In my free time, I changed my information diet. I started watching podcasts and YouTube videos. I swapped it out. It's like, all right, that Netflix time, now this is learning time, right? That mindless, you know, Kardashian stuff, that's going to become people who have the thing I want or are chasing the thing I want. And I started to identify a bunch of cool people. That's the first part. They did two things. They looped me into projects that they were doing so I could join their project or I could invest in their project. Or they just taught me like different paths to success. There are like a million different ways to win. When I started, I didn't know of any. When, as I've grown, I've realized, wow, there are actually a million ways to win at the end of the day. It's just going to be about picking which one's the right one for me. But the first exercise of getting around the right people is they will increase the number of options on the menu of different ways to possibly win. So for example, you said, I've sold a newsletter for millions of dollars. Well, guess what? I used to hang out with Sam Parr who built the hustle, who sold the hustle for tens of millions of dollars. So when I want, so I knew that was a blueprint and I used it. I used that blueprint. I did it for crypto. I built the largest crypto newsletter in one year and then we sold it. And it was like easier than all the other businesses I did because I was around somebody who had taught me that blueprint. E-commerce. I have an e-commerce business that will do 20 million plus in revenue this year, profitable bootstrap business. Well, how did I come up with the idea for that? I was hanging out with people who had made their money that way. I was interested in a guy who told me he had made 20 million. His dog ramp business would do 20 million that year. I thought, what a weird idea. Dog ramp, man. Like literally like for dogs to get up on the bed or down from the couch. And he was selling dog ramps. He sold $20 million of dog ramps. And I was like, damn, if this guy could sell $20 million of dog ramps, I could do anything in e-commerce and win. And I used to hang out at his house and understand what he does. And he taught me Facebook ads and he taught me how to do it. And I was just a sponge. I wanted to, and I would help these people, right? Like they wanted help in other areas. I would help them. They would help me. That's kind of the core mantra. So when you ask what shifted and how did I start to have success in these different areas, it started with changing my people that I hung out with and how I hung out with them and being, and paying attention to it. All right. So then the other part is doing cool shit. So everybody has a different taste profile and that is your advantage. Nobody has the same taste as you. Nobody could build the podcast that you've built because you think a certain thing is cool. And you explored that to the edge of the frontier of that. I've seen how you, how you prepared for this podcast. You called me and then you worked with me on the story and you said, no, we don't want to talk about that. We want to talk about this. And you know what really resonates is this. And you sent me this thing about, here's the listener avatar. It's Darren and he's at his job and here's how Darren is feeling. You have explored that. So the do cool shit is dabble, try a bunch of things until you find the things that interest you. Let what's exciting be the guide, meaning, uh, the excitement should be the thing that got, it's like your compass. It tells you which way to go. Just follow your excitement. Your excitement is a thing that is unique to you and it will lead you to a place that it won't lead everybody else, which means there's less competition. Um, and it will, their excitement will also let you keep going beyond just the nine to five. Like when I'm excited about something, dude, I'm up all night reading about it, thinking about it, talking about it, doing it. So I have a competitive advantage. I can get good really fast if I do things that I'm interested in because I won't just do it during my work time. It's also my play time. So that became the next shift I made. I created this podcast. I did not expect the podcast to be successful. I didn't expect to have, you know of downloads and make millions of dollars for talking. It ended up that way because I just followed the thing that was exciting and interesting to me. And I followed it to like the nth degree. And I just thought about it all the time. And I worked on it all the time. And not because I was trying to grind or trying to work hard. I was just interested in it. It didn't feel like that hard to work on it. Felt fun to work on it. And so I just kept doing it. And because of that, I ended up in this really unique place with the podcast being, um, you know, this amazing business where like, I can't emphasize this stuff. I get paid millions of dollars to talk to my friend for two hours a week. Like there is no better job than that. I spent my 20s seeking a great business. And in the moment where I stopped trying to find the opportunity, I just said, what's the most fun thing I could do right now? What's the most interesting thing I could do right now? That's when I actually found the best business I ever built. Right. And so there's example after example that I'll pause though. So you can take this wherever you want to take it.

Yeah, no, that was so good. Even, even you gave away my secrets, I didn't love that, but you gave away the secret source of how I do this. No, what you said is so good. And you spoke about excitement. And I remember reading this, I believe it was on Twitter, or maybe I heard it on a podcast. But I don't know, I just have a feeling that you also saw what I what I'm about to say, which is, was it Paul Graham that said it? I don't remember. But the basically what was said is that if you're looking for business opportunities, if you're looking for your million dollar idea, just look at what are the nerds getting excited about that was like the framework it was like so for example 20 30 years ago the nerds were getting really excited about this thing called the internet and like all of this stuff and for everyone else they were like uh this is just like a fad this is gonna play out like it's not gonna work but the nerds were fascinated by it And the phrase

is from Chris Dixon. He says, what the nerds do on the weekend, we will all be doing in 10 years. Yeah. So back in 2012, when the nerds were like, there's a cryptography, the cryptography proof by Satoshi Nakamoto, right? Like it's like, what are these words you're saying, dude? Like this thing called Bitcoin, it's this internet money. And they were interested in it because of the novelty. They didn't all expect to get rich off of it. They just thought it was so cool, so interesting. I had friends in my office that were telling me about this. They were doing it in their spare time. And I was like, guys, come on, can we pay attention to something serious here? And it's like, stop talking about this Ethereum. I don't know what the hell that is. Sounds like the biggest dork shit I've ever heard. And it's like, actually, what I should have been doing is paying attention to what my nerdiest friends were interested in. Or even better, lean into what I am nerdy about. Watching what other nerds do is great for investing. Figuring out what your inner nerd is and unleashing your own inner nerd is how you come up with your own projects, your own ideas that are going to work for you. And by the way, I think this is one thing that everybody gets wrong because they go follow your passion. And passion is this loaded word that's like love. And when you sell somebody, follow your passion, the problem is not that they're not following it. They just don't know what the hell they're passionate about. They don't even know, is this stuff that I like? Is that my passion? Comic books, is that my passion? What are you talking about? And so passion is this loaded word. People don't really even understand it. They don't know what their passions are. And so they don't know what to do with it. Excitement or interest is just a much less loaded word. It's like dating where passion is like marriage. And dating, I think is a really good analogy. So for the first 10 years, I would say expect to just dabble and date. So pick something. You don't know how long you're going to, it might be a fling you do for two weeks. It might be something you do for six months. It might be something you do for two years. You don't know. Do it while you're interested in it. As long as you're interested in it, keep going. And every project you do is like dating. It will have its ups and its downs. And ultimately it'll teach you what you want out of, you know, when you're dating, when you date somebody, you learn what you really want out of a partner. And you also learn, man, where am I a bad partner for other people? Where do I need to level up? And that's exactly what picking these projects and sort of dating is going to do in the business career, in your business life too, which is it will have some fun. It'll have some ups. It'll have some downs, but ultimately it teaches you what types of projects you actually want to be doing and you'd like doing. And it'll show you where you're weak and where you need to get stronger. It'll show you where you're strong that you should actually double down and lean into. Nobody teaches you this. Nobody tells you this. But like, that's the one thing I would really encourage. Like, you know, when my kids are 21, my kids are 25 years old. I'm going to make sure that like, you know, you need to be in a season of dabbling. Like you need to be dating around with different projects and different industries, different company types, different careers to find the thing that's like lighting you up. You're not expected to just know your passion upfront. Like you figure it out by just following your interests. And sure enough, like over time you get to figure out what's your thing.

You know what?

You,

you use the word, uh, seasons. And I actually think that for someone that's looking to go from living like quite an average experience to something great, something that's one of one, the mindset of thinking about things as seasons is extremely important, at least in my experience. I remember one of the things, and this goes back to my experience being at living with my mom for a year as I was building my business was I would have these like, frustrating moments. I remember one time, actually, so I used to go into New York to record the show. So I'd be living in Jersey, like in the suburbs in the middle of nowhere, like the majority of my week. And then I'd have like this one experience of going into New York, which I loved. And there was one time I had just recorded and I was heading home. And for some reason, I was just around where my old office was, like the company that I used to work at. And I remember seeing, it's weird, like, it was like I was watching my old life. Like I was seeing all these people, like, the way that they were walking to the subway, the way that they looked, the way that they were dressed. Like it was exactly everything that I used to do on the day to day. And I had this moment, Alex Hormozzi actually talks about this, which is like, when you're on this journey and this path, there's this point in the middle where like, you're no longer where you started, but but you're not at the end. And you're kind of in the middle. And you kind of have these situations where you start to look back to where you were in the beginning. And you get almost like wistful about it. You're like, oh, you start like reminiscing about your old life, even though, even if you didn't necessarily even like it but it's just like nostalgic and there's a comfort to it and one of the things that really helped me in that moment where I was just like I almost wanted things to return to how they were I started thinking about my life as seasons of like this is my season of experimenting of failing continuously of like having to grind and push through this thing but just as this is a season of work there will be a season where it's the opposite of this where it's like fun where things are working all of those things and it just kind of gives you that perspective like to your earlier, instead of thinking on like a year basis, it just, it just widens the time horizon. And it was so impactful for me. You know what, here's where I want to go next. One of the things that's been really cool with watching your journey and how you build businesses. You, and you know, it's funny, actually, I'll say this and I'll get your reaction and see if it's actually true. You almost have like this spontaneous approach of building businesses. This is how I think about it, which is like, I saw the early editions of the Milk Road, the newsletter that you built and sold for millions of dollars. I saw the early editions of that. And it did not feel like a business at all. It just felt like you were just writing something that was interesting to you. And then at a certain point, it turns into a daily newsletter. And then at a certain point, you're writing an email saying that we sold it and like, you know, how happy you are with the outcome. And so can you talk to people about how do you kind of like, what does almost like that testing phase look like to then going to, wait, this is actually a business. This isn't just a fun thing for me anymore. I've done the thinking of like the numbers and I've started to strategize about how this could work long-term. Like, can you get into the practicalities of that?

Yeah, yeah, definitely. By the way, I agree with your seasons thing for what it's worth. I think it's a super useful tool. Give it, give every season a name. What's your question? So I am spontaneous with it. I don't know if I would recommend that to everybody. Like impulsiveness. I'm an impulsive dude and I just do whatever feels right in the moment. There are cons to that. I have started businesses, even ones that work that I kind of regret starting because I'm like, you know, like it's like having a kid. It's like, it's years of commitment to like doing something when you do, when you start, when you have a successful business. And so, um, I don't know if I would recommend my approach to most people. I don't even know if I'd recommend it to myself. Let's put it that way. Um what's your question? What are you really getting at? You're kind of trying to ask, how do you know when an interesting experiment is actually a thing or you should turn into a business? Is that what you're getting at? What's the heart of the question?

When does it become, this is just an interesting thing that I'm doing to, this is actually real. There's something here. i almost want to know like what what's the back of the napkin math that's even happening that you're like oh this is actually a thing like this is

i could get a business i do that at the beginning so even if to you it felt like oh i'm just like i had already done that napkin math i have this little thing i called the kickoff doc um and it's basically my one page, you know, back to my 300 page embarrassment. I now have a one page thing and it's just called a kickoff doc. And I just write this before I start something just to get clear on what the hell am I trying to do? Um, so I, let's take, you know, the, the, whatever, whichever business you want to take, we can do take the newsletter business. Um, so I'll say, what am I doing? I'm going to create a newsletter that I think will be, um, uh, really popular newsletter for people who are interested in following crypto, uh, similar to, you know, like sort of like the hustle for crypto or the scam for crypto or morning brew for crypto. Okay. That was the high level of one line idea. And then I write the win and I write, what does winning look like? And I write like the floor, meaning at least this would happen. This is what I need to at least happen for this to be worth my time. Which by the way, let's say in the podcast case, I was like, the way the floor win is I'm just having dope conversations with people. And this thing costs me 10 grand a year for the production costs, but like, I'm having dope conversations. That was the floor win. And then they're like, then there's like the F yeah win, right? Which is what would it, what would feel like an F yeah where I'm high fiving? I can't believe how well this turned out. And that's like, yeah, what if we did get like millions of subscribers? And what if we were making millions of dollars of profit, but it's a really lean thing with only four or five people working on it. And some big media company wants to come by us, right? That would be really cool. That would be a really cool outcome. Okay. So I kind of define the win. I napkin math that. Then I go to the next step. I write my anti-goals. What's an anti-goal? An anti-goal is a very important step that I didn't know when I was younger, which is on the way to success, there are many ways to snatch defeat from the jaws of success. Meaning let's say you wanted to be, um, like in college, I knew this girl and her dad was a partner at some consulting firm. I was like, Oh wow. She told me he makes a million dollars a year. I was like, Oh my God, somebody makes a million dollars a year at their job. Like that was unheard of to me. And then she was like, but she was kind of down on it. I was like, you seem kind of down on it. She's like, well, he's also gone Monday through Thursday every day, every week from my entire childhood. Like he flies out of town on Sunday night. He flies back into town Thursday while I'm asleep. He's here Friday, Saturday, and then he's kind of packing Sunday to go again. And that's what he did every week, my whole childhood. I was like, oh, okay, that's an anti-goal. Your goal might be to make a million dollars. Your anti-goal is I never see my kids or my kids sort of resent me because I kind of missed their childhood because I was on a plane all the time. So anti-goals are basically things you don't want to happen that could easily happen if you weren't intentional about the way you approach this. So maybe it's like, let's say for your podcast, you want to get millions of listeners, but the anti-goal would be the thing that the algorithm likes is an episode that I'm not really that interested in. So then I just feel like I'm going through the motions, interviewing people about interviewing people. I don't care about about stuff. I don't care about it'd be a way to lose while winning. Right? So I define those and then I make my, what I call one hour, one day, one week plan. So in one hour, how can I start to get momentum and make this real? And that can't be like researching or like making a list. It's got to be like, oh, let me call somebody who I think would need this. And let me pitch it to them and see if they would actually want this, right? So it's like something I could do in one hour to get the ball moving forward. Or it might be, let me call my buddy who's done something similar and tell him my plan and get his like honest, ask him for his brutally honest take. So in one hour, I could just make some progress. Then I make a one day plan and a one week plan. So I do that upfront. And, um, and I'll usually go into something saying, if I, if I intend for it to be a business, I kind of differentiate, like there's things that are art or I'm just doing it for fun, for my own taste. And the success or failure is, did I do something dope? That's kind of the stage of my career I'm at now. I only just try to do art. I just want to make dope shit that I think is cool that I'm proud of. And sometimes the whole world agrees and I'm okay. If 99% of the time they don't agree, They don't care. And then there's business, which is like, I want to do this thing because I want it to be a successful profit producing endeavor. And I do things like that. I'll buy a company that I'm buying it because it's going to cash flow and I'm going to make X dollars a year off the cash flow of this business, blah, blah, blah, blah, blah. And I'll define that upfront. So I'm not usually going, I usually upfront will try to define that. It gives me clarity. It lets me then experiment. And even if I'm wrong upfront with what I defined, at least I stated it so I can go back and look at it and say, what changed? If I want to give up right now, is it because it's hard or because one of my initial assumptions is not true, right? I wrote down my initial assumptions so I can check against that. That keeps me honest. It keeps me from just giving up because I'm bored or because it's hard and makes it so that I really, you know, continue as long as that it's still holding true to my kind of initial reason I was excited about

this. You know, I'm going to, I'm going to ask another, another selfish question, which is, I think speaking for me personally, but I think also for a lot of entrepreneurs or people that want to start businesses, we're dreamers, right? Like we see something in the future and it's almost like we're in, our head is in the clouds of dreaming and imagining what this thing could be. And then we're pulled towards it and we get to work. And so I like what you explained about like the one page. And so I can see it even for me, if I had to rewind, I could come up with my goals. I could come up with my anti goals. I could, I could paint the picture. I could paint the dream, the vision. The thing that I would struggle with is the quantitative piece, the hard numbers. And so let's say that the ambition is to build a million dollar company. And you said that in the beginning, you have an idea of what like the back of the napkin math means. I think for most people, they have never been part of building a million dollar business. They also do not know anyone who has built a million dollar business. So the idea of like the back of the napkin math is a complete mystery. So can you kind of demystify it for us? What are the numbers that would need to even be in place if i'm just planning it out in the beginning of like this could be a million dollar idea or million dollar business what does that look like all

right so let's role play uh my cousin comes to me and says dude forget the passion forget the art Forget the thing I love. I just want to make a million bucks. All right? Which is fine. It's a fine thing to say. If that's where you're at, that's where you're at. Let's go. And they said, what is the – I don't even know what that looks like. I don't know where to start. I don't know what the easiest path to that is. I'll first say, look, there's a million ways you could do this. So that's the first thing to know. There's a lot of different ways to do this. There's no one right answer. And by the way, anybody who's telling you like, here's the answer or here's the easy way, they're probably just selling you some shit that that's their way of getting rich quick. Okay. So let's not do that. You can, let's say you want to build some wealth. You could go get a job and save money over time every year, put it away, invest in an index fund, and it will compound. And there is a get rich slow plan. You'll get rich sometime between your forties and your seventies. If you do it that way, if you save consistently and you invest and things, you know, knock on wood, nothing bad happens. Okay, cool. I was not interested in that. I was interested in a little bit of a faster path. Paul Graham once said, startups are basically compressing 40 years of work experience into four intense years. I think that's a good thing to know and ask yourself, am I willing to do that? Am I willing to have 40 years of lessons learned, 40 years of stress, and 40 years of income come in four years, right? Like that would be like a model of looking at the world of starting a business. All right. So let's say you want to get to a million. The easier way to get to a million is to basically sell equity in a business. So you own a business, you own equity in that business, and that business becomes worth something that you could sell. So let's just do some basic reverse engineering. You can create a business. If you want to sell and get a million dollar check, you're going to sell your business. How much money does your business need to be making to sell for a million bucks? Well, let's just, every business has different multiples that they sell for. Meaning if you have a hundred dollars of profit, I'll pay you five X multiple, meaning I'll pay you $500, five times your current profit. So four or five times multiple is pretty standard. So you want a million bucks, you need to have a business that's producing something like $200,000 to $250,000 a year of income. Okay. How do you get $250,000 of net profit? Well, you're probably going to need to be making something like $500,000 to $800,000 of revenue to do that. Let's take $500,000 just for simple math. So to do $500,000 of revenue, then how many, let's think of a service or a business I could do that would generate that much. And then what you want to do is create a menu of options. So create a set of possibilities to get there so that you don't pick one. Come up with 10 different ways that you can get there. And if you don't know how to come up with 10, you're probably not ready to do it yet. Meaning you don't need to know 10 ways how, but you should know the fundamental skeleton of what a business looks like. So for example, my buddy made $10 million selling a blog that was about soap operas, like daytime, like the young and the restless. A WordPress blog that was spoilers about what was going to happen tomorrow on the young and the restless. He sold for I think $9 or $10 million. He owned the whole thing himself. He had nothing before that. He built the whole thing. It took very little investment capital. Amazing. I would have never even thought that that's a way you could make money. But I listened to podcasts like My First Million or your podcast or whoever. And I start to hear stories. I start to collect these examples. Oh, that's one way to do it. When I met him, I asked him, I said, how did you even think of that, dude? I would have never even thought you could make money by selling a blog like that. He's like, well, actually what I did was I went to websites where people sell businesses. And there's brokerage websites like Quiet Light Bro or Flippa or these different websites you can go to. He's like, I didn't know where to start. I didn't know a bunch of rich people that would have been better if I just had a network of successful people I could go ask. I didn't have that. So he's like, I just went to where people are selling their business. And then I tried to reverse engineer. Wow. He's like, I saw a guy who was doing a blog about soap operas that was selling for like $1 million and he couldn't believe it. He's like, man, a blog about soap operas could do that for $1 million? And so he used, he reverse engineered. He basically looked at businesses that were already selling for a certain amount or already generating a certain amount. And he basically started making a list of what are the options. Made a list of 10, 20 businesses that he found out like that. He would walk around his town or meet people or ask his parents, hey, who do we know that's a successful business person? What do they do? How do they do it? And you go talk to them and you just start to come up with a game plan, right? So I think the successful formula is you want to make a million bucks. Basic math would be, the basic numbers of the napkin math would be, you're selling a business that does $250,000 at a four or five X multiple. To have that much income, you need to be generating maybe $500, $600,000 of revenue. To do that, you might have a hundred clients that are paying you, you know, two grand a month to do SEO services for them or Google ads for them or to optimize their website or to give them leads or whatever, whatever the business is. There's a million plus different types of businesses. How do you pick which one? Well, first go get around people who have done it, start to learn about them. And then again, whichever one interests you, go try it and expect that it's probably not going to be your first one that works. You had a starter business. I had many starter businesses. It's totally okay to have those starter businesses to try to get there, but it is pretty useful to do the math and sort of like understand the mechanics of like, where does the big payday come from? All right. And there's, there's other variants of this, by the way, like in Silicon Valley, people make a billion dollars, not a million dollars. How do they do it? And you know, you can go break down what makes a business worth a billion dollars. Talk to people, read about it and start to reverse engineer what, what actually works. I'm a big fan of cloning, I don't want to figure everything else, everything out from scratch myself. I would rather understand what's worked for other people and then ask myself, do I think that I could do that? Was that a one-off circumstance or are there many examples of people doing that? And if there are many examples of people doing that, how can I go hang out with them, talk to them, see if it's really all that it sounds like and how they approach it, how they start it, and then ask myself, do I want to do that?

You know what the, I love the point about cloning. I call it, um, at least to myself, when I think about it is I hate starting from scratch. Like I, when I see people talk about ideas or like things, people will be like, i saw this person do this maybe i should try this or maybe i should do this and it's like every time you're just switching or you're just doing something randomly it's like you're starting from scratch like there's no there's no model there for you to build on it's just starting from nothing right

um the best way to learn is to learn by doing it is also the slowest and most painful way. So if you limit yourself to only learning everything from scratch, it's like that dude who tried to make a chicken sandwich from scratch. I don't know if you saw this. Like he, like, he like grew the bread, like, like planted the seeds, grew the bread, raised a chicken, got the chicken to be old enough, slaughtered the chicken, you know, raised the tomatoes. He did all of that. And it basically cost him like $2,000 in two years to make a single chicken sandwich. And he did it as like an art project, a statement project of like, wow, how, you know, we don't even think about what it takes to have these things that are in our life every day. But that's what I see some people do, man. They just take the long, hard road of like, I'm going to grow my own chicken sandwich. It's going to take me 10 times as long as it needs and 10 times more painful and expensive than it needed to be. When it's like, dude, you can just go around and look at what's working and ask, can I remix this? There's a great story that this guy had on my podcast, Monish Paprai, says he talks about the two gas stations. And he goes, I forgot how he says it, but it's like the dumbest person in the world is the guy who owns a gas station across the street from a successful gas station. He's like, because the guys across the street, you can see what he's doing. Like watch him. Oh, he walks out when the customers are there and he washes their windshield, know, complimentary to make them feel happy. Oh, he's got better snacks and better signage than I have. Like all you needed to do was copy best practices. That'll get you like 80% of the way. 20% is going to have to be your original flavor, your special mix for this. Like I'll give you an example. What's an easy one? My e-com business. I told you that my friend was selling a bunch of dog ramps. And so I then went over to his house and I was like, hey man, I'm fascinated by this. I would love to learn this. Can I just come shadow you for a day? I just want to hang out, see what it's like to even do this job. And as he was doing it, I just reverse engineered. Okay, what makes something like this successful? So he's solving a pain point. He needed to know how to do Facebook and Google ads. Cool. I don't know how to do that, but it seems learnable. Did he know it up front? No, he didn't. He learned. It took him about six to nine months to get good at this. In e-commerce, what are the key metrics that matter? AOV, your average order value, your margin, you need to have this much margin, your customer acquisition costs, your LTV, right? Okay. What are the acronyms that today mean nothing to me? It's alphabet soup that I just need to, I need to learn. It'll take me a couple hours. I go Google the shit, learn it. And I can start to figure out what the blueprint of this business looks like. And then I can ask myself, do I want to do that? And that's what I did. I picked a different category, but I took the learnings from that and five other friends I talked to like that in order to understand how to build a business like that. And I've done that just over and over and over again, rather than me figuring things out the hard, long way from scratch with no input from anybody else. You

know what?