kind of my way of just having this big broad parasocial network, right? And then I also wrote a book. So, I've got people from the book who are interested in me. They sign up for the newsletter and then I've got this broad broad network from there. Um what I do is I basically um I do like events and podcasts and all sorts of other things. And what came out of that was this interesting people conference cuz I was like

you know I can only connect with so many of these people a year. 38,000 would be tough but there's so many interesting ones within that. And so what I started doing is um every year every summer uh I invite about 100 to 150 people of just the most interesting people who have struck me. I might have met them or I might have just started tweeting with them or or or whatever or I want to meet them. And I host this event and uh I've been doing that now for 3 years. And the whole idea behind

the event is I don't just want interesting people. I want people who the the goofy way I put it is make me feel warm and fuzzy inside. Right? It's like people where they're not only fascinating, but they're also really sweet and engaged and ask good questions. And then I just get those people in a room. And the whole mission of that is how do I get everyone to become friends by the end of it? And so Nick actually hosts the event with me and we just like go hard on like how do we get everyone

talking and connecting? How do we ensure nobody has my experience of being sandwiched between two people uh and then everyone feels special. So I do that which has been amazing. Been doing that for 3 years. Um the other thing I started doing back in probably 2010 was I got introduced to um entrepreneurs organization. You ever heard of that? So basically global network of um chapters in every city and it's just people who run small and mediumsiz businesses. And when I joined um they I just thought it was like some douchy like business networking thing, right?

I thought it was going to be, you know, a bunch of dudes in suits in a hotel ballroom. And they, what they do that's really unique is they do what are called forums. And so they break you into a group of six and you meet with these people once a month in a boardroom. And it's completely confidential. So nothing leaves the boardroom. And um you know, I go to the first meeting and I'm probably like 22 or 21 and I look like I'm 15 and it's a guy who runs a map company, like a map

software company, a woman who runs a popsicle company, a guy who runs a puzzle business, a guy who runs a woodworking shop, and I'm forgetting somebody, but it's this very broad diverse group. And they're all way older than me. And to be honest, I just thought I can't learn anything from these guys, right? Like they're all Oh, and another guy had a medical a medical business. And and um I just I kind of dismissed them, you know? I was like, I don't know about this whole thing. And as part of it, you start doing these

updates. You do give a personal update, family update, business update. And at first, everyone's a bit ky. You know, guy, I don't know. Everyone's like, um, my business is fine. you know, my family life is great. Um, you know, I'm good. I I don't have any problems. Nothing else to add. But but you know, when you spend three hours together and you do it every single month over the course of years, people and people feel comfortable and confidential, they start sharing really interesting stuff. And through that, I ended up realizing that, you know, in business,

my friend Brent Beore has a great line. He goes, "In business, everything tastes like chicken." You know, the problems in any business are kind of the same. It's like HR problems, operational issues, you know, through whatever. And um and I started learning a lot from these people who had been through things. Um and then on top of that, I started having these really profound friendships with people who, you know, it was like having this board of directors, not only for my business, but also for my personal life. So, you know, some of the best relationship

advice I've ever gotten has been in these forum groups. And now if you flash forward almost 20 years later, two of those people are um the executives of my will. Really? And you know, these are people that I dismissed that I said I'll never be friends with these, you know, learn anything from this puzzle guy. Exactly. And so I now have um four groups. So I do one a week every Wednesday or No, you've hosted these yourself. You've created them or I do them myself. I don't do them via EO anymore just because I'm a

control freak and I like to choose who's in my groups and stuff, but I do that and and so if you think about the rhythms of my life, I've basically created all these rhythms where I've got annual rhythms like that conference. I bring speakers to town and do that. I do uh my forums and then the other thing I do is something called the entrepreneurs lunch club. Okay? And what I do is I basically any entrepreneur I meet in town, doesn't matter if they're doing 50k of revenue or 50 million, I invite them to lunch

and we have this lunch format where we come in, it's an hour long, everyone's seated at a table, I choose who sits together so that it's all handpicked and then we prompt everyone. So there's no small talk allowed. It's like the the prompt would be something like um you know who or what is an energy vampire in your life right now? Uh way to answer that without going deep. Totally. And so we just prompt people to have interesting connections. So my whole social landscape is actually trying to build the funnel of interesting people and then

how do I convert those into deep friendships and I've learned a lot from Nick and I've learned a lot from Forum. Um but it's been that's been profound and that's such a great way to use wealth. you know what's what's like the like if if someone hears this like [ __ ] I want to do that like what are the three things you would start off by doing that are like the easiest low friction way to do it um like is it maybe just a once a month uh group or is it like you know

hosting a conference seems pretty uh intense like what's the easiest way to get started to do this yeah someone once told me um they had this strategy where they would go to a really big conference where they knew there was like three or four big names speaking and then they'd email they'd be a nobody But they would email all the big names and they let's I'll make it up. So So Bill Gates and Ray Dallio are both going to this conference. So you email Ray Dalio and you say, "Hey, I'm setting up a dinner with

Bill Gates um and some other interesting people. Do you want to come?" And then you go to Bill Gates and you say, "I'm setting up a dinner with Ray Dalio. Do you want to come?" And then you do that with three or four other people and at least one of them will show up, right? So my take is try and a go to those events, try to meet those people, try to be a fly on the wall and and to be at the dinner you don't deserve to be at because you're the person that set

it up. I think hosting is a profound power. And I think that um if Nick Nick says this, he goes, you know, if if nobody invites you to speak, build your own stage. And so I think that the way that I've done that has been by hosting um the lunch clubs and the forums. And I mean the forums are very easy to set up. You just need a boardroom. You need five interesting people. You need people coming. Yeah. You just need And I have a PDF on my website. I think it's never enough.com/forum or something.

And it has a blueprint. Tells you what to do. Yeah. I'm going to I'm going to steal that one. Everyone should steal that one. Or by the by the 2-hour cocktail as well. Totally. But you know, I will say like I've met all sorts of like really really successful people. the most interesting people, the best friendships I have their forum. And I don't have I don't have I have lots of very successful people in my forums. I I have connected far more deeply with people that are more normal than the big wacky super successful ones.

You know, I find that's actually where you get deep connection is who are the people who live in your city that you can actually become friends with and see. So even people like that aren't necessarily, you know, big tech founders or just like just some local back to like you know it was like puzzle company and I can't learn from that. Right. Yeah. And I think like if you had like you said you're in Amsterdam if you just chose five or six entrepreneurs who are you know at slightly below slightly above your level. Maybe you

have one that's like way above to teach everyone else. But I think there's something really profound that happens when you build those rhythms into your life. You can't help but becoming friends. It's like going to war with these people, right? You're just you have a lot of time with them and you got to learn to get along. And so you do and you know like they're all my best friends now. That's amazing. Yeah. I mean executives of your will that's that's insane. Is there something to the structured aspect of that that you think is really

helpful um that sort of is a forcing function for you guys to like develop those relationships? I think so because um so I'm in a forum with my business partner Chris and we have only been in this forum for five or six years and he had his own forum and I said hey I'm starting this forum. you know, do you want to join? Like, I don't know what we'll talk about. Like, you'll you'll know everything. And what's weird is I actually learn so much more about Chris. And I actually talk to him about really hard

things through this forum because what's interesting about the forum format is that you have to give highs and lows of all aspects of your life. And so, what I realized is when I go out for lunch with Chris, we have a general tendency to do two things. We gossip and talk about our friends and joke around and we talk about business and the deals we're working on and stuff and other than that, you know, yeah, sure, we talk about our kids and other stuff, but what's great about Forum is that it forces us to talk

about all these other things. And so, you know, there's been issues that Chris has been struggling with quietly that would just never get raised at a lunch, but I now I'm aware of. Um, and I've just found that, yeah, the depth of friendship you get is very different than if you go out for 10 lunches where people are just casually talking. The same thing. You're giving like an excuse to talk about those deeper topics that cuz like in this, you know, if you're if you're talking to someone at lunch or a coffee, even if it's

your business partner, like it's you feel self-conscious probably even then like bring something up deeply where like ah, you know, I'm going to leave in 20 minutes. Uh, you know, I don't want to spring this thing upon this. There's also there's a phenomenal book that came out um maybe two years ago by David Brooks called How to Really Know a Person. And I think one of the best skills that anyone can have is um playing tennis in a conversation. And what I mean by that is rallying, right? So a lot of people have a tendency

in a conversation to hold the they just keep hitting like they're just pounding and it's no fun, right? like you want to have a nice rally. And so learning how to ask questions and I've realized that, you know, if you can get to a point where you're both asking one another interesting and deep questions 50/50, that's the ideal. But if you really want to make someone feel good, and a lot of people do this, they'll just grab the mic. But if you just ask them interesting questions, you can actually learn all sorts of amazing stuff

for them. So for example, I was having lunch with a guy recently, and he just made, you know, very off-hand comment. He said, "Um, oh, I don't have my kids that week." And so I said, "Oh, um, you got divorced, right? How how fresh is that?" And he went, "It's actually like 3 months ago." And I used the David Brooks line. The David Brooks line is, um, how was that for you? Very open question. What did that feel like? You what was your experience of that? It's like those very open-ended prompts. And we ended up

talking for cuz I I got divorced, too. We ended up talking for 2 hours. just we deeply connected and before that you know we'd both been kind of like closed body language like we're talking business maybe we're kind of like comparing notes and like status there's like a second conversation going on in your head totally and so I I like to it goes back to that what's the worm gooey center of somebody and how do you get to that because you know there's so much people have so much scaffolding protecting them from real connection um

the other thing I like to do is um do you know Alando Baton heard of him he's like a I I think he's Swiss. He's like a modern-day philosopher, and he's written all these amazing books that I love, but he did this thing um in London about probably 10 years ago called the School of Life. Oh, I I've seen you share that. Yep. His his idea was to create kind of a modern version of a church. So, it's a place where people congregate and talk about interesting ideas and connect. and they started making all sorts

of amazing books and and there's everything from how to um how to understand Greek and Roman philosophy to um how to get over your childhood. Um but they also have all these wonderful little box sets of cards. They're called conversation cards and there's ones for couples, there's ones for friends. The one I like is called the loser game. And you I keep it in my backpack at all times. And whenever I'm with old friends who I know really well, I'll pull out the loser game and we'll just start pulling cards. And the reason it's called

the loser game is because you lose if you don't answer the question. And the questions are really intense. So you pull it out and an example question would be um if your parents were being unkind, what would they say about you? Right? like how have you failed the people you love like things like that and I have just found that there's something about just prompting and asking interesting questions that again just unleashes all sorts of interesting conversation that's amazing that's a hack though like you don't have to be good at it like there's you know

the card sets there's these books there's these you know go-to questions like you know how does that make you feel or how was that that you can sort of rely on to get this conversation rolling I love that you've talked about this before in a podcast the school of life I I I bought a I bought a set afterwards. It's a It's a great little hack. You mentioned a little earlier on when we were talking about conferences um and sitting next to the guy who gave you the cold shoulder. Um talk to me about lifestyle

businesses. Like I think this is a little bit related to you know the goal of life you know having these warm relationships having these fun moments and deep connections and you know the juxaposition that might have with raising money and trying to get this big business going. um like talk to me about lifestyle businesses and you know why that has a negative connotation and maybe it shouldn't. Well, I think lifestyle business the idea is you know if you're a venture investor or an investor at all and you hear a founder say something like um you

know I just want to make a hundred grand a year and go surfing, right? That's that's not going to make me money. That's I think in their brain that's what they think of as a lifestyle business. It's something all but I think it's fascinating. I mean I understand why a venture investor wouldn't like that. A venture investor is there to have a billion dollar outcome and the structure of their fund requires it. So fair enough. But I do think that it is unfairly maligned and I think that people view it as okay so door one

is I have a little cute lifestyle business. Door two is I raise a hund00 million dollars and I go crazy and I try and build a public company. And I think there's a door three and I think that's what I took um which is how do I build a business that suits my lifestyle but isn't artificially limited. Right? So if you say um let's say you're selling your time and you sell your time for $100 an hour but you want to surf four four hours a day. Yes, you're going to artificially limit it. your business

will never scale past that. But if you had a business where you went surfing, but you had 100 employees and you built the whole thing and structured it in a way where you could still go surfing, but you make $50 million a year. It's a pretty damn good lifestyle business. And I think it is actually good for everybody. I think your employees make a great amount of money. You have a lifestyle you enjoy. Uh your investors are happy if you have investors at all. Um so that's kind of the way I think about it. And

I think that, you know, if you think about the people I look up to, um, the whole reason I got into business was because, um, I didn't want my parents to be able to tell me what to do. That's it. You know, I the moment I remember, um, my parents would ask me, "What do you want to be when you're older?" And I would just be like, "I just want to be older." Like, I just want I don't want anyone to be able to tell me what to do because my whole life um, you know,

you could explain something. Let's say I'm I'm doing something the wrong way and you say, "Oh no, Andrew, you should do it this way. This is a much better way to do it." And it's totally logical. I will still resist you. Like I have a weird mental thing about that. And so, um, when I think about who I admire, I look to people like Jason Freed. Uh, we were talking about Jason before this cuz I interviewed Jason and I've followed him for a long time. Um, but Jason, for people that don't know, started a company

called Base Camp with David Hanmire Hansen. They're the creator of Ruby on Rails. They're, you know, amazing software business. And he's always had this very contrarian approach to business where he said, "I'm not raising money. I will have no outside investors." Although Jeff Bezos invested as like a token thing. Um, but he has nobody who can tell him what to do other than maybe his business partner. And um I really admire people who just know that about themselves, who say, you know what, I I need to build this thing so that I can do what

I need to do and I'm not going to artificially add all this complexity in. And I think, you know, at different times I've strayed from that path or I've I've done it to a more extreme degree than I should have. But I think um when I talk to most entrepreneurs, it's about freedom. And so many entrepreneurs create prisons of their own making where they're like, well, I really want freedom, but in order to get that freedom, I'm going to lock myself up in this complicated prison where I can't get the keys unless I do XYZ

instead of taking the easy path. Um, and I think, you know, ultimately striking your own path is really great. And so I think lifestyle businesses, the you know porative term for some people, um I think all businesses should be lifestyle businesses ultimately because what is a business if it's not improving your lifestyle? Um and and I find it hilarious when people are like, well, you know, think about um you know, you could make all this money for your future kids and family and stuff. I I think like I understand that but I think like generally

it will just ruin your kids and it'll ruin your life cuz like I think generally like large amounts of money are a toxic force for all relationships. That's why trust fun kids like you know it's a stereotype for a reason. Do you have any like moments in time where you just like what what moments in your life was like a discovery moment where like oh okay maybe I shouldn't be doing this like maybe I should be delegating or maybe I actually don't like this aspect of this business or maybe this other subject interests me more

because to your point like every business should be a lifestyle business but it should be the lifestyle of that founder and figuring that out I think is very tough. How did you go about that? Like have there been any moments specifically that come to mind where like that was an aha moment? There's been a lot of them. I think the first most important realization was I should not be doing anything I'm not good at. Um, you know, in the early days, you know, I would wake up I'd wake up at 2:00 in the afternoon. Honestly,

I'd wake up at 2:00 in the afternoon. I would frantically do an hour of email. I would then do sales calls for this when I was running my digital agency. I'd do sales calls until 6:00. Then I would have dinner with my girlfriend for an hour. And then from seven o'clock until 4 or five in the morning, I would be the project manager, I would be the developer, and I would be the designer. And I was doing all this stuff. And then on top of that, I was also trying to do accounting really poorly. You

know, legal admin, everything. And my answer to myself when I messed up was always, well, I should just try harder. You know, I need to just whip myself harder. I should read another book. Mh. Um, and as soon as I hired a developer and realized that, oh my god, you know, my developer Ally and Billy, they love coding and they're happy to do this and I can then go focus on the things that I love. That was like a total breakthrough moment. Um, you know, the next one was um even the things I'm I'm good

at, there's elements of it I don't like and I can start delegating those. So, for example, I hired someone to run sales and I would only be there for the first meeting or the critical meeting, which I loved, and I'd hand the keys there. From that point, um, it was, "Oh my god, I can hire a CEO and they can run the entire business." So, I think like entrepreneurship is just delegation, right? That's all we're talking about, right? If you don't delegate, you're an employee, right? And your boss is a lunatic, you know? It's you,

right? Um, and so it's been a series of like abstracting away business. The other experience I had was in 2014 I sold my first business. Um, you know, I remember I was walking I was on a hike with a friend and I was just complaining. I was pouring my heart out and just saying, "Oh my god, I'm running five businesses and I hate my life and I'm, you know, so stressed out and, you know, I'm I'm like on paper I'm rich, but like I don't have any money and like, you know, what am I doing?"

And my friend just stops me and he looks at me and he goes, "You know, you could just sell one of the businesses." And I was taken aback to me. It was almost like um, you know, somebody has said, "Hey, you know, you could sell your baby for science experiments and then buy alcohol." like it seemed like horrible. I was almost offended, but I started thinking about it and I um I ended up talking to a buyer for one of our companies and we sold the business and I saw how stressful and horrible that process

was and how frustrating it was for me. not only in terms of the administrative burden and how the how brutal the negotiation was and how unnecessary all the you know all the legal complexity and all this stuff was but then also the way that they ran the business and I'd say after you sold it you may after we sold it cuz I stayed on the board and watched watched them run it and the way I would put it is it was like watching a new uh adopted stepparent parent my child and I didn't like it

I didn't like it I didn't like the way they talked them I didn't like the way they disciplined it you know I didn't I didn't like what they're doing with the kid. Uh, and in that instance, I ended up buying it back. But, um, in that moment, that was the moment where I was like, I need to be an investor because there's an opportunity. There's a lot of people that are suffering um, unnecessarily and we could be the buyer. You could be the nice steparent. We could be the nice steparent. We can we can do

that for founders. Um, and that's really resonated. Now, we own 40 businesses. Um, but that was for sure like a huge pivot point for me as well that you realized like I want to be investing and I want the up the highest level of delegation to be what I do every day. Totally. I just want to be um a I want to abstract away business to another level. Right. I realized I could buy companies, right? So, so I you know it was like start company, delegate the work. Yep. Uh delegate management, delegate CEO. Then it

was, oh, I can just buy a company. I don't even have to start it. I can skip all that stress. I can hire great people to run it. Yeah. And I can save the founder and make their life awesome. So again, it's all about these. It's like a transaction of like, you know, you've got a problem. I've got a problem. So the problem I have is I don't like doing coding. Well, there's developer for that. In the same vein, I'm a founder. I don't like running my company. Well, great. Tiny can come in and we

can run it in a way that you'll be happy with. you can still you can either take all the money off table or sail off into the sunset or you know do whatever you want to do. Um so for me it's all just about how do you lean into those things that you actually love doing and still get the maximum result you know without artificially capping it. Right? We've been able to make a lot of money by being frankly lazy and leaning into being lazy and going what do I actually like doing? Yeah I think

there's there's two interesting a lot of questions come to mind. Two of them I'll start with the first one. one, how did you know how do you go about leaning into your strengths, right? Like that that's one question like I think to your point earlier on like you know you're lazy you know in in your early days you might have said you know just work harder or you know you're you're making excuses for yourself like how do you go about leaning into your strength and sort of maybe maybe better put like leaning away from your

weaknesses even and sort of admitting that. Well, we were talking before the pod and I I think I said like it took me until I'm 39 now. I think it took me until 35 or later recognize my true skill set and where I'm weak. Um, and I increasingly believe that people actually have, you know, you asked me a question. You said, um, you know, what does Derek Civers do? What can we learn from Derek Civers? And I I kind of said, look, I don't know you can learn anything from Derek Civers because Derek Civers has

a different operating system than I do and maybe you do. Um, I know for myself, you know, I remember sitting with Derek in New Zealand and I said like, "Oh, you know, what's your," we haven't caught up in a while. And I said, "What's your normal day these days?" And he goes, "You know, I spend a lot of time alone. Like I I sit on my computer and I have um I think it's Vim or Terminal or whatever." And he's like such a hardcore programmer that he's written all his own software. So, he does all

his writing in the terminal. He does all his email in the terminal. And he just writes all day. He writes down all his thoughts and that's how he thinks. He's not on Zooms. He's not on calls. He's not getting a bunch of coffees with people. And I, you know, that's a wonderful idea. That sounds nice in theory, but I'm incredibly extroverted. I can't do that. And so, you know, the way I put it is like I I think, what did I say? I said, um, you know, you can't use Derek's lottery winning numbers for your

own lotto ticket because you just have different hardware. Um, I think accepting that is important. And I think that for me um you know it's been a process and like you know obviously I embraced not being a great programmer and then not being a great manager and then ultimately not being a great CEO. I think I'm a good CEO at certain scales but I'm not a good CEO at most scales. Um and finally, what's been really fascinating is actually embracing there's a cheesy um term used in EOS, entrepreneur operating system, which which I actually really

like. And it's the visionary and the implement and the visionary's job is to be the ideas person, come up with a big paint paint the picture, the strategy, the culture, be the founder, but the imple's job is to actually implement that vision. And it's funny, we went through an implementation process of EOS in one of my businesses. And the EOS implement, I kept putting up my hand and saying, "I I can do that." You know, cuz you go through this process where you say like, "What are all the jobs to be done at the business?"

And it would be like, "Um, you know, this accounting thing and there's no one to do it." So, I'd be like, "I can do that. It's fine." And he would stop me and he'd say, "No, no, no. You're the visionary. You should have no deliverables. kind of like I don't work well on deadlines. I don't, you know, that doesn't lift me up. And it's not embracing the thing I'm good at. And I hate to use the term visionary cuz it sounds super cheesy, but like actually leaning into just saying like, "No, I'm the founder and

my job is to be the founder and it's other people's jobs to implement, to operate, to do all that stuff." And I have found such profound peace from that. Um, and then on top of that, like, you know, we're talking about um, ADHD and biology and stuff. So, you know, I think Derek Civers has different biology than me and you have different biology than I do, etc., etc. And for me, um, I found out about six months ago that I have ADHD. Never thought I had it. you know, I've been successful at work and, you

know, I've have lots of coping strategies and stuff, but I was doing a cognitive test for my doctor and they just looked at me and they were like, "Oh my god, you're you have like the working memory of like, you know, an old 85year-old man. Like, this is weird. Like, you should really get checked out and you might have ADHD." And so, I got checked out and I do. And I started taking Bance, which is how they treat, you know, they give you stimulant drugs. And I remember I took it And I felt both profoundly

happy and profoundly sad. I felt profoundly happy because it was like um the dishwasher was running and there was, you know, I was in like Time Square, right? My brain was like Time Square. There's just endless ideas and overwhelm, constant feeling of overwhelm and drinking from a fire hose. And when I took Viveance, I just felt calm and I felt like, oh, I can decide where to direct my thoughts and how to think. And then on the flip side, I felt sad because I went, I'm 40. I've never felt this before. And it's so interesting

because I think um when they do studies of ADHD, it shows about 30% of entrepreneurs or more have ADHD really than the general population. And for me, ADHD feels like a little itch in my brain. Got to do stuff. I need to be productive. I need to make the itch go away. And the analogy I used to you was if you had seasonal allergies um starting a business to make your nose stop running or sorry starting a business to to uh cure your ADHD or anxiety is like saying I'm going to go be a marathon

runner to clean my nose when I could just take an antihistamine. And so I do believe like actually leaning into the mental health side and the biology side can be so much more profound than any level of success or you know business outcome or anything like that. Peace of mind like what's more what's worth more than that. Do you think it takes someone else? You know, the doctor case might be a bit extreme because like maybe one of the few people who can diagnose that, but for other qualities and traits in yourself, do you think

it takes someone else telling you that or, you know, giving you feedback generally to realize that or what when when have you sort of come to that in solitude? Well, I think people know when there's something off. Yeah. Right. So, my whole life I've always felt different for sure. And I've always felt that um I will let those around me down because I will forget the important things they tell me or I will be zeroed in on something or I'll be irritable when I'm interrupted or whatever. I never knew what it was. I thought it

was anxiety. I thought I had an anxiety problem and I thought I had an anxiety problem because I didn't have enough money or I didn't have enough businesses or I didn't have enough friends or, you know, whatever, right? And so, you know, I tried all sorts of different things, you know, meditation and exercise. And did any of those like work marginally or 100% they all help. Um, but but I had all these this framework of coping mechanisms and, you know, using a to-do list and a calendar and stuff, but ultimately it was like this kind

of house of cards that if any one thing didn't happen, like if I didn't meditate in the morning, then my whole day was not quite right or whatever. Um, so I always knew there was something. I just never knew what it was. And I was just so shocked that it was that because I'd never even was an option. To be honest, I had dismissed ADHD. I thought ADHD was a Tik Tok trend. Yeah. And I remember I felt like a real jerk because my girlfriend a year before I got diagnosed, she'd said, "Oh, my friend,

uh, you know, XYZ got diagnosed with ADHD." And I just rolled my eyes. And I was like, "Oh, great." Like she should probably take some uh some meth pills. So I I was a real I was totally in denial about it. Um and yeah, it's hilarious that I have it. Very ironic that you're so in denial. That's insane. That's incredible. I Yeah. Have there been any other things that you know medically like you got checked out and you're like I probably should have done this earlier or I think a lot of it is um I

think you know that I started taking an SSRI for anxiety which helped for sure but I think what I was treating was the anxiety that was downstream of the ADHD like another coping. Um I think people are very scared of pills. I find that very interesting, right? Because go going back to the allergy thing, right? Like nobody nobody I mean, yeah, you hear some people who are like, I don't want to take Claritin or whatever because I don't like taking pills, but for the most part, when you have an allergy and you have a runny

nose, you just take a pill and it goes away. And it's hilarious because, you know, when you take an antihistamine, there's histamine in your brain. You're affecting your entire systemically, you're affecting your entire body. You're changing how you think. Like when you take antihistamines, it does actually change elements of your mood and other things. And yet when I say to people, because I've been very open about taking an SSRI and and ADHD drugs, people seize up. They get very you're taking pills. What? It's like um I think it's a little bit like um you know,

Botox. If you told someone 10 or 15 years ago, you took you got Botox, they're like, you're vain. This is crazy. And now you say it and it's more normalized. And I think it's just, you know, it's on a continuum. and people will get more comfortable. But um I'm a big fan of figuring out what molecules your body needs to feel good. And and a lot of people who don't take these drugs and have untreated anxiety or ADHD, they medicate in other ways. Like all through my 20s, I was basically an alcoholic, functional, but you

know, I was drinking six drinks a night for many of my many years in my 20s. And that was how I was coping with the stress of work and probably my ADHD symptoms. Yeah. So, it comes out in some other way, you know. Yeah, that's a Yeah, that's a great example. Like just maybe looking at your life and auditing like what am I actually doing to try and cope and you know, can I get this medically diagnosed or can I just be a little bit more upfront and honest with myself in terms of why am

I doing these things? Like, you know, well, and the problem is that people build narratives for everything, right? Oh, I'm I'm the way I am because my mother did XYZ. And don't get me wrong, that is a profound effect and nature nurture, you know, there's there's both sides, but um you can build a lot of really dangerous narratives like, "Oh, well, I'm just not good. I'm I just, you know, um I just can't be spoken to after 4 p.m. because I'm exhausted or whatever it is." I think investigating those things is worth it. And I

think that fortunately, we all have the world's best doctor in our pocket with Jad GBT now. And it's quite formidable. you know, it can look at every single scientific study and very objective and go very deep on that and I think that's really exciting. Um, finally, but but no, I think people are too precious about that stuff. Um, in terms of other stuff, no, it's all been more preventative like, you know, taking a statin or um getting annual uh testing and that kind of stuff. Yeah. So there weren't any other narratives you think in your

head that you were telling yourself that got broken as a result or Well, there's lots of um or that might not have been true. There's lots of I think I am you know I mentioned putting yourself in a prison of your own making and one of the prisons you can make is your own narratives and especially I think that's especially dangerous when you're a public figure and you share all of your ideas. So what I noticed is, you know, I wrote a book and in my book I said, "Here's my take on all these things

and this is what I'm going to do go forward." Yeah. Well, um, I felt a real pressure. I went, "Oh my god, I've just laid out my I've said I'm going to build a road here and it's going to go to here over the next 50 years." But, you know, already it's only two years after I wrote the book and I'm like, "Well, actually, I kind of want to detour here and I want to focus on this or whatever." And I've changed. And I think that um you can really trap yourself in public statements. And

I think that um one of the one of the things I've been trying to focus on lately has been um the courage to be disliked, right? I think that most people uh don't want to be disliked and it makes it very hard makes it hard to live an authentic life because you start uh living for other people and living based on public statements from other people. 100%. And I think a lot of if you there's a wonderful therapist um who I've been lucky enough to work with actually directly and also listen to all of his

content and stuff but Paul Ki um and I remember he did an amazing series with Hubberman um maybe a year ago and he does a deep dive on how they do how they kind of analyze someone's psyche and how they work with someone to change and he talks a lot about how the most important thing that a great therapist does is they work with the person to rewrite their internal narrative. So, you know, it's not this happened to me, it's, you know, how do you shift that away or, you know, this happened to me, then

I learned this, now I'm like this, right? To be a better direction. And I think that work is Yeah, that's that's kind of the job. And I think that you have these moments every 7 to 8 years where you have to pivot your whole life. You said you're 23. I remember 23 was one of the worst years of my life. I was um dating someone who was going through some really bad mental illness. Uh I was completely lost. My business was a disaster. Um and I remember this big moment of change and then I've had

another big moment of change at about 31. Had another one at like 37, you know, and it's couple years down the line. It happens. Yeah. It moves in cycles. Yeah. Do you think there would have been situate Let me rephrase that. Is anything in that moment when you were 23 or when you were 30 that you could have done or could have happened that would have prevented you from making that change and staying in that same rhythm or I don't think people change unless they're in rock bottom. Like I really believe that people um people

don't I I I really believe if you believe if you want people to change around you, you're doomed because unless they hit a breaking point, they will not. There's no forcing function. Uh there's no forcing function. And that goes for me too. I think that I need to hit these points where I'm humbled or I fall in the mud or I I'm just so stressed out I almost break. Um and I've been fortunate none of those have been like horrific. I haven't been in the street naked screaming or anything like it's no no usually it's

been like relatively more just existential stuff but um but yeah I mean those catalyst moments are really important and I think depends on your personality. For me it usually is I start getting disillusioned. and I start getting a bit of like anhid where I'm like, am I excited to get out of bed and do what I'm doing today? Um, am I excited about who I'm spending my time with? Do I like my calendar? And when those the answer is no to that enough times in a row, I start to know there's something going on and

there's some internal work to do. Yeah, you've talked about going on I think it was a month-long silent retreat. Um, other things like that and let's talk about that experience a little bit. like other things like that that you can do yourself to sort of give clarity to those questions and give the answers sort of let them surface themselves instead of just being so busy that you know you never get to the truth. Um so I did a I didn't do a month-long retreat. I think I'd probably have the mental breakdown where I'm naked in

the street if I did a month silent cuz I love to talk. I I've always wanted to do one of those silent retreats though. What I did was different. It was um I remember I listened to this wonderful interview with Dr. Anna LMK who's a um she's a scientist who works on addiction. And the reason that I was interested is we've funded some research around treatment of um opioid addiction and stuff. And so I just was listening cuz I was like, "Oh, it applies to the philanthropy side." So I listened to this interview and she

said something really interesting. She said, "People can get addicted to anything. the the dopamine circuit can fire when you drink a fizzy drink, when you have chocolate cake, when you read a vampire novel, could be anything. And um I started realizing that I have all these, you know, little addictions. And she talked about um at Stanford she works with both people that have severe addiction, but she also talks to people who have porn addiction, who have video gaming addiction, um anything. And she basically said that all addiction um to reset your dopamine addiction circuits, it

just takes six weeks of abstinence and it's total abstinence. And so the two big takeaways for me were one um there was a lot of behaviors that I was doing where I was addicted to email on my phone or whatever. And she basically said you need 6 weeks away so so not nothing. And then you also need to do what's called self-binding. And self-binding is if you're an alcoholic, you do not permit alcohol in your house, right? Or you create systems that you know no one everyone knows you're not allowed to have alcohol or you

know things are locked away or whatever it is. And I started applying that to my own life. So I one summer I just said um I went to my assistant and I said uh I'm on sbatical for the next 8 weeks. Um I'm going to be unreachable according to everyone that reaches out to me. You just have to I I put an autoresponder on my email. I said, "I'm out of communication. Um if it's an emergency, talk to Karen, my assistant, and she can get a message to me." Um but otherwise, I'm I'm fully out.

Um and people I find people generally respect that um when you do that. And as long as you give them other paths, so I said like, you know, if it's a deal, go here and if it's something else, go here, right? And I spent the entire um month and a half up at my summer cabin and I went up there with my kids and the only thing I the only electronic device I permitted myself was a Kindle, right? And so and a camera. So I had a really nice Leica camera and a Kindle and I

was like an addict in withdrawal. like when they describe like, you know, your skin's crawling and you're irritable and you're snapping at everyone and you're kind of like I'm angry at my my wife even or my ex-wife now, but angry at my wife even though she had nothing to do with it. Um, but something amazing happened after like 3 or 4 days. I just started feeling incredibly calm and I noticed my brain just kind of cooling off. And so I spent this 6 week period of just wake up every day and I would have a

quiet coffee and I'd read a book and think and I'd watch the kids play and I'd go on little excursions with them and I wouldn't even allow myself music. I remember at one point I walked into a cafe to order an Americano and I heard like you know just music, right? And I was like oh my god this is like the first time I heard Radio Head like this is amazing. And um and so it felt great. And when I came back um I did the self-binding. So I locked email off my phone. I I

locked all social media, all news. And I've mostly stuck with that. Um there are a few exceptions where like I allow myself to do I think it's 5 minutes a day of Instagram cuz like I post sometimes or like people DM me. Do you hold yourself to that or do you Oh no, it's full screen time. So So my girlfriend actually has the code to my screen time. There's no there's no There's no getting out. And there's actually a great app. So, the ones I'd recommend are um Freedom. So, it's freedom.to. And what you can

do is you can they have this special mode called lock mode where you cannot turn it off except certain times of day. And so, I made the times of day midnight and 5:00 a.m. So, unless I want to get up really early, so I have to be really desperate to to get access. And I've it's been like that for 3 years now, and I still don't have access to anything. Um, so that's that's been profound. Um, and I think that so much stress in life comes from awareness of problems. Um, you know, you think about

talking about like what our operating systems are and the hardware we're running on. We have 100,000y old hardware. We're still programmed for being in like a hunter gatherer society. And I think in a huntergatherer society, you you want to be aware of everything. You want to be aware of everything, but you're only aware of like, you know, you're not aware of the problem in the the community that's 10 kilometers away, right? Our brains are not designed to be aware of every problem in the world because no matter what on the internet, there's always a problem

or a crisis. And in your inbox, there's always a crisis. And on social media, there's always a crisis. And so, basically, I try to blind myself from crisis. And I've found that, you know, I was really scared that it would affect my investing or I would be checked out of life or, you know, I wouldn't be engaged um in politics or whatever it is. I actually still find out all the things because I have lunch with my interesting friends and they tell me what's going on and occasionally I'll get an email from someone and they'll

talk about what's happening and if I'm really curious, I go and chat GBT and say, "Can you summarize this problem?" Yeah, but it's just I think um people create an unlimited inbox for their brain and it's just being filled with thousands and thousands of problems and ideas and I think that's really dangerous. Let's transition then to talking about you know your productivity stack. How do you make sure that you know to your earlier point like there's every day there's so many things happening and we're not used to the noise outside of our tribe coming in.

Like how do you go about manufacturing an environment that's you know productive and you know not super chaotic? I think the most important thing that I've found is that I don't see the problems until I'm ready to deal with them. Maybe I'm aware of them, but that they're in a place. So, one of the biggest problems I have is I'll be in the shower and I'll think, "Oh, oh crap. Uh, I was supposed to get back to that person or you know, you want to do a podcast and uh, you know, I told you we

would have a mic for you, but we didn't." Or, you know, whatever it is. I have realized that I can't trust my brain. And the most important thing is I get it out of my brain because otherwise I'll be just taking another shower in three days and remember it again and feel even more stressed. Right? So um probably about 20 years ago I became obsessed with David Allen's getting thing things done framework which is was very popular 20 years ago. I still think there's tons of people that do it. And the core idea is basically

that you have an inbox where you dump all of your problems and ideas. And it could be clean the garage or it could be write the next great American novel or it could be a bucket list item of I want to go to the great Grand Canyon and skydive or whatever. Um, but it all goes in there. All of your wants, desires, needs, everything. And then from there it's converted into projects, next actions, tasks, all that kind of stuff. And so I've been doing that for a really long time. And that's kind of the most

basic principle that I use is get it out of my head. because if I get it out of my head uh and I know it's in a system, then I feel that I can actually relax, right? Um from there, the most important thing is that I don't see it until I need to again, but that I know it's somewhere. And so, um basically what I do is um I I over the last probably 6 months, I've been reworking my whole productivity system. Um from an email standpoint, um I used to have my assistant do my

email. Now I actually have um AI do all of my email for me. Um so every email I get uh it gets sent to OpenAI. Uh the API looks at it and figures out is this something that needs like a signature like a legal document that goes to my general counsel. Um anything like that's a deal that automatically gets sent to the deals team at Tiny. Um basically like anything that can be sent somewhere else and routed gets routed without me being aware. From there, it also decides what is actually something I want to see,

right? So, if it's um let's say it's somebody who read my book and wants to meet me, well, that will get filed with a label and that's something that's maybe lower priority, but that I'll get to and I'll see later. Um, and then really what I'm left with is, you know, I might get 200 or 250 emails a day, but I am only getting eight or nine that actually matter and then everything else is filed for later. And so what I'll do is kind of batch. I'll say um maybe Monday, Wednesday, Friday, I do email.

Otherwise, I'm not looking at my email. And when I'm in my email, I'm going to do the eight most important ones. Then maybe I'll say, you know what, I feel like it's a book day. I'm going to go through all the booknotes I got and I'm going to go through those. Or um logistics. So it automatically figures out who are people that are friends and that need to schedule my time. And I'll kind of go through and be like, you know, I want to meet this person, I don't want to meet this person, whatever. Um,

and then in terms of actually doing the work, um, I use a tool called AUFlow, which I just found, which is like amazing. How do you spell that? A K I F O sorry, A K I F L O W. Okay. Um, I think it's like a I don't know where they're based. Somewhere in Europe. And I'm just so impressed by this company, but they basically have created like almost like to-d doist married your calendar. And so the principal idea in it is that you break all of your tasks down into projects and stuff, but

you actually say how long they take, right? So, you know, is this something that's deep work that's going to take 4 hours or is this a one minute email? And so, as you're going through your inbox, you're kind of saying 1 minute, 1 minute, 1 minute, 2 hours. And then it prompts you every single day to plan your day. And so, what I find that I used to do is I would say, um, okay, today I'm going to do 40 things. I'm going to do, you know, 18 hours of work in the four hours I

have allotted. And since I started using this tool, I actually book my day out and figure out what I need to do. Um, and that's been amazing. What I have found is no matter what your productivity system is, it almost never stays perfect forever and it keep you have to keep tweaking and stuff, but that's where I'm at right now. Um, and then separate from that, I also use a whole bunch of AI tools. Um, so I've found that, um, you know, I need a lot less admin support. I need no legal support. Uh, I

mean, I still have lawyers review stuff, but but like we just did a, um, we merged together three companies in one of the businesses and it would have cost us $75 to $100,000 of legal bills. It cost us $2,000. Really? All we did is we went to a lawyer at the end and we said, "Hey, uh, another law firm did this. Can you can you just tell me if you spot I only want you to tell me if you spot anything that's really critical. Do you see anything critical? And the lawyer was like, "Oh, this

is great." Like, "Who did this and he wasn't very happy when we told him it was Claude." He was like, "Shit." Um, and then even stuff like um investment analysis. So, I will often dump a data room into Claude and just say like, "You're an investment analysis or an investment analyst. I want you to give me your critical thoughts on this." uh or sometimes we'll be doing board meetings. I'll say, "Hey, um if you were a board member, what would you take issue with in this report?" And then we'll tweak it accordingly to ensure the

board feels, you know, adequately um informed about everything. Like I just find that it is a bicycle for the mind in that way. Um, so as an entrepreneur, we were talking earlier and I said, um, you know, Chris, my business partner, always says there are no problems, there are only people problems. And I just think with AI, you just have fewer people problems and more fun. Yeah. What what has been one of the most drastic examples? Like you saying, you just saved like $98,000. Like what have been real tangible examples of AI just getting better

and better or you guys realizing the implementation of it is just insane in in your businesses? Well, um, in one of the businesses I think we reduced our support tickets massively. Like that's an obvious one that I think a lot of people are aware of is just so much manual. I remember there's this book called um, [ __ ] Jobs by David Greyber. I think it's in this book. He talks about how um there's so many humans that have jobs that are like um you're the guy at the hardware store and your job is to

take the paint can from the customer, turn around, put it in the paint shaker, press the button, and hand it back. And it's like that shouldn't be a job. Like the machine should just be self-s serve and you're wasting human potential. Um and I think there's a lot of human potential that's wasted on very manual things. for example email that comes in it or it so I think those things are really exciting. What I've been astounded by is some of the advice that it's given me. Like I um I trained a claude project on all

of my personal finances. I said here's my holding company. Here's all my personal tax filings. Tell me I want you to be a tax analyst. And I to be clear, I have a full-time tax person who's amazing, but he missed this one little thing. And Claude said, "If you move if you pay down this credit line and you move this thing here, it was like a a mortgage or something on one of the houses. If you just move this here to here, you'll save $100,000 a year of tax." And I was just like, "Oh my

god, this is crazy." And it was correct. It's like free basically. That's incredible. If you thinking when you're starting a business, you know, how would you think about the AI risk now or when you're investing a bit in a business maybe is a better example? is now one of the questions you ask yourself like how can AI disrupt this or you know how does this AI get affected by it or totally um you know I think all the finance world is just dressing up uh finance to be confusing right you know like they use a

lot of terms that make it you know seem really complicated but all that investors are doing at least private equity and public markets investors they're saying is this company going to keep existing how many years will it keep existing ing and will the cash flows or the profits increase or decrease over time? Very simple. Um, and historically that has been a lot easier than it is today, right? And I think the reason for that is just competition. As more and more venture funding has gone into different industries, they become inherently competitive. Um, you know, I

experienced this about 15 years ago. I started a a to-do list productivity app because I love GTD and I started what I you know I had this great product and we launched it and we got to about 2 million of ARR and because I was stubborn and I love Jason Freed I didn't raise any money for it and Aana Monday.com Reich all these other guys raised $30 million and they could basically compete with us they could offer a free product that was frankly better than ours very very quickly and I realized like I was like

a sailboat compet competing with with uh motorboats like there's just I can't win the race. And I think that same thing happens in any competitive environment and you know I used the example uh uh when we were talking earlier of like you know restaurants are not a good business not because selling food is a bad business but because of competition. Mhm. Everybody wakes up every day like or sorry thousands of people in your city wake up every day and go I would love to own a cute cafe or start a restaurant because it's like a

thing that just is appealing. It's kind of exciting and um so there's a lot of competition, there's a lot of pricing competition and you end up with 3% margins. So it's a lot of work for a very small amount of money. On the flip side, very few people wake up and say um I want to spend my life imbalming and burying people. uh not that many people say, "I want to start a funeral home." Yeah. So, uh if you own a funeral home, it's an amazing business. You can charge a really uh solid price and

you don't have that much competition and there's only like two competitors in your city or whatever. So, you have 30% margins. And I think software has been a lot like that for a long time where um you know there's all these niche software businesses where venture doesn't compete, right? Um golf course management software, funeral home management software, um you know, just choose any industry and there's one nerdy guy who his his father-in-law ran a funeral home and he was a developer and so he got lucky that he had this insight and he made the software.

Now, there's so many business owners that have the idea for the software, but they don't have the son-in-law who's a developer. And so, they never create the software product, and they all just pay this guy a lot of money. He wants $10,000 a year, he gets his $10,000 a year. But usually the software is not that complicated. And the barrier has simply just been a human capital allocation, right? There's only so many developers in the world and they want to go work on the cool stuff. Well, now with anyone who's even remotely savvy and owns

a business can decide tomorrow, you know what? I'm going to roll my own and I think other people would like this, too. So, instead of charging $10,000 a year, I'm going to charge $5,000 a year. And then another guy comes along and says, "I'm going to do it, but it's going to be better in this way, and I'm going to charge $1,000 a year." Right? And now very quickly the whole market shrinks down to what they can charge and the margins uh margins erode. And so I think AI just does that in so many industries

like right now it is software but I think it can do that across the board. I think that as as people are reallocated to other jobs. So for example like if there's 30% fewer lawyers where will those people flood into? they're going to flood trades, brick and mortar businesses, all sorts of other exogenous competition. Yeah. Have there been any examples of a SAS business that was really, you know, like the funeral home software example, um, where AI has just made it so much easier to launch competitors that you've seen in the last couple of years

where like this used to be a great business and now there's just 10x the level of competition. Well, I think like anything that's a database, right? Anything that's like a database with a UI over it, right? And it's not that it's happened, right? Don't get me wrong, like, you know, Salesforce is still a good business because people are trained on it. Um, if you have a network effect or you have a really great brand or you're the default, I think there's a lot of value in that in the same way that like Kleenex and Band-Aid

and Tylenol are still good businesses, but um I think it's more like the steamroller is coming. Um the analog or the metaphor that I use is uh you're building sand castles on the beach and previously a lot of those businesses were way high beyond the tideline and now the tideline is just moving in way faster and in a very different way than what we've seen before. And so going back to my starting point of you know investors are just predicting how long can this business go what will its margins be how long can I assume

that it'll exist and how much cash flow will it produce. I think it's just way harder to predict. Like when we look at software businesses now, we are being far more conservative on how we underwrite them. Stuff we we would have jumped at two or three years ago, we're now kind of like, hey, we're going to pass on this, right? Do you think there's anything that AI or in this new world like that if a business has certain traits, it's actually more appealing now? Like I talked to Jason Yanowitz about this and he he mentioned

that proprietary data is actually more important now than ever before. Are there things like that that you're seeing in businesses that make them more attractive? Well, I think proprietary data is valuable if you can do something with it and if it's valuable. So my family's history data is like Yeah. Well, not only that, it's like the models, the question is like the models only need so much data. So like, you know, to dumb it down a bit. So it's like the models need to ingest all this data to learn skills and have understanding of things.

Mhm. Um let's say that you have a bunch of data on I don't know uh patterns of people visiting a bakery or whatever. Is that valuable to the model? Does it matter? Will Open AAI pay you for it or is it data it can just get free somewhere else? It might be proprietary, but it's not necessarily something that's unique or valuable or that someone will pay a lot of money for. Um and I think data increasingly is becoming commoditized as these models get so big. Um, unless you have a very very unique data set like

Reddit or something like that. I mean, I think our data set at Letterbox is an interesting example of that because you really only have you have IMDb which has all these ratings and reviews for the last 30 plus years of every film. So, that's incredibly valuable, but I assume Amazon's going to keep that one. Um, other than that, it's like, yeah, if you wanted to get broad film data, where would you get it? Right? So, I look at letter box and I think, okay, that's really interesting. Um, but as I've looked at some of the

other businesses that we own or that we consider buying and we evaluate the data, uh, and I've talked to people at OpenAI and Anthropic and stuff, I don't know that that's necessarily that valuable. What I think is more valuable is, uh, a brand and a network effect. Yeah. Right. So, you know, using the letterboxed example, um, AI tomorrow can make it really easy for you to create letter boxed, you know, copy a clone of it and have all the same features as the same. social network, but if you have no users, why would I ever

go there, right? It's like you're trying to start like, you know, why would you use Visa when you can use my special and it doesn't work anywhere and no one no one knows it and trusts it, right? So, I think that network effects are still very valuable. Um but it's yeah it the the the I remember um maybe five or six years ago I got to have dinner with Charlie Mer for the first time and it's so funny because over and over and over again he just we would be talking about investing he just keeps

saying it's hard you know he's just you know he's so funny he's old he's like 97 years old and he just say it's hard these days you know it's just hard and I was kind of like no man like for us like this is easy like we're just taking like we're finding all these amazing deals and amazing businesses and I think it was because um a he's you know older and been through it all but they're operating at such big scale and they can only look at certain things and I realize now in retrospect I'm

like oh no like we were just in the easy zone like for them the easy zone was like the 1950s and60s and 70s where there were these amazing businesses that were not only exceptional but they were trading for like half of the cash in the bank and then the market got more efficient and I think what's happening right now is just a more efficient market for software, technology, businesses, that kind of stuff. And so, you know, it's not like there's not incredible investments out there. It's that we just have to be so much more frosty.

So, I'm I'm now the old man. I'm I feel like the old man at the dinner table now. You know, saying it's hard. Yeah, exactly. Which markets are two two questions. Take take both of them if you will. Um, at the larger scale, tiny is that now? How much harder is it to find those good investment opportunities? And then I'm going to throw another one at you. um what markets do you think are still inefficient or where can you try and find those edges? So, we can still find wonderful businesses, but they're really um so

we we kind of we kind of do three different types of acquisitions. One is um distressed or cap table issues. So, for example, um we bought a business where they had raised $50 million. They'd shot for the moon. um they had gotten to about $10 million of ARR and then something about their technology was kind of disrupted but not completely and so they couldn't raise more money. The founders went off and did something different and the VC firm was there like well what are we going to do with this? So we bought that business for

500 grand, right? Wow. And 10 million of AR but every single month on the P&L was losing I think it was losing a million dollars every month. So you look at the P&L and you're like this is a disaster. We bought the assets of that business. We ran it uh with a I think a four or$5 million P&L instead because we didn't need the office. We didn't need all the you know they had army of people and stuff. Um and we were able to run it incredibly profitable. But that is what Charlie Mer would call

a cigar butt. We found a cigar butt on the floor. We took a puff. You and you know I think we did a good thing. We kept the business going. We kept the customers happy. But ultimately that's a business in decline. Um, you know, we we always joke it's like a a sinking oil tanker and there's a million dollars of oil, but you got to go do this big scary mission to do it, right? It's like only worth it once in a while. In the middle, you have a good business, but um maybe not run

exceptionally, right? Maybe the founders's a bit tired or had a co-founder dispute or something like that or or it's just not there's a couple things that could be done better uh in the middle. And then on the the best side is those dream businesses that come along every three to five years. Those are the letter boxes, the dribbles, the arrow presses, the truly exceptional business with a real moat. And um I think those are still going to come along every 3 to 5 years, maybe maybe more frequently than that. Um and we're seeing a lot

of the distress side. I think the AI world has created a lot of distress and we're seeing a lot of very interesting businesses um where we can actually model okay even if AI disrupted this tomorrow it's going to be this decline but the interesting thing there is there's just such an incentives mismatch where the venture investors they just view it as like garbage they want to get rid of it zero the founders don't realize that they're millionaires right because if they just get the if they get the venture capitalists out they can just run it

profitably and So often we'll partner with the founders and run it profitably and you know everyone kind of wins. The VCs get their write off and they don't have to deal with it. The founders get to make some money out of it and we get to make some money too. Um and usually we can not in all cases but we can usually keep all the employees and stuff depending on their structures. Usually it's like wasteful spending on SAS or offices or silly stuff. So like vendors as opposed to people. Exactly. Um but the the the

middle is getting harder. It's harder to find those those kind of businesses where we've got to we've got to pay up, you know, a higher valuation, but it's we have to be able to like pull some levers and be able to predict it. I'd say those are just less predictable. Is it cuz there's less or that just pulling those levers you're less I just I just can't bet I can't make the bet, you know, I can't make the bet this business is going to exist in seven years. Yeah. I can probably make the bet the

business will exist in 3 years and not that many people like to be clear like we've paid 20x multiples on businesses. I'm totally comfortable doing that if the business is truly exceptional. But a lot of these businesses are not that great. And what they're actually worth is a massive down round or way below what the founders thought they were worth. And so it's just hard it's much harder to buy those businesses right now. There's a lot of risk. More mispriced potentially as well. Totally. Yeah. So I think it is like being a public markets investor

40 50 years ago things are just getting a lot more efficient and stuff. Now you asked where are the opportunities still um the biggest opportunity in my opinion is relationships. So the best businesses we've bought have always just been someone that I know or I meet or I connect with and they go I want to sell to you. Um, and I think you you can't find that in a stock screener. You can't find that via an investment banker. Uh, that comes back to that whole idea of like one of the benefits of having this broad

base of friends and people that, you know, I know is just that I'll meet interesting people. And when you have a reputation for treating founders well and uh running their business in a way that respects their legacy and keeping it for the long term, you can actually get some exceptional deals. So when I when people come to me for advice about where to buy their first business, I just go, "Well, who who do you know that's like got a wealthy grandmother?" Like, you know, it's like, "Who owns like like I bet you that grandmother's rich

because she started a business or whatever and usually the grandkids don't want to run it." Or who's the person at the golf club that you used to caddy for who always liked you and they're turning 75? or who's the founder you met at that meetup three years ago that bootstrapped their business and every time you see them they look a bit stressed out you know cuz keep looking worse and worse yeah like Chris and I have this whole um this heristic where it's like every founder in year one is like I'm going to run this

business forever every founder in year five is like yeah like you know it's different now but like I still really love it I'm learning a lot and then year eight they're always just like I hate my life and I want to relax and you know my wife just wants us to be able to buy a house and whatever. And so like really what we're doing is like we're therapists. We're like expert therapists. So like talking to founders and I know because I'm I'm that right? Like any business I've ever been in. It's like often I

get go through those same cycles. And so I'm just looking for okay this person has a problem. They're eight years into their business. They've got $50 million of equity. Um they know that if they could just sell $20 million of it, they want to keep running their business. They just want to be left alone. they would do it if they just knew they could be left alone and have all these pressures, but they don't want to sell to private equity. They don't want to raise from venture. We're trying to meet all these interesting people, evaluate

and then play therapist once in a while and go, how do we structure a deal where everybody is happy, right? Where this the transaction on all sides of the table is positive. That's so funny. You should start an index or like some sort of tracker that's like, all right, founder year started. Okay, it's eight years now. We got to we got to hit him up. It's so funny. Um, you know, I mentioned Brent Bishore. He invited me out to speak at he does this conference every year in um Columbia, Missouri. And he goes, I want

you to tell me like what's the secret sauce like you know everyone knows the tiny story and you know you guys must have systems and all these like cuz I think he's like probably got all these systems internally and like how he tracks they they had this thing where they would like do founder events and then track the founders and stuff and like keep t like basically a CRM of like opportunity and I I was such a let down on stage cuz I was like no like you know when we bought letter box I wish

I could tell you that like you know I had I've been tracking the company and I had pitchbook and all this stuff, but in reality it was I uh I was a designer, you know, back in the day and I would go to I think it was at South by Southwest or no, it was at XOXO, which was like this cool designy kind of conference in Portland. And I met Matt Buchanan who at the time he's this guy from New Zealand and he's running an agency and you know we had a beer and he's a

nice guy and we knew each other from Tumblr and we liked each other's stuff and reposted it and um didn't think anything of one another. were just two guys on the internet who knew heard of one another. And my brother is a um he's like a filmmaker and he loves movies. And so he's always he'd always talked to me about letter boxed and to be honest I was kind of like oh that's cool for like nerds you know it's like like I love movies too but like you know it's kind of it's like a little

nerdy community or whatever and and you know I but I started using the app and I was like oh this is cool but I didn't know how big it was. I just started following what is my brother watching and stuff and liked it. And then I went to New Zealand for a conference totally unrelated to work. It was actually like a kind of like a um it was this totally random conference out in the middle of nowhere in New Zealand. And while I was there I was like, "Oh, I'm in Auckland. Like who do I

know in Auckland?" And so I started looking through my Twitter and I was like, "Oh, that Matt Buchanan guy I met all those years ago." So, we go we go out for coffee and we're talking and you know he makes some I was like what you know what's uh what's your plan like you know um he's like well we started this letter box thing and he's telling me about it and and then at one point he goes you know it's gotten to like 12 million users like and I was like whoa record scratch like can

you just go back to that how sorry how how many like what like and then I was like wait how big is the business he kind of all the things they were doing. And I was like, "Oh my god." Like, "Dude, this is like an amazing business. Like, what's your plan?" And he's like, "Well, I don't know. Like, we you know, we've been doing it for 10 years and like maybe we'd maybe we'd sell, but like we still really love it." And I just said, I was like, "Well, how much would you want if you

sold it?" And he's like, "Oh, I don't know." Like, and he's like threw I was like, "Tell me like your craziest number." He tells me the number and I'm like, "Okay." Like crazy. Do you want to sell like how much you want to sell? Like 40% 60%. Like I'll do that. Like literally I was like we could do this in like two months. Like do you want do you want to do it? And he was like whoa like let me talk to my wife. And so he he went and he talked to his wife and

his co-founder. And it hap it just so happened that when I was flying back to Vancouver he was flying to New York to go to a film festival. And so we met at the airport and we literally literally sent him I think the next hour after I sent him an we talked through all the details and we got it all negotiated in the Auckland airport. And so you know I wish I could tell you that there's some like amazing formula but it's like I don't know how and this is why I'm okay to share it

too. It's like how do you copy that? It's like you can't all these random connections and like it just so happens that I'm a founder and I know all this stuff like I can have that conversation with him and put it all together. So yeah, there's no system. Yeah. But you are the system. Sure. Sure. Yeah. Me and Chris and some of the other guys, right? Yeah. Are there is is that the benefit of being as curious as you are and just wanting to meet as many interesting people as you do want to meet? Well,

I think um Yeah. Like I think what I've I actually it's interesting I was getting interviewed at a different one of Brent's conferences by Patrick Oanaughy and he he goes um you're like you're not like the usual private equity guy you're like you know usually they have a formula you're like some random artist who's just kind of like abstract painting and like you know and it's kind of true for me it's like I meet someone I'm interested in or actually before that it's usually um like you know if we go way back I was a

barista back in the day And I easily could have seen myself in a different life just starting a coffee shop. You know, I love coffee. I love making it. I love drinking it. I love talking to people. I'm an extrovert. I love being a barista, but I didn't like waking up at 5 in the morning and mopping floors and making 650 an hour and all that stuff. But I could easily have this alternative life. And so my whole life, I've always had this affinity for people in the coffee industry. And I've always followed what's going

on in the coffee world. I've always bought all the new cool gadgets and gizmos and I watch all the James Hoffman videos and like I just you know my YouTube algorithm is coffee and you know one morning I was making an Aerop press cuz I love Aerop Press and I looked down at it and I was like who owns this and I assumed it would be some like you know horrible private equity firm or whatever and uh turned out it was still owned by Alan Adler the original inventor. And so, you know, I was like,

"Well, whatever. I'll send him an email." And so, I sent him an email and he's like, "Hey, um, I'm hard of hearing, so you got to fly down and meet me." And so, it's like that is so random, right? And that's not a, you know, letter boxed is random. Um, dribble is random because I was a designer. I used dribble. That was how I found all my work. And I was just a fan. And you know, I talk about it in my book, but like I worship Dan Cedarhome, who's like the designer who um did

dribble, but the only reason I know him is because when I was learning design, when I was learning how to code, I bought um CSS for web designers, his book from like 2005 maybe, and I was obsessed with like the way that he did drop shadows. So, it's like that led to us buying dribble for $10 million 10 years later. Like it's just these are all very random, you know. You can't connect the dots looking forward. No. Have there been other things in your life outside of investing and business just in general where you know

you had those little moments that all stacked up in retrospect like ah that's that's how I got here or Well I think um I mean you know luck comes to prepared mind right like I think um in building the opportunity surface area and then having all the mental models so that when you see the thing when the opportunity comes to you you're mentally prepared to go oh this is one of those, right? This is a big swing. And so because I'm kind of an anxious person, I'm an anxious planner. And so whenever something bad is

I'm worried about something, my way of coping is to prepare. So um you know, for example, like this, well, this isn't really a bad thing, but when I sold my first business, I was really stressed out because suddenly I had this money and I didn't know what to do with it and I felt like an idiot and I was so scared that I was going to like blow it or do something stupid. And so I started reading every book I could on investing and Warren Buffett and all that stuff. And as a result of that

like maniacal preparation to not go bankrupt. Yeah. I ended up getting into Buffett. And then that propelled the rest of my career which you know if you'd sat me down back in my barista days and said um flash forward 20 years you're going to run you're going to be a finance you like if you really make it like if you say the cold hard facts it's like you're going to be a finance guy and barf. like I would barf. I would not I no like and so yeah, it's just this very random collection of preparing

and then being propelled. And the only reason I was able to buy dribble was because I'd read all the Buffett stuff and I understood network effect modes, right? So it's just I don't know. It's the Munger calls it like the the lattice work of mental models. You got to read endlessly so that when you see one you're ready. Yeah. Do you think being offline has helped with that as well? Like being less online, like being able to build up those latest models as opposed to just seeing something new every day, adopting it, and then releasing

it. Well, I think it's um one thing I've tried to do is not consume um what I call tickers. So, a ticker would be um Trump said this, right? Trump, you know, this happened or um you know, it's information that doesn't have context or story. And so what I get a lot more value out of is like how do I zoom out and how do I read a full story? So, a full story might be um here's a you know 1800 steel tycoon who grew a massive business and then failed or or he you know

uh had a horrible miserable life or um here's the story of like you know I don't know just b businesses like I want to read the whole story or even zoom out even more and go like um there's this book I love um by Will and Ariel Durant called the lessons of history and it's this very small book and it's basically saying like, you know, we've had a I think they had like a 50-year career as historians, and that book was the summation of everything that they had learned about the patterns of humanity. And so

for me, um, you know, instead of reading news, for example, like I watch, uh, Ken Burns documentaries a lot and I watch the the Ken Burns Vietnam documentary. That one's that's unreal. It's it's intense, horrible, depressing, but really really well done and fascinating in it. Um, you know, a lot of it takes place in the 19 late 1950s, 1960s, 1970s. And that was really a period where America was falling apart, right? You know, there's there's riots in the streets, there's civil unrest, you've got the hippie movement, you have, you know, weird like socialism and communism

ideas, and then you've got the old guard and, you know, all this conservatism. Um, and and you know and even like Nixon and Watergate and stuff and so having watched that and um and realized that okay we went through that period and then all those people all the hippies grew up and now they're the boomers or you know the boomers parents or whatever uh and and that all worked out fine you know yeah they were like uh you know free love and all this other stuff but ultimately they kind of got their their stuff together

and organized the world um and I think people have funny concerns about like Jen and Z or Gen X before that and us before that and whatever. Um, and then also people feel like the world's falling apart and it's like, well, if you talk to someone in 1963, they would be like, uh, oh my god, the red threat, communism, you've got nuclear war, um, we've got civil unrest, blah blah blah blah. Like, the kids are all doomed. and and I'll never forget I read this book um Robert Green has this phenomenal book called um the

laws of human nature and he talks about the the generational cycle that occurs and there's this great quote in it. It's like from it's like written on stone from like 200 BC or something and it's like some philosopher saying I worry the next generation is doomed because they are weak and and and so like for me spending my time on that gives me a lot of um calm seeing the chaos in the world today and going you know I think we'll figure this out and I think everything will be okay. Is it does it mean

I'm happy with it or complacent about it? No, but it does make me kind of realize like no, we're in a cycle and like this is normal. Like our society is in its teenage years right now and it's going to be dramatic for a bit and then things will cool down. It just gives you context. Do you also you apply that to like you know AI it's it's been out for like you know it's been out for a couple years now. People like should know it's changing the world and like that can be scary in

and of itself or it's disruptive at least. When you're investing do you sort of keep that mentality as well? It's like you know I'm here for a long time horizon. Let me try and place this in similar industrial revolutions or other technological changes. Um what kind of comparisons do you draw on when you're investing with you know technological changes like AI? Well, the AI one is so unique, right? I think um the way I'm reading a book by Stuart Russell right now who's a um he's a computer scientist, but he writes a lot about AI

and kind of control and governance of it. And the way that he put it was, you know, if people found out that there was an alien race that had sent us an email and said, "Hey, we're arriving on planet Earth in 2 years." Yeah. Right. Prepare yourselves. we would all be running around like chickens with our head cut off panicking and preparing the nukes and everything else. And I think, you know, AI could be that, you know, I don't know that it is. It could be that, you know, we just have uh little APIs that

can make decisions like where to put my emails and all that kind of stuff. But if AI actually gets to a point where it's recursively self-improving, we have a very different all bets are off, right? Um, and I think there's a lot of different ways that could go. And so I'm not a big fan of when people say this time it's different because usually it's not. But I think that this time is different. You know, I hate to say it, but I think this time is different. And I've spent um probably like 50% or more

of my time over the last year or two on AI. Um, really trying to get to the metal. Like I was at OpenAI two weeks ago. Um, I talking to people at Anthropic, trying to get into as many people as I can that are high up in frontier models and really understanding what's going on there. And I don't know that, you know, I don't I don't I think like it's very easy for people like that to get high on their own supply. Like you talk to any startup founder and they say, you know, we're going

to build the first trillion dollar company or whatever, right? Um, but what I'm hearing across the board from AGI researchers and people at Frontier Models is that this is inevitable that in the next two to three years basically we'll have PhD level intelligence across all realms of knowledge. And if you think about that, it's a little bit like finding out that, you know, you have a brain that's like a vinyl record and like, you know, digital music or Spotify is about to come out and like we're kind of going to be irrelevant in a lot

of ways. And so if you just think about the different worlds, so the one world where scaling doesn't work or LLM's hit a bit of a wall and we just have what we have today, that could be highly disruptive, right? because coding, you know, vibe coding and all the competition stuff we talked about earlier. That's just kind of table stakes. I go like that's probably that's reality and it's just about um the future's already here. It's just not evenly distributed. Alan K, like it's just that um self-driving cars, AI, there's going to be some disruption

and but it'll be incredible opportunity. I think it'll be massive human flourishing and amazing. There's another world where it gets to um you know PhD level but it's highly controllable and it's not self-aware and intelligent and all that stuff also amazing you know we can go and solve you know all sorts of physics problems and create massive technological innovation and cure cancer and other stuff there's another world where it's just totally uncontrollable and crazy and and I think any of those I think those are honestly the three scenarios that I see I don't know how

I don't see how it stops. Um I could see and most technologies do peter out but most technologies depend on human human linear thinking and I think this if it goes exponential that's the big question and I think that um they call it like fast takeoff. So it's like, you know, you get this crazy exponential curve. Um, and if that happens, like as an investor, there's really not much you can do other than maybe owning, you know, I was talking to a friend and he was like, you know, Amazon, uh, Microsoft, Berkshire Hathaway, own those

three stocks and just like that's your best bet and like but but you know, he was like look like we could be post capitalism, right? if there's just total abundance because of AI because none of us have to work, maybe uh you know, some weird alternative form of government exists and we all just hang out and play pickle ball all day. Like that sounds that sounds kind of nice. Um but yeah, that's that's kind of how I'm thinking about it. I and again I'm not um when I talk about this stuff I feel a little

bit like I'm um like a co researcher in 2019 seeing the readouts and I'm like oh like I'm not saying that's happening but I am saying like you know this could happen and this is a this is something that every investor on the face of the earth should be thinking about I think every human should be thinking about and I feel um yeah deserves a lot of thought um but I don't know there's that much to prepare for but the first one I talked about that you can prepare for that's kind of now yeah you

can just say like based on everything that exists and you just project that forward a little bit which of my businesses could be affected and how and how should I prepare yeah would that uh this is going to be a bad question where people ask you like hey if you started again today would you have started an a would you have started an agency now knowing that well I think um you know when you start you have nothing and all you have is um you know what you're capable of doing and selling your time for.

And I think that an agency I always talk about um you want to you want to build your launch pad before you build your rocket. Elon Musk had some pretty boring businesses. First he did like payments or something. Even before that, the directory, I think. Um yeah, he he was a directory and then he did um Zip. Yeah. Was Zip 2 and then he did PayPal. And those, you know, they're very innovative, interesting businesses, but they're not rocket companies. And then he what I call build the launchpad, right? So that gave him 200 million to

go build the launch pad. Then he went and did all the crazy stuff and changed the world. And I think uh on a more humble scale, most people should focus on getting $100,000 a year, which is the launchpad. The most important thing is if you're an entrepreneur, and I don't think everyone's an entrepreneur. only if you have the itch and you, you know, revile being told what to do. Um, very bad employee. I talked to a lot of, um, young people and they say something like, uh, well, you know, like my, my mom is an

entrepreneur and like I kind of think I might want to do it, but first I'm going to go work at Deote. And I'm always like, if you even say that, like, no, you're not an entrepreneur. Like, I'm sorry. Like, don't do that. Um, but so if you are an entrepreneur though, I think it really comes down to, yeah, what's the easiest way to make $100,000 a year? Mhm. And there's there's good ways and bad ways to do that. You know, the worst way is you just sell your time and then you have $100,000 a year,

but you don't have freedom. I think an agency is great because you can sell time. Um, you can build systems and hire other people to do some of the work you don't enjoy, but it's hard because it's very up and down and variable, as you know. I know you own an agency, too. Um, but it's very fast. You know, within a year, you can be making a million dollars a year if you do it right. Right. uh if you build a software company, lot of upfront investment unless you know how to code and do it,

maybe you can now with AI. Um bit of a slower burn, right? Um and there's a million other things. There's affiliate marketing, there's email newsletters, there's, you know, we could go down the list. I think all of them have pros and cons. And ultimately, it just comes down to what is your skill set, your natural uh tendencies, what's your affinity? And then within that, you know, if you think, let's take the agency example. um why was I able to build uh you know a multi-million dollar agency over the course of five years where many people

don't do that? Most people have very low margin agencies that don't do work they're excited about. And I think the only thing that I did and it was totally by accident was I was making like local websites for like you know small little companies like pulled pork barbecue joints and like you know I did like just random projects and I got so lucky that I found this um job board down in San Francisco for freelance jobs that all the startups were posting on and they would say something like um hey we need someone to contract

for us to do this coding or build a website or whatever it was and I just started emailing all of them and then that got me into this circle where there was gold in those hills. Those were people that had raised millions of dollars that were cost insensitive. So, and they were doing exciting work. And so, I was getting to do really cool work with really interesting people who are cost insensitive. And if you're selling to a customer who's price sensitive, right, that sucks, especially if the work is boring. And so, it's like when I

talk to people and they're like, um, I'm building software for elementary school teachers. I'm like, "Well, that's really sweet and I'm glad you're doing that and like that's great, but like I want you to know it's going to be a slog because most elementary school teachers don't have budget and they're personally not known to have a lot of money. So, you're selling to someone that is naturally going to want to pay you a dollar. If you took that same level of work and intelligence and time, and you just found a niche like funeral home software,

you could probably charge $10,000 for that same software that a a teacher would only pay $1 a month. Yeah. Um, so I'm a big fan of once you find your your niche, you go find where the money is. And I'm a big fan of um Charlie Mer used to always say fish where the fish are. And the idea there is like don't go to the overfished pond. Go off the beaten path and find your own pond. And I think that is the key. Like you could even like when people say something like it's so funny

people be like you know our agency is dead or um you know can you still make money doing email newsletters and it's like well yeah like there's money in everything. So like if you do an email newsletter maybe you do an email newsletter for farmers in Texas who need a certain type of crop data that's highly valuable for them. Well that's a good business. But is it a good business to do an email newsletter for retirees to share gossip? It's like no, you can't monetize that, right? It might be fun. Sure. Totally. It's a fish

with a fisher. And and the the sad reality I've found is like the to go back to my restaurant analogy, like the areas where you can make the most money are not the sexy ones. Right now, are there businesses like Dribble and Letterboxed and Aeropress? Yes. But you have to buy them usually. They're hard to start. uh you can start them, but they're usually hard. The passion-driven businesses are the hardest to make money at because you'll have competitors, right? So, I'm a big fan of sucking it up and doing the thing that you're not excited

about. And I've realized like most great entrepreneurs, whether they're selling paint or Ferraris, they'll get excited. they can get excited because they love that they're making money and they love that they can tell stories and you know this certain paint is non-toxic and here's why that's important for your family and this color evokes this emotion like you you just find people that have passion and I think um go to where the fish are. Yeah. If there's an entrepreneur listening to this and they feel like they might be in that boat, like what questions could they

ask themselves where it's to realize if they're in that situation or not where they should be doing something else or if they're running a passionled business or you know what Yeah. What questions can you ask yourself? Well, I think um one of the biggest problems is that the one thing that worked really well for me was I was broke and my parents were also broke. So I had no there was no out, right? And so every month I had to make money and I had to have profit because I had to pay my rent. And

that enforced a discipline of profit and understanding a P&L. And when I say understanding a P&L, profit and loss statement, I don't mean that I did an accounting degree. I mean I I would go how much money came in, what were my costs, how much did I pay everyone, what was left over, what's in the bank at the end of the month. And I just find most entrepreneurs, they do two things. They don't know that number clearly. Like when I ask an entrepreneur like, "Well, how much did you make last month?" And they're like, "Well,

like my bookkeeper is not quite up to date." And I'm like, "No, like you need to just know that number. You need to be frosty." Because that's your money, right? That that's literally your bank account. Um, and then the other thing that they often do is they don't pay themselves. So, I've met so many entrepreneurs that are millionaires, they don't realize it because what they do is they take, let's let's just use a simple example. Let's say that you have an agency where um you make $100,000 a month of revenue, you make $25,000 a month

of profit. I because I had to pay my bills and because I was selfish, frankly, and I wanted to go wanted to go buy stuff and have a nice life and all that. You know, I grew up never having money. I wanted to go enjoy it. And so, I would just pay myself 25,000 into my personal bank account and I go do whatever I wanted. But I know a lot of entrepreneurs, they take the 25,000 and then they don't realize they can dividend it to themselves. And so they keep it in the bank and it

creates this psychological effect of, well, the money's there. I need to spend it on something. So they start saying, well, I'm going to buy a fancier office or oh, I'm going to, you know, the classic is like they run an agency and they say like, well, like, you know, we want to start like uh a lab. You know, it's like we're going to start building like hardware products or whatever. And I'm not saying those are all bad. Like I definitely did some of that and did some R&D, but first and foremost, you got to pay

yourself because when you pay yourself, no matter how crappy your month was, like no matter how many planes you got on, how many annoying sales calls, how many people problems you dealt with, you know, you come home to your beautiful apartment and you feel a sense of winning, right? You feel like, you know what, like I'm going out for a steak dinner with my girlfriend tonight and that's my my pay for doing this. And I just think a lot of people for some reason they just don't do that. Um, and there's this amazing book called

Profit First. Uh, I read it probably 5 years ago, but it describes this concept in detail of how to do that. And I just did it I did it naturally. Um, but if so many people just they're they create these weird again prisons of their own making of Yeah. Is is that is that the book where they say if you madeund like you're going to make 100 grand just take 60 grand out because you want to take 60% profit margin then figure it out and figure it out and it's like it forces you to just

figure it out and make it possible. Yeah. And uh I I love I have a friend my friend Jonathan Becker one of my best friends he runs an agency and he was doing this exact same thing. He would have um four bank accounts I think and it was like you know there's the um operation or the payroll bank account. So he's like, "Okay, payroll is this, um, taxes are this, and then the Jonathan bank account, and that's profit, and it's just always split." And he actually would keep it in different banks. So it' be like,

"The operating bank is Royal Bank of Canada, but all his personal profits go into BMO." And he doesn't look at it. It's just off off of his mental radar. And again, it's like the psychological effect of um, in studies when you eat off a big plate versus a small plate, you want to eat off a small plate makes you more efficient. I love that. Are there any I want to sort of I know it's taking up a lot of your time so no I'm happy to keep um are there any any other frameworks like that

profit first or books that you found to be really helpful thought you know tools to to sort of get to the outcome you actually want I think um the E-Myth by Michael Gerber which is a bit cheesy but really really great um it's the the basically a lot of what I was talking about about um not working Uh theam the the story he gives in it is a hypothetical. He says um you know there's this woman who loves baking pies and so she starts her own pie shop. That's her dream. But one year later she

is staying up until 4 in the morning baking the pies. She is working the till covered in flour. She's not sleeping. She's miserable. And it's all because she hasn't delegated and she hasn't built systems. And so the whole book is really just how do you take your business from working in your business to working on your business and how to build a [Music] machine thinking of your business as a machine that you are the engineer of versus a cog within is really critical. Um getting things done the productivity book I think is really important. There's

a a book I love called How to Get Everything You Can Out of What You've Got by J. Abraham. Okay. Um it's it's just kind of a a manual. It's like a list of every way to make money. So it's like um you know, for example, it would be like if you're a dry cleaner, um what things are you forgetting that you could do? So for example, can you um create tiered pricing so that if you want non-toxic cleaning, we charge more. Can you sell hangers that are wood because people don't want to bring home

the metal ones? Can you uh create a referral program where whenever someone sends you a referral of a new customer, you give them a free dry cleaning, whatever. It's just all the things that most entrepreneurs don't realize are possible in a business until they've read a bunch of books. Um, so I love that as just like here's the menu of like all the way and choose this and add this to my business. Mhm. Um and then I'm trying to think of other more and then I mean the two that I would really recommend um one

is uh oh my god what am I had it ADHD brain. [Music] Um what is it called? Um oh my one of my all-time favorites I mentioned it before is the laws of human nature by Robert Green. And it's basically uh Robert Green has such a wonderful format because he tells a story. So he'll tell a story of a famous narcissist. I think he uses Richard Nixon as the example. He says this is the story of Richard Nixon and here's all the behaviors. And then the next half of the chapter is explaining here is how

a psychologist would um consider the behavior of Richard Nixon. His mother treated him this way. He had this disorder. this is what this is the type of personality this is and this is how you deal with it, right? Or another example could be sunk cost fallacies. So it's someone in a structure loses a bunch of money, they do this irrational behavior. And so again, it's a manual of all the ways that we warp our thinking, right? Um I love that one. I also love there's a famous talk that Charlie Mer gave at Harvard in 1995

called the psychology of human misjudgment. It's a very scratchy crappy recording. You can listen to it on YouTube. Is a Stripe book. Does that have I think that has a name? No, it Oh, yes it does. It does. It has a transcript. I would just listen to the audio recording. Like what I did is I just every time I drive to work for like a year, I just listen to it on repeat to get it into my head. We also made an animated version. Uh if you Google or if you go on Vimeo and you

search Charlie Munger psychology, we made like an animated version that's a bridged. Um, and then on the Charlie Munger front, I think the best Charlie Munger book is The Tao of Charlie Munger by David Clark. And it's just a collection of quotes. And basically, it's here's the quote by Charlie, here's what he means by it, and here's the history. And there's so many books on Buffett and Munger. Um, but I actually found that one to be probably the most impactful. And again, great audio book. I just listen to it on repeat. Um, I think like

Buffett and Munger are a great place to go whether you're an investor or not because they're basically um just incredibly wise and incredibly broad. And so by learning their ideas, you actually get exposure especially Munger you get an exposure to a lot of ideas in business, biology, physics, all sorts of places. They're so fundamental that you can like I mean invert invert invert like you can apply that to anything totally as well as business. That's awesome. Is there anything else you think we should we should talk about that that um they think could be valuable?

Is there any other stuff that you had on your list or Dude, there's I I could talk to you for hours. Like we could go we could go deep. Let's Yeah, I mean, ask me a couple more. Let's Yeah, I got to eat lunch at some point, but All right. You sure? I'm going to interrogate. No, no, happy to. Awesome. Um I mean, that's like a first class education in business and maybe even, you know, in life. Are there any funny like um you know like to the invert example for Charlie Manga? Do you think

there are any frameworks that you've learned from those that have been applicable both to business and in life? And like do you have any examples of how you've you know implemented those? Yeah, I mean um I read about inversion by reading Munger and I started thinking about applying that to my own life and Chris and I started this annual ritual of writing out what we call anti- goals. And it's basically like it's not about business necessarily. It's like what do we not want our lives to look like? So we do a bit of an analysis

of like okay um we have these we have these goals of like you know I want to I want to make sure I have time with my kids and I'm home for dinner every day. I want to wake up and look forward to every meeting. I want to know that um every person that I have running a business or I'm doing business with doesn't give me any kind of creepy crawlies. You let them step babysit your child. Yeah. Exactly. Oh yeah, we use the heristic, would we let this person babysit our child? And if the

answer is no to any of those, we try and think about, okay, how do we change our trajectory on those things? And so very simple methodology. I actually wrote a post on Medium. If you Google Medium um anti- goals, it should pop up. But um I found that incredibly incredibly valuable because so often, you know, you hear people like basically guess at what makes them happy. They'll say like well like it's like what do you want out of your life? It's like, well, I want to go to university and I want to um build a

big business. I want to do all these things, but they're not thinking about like, well, why? And they're guessing how that will make them feel, but everybody knows what they hate, right? You know that you hate getting uh low sleep or you hate uh traveling or you hate uh not eating well or whatever it is. And so, come up with your own anti goals and design your life accordingly. Yeah. Do you think that when you're trying to make it and you're trying to grow your trying to grow your business that you can do both, you

know, have a great dayto-day life and like that there's the idea that it has to be um this or that and not and? Well, so um the like outrageous thing that I always say is like I've worked 4hour days for 20 years and I've built a big business. Now, have I, you know, am I always kind of working, right? Um, am I always thinking about my business? Am I always texting, thinking about it? Yeah. But I'm a big fan of like, you know, look, I worked from 10 to 2. Now I'm going to go play

pickle ball and then I'm going to go hang out with my kids and have dinner and I'm going to sleep, you know, 9 hours or whatever I need because I recognize that I really don't have that much juice. And are there times where I work more or less? For sure. But for me, I haven't found the need to do this crazy hustle culture stuff. Like I don't understand like to me like being a venture capitalist or being in private equity is like the chillest job. Like most of what you should be doing is like reading,

thinking, and then occasionally acting. And I think most of it is productivity theater, right? I think like you know ultimately um there's different ways of doing deals for example it's like um when we buy a business usually it's like um okay I just had a founder email me he goes uh I want to sell my business but I don't want to waste a bunch of time and I said well I definitely won't waste your time if you send me an email and you just show me a table I want to see last 5 years I

want to see the revenue and I want to see the earnings I want to see your dividends how much did you guys pay out and he sent me that and he just sent This is still my inbox, so I haven't done this yet. But what I'm going to do is just say, "Okay, I think the business is worth this." Send an offer. And if he says yes, we'll sign the letter and then we'll say, "Okay, let's get this done." If he wants a bunch of legal work, sure, we'll do the legal work. But for the

most part, like, we could do the deal in a week. There's no reason why we have to do this nightmarish horrible process, right? And I think there's so much theater. going back to my experience of selling the business like selling the business took 8 months. There was insane 30 hours of meetings and um you know like they dragged out the negotiation. They renegotiated multiple times. They you know added all these legal terms. They wanted me to get life insurance. They wanted me to sign indemnity. Like you know all this stuff. And you know, Warren Buffett

always goes like, look, if you're doing business with good people and you're good at assessing whether or not someone's a piece of garbage, then you don't need a contract or if you do, that's a problem, right? And so generally I I subscribe to that. And you know, yeah, when we do a really big deal, frankly, usually driven by the realities of being a public company or sometimes the founders just being like, "No, this is my nest egg. I need like all this legal stuff." It slows everything down. But I just don't think you need to

do a lot of this stuff. And so if you take a lot of that away, um, you know, the business I sold, it was like if I was buying it, I would be like, okay, like, uh, the business was in the Shopify space. I can look at the Shopify dashboard and look at the numbers. I can look at the zero account and see all the numbers. I can see the cash flows. I can see the balance, the I can see the bank accounts. Like, tick, tick, tick, tick. Um, now it's does this guy seem like

a piece of crap? Okay. And then it's being honest, not about let's get a big number to trick him into signing. And not not that they did this, but let's, you know, send a big number and then we'll get them to commit and then we'll grind them down and the whole process. It's like let's just send the honest number. Let's just say like what are your priorities? Cuz like for me, if they had just said or if anyone buying a business to of mine had just said like look, like we'll pay 20% less than the

other guys, but we're going to give you all the money upfront. We're not going to lock you in. There's no earnout. Um, and we're going to treat your employees well. And hey, look at our past and we're going to look at your past. You've behaved well in the past. Uh, we've behaved well in the past. Let's do business. Right. Like I just hate all the theater. Yeah. So, so TLDDR, yeah, by working with great people, um, and by building machines, I think you can definitely have a really amazing life where most of your time is

spent doing the things you love and you're only really working, when I say like working, I'm saying deep working like 4 hours a day, right? That's amazing. Yeah. I mean, that's that's the goal. Is that is the most important part of that two things? Is it identifying or being able and do you think you've I I imagine this is probably one of your strong suits identifying people and assessing people as well as assessing your own strengths and other people's strengths so that you can put those incentives in place so that you actually have a machine

and not just people sort of banging away. Totally. I think um people think like doing buying businesses or operating companies is like 90% like math and finance and I think it's about 5 to 10% math and finance. Like the math, my math that I'm thinking about is very basic and straightforward. It's actually 90% qualitative assessment of is this person somebody I want to do business with? Do they make me feel good? Right? Do they have a good pattern of behavior? Do I know people in common with them? Um, and then separately from that, it's evaluating

the business. Is this, and it's not something you can put in a spreadsheet. You can't have a formula for will the moat stake, will this business be competitive in 5 years? You get like an an error. No, I can't I can't formulate that. I have to actually just have this again the lattice work and try and assess. Right. Yeah. That's amazing. How do you go about is it really just as as simple as being someone like that and then just over time building up those rel relationships to to be able in a position like that

to to tap into people or Yeah. I mean like if you'd taken me when I was like freshfaced 20-year-old and you'd said go buy companies like I would have done it all wrong and I would have bought things. Well I mean if you look at how I allocated capital for the first couple years of my life. So when I first started making money, I um you know, I bought some stuff, I realized like, okay, like I don't need another car or whatever. And then I was like, okay, um I like starting companies. That's really fun.

And I like solving problems. And so I would just again be in the shower and I would think, oh, um I like to DJ. Um you started a DJ. I should start like an online DJ school. And and I wouldn't have the filter, though. So I would just start it instead of doing what I do now which is I have the idea it goes through a filter and the filter comes from experience and reading and it says oh that's a bad business don't do that and so if you look at the businesses like I started

like a you know online DJ school I started a pizzeria I started a skincare company that went nowhere I started a cat furniture business like all these really really horrible horrible businesses where I lost all sorts of money right um that but that is the world's best um university for what is a bad business and why. And so I think you kind of have to have that framework of experience. And also I don't know that you can really assess good people until you've dealt with bad people. Like I've had some of those experiences where I've

been defrauded. I've had people lie to me. I've had the creepy crawly feeling with people and not trusted it and thought, "Oh, that's just, you know, dismissed myself." Um, so again, it's all a culmination of experience. You can't, Warren Buffett puts it so well. He goes, you can't be a good investor without first being a good business person. And if you're a good business person, that makes you a better investor. This is a synergistic relationship. Yeah. Do you think it is just because you just did those things and got that experience? And I think you've

called it putting forks in electrical sockets. Um, that, you know, builds up that experience that you're just going for it every time. Like in retrospect, would you still would you have started investing in businesses earlier? Uh would you spun up more businesses or less businesses with the cash flow you guys had or Well, I think it's like saying um you know, if you go back to 2012, would you invested in Bitcoin? Like everyone's going to say yes because they know now Bitcoin worked out well and everyone had the thought, should I buy Bitcoin? You know,

I um I remember me and a friend got excited about Bitcoin and we started uh we we were like, well, this Bitcoin thing's crazy, but let's sell pickaxes to gold miners. let's get a Bitcoin ATM. Yeah. And like it was a kind of a disaster. It was kind of fun, but you know, we lost a bunch of money doing it. And yeah, in retrospect, I was like right about the thing, but I didn't do it. But it's all it's also possible that in a counterfactual universe where Bitcoin didn't go or we were doing Dogecoin or

Litecoin or whatever, right? We just picked the wrong one. We did do the right thing. So, so yes, of course, with experience, would I go back and do things differently? But I think mostly it's what am I going to do going forward? to understand what the best ways to say yes are. Um, so like even when I'm doing venture investing or anything, the only reason I can now assess a good venture investment is because I've lost tons of money on all sorts of duds. And often it was stuff like, um, wow, I love this idea.

The founder I don't love, but this idea is great. Whereas what I've learned now is the founder is great. Everything else will be fine. Even if the idea is terrible, it's downstream. Um, so so yeah, it's all experience. Yeah. Is that I mean you still launch a couple of businesses every year now I think like maybe two or three maybe more. Uh do you do you now use those different frameworks when deciding on how to launch those or who to launch them with or what ideas? Yeah, I mean the biggest thing is realizing nothing will

go anywhere if I run it because I've got a day job, right? So the way I look at it is um my day job is running tiny. Um that's where most of my net worth is. My um my hobby is venture investing and starting businesses and I mostly do that because by venture investing I get exposure to interesting young entrepreneurs. I meet interesting people. I sometimes meet people who if the business doesn't work maybe we can buy it or partner with them or something like that. Um and there is something about just staying fresh in

that way. Um on the business starting side that is a chance to use the tools. Yeah. So for example like I just built a I started using chat GBT to like dress better. So I basically tweeted this. Yeah. Like I basically take a photo of Chat GBT and I'm like hey roast me like tell me what you know does this look dorky? Did these jeans fit properly? Whatever. And it started making good recommendations. And I was like oh like this could be an app. Like I don't know that that many people will go to the

lengths I did to prompt it and do all this work. And so um you know I used a bunch of AI tools to start building it and then I partnered with a friend of mine and we started using all the APIs and it mostly was an exercise in how do the tools work, what's possible. Um but even that it's like very quickly I'm like I'm basically like this is just an expensive education. Like unless I find someone amazing to take the reigns of it, it's not going to go anywhere. And so I think people people

really I think from the outside I think a lot of people misunderstand me, right? If you look at me on Twitter, it's like, oh, he's like doing all these things. And it's like, no, I'm just [ __ ] around with that stuff, right, to learn what I'm actually doing is buying companies, right? That's just all the That's like me talking. I'm like the the investor talking about how they play bridge or pickle ball, right? It's like that's just that's a pastime. Yeah. That's amazing. Top 10 in the world in pickle ball. Sure. Yeah. I wish.

Yeah. Yeah. is when talking about Twitter like one thing that I'm going to go away after this and take take some notes and listen back to this and just takeways for myself. I think two things that come to mind as related to that is the importance of you know putting yourself out there and meeting people and being systematic about in getting those interactions. How has Twitter specifically cuz I know you've talked about like in 2020 you started tweeting more um doing more podcasts and things like that like how has that impacted your investing in terms

of like deal flow and as well as just you know your personal life being able to you know host this conference and things like that. Well, I think the magic um I remember when I was younger and lesser known, I would have to go to TED to meet the interesting person. And then when I meet the person, I have to give a really compelling pitch, right? So, you have to get really good at telling your personal story and figuring out, okay, this person is in science, so how do I tell my story in a way

that'll be exciting for a scientist? Or this is an older business person. Now, I got to calibrate and whatever. And what I found is cool is um through Twitter and the book and and podcasts and stuff, you know, my name gets out there enough that people might have a sense for me when they meet me. Usually my favorite is when someone just goes, "Oh, I read your book." Cuz then I'm like, "Amazing." Like, you know, you already know me 100%. I can just learn everything from you and like I don't need to sell myself or

anything. And then on top of that, now I don't have to go to the conference. the people will just email me and say like you did, hey, can I fly to Victoria and meet you? And I I think that's like awesome, right? So, so that's been the benefit of it. And I think that the downstream to be honest I started tweeting because frankly I was really depressed and miserable during co and I was like I just need something to do every morning like when I'm sitting here in lockdown and so I started sharing you know

what I was doing and I've always my strategy to grow metalab in the early days as well was blog posts picking fights uh case studies talking about what we were doing all that kind of stuff. And I think that um I've always been a loudmouth and so my default is to share and talk about what I'm doing and you know evangelize or criticize or whatever. And so for me it's very natural and the benefit downstream. I get to meet interesting people and deal flow. I mean, we get a ton of proprietary deal flow. Most um,

you know, aside from me networking and all the other stuff and all the deals we get through that, we also get inbound hundreds of emails every single month from people that want to sell to us because they've already heard the story and they understand what we're about and they like what we're doing. And I think one of the really underappreciated things about Tiny is just that we don't do outbound, right? Like I mean occasionally, right? Like I emailed Alan Adler about Aeropress, but for the most part the deals come to us. Um, and we I

think like what most private equity firms get wrong is they name themselves and they their copy is all designed to appeal to investors, right? So, um, I remember I would get these emails from private equity firms. So, you know, when I was running probably in like 2014, 2015, um, you know, some of our businesses started to make serious money, $45 million a year, and we'd start to get in these like databases. And the way that all private equity firms do their outbound is they just go in and like Pitchbook or whatever database, and they cold

email you, and they send an email that sounds like this. Dear Andrew, my name is uh Quentyn Carlson and I am a associate at Bridge Partner Limited. Our founders come from Goldman Sachs and Tiger Global and whatever. Our AUM is uh $10 billion. We specialize in rule of 40 software companies that are in which we can deploy $und00 million in preference stack equity. like just I was like and and at this point I'm like what is this guy talking about? I have no clue. And then it was I get on the phone with this guy

and I'm like I'm like does this guy run the firm? Like who is this? And he's like this wonk, right? He's like some Wall Street analyst type and all he's asking me is like numbers like uh you know what is your churn on this MR whatever, right? And I'm like what? Like what are you talking about? what like what is capital like what are you what is e I didn't even know what ibida was like back in the day and I was like what are you talking about and I think the pro this is goes

back to the problem it's finance people going what would I want to hear right and they don't know how to speak founder they don't know that a founder doesn't even they never use the word capital they don't know what aum is they don't know what ibida is they just go uh this is my business this is what we do these are my employees this is how much money we make you know net profit they know that right and So I think the one thing that we really got right with Tiny was just pivoting the language

and saying if you look at our website like it doesn't look like a multiund million hold co you know most of these private equity firms have like black and white skyscrapers and investor portals and all that stuff just looks like kind of goofy and friendly and it it's all written in a way where a founder sees it and it's not intimidating and they get it and uh and yeah I mean if that's our big That's like the insight for us is like don't is like market that and talk to founders, right? So that is the

downstream benefit for us business-wise. It's huge. Um the downside is uh yeah, you get like crazy people and all sorts of other stuff. Yeah, you can buy the book if you want to read. Yeah, in my book I tell some good stories about that. Yeah. Um two two questions that came to mind. One, I'm just going to say them so I don't forget, but one, does that mean investing is actually way harder? like capital is actually the thing that's very abundant and then two is that also then the benefit or is that also why you

guys have a mo in that sense in terms of you mentioned like with AI brand is actually something and network effects like those are two things AI can't disrupt necessarily like is that a big benefit for you guys being so online that your brand has been built and is so distinct well I think um one of the mistakes a lot of people make is they assume that there's an efficient market for selling businesses and I I think that if there would be if every founder listed their website on a public directory that said here's our

revenue, here's all our financials, whatever, and at any time any market participant could bid and just say like, you know, I'll buy 10% of your stock for $100 million or whatever. Like, totally perfect market, right? The reality is that most founders don't even know what an investment banker is. Like, I didn't know what an investment banker was. For those that don't know, an investment banker is a realtor for businesses. They're just a realtor, right? They go and they they there because it's an inefficient market. They they go there and they say, "You want to sell

your business? Great. I'm going to run a process. I'm going to go and sell your business for you." And even that is a highly inefficient process because the bankers only have relationships with a bunch of private equity firms they have good relationships with. And so they'll go to 10 firms most of them or maybe maybe they go to 50 firms, but usually it's like 10 20 firms or whatever. It's one email. It's a generic email to them and it says, "Hey, I have this business. Here's the um confidential memorandum or whatever and here's all the

info." Most of them just go, "Eh, pass." Right? So then you get down to like five, right? And then you have this competitive process amongst five. So to me, that's not a very efficient process. And it goes back to the power of relationship. And I think, you know, if I was a very, very wealthy person at the end of my life and I owned, you know, $2 billion of equity in a private business and I look at two options. is I go, "Okay, I can go to the banker and I can run this six-month process

and I can sell my company to someone who I just who has a punchable face from Wall Street who looks at my business like a spreadsheet or I can go to Warren Buffett and Warren Buffett is friendly and nice and will do a deal on a handshake and he'll wire me $10 billion tomorrow and I'll get less, right? I'll get, you know, I'll get a little bit less, but I I know my company's in good hands and trustworthy." Yeah. I personally I go all day with Buffett, right? Because you're so rich it doesn't matter. And

uh I think you know that's the advantage, right? Is like being able to get great deals because people actually want to be treated well and know their company won't be messed up. Well, to your earlier point like you know a banker or someone buying a company might only think of the financials, but because you guys have been there, you've had all those conversations already and you know you're a founder yourself, you can understand like okay maybe this person doesn't actually care that much about the money. They just want a little bit of stability and they

just want to sell a part of the business. And I don't want to malign private equity and frightly. I have tons of friends that are in private equity that are incredibly smart, incredibly thoughtful, totally ethical. Um, I'm more criticizing their approach. I just think the approach is backwards. It is just so bizarre to me that they pitch themselves in this way and they hire people in suits to try and buy businesses in the Midwest. You know what I mean? Like it's just just weird. And I mean Brent is a great example. He's doing the exact

same thing we are but just in brick and mortar businesses. And he he's straightforward. He's written a book that's like down to earth. Like he's just a guy, right? I think that is that's a unfair advantage. Yeah. Are there any problems that you see like you mentioned if you could have every business giving all their data all at once? Like that'd be a pretty cool uh data set, pretty cool business. Are there any problems that you see that you'd want to have solved um in that buying process or anything unrelated to brand and network? Any

any opportunities? I'm just curious. Well, there actually interestingly there's something called Company's House in the UK and they actually do require all companies over a certain scale to do that. So there there kind of are some of these databases but I think they get picked over. Um in terms of a problem I would love to see resolved. I mean, legal Mhm. is a huge inefficiency. Um, one of the funniest things I find is, you know, whether we're working on a hund00 million deal or a $1 million deal, the legal bill always somehow manages to be

between half a percent and 1% of the total deal size, even though the legal work is the same, right? It's like the same number of documents, whatever. Um, and I I feel like that is it just it adds so much inefficiency. And like I don't know if you've ever negotiated like a contract with a business partner or something. Me and Chris don't have one, but I've done like um business partnership agreements and stuff. It's the sort of thing where if you just sit down on the same side of the table and you like hash it

out, it's great, but when lawyers get involved, it overly complexifies everything. And usually the lawyer's job is like, "Let me whisper in your ear and freak you out so that I get another 10 days worth of legal work out of this cuz I can add a bunch of clauses and stuff." What I'm excited about is when I can get on the phone with the founder and say, "Hey, let's both open Claude." Yeah. Um over the next 3 hours, let's just like figure this out and like, you know, you say, "Um, I'm really scared that, you

know, I'm going to sell you my company and then you're going to sell it again in a couple years and it's going to be 10x." Yeah. Yeah. All right. Let's add a clause. Like let's claude like how can we resolve this? Like come up with a great structure, right? And I'm excited for that more human level um communication. And then also I own a um I own a building and I rent out some of the units and I recently had Claude write a lease and I wrote this like big complicated lease and then I just

said um the person who's reading this is like a small business owner. Can you please make it legally binding but put it in language they'll understand? And it just it just re it was like you know before it had like um therefore clause a and then it just made it like oh by the way this is what this means and like here's the intention with this and if this doesn't happen then it would fall back to this right and it's like everything goes back to my private equity example of like I'm excited for everything in

business to become straightforward more human more more natural totally do you think that's the biggest advantage in a negotiation is changing your seat to be on the same side as the other 100%. I think saying to someone um one of my favorite questions to ask a founder is how does this go wrong? What are your fears? You know, what what's your what's your husband saying to you at home that is like oh don't make you know make sure that doesn't happen. And I think it's so powerful to go to a negotiation just saying like, "Hey,

like let's lay all the knives on the table and just say and like you know that for me too, it's like you know, hey, I'm scared like you said you want to stick around, but like you also are going to take $20 million off the table. Like you know, are you going to be here?" And and if the person looks me in the eyes and goes, I'm obsessed with this business. Like I'm not going anywhere. It's like that's all I need to hear, but I want to be able to say that. Um, yeah, I think

it goes back to like it's 90% therapy, psychology, uh, EQ, like those are the things that, um, you know, you need to do great deals. Yeah. Not not very well, uh, you know, not that you're great at math or like can do derivatives or No, I mean, yeah, like no, no, um, no spreadsheet jockey is going to be able to buy great business in my opinion, unless you're in the public markets. in the public markets because you have perfect information. It's a blind bidding process. Yeah, of course you can. So if you're that type of

person like no and no I'm not casting aspersions like that's great. Your brain works like that like public market just be aware of it and go that way. Totally. That's amazing. Um one question I have for you and then then I think I'm I'm close to to wrapping up. What what are the how do I how do I say this? Um, what questions have you asked yourself? This is this is more in general just for life, for business. What questions have you asked yourself over the past few years that have been the most impactful? Um,

you know, is it maybe something as simple as, "Hey, what am I doing every day? Let me just check my calendar." Or, um, something else like, are there any questions that come to mind that you've asked yourself over the last couple of years that have led to where you are now, where you're, you know, I I think in a place where you're loving every day. Yeah. I mean when I was um 34 35 like I had one of those pivot point moments of like seven years existential sevenyear cycle crisis um and I was kind of

going like you know why why do I do this you know because when I was a kid my parents would fight about money and I remember my dad I said dad um dad what's your plan for retirement and he looks at me and he goes uh you're my plan for retirement. And he's totally joking. Like my dad's a really sweet guy. But in that moment, I was like, "Oh my god." Like I'm like 7 years old. I'm like, "Oh fuck." Like there's there's no plan. Like there's there's no one flying the plane. Like dad, like

oh my god. And I I think like that I just wanted everyone to stop fighting. Like money was the thing that made people fight. Money was the thing that made vacation stressful. And money was the thing that caused me to project out and worry. M and so I'd say from 7 years old to 34 35 I was just obsessed with making money and um I hadn't really thought about what to do with it. You know, like I said, I'd had little periods when in my early 20s where I'd spent a bunch of money on dumb

stuff, realized that didn't really lift me up. And then 34, 35, I was like, "Well, shit." Like, you know, I should live it up. And so, you know, I bought two more houses and, you know, started like I chartered a yacht and like did all these silly things and I just felt like gross. I just felt wasteful and and disgusting. And so after that I was like well how do I create meaning out of money and why am I doing this and what's driving me and I realized two things one was you know I wasn't

happy doing what I was doing because the joy of running a business the joy of running the machine um was shifting and I was becoming a cog in the machine doing something I was very bad at and that thing was managing people problems like I I'm a good I'm good EQ and dealing with people problems, but I can only do so many CEO salary negotiations before I want to tear my hair out or I I my brain only can deep dive on one business so long and I can't keep so many in my head. And

so I realized that I was doing something that I wasn't exceptional at anymore. And when I was able to say, what am I exceptional at? storytelling and relationships and um talking to founders and figuring out deals and all the stuff we've been talking about. That was when I started really loving life again. And then in terms of the money side, you know, I didn't want to give it to my kids. Um you know, I'll probably give my kids something, but I I just had met so many unhappy people who had inherited money or I'd watched

kind of families decay over battles and stuff. And so, um, you know, I I kind of cracked like, okay, I'm going to give it all away. Um, and I tell the story in my book, but, you know, I got to do a call with Warren Buffett and got invited to do the giving pledge and basically that's the pledge you're going to give away at least half of your wealth before the time you die. And so, that kind of gave me a bit more of a mission of like, okay, instead of being this selfish person who's

just trying to like feather my own nest and build up a wall around me and the people I love, well, that wall is big enough. Well, now what? And the now what was okay now I'm gonna start giving it away right and so you know over the last couple years I've given away almost $20 million and really worked towards doing that and finding ways to enjoy that as well. Um but you even that well the funny thing about that is I started doing that and I still get drawn into business. I'm just obsessed with business.

Like I was talking to uh another um hold co-op operator two days ago. We're having breakfast and he's like I was like you know what you know do you want to retire or whatever and he goes well I know if I retired I would just like have a bunch of money and then I'd need to deploy the money and I'd start building my machine again right like I just love it I'm like a Rube Goldberg uh I build Rube Goldberg machines and so I've just kind of leaned into that. I'm like okay I'm building the

Rube Goldberg machine. I love business. I love entrepreneurs. That's my world. And then fortunately my um my girlfriend, my partner, she runs the foundation and she's amazing at giving away money and so we have a nice partnership. Yeah. Uh and so yeah, I'm just and I'm still muddling through that. But it has given me a sense of um you know, a rewritten narrative, right? And I think that rewritten narrative was important because I think four or five years ago I was feeling quite empty, selfish, um unhappy at work, and not in my zone, you know?

I wasn't in my lane. You're you're a cog instead of working on the machine%. Yeah, that's that's amazing. One one question. What's the favorite philanthropy thing you've been doing recently? like what's the most? Well, there's there's two two different ones that I really love. Um, so one is very tangible. So, so I kind of think of it as um a stock portfolio. So, there's things that you bet on that are like growth companies, like future opportunity. And that's where like we we invested the foundation invested in clotho which is like a really um uh potentially

breakthrough treatment for Alzheimer's uh which I have a bit of um quite a bit of in my family so quite passionate about that. Um on the flip side uh so that's like a future bet right of something that could profoundly impact the world and benefit people in 20 years or something. on the um on the more tangible side we do um traoma surgeries. So we donate to sight savers which is in Africa and basically uh in certain uh African countries and other places around the world um people will get this forma it's almost like pink

eye it's like a horrific pink eye but you uh they don't get treatment for it and the only way that to treat it is actually to get this special surgery if it's not eliminated quickly enough and what ends up happening is something that's as simple as pink eye ruins someone's life and when I talk about ruining someone's life I mean they can't work they are not able to care for their kids, like very very bad situations. And so for I believe it's about $750 a pop, you pay for these traoma surgeries. Um, and I find

that really really satisfying because on one hand I'm doing something that's really tangible, changing people's lives and yes, very clear. You know, it's somewhere else in the world and I'm probably never going to meet those people, but I know I'm doing some good. And then on the other side, I'm making these more long-term bets. Um, another really funny one. This This one I I don't do Through the Foundation because I haven't figured out a I It's not really It's kind of more just me being like goofy. I have um so my whole life um I've

never been able to burp. What? Yeah. Imagine like not being able to fart. Like you just every day you just That'd be kind of nice though. No, it would be nice until you're just bloated every meal. And so what would happen for me is um when I was about 24, I started getting every day I get um my whole life like if I drank like beer or pop, I would just feel horrible. I just feel bloated and I'd get these horrible gurgles. Really embarrassing like almost like a velociraptor noises like so I'd be on a

date and I'd you know go in for a kiss and right like very very embarrassing and but but in the beginning it was just kind of funny. It was like, "Oh, I can't burp." And I'd say to my doctor and he'd go, "H, you're probably burping. You just don't know, whatever." And so, um, but at about 24, 25, that turned into horrific acid reflux. So, every day I just I'd get this pressure and I just get this horrible acid reflux. And so, it sent me on this journey of just like, what is this? How do

I get rid of it? And I tried taking every medication and nothing worked. and they look at me and they go, "You're uh, you know, you're 26, you're not overweight, you don't smoke, you don't really drink, like what, what's the deal?" And, um, no one can figure it out. And then one day on one of my like many like literally I'd spend every night, like 3 hours at night just like reading all the scientific literature trying to figure out this acid reflux because it was ruining my life. And I I I thought about, you know,

I can't burp. I wonder if there's something to that. And so I Googled it. I just Googled I can't burp. and this subreddit came up called no burp. And I realized that there's like there's like hundreds of people that are all on there and they're all saying like, "Oh my god, I got these dino gurgles and this pressure and I feel horrible." And um I was so excited because um there was like 20 people in the world who had gone to Chicago and there's this one ENT named Dr. Robert Bastion who had figured out that

if you that it would it was caused by your cryoparangia geal muscle in your throat being too tight. And so what he started doing is going um putting you under going in endoscopically and injecting Botox into the muscle that relaxes it and allows you to burp. And so I flew to Chicago. I got this procedure done. I stopped getting acid reflux and now I can let out these like massive burps. Like like fortunately I'm not drinking a bubbly right now, but like I usually just I can't stop. I just keep burping and it's amazing. It

changed my life and I was and it sounds goofy cuz it's like oh it's burping painful. It ruins people's lives. Like it ruins people's lives and especially in Canada you most doctors will not take you seriously. Very few people are aware of this disorder. And so what I started doing is um posting on Reddit threads and just saying anyone in Canada who needs this, I'll pay like just go. And so I think I paid for 10 or 15 people now to go and get this surgery. And I just love like it's so paying it forward.

Yeah. It's so relatable when you're fixing their problem that you had. Totally on the I don't want to like you know to be like oh yeah my philanthropy is all like burp surgeries. So like we also are doing a lot of work um so we've funded a bunch of stuff around um you know addiction specifically like u researching novel compounds to treat addiction and there's some interesting work there. a lot of stuff through Stanford. We're funding um rapamyosin research which is like a a longevity drug in dogs specifically. They're doing this very large study to

see if it extends lifespans in dogs and then moving it to humans potentially. Um so that very interesting like potential intervention to expend extend lifespan by say you know an extra 10 years. That's huge. um a lot of work on treatment resistant depression. And then my girlfriend is mostly focused on uh nonprofit reform. Uh to kind of like summarize her idea, it's you can't change the world by paying people McDonald's wages because the unfortunate reality is that in most nonprofits, they pay half of what they do in the private sector. And you just you can't

get uh you know, you can't keep great people there. Yeah. you I think you you say in your book like that she mentioned that the turnovers I don't know what it was but it's like incredibly high for the employees. Yeah. I mean if you can't buy a house you're not going to stay there. And I just think that it's a sad thing when you have this really ambitious goal. A lot of these nonprofits are doing incredible work. And I understand that you know look it's hard to allocate capital to salaries when someone is struggling and

they need to help them. But ultimately it's one of those realizations we all have that if the business is going to grow you got to pay people really well. And so she's working a lot on that and trying to figure out models of can you can you show that if you pay your people well um the outcome is actually more successful and you help more people. Yeah. That actually get the result of the nonprofit. The hard part with philanthropy though is there's no profit. There's no there's no objective measure measurement of how it's going. Like

if you um if you go to a business conference and you talked to 10 of the world's most successful people, you went one by one and you just interviewed them and you said, "Tell me the three key things to having a success in business." They would probably tell you three similar things, maybe a bit different for each, but you'd hear some themes. Um as part of the giving pledge, I've gotten to meet all sorts of amazing philanthropists. you know, some people giving away over a billion dollars a year and everyone says something different, you know,

and all of them say it's hard and I, you know, often I don't know how to measure it. And I think that's a bit scary, right? You're deploying these huge amounts of capital into something and there's no objective measure. And that's that does go back to why I do enjoy while most of our bets are not the traoma surgeries. I do like having a little bit of that or a little bit even a little bit of local, you know, we do quite a bit of local philanthropy as well just cuz it's something, you know, this

is a barbell strategy, right? Like you're going for the big high growth bets that you might might never have but you're not sort of directly related to or anything like that and then something more local. That's awesome. Um any anything you want to tell the people or any any lasting like you know Well I I would just say like the way place we started in this conversation was um talking about interesting people. Yeah. And I think like what I love about doing podcasts like this is um you know I have my own people that I

that know me from Twitter and stuff but I promise you that I'm sure lots of people watching this don't know who the hell I am and whatever. And I just say that if probably vice versa. Yeah. Right. And if I think if anything has resonated with you, uh, add me on Twitter, send me an email. I mean, reach out and and if you're interesting, I'd love to meet you. I just love building out that network. So, yeah. Yeah. Amazing. It's worth it. Fly Fly to Canada if you can. It's It's worth it. Awesome, Andrew. Thank

you so much, man. That was uh That was so fun. That was a ton of fun.