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. For free. Like it was fun. All right, what's up? We got our friend at 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. I think it's a very simple design slack and a bunch of other popular Silicon Valley products that you may have used. Started buying businesses, read about Warren Buffett, read about Charlie Munger, started buying businesses, now owns like, you 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. Your skin looks great. The glow looks good. You seem happy. You got that non-operator glow. All right, let's take a quick break. I got to tell you, you've ever seen those Coachella posters where it's got all the artists names and you're like, oh my God, wow, they got, you know, friend again and squirrel eggs. And that's what the HubSpot inbound conference looks like. Just listen to the speaker list that they have. I don't know how they pull this off, but listen to this. Ryan Reynolds, Serena Williams, Cara Swisher, Matt Wolf, Dharmesh, they got Brian Halligan.
They got tons of good speakers at HubSpot inbound. It's coming up. It's September 18th to the 20th. It's live in Boston. And it's where you go. If you want to learn marketing sales, AI trends, you want to know where the puck is going so that you can be there before everybody else. Tons of great talks on stage where you're going to learn sales strategies and proven marketing tactics, but also the networking where you get to meet other people and understand what are other people in the industry doing, how are other people getting ahead. So check it out. Go to inbound.com to see the lineup and grab your tickets today.
Enough about talking to how much of a babe you are. All right. So Andrew, I sent you a voice note. You start 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. 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. Well, so you go from barista, you start designing websites.
So you go from $6.50 an hour to $60 an hour. And it sounds like that might have been somewhat happenstance. Did you, was that intentional to make that shift or just kind of you got an opportunity? Oh, lucky balance came your way. What made that shift happen? So I was working, making coffees every day for all the people who 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 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. 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 website.
And within a couple of weeks, I'd quit my job. Wait, did you know anything about design? 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. Do you remember who you approached that first one? Yeah, it was a pulled pork barbecue joint. And there is this place called Pig here locally.
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. That's pretty awesome. 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. Free. Like it was fun. It was fun designing websites and coding websites. The first money I really ever made outside of like a college job, what I was in school was I actually won a business plan pitch competition and we won $25,000 of cash.
And they made some NBA, some grad business school student work for us for five K. It's a one $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 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 a big jump because we didn't have to get a job. So it was freedom. 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 we got to go do the go try the thing we wanted to try, you know, together as friends.
That was probably the first level. And like Andrew 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. 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 and 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. I like to have a $24,000. I felt incredibly wealthy. 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 just sort of keep working blindly. They'll put in the bank and then they don't really know how to use it, what to do with it.
我感觉自己好像在说,“去澳大利亚吧。就像是说,去生活吧。去旅行吧。去泰国吧。” 当时我手里有两万四千美元,感觉自己非常富有。顺便说一下,把钱转换成时间而不是金钱是一种很有力量的做法。你知道,如果你有两万四千美元、三万六千美元或九万美元,就像是在Chuck E. Cheese那种儿童乐园里的代币,你不太明白这些钱能为你做什么。而大多数人只是盲目地继续工作,把钱存进银行,但他们并不知道怎么使用这些钱,该做些什么。
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 rates a lot higher, right? But, you know, were you slept on air mattresses? It's like, well, why do we need, you know, and then we got to, you 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 dominate things when you don't have a huge sum of money. 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 was $250, I wrote $250 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 use an app.
Alright, 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 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 going to 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.
Alright. So 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? 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 design or 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, Canadian. So it's very sweet. 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 is literally just my girlfriend's best friends, 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 going to get negotiated down by this client.
And so I go to the client and I say, it'll be a thousand bucks. And they say, okay, sounds good. And so in that moment, I was like, Oh my God, I just made $500. And I did absolutely no work. So that's that 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. That's great. Yeah. 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 being an absolute rookie at it?
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. 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 and call it. I can buy beer. I can go for a nice dinner and stuff. Wait, how old were you when you made your first, is that million profit? Yeah. I think I was 20, 22 or 23. That's huge. That's huge. Oh, yeah, it was amazing. You didn't go to college, right? Or you dropped out. I dropped out of college. I went to journalism school for like two or three months.
So you did a million in profit two years into being an agency. I started when I was 19 years old. And so probably four years in something like that, three or four years in. That's massive. 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 it was like, it was very eight hundred dollars. You're like, okay, well now what? My taste still even match my, my, my income right now. Yeah. It was very, it was very kind of empty and hedonistic. Do you ever read Rich Dad Poor Dad Andrew? Yeah. He has that. Uh, Sam, you've read that book. He's got that. No, thing. Do you know about that? Yeah. People hate on that guy. I'm not sure why, but what about it?
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, course, he sell 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, he 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 end point. 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 employee to self-employed. That's what you described barista to solo freelance web designer. Then you go to be 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. Um, and so you, and eventually with time that you became, ah, you became an investor, but like this path going from ESBI 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. You need to save the princess from the castle. Um, it's like, Oh, once I know that now I could 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. And that was in level two for you was between what a million dollars a year and what was your upper limit? Yeah. I mean, I was paying myself 500 to a million a year and I was profiting more than that. And I started, uh, 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 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 dollars. Um, 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. Uh, I had no filter whatsoever. And it was really exciting, frankly, like I was just, I was constantly starting new stuff.
Starting a restaurant is an awesome way to lose money though. Oh yeah. And I lost, uh, I think I lost a million bucks doing that. Cat furniture, uh, restaurant, skin cream, SaaS company. You tried, uh, 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. Um, we had a concierge service. What was the viral blog? We had clients from hell. It was like really big on Tumblr for a while. Do you know it? We basically we would, we would have all these like, um, 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 would received and stuff where that'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.
Dude, we need to bring back Tumblr. Tumblr was great. I love the, I love the Tumblr days. I, I still go back and I'll read old people's tumblers. 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. I made so many friends from Tumblr and I still meet people like at conferences that know me from Tumblr back in the day. What age were you when level three ended or level two ended? Um, I ended that probably like 27. I think that was when I sold my first business.
What did you sell for? And what was it? So I sold it for 7 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. Um, and Harley as well.
In 2010 at a conference and at the time, Shopify is 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 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, right? The iPhone app store. And I was like, Oh, 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. A month, like basically immediately. And what year, what year was that? 2011, probably 2010, 2011. All right.
2011, you're doing 20 or 30 grand a month. Is this called pixel union? 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 cause 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, 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, 100,000 or something like that on the chip. 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. And so there was 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 and 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 when I read about Warren Buffett, that changed everything for me.
What I what I ended up doing is I had all the incubated businesses. I actually shut almost all of them down. And I'd sold 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 in 20% of it. And then metal 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 in a 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 bought like a responsible nice house. I bought, you know, a nice, a nicer car, I 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? So basically I was like, 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 post tax or pre 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 got to live like a popper and then I got to become a prince. I got to 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? What the fuck is a popper? Popper tendencies you had as Sam chugged a Dr. Pepper while you were talking. So Sam, what were you doing when you were building the hustle? How did you live? Were there any cheap skate?
Oh, yeah. So my wife worked at Facebook at the time. So dinner was like I gave her top wear containers and she would bring home prosciutto and cheese because they always had like shark food reports. I was dinner was sponsored by by meta. Yeah. So we I was on a prosciutto diet because that 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 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, it's just startup funded. I was like, no, but we are fueled. We're fueled by VC, but we're not funded. And so I did 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. Yeah, there's nobody checks on San Francisco. They did. I get trouble all the time, but they would say, you know, do you have your ID? I'm like, I don't have an ID. So I'll tell you, you know. But yeah. So hopefully there's a statute of limitations on these things. Cause I definitely broke the law a little bit. I was also on a whole food scholarship as well. Let's just say that the, the, the hot bar was right next to the exit.
So, so Andrew, you, when you were spending 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're like, no, no more 20% rule. You changed it to some other rule, right? Right. What, what did you shift to? 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, uh, But not because you're spending less.
No, not necessarily. I mean, in some cases I was spending more than 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 in 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, every single company, I was the CEO of that. So as me and Chris, I'm the 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 a 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.
但实际上,大部分时间我是经历了一次重大的突破时刻,意识到自己不必一定要当 CEO,不必一定要自己经营公司。那时,我在每家公司都是 CEO,我和 Chris,他是 CFO,我们在不同的业务之间就像无头苍蝇一样乱转。然后我读到了关于沃伦·巴菲特的故事,顿时觉得太不可思议了,这个人把商业简化到了极致,他几乎什么都不做,只是读书和一年买一家企业。能够雇一个 CEO 来管理你的公司这个想法对我来说简直太疯狂了。
Like I think a lot of people have this feeling around, you know, why would someone come and work for me? I felt like that all the time. I felt like, yeah, you're like, what are you doing? Yeah, this is 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. 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.
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. 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 Stewart, 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. 25 million dollars of angel investments. That's a ton, maybe even 30. That's an insane amount of angel investments. What? That's basically irresponsible, my friend. I know. I know. This is the problem with the invest in X is not going to return all that money.
How do you, why do you think you've returned $30 million? I don't think that no, no, I'm not saying I've returned 30 million. I've literally put $30 million in adventure. I don't, but you say you've brought, you may be broken even, right? You think you think you've no, no, no, no, no, no, no, no, to be clear. I think you were so full of shit. You're telling me you don't have a spreadsheet that just like if I have 30, no, my friend, no, it didn't matter.
I don't know. 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. No. So I actually have, when I say I returned, I mean, from that cohort. So like maybe I invested like two or three million dollars over that period. And I'm saying I might have got that money back, but the rest, most, 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 marked 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 I think it sounds crazy, but that is actually more par for the course, I think, for the way Angel investing works. Because I think if you're listening to this, you don't know Angel investing, it sounds insane.
And there is a bit of it that's insane. That's a very big number to put into it. But these are like 10 year odysseys. People stop sending updates. Even when they raise it up rounds, you're done 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 a reality situation. And a company will raise money.
It's a huge valuation. And then a year later, it's going out of business. And so 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 counted as my net worth, by the way, as the principal I invested, but half.
Totally 100%. 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. 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 talked 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 bet on Stuart Butterfield when he was building a game and then it turns into slack.
And, you know, did you know, you might have known that Stuart was good, but did you really know? You know, and I think a lot of people attribute skill to where there was luck or not, not the other way around. So 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 know what their average returns are for the last 15 years, that's some P500. 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 forex your money just doing that boring shit, but that's way more boring.
Yeah, that's the thing. I think 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, $100,000 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. Yeah. All right. First of all, thank you for sharing all those levels because it's interesting, Ed. 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 areas.
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 learned 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 on here. Do you really need to be a billionaire? What are your thoughts on that? I we forgot one level. We forgot one level. What's the last level?
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. Before I had anything, I would want to pump my own chest all the time because I felt like I haven't lived it 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 the 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? Because I wish somebody had told me. It's kind of like, um, oh, money didn't make you happy. Yeah, 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. Um, what did surprise you? Well, I think what surprised me was the weight of the money, right? So, you know, we have wrote in this in the prep talk, but like this question of like, do you really need to be a billionaire or do you want to be a billionaire? But you wanted to be. 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 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 because A, it's wasteful. You don't want the food to go bad and you got to do something with the food. And so the book, frankly, is like, it's kind of like a letter to myself. Ten years ago to say like, hey, you don't need to go there. Like just like good things are not where you think they are. 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 return. So you're doing a good job based on how much money your clients or your 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 is this how you'd spend your time regardless? 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 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 their businesses, that like I'm really happy doing that. I love doing that.
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 would you write down on the pen and paper to figure that out? 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? What do you think you would want to spend every year 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 two million dollars.
And then you want to buffer. So call it three. And that allows you, you know, you basically go and you get into hobbies and toys and you collect cars or do whatever you want. Right. So call it three million bucks. So what's three times 20? So 60 million dollars. I think 60 million dollars. If you've got it liquid, that's, you know, you can live an incredible life and spend three to four million dollars a year. And it's awesome. So that's your target. I think about it. 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?
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 that you really want to get to. Call it 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.
Sean, have you done the math? Like have you thought about that for you? Yeah. What's yours? Yeah, 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 dollars a year. And then I tried to do the four or five percent, assuming that that's four or five percent of your total. I forget what it was. I remember getting to six 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 six million. That's the target. And I drilled that into my brain. I said financial freedom is at six million. Six million means I could spend whatever I want.
And I made it like part of my like all of my passwords when I would log in. I had the number six 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, I was the right way to think about it. 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. 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, 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, some of them between five and five and 10 X multiple depending on what industry you're in.
That's not a hard way to get to 10 million. It's hard, but it's simple. 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, a 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 went on LinkedIn and I searched my college class. So it's like, okay, let me go look at Duke 2010.
Dude, that's my, that's my Friday night routine. I do it every Friday night at one o'clock. I literally do this on a Friday night. I got it all by schedule. I got a reminder on my calendar at one o'clock a.m. Friday night. I got a, like, 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 fdup 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 of 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 so I was scrolling through it. I was looking it up and it was amazing. Man, these people who I know these people, these people were smarter than me, harder working than me, more talented than me. They're doing like just kind of random jobs. And I texted my college roommate and I was like, man, it's crazy that like this person, this one girl, I remember, 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, 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 year had come and said, look, how much do you even know how much money you want, indeed?
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 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 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, here's what you could start a business. I guess to 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 has 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 it 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? 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 yeah, I guess like this along with the 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. And 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, you know, at least 25% of those people could have done that and been in a totally different position.
Yeah, I see so many people do this to a startups where 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 one 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'd just done that or something. I feel like so 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 as the best book. I mean, that's by far one of the best business books I've ever read because 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 want it to be a poet. And instead, I got obsessed with money and addicted to drugs. And I wish that I just quit at 35. He said 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 $100 million on crack and whores, because 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, yeah, he got, he got drunk on it. 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 might think like 50 million is a lot, but that's actually nothing, you know, here's what you got at 250 million, it's got like comfortably poor, comfortably rich. Yeah. And it's a very, and all the levels are quite high. You read that you get very humbled. Are you looking at the levels right now? Yeah. He has two of them. He has levels of non liquid money. And then he has levels of liquid money. And so he says wealth measured in cash in hand or quickly realizable assets. So kind of like liquidish assets. And what he says is 100 to 400 K, that's the comfortably poor, 401 million, the comfortably off one to two million, the comfortably wealthy.
And then it goes the lesser rich, the comfortably rich, the rich, the seriously rich, that 70 to 100 million. What does rich start at 100 to 200? The truly rich, and then over 200 million, the filthy and super rich. Yeah, it's a it's a great chart that he made. I love that chart. Yeah. And by the way, like, I guess for what it's worth, even though I just went on this rant about how you can kind of reverse engineer financial independence, I got a disagree with one thing that you said Andrew, so I think you have it. 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, like get to the 250 K, 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 it, get to your enough number, and then figure out your life's work. Is that correct?
Yeah, but I think that if you overshoot that it causes a lot of stress, 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 to do a one-on-one, he has like five direct reports, I'm one of his direct reports, and he's like, 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're like an L, I was like an L7 at the time, so you want to get to L8, like, you know, the like the little ladder they create inside the company, 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 get to 10, or you don't get there. Going, going clear in Scientology. Yeah, exactly. I think Bezos is a 12 or 13 or something like that, and like, that's the top level. So he's like, 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, I did the steals, 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 does a flinch. And I'm like, okay, I respect this guy. And he goes, I don't want to waste my time then trying to figure out like, you know, your path here. 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, because I'm not a part of the long term. He's like, no, no, no. And he goes, tell me what is the plan that outside of here? And I go, you know, and this is where I went to like, 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 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 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 him this thing and I don't know if you guys have ever done this, but you give your material as an entrepreneur, you're saying it to your employees, your investors all the time. You have these speeches that you kind of know the reaction that you get. And if you always get like a nodding, like, 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 him 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 doing this. And that's what I need to do the thing. I give him this whole speech.
And I'm so used to people being like, Oh, that sounds really well thought through, you know, sounds great. He's gonna be like Mark Walberg in the department being like Hawthorne. Like, come on, man. Like, give it a literally what he did to me. He goes, yeah, I don't buy all that. And then he would tell me what I'm just like, okay, 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. It goes anytime I he's like, I'm older and wiser. He's like, you know, I just if 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 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, you know, go do a practice session doing this, go hire a coach. No, you tell them like, start the business and you'll figure it out as you go. That's 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, 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 I really love doing.
Or you loved designing websites, designing products. And you want to just been happier doing that. 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 about definitely the way I did things, which was first, I'm going to go make the money, then I'm going to do the things I want. And actually, as I look back now, and if I was going to give advice to myself now, I would say, I don't think you 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 fishermen and the businessman? You know that one? Yeah, love that one. So good. So okay, so 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 for the morning, and I'm going to get a fish and I'm going to feed my family.
And the guy goes, Oh, will you ever think about turning that into a business? And he goes, well, how would that work? And he says, well, first you get a couple other buddies and you fish more, you got more fish, and then you sell them at the market. Well, and then what? Well, and then you would 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 didn't 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 Els from Chipotle? I think that is the ultimate question of like, what is your happy place and how can you optimize your life around being in that?
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'm not really sure what the takeaway is, but like, should I go and like fish or I don't know. You remember that? No, it's a good story though. But Andrew, when's the book officially come out? July 9th. 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? 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. I read out when it was still a PDF. There's three, there's three good stories. I remember from Andrew. So there's the Charlie Munger story. So it's basically the crazy way that you actually ended up meeting your hero and kind of almost doing a business deal with them.
There's the Pixel Union sale and then buyback story. I thought that was a great one of kind of your first big win in terms of an exit. And you shared the numbers and you talked about how it went down and then how it went slightly wrong. I liked that story. And then the last one, I won't give away the ending, but the ending is dope. And 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 he needed a good ending for the book? So he just did this thing in real life? Or was that real? But it was a very good way to end the book. I liked it. It was all real.
Dude, thanks for doing this again. And never enough. What's the best place to buy out? A website or Amazon? Does it matter? You just go to never, never enough.com. There's all the links there or you can just go on Amazon and buy it there. And that's the pod.
兄弟,再次感谢你帮忙。真的非常感激。买东西最好的地方是什么?是一个网站还是亚马逊?有区别吗?你只需要去 never, never enough.com。那里有所有的链接,或者你也可以直接去亚马逊买。就是这样啦。