How I Made My First $1M - The Andrew Wilkinson Story

Episode 604: Sam Parr ( https://twitter.com/theSamParr ) and Shaan Puri ( https://twitter.com/ShaanVP ) talk to Andrew Wilkinson ( https://x.com/awilkinson ) about how he went from a $6.50/hr barista to millionaire in just 4 years. — Show Notes: (1:00) From barista to billionaire (1:40) Andrew’s 1st level up: From day job to self employed (3:26) Shaan 1st money made as an entrepreneur (4:40) Sam’s 1st money as an entrepreneur (7:15) Andrew’s 2nd level up: From self employed to boss (8:40) From selling your time to selling other people's time (9:30) Book: The E-Myth (Thinking of your business as a machine) (10:10) Andrew makes his first million dollars profit (12:00) Robert Kiyosaki’s cashflow quadrant (13:20) Andrew’s 3rd level up: Incubating Businesses - The decathlon of failed businesses (17:00) Andrew sells one of his businesses and creates a nest egg (18:45) Andrew discovers Warren Buffet’s teachings and starts learning to invest. (19:48) Andrew's 20% rule (20:33) Sam's pauper tendencies (22:58) Andrew starts angel investing (24:00) Andrew starts hiring CEOs and removes himself from his businesses (28:30) Poker v Roulette in investing (31:20) Andrew’s 4th level up: Taking his company public and reaching the end goal. However money didn’t buy happiness. (33:46) What’s the actual amount that will make you happy? (34:37) Business is a good way to build relationships (35:35) Figuring out your annual burn rate (36:48) The goals every entrepreneur should have. Launchpad. Enough. Life’s Work (38:23) $10M = financial freedom (41:28) It doesn’t take a special skill set to get to financial independence (46:41) Shaan’s learns about the deferred life plan — Links: • Never Enough - https://www.neverenough.com/ (⬅️ Andrew’s book!) • The E-Myth - https://shorturl.at/h7Q1J • Rich Dad Poor Dad - https://shorturl.at/S28Dd • How To Get Rich - https://shorturl.at/pGTSm — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ — Check Out Shaan's Stuff: Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Andrew Wilkinson?

  I was making a small amount of money for something I hated. And then I started making a large amount of money for something I would have done anyway.

• 0:07Shaan Puri?

  For free.

• 0:07Andrew Wilkinson?

  Like it was fun.

• 0:17Shaan Puri?

  All right. What's up? We got our friend of the house, Andrew Wilkinson here. Andrew famously is the co-founder of Tiny. He started off as a barista, ended up creating a design agency that was super, super successful. Designed Slack and a bunch of other popular Silicon Valley products that you may have, may have used. Started buying businesses, read about Warren Buffett, read about Charlie Munger, started buying businesses. Now owns like, I don't know, a portfolio of 30 plus companies, I think. And recently took the company public and then stepped down to CEO. And Andrew is here on his, I don't know, vacation tour after stepping down to CEO. Andrew, good to see you, man.

• 0:50Sam Parr?

  Your skin looks great. The glow looks good. You seem happy.

• 0:53Shaan Puri?

  You got that non-operator glow.

• 0:56Sam Parr?

  Enough about talking about how much of a baby you are.

• 0:59Shaan Puri?

  All right. So Andrew, I sent you a voice note. You started off as a barista at a coffee shop and you've done very well in business. And I said, I want to know, what were the different jumps? Like income jumps that actually made a difference? And you said there was four levels.

• 1:13Andrew Wilkinson?

  Yeah, totally. Well, I think the best money that I ever made was jumping from being a barista to making like 60 bucks an hour.

• 1:22Shaan Puri?

  Well, so you go from barista, you start designing websites. So you go from 650 an hour to $60 an hour. And it sounds like that might've been somewhat happenstance. Did you, was that intentional to make that shift? Or just kind of you got an opportunity, a lucky bounce came your way? What made that shift happen?

• 1:36Andrew Wilkinson?

  So I was working, making coffees every day for all the people that come in. And there's these two guys that would come in every single day. They'd roll in looking like they just got out of bed at 10:00 in the morning. They're probably like five years older than me. So like 24, 25. And they would just come in and they would sit on their laptops all day, just drinking espresso after espresso. And one day I asked them, what do you guys do? Like, don't you have jobs? And they go, oh, we're web designers. We just walk into random businesses. We ask. Them if they have a website and then we say we'll make one for 500 bucks. And so that day I was like, well, forget this. Like, I don't want to make the espresso.

• 2:19Andrew Wilkinson?

  I want to be drinking the espresso. I want to be these guys. And so I went and I bought a book on web design and a couple of days later I walked into a place and sold the guy a website and within a couple of weeks I'd quit my job.

• 2:32Sam Parr?

  Wait, did you know anything about design?

• 2:35Andrew Wilkinson?

  Yeah, I did actually because when I was a teenager, I had a tech news website and I knew how to use like Dreamweaver, like really basic web design and stuff. So it like wasn't rocket science to me. Like I knew these guys were smart, but they weren't, you know, they didn't have any crazy qualifications. It was nothing I couldn't learn. And so I just kind of dove in and got lucky.

• 2:55Shaan Puri?

  Do you remember who you approached, that first one?

• 2:58Andrew Wilkinson?

  Yeah, it was a pulled pork barbecue joint. And there is this place called Pig here locally. And, and yeah, it was like, I think I got like 500 bucks and some free pulled pork sandwiches. You know, I basically got unlimited sandwiches for a while.

• 3:13Sam Parr?

  That's pretty awesome.

• 3:14Andrew Wilkinson?

  I was making a small amount of money for something I hated. And then I started making a large amount of money for something I would have done anyway.

• 3:21Shaan Puri?

  For free, yeah.

• 3:21Andrew Wilkinson?

  Like it was fun. It was fun designing websites and coding websites.

• 3:25Shaan Puri?

  The first money I really ever made outside of like a college job when I was in school was I actually won a business plan pitch competition and we won $25,000 of cash. And they made some MBA, some grad, a business school student work for us for 5K. It's a, we won $30,000 of total comp and me and my two co-founders lived for one year together on $25,000. But it was awesome. Like we didn't really know how much money a business takes. We didn't know, we didn't even know how much money it takes to live because we'd just been in college the whole time. So to us that was like, oh, that'll last us a long time. And we lived off of it for one year, but it was the best money at that time. It was, it was a big jump because we didn't have to get a job. So it was freedom.

• 4:07Shaan Puri?

  It's like, oh, we don't even have to think about money or a job because we got the lump sum cash upfront. And, and we got to go do the, go, go try the thing we wanted to try, you know, together as friends. So that was probably the, that was the first level. And like Andrew's saying, the early dollars create a lot more freedom than the later dollars. I think is the way that you're explaining it. And those early, early dollars and early freedom matter a lot more than the later dollars because you only get so much incremental freedom. In fact, you might actually get less freedom if you start buying a bunch of shit that now you are a slave to.

• 4:37Sam Parr?

  My first level was almost the same as yours, Sean. It was $24,000. I think I was 23 or maybe 24. I had a small website that I sold, but I still had to work there. It was basically an aqua hire. But after taxes and everything was said and done, I think I had $24,000. At the time, I was spending $2,000 a month in living expenses and I said, I have a year. I have a year of expenses saved up and I felt like, I was like, let's go to Australia. It's like, let's live, like, let's go take a trip, let's go to Thailand. Like, having $24,000, I felt incredibly wealthy.

• 5:08Shaan Puri?

  By the way, that's a powerful thing to do is change the denomination into time instead of money. So, you know, if you have $24,000, $36,000, or $90,000, it's kind of like Chuck E. Cheese money. It's tokens that you don't really understand what this does for you. And what most people do is they, they just sort of keep working blindly. They'll put it in the bank and then they don't really know how to use it, what to do with it. A more important question is, how do I get myself a year of freedom? Or 18 months of freedom where I could either just go enjoy myself purely or go take a shot at creating a new life for myself, a new chapter, a new, a new path for myself. And early on, it doesn't take much to get a year. Like, both of us basically did it on $25,000, which I think is surprising, it's surprising even for me to hear it right now because my current life burn rate's a lot higher, right?

• 5:52Shaan Puri?

  But, you know, we slept on air mattresses. It's like, well, why do we need, you know? And then we got to, we got to mattress and headboard money eventually, but at first, it doesn't really matter. But a year of freedom or 18 months of freedom, 24 months of freedom is a good way to denominate things when you don't have a huge sum of money.

• 6:06Sam Parr?

  I use this app. I didn't use Mint. I use this one app where every time I spent anything, I typed it in, how much money I'd spent for that. So if I went and got coffee, it was $2.50. I wrote $2.50 in there and then I had this spreadsheet where I took the average of the trailing six months. And I said, that is my monthly burn and then here's how much money I've saved. Get to 12 months. And so I used an app. All right, guys, really quick. So back when I was running The Hustle, we had this premium newsletter called Trends. The way it worked was we hired a ton of analysts and we created this sort of playbook for researching different companies and ideas and emerging trends to help you make money and build businesses. Well, HubSpot did something kind of cool. So they took this playbook that we developed and we gave to our analysts and they turned it into an actionable guide and a resource.

• 6:47Sam Parr?

  That anyone can download and it breaks down all the different methods that we use for spotting upcoming trends for spotting different companies that are gonna explode and grow really quickly. So if you want to stay ahead of the game and you want to find cool business ideas or different niches that most people have no idea they exist, this is the ultimate guide. So if you want to check it out, you can see the link down below in the description. Now, back to the show.

• 7:10Shaan Puri?

  All right, so you've you've made it to level two. Now, the next level, you said, I went from self-employed to boss. So what does that mean?

• 7:16Andrew Wilkinson?

  What I over time discovered was that there was all these online job boards. And there was companies in San Francisco posting, looking for freelance designers and developers and stuff. So I was doing these like little $500 local websites. And I found these Silicon Valley startups posting. And this was like what like what you would call today like product designer, interface design. And so I got this project designing an interface for an ad manager for some startup. And I did a really good job. The guy really liked it. And it was like $2,000 for basically no work. This is the project I mentioned before. So it was like maybe five days of work for two grand, which ended up being 2,600 bucks Canadian. So it's very sweet.

• 8:01Andrew Wilkinson?

  And the guy goes, hey, this is pretty good. Can you do coding? Like, can you do some JavaScript work? And I just say, yes. And I don't know anything about JavaScript. I'm like, whatever, I can figure it out. So I frantically try and learn JavaScript and I can't. And so I go to my friend who's literally just my girlfriend's best friend's boyfriend, who's in computer science. And I say, hey, how much would you charge me to do this JavaScript work? And he goes, I'll do it for 500 bucks. And so I think I'm gonna get negotiated down by this client. And so I go to the client and I say, it'll be 1,000 bucks. And they say, okay, sounds good.

• 8:40Andrew Wilkinson?

  And so in that moment, I was like, oh, my God, I just made $500 and I did absolutely no work. So that's such crazy transition of going from being a self-employed person selling your time to being someone who can sell other people's time, which to me is like the big leverage point.

• 8:58Shaan Puri?

  That's great. You so you have that realization. Did you start devouring any books? Or how did you learn how to do that better than, you know, than than being an absolute rookie at it?

• 9:08Andrew Wilkinson?

  It was mostly trial and error in the beginning and it was really, it was really stressful, honestly, because I think when you start delegating to other people, they always do a worse job than you do. And so you are kind of panicking and you, there's no, there's no like process or system or anything. And around that time, I read this book called The E-Myth. It's kind of cheesy. It's by Michael Gerber, but I recommend it to everyone. And he really talks about this idea of trying to think of your business as a machine, right? And I think for me, that was the, that was a big breakthrough, that mental model of, my business is a machine and I'm the engineer and all the different people are widgets within the machine. And if one doesn't work or something is squeaky, you can swap out the people.

• 9:52Andrew Wilkinson?

  But at the end of the day, you have a process, you have a strategy and you have people on the bus. And if you have the right people on the right bus, the right strategy and the right vision, things will go well. And that was when things really took off. That was when I started hiring, you know, I had like a dozen people. I was making, you know, over a million dollars a year personally. You know, I got a BMW. I started dressing nice. And really that was like the, the kind of sloppy, like the first phase was like, you know, okay, I can do all the stuff I wanted to do in college. I can buy beer. I can go for a nice dinner and stuff.

• 10:26Sam Parr?

  Wait, how, how old were you when you made your first, is that million profit?

• 10:30Andrew Wilkinson?

  Yeah, I think I was 20, 22 or 23.

• 10:35Sam Parr?

  That's huge. That's huge.

• 10:36Andrew Wilkinson?

  Oh yeah, it was amazing.

• 10:37Shaan Puri?

  You didn't go to college, right? Or you dropped out?

• 10:39Andrew Wilkinson?

  I dropped out of college. I went to journalism school for like two or three months.

• 10:44Sam Parr?

  So you did a million in profit two years into being an agency?

• 10:48Andrew Wilkinson?

  I started when I was 19 years old and so probably four years in, something like that, three or four years in.

• 10:54Sam Parr?

  That's massive.

• 10:54Andrew Wilkinson?

  It was, it was crazy. I mean, it felt like, it felt like an absolute fortune and frankly, it was. And at that point, like that was when I was like, oh, like I'll just buy whatever I want. Like I would walk into Best Buy and just buy like a crazy TV. I would buy, you know, the best speakers money could buy. I would buy video games, like whatever an idiot 23 year old wants to spend money on, I would spend money on that. And ultimately.

• 11:18Shaan Puri?

  Your bill is like $800. You're like, okay, well now what? My tastes don't even match my, my income right now.

• 11:25Andrew Wilkinson?

  Yeah, it was very, it was very kind of empty and hedonistic.

• 11:29Shaan Puri?

  Did you ever read Rich Dad Poor Dad, Andrew?

• 11:31Andrew Wilkinson?

  Yeah.

• 11:32Shaan Puri?

  He has that, Sam, have you read that book? He's got that quadrant thing. Do you know about that?

• 11:37Sam Parr?

  Yeah, people hate on that guy. I'm not sure why, but what about it?

• 11:41Shaan Puri?

  Well, I mean, any, any business guy who becomes popular and starts selling anything, I think he sells a lot of shit. He sells like gold, he sells like real estate courses, he sells a lot of stuff. But Andrew, you basically just described his thing. I remember reading this book and I had this mental model then of what you're supposed to do in your career. So basically he's like, he has this four quadrant grid and it's basically E is the first one. You're an employee, you have a job. And he's like, for most people, this is what your parents tell you. Go to, go to a good school so you can get a good job. And they kind of make it sound like getting a good job is the endpoint. That is the like, that's the end of the rainbow. That's the pot of gold. And what he's, what he points out, he's like, you know, basically you start as a E, then you go to the bottom quadrant S where self-employed. So you go from employed to self-employed. That's what you described, barista to solo freelance web designer.

• 12:27Shaan Puri?

  Then you go to B, business owner. That's when you owned your agency. And the last one is I, he's like, the goal, the goal for everybody is to get to I where you're an investor. Your money works for your money and you do whatever the hell you want. And so eventually with Tiny, you became, ah, you became an investor. But like this path going from E S B I is one that for me, I didn't even really, I didn't understand how the board game was laid out. I didn't know where you're supposed to go, right? It's like playing a video game, but not understanding. You need to save the princess from the castle. It's like, oh, once I know that, now I can start to move in that direction. But until I even knew that, I didn't really even understand what the hell I was supposed to be doing. This one diagram was very useful for me.

• 13:05Sam Parr?

  And that was in level two for you was between what a million dollars a year and what was your upper limit?

• 13:12Andrew Wilkinson?

  Yeah, I mean, I was paying myself 500 to a million a year and I was profiting more than that. And I started incubating businesses. And so I had that classic thing where I had overconfidence. The way I would put it is that my first business was a very easy business. So I did the equivalent of walking into the gym and I got lucky. I picked up really light weights and it built my confidence. And then for the next five, 10 years, I would walk into the gym and try and deadlift 300 pounds, but I didn't know that was hard, right? And so I I started an e-commerce business. I started a restaurant. I started multiple software businesses that I bootstrapped and lost in one case to over $10 million.

• 13:57Andrew Wilkinson?

  But it was really fun because I would just be in the shower and I would think, oh, man, that's a great business idea. I'll start that right now, today. I had no filter whatsoever and it was really exciting, frankly, like I was just, I was constantly starting new stuff.

• 14:13Sam Parr?

  Starting a restaurant is an awesome way to lose money, though.

• 14:16Andrew Wilkinson?

  Oh, yeah. And I lost, I think I lost a million bucks doing that.

• 14:19Sam Parr?

  You still have it?

• 14:20Andrew Wilkinson?

  Cat furniture, restaurant, skin cream, SaaS company. You tried, you did the full decathlon of like business ideas. We had a blog. We had a viral blog. We tried to write a book for it. We had a concierge service.

• 14:36Sam Parr?

  What was the viral blog?

• 14:38Andrew Wilkinson?

  We had clients from hell. It was like really big on Tumblr for a while. Do you know it?

• 14:42Sam Parr?

  No, I don't know.

• 14:45Andrew Wilkinson?

  We basically, we would, we would have all these like, we would go to conferences and meet other designers and stuff. And everyone would bitch about their crazy clients and share screenshots of like insane emails they had received and stuff where it's just like the guy asking for them to make the logo bigger over and over again. And so we started sharing those and it just went crazy viral. And so we ended up making a book.

• 15:07Sam Parr?

  Dude, we need to bring back Tumblr. Tumblr was great. I love the Tumblr. I love the Tumblr days. I still go back and I'll read old people's Tumblrs. It's awesome. I love it. I mean, Twitter kind of is that now, but I felt Tumblr had a better environment and it was more friendly and better content.

• 15:23Andrew Wilkinson?

  I made so many friends from Tumblr and I still meet people like at conferences that know me from Tumblr back in the day.

• 15:29Sam Parr?

  What age were you when level three ended or level two ended?

• 15:33Andrew Wilkinson?

  I ended that probably like 27. I think that was when I sold my first business.

• 15:39Sam Parr?

  What did you sell for and what was it?

• 15:41Andrew Wilkinson?

  So I sold it for seven million bucks and it was the one business I started in level two. So I started all these different companies. I, so I had my original web design company, MetaLab. It was profitable. I would live off part of that profit and then the rest of it went to starting all those other businesses I talked about. The one business that worked was I met Toby from Shopify and Harley as well in 2010 at a conference. And at the time Shopify was pretty small and they said, hey, we really love your design work. Would you make some templates, some themes for Shopify? And I was like, oh, you know, I

• 16:24Andrew Wilkinson?

  guess we could do these guys a favor. They seem nice. I tried to get them to pay me and they actually said, no, no, no, this is going to be like a store, like the iPhone app store. And I was like, ugh, like, okay, I guess so. And so we did it. I literally thought we were doing them a favor and we put up a bunch of themes in their store and we started making like 10, $20,000.

• 16:44Sam Parr?

  A what, a month?

• 16:45Andrew Wilkinson?

  A month, like basically immediately.

• 16:47Sam Parr?

  And what year, what year was that?

• 16:48Andrew Wilkinson?

  2011, probably.

• 16:50Sam Parr?

  2011?

• 16:51Andrew Wilkinson?

  2010, 2011.

• 16:52Sam Parr?

  All right, 2011, you're doing 20 or 30 grand a month. Is this called Pixel Union?

• 16:56Andrew Wilkinson?

  It's called Pixel Union. And so I had the, I had the original design agency. I had Pixel Union and that started making quite a bit of money. And then I had all these chaotic other businesses. And basically what happened was I decided that I wanted to have like a nest egg. I wanted to have enough money in the bank that I didn't have to worry about money anymore. And, because what I had, what I had had is cash flow. I had a ton of cash flow, but I never kept much money in the bank. I'd spend whatever I needed personally. Everything else would get invested, even though I didn't really understand investing, in these businesses I was incubating. And so I ended up getting an offer to sell that business for seven million bucks. And it was three million upfront,

• 17:41Andrew Wilkinson?

  one and a half earn out, and then the rest in stock in the new business. And I remember I went to the ATM on the day it closed and I checked my balance. I was in like a Strip mall and I saw three million, it was like three million, one hundred thousand or something like that on the chit. And I was like, I'm done, like I'm rich, I'm good forever. And that was a big mindset shift. Suddenly I had money, more money than I could use to incubate businesses. I'd also incubated a lot of businesses and I realized that starting companies is really hard. If you think about my failure rate, I probably started 10 different projects or companies and one of those worked really well.

• 18:22Andrew Wilkinson?

  And so there's a lot of pain and I had to lay a lot of people off and go through a lot of hard times to do that. And frankly, I felt pretty burnt out and around that time I was like, well, I guess I've got to learn how to invest. But to me, investing was something that like guys in suits did, like it was super boring. I had no interest in real estate or stocks. But I'd always heard about Warren Buffett and whenever I read about Warren Buffett, that changed everything for me. What I, what I ended up doing is I had all the, the incubated businesses. I actually shut almost all of them down. And I'd sold the, that business for three million. I had another one and a half coming. And I also got dividends out of that business because I still own 20% of it.

• 19:04Andrew Wilkinson?

  And then Metalab by this point was making three or four million dollars of profit a year. And so I went from burning a lot of cash and living a nice lifestyle to suddenly having a pile of cash and a lot of unencumbered cash flow coming in that just kept piling up. So by that point, if you think about, if you're making four or five million dollars a year. At this point, I buy a really nice house, not as crazy. I could have gone crazy, but I, I bought like a responsible, nice house. I bought, uh, you know, a nice, a nicer car, bought myself like a Porsche. And I had a Tesla, which at the time was like super crazy. And I started getting into investing at this point. What was this 20% rule you had?

• 19:49Andrew Wilkinson?

  So basically I was like, I, I will spend up to 20% of my cash flow personally. And the other 80% has to go back to investing. And so I knew that, you know, on 20% of Five million bucks, you know, I could live a pretty damn good life spending a million dollars a year. I wouldn't go out of my way to spend that much.

• 20:08Sam Parr?

  Post-tax or pre?

• 20:09Andrew Wilkinson?

  Pre-tax. So I would, I would basically live it up as much as possible, but then I also knew I'd always be compounding the rest. And that model actually worked really well for me because I didn't have this mindset that so many entrepreneurs have where they're like, shit, I gotta live like a popper and then I gotta become a prince. I gotta sell my company for some huge amount of money. I was just able to live on cash flows the entire time. Sam, can we talk about some of your popper?

• 20:35Sam Parr?

  Yeah, what the fuck is a popper?

• 20:36Andrew Wilkinson?

  Popper tendencies you had? As Sam chugged a Dr. Pepper while you were talking.

• 20:42Andrew Wilkinson?

  So Sam, what were you doing when you were building the hustle? How did you live it? Were there any cheapskate?

• 20:46Sam Parr?

  Oh, yeah. So my wife worked at Facebook at the time. So dinner was like, I gave her Tupperware containers and she would bring home prosciutto and cheese because they always had like charcuterie boards. So I was.

• 20:57Andrew Wilkinson?

  Dinner was sponsored by Meta every night?

• 21:00Sam Parr?

  Yeah. So we, I was on a prosciutto diet because I didn't get old fast. The second thing, I'm ashamed to say I did this, but listen to this. So do you guys remember when Uber Eats and DoorDash and what were the other ones? Caviar? So these meal delivery services all came out at the same time and you would get $20 for free for your first order. So I built a iPhone emulator on our computer where we created this ring where we were constantly referring each other to these like new. So I basically had like $5,000 of free caviar. So I would basically, people would be like, is your startup funded? I was like, no, but we are fueled. We're fueled by VC, but we're not funded. And so I did

• 21:42Sam Parr?

  that for a long time. I also would sneak on the bus and not pay and I would get caught all the time. But the thing is, is if they ask for your ID, you just say you don't have an ID. And so that was, that's not, it's not illegal not to have an ID. So I got away with like two grand worth of bus tickets.

• 22:00Shaan Puri?

  Yeah, there's nobody checks on San Francisco.

• 22:01Sam Parr?

  They did. I used to get in trouble all the time, but they would say, uh, you know, do you have your ID? I'm like, I don't have an ID. Uh, so I'll tell you, you know, but yeah, so hopefully there's a statute of limitations on these things. I definitely broke the law a little bit. I was also on a, I was on a Whole Foods scholarship as well. Uh, let's just say that the, uh, the, the hot bar was right next to the exit.

• 22:21Shaan Puri?

  So, so Andrew, you, when you were spending, uh, 20% pre-tax, that's like you're spending 40% of your post-tax money. That's a lot to be spending during that time. And then you shifted it. You, you, once you started investing, you made a change. You were like, no, no more 20% rule. You changed it to some other rule. Right? Right? What, what did you shift to?

• 22:38Andrew Wilkinson?

  Yeah, I just kept dropping that percent over time. As, as the numbers got bigger, I just kept dropping it and dropping it and dropping it. And

• 22:46Sam Parr?

  But not because you're spending less.

• 22:48Andrew Wilkinson?

  No, not necessarily. I, in some cases I was spending more. The numbers just got bigger. So around this time, so, so I'll talk about some of the things I started doing. So I started angel investing. So, you know, I'd meet a friend or some interesting entrepreneur and I'd invest 25 grand in their company. And if I look back, like I probably should have bought stocks in real estate. Like I didn't understand the lack of liquidity and that, and just how like high risk it is and crazy. So I have a whole bunch of investments from that era. I have no idea what's going to happen with them. But mostly, a lot of that time was actually spent having this breakthrough moment of realizing that I don't need to be the CEO, that I don't need to run my own companies. And so at that time,

• 23:33Andrew Wilkinson?

  every single company, I was the CEO of it. So it was me and Chris. I'm the CF, CEO, he's the CFO, and we're just jumping around like chickens with our heads cut off between all the different businesses. And when I read about Warren Buffett, I was just like, oh my God, this guy has abstracted business to the craziest degree, to the point where he doesn't actually do anything except for read and buy like one business a year. And the idea that you could just hire a CEO to run your company was kind of crazy. Like I think a lot of people have this feeling around, you know, why would someone come and work for me?

• 24:10Sam Parr?

  I felt like that all the time. I'm like,

• 24:12Andrew Wilkinson?

  Yeah, you're like,

• 24:13Sam Parr?

  what are you doing?

• 24:14Andrew Wilkinson?

  Yeah, it's like, why? Like, don't you know the math? Like, this doesn't make any sense. But then, over time, you realize, like, people want stability, and they want surety, and they want to have health benefits, and all this stuff you don't get. And so I realized, like, there's this whole other class of people where they want to run a company for somebody else. They want to be a CEO. They want to be able to make, you know, millions of dollars, but they don't necessarily need to make like a billion dollars. And that was crazy for me when I started hiring CEOs, because before I knew it, all the businesses started like doubling. And the reason they doubled was because I was only giving 20% of my time to all the companies. And frankly, I didn't know what I was doing. And I just started hiring better and better people to run my companies.

• 24:58Andrew Wilkinson?

  And there's this crazy inflection point where we started spinning out the companies, hiring CEOs, and then buying new businesses, and just putting CEOs in to run those businesses. And when we started doing that, the numbers scaled really, really quickly.

• 25:13Sam Parr?

  So you did a lot of angel investing in this period? And we'll talk about the rest of the stage. But have you seen a good return from those investments? Because that was a good era.

• 25:23Andrew Wilkinson?

  Yeah, I mean, I don't know, to be honest. The problem with angel investing is like, I just still, I've slowed down, but I mostly just do it on gut. And so I think I have like $25 or $30 million of venture. And it's just been this like death by a thousand paper cuts thing. So I think if you take that cohort, I had one, my friend Stuart, who we used to share an office with, I put 75 grand into his business, and then he sold it to Workday. And I 10x my money there. And I think that, between that and a few other investments, I think I've definitely got my money back from that cohort, maybe made a good, you know, a reasonable return. But the problem is, I've just kept going, and I don't really track it. Like, it's all in one big Excel spreadsheet somewhere, and I don't mark it.

• 26:09Sam Parr?

  You think you made $25 million of angel investments?

• 26:11Andrew Wilkinson?

  Yes.

• 26:11Sam Parr?

  That's a ton.

• 26:12Andrew Wilkinson?

  Maybe even 30.

• 26:15Andrew Wilkinson?

  That's an insane amount of angel investing.

• 26:17Shaan Puri?

  What?

• 26:18Sam Parr?

  That's fiscally irresponsible, my friend.

• 26:21Andrew Wilkinson?

  I know, I know. That's the problem with angel investing.

• 26:23Shaan Puri?

  10x is not going to return all that money. How do you, why do you think you've returned $30 billion? I don't think that's-

• 26:27Andrew Wilkinson?

  No, no, no. I'm not saying I've returned 30 million. I've literally put $30 million into venture.

• 26:32Shaan Puri?

  I know, but you say you may be broken even, right? You think, you think you've-

• 26:35Andrew Wilkinson?

  No, no, no. Oh, no, no, no. To be clear, I've not gotten 30 million back.

• 26:38Sam Parr?

  I think you are so full of shit. You're telling me you don't have a spreadsheet that just like, if I have 30-

• 26:43Andrew Wilkinson?

  No.

• 26:43Sam Parr?

  My friend.

• 26:44Andrew Wilkinson?

  No.

• 26:44Sam Parr?

  It doesn't matter if you're a billionaire, if you are many billions of theirs, you track $30 million. That's not, that's not couch money regardless of who you are.

• 26:53Andrew Wilkinson?

  No, so I actually have, I've, when I say I've returned, I mean from that cohort. So like, maybe I invested like $2 or $3 million over that period. And I'm saying I might've got that money back, but the rest, so much of it was done over the last 10 years in, in bursts that I don't even know, I don't know where we're at in terms of payback. I honestly, I don't track it because it's such a pain in the ass to get mark to markets and I don't trust them. And so I'm literally just going, either they sell or we get liquidity or we don't. And so for me, it's all marked at book value until it gets realized.

• 27:26Shaan Puri?

  Crazy, but that, that is actually more par for the course, I think, for, for the way angel investing works. Cause I think if you're listening to this, you don't angel invest, it sounds insane. And there is a bit of it that's insane as in that's a very big number to have, to have put into it. But these are like 10 year odysseys. People stop sending updates. Even when they raise at up rounds, you don't fully believe, you don't fully know if that's, you can't really take that and count that until it's fully realized. And so it is very easy to lose track of the portfolio and where it's at because you don't really know where it's at. That's kind of the reality of the situation.

• 28:03Sam Parr?

  A company will raise money at some huge valuation and then a year later it's gone out of business. And so I've, I've invested a lot of money in angel as well. And like I track which company and which year I invested in, but half of them don't send updates. The other half, they have markups and I'll put it in there, but I don't count it as real net worth. And then I'll be, and then another portion, when they sell, you don't know they're going to sell until when the deal's done. A large part of the time. I count it as my net worth, by the way, as the principal I invested, but half.

• 28:30Andrew Wilkinson?

  Totally. A hundred percent. That's how I think about it, too. I think of it as roulette. And I think like this period that we're talking about was about me learning how to play poker. Right? Poker has way better odds than roulette. If you're good at poker, you can actually win. You've got, you know, 60% odds. When you play roulette, you've got 50% odds. It's a terrible game and angel investing is frankly, a roulette table. You're just having fun and it's fun to be able to say, you know, oh, I gave this entrepreneur who ended up building this great company, 25 grand along the way. But I've realized it's a lot more kind of soulless than playing poker. It's more fun. You feel smart playing poker. You feel dumb playing roulette.

• 29:09Shaan Puri?

  Also, the narratives we tell ourselves is just like roulette where you're like, I knew it. I thought 11 was coming because I saw it 11 flash up over there. And then that's why, and if you, if you talk to a lot of angel investors, it's like, you know, you bet on two guys when they had a different idea and then it turned, you know, you, you bet on Stuart Butterfield when he was building a game and then it turns into Slack. And, you know, did you know, you might've known that Stuart was good, but did, did you really know? You know, and I think a lot of people attribute skill to where there was luck or, and not, not the other way around.

• 29:37Sam Parr?

  And it sucks that you're making your money, you're making your money right at the beginning of the greatest bull market in American history. And so, starting in 2010 or so, you're, you know what their average returns are for the last 15 years for S and P 500? Before inflation, I think it's 14%, which basically means you double your money every five years. So what would that be? One million become two million, become four million. So you would have four X your money just doing that boring shit, but that's way more boring.

• 30:03Andrew Wilkinson?

  Yeah, that's the thing. I think my, one of my regrets looking back is I wish that I had bought apartment buildings or something really boring, just as a diversification thing and stocks and just been really disciplined there. And instead, you know, I was maybe, I was just shoveling, you know, a hundred thousand dollars a month out to all these different startups. And then that number went up and up and up over time as I had more free cash to deploy. And again, like I have winners in there, like I invested in SpaceX. I've invested in some great funds. There's some awesome companies in there. But to Sean's point, like unless you're reporting the LPs and making up numbers frankly, with up rounds, like you just have to wait.

• 30:45Shaan Puri?

  Yeah. All right. First of all, thank you for sharing all those levels because A, it's interesting. And B, you don't have to, and most people do not. Props to you for being transparent about it. And also, the takeaway I have is like, it takes a lot of wandering and you go through these eras, you go through these phases. It's kind of the same way you were talking about Tumblr. And it's like, yeah, I had my teen emo phase. It's like, yeah, you go and experiment over there and then you kind of learn. You have some fun, but you kind of learn that's not it. That's not the right path for me. And it sounds like you had a bunch of those and I'm glad you shared it. I want to ask you, you have a question here. Do you really need to be a billionaire? What are your thoughts on that?

• 31:21Andrew Wilkinson?

  We forgot one level. We forgot one level.

• 31:23Shaan Puri?

  What's the last level?

• 31:24Andrew Wilkinson?

  So, so last level is when I took my company public and I had tens of millions of dollars in the bank, both in my companies and personally. And what's weird is I'd reached the end, right? I think that's the goal that so many entrepreneurs think they want. And what I realized is even then with all that money in the bank, I was still anxious. I still fought with my partner. I still got irritated with day-to-day life problems. Like ultimately, like it's kind of like travel. We all think we want to go to Bali. If only I moved to Bali, then I'd be happy. The problem with moving to Bali is your brain comes with you. And it turned out my brain is just really anxious.

• 32:08Sam Parr?

  Before I had anything, I would want to pump my own chest all the time because I felt like I haven't lived up to my potential. Once, you know, I got lucky and things kind of worked out, I was like, you know, I'm going to not talk about this shit anymore because there's more to life now and this burden does feel weird. I don't even want to bring it up. So I'm just going to be kind of a little more private about this. Why, why not just act like that?

• 32:29Shaan Puri?

  Because I wish somebody had told me. It's kind of like, um, oh, money didn't make you happy. Eh, kind of figured that, meaning you made a bunch of money and it didn't fundamentally change your overall level of happiness. Or these materialistic things didn't make you happy. I think you're probably smart enough to have not been totally surprised by that. What did surprise you?

• 32:53Andrew Wilkinson?

  Well, I think what surprised me was the weight of the money, right? So, you know, we, I wrote this in the prep doc, but like this question of like, do you really need to be a billionaire or do you want to be a billionaire?

• 33:05Sam Parr?

  But you wanted to be.

• 33:06Andrew Wilkinson?

  I wanted to be. I always wanted to be because I didn't have enough money growing up. Money was a four-letter word in our house, right? My parents fought about money all the time. And so in my weird, little anxious child brain, I said, okay, I want as much money as possible. If I have a lot of money, then everyone will stop fighting. And I think what was counterintuitive is that it didn't, it didn't cause that. So it actually caused familial discord. It didn't get me friends. It isolated me from other people because I was unrelatable. What's the thing you wish somebody told you? So you wish somebody told you, hey, these things are not going to fundamentally make you happy. The anxiety you're carrying, you're going to carry it over here too. What do you wish that they told you instead? The question is like, what's the actual amount of money you want to spend each year?

• 33:50Andrew Wilkinson?

  That makes you happy and just working in reverse from there? And then figuring out, okay, what is my life's work after that? I think overshooting is a mistake that a lot of people make, myself included. And I think they think, okay, I need to be a billionaire or be worth hundreds of millions of dollars. When in reality, that is overdoing it. It's like, you know, look, you have, you have, you have a belly and you can only eat so much food. Why do you need a hundred X that amount of food? If you have a hundred X the amount of food you need, well, it's actually kind of stressful. Cause A, it's wasteful. You don't want the food to go bad and you gotta do something with the food. And so the book frankly is like, it's kind of like a letter to myself 10 years ago. To say like, hey, you don't need to go there.

• 34:33Andrew Wilkinson?

  Like just like, good things are not where you think they are.

• 34:37Sam Parr?

  If money, so you're in a weird position where your job is, you know, as an investor, your job is, you're doing a good job based on your returns. So you're, you're doing a good job based off how much money your, your, your clients or your, you yourself make. But if money wasn't part of it, would you still be investing? Did you just get into that to make money or, or is this how you'd spend your time regardless?

• 34:57Andrew Wilkinson?

  I really like relationships and I think business is a great way to build relationships. That sounds kind of cheesy, but like business is a shared language where if I meet even a like a guy who owns a plumbing company, I know I'll be able to get along with him because we speak the same language. We can, we can get into interesting conversations and through that I can make friends. And I've found that my, for me, like my zone of genius is like building relationships with people. And so if I can build relationships with people and invest in their businesses or buy, buy their businesses, that, that like, I'm really happy doing that. I love doing that.

• 35:35Shaan Puri?

  So Andrew, if you were going to go back, you said you should calculate how much you want to spend every year and then kind of work backwards from that. So let's do the math. What would you, you get to go in a time machine, you go back to 25 year old you and you get to have this conversation. What, what would you write down on the pen and paper to figure that out?

• 35:52Andrew Wilkinson?

  Well, I think what you want to figure out is you want to say, what do I want to spend every year? And then times it by 20.

• 35:57Shaan Puri?

  What do you think you would want to spend every year?

• 35:59Andrew Wilkinson?

  Back then, I think, I think a million, I mean, okay, so let me put it this way. So a million dollars, you can live an incredible life and have one house, go on incredible vacations. Like you can live an amazing life. If you want to fly private, add another million dollars. So that's $2 million. And then you want to buffer, so call it three. And that allows you, you know, you basically go and you, you get into hobbies and toys and you collect cars or do whatever you want, right? So call it 3 million bucks. So what's three times 20? So $60 million. I think $60 million, if you've got it liquid, that's, you know, you can live an incredible

• 36:41Andrew Wilkinson?

  life and spend three to four million dollars a year. And, and it's awesome. So that's kind of how I think about it.

• 36:48Shaan Puri?

  That's your target. Then you'd work backwards from that. And you also had these like three steps that you texted us. I don't know exactly what they mean, but you said launchpad enough and life's work. What do those mean?

• 36:58Andrew Wilkinson?

  Yeah, so I think these are, these really are the kind of goals that everyone should have. So Launchpad is like, how do you make 250K a year, right? And ideally passive, and if you can make 250K a year passive, then you don't need a job and you have the freedom to be generative and start the things that you want. Past that enough is like, what's the amount you, what's the, what's the number? What's that number we were just talking about that you want to spend every year? And how do you work backwards from there? So Phase One might be you start a business, let's say some online business. It makes you 250K a year passive. Great, that's your Launchpad. Then for the next five or 10 years, you try and build up to that net worth number

• 37:38Andrew Wilkinson?

  that you really want to get to, call it, you know, 20, 30, 40 million dollars, whatever that is. And then you've got complete freedom. And then this is where the hard part comes in, which is discovering your life's work. It's like, what is that thing that you're just intrinsically drawn to that creates meaning? And also, how do you take the byproduct of your machine? You've now built a money machine, right? All your investments and all your businesses. And the byproduct of that is money. And how do you make meaning out of that money? For some people, it's compounding in more businesses. For other people, it's giving it away and doing philanthropy. For others, it's doing art projects or whatever it is. And I think that's the hard part is figuring out that second mountain, they call it.

• 38:23Sam Parr?

  Sean, have you done the math? Like, have you thought about that for you?

• 38:27Andrew Wilkinson?

  Yeah.

• 38:27Sam Parr?

  What's yours?

• 38:28Shaan Puri?

  Yeah, I did, I did a long time ago. Before I sold my first business, I did this math. My assumption was that I would spend $300,000 a year. And then I tried to do the four or 5%, assuming that that's 4% or 5% of your total. I forget what it was, I remember getting to 6 million and I said, what is that math? That's, yeah, 300, that's exactly it. So 300,000 a year of spending. And I thought, 6 million, that's the target. And I drilled that into my brain. I said, financial freedom is at 6 million. 6 million means, you know, I could spend whatever I want. And I made it like part of my, like, all of my passwords when I would log in. It had the number 6 in it. And I did all these things, I just kept, at that time, I was like really focused on it. And I think actually it was like the right.

• 39:13Shaan Puri?

  It was the right way to think about it. Uh, you know, today I probably spend a little bit more than that. So it's not like it's, it's not like I was way off in my estimate. Uh, but I think round number 10 million is financial freedom for almost everybody. And 10 million is not that hard to get to. If you, if you own a business, um, you, you should be able to get to, you know, let's call it one to two million a year, profit a year and sell that thing for, you know, somewhere between five and five and 10x multiple, depending on what industry you're in. That's not a hard way to get to 10 million.

• 39:46Sam Parr?

  It's hard, but it's simple.

• 39:47Shaan Puri?

  Yeah. I guess like what I mean is like, most people will never get to true financial independence, where they're like, yes, I've made it. I don't have to worry about money ever again. Right? That's a very lucky few people, few percentage of the population. Like I'll tell you this, I did this thing the other night, which I'm not really proud of. I, uh, I went on LinkedIn and I searched my college class. Uh, so it's like, okay, let me go look at Duke 2010.

• 40:14Sam Parr?

  Dude, that's my, that's my Friday night routine. I do it every Friday night at one o'clock.

• 40:17Shaan Puri?

  I literally did this on a Friday.

• 40:18Sam Parr?

  I got it on my schedule. I got a reminder on my calendar at one o'clock AM, uh, Friday night. I gotta like.

• 40:25Shaan Puri?

  You joke? This is literally what I did. My kids went to bed, my wife went to bed and I was like, all right, dig in, baby. Let's do this. I had never done it before, but I was like, let's do this. And I knew at the time I'm doing this for kind of a F'd up reason, which is I just wanted to feel good about myself. I was like, I kind of knew, I was like, I think I've done well relative to the people in my class, but I knew maybe skill or intelligence or talent wise, or even work ethic wise, I was definitely average to maybe below average in my class. And I, so I was scrolling through it. I was looking and it was amazing, man. These people who I, I know these people, these people were smarter than me, harder working than me, more talented than me. Um, they're doing like just kind of random jobs. And I texted my college room and I was like, man, it's crazy that like this person, this one, this one girl I remember,

• 41:07Shaan Puri?

  I was like, she literally could have been president. Like she was polished. She was a phenomenal speaker, super hardworking, just knew everything about everything. And I was like, and today she was like running, uh, she was like an e-commerce manager at some e-comm brand that sells like, you know, some food product online. And nothing wrong with that. That's not like a bad thing, but I definitely feel like, you know, the potential was there for a lot more if somebody had kind of sat us down and said, look, Here's a blueprint. Here's a path that could get you to complete financial independence. Like if somebody our senior had come and said, look, how much, do you even know how much money you want and need? I'm like, none of us would have known. It's like, do the math. You sort of get there. You think, okay, maybe you get to five million or 10 million bucks. And said, do you know how do you get there? And I would have been, me as a senior would have said, I

• 41:50Shaan Puri?

  have no clue how you get there. Is that like salary and save up? Like, what am I supposed to do? And if somebody had said, no, no, no, here's what you could start a business. I guess this, you sell for this multiple, that whole thing might take you five to seven years, maybe 10 years total. And by the time you're 31, you might be there, right? Like, if somebody had sat me down, I would have really felt like thankful and been like, wow, I don't have to go do that. But I'm glad I know what I can, I'm glad I even know what that looks like, because I didn't know that. My parents didn't do that. So they didn't teach me that. That's not something they knew, right? Like, I saw this great quote, you can't ask somebody for directions to a place that they've never been. And I guess like, growing up, I was asking people for directions to a place that they had never been. And so therefore, they were just giving me all kinds of screwed up directions to places that I didn't want to go. And so,

• 42:35Shaan Puri?

  um, yeah, I guess like, there's a long winded way of saying, I think, when I looked at that class thing, I guess like, the, I went into it trying to feel good about myself. But actually, I ended up feeling bad. I was like, man, I feel like there was a lot of potential on the table. And most people took basically safety and prestige. Like, they had a good job at a great company. And I'd rather have no job at my company, right? That's, that's the shift that I wish, like, at least 25% of those people could have done that and been in a totally different position.

• 43:04Andrew Wilkinson?

  Yeah, I see so many people do this too with startups, where they, they go, you know, my goal is financial freedom. And then they go and start a venture back startup. And it goes back to that roulette versus poker, where it's like, look, if you just started a boring business, like a trash hauling business, or window cleaning business, or whatever it is, you get it to one or $2 million of cash flow, sell it or hold it, you're set for life. And instead, they go off and they raise all this money. And they don't realize that they really have a 1%, you know, call it a 1% to 5% chance of success, and maybe a 10% chance of like, an okay outcome, where they basically just make whatever they would have made over 10 years in a payout, you know, if they had just done that or something. I feel like so

• 43:48Andrew Wilkinson?

  many people are trapped in that way of thinking. And I think there's this other great book that really inspired me with mine, which is called How to Get Rich. That's the best book. I mean, that's by far one of the best business books I've ever read.

• 44:01Andrew Wilkinson?

  I read part of it. I read like a third of it. The book, I mean, the real, the real takeaway is it's similar to my book in some ways, right? Where it's like, at the end of the day, the money like ruined, the money like ruined him, right? He became like addicted to money. And he basically in it goes, look, all my life I wanted to be a poet. And instead I got obsessed with money and addicted to drugs. And I wish that I just quit at 35.

• 44:25Sam Parr?

  He said, uh, he goes, he goes, I was a, I was a punch drunk boxer. But instead of boxing, it was making money. And I ended up spending a hundred million dollars on crack and whores. Cause he actually became, he was a crack addict. And he died with a partner and that was a prostitute. Like his, his then girlfriend was a prostitute he met. But the book has like 10 or 15 chapters and each is a different lesson. But the main takeaway is that he's a really wealthy guy and he keeps it real. Beautiful writing and he talks about how, uh, yeah, he got, he got drunk on it.

• 44:59Andrew Wilkinson?

  And he, he talks about, I mean, this kind of thing we've been doing in this episode where we talk about the levels, right? What are all the different levels of wealth and what do they mean? And I remember reading it when my net worth was like 500 grand. And he's saying, oh, you know, if you want to be really, if you, you might think like 50 million is a lot, but that's actually nothing. You know, here's what you got at 250 million.

• 45:20Shaan Puri?

  He's got like the comfortably poor, comfortably rich.

• 45:24Sam Parr?

  Yeah. And he's got a very, and all the levels are quite high. You read that, you get very humbled. Are you looking at the levels right now?

• 45:31Andrew Wilkinson?

  Yeah.

• 45:31Sam Parr?

  So he has, he has two of them. He has levels of non liquid money and then he has levels of liquid money and.

• 45:37Shaan Puri?

  So he says wealth measured in cash in hand or quickly realizable assets. So kind of like liquidish assets. And what he says is a hundred to 400K, that's the comfortably poor. 400 to 1 million, the comfortably off. One to 2 million, the comfortably wealthy. And then it goes, the lesser rich, the comfortably rich, the rich, the seriously rich. That's 70 to 100 million.

• 45:57Sam Parr?

  What does rich start at?

• 45:58Shaan Puri?

  100 to 200, the truly rich. And then over 200 million, the filthy and super rich.

• 46:03Sam Parr?

  Yeah, it's a, it's a great chart that he made. I love that chart.

• 46:06Shaan Puri?

  Yeah. And by the way, like I, I guess for what it's worth, even though I just went on this rant about like, how you can kind of reverse engineer financial independence. I gotta disagree with one thing that you said, Andrew. So I think you, you have a, I think, am I characterizing this right? I think you have a belief which is like. You should kind of like focus on these increments. It's like get to the 250K, get a few million in the bank and then like start, then you start kind of finding your life's work as you, as you go, right? You can decide how much money you really want, get to, get to your enough number and then figure out your life's work. Is that correct?

• 46:36Andrew Wilkinson?

  Yeah, but I think that if you overshoot, that it causes a lot of stress.

• 46:40Shaan Puri?

  Right. I had a meeting once, I want to tell you guys about it. My company got acquired by Twitch and Twitch hires this new guy, the guy who's currently the CEO of Twitch. This guy, Dan Clancy. And I go into Dan's office and he's my new boss and he's like, all right, yeah, I want, I want to do a one-on-one. You're one of, he has like five direct reports on one of his direct reports. And he's like, uh, you know, I always with my, I want to have a good relationship. I want to understand where you're trying to go and then I can help you get there. So like, you know, what's the dream for you? You, you're like an L, I was like an L7 at the time. He's like, you want to get to L8, like, you know, the, like, the little ladder they create inside the company. Uh, and I think L10 is like the CEO and there's no nine. It's like some weird system where you get to eight, then you either get to 10 or you don't get there.

• 47:19Andrew Wilkinson?

  Going, going clear in Scientology.

• 47:21Shaan Puri?

  Yeah, exactly. I think Bezos is a 12 or a 13 or something like that. And like, that's the top level. So he's like, what's the, what's the goal? And I was like, I, in my head, I was like, do I tell this guy? I don't really give a fuck about being at this company or do I have to lie and pretend I want to be here? When I'm really just vesting out for like the next year. I was like, all right, let's go with the truth. So I go, honestly, like, uh, I did this deal. That's how I got here. That amount of money kind of matters to me. I want to vest that out. I want to have fun while I'm here. I want to do good work while I'm here. I want to meet cool people, but honestly, like not looking for a long-term fit here. You know, there's not a one night stand. It's like a one-year stand for me. And I tell him this and he said, okay, great. He doesn't flinch and I'm like, okay, I respect this guy. And he, uh, he goes, I don't want to waste my time then trying to figure out like, you know, your path here.

• 48:06Shaan Puri?

  But he's like, I also don't want to check out on you. And I was like, oh, thank you. I was like, that's my hesitation. I didn't want to tell you that because I didn't want you to just totally write me off as like a guy you don't want to spend any time with for the next year. Cause I'm not a part of the long-term. He's like, no, no, no. And he goes, um, so tell me, what is the plan then outside of here? And I go, you know, um, and this is where I went to like, uh, this is how I used to think at the time. I had this insecurity, which made me want to say something very ambitious. I thought, you know, I live in Silicon Valley and so, you know, in Hollywood, you're measured on your, your beauty and your IMDB. In Silicon Valley, it's how ambitious is your story? What, what are you trying to change and disrupt and all this stuff? So I said, I said, I really want to start a school, like a university. So I go to the speech and I tell them this thing, and I don't know if you guys have ever done this,

• 48:49Shaan Puri?

  but you, you have your material as an entrepreneur, you're saying it to your employees, your investors all the time. You have these speeches and you kind of know the reaction that you get. And if you always get like a nodding, like, oh, wow, that sounds great. Sounds really well thought through. That's a great framework for that. You start to get used to that. So I give them my framework. I say, to do this, you need three things. You need skills, you need capital, and you need connections. And what I'm doing right now is the next three years, I'm building those three up. I'm building my capital by being here. I'm building my skills by doing this. I'm building my connections by, you know, doing this. And that's what I need to do the thing. I give them this whole speech and I'm so used to people being like, oh, that sounds really well thought through. You know, it sounds great.

• 49:22Sam Parr?

  He's gonna be like Mark Wahlberg in The Departed, being like Hawthorne. Like, come on, man. Like, get rid of that.

• 49:28Shaan Puri?

  That's literally what he did to me. He goes, nah, I don't buy all that. And then he doesn't even tell me what. I'm just like, okay, um, well, that's all I got. So, so what do you want me to say? He goes, I don't believe in the deferred life plan. He goes, anytime I, he's like, I'm older and wiser. He's like, you know, I just, if I ever hear somebody who wants to do something and then they give me a bunch of reasons why they're not just going and doing it right now, it tends to be a bad decision to not go do the thing you want to do. He's like, it's okay if you don't know what you want to do. Then sure, you, you go wander around, you try to figure it out. But if you know, you're, he's like, you're an entrepreneur. If somebody told you they wanted to start a business, would you tell them, first go to business school, read these 10 books first, then go start, uh, you know, go, go do a practice session doing this, go hire a coach?

• 50:12Shaan Puri?

  No, you tell them like, start the business and you'll figure it out as you go. That's how you, how you get good at business by doing business. There is no real substitute to getting good at the thing besides doing the thing. And he goes, if you want to do that, you should go do it. I don't believe in the deferred life plan. And ever since he said that to me,

• 50:29Andrew Wilkinson?

  You know, there's something good about getting just like served like that, just getting owned to your face and you're like, huh, thank you. That was like a real gift that you gave me because you could have just like everybody else just nodded along and said, all right, sounds good. Good luck. And instead, he kind of shook me up a little bit and changed my frame on that. And so that's the only one thing I would say, Andrew, is like you have this thing of like, go figure out your life's work, which is, I don't know, maybe a better plan is to like, start by saying, what do I really love doing? Or you loved designing websites, designing products. And you might have just been happy you're doing that. And you might have made as much money if you had just like gone for that versus, I think the way that maybe you do things, but definitely the way I did things, which was, first, I'm gonna go make the money, then I'm gonna do the things I want. And actually, as I look back now, and if I was gonna give advice to myself now, I would say, I don't think you

• 51:12Andrew Wilkinson?

  need to do it that way. That works. That is one way, way to work, to make it work. But you might be better off just going and trying to do the thing if you know what the thing is. You know, do you know that parable, the, the fisherman and the businessman? You know that one? Yeah, love that one. So good. So, okay, so, okay, so, uh, there's this like, you know, Wall Street guy, and he's on vacation on a small tropical island, and he sees this man who's fishing down by the water. And he walks up and he says, hey, what are you up to? And he says, I'm fishing, um, for the morning, and I'm gonna get a fish, and I'm gonna feed my family. And the guy goes, oh, will you ever think about turning that into a business? And he goes, well, how, how would that work? And he says, well, first, you get a couple other buddies and you fish more,

• 51:53Andrew Wilkinson?

  you get more fish, and then you sell them at the market. Well, and then what? Well, and then you would, uh, buy a boat, and you'd be even more efficient, and you could freeze them, and you could ship them all over the world, and you have a great business. And then he goes, well, and then what? And then he says, well, you did then get a fleet of ships. Well, and then what after that? Well, and then you take the company public. And then what? Well, and then you could retire, and you could just fish all day. And so the joke is, like, the guy is already doing the thing he loves. Why would he go and build this big business? And I think it's like, look, do you want to chop wood in your backyard? Or do you want to own a sawmill? Do you want to be Jiro from Jiro Dreams of Sushi, or Steve Ellis from Chipotle? I think that is the ultimate question

• 52:38Andrew Wilkinson?

  of like, what is your happy place? And how can you optimize your life around being in that?

• 52:46Sam Parr?

  Yeah, I mean, I remember one time I told that story and I was like, "Wait, what's the punchline?" You remember that, Sean? I was like, I told the story and I'm like, "I'm not really sure what the takeaway is, but uh,

• 52:57Sam Parr?

  like, should I go and uh, like, fish or I don't know. Do you remember that? No, it's a good story, though. But Andrew, when um, when's the book officially come out?

• 53:09Shaan Puri?

  July 9.

• 53:10Sam Parr?

  It's actually a great book. Like, I have a lot of friends that have come out with books and Never Enough is actually one that I sat down and read the entire thing, not because I was trying to be your friend, but because I thought it was awesome. The writing's good. What are you looking at, Sean?

• 53:25Shaan Puri?

  I'm looking at the book. Well, I had the same reaction. I would have said it's a good book anyways because I'm your friend, but it actually is a good book. I read it in like three nights, basically.

• 53:31Sam Parr?

  I read it when it was still a PDF.

• 53:33Shaan Puri?

  There's three, there's three good stories I remember from it, Andrew. So there's the, the Charlie Munger story. So it's basically the uh, the crazy way that you actually ended up meeting your hero and kind of almost doing a business deal with him. There's the Pixel Union sale and then buyback story. I thought that was a great one of kind of like your first big win in terms of an exit. And you shared the numbers and you talked about how it went down and then like how it went slightly wrong. I liked that story. Um, and then the last one, I won't, I won't give away the ending, but the ending is dope. And uh, the ending was so good. I was like, did he just do this for the book? Like, I was like, did he just make this ending so like, he needed a good ending for the book? So he just did this thing in real life? Or was that real? But it was, it was a very good way to end the book. I liked it. It's all, it's all real.

• 54:16Sam Parr?

  Um, dude, thanks for doing this again. And uh, Never Enough, what's the best place to buy it? A website or Amazon? Does it matter?

• 54:24Shaan Puri?

  Yeah, just go to never, neverenough.com. There's all the links there, or you can just go on Amazon and buy it there.

• 54:28Sam Parr?

  And that's the pod.