0:00To be an entrepreneur, you have to endure people thinking you're an idiot for a while. My parents were kind of like, okay, like, are you paying your taxes? What's this business you're doing? Should you go get a job? You feel like an idiot. My friends were all going to university and they were all learning about cool, interesting things and partying and having all these neat experiences and going backpacking and I was working and I was like, man, I'm like missing out. What am I doing? But then when they graduated university, I
0:27owned my own house. I really wanted to buy a Porsche. I just always had it in my head that I wanted it. I always put it on my mood board, vision board, or whatever when I was a kid. And then I bought a Porsche and I got in it and I was like, "Wo, the seats are really low.
0:40Wo, it's really rattly. It's really loud. And man, the stereo is not that good." Wait, the car I had before that isn't as fancy was like better in so many ways. Someone can tell you that something sucks, but it's really hard to read about something and truly understand it. Going to the Oscars, it's a hundred grand or something like that to attend, getting a crazy tux and donating to get seats and all that stuff. I just feel gross afterwards. I'd been pretty conservative. I hadn't really spent a lot of money
1:10irresponsibly. And I was like, let me try a few things. Chartered a yacht with some friends, did the Oscars thing, and a few other things. Why did I do that? I just felt guilty.
1:21What do you think has been the weirdest rich person party that you've ever attended?
1:32You became a multi-millionaire in your early 20s and a billionaire at 36. But what I find funny is we both went to Oak Bay. We went to the same high school. We both almost failed grade 11 math and neither of us were popular back in high school. If your younger self from high school met you today, what would he think?
1:51At almost any level of success, the younger you would be absolutely blown away. If I told the younger me that I had a job and I was making like 40k a year, I'd be totally blown away. And I remember like I started out university dropout. I was working as a barista and all I wanted at that point was to be able to pay my rent, take my girlfriend out for like a nice dinner and be able to go drinking and be able and afford it. I feel like that first level was
2:20like probably the best and then every level subsequent it's just been like a slow boring evolution and so I haven't really I haven't really noticed it. You mentioned becoming a billionaire at 36. Well, I'm not a billionaire anymore. Yeah, our stock went way up and then way down. And that that too was a really interesting uh experience. But I think I think young me would be pretty shocked.
2:42Even me from 10 years ago would be completely shocked. My dad would always talk about compound interest. If you just save a dollar every day of your life and you invest it and it compounds at like 10%, you'll be a millionaire by the time you're 60. And I was like, "No, that's impossible." And when I started making money, I remember I sat down in Google Sheets and I I was like, "Okay, so if I make a similar amount of money and it grows, you know, 10 to 20% a year by starting businesses and growing the
3:11ones I have and investing my money, where will I end up in in 10 years, 20 years?" And I remember seeing this number. It was like $200 million. And I was like, "That's impossible." Like I didn't do the math right. And I'd hit that number within five or six years of that. So, it's uh it's kind of a crazy experience to have that happen. Like compounding is a very powerful thing.
3:3420-year-old me or 15-year-old me would be pretty shocked. What do you think was a belief that you had back then maybe about money or life in general that turned out not to be true.
3:46I had this weird self-confidence. I remember one of my friends was he was an English literature major.
3:53Yeah. We're talking and I I've always loved writing and I said, um, you can achieve anything you put your mind to.
3:59If you have, uh, you know, the basic skills and the intelligence, if you apply yourself, you can do it. He's kind of saying like, no, I don't think so. I think you kind of have to be like a genius to, you know, write the next, uh, great novel or whatever it is. And I said like, well, I could write the next great American novel if I put my mind to it. Like, I think I could, for sure. And you know, that's kind of hilarious and egotistical looking back, but I've just always had this sense that if I put my mind to it, I can figure out how to get
4:28there for whatever reason. And typically for me, that's just been getting obsessed. So whether it's learning how to DJ or starting a business, I get obsessed with things. I read every book.
4:40I figure out who all the best people are. I listen to all the podcasts. I I get completely hyperfixated on that thing. And I'm what I've realized is I'm really good at getting proficient and not good at getting exceptional at almost anything. So like I can get pretty pretty darn good at most things, but I'm not good at the detail required to get to like exceptional level.
5:03Why do you think that is?
5:05Probably because I have ADHD.
5:07But I didn't get diagnosed until a year ago. So before that, I just thought like I'm just not disciplined. Like I would uh I would always think like, oh, if I just have the right productivity system or I read the right book or I whip myself harder, I can be more disciplined. And probably about 10 years ago, I I finally realized like I just don't have the discipline to even run a business dayto-day, right? Like I have so little focus that I get bored of something. The moment I get good at
5:36something, I get bored of it and I have to move on to the next thing. And so I realized that made me a very bad operator of companies. You know, I know I know what a good operator looks like, but I'm not one. And it makes me a good investor because I'm able to know what a good operator looks like, know what a good business looks like, buy it, put the operator in, and then get bored, move on to the next business. So for that reason, it's been positive. But it took a long time for me to take the ego hit of realizing like, wow, I really
6:06suck at details and I really suck at running businesses. Honestly, I find with my ADHD, I'm definitely definitely in a similar spot.
6:15It it's like my mind's always just overflowing with new ideas and I find like it's so easy for me just to bounce from from thing to thing, but then hard to sit down and then like stay focused, follow through on something. But I al also I I think from reading your book and listening to you on other podcasts like that ADHD and almost how you describe it like not feeling like you're very disciplined. That's one of the biggest reasons why you've been able to find the success that you've had. It's
6:44like you've almost used that thing that might might be negative as a positive thing. So how do you how do you think you've been able to do that? I would say I'm strategically lazy and that makes my life really good in a business sense.
6:59That's a gift in a business sense where the moment I would do a task that I don't enjoy, I'm lazy and I just go, I don't want to do it. I want to delegate that. I'm going to build a system so someone else does it and then I'm out of it.
7:11And a lot of entrepreneurs struggle because they can't delegate. They are so obsessed with their business and they're so focused that the idea of someone else delivering the product or doing doing the thing almost physically pains them and they really struggle. So I was good at dropping that and I had this saying in the early days that I was teflon for tasks that I really my goal was that I really didn't have to do anything and that I could disappear from the business
7:40at any time and it would keep running. What that resulted in was a lot of businesses that ended up growing a lot faster than they would have otherwise because I didn't run them cuz I wasn't very good at it. What's ironic though in my personal life that also makes me like a really frustrating boyfriend. So, you know, I never want to take out the trash. I never want to do the dishes.
7:59Uh, it physically pains me to do anything boring. I hate playing board games, right? So, it's kind of a funny breakdown in two different worlds, but yeah, it's turned out to be a gift when it comes to the business side. That's a great point, the the delegation. But I I also think a lot of people listening to this podcast are people who are just starting out, like they might they might not have their business yet. They might be more in the early stages stage of their business. What do you think you'd do if you were at that position where you haven't really grown your business
8:28too much yet to have the capital to be able to delegate as much as you want to um still delegate and then still like be able to use like DHD as an advantage.
8:42The goal of delegation should be that you take the time and you either make more money from your own time. So you're delegating the lower the lower paid jobs and then you're doing the higher value jobs or ideally you're actually getting your head above the cloud so that you're growing your business. So let's say your business as an example car detailing. So if you do all the jobs yourself, you know that you'll make a set amount of money, you have so much time and that the product the service will be exceptional cuz you know that you'll do
9:11it really well. But let's say that you because you're detailing cars all day, you're not running Facebook ads or you're not going and door knockocking or you're not thinking through pricing strategy or any of these things. And I think you need to delegate in order to get the leverage on your time. And it might mean making less money in the short term, but it's because it's freeing you up to actually think bigger. The hard part is can you stay focused enough with your
9:38ADHD to not just start a new business but instead actually improve the business you have because what I found was the business I started would be so exciting the moment I started making money from it that was like the hit of dopamine but once it became routine I really lost interest and wanted to move on to the new flashy business not focus on the business I already had. M I definitely agree with what you're saying about about the detailing. Like I find on the days where all I'm doing is
10:08detailing cars and just out there 8 12 hours a day, then I don't have time to do the sales, leads are falling through the cracks, I don't have time to run the ads, do the pricing, like do the things that actually move the business. So, even it's like even though I'm saving maybe two $200, $250, $300 by not having someone do it, like I'm making a bit more profit, I'm losing out on maybe thousands from not doing the sales and
10:36doing stuff like that. So, yeah, I think that's definitely a great way to think about it.
10:41So if you if you were someone who was 20 20 years old, you're starting out your first business, do you think you just be delegating from the very start?
10:50Well, I did um you know, I started not the very very start, but when I first started my original business, um I was doing web design and I didn't know how to program. And so I I I remember I got a programming job, like a contract with a company and I was like, "Oh my god, like I don't know how to program. What am I going to do?" And so I found a friend of mine, um, he was a computer science student and I said, "Hey, how much would you charge me per hour to do this work?" And he said, I think it was like $30 an hour and I was
11:20charging $80 an hour. And I was like, "Oh my god, this is unbelievable. I'm doing no work except for dealing with the client and I'm making 50 bucks of profit for every hour that he works."
11:32Um, and from that moment on, I started delegating a lot. But anything that I knew how to do, I originally would do until I knew how to delegate it or knew what a good designer, programmer, salesperson, whatever that was, looked like. And I think the fundamental, it's kind of like this um chicken or the egg problem where in order to delegate effectively, you have to know what the task looks like. So you have to detail some cars to know a good detailer from a bad detailer. But you don't need to
12:02detail a thousand cars. So you could probably detail 10 cars and know what to look for and then hire accordingly. Um that's the hard part. And then the other hard part about delegation is you're going to hire usually a doofus the first couple times. You know, you almost always hire the wrong person or you hire your friend and then you got to fire your friend and go through all that and then finally after two or three hires you figure out how to hire that role. Uh and so it requires a lot of pain and it often means that people don't keep
12:31going. So like they'll delegate the first time, it'll go badly and then they go I can never delegate again. You know, they teach themselves the wrong lesson. And I think that great entrepreneurs are the people who can push through that discomfort and keep going.
12:44Totally. Did you have many experiences like that when you're first starting out?
12:48I fired uh you know had to deal with my you know hiring and firing friends, hiring completely incompetent people, hiring people who stole from me. I mean all that stuff. I think the best way to view is just through a lens of learning.
13:01Like I I've definitely made I've definitely made quite a few mistakes hiring wise. But I've learned so much from all those. And and now now I feel like I'm so much better at knowing what I don't want, which which is like which is great for knowing what I do want and actually finding the person.
13:23Totally. somebody who's 20 years old who's watching this podcast sees you and is like, "Wow, I would love to be where Andrew is or just be doing what Andrew is doing." Where I was going to ask, where's the first place you'd start? But what businesses do you think you'd completely avoid?
13:39Like which popular businesses online do you think you just avoid if you're somebody who starting out?
13:46Well, I always think the first goal is to make $100,000 a year. Yeah. Um, you know, Elon Musk didn't go out and start SpaceX. Elon Musk first did a whole bunch of other businesses and he did some more boring businesses that were not trying to revolutionize space. They were, you know, Zip 2 was like a yellow pages replacement or whatever. He made his first money doing that. And that I call it building the rocket pad.
14:13You got to build the rocket launchpad before you build the rocket. And so what I would focus on if I was a young person is freedom. So having the freedom to think about businesses or t having the time and you can't really have that freedom when you have a day job. And so I like the idea of trying to create a business that's relatively passive or someone else can eventually run that makes you $100,000 a year, maybe 150,000, whatever that number is for you. And then from there starting to
14:41diversify and start other businesses or scale the original one. I think a lot of this comes down to personality and leaning into personality. Yeah.
14:51Um when I was young, I worshiped Steve Jobs. I was like, Steve Jobs is the greatest entrepreneur ever. I want to be just like him. I, you know, I want to change the world. And I very quickly realized, I remember I read a biography of Steve Jobs and I just thought like, wow, I am nothing like this guy. Like I am not detail- oriented. I can't imagine running one business forever. like I I just I I'm not maniacal and I don't want to be like demanding to people. I I I
15:20just don't relate to this person at all. And I realized that I had to find a business or a way of being in business that worked for my weird personality. And so I think um some people they are onetrack entrepreneurs. They start a garbage hauling business and they scale it for 20 years and they take it public. Other people are serial entrepreneurs.
15:44They do one business at a time and then they sell it. Every five years they sell a business. Um you know other people want to take big crazy swings. You know they go raise venture capital and go to Silicon Valley and they try and do something crazy innovative and sell it for a lot or it goes to zero. Um for me I ultimately realized that you know I'm not focused and I needed to do a lot of stuff at the same time. And so for me, what was right was starting a whole
16:12bunch of businesses, learning from that, and then recognizing I'm not a good operator. I'm going to start buying businesses. And now I do that. Um, so the advice for young people is literally just to figure out what is your operating system like what hardware are you running in your brain and what do you find enjoyable? And then based on that, you can figure out which of those many archetypes you are and who you relate to. So, one thing I always recommend young people do is just listen
16:39to the founders podcast. David Sra reads biographies and he summarizes them in about an hour. And through that, you can learn about hundreds of history's greatest entrepreneurs and go, "Oh, that, you know, Warren Buffett, I'm like that guy, you know, I want to be like this person." Uh, that's the archetype.
16:57Um, and so, yeah, searching that out through trial and error and reading and discovery really. Um, you know, you you asked about bad businesses. Um, that's probably the most important thing that will define your success is how difficult and um how difficult and capital intensive the business model you choose is.
17:22Yeah. And I was talking to um talking to a young entrepreneur the other day and I said I think the most important thing is that you choose a business model for your first business where you get immediate feedback. So for example a difficult business would be you decide to go and start a new AI company that's going to build a robot. right now. Maybe you're a super genius and you can go do that, but as your first business, that
17:49is a very daring, risky thing to go and do. And your first dollar that you earn as the founder is probably 3 to 10 years out, right? On the flip side, and and you think about how easy it would be to break along the way. You know, it's so hard. You've never run a business before. All you wanted is to, you know, maybe you wanted to make money or whatever the driver is. Now, on the flip side, you know, your business, car detailing, tomorrow you can call, you
18:17know, three friends and say, "Hey, do you know anyone that wants their car detailed?" You can go detail a car and you'll make your first $300 within 24 hours.
18:26And I think that choosing something simple is the best way to build your confidence and to also build your wealth. And so, it doesn't matter whether that business is the thing you want to do for the rest of your life. I think this is a mistake a lot of young people make. They go, "Well, I don't want to be 45 and detailing cars, right?
18:44They think you have to be doing it in the end." And it's like, "No, this is just where you're starting." Um, and uh they choose instead something glamorous and and I think glamorous businesses are hard because they're glamorous. You know, everybody wants to go and start their own clothing brand. So, it's really hard. It's time consuming, low margin. and everyone else is doing it.
19:08How many people want to go out on a cold February afternoon and detail cars? Not that many, right? And so, you're going to instantly make money and be able to charge a lot for it. Um, the analogy I use is like you don't want to be the person that goes into the gym on day one. You've never lifted weights in your entire life, and you try and deadlift 300 lb. Everyone realizes that's stupid, but that people every day go and do that in a business context for their first business. What do you think would be
19:35some examples of simple businesses?
19:40So, I mean, anything that is like home services. Yeah. Very straightforward. Anything you don't need significant training for where like, you know, car car detailing, window washing, uh, pressure washing, anything like that. Very straightforward. Doesn't require any licensing or insurance really or anything like that. The equipment is quite cheap on a on the digital version. I mean, web design is a great example.
20:04Anyone can anyone who knows how to use a computer or chatbt now can figure out how to build a website with Squarespace or get chatbt to code something for them. All they have to do is find an old person who has a business that needs a website and say, "Hey, can I make a website for a,000 bucks?" I love that as a starting point. I don't think it's a great business long term, but it's an amazing way for you to first generate, you know, 5, 10, 20k and get moving with your business.
20:32Right. And something I'm thinking right now is the home services are especially great because they're AI proof and I'm seeing a lot of the popular online businesses like AI is totally disrupting them. Totally. I mean I think um you don't want to obsess over that cuz it's hard to predict and if you really play out the AI stuff it'll disrupt everything. But there is a there is definitely a bit of a moat to home services. The one thing I'd encourage you to think about though is if lawyers,
21:00for example, or accountants don't exist in a world of AI, where do you think all those lawyers and accountants go? They all have families. They need to make money.
21:09Where when they freak out, where are they going to go? Oh, well, I'll be safe in the services business. I'll go into the bluecollar industries. And then what happens when a thousand lawyers go into that industry? The margins go down. You can't charge as much. So, I don't think that's an overnight thing, but I think it's definitely a long-term risk for those businesses if you believe that AI will disrupt jobs.
21:35That that is a really good point. So, how do you think how how do you think somebody who's running one of those home service businesses can set themselves apart and then like for example for me, how can I like make make it so my brand is resistant to all the competition that comes in?
21:55I think the only um the only thing you can do is have a brand mode aka be known as incredibly reliable. Most people are not reliable. Most people don't pick up the phone. I mean, if you've ever worked with a contractor on a home renovation or a plumber or whatever, these the the bar is so low in terms of service that if you even have online booking, you're way ahead of the competition.
22:20Now, if smart people from other industries start competing, the quality will go up. Right? When you see um private equity has entered veterinary care and all sorts of other industries and started doing rollups, the bar is getting raised. people have higher expectations as a result. Um, but that again, this takes time. I wouldn't obsess over it.
22:42What are some other ways to think that I could build the brand out for my detailing company?
22:48I think coming up with unique propositions like um you know if there's a single scratch on your car I'll refund it or um you know we promise we will always show up within 3 hours or you know you come up with like these things that are hard to compete with that only you can provide uh or other people don't want to provide for some reason. I think um finding a way for people to become members definitely or have some sunk cost with you of like oh I've already
23:18filled out like six of my 12 stamps like I'm not going to go anywhere or whatever. Um and then again getting into other services. So you know we own a pressure washing business and one of the things I talked to to my business partner about was can you also pressure wash their car? So, for example, when you go to do a pressure washing job for someone's patio, can you say, "Hey, um, if you park your car out front, uh, pay me an extra 30 bucks. I'll do a quick once
23:47over of the exterior of your car." Right? That's the sort of thing that people who are doing pressure washing are not washing cars, but the equipment is fully capable of it. So, people are very simple. Like, they go like, "Okay, this guy shows up and I really like him.
24:01Plus, I always forget to wash my car and take it through the car wash. He does my car." Right? That's not a long-term moat, but that is the sort of thing you can add on. It will get people to choose you versus others.
24:12Mhm. And that's that's something also that it can make someone tell their friend like, "Oh, I use this pressure washing company and they also wash my car."
24:20Totally. It's a good one.
24:21Or something really dumb like um he always leaves this really delicious cookie in my car. Or you know, like something really simple. People are so simple in terms of the things that they they love these little details. There's a really great book. I think I recommended it to you off the pod, but it's called I think so.
24:40Getting everything you can out of what you've got by Jay Abraham and it's about this exact same thing. It's like how do you build customer loyalty? What are all the little details that keep people coming back and growing your business?
24:53Uh and it can apply to anything pretty much. How have you done that for for your businesses businesses in the past like metal app for example? What were you doing in the early days to build customer uh customer loyalty? We this is this goes back to me not being a great operator but instead knowing what a good operator looks like.
25:11Yeah. So, um, for example, like in metalab, one of the ways that we get business is by, um, being incredibly useful and making like executives at big companies look good, right? So, an example would be like, let's say that we did a big project for some Fortune 500 or whatever.
25:34We make sure we set up the executive so that they look incredible and we're not the ones taking credit. we're just quietly behind the scenes, right? So, it's like thinking about how to make your customer look really good or give them pride or whatever it is. Um, stuff like that. I mean, honestly, like I didn't do any of that, though, right?
25:53Like, I really didn't run I haven't run a business fully since 2008.
26:01Wow. So, there's there's lots of um you know, there's lots of little things that we do throughout all the different businesses. cuz we own 40 companies, but I don't really know what a lot of them are, honestly.
26:13I I've never been the person to implement any of that.
26:18Well, that that's crazy to hear since you you haven't ran the business yourself since 2008. So, what what were the steps that that you took took with that? Like, you went from running the business and then where where did you go after that? Like after do you get what I'm saying? like after after you fully stopped running the business.
26:40So I first business was Metalab which is a um product design agency. So we would we would work with large companies and startups to build like web apps and software and that sort of thing some marketing and logo stuff.
26:54Um basically what I did was I went away to Europe for the summer and I put my college roommate in charge.
27:02I just said you're good at talking to people. I just want you to send invoices whenever a client emails. I want you to get on the phone with them. Here's the projects that are going on. Just do your best. And it was totally irresponsible. I didn't know who else to hire. I just randomly took a chance on my friend Mark. And it turned out he was amazing.
27:20And so I got back after um a month and a half away in Europe and I was like, "Oh, the business is running just fine." And so I made him I think I made him like general manager or something. and I was still technically CEO, but from that moment on, I really didn't um I really wasn't running the business. And then I would only do stuff I really loved. So, for example, like if we got a really cool client, I might get involved a little bit in the design or or meet the client or something, but I pretty
27:49quickly got out of the day-to-day. Um, and there was moments where I would come in and help with something, but for the most part, I just moved on to starting more and more businesses. So I started a you know two software companies around that time. I started a Shopify software business shortly thereafter. Um you know cat furniture business, pizzeria skin care company, online DJ school, all sorts of dumb businesses as well.
28:15So what did what did your days look like back then?
28:18Well, uh I would wake up I was a total night owl. Stay up until 6:00 in the morning usually. Sometimes working, sometimes drinking and partying. And I would wake up at like 2:00 in the afternoon. I would do maybe like a meeting or phone call or something. I would go to the office for a couple hours and then I would work in the evening, maybe have dinner with my girlfriend, and then um I would just work all night basically. Um or I'd
28:47party. It'd be kind of 50/50. So I was, this is the interesting thing about me is I was not at the time I was working the most irresponsibly. I was growing the business the most. So I was drinking four or five nights a week. Uh I was working fourhour days a lot of the time and I was still able to be successful because I was delegating. And I think that's really horrible advice for most
29:16people. So I hope no one listening is like, "Oh, that's that's the way to grow a business." But ironically for me that worked for whatever reason. I think because I was able to delegate a lot. Yeah, that's that's crazy because the the advice the advice they hear nowadays is like, "Oh, wake up at 5:00 a.m., take a cold shower, like live this super rigid life, and work 12 hours a day."
29:37But but then everybody has a different thing that works for them. So, yeah. So I I think that's that's really good to hear. Like even if somebody doesn't exactly follow that routine, like even even if some somebody just just hears this and then goes along with what whatever they're currently doing, it's still good to know like there's there's other ways to do these things. Like you don't have to you don't have to act this certain way in order to find any success.
30:06Yeah. you can you can hire someone else to run the marathon for you and you can be the coach and you can provide the food and the housing and and you can sponsor them. Um, but you can really create an incentive structure to have other people run the race and do that work. And don't get me wrong, I am a very hard driving uh extreme person in terms of wanting to get the outcome that I wanted, but I wasn't willing to make myself
30:35miserable. I've always like the realization for me is like, you know, I've really only got like four to six good hours of work in me. I don't find I can really produce that much and I can usually get all the things I need done in 4 to 6 hours. I don't need to grind.
30:49I don't need to get up at 5:00 a.m. and do all joining stuff and all this whatever. Um, so for me that worked. But again, it's like there's a there's a quote I like. It's like uh these are the these are the numbers I use to win the lottery, right? It's like that doesn't I can give you those lotto numbers and you're a different person and it may not work. So be careful.
31:11It's like the survivorship bias like you were telling me about before.
31:14Mhm. Exactly. Like um my friend Rejie has a good line. And he goes, uh, if you know a thousand gazels run across a crocodileinfested stream and all them die except for one, the go the the gazelle that survives will go on to write a business book about how he's a genius at crossing streams or something like that, right? And you got to remember there's definitely an element of luck and timing and then winning like the biology, right? So having the right
31:42biology to be able to do that and and it work have it work out. I don't know. There's a lot of things that had to go right in order for that to work for me.
31:51But I do believe that you don't need to do things you hate. You can delegate those to other people. Yeah. So I think I think somebody might might hear about that, hear about the survivorship bias and and then be kind of paralyzed like not really be too sure which path to go to go down, which advice to take? How do you So when when you're making a a decision, how do you determine whether like this is just a freak case, like
32:20just somebody found success, but like a whole other a whole lot of other people failed, or if it's actually a viable path for you to go down? because I I remember one of your tweets actually it was like for every Jeff Bezos there's like 10,000 Jeff Bozos and I think that's true in a lot of cases.
32:37Yeah. I think um if you look at how intentional someone was and how much risk they took, you can kind of work backwards from there. So, um, you know, there's a lot of people who are crypto multi-millionaires and they have a lot in common with people who got called for jury duty, right? They just got lucky. It was random.
33:00Definitely Jeff Bozos.
33:01Jeff Bozos, right? But, but then there's also people who were um, incredibly thoughtful and had a thesis and went and did it. And you know, like we worked with Brian Armstrong at Coinbase and like in 2010 or whatever it was 2011 when we worked with them, he was a true believer and he had this vision and he went out and he he made the vision happen. And there's a lot of people like Brian who were not successful that tried to create businesses similar to Coinbase. I don't know that that means
33:30he's lucky, right? I think that but you have to reflect that he was fortunate to get the right investors, be based in San Francisco, get the regulatory approval when he did become the default. There's a lot of things that had to go right for that to work. And I think what you want to do is just think about how many things had to go right and how lucky that person had to get in order to get where they are. And I um I think that
33:58when you look at someone like me, it's like I definitely had a lot of there's a lot of like you know people throw around the word privilege. It's like okay I grew up in a household where people uh you know I was loved right and my parents encouraged like reading and they talked about business a little bit here and there and uh I grew up in a um I went to public school but I went public school with a bunch of rich kids. So I learned how to talk to rich people. So that already on its own is like this
34:27massive privilege where it's like when I was doing web design and talking to um people in business, I just knew how to talk to them naturally, right? So it's like I have all these super boosts, but at the same time, what I did, you can look at it and go, it's not that hard.
34:42It's not that hard to go and talk to business owners and see if they want a $1,000 website, right? That that's not that complicated. It's not that complicated to go on an internet job board for startups and email all the founders and be like, can I design your website? These are not 10-ft hurdles.
35:00The these are one foot hurdles. So, I think a lot of the things I've been successful at are relatively basic in my opinion. Um, and you know, do I have a a couple boosters? For sure, but I think most people can probably do them.
35:13Whereas to create Amazon or SpaceX, that's like there's so many leaps that have to occur in order to be able to do that, you know, that you have to be very careful with survivorship bias. That's true. Well, I think I think everybody like you were saying how you you grew up in a loving household, grew up in Victoria, went to went to high school with people who are rich, etc.
35:37Everybody has those things in their life where they they got lucky in some way. Like everyone has their own unfair advantages and I think it's about finding those and then being able to play into those more.
35:48Yeah. What do what do you think were some other advantages that you you might not have been born with but you like developed or you think you had naturally like most designers and engineers I find are very introverted.
36:00They don't like to talk. I love to talk and I'm extremely extroverted. So the thing I think um I got lucky that I was um you know okay at design.
36:12But I could go and I could sell and I could speak to anyone and I had this weird false the crazy confidence I talked about earlier where I could go into a room with a CEO of a company where I don't deserve to be and I could act like I did. you know, I could for whatever reason I'd warp my brain into thinking that's just a person and I'm just going to talk to them about how their day is going and you know, and that just worked for me. Um, so I'd say that was a huge boost. And then the
36:38other one was uh reading. My parents didn't have cable, so they were like an anti- TV household. And uh we didn't have cable until I think I was 14 or so.
36:49And so I just read a lot. And my parents always over and over and over again uh would force us to read. It would just be like no, there's nothing else to do here. We can go to the bookstore, we can go to the library, but uh we're not watching anything on TV. And so I think getting in the habit of reading um probably is like the biggest thing because I I really have not found any great entrepreneurs that don't just read all the time or if they can't read, if they're dyslexic or something, they got to be consuming audiobooks or podcasts
37:18or something. They have to always be learning. Um, you know, if you're not a learning machine, it's like hard to be successful in business, I think.
37:25Right. Right. And I think another great way to learn is through podcasts. And then like me doing this podcast, ever since I started this about 2 years ago, being able to speak to all these great people, I've learned so much from that.
37:42And that's been one of the best ways to learn. And even just like being in the proximity of other people who um who I want to learn from, that's been huge, too. But in terms of in terms of reading, what do you think what do you think are some of the books that have had the biggest impact on you that you don't really hear too many people talk about?
38:03Well, my favorite um my favorite book, if there's one one strategy or tactical book I'd recommend, um it would be Influence by Robert.
38:13Oh, that was great. And it's all it is is kind of a very high level overview of how psychology is used to convince people to do things basically.
38:23Um and it's probably the most powerful book I've ever read. Like there's so many things that I apply on a day-to-day basis from that book. Um so psychology um writing. So there's a book called Made to Stick by Dan and Chip Heath and it is about how to write in a way that gets people to pay attention and never forget what you say. Check it out.
38:44And so that was huge. And then in terms of the story side, um there's a book by Felix Dennis called How to Get Rich which is absolutely incredible. And I think I remember I read that book when I was probably about 20. And in the book, he starts out and he says, "Look, I made hundreds of millions of dollars and it ruined my life. You don't want to get rich. Here's all the ways that it ruined my life. But if you really want me to,
39:13I'll tell you how to get rich." And I remember reading that book and being like, "Whatever, old man. Just like shut up and like tell me." And uh and it's incredible because he was this random hippie who started selling uh kung fu posters, Bruce Lee posters, and then he somehow started a magazine and publishing empire that was a you know multi-billion dollar company and was very very successful guy. Um but it was that book was so uh so accessible to
39:42be like wow this guy's just some random dude and he just cobbled it all together and figured it out. And I remember reading that and going like, "Okay, if this guy can do it," because like previously I'd read about like Steve Jobs or these like crazy like super genius level people. This was like this guy's just like me. He's like a normal dude. Uh and that that was really impactful for me.
40:03Are you are you glad that you didn't you didn't listen to what he said at the start of the book?
40:08Yeah, for sure. I mean, it's funny because it all comes true. And it's one of the the the problem with advice is you can't know it's true until you do it yourself. So, you know, there's an example. I was talking to a friend and she said, "Um, yeah, I you know, I I um I just got I broke up with my boyfriend.
40:27Um, he's a narcissist." And I was like, "Oh, man, that's that's hard. Like, I've dealt with a narcissist before." Um, but I said like, "But imagine if like I had known he was a narcissist and I told you when you first started dating him. Would you have stopped dating him?" And she's like, "Well, no, cuz I wouldn't know what a narcissist what being with a narcissist is like." And so, it's one of those things where like someone can tell you that something sucks, but it's really hard to read about something and truly understand it. And so, like all
40:57the things he said about making money, that it's isolating, that it warps people's perception of you, that in many ways it makes your life more complicated and negative and complex to manage. All those things were true. But him telling me didn't register.
41:15Yeah. You kind of had to find out for yourself.
41:18Right. I I think that's that's so true for for pretty much anything. And it's like there there's been things in my life where like I I really wanted them.
41:28I had this strong desire in the back of my head. Then it it's like I have I have to actually get them to realize that I didn't really want them that much in the first place or it's like they don't fill the hole that I thought they'd fill. But like you have to get to that place to know that for sure. And then I I think if you don't it if you think oh no I I just like I I just don't want this thing and then you stop pursuing it. There's always going to be that desire in the back of your head and then you're not going to fully get rid of it.
41:54Yeah. I remember I really wanted to um buy a Porsche.
41:59And it was like this thing ever since I was a kid. I remember my friend's dad owned a Porsche. She was like a successful guy and he had this beautiful black 99 I don't know 99 I don't know what what model it was. It was in the '90s. Um and uh I just always had it in my head that I wanted it. I always put it on my mood board or not my mood board, my like vision board or whatever when I was a kid. And then I bought bought a Porsche and I got in it and I was like, "Whoa, the seats are really
42:27low and like, whoa, it's really rattly and like it's really loud and man, the stereo is not that good." You know, it's like all these things where I was, wait, the car I had before that isn't as fancy was like better in so many ways.
42:42And I I thought like, oh, girls, like girls are going to love me having a Porsche. I mean, great. I realized like girls don't care about you having a Porsche. And in fact, the only people you get attention from are middle-aged men. You know, it's like some 65-year-old dude who's like, "Oh, nice car, kid." Um, so I think like Morgan Hel has this great line where he's like people think that they they want uh what is it? It's like uh money or no,
43:08freedom, uh freedom, respect, and love.
43:13And they don't realize that none of those things are related to money. That you can get all those things without money. And so it's like for me I definitely had this feeling of like okay I'm gonna make a bunch of money and then have this awesome life and then I got a lot of money and it was like wait like no no no like having an awesome life actually comes from like cultivating an amazing group of friends hosting events like think going to the gym and bringing groups of people together like it it's not it's not about having any money at
43:43all. In fact it's almost antithetical to money. Um, and so it's kind of this great irony that so many, especially young men are like, I need to make money so I can get all these things I want. And it's like, no, you don't. You don't need it. But you kind of have to go on the journey to realize that.
43:59Yeah. What do you think was the dumbest thing you spend your money on when you first started to make money in your 20s?
44:05I mean, I would just spend money because I could. Like it was so shocking to me that I could walk into a store and spend like $5,000 and buy a new TV that I would just like every year I'd just be like, "Oh, I'll get a new TV. I'll get a new camera." I just endless gadgets and computers and all that kind of stuff.
44:25Probably the dumbest thing I ever bought was a Segway. I bought like one of those Segways cuz I was like, "They're cool." And then I realized it looks horrible and it's like ridiculous thing to like one the one that was kind like a scooter.
44:37Yeah. But I don't know. I mean, you realize pretty quickly that money, buying things is only satisfying if you have a deep need for it. Like it has a real utility, right?
44:49Or um if you worked really hard for it.
44:53So it becomes it's not about the thing you bought, it's about the symbol. So I remember um I bought my first BMW and that was like I'd never owned a nice car before and that was like every time I drove the BMW, I'd be like I earned this. like this is from all the work I did over the last 3 years and that felt really good. But then buying the Porsche was like no, it doesn't mean anything.
45:14You know, it's too easy. It's like uh you know, you could win a gold medal and like work for like 10 years to become an Olympian or you could buy one on eBay and if you go buy it on eBay, it's no fun, right? And so the moment that buying things becomes easy, it's not really enjoyable anymore.
45:29No, that that definitely makes sense and I can definitely relate to what you're saying about the BMW, too. Like I remember I bought bought this Mercedes a few months ago and then every time every time I saw that car for like the first month, it reminded me like, oh yeah, I worked so hard the past year for this and then it was just a nice nice reminder of like how um how how hard I worked. So that felt great, but then it's like after that the feeling starts to go away when you probably just go, "Oh, now I want the newer Mercedes or I want the better Mercedes or whatever."
45:58And that that never really ends, you know?
46:02that doesn't go away. And and so I think like part of for me like definitely over the last 5 or 10 years I've realized like no matter what there's always this itch for more and there's no perfect amount of more. You know, you can never satisfy. It's like it's like ice cream.
46:17You don't eat ice cream and then go I never want more ice cream. You know, you just keep being hungry. And so at a certain point you have to just stop and realize that it doesn't doesn't do it for you. doesn't mean you can't enjoy an occasional bowl of ice cream, but you really don't want to become an ice cream addict.
46:33How how have you trained yourself to stop? Or how have you trained your mind to be be more aware of it and be better with it?
46:47Well, I think um it's like candy. Like I remember when I was a kid, I would eat an entire bag of Skittles. You know, like when you go to a movie, there's a massive bag of Skittles. I found that you feel really ill afterwards, right?
46:58So, I think part of it is being gluttonous and doing the thing and realizing it doesn't make you feel good. Interestingly, the thing that really made me stop spending money was medicating my ADHD because I don't feel a lot of people who are drug addicts or um shopping addicts or sex addicts. There's something about their dopamine system where they feel this desperate need to dopamine seek and get that hit.
47:24And I think for me, I spent a lot of time um you know, buying random things or or starting new businesses or whatever because my dopamine system is [ __ ] up. And so I found the moment I started taking Viveance, I don't feel that anymore. I don't feel like I need to go and you know impulse shop, which is really interesting. So it's a bit sad to be like I don't know that you can train yourself out of it. I think you can kind of like if this is your default, I think you can shift your
47:54default a little bit, but it's hard to take it like this without medication.
47:59Like if you're a highly anxious person, you can meditate and meditation will take your anxiety down a little bit, but it's never going to turn it off. It's never going to get it really far down, right? Cuz your set point is like here. And I think part of that's just accepting like you have a problem with anxiety and you have problem with ADHD. It's like that's the first step.
48:19Totally. Well, and again, it's like there's a lot of those things are vitamins, not painkillers. Like they help, but they don't solve. And I just found taking the pill for ADHD was like complete revelation. Like my anxiety used to be a seven out of 10 like all the time. And now it's like a 1 out of 10 probably. And that's 100% been medicating the ADHD. And that's shocking to me, right? because I spent so much time neurotically thinking about all the
48:49things that I could do. Okay, if I just eat right and I meditate and I go in the sauna and I use a Vegas nerve stimulator and I do a cold shower, you know, you start building this checklist.
48:59I think the stress of that is like so bad for you as well.
49:02Totally. Well, yeah. You're just constantly I mean I look I look at my gray hairs that have come in and I look and I'm like, "Okay, I bet I'd have like half the number of gray hairs if I just been medicated earlier. inspiring me to try it out.
49:16Oh, dude, you got to. I mean, if you have ADHD, it's like, why wouldn't you?
49:22Yeah, I'll definitely definitely be giving it a try. For sure. So, one one tweet that I saw that I I thought was super interesting was you said, "Having the courage to be disliked is the greatest trait of successful entrepreneurs," or something along those lines. Well, I would say it's um mostly a trade of happy people. of happy people.
49:43Happy people and great entrepreneurs. I think to be an entrepreneur, you have to endure people thinking you're an idiot for a while. Like my, you know, my parents definitely were kind of like, okay, like are you paying your taxes? Like what's going on? What's this business you're doing? Like should you go get a job for the first five, even 10 years? Um, and you get a lot of people, you feel like an idiot. I mean, I certainly did. Like I remember my friends were all going to university and they were all learning about cool
50:13interesting things and partying and having all these neat experiences and going backpacking and I was working and I was like, man, I'm like missing out.
50:21What am I doing? Like, but then when they graduated university, I own my own house, right? And it was like, okay, that that worked. Um, so I think um, having the courage to deal with that discomfort and having people criticize you a little bit is really important. That also applies in your personal life. So, I don't know.
50:43I mean, let's say that you're let's use an example. Let's say you're gay, right?
50:48And uh, it's 1985. Very inconvenient time to be gay, right? It's not you're AIDS, people are scared of you. It's accepted, but it's not totally accepted, right? It's still kind of underground. you don't tell your family, whatever.
51:02Are you going to have a happier life if you're closeted or you're openly gay?
51:06Right? I would argue probably you're going to have a way happier life if you're openly gay, but you're going to be disliked. It's going to be miserable in a lot of ways. And I think having the courage to choose that harder path and be out about whatever belief it is you have or however you want to live your life is really important to your own happiness. And I know a lot of people who don't don't do the thing they authentically want to do because they worry about shame and judgment from
51:36society. Do you think there was a point where you were you were holding off making certain big decisions or you were holding yourself back a bit because you're scared what people thought?
51:48Yeah, tons. I mean, I started a business um in 2009 that was a project management software. And it was kind of like a sauna before a sauna came out. Um, and I decided that I would bootstrap it. I'd find it all myself. And for years, year after year, you know, first couple years it was growing a lot. And then I started flatlining and slowly not, you know, not doing very well. And I just, my ego wouldn't allow me to shut it down and
52:17admit defeat. I just kept pumping in $100,000 a month every month. And that's a lot of money. That's a lot of money for a little bit of embarrassment. But I couldn't address the fact that it wasn't working. And I would argue with Chris, my business partner, and say, "No, this is going to be a $100 million business and all this stuff." But there was no evidence for that. I just was protecting my ego. And so I ended up losing over $10 million because I couldn't I didn't
52:46have the courage to be disliked and make a hard decision. And I think that same thing applied a lot with working with the wrong people, hiring friends. I mean, I didn't fire anyone for the first 6 years of the business ever. People left or, you know, like people would kind of like transition out or whatever, but I never sat down face to face with someone who needed to be fired and fired them. And that was cuz I didn't want to be disliked. I'm a people pleaser. So,
53:14for me, I've really had to work on having boundaries and asserting those things and realizing that there's a there's a really great quote on this. Um, it's easy choices, hard life, hard choices, easy life. And I think that sums it up perfectly that often if you choose the easy path, you're going to have more misery in the long term.
53:36Yeah. Yeah. [ __ ] I I definitely struggle with that as well. I like that's that's one thing I I've been noticing lately now that I've been running my own business and now now that I've started to hire people like my people pleasing brain and like the people pleasing part of me is is really starting to come out. So that's definitely been a huge thing I've been working on lately. And what what were like the first steps that you took or how how did you get better with the people pleasing side of things
54:04especially in business? So what I did is one I you know you fire your first person and it's horrible and then but you realize like you know the world didn't end right. So for me I think I I fired per somebody in like 2012 or something. I started my business in 2006 so it was a long time. I finally did it and it was a friend and I sat down and I said, "Hey man, I realized I could frame it in an empathetic way." Yeah. And I
54:32said, "I care about our friendship and our friendship is being damaged. It's more our friendship is more important than working together and our friendship is being damaged." And I think that even though it was hard and, you know, it wasn't an easy conversation, I think in the long run I was honest and he understood even though he's a bit pissed in the moment and I realized that, you know, it was okay. And so you can I would slowly over time get comfortable with having hard conversations with
54:59people. Yeah. And sometimes I had people who were complete [ __ ] right? Like where I'd have a hard conversation, not firing someone, but just negotiating something or having boundaries and they would blow up. And I was over time able to get comfortable with that and deal with it. And I I think it took me until two or three years ago, I actually went to therapy to try and learn how to say no to people because I would get someone that would text me and they'd say, "Please, can we go for coffee?" or what,
55:27you know, whatever it is. And I go for coffee with lots of people, but there's some people I just I just don't want to or I don't have time or I'm too busy or whatever it is. And I couldn't say no. I always say, "Oh, maybe in a month or whatever." And then a month later I'd be dealing with it or whatever. And so I really had to work on myself just to be able to say like no or like I can't, you know, which is awkward if you're a people pleaser.
55:51So it's been a journey, a 20-year journey to learn how to say no.
55:54Yeah. So dealing dealing with it mainly through exposure, right?
55:58Totally. One one trick if you're really struggling with it is there's a pill called a beta blocker. Yeah.
56:04Which people take for public speaking or for anxiety. And when you take a beta blocker, your body doesn't have the physiological response to anxiety that you normally would. So, you know, when you're like stressed out, let's say you're like in a room with a tiger, your heart's going to start pounding. Your palms are going to start sweating.
56:21You're really scared. If you take a beta blocker, you'll have no reaction. You might mentally be like, "Oh my god, there's a tiger. I need to be careful."
56:28But you won't have that physiological reaction. And so, what I've done a few times is when I have difficult people I'm dealing with, I'll take a beta blocker. And they've done studies where if people are scared of spiders, for example, they'll give them a beta blocker and then they'll put spiders on their arms and after they do that, they're not scared anymore. So, it's a neat trick for people that are really really intimidated by these difficult conversations.
56:51Interesting. Really interesting. And so you said you you said earlier how for maybe the first 5 10 years of your business, your parents were telling you to go get a job or they they were being kind of doubtful of that. Like it it actually lasts like 5 10 years, right?
57:12Yeah. I wouldn't say they were saying go get a job, but it was definitely like um they're nervous about it. They're nervous about will I be okay?
57:20Am I going to be financially stable? Am I going to blow up?
57:24Wow. And how how did you deal how did you deal with that back then? Because you started finding success pretty quickly in business, right?
57:34Yeah. I mean, I think once they saw it's interesting, I think like people are quite simple. It's like their perception of wealth is usually like, do you drive a nice car and do you have a nice house?
57:45Right. And so I feel like my parents, it was like as they'd come over to my house and my house is nice, they'd be like, "Okay, like he couldn't have a house unless things were kind of okay, right?"
57:54So it was real. But um my dad my dad had his own business and he really struggled with it and he almost went bankrupt. So I think he just applied all of his anxiety to me. He just didn't want that for me. So, he was always saying like like I remember I called my dad like two years in or three years in and I was like, "Dad, we just I filed my or I just did my year end. I made $250,000 of profit." And he goes, "Oh my god, did did you pay the taxes?" Like, that was the first thing he thinks of, not, "Wow,
58:24son, congratulations. I'm so proud of you." And I don't, you know, it's not like he's a jerk or something. It's just he was so tuned for anxiety. Business equals stress equals risk. So, um, it took a while for him to calm down.
58:38Right. Right. And I I think that's that's also a huge thing that everybody has to deal with, just people people in their lives and maybe maybe they don't necessarily doubt them, but it's like maybe they're just worried. They they they have anxiety for them. And and I I think like it's like it's so important to it's important to listen when you have people like that, but also I think not taking the anxiety and the worry and the doubt to heart. Totally. Well, I
59:07think um you know, everyone's got their there's a story or there's a great Francis Ford Copela quote. It's um the story of the father is embedded in the sun. So for me it's like my dad he kind of um struggled in business and I was like I'm not going to struggle in business but then his fear from that plays out in his in his reaction to it right but he created me. The reason I'm even interested in business is because I saw him run a business and he'd always
59:36talk about business and I helped him you know I would always go to work with him and like you know I have all these affinities for it. Um, so it's interesting to see that play out over and over again with fathers and sons and mothers and daughters and all that kind of stuff. Yeah. So, one of your one of your tweets that I found was really interesting was you said actually I'll I'll pull it up right now, but you said there were two skills that were
1:00:05essential for having success in business and they weren't knowing accounting or spreadsheets. They were one psychology and then two it was dealing with tough people some something along those lines.
1:00:20Can't find it here on my phone but I I really want you to go into the first one psychology. So what do you think are some of the some of the psychological biases or some of the things that you learned psychology-wise that have really helped you in business? Well, mostly it's been spotting my own poor thinking, right? So, for example, um sunk cost, right? So, the example I gave earlier
1:00:49of, well, I've already put $5 million into this failing software business. I might as well keep going, right? I' I've already I'm already too too far deep, right? There's this study where they would um what was it? It was like they'll someone is more likely to go see a movie they don't want to see if they already have a ticket even though they'd be happier just lighting the money on fire and doing the other thing. And I think a lot of people do that in business um with projects or businesses they've started where they've told all
1:01:19their friends that they're going to go do this thing and it's like it forces them to do it. And that can be really positive. Like I often do that whenever I'm starting a new business. I talk about it. I make it real. I give it momentum. I tell I tell all my friends to force me to do it. But that can also be very dangerous on the flip side because it can lock you into doing something you don't want to do. And you won't stop because you know, oh, I told I told my parents I was going to be a CPA, so I can't quit accounting school.
1:01:46I'm going to let them down. Right? Those things. Um, one thing that um one thing that um is also incredibly powerful is anchoring. So, if you go in, let's say like um let's say somebody comes to you and they say, um, I'm selling, let's say this microphone. I'm selling you this microphone, right?
1:02:10If I talk, if I start the negotiation, let's say the microphone's worth, I don't know, $1,000. I go in and I say, "Sam, I want $3,000 for this microphone, right?" You're like, "Dude, what the hell? That's crazy. like the most I would ever pay is 1,500 bucks because I said 3,000. You never would have said 1,500 bucks. You probably would have said you'll pay 300 bucks for it. But I've anchored you at 3,000, right? And I find that's very powerful for
1:02:38negotiation. I I think of these things at dark art, so I try not to use them unless they're for good, but I often see these things being done to me. And what's crazy is Daniel Conaman, who's probably the most famous um uh scientist in this space, who did all like so many of these studies, he famously said that he knows them all, but he's still vulnerable to them. So, I think like what's crazy about um some of these uh some of these uh heristics and stuff is
1:03:07like you can know them, but the dark arts will still work on you. Right.
1:03:12Right. Well, well, because I think they're so embedded into our psychology. So, like another one is like contrast, right? So, let's say um let's say I'm a realtor. Um I take you to three houses. I take you to an incredibly fancy house you can't afford. That's that's way too nice.
1:03:28I take you to an absolute [ __ ] hole that is horrible that you never want to live in. And then I take you to one house that's okay. You're going to think the house that's okay is amazing, right? Cuz I've anchored you. I put your hand in cold water, then I put your hand in hot water, then I put your hand in warm water, and you're like, "Oh, yeah. This is this is just right." So that contrast forces you to make bad decisions sometimes or think like, "Well, that's all that's out there." You know, like these are these are like I think part of
1:03:57why understanding psychology is so important is because a when you're in business, you're going to deal with a lot of employees and employees need to ensure that they're you need to ensure your um employees are happy and they feel taken care of. Um and a lot of that is obviously psychology, but then also you're going to have practitioners of the dark arts like psychopaths and narcissists who you're going to be doing business with. and you need to know, you need to be able to see through the tricks and see through all the things
1:04:27that they're going to do. Um, and don't get me wrong, there's lots of wonderful business people out there, but you're going to deal with very difficult people at some point. And knowing how to deal with them is very important. So, I find for me personally, I think part of the reason might be the fact that I grew up here in Victoria and a lot of people seem to seem to be very trusting, but I find I'm way too quick to trust people and I'm a very naturally trusting person, which works well until it
1:04:56doesn't. And it's like there's always going to be those bad people in life and especially especially in business. So, how do you how do you figure out who those people are from the start to just avoid them completely or like what are some red flags that you that you watch out for or you've learned about from experience?
1:05:15So, I'm the exact same way. Um I remember watching like um I'd watch like superhero movies and there always be like the evil bad guy or like you know um in like Harry Potter like Voldemort, right? And I'd always my take was always like oh there's no such thing as bad people. There's just misunderstood people, right? There's no I'd never witnessed evil. Um, and I heard the word psychopath, but I didn't really know what it I didn't really know what it meant. I thought maybe it's like someone who's crazy, like Hannibal or like a
1:05:43serial killer or whatever. And the reality is is that psychopaths are it's about 5% of the population, but it's but it's a it's a um there's a there's a very wide swath of degrees of it. Now on the extreme extreme extreme degree you have serial killers but that's like a tiny percentage of psychopaths. Most psychopaths are totally normal people who exist in day-to-day world but they
1:06:12just feel zero empathy for others or or varying levels of empathy. And in a lot of ways, it's like a superpower in business because they can basically manipulate people or or mess with people and do and feel absolutely no consequences whatsoever. Where if you or I did that, you know, we chisel someone or, you know, charge someone too much or do something horrible and unethical or insert something into a contract, we would just feel guilty and horrible.
1:06:39Like it would be really negative for us, right? So these people generally because they're like because they're so um they feel no empathy, they can rise very quickly and they can be very impressive.
1:06:52Um and they usually are not the most successful because generally society does not reward these people in the long term. Um but they're really freaky because they can be highly manipulative and they can um you know convince you to do things that are against your interest. And so for me, I was incredibly trusting. I was going through a period of high anxiety. I was very stressed out at work. And I met this guy um who uh was really charming and and
1:07:22helped us out with a bunch of projects.
1:07:24And I don't know, I I can't I'm not a psychologist. I can't diagnose. I have no idea. But I just say like I felt he was um you know, not a good not a good guy and was not truth truthful about a lot of what he told us. And so I learned the hard way that there are bad people out there or that there are people that will lie or be Machavevelian and all this kind of stuff. And so um I think you kind of have to learn just like the
1:07:53narcissist example, right? If I if I told you like beware of narcissists, you know, you probably won't know what to look for or even care. If you date a narcissist or you do business with a narcissist, you'll learn pretty quick not to do that again. And I feel like I've had enough experiences in business that I can start to see certain archetypes of people and just go like, "Oh, I don't want that pain again."
1:08:16Right. And you might get lucky. You might just trust people your whole life and you probably will mostly get lucky.
1:08:22But it's like you don't want to rely on that.
1:08:24No. But but so for me, where I came to was um trust but verify. So, for example, you know, if you're going to do business with somebody, um, call the people that they work with that they don't put on their references. Don't take their version of events, uh, as true. If they say, "Oh, my last company, the reason I left was cuz my co-founder was a terrible, terrible individual, you know, whatever." Um, and they're vague
1:08:53about it, you know, you might want to call that co-founder and sus it out and just see what they say. Um, you might want to look in the the court registry and see if they've been sued before. Um, you know, if they've worked a bunch of jobs, you want to call the references that they don't give you, not the ones they do give you. So, we do like a much more extensive process of background checking and sussing people out before we do business with them or before we hire them. Um, and that has come out of just the experience of getting our hands
1:09:21burned so many times that, you know, it's uh it's no fun. But life goes on usually, you know.
1:09:30If you if you could go back to when you first started doing business with with that guy, I remember you spoke about him him in the book. What do you think you'd look out for or what what red flags do you think were there that you might have ignored?
1:09:46Well, in that particular this is this that's actually a different one. There's so many characters that we've dealt with over the years. The one in the story, uh, in my book, this, uh, guy named Brian, um, the red flags there were, um, he showed no emotion or sorry, no no authentic emotion. So, that's going to sound funny, but it's like he was never nervous. He always had an answer for everything. He didn't sweat. He wasn't uh he he I really when I do business
1:10:15with people or I hire someone now, I really look for authentic emotion. So, I want the person in the meeting to have their hands sweating and they're a bit nervous or they give the wrong answer or oh, I feel dumb or they're blushing or whatever because a psychopath um or a narcissist or any of these characters um they don't usually exhibit those signs.
1:10:36They have such high confidence in themselves or they feel so little stress about things that they don't show those things. And so when someone's too shiny, when someone's too impressive, when they're too silver tonged, when they always say the right thing, I'm always a bit nervous. Uh, and it doesn't mean, don't get me wrong, I've worked with lots of people who are just like so charming. But where I want to see them is I want to break past that and I want to see their their warm gooey center at some point, right? So there's people that like, you know, you could
1:11:05talk to them 10 times and they're like so on, but then eventually they're like, "Oh man, like you know, I'm really struggling with my girlfriend or there's something deeper going on." Or, you know, you see their soft spot. I always want to see people's soft spot to see that they're like human, right? And it it makes you trust them more. And I Yeah, I'd say I definitely I definitely see where you're coming from. And once I remember I was speaking to someone and they were like, "Yeah, I'm actually I'm just in business to make money. Like I
1:11:34don't really want to help people out."
1:11:35And just hearing that, even though that technically wasn't the correct answer, like the more socially acceptable thing would be like, "Oh, I'd love to help everyone." Like hearing that made me trust them so much more. Totally. I think that is uh actually an interesting example of like somebody saying something where I mean you got to be careful. So, one one thing with a someone who's psychopathic is they might say um have you ever seen like Good Fellas or like mafia movies? I have.
1:12:00Yeah. There's always like a scene where the mobsters are telling a joke and it's like a horrific joke that a normal person would never say, right? It's murdering someone or they're talking, you know, saying something really dark.
1:12:11Those sorts of things are always good tells for someone who's a psycho because they say a thing that they don't realize is crazy or or or that's dark, right?
1:12:20Like they laugh about it. They laugh too hard at a really horrible joke about, you know, somebody's misfortune or whatever it is. And it's like cuz they don't have the empathy. And so I think like the the money example is so interesting cuz it's like they could they could be saying that in a cold way or they could be saying like you know what like to be honest I just care about making money and like what I would be curious to pull on is well why you know did they grow up poor? Did their parents fight about money? Did they really want
1:12:48to buy a house for their mom or is it truly that they're like, I just want to be rich and powerful and I want to control people and I want to be a, you know, fund corrupt politicians. It's like those are two different options from the same answer, but one is much more uh humanistic.
1:13:05Why do you want to make money?
1:13:08Well, the answer I always give is that my parents fought about money when I was a kid and so I just wanted everyone to stop fighting. Um, separate from that, you know, I would the most I would fight with my mom would be she would tell me what to do. She wanted me to clean my room. I don't want to clean my room. She wants me to do the dishes. I don't want to do the dishes. And I'm incredibly stubborn. And so to me, money represented the ability to not have to do the things I didn't want to do. Um, and so for me, it was really like
1:13:37freedom and then wanting to take care of my family. Um, and ironically, I'd say like, you know, I was able to take care of my parents and and do some of those things, but I wouldn't say it necessarily solved anything. You know, in fact, it makes life kind of more complicated with family and money and all that kind of stuff.
1:13:56Did that did that motivation change over time? Like, was that was there a reason why you wanted success or why you wanted money at the beginning that went away or maybe something replaced it?
1:14:08Oh, man. I mean, I think like every young guy who's in business is like, "If I get a nice car, girls will notice me."
1:14:15You know? It's like there's always that that part of you. Um, I'd say that was definitely a piece. Um, and then it was like, man, I want all the I want all the stuff that the rich kids I knew growing up had, right? So, it's like, oh, I want to like I want a nice car. I want a nice house. I want to be able to go on a trip to Whistler or go to Maui or, you know, these things. Um, and over time I realized like, you know, those things are those things are nice, but they're not that meaningful. And I'd say I just
1:14:42cared a lot less about all that stuff. I don't know, like I don't I don't work for money right now. I work because I find it interesting and fun and I get to meet great people and manifest ideas.
1:14:57Uh, and that's very different from the early days. In the early days, if you told me that if I worked, you know, eight hours on something I didn't enjoy and I could make $5,000, I would jump in a second because I was very money motivated.
1:15:13Well, I I I think that's that's really interesting because that that comes from freedom as well. It's like now you've got the freedom to do the stuff you enjoy.
1:15:23Yeah. going back to what we were talking about before with like being motivated to help people out or or or or like wait no never mind um let me let me redo that. So so going going back to what we were talking about before like some someone saying like oh I'm just starting my business to help people or like I I'm just starting this to make money. I saw one of your tweets. You were talking to this guy who ran their own marketing
1:15:53agency and they they were saying how they love to help nonprofits or their marketing agency is built to help struggling businesses and then you're saying no, focus on focus on the profits now and then help people long term. Have your thoughts in that conversation changed at all?
1:16:13No. I mean I um I meet a lot of people where they say something like um you know I think in that example it was like someone who ran a marketing agency and they were saying like I really want to work with small local businesses and nonprofits cuz they're the people that need the help most. And I said, well, um, you know, why not work with the biggest possible companies and then just donate, you know, donate money or time to those organizations, right? Like, if you have the capability, let's say that you can either help, I don't know, let's
1:16:42say you can work with five nonprofits, you'll be broke most of the time. You'll barely make any money because you can't charge that much. You're trying to do a good thing or whatever. you'll help five nonprofits and maybe every year you'll make, you know, 500 grand and then your profit will be 50 grand and you'll live off the 50 grand or whatever. Or you can scale up your marketing agency. You can work, you can make $5 million a year.
1:17:06You can work with startups or bigger companies or whatever. And then you can make $2 million of profit and you can decide what to do with the $2 million of profit. And if you're you really believe in helping people, you can use the full $2 million to go and help people. and you have a secure functioning business that has profits that'll survive downturns where you can pay people really well, etc., etc. I'm a big fan of using capitalism to do good. And I don't
1:17:35think that you need to make money in a way that's necessarily like kumbaya, right? It should not do anything bad in the world. Your product should not rip anyone off or be negative. But I don't think that, you know, there's anything wrong with just making a hell of a lot of money from business and then giving it away or doing the philanthropic projects that you want to do. And so that was the advice I gave them. It's like the saying you can't pour out of an empty bucket.
1:18:01How did your dating life change after you started to make money?
1:18:06Well, I didn't really do much dating, honestly, when I was I I I kind of uh I was a serial monogamist. I was in a series of long-term relationships in the 20s and I I don't know. I mean, I I wouldn't say it's funny like you realize pretty quickly that um you know, girls don't notice cars. Um you can't really go around saying like, "Hey, I'm a really successful, wealthy
1:18:36guy unless you want to be an asshole."
1:18:38And so there's kind of this thing of like, well, how do you communicate your value?
1:18:42And I remember I would go to this I used to go to this club all the time and my friend was the DJ and girls would be going crazy for the DJ and you look at it and it's like this guy's getting paid in like free beer and like $30 for per night but he's on stage and he's DJing or whatever and the girls are crazy about him and I'd be sitting there going man like you know I've got all these businesses and I've got so much to offer and no one knows. And uh I think that's
1:19:10kind of the hilarious conundrum. I know so many very wealthy, successful guys where they can't meet women because there's no way for them to communicate that. And I I realized for me um ultimately the way that I had success with dating was building my own confidence and being an interesting person. And so, you know, being able to have a diverse friend group and be able to meet a girl and invite her out to an event or something like that and be emotionally um intimate and curious with
1:19:39somebody and ask questions, I realized that's the route to a woman's heart, not impressing her with a fancy car or wealth or something like that. And so as soon as I um got the confidence to just like see a beautiful girl and walk up to her and ask her a lot of questions and and then not appear as a creep and have a nice life, that went a long way. Um but I never experienced like certainly not in Victoria any kind of like um you know girls girls showing interest just
1:20:09because of who I was.
1:20:12Did did you have to work to develop that confidence or was the confidence with women something you've always had? Well, I um my mom um my we didn't my mom really wanted a girl and didn't have a girl and so she always talk to us about emotional stuff, right? um not not that you know a mother wouldn't but my mom was very open and so I learned early to get good at talking to adults and and to women and so I'd always talked to my friends moms or whatever and I always
1:20:40got along really well with women and so for me it was never a problem at all like I've always been very good on first dates and stuff what I struggled with was being in a bar and seeing a girl and having the guts to go and say hello and I think the Most I always found like if I was in a social group, let's say I went to a dinner and you know some beautiful girl came and she's a mutual friend, I would have no problem connecting with her, asking for her number, all that kind of stuff. But if I
1:21:10was in a bar and I saw a girl, I I remember like when I was newly single, when I was 22, um I was in a bar and this girl looked at me and she like flipped her hair and it was kind of like looking over at me. And I was literally going in my head, "Oh, I wonder if she'll come over and talk to me." You know, it's like I just had no idea what the rules of engagement were. And so I had to learn how to go up and say something and, you know, get to the point of being able to talk. And then once I could talk, I was fine. But that
1:21:40was uh that was challenging.
1:21:42And I feel like part of that is like being okay with being embarrassed and saying something stupid.
1:21:47Totally. Well, it's crazy like I still I still struggle with this even just if I'm on a let's say I'm on a plane and I get seated next to someone just a dude or or anyone I want to talk to.
1:21:58I'm in I'm still I still have that little tiny bit of social anxiety of like, oh [ __ ] like if I don't say something the moment I sit down, it's weird if I say something later. And what if they don't want to talk to me? And what if I get rejected? And I think one of the most impressive traits I see in friends of mine is the people that can go to a cafe and just no matter who's standing next to them, they can like start talking to them, make them laugh, ma, male or female, just just like making friends and being social, I think is such a great quality. And it's
1:22:27something that I really try and work on myself of just like always talking to the person next to me no matter what.
1:22:33Yeah, I think that's so important. And sometimes you get rejected. I went to a a workout class um recently and there's this woman and I wasn't flirting with her at all. She was just just standing next to me at the station and I said, "Oh, you know, what do you do and what are you up to today?" And it was so clear she didn't want me to talk to her.
1:22:52She just kind of was like not into it at all. And it was a little embarrassing for me and a bit uncomfortable, but like yeah, I'm glad I still did it, you know?
1:23:00I think a lot of that is like having the having the victory with yourself like being able to overcome your fear and your social anxiety, fear of embarrassment, etc. So, it's like even if you are rejected, even if like the interaction doesn't go anywhere, like you still you still got over your fear and you still won mentally. Well, and also if if someone I remember there was this girl I was out at a bar and I walked over to this girl and said hi and
1:23:29she just looked at me and she just said [ __ ] off, right? No joke.
1:23:34No joke. And I I was like whoa. Like I you know I I definitely been rejected like that and just walked away and been like whoa. Okay. But with her I was like whoa like that was harsh. Like are you okay? Like are you having a bad night?
1:23:48And then she actually softened towards me. It was like, "Yeah, like sorry. I'm sorry. Like my friend, you know, my friend did this and we're fighting and I'm sorry I shouldn't have done that." I ended up talking to her all night, you know, and it's like the I feel like um often when people are harsh, it's cuz they are having a bad time or or think about it. Think about how annoying it would be if you were a beautiful woman and you're at a bar and annoying guys.
1:24:13is you're just trying to have fun with your friends and every 30 seconds some dork comes over trying to say an open, you know, an opener or something like that. So, I think I get it. I think um usually people have a reason or they're going through something. Um so, fair enough.
1:24:28Totally. Yeah. Just that's that's a great way to put it. Understanding people more, putting yourself in other people's shoes. And I was I was seeing a real about that a few days ago, which which was super interesting. the guy was talking about how it's important to always be viewing situations from the other person's point of view. It's like that's that's so simple, but just asking like trying to figure out how they're feeling and then feel those same emotions. When there's been times like I'd say like once a month I'll be sitting at a coffee shop and someone has
1:24:58like seen me on my first millad or something and it's always like it's always fun, right? It's always like some some you know business nerd comes over or whatever. But there's been times where I'm like in the middle of something or I'm talking to my girlfriend or I'm stressed out about a problem and I'm kind of like, "Hey, hey, you know, nice to meet you, but I'm kind of abrupt or whatever." And it's like, yeah, like everyone has those moments where it's just bad timing or whatever, right? But yeah, I think like learning to overcome rejection is very important
1:25:26for dating because you never know who you never know where you're going to meet your future partner. Like I have so many friends where they have amazing partners and they met their wife at the grocery store, you know.
1:25:38I met my girlfriend at uh she was working, she's a server and I started talking to her and we just hit it off and here we are now she's pregnant with our baby.
1:25:49Well, congrats. Oh, that's amazing, man.
1:25:52Love to hear it. And something something you were saying a couple days ago, actually, dinner was you you wish you were single for longer in your 20s.
1:26:01Mhm. and you wish you cut off relationships that you did that you knew were going to go anywhere sooner.
1:26:08I think um the people pleasing we talked about earlier and the work also applied to my personal life. Um so I wouldn't you know I think you pretty quickly know in a relationship in the first 6 to 12 months is this someone that I would actually really want to be with? Like the question I would always ask myself is like if she told me she was pregnant how would I feel about that? And there's girls that I've been with where I go, that would be okay. You know, it's not the end of the world. Like, she'd be a good mom and whatever. But I definitely
1:26:36dated some women where I was like, no, like that would ruin my life and like I don't want to be with this person and she'd be a terrible mother or whatever.
1:26:44And I wasted a lot of time with those people for whatever reason cuz I couldn't do the hard thing. I couldn't fire people. I couldn't end my relationships. Um, and so yeah, I do I do wish that I um just had more exposure and calibration. I think every person you date calibrates your system. And the more people you date, including the bad people, the more you get a sense of what the landscape is. And going back to
1:27:12anchoring, I started some of my early girlfriends, you know, there were great people in lots of ways, but there were we were a terrible match. And so my bar got set low, I think, in terms of what was a good relationship because those relationships were so hard that over the time in my 20s, I started dating people and they weren't great for me, but I was going, well, they're definitely better than that terrible relationship. So, you know, the psychology piece of anchoring
1:27:40and comparison definitely matters. And so I think getting as much experience as you possibly can from 18 to 25 or whatever and learning the the other the other counterbalance though is like you also need to have enough data to know what it's like to um I'm saying data like a business nerd but but um you need to know enough to also know uh how to be in a relationship. So, it's like if you're just dating people constantly, but you never know what it's like to
1:28:08live with someone or go through a hard thing with someone or be a good partner, that's also going to be a problem. So, it's a real dance. There's a great book on this called The Defining Decade by Meg J and it's all about how your 20s are this time where you're launching your plane and you're taking off. Let's say you're in New York. you're taking off and the difference between like 3° this way or 3° this way is is ending up in Tijana
1:28:36versus Seattle, right? And it's like you want to end up in Seattle, not Tijana. Uh maybe Tijana's nice, I don't know, but I've heard it's not very nice. Um yeah, so I think like paying attention to that, thinking really hard about your 20s is important.
1:28:52Are you happy with the way you spent your 20s?
1:28:56Yeah, because I mean it's the classic story of like, well, because I ended up here, right? It's like saying like, well, are you happy that your parents, you know, messed up in XYZ way? Most people say, well, yeah, that's hard, but I'm glad I I'm glad that that happened the way it did because now I'm the way I am and I'm happy about the way I am or it gives me these superpowers or gifts.
1:29:17So, yeah, I definitely am. Um, but I also look back and like roll my eyes and I'm like, "Wow, I can't believe I wasted so much time."
1:29:27And I I think like we're we're always going to make mistakes and even if like you looked back and maybe there were a few things that you could have changed or you could have done better, like the way that you spend that time is what made you now. There's one way doors and there's two-way doors. And I think most things are two-way doors, right? You can reverse them, including like getting married to the wrong person, right?
1:29:48Right? So, I got married, I got divorced. That's a two-way door, right?
1:29:52But, um, having permanent facial surgery or, um, you know, doing some crazy making a crazy decision you can't reverse. Um, that's something to really think about. And so, I think the nice thing about most of my mistakes in my 20s, they're reversible or things that you can change over time. Um, it's really the irreversible decisions like, you know, I decided to go skydiving and now I'm in a wheelchair that people regret. What do you think's been your biggest accomplishment that either other
1:30:22people can't see from the outside or the most people overlook?
1:30:28H well, I mean, the biggest accomplishment that I feel um well, there's the cheesy answer of like having kids, right? We were talking about this the other day at lunch with some people and um having kids. It's hilarious because it sounds so stupid when you tell this to someone who doesn't have kids usually, but there's something about it.
1:30:52If you think about all of our drivers in life, almost everything leads to sex or uh community or you know things that enable you to have a family, right? And we spend so much time thinking about that, but we don't make the connection that we need to that's our bi that's our biology driving us to have children. And so just like when you're starving, you know, you're like starving, you're starving, you're starving, you're driven to eat food, you eat food, you feel
1:31:22amazing, right? When you're starving and you finally eat food, you listen to your biology and your body feels really good.
1:31:28And so I found the moment that I held my son uh in my arms and I saw his face and it looked like my face, it was just the craziest thing. It was like someone had injected like MDMA into my brain. And the feeling I had was like, "Oh, none of this matters." Like none of the work, none of the maniacal um you know, desire to try and like make a dent in the universe or build a great business or any of these things, none of that mattered. the only thing was this
1:31:57little baby. And so that is this achievement that is not very exciting for people to hear because it's so boring. But when I hear people say they don't want kids, I'm always like, that's cool. Like, you know, you make your own choices, but it's such a great hack to feel that you've made this big accomplishment when, let's be real, you haven't. Most people have kids, and it's not really, you know, it's not impressive, but it does achieve the biological feeling of satisfaction that exceeds anything else. Like I remember
1:32:26my dad said, "My greatest accomplishment is having you boys." And I was like, "Dad, that is so lame." Like, "Are you kidding me?" And then now I get it. I totally get it. Um, so I'd say that is a big piece. Um, and then another one is just conquering anxiety. Um, I had so much anxiety for so long and I really lived in a prison of my own making where uh I would spend all my time, you know,
1:32:54obsessively worrying about business or a social situation at work or someone I had upset or maybe thinking I was going to die of a brain tumor or whatever it was. There's always something that I was really anxious about. and figuring that out and not feeling it anymore has been like the most profound achievement for me. And it's so funny looking at it and being like, you know, I've got this tweet that's like um most successful
1:33:22people are just an anxiety disorder harnessed for productivity. That was certainly me. Um so conquering that has been really meaningful for me and that that's been done mainly with the with the medication ironically, right? But it's like not hard. It's like take a little pill and that has really resolved it. And I I do wonder like you know you mentioned earlier that you have ADHD and it's like you know if you med if you medicate people worry that they'll like
1:33:52take away your fire or something and it's an interesting question.
1:33:55A worry of mine. Yeah.
1:33:57Well it's an interesting question. Let's say your fire is anxiety and it's like, okay, you can either let's say you can spend your 20s feeling really anxious and dissatisfied, but it'll it'll make you successful. Or you can just turn off the anxiety now, and you'll still be successful, but you won't be as successful. What's better? And like for me, I think if you told me that before I took the medication, I'd be like, "No, I don't want it." But now that I take the medication, I'm like, "Oh man." And like
1:34:27when people say um people will often say like um well you know what if the drugs turn out to like take years off your life, right? Let's say there's I just say I'd rather live 10 years less but not have anxiety than live an extra 20 years. You know, it's like it's so good to not feel that. Yeah. I think as much as much as I hate to admit it, like my my answer to that right now is like I just want to be dissatisfied my entire 20s and have the most success possible.
1:34:56And I'm I'm not too sure if like that's something that I I have to go through it, feel the pain, realize I made a mistake, and that's how I learn or I I just like admit admit that I'm wrong now.
1:35:12Well, it's hard cuz like five ants for example, it actually gives you motivation and it makes you want to focus and it makes you want to work. So, I wouldn't worry too much about that, but like I take an SSRI as well. And that kind of like yeah, it takes away the feeling the the driver a little bit.
1:35:30But I don't know. I think you should try Viveance, dude. I think you I think you'd really enjoy it. Got to give me one of yours.
1:35:39So, I saw I saw one of your tweets that was wait What was it? What was it again?
1:35:51Yeah. So, I I saw I saw one of your tweets where you were talking about you got this guy you got this guy to do a full psychological auton like asking all these questions, talking to everybody you knew. How did that turn out?
1:36:09It was fascinating. Um, so I have a friend um who's a investor and he said that the most impactful thing he's ever done in the last 10 years was working with this guy named Jack Sch who does what he calls the blueprint. And basically what he does is he does a whole bunch of like tests. So like you know psychological tests on you and then he spends like 6 hours interviewing you and then he interviews all of your
1:36:37friends. So it's like your sorry your friends and your co-workers anyone you spend a lot of time with and then they all talk about you and all you know what are your problems how can you improve. So it's like doing a 360 review on your life but then also taking into account all of your personality traits and you know all the data and stuff. And what came out of it was really interesting.
1:37:01Um my friends felt like I like so like you know let's say your friend calls you up and he's like hey will you help me move? Um I would probably be like oh no like I won't help you move but I'll hire I'll hire a mover for you. And it's like what my friend really wants is me to be like yeah dude I got you. Like I'll come and I'll do the hard thing. And um the way that he put it to me is he's like, you know, your friends want to mow the lawn with you and then have a cold beer
1:37:30afterwards, but you won't even you you will you'll never have the cold beer with them. You won't engage in that in that with them. So, there was this weird thing I was doing where I was distancing myself from people by not engaging and not rolling up my sleeves. And I thought that was really interesting. Um, and then there's a lot of stuff around my need to um, my kind of traits of people pleasing and stuff in my marriage where he was like, "Yeah, you're you're not acting like a king, you're acting like a
1:37:59stable boy. She's the queen and you're the stable boy." So, there's all these like fascinating dynamics that he was pulling out of my life from all the things I was telling him. And it ended up um it ended up making a for a lot of major changes in my life. You know, I realized that there's a lot of things I was doing that were not making me happy that also I was not happy in my relationship, which I already knew, but it was a kind of something that pushed
1:38:26me to separate. And uh it's crazy to look at like it was definitely this turning point in my life where I did it and I was horrible. Like I remember reading the document and just hearing all the negative things that people think about me and stuff, but there was a lot of truth in it and uh and it forced a lot of change and uh yeah, it was really it was quite impactful. What did you do to get rid of that emotional distance that you were creating with
1:38:54your friends and people around you?
1:38:56Well, I realized that um you know, to go back to the money thing, you know, people think that they're going to make, especially young men, it's like they think they're going to buy a nice car and buy a nice house and then they'll be like Vinnie Chase from Entourage. Like all of a sudden you'll have all these buddies and everything's going to be great and girls are going to like you.
1:39:14Um what I found was actually that people um view you as different. They view you as not like them because if you're wealthy and they're not, they feel um they feel like you're you're you're different. You're in another stratosphere. You're in another world. And it's very complicated. Like when you go out for dinner, let's say you have a lot of money and you go out for dinner with a friend and his girlfriend.
1:39:41Um if you don't pick up the check, you're kind of a prick cuz you can afford to. But if you do pick up the check, you're alphaanging him and you're saying, "What? You think I can't afford it?" Right? And so it's this thing where you're like, "Okay, well, I guess the answer is to not pick up the check and to split always, right?" And that would be an example of a very subtle thing that I would do to not create any kind of schism. I'd just be like, "Let's split. Let's keep it easy." Right? And maybe people think you're an [ __ ] for
1:40:09splitting even, right? Um another thing is like, um, you know, I've got a big nice house. I don't invite people over to my house unless I know them reasonably well because I don't want to color them thinking I'm like some wacky rich person, right? I just want to be a guy in a cafe who's nice and normal and talks to them like a human and then they can judge me and then maybe once they get to know me, sure, I'll bring them over to my house or whatever. And and you know, another
1:40:37example is like um I do um like trips with buddies sometimes and there's been times where I'm like, well, like I can afford it, so guys, let me upgrade our hotel. I'll I'll take you guys to an even nicer hotel. Let me pay for it.
1:40:52Creates a weird dynamic now. They feel like beholden to me and I'm paying more and it's kind of like I'm I'm, you know, at the top. We're not all equal. And so there's been a lot of lessons from those things where I remember when I um when I was in high school, I was always the kid that needed to bum bum a dollar, right?
1:41:12It's like, hey, can I can I borrow a dollar for a Coke? And I remember always thinking like, when I get rich, I'm going to be so generous. I'm going to like help all my friends and and pay for stuff and help people out. And you realize pretty quick that all those things actually really distance you from others. that unfortunately like hooking your friends up usually creates resentment and complexity. Um, and really you just want to be like a normal person.
1:41:39What do you what do you think is the balance of that? Because because it's it's like on one hand you want to do good for your friends. you you want to hook them up, you want to upgrade their hotel, but then it's like you don't want to be like the guy who's trying to alpha them or well, imagine how you feel if you know you're going through a hard time and your buddy goes, "Hey, man, and here's a,000 bucks for your rent." You might in that moment be like, "Wow, what a good friend."
1:42:06But you're going to start feeling a bit awkward pretty quick, right? you're going to start feeling like, [ __ ] like, do I, you know, I have to make sure he knows how thankful I am. And now, does he want the money back? And it starts to shift your dynamic a bit. You're a bit nervous when you see him. And you're always re reassuring him. Don't worry, I'm I'm working really hard and I'll get you your money back, right? Uh, you know, it's like all these weird dynamics can play out. And don't get me wrong, the lesson is not never help your
1:42:34friends, but it would be better in my opinion to secretly help your friend. So it's like, you know, you structure something so some random person that they barely know ends up being the person that hooks them up and get I haven't done this. I'm just making this up. But but like I don't think that it benefits relationships to insert money into them. I think you see this with families. So like people that have a lot of money, you can have the warmest, most lovely family. But if you have like a
1:43:02family cabin and there's three different families, like three different siblings, they'll fight over the cabin and how it gets dealt with or whatever. Or if the parents have money, they fight over the business or where the wealth goes or whatever it is. So I think like money in general is a toxic force for friendships and family. And you feel like you owe the person too. Like it might it might not be fully conscious but in the back in the back of your head it's like someone does something for you and it's like the law of reciprocity from influence.
1:43:32Yeah. You feel like you have to do something for them. So subconsciously you're kind of going to be walking on eggshells or trying to do them little favors etc. And I remember like a week a week or so ago I bought one of my friends like a pretty like expensive Christmas gift. And I I was like trying to do everything in my power to make them like not know it was me to like do it do it do it anonymously. But like the person told me like, "Oh, no. You got to you got to tell them yourself." And I was like, "Oh man, cuz I knew like that that's just going to make the dynamic so
1:44:02weird." Well, it's literally like the difference between you're here and then you do this. You just you just you kind of have one up them without meaning to. And it's it's a really awkward dynamic. And people always criticize rich people for hanging out with other rich people, right? They're always like, "Oh, it's all the all the rich people hang out."
1:44:19And you know why rich people hang out?
1:44:20Cuz the only people that they can talk about their problems with because they have rich people problems are other rich people. And the only people who there's no weird dynamic like that with where you can go out for dinner and not worry whether you're trying to alpha one another and paying is is other rich people. And so it's a dangerous game where if you don't if you aren't careful about not introducing money into your friendships, you'll find yourself hanging out with a bunch of rich dickwads. Don't get me wrong, there's
1:44:48lots of nice rich people out there, but like I don't like the idea of only hanging out with rich people. It it kind it it really knows your perspective as well. Like when you or I don't think that's even just for rich people. It's like when you only hang out with one certain kind of person, you like it's kind of like an echo chamber of beliefs.
1:45:07Totally. Well, I mean like that's often the case with entrepreneurs because very few people can share the stress of running a business. You end up hanging out with other entrepreneurs. other entrepreneurs, you know, you have certain political beliefs or they always kind of seem to have certain archetypes or whatever and then you forget that the rest of the world exists. You know, you don't get other perspectives and it's great. I think having it's like playing like soccer. If you get really into soccer, you have a shared language and a way to make friends with people, but you
1:45:35do get into this bubble in business specifically.
1:45:38Yeah. No, and I've I've definitely definitely been finding that in business. So, it's so important to to just get get different perspectives.
1:45:47Well, yeah, you if you only hang out with people who think Elon Musk is awesome, you're gonna go out in the world and talk to someone and you know, I I think Elon Musk is awesome in all sorts of ways, but you forget that the rest of the world hates him or thinks he's bad about this other thing or whatever. And it's not that you should not say you like him, but you should know all the beliefs and understand them. And you just kind of get into this warped world where without even realizing it, you speak this other language. And by speaking this other language, you alienate yourself among
1:46:16amongst other people, right? What do you think's a belief that you might have held strongly when you're first starting out your business or a belief that you were super convicted about in the past that you've now changed your mind on?
1:46:30Well, I really felt um bootstrapping was really important and I think bootstrapping is like a wonderful principle. the idea that you should not, you know, not be reliant on external money, that you should use your own cash to do things. But I think it's like idiotic sometimes. Like the example I always give is like let's say you have a cafe and you have a Tik Tok video that blows up where you are making a certain type of croissant and you're just going
1:46:58viral. There's just lines out the door. It's a phenomenon. You only have one oven and you need another oven, but it's 200 grand, right? you know that if you just get the 200 grand, you can pay yourself back in like a month for that oven, but you don't have the cash.
1:47:14Should you go to investors or get debt?
1:47:16Of course, you should, right? But there's other people that like they um take that to the extreme. They say like, you know, you should always raise money from investors and whatever. And I think it's just there's a million different ways of doing things. But I was very dogmatic and almost like religious about it. I was like, "No, you should always bootstrap." which I think is ridiculous.
1:47:37Now, this is going to be a very random question, but what what do you think has been the weirdest rich person party that you've ever attended that you can speak about here?
1:47:50Well, I mean, I've had some pretty weird experiences. Like, I went to I talked about this one on my first million, but um a couple years ago um I went to the Vanity Fair Oscars party. Do you know what that is?
1:48:04Yeah. So that's like, you know, for those that don't know, it's like the party that all the celebrities go to after the Oscars. And it's like 97% famous people and then like 3% random, you know, and most of the people that are there that are random are like they're billionaires or they're, you know, some massive entertainment mogul that maybe normal people wouldn't know, but everyone there would know. And um I was able to to finagle
1:48:32um access to it. And I realized very quickly that you don't want to be in a room that you don't deserve to be in.
1:48:42You know, it's not cool. It's like again, it goes back to like buying the Olympic gold medal on eBay, right? It's like I was able to get in cuz I had money, but I wasn't anybody in that room. Like no one gave a [ __ ] about any I I didn't own letter box at the time, right? So, it was like no involvement in film whatsoever.
1:48:59And I remember there was one guy there who um this guy Paul Shear who's a he's an awesome comedian and I he had an MTV show back in the day and I designed the website for the MTV show. So I was like, "Oh, someone I actually know." And so I walk over to him and I'm like, "Dude, like this is so random, but I designed your website in like 2008 or whatever."
1:49:20And he just goes, "What the [ __ ] are you doing here?" Right? And I was like, "Oh." Like I was like, I don't know. And I had no good answer other than like I don't know. Like I'm just, you know, I managed to get in here, right? And that was bizarre. I mean, every, you know, I was like standing at the bar next to Jeff Bezos and then Andrew Garfield is next to me and then Michelle Yo, and you know, every like The Weekend. It's like
1:49:47every famous person is there. And what's so interesting about it as well is like a you know you don't want to be in a room you don't belong in obviously but then also um all these beautiful like celebrities they look like normal people like none of them I wouldn't say any of them were like stunningly incredibly handsome or beautiful they're just they're so famous and made up in their movies or whatever that um you know we think of them as like perfect but when
1:50:16you see them in person they're just like normal people. So, that was a very weird experience for me to go to that event.
1:50:22And, uh, I don't know that I'd want to experience that again, right? Um, on the flip side, uh, you know, I've definitely gone and hung out with lots of very wealthy people. Um, I haven't had any weird experiences where like, you know, somebody brings out like a bunch, it's not like Wolf of Wall Street parties or something like that. Um, one one thing I'd say is that most of the people I know that are super rich are not doing very exciting things. Yeah.
1:50:50You know, they they're kind of generally a bit boring or isolated. They live in these huge houses. They have crazy security teams. They don't they aren't able to go out in public sometimes cuz they're so famous or they're they have, you know, they're they're in danger or whatever. Um, so that's a bizarre experience. And I would say that the people I have the most fun hanging out with are not the big names.
1:51:15They're just normal entrepreneurs. Like I have a great community in Victoria of just local entrepreneurs that I love.
1:51:21And I I would have the most fun partying with them, you know, cuz there's no there's not ego. There's so much ego as you go up the ladder. Like when you start to get meeting people where they have a name that everyone knows like often don't get me wrong there's tons of amazing people but a lot of them definitely have ego and status and you know they they become a they're like a actor like a famous actor where like when you meet them people have expectation of who they are and I find that a very weird thing.
1:51:52What do you What do you think has been the most you've spent on Night Out going to the Oscars like doing all that was like I think I was a hundred grand or something like that like to go to attend to you know getting a crazy tux and you know donating to get seats and all that stuff like you know I've definitely had those experiences and uh I just feel gross afterwards really like you know I definitely had this
1:52:20phase like four or five years years ago where I was like, "Yeah, like I'd been pretty conservative. I hadn't really spent a lot of money irresponsibly and I was like, "Let me try a few things." So, I like chartered a yacht with some friends, like did the Oscars thing and a few other things. I just felt nasty afterwards. Like lighting, you know, you go on a yacht for I think we're on a yacht for four or five days and it was like $250,000.
1:52:44And it's like, what? Like that's like a lawyer would work for an entire year to make that much money. And I just spent it on like fuel and why so that I could like be in a floating hotel in the middle of the ocean. Like why? Like why did I do that?
1:53:01I just felt gross. Uh and I get that same gross feeling from like owning multiple houses and having like the house sit empty or owning like three or four amazing cars and they like never get driven, you know? I just feel guilty. So over the last couple years, I really cut down on all that stuff.
1:53:19How do you think that's made you feel?
1:53:21Cutting down on all that makes you feel great. I think that knowing you don't need the things that to get you' have to keep working is really nice. So like for a long time I was like okay uh you know I want to buy I want to buy a plane. Uh I want to have you know five houses. I want all my favorite cities. I want to own a house.
1:53:44It's like all these things where it's just like these irrational desires that are made up that, you know, I don't even know why I would want that. Like, do I need a plane? Like, why do I need to own a plane? You know, do I do I fly that much? I fly like once a month, once every two months. Like, I don't need to own a plane, right? Uh do I really plan to spend more than like 2 weeks a year in LA? Is it important that when I stay in a house that all my stuff is there?
1:54:11Is that worth having an empty house for an entire year and spending a million, $2 million on maintenance and mortgage and all this stuff? And so, it's been very freeing for me to kind of like get to where I would deem like the maximum I I could possibly spend um to enjoy myself and realize like, oh, I don't even need that much. I don't I don't enjoy that.
1:54:34None of that brings me joy. Um and so for me, like I spend money however I want, you know? I do whatever I want, but I've realized like I really don't need more than, you know, $2 million a year, which is a lot of money, but in terms of like people get into this thing where they're like, I want to be a billionaire.
1:54:54And it's like, well, tell me why you want to be a billionaire other than the idea of like you're a billionaire, right? You're you've hit the three commas club or whatever. Um, and most people think it's cuz they're like, well, I want to be able to do anything.
1:55:07And it's like, well, really, like, it's pretty hard to spend more than like 3 million bucks, 4 million bucks a year, unless you do really, really dumb, wasteful things like buy a Formula 1 team that you just cuz you wanted to or whatever. Um, so, so from my perspective, I think like most people that want to get really rich are like overshooting. It's like, no, you could make like 25 million, 30 million and like you're killing it. Like you're living the best life ever. Um, but yeah,
1:55:36I find all that stuff just makes me feel icky.
1:55:40Which purchases do you think have been worth it or like which do you think are the few purchases that have actually made good impact on your life?
1:55:48Well, I think um anything um honestly it's so funny like the best thing ever for me is having um having a cleaner.
1:56:00Yeah. not having to clean my own house because I hate that ADHD. It's like impossible. I hate it. And that's saved me mostly from fighting with my partner because I feel like if we had to do it together, I'd be like a really bad uh I'd be a bad partner to do that with. So having a cleaner has been great. Having a um a comfortable car, but like I own a Tesla, like it's not a crazy car. That's great. That's like where I've maxed out.
1:56:25I'm like this is the best car I could ever get basically. Um, and I've had lots of super super cars and dumb stuff, too. And that's that's where I've landed. Um, having a house on the water I really like. I remember a friend told me that um there's a study where they showed that no matter where you live, you get used to it, the house, but you never get used to a view. And I have a beautiful view. So, I really appreciate every single day I sit on my back steps, rain or shine, and I do gratitudes with my
1:56:56Love that. Um, and then the freedom to be able to cancel a trip. Like, so for example, like let's say I'm on a 10day trip. I could wake up on day eight and just be like, I want to go home and just having the money to just like make changes or lose money on a hotel or whatever. I love that freedom. Um otherwise I don't know that there's Oh, and I will say like um flying private
1:57:25which you can like charter or do fractional or whatever is very very nice. But mostly only cuz I live in Victoria. Like the connections add a lot of time. But I think if I lived in a major city, I don't even know if I care that much about that.
1:57:40Yeah. What do you What do you find the benefits are of flying private?
1:57:42You just roll up and you go. So it's just a time thing, right? like um when you fly private, you drive right up to the aircraft, you get out of your car, you load up, and you go, and it's just you're just immediately there. I don't mind sitting on a plane. That's no big deal. Like a commercial airline, I don't know. I like talking to people. I like doing that. It's the waiting in the airport, the connections, the drive, you know, all the time that you waste going through security and stuff that So, it's the difference between like if I went to
1:58:10Palm Springs, I could leave at 9:00 in the morning and arrive at like 4:00 in the afternoon, 5:00 in the afternoon versus I leave 9:00 flying private and I'm there at like 11:30, you know? So, it's like it makes a big difference.
1:58:25Yeah. Definitely more comfortable, too.
1:58:27Like better for doing some work, for sure. But it doesn't really matter honestly. That part doesn't really matter.
1:58:32Oh yeah, just the time.
1:58:35So the last question that I I like to ask to all the guests that come on this podcast is what do you want to be remembered for after you die?
1:58:46I think the only thing I'm like a total nihilist. Like I truly believe my life is totally meaningless and pointless.
1:58:52Um the only thing that I care about is that I hope my kids think I was a good dad. Like I and that's such a cheesy answer, but like I think that's the only thing honestly that I care about otherwise I don't care because I think like a lot of that stuff where people get caught up on legacy where it's like oh I'm going to be like this great philanthropist or I'm going to like found a university or whatever like oh that's fine that's good and I plan to do some philanthropy and do all that stuff but I think they get very
1:59:20caught up in what will people think about me after I die and like to to me I'm like well you'll dead. Who cares, right? Like all I care about is like will my kids think I was an [ __ ] basically, which so far so good. But, you know, got to keep working on that.
1:59:38Totally. Totally. Well, Andrew, it was amazing to have you on the podcast.
1:59:43Yeah, that was fun, man.
1:59:44I really appreciate it, man.
1:59:45All right. And I have his book somewhere. So, Andrew, he wrote one of my favorite books. I've read it like read it like three times now, I think. I think a fourth time to prepare for this podcast, but I would highly recommend it. It's it's him talking about his entire story, how he went from went from zero to the place that the place that he's in today. I find it extremely inspiring and I think the main thing
2:00:12that I got from reading his book was I I really just saw myself in him. I I was like, "Wow, this guy like came from such a similar place to me. He's also from Victoria, and if he can do it, then why can't I?" So, it it was so helpful for just making me believe myself a lot more and I'd highly recommend anyone check it out.
2:00:32Thanks. Glad you liked it.
2:00:34Yeah, man. Loved it. Well, I appreciate you coming on. Of course, it was great. All right.
