How YOU Can Build A $3,000,000 Newsletter Business Without ANY Employees! | Sam Parr

If I were to start a newsletter, I definitely could do probably at least 3 million a year, I would think. Which, just by yourself, just means an assistant. You said the first Hustle Clone that you did, you made 60,000 from that. I think it did between 50 and 60 in revenue, and I probably walked away with 40 grand. I called myself a $50,000 millionaire. Like that first 50 grand might as well have been a million dollars. I felt, I remember I was like, should I go to Thailand? Should I bring these girls with me to Thailand? Like 27 grand might as well have been 25 million.

The cool thing about a newsletter is you write it as if it's just me writing to you, not me to millions of people. Just I'm writing to you, that's it. And uh, that built a lot of loyalty. Let's just assume that the person that's listening is a great writer. What is the next step? I know when we, we spoke, you said you have this process of reverse engineering your success. Do you have your phone on you?

I do. All right, you're going to help me do some math. So we spoke yesterday, and you mentioned to me that by the age of 21, you had made this decision that by the time that you were 30, you would have made $20 million. And so for most people, when they're 21, they're just getting out of college, or they're just starting their first full-time job. They have no idea what they want to do, right? So what gave you the certainty at the age of 21 that you wanted to make 20 million by the time you were 30?

Well, I wasn't, I had certainty that I wanted it. I didn't have certainty that I could get it. But I basically like grew up in a middle-class family. My parents were business owners, and their business did well when I was in high school. But for the majority of my life, just a very normal background. And uh, I just didn't want to have to like worry about financial stuff. Like I saw like what it meant to maybe not have a lot, and I thought if I could just remove that from my life, that would be cool, right? And so I just read like a lot of entrepreneurial, entrepreneurial biographies. And I just noticed a pattern of like people who like have done major things in their lives, a lot of times they're not like Mark Zuckerberg, where they do something huge right off the bat when they're 21. But they like have small hits along the way. And I was like, I think I can get a small hit enough to like make that much money by the by the time of 30. And if I do that that way, eventually if I have a family, I could just focus on like emotional and spiritual like stuff for them, and like I focus on being present for them and not have to worry about like financial stuff. Because it kind of freaked me out that um, we don't live like that long, and I'm going to spend 40 or 50 hours a week doing something I hate just to like provide. I, I just didn't like the idea of that.

And so I basically spoke to a bunch of wealthy people, and they, I asked them how much money they spend per year. And one guy said like 50 or 60 or something like 60 grand a month. And I was like, that's so much money. But if I have roughly $20 million, and I only spend 3% of that per year, $20 million would never run out, and it would actually continue to grow. So if I could make that by the age of 30, I could live a very lavish lifestyle. And I don't spend 60,000 a month, by the way. But I was like, you know, that's like a good benchmark to where you can live a really fancy life and not ever run out of money and just only focus on important stuff as opposed to just money. And I just thought that was a really, I mean, I thought it was, it was a dream. So like I didn't, I had a goal, but I had to make a plan. But yeah, that was my goal.

Yeah. You know what's interesting? I was actually having a conversation um, with my mom, and I said to her, I was like, I want to get to the point where I just don't have to think about money. Like that is like a dream, like don't have to think about money. And I think for so many people, I would say 99.9% of people, every single, every single week, every single day, every single month, they're thinking about how am I going to pay the bills, how, you know, like money is always on the mind. And so I'm curious for you, like in your, in your childhood, in kind of your early years, were there experiences where maybe you would even see your parents or people that you grew up around, they were just constantly like worrying or thinking about money?

Yeah, my parents owned a fruit stand, that was their business. And then eventually my mom became a school teacher. And then the fruit stand kind of like grew into one thing and then into another thing. And then when I was like in fourth grade, my father like uh, left to start a new business. And I remember thinking like that's really stressful, like are we going to be able to like eat and, and have that, like are we going to be able to provide and like have clothes? I remember feeling that feeling, and it was kind of traumatizing. My parents also had this like mentality, which they're not wrong for having this mentality that a lot of parents have, which is like it's my way or the highway. I pay the bills, so like that was often the reply that they would have is like, well if I pay for things, you're going to do it my way. And I hated that feeling. I [ __ ] hated it. And so like those two feelings, I was like, I don't want to feel this way. I want control, and I want power, not necessarily like power over anyone else, but I wanted power over myself. And so like I just remember being like seventh or eighth grade where it's like, I want money so no one can tell me what to do. Like I really want that feeling.

Mhm. And I just read like a ton of books. And when you read all these books that I would read about like biographies, basically, you know how they say like you're the average of the five people you spend most, I felt like I was the average of them. And so I started getting used to like succeeding, though I wasn't actually succeeding. I started like getting used to like reading all these success stories, and it kind of just like, you know, maybe there's a way where money doesn't have to like be everything you worry about. And I still think about money all the time, by the way, but like it's not from like a scarcity mindset, which uh, I wanted and then, or which I didn't want. But then when I started my first business, the Hustle Dude, I paid myself $20,000 a year for like the first two and a half years. So I lived in San Francisco, so I was like poor. And then I was poor. I started a business in college, and I was like paying for my own life. I was poor then, and so I just didn't like the idea of being poor. No one does, but I really hated it. And so that's kind of like why I had all these goals.

Yeah, you know, I think um, I was listening to an interview with Hanan Minaj, and he always talks about like the drive shaft, like understanding someone's drive shaft. And I think it's so interesting that for someone like you, obviously you built a business that you sold for over $20 million. Like people that achieve that level of success, from what I've seen, they're usually motivated by two things: it's either extreme desperation or extreme inspiration. And one of the things that you mentioned was like just wanting to have that feeling of control over your life, like hating the feeling that you weren't in control of your life. Is there a certain experience or like a story that you even remember from your childhood where like you really felt that feeling of like, oh, I just hate this, like the angst of that?

Yeah, I think I told you this, but basically when I was like 21, so like between the ages of like, I started like, I went to college on a, on a track and field scholarship, so I was like a pretty good athlete back then. And I like started experimenting with like drugs and alcohol, and I got super into it, and like I loved beer. Beer was like my favorite thing on Earth, and I like kind of fell down the slippery slope to where I like pretty much became a full-blown alcoholic. And I got arrested like two or three times in like a month. And so I had had to spend like uh, collectively like five days in jail, like two, two uh, two days for one thing and then three days for three days and three nights or something like that for this other thing. I remember being in jail in like County Jail, and it was so horrible. I remember getting out of there and thinking, I never want to do anything bad ever again. I don't want to break any rules. I want to follow, I want to follow the exact rules, do everything the right way, because I remember coming home, I have this uh, I had this 85-pound pull, this gorgeous dog. And I remember coming home, and when I got arrested, I didn't like, when you get arrested, like it's hard to call people because I don't know if you do, but I don't know people's phone numbers. And so when I got arrested, they take me to, I'm like [ __ ], I don't know anyone's number. I can't call anyone to go get my dog. And so my [ __ ] dog had to sit there for like uh, two days in the house, and he had water and food, but he like [ __ ] all over the house. When I got home, I was like devastated. I was like, oh my God, I was in this cage, and I failed you. I felt so bad about myself, and I felt like I let down this animal who's, it's my responsibility. And so like pretty much there I was like, I got to get my act together. Like I'm, I'm a loser, uh, I have potential, but I'm being a loser right now. And, and I basically got sober um, and I failed a couple times. I relapsed uh, when I was in San Francisco, and then I did it again. But like getting in trouble was like uh, it was like a really big deal. And then after I got arrested, by the way, I don't know if you know the story, I had cold-emailed the founder of Airbnb when I was in college, and he offered me a job, and I got the job. And back then it was called Airb and Breakfast, it was like early in their, in their company, and they gave me a job. But then I lied about my resume uh, I basically said I didn't have a criminal record, and they found it, and they, I moved out to San Francisco and everything, and I showed up, and they're like, dude, you lied, you're out, we fired you before we even started. And so like getting in trouble in that like three-month period, it was like, it was like uh, the worst, it felt horrible. I felt very, very bad about myself. And from then, I was like, I want power over myself, like big time.

Yeah, you know what I think um, yeah, like it's such a, it's such a, it's a story that resonates. And I think one of the things that I'm curious about is what was the beginning of like that, those tribulations with alcohol? I think that's something that I've seen you mention a lot, like your journey of getting sober, like the effects of alcohol. And it's even interesting you say the thing about wanting to feel in control when you were like a kid, when you were a child, but then what's the one thing that makes you completely out of control?

Yeah, alcohol, drinking alcohol. Yeah, I think that like, well, it kind of stems from some place. I want, I want control because like I was, I was nervous a lot. I was, I was a pretty, I still am, but I was much more of an anxious person. So I'm like, well, if I have money, that's just like one thing less to worry about. But alcohol makes you not worry about stuff as much. And so I got super into it for that reason. I'm like, oh my God, I don't worry right now, like so it was very much a self-medicating thing um, and so when I got into booze, yeah, like, and then part of it was like, I'm scared to like do things. I'm afraid to, to talk to girls. I'm afraid to like not be myself. And for some reason, alcohol makes me feel better. And so it definitely helped, and it was like the greatest feeling ever uh, being drunk. Um, how would you feel? I'm just curious, like when you go back, how would you feel when you were drunk?

Just numb, to be honest, but like, just numb. But like, I mean, there was a period where I was intoxicated every single minute of the day for like a year and a half. And so like, I don't remember, like there's like months where I'm like, I don't really remember too much about what I was doing then um, and so I was like super into it. And I basically moved out to San Francisco, and I relapsed, and I went to a homeless clinic to, to quit drinking um, like it was pretty insane. And like I remember I had like apple uh, like these corded headphones, and I'm pulling up in this uh, like I was just walking, but I didn't have a lot of income because I was running my own business. And so I, and so I qualified for like this like free clinic. And I also was like, dude, I'm a junkie kind of, I'm like a loser. I should be with these people. This is, this who, this is what I am. I need to experience this. And uh, I remember like I had these headphones in. I'm like, what am I doing here, dude? I got like an iPhone, like I had like, I, I'm not, my life was not set up to be this bad. Why am I behaving this way? And so yeah, I got sober, and it was like the, like three or four months after getting sober was like the greatest feeling on Earth. I like, that was when I really felt in control. I'm like, I control my emotions. I control so much uh, stuff. And that was like the greatest change of my life.

Yeah, no, that's amazing. No, I think for, for most people that kind of get addicted to alcohol, they start drinking almost like an obsessive rate um, there's something that you're like trying to escape from, like it's a form of escapism. You say even it's this feeling of being numb. And I guess for you, when you reflect now, given what you've achieved and the fact that you've been sober, do you have clarity on like what was it exactly at that time you were escaping from?

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Just like some weird stuff that happened with like parent issues, of just like getting in trouble and like getting yelled at, parents arguing, things like that, like I just didn't want to like confront it um, and it just felt better to be intoxicated. Yeah, I also think I'm genetically predisposed to, to, to like this stuff uh, but yeah, just escaping like weird traumatic issues when you're like a kid. That's what I've learned it all comes down to is basically is like experiencing something as a kid that could even seem innocent. For example, I hate flying. I don't like flying at all. I'll, I'll drive across the country oftentimes instead of flying. I had to go through years of therapy to remember it was because when we were kids, my brother was playing with me, and he put my arms behind my head, and he dunked my head in the water, just like teasing me. And one time, water got in and like I thought I was drowning, and that stemmed all of my like claustrophobia issues. So like it all comes from like weird stuff when you're a kid uh, I think yeah, that's interesting. It's like a lot of our story and how we behave as adults is like built in our first 10 years. It's all, I fairly believe it's like all from that, from that period, which is kind of scary, right? Yeah, when you have kids, you're like, cuz like, for example, I think I thought booze were cool, and I didn't like my father. One time I saw him take a straw out of a drink. I was like, why are you taking that straw? He goes, men don't drink with straws. And so my whole life I never used a straw. And he was referring to like his Jack and Coke, you know, it was like, or like, you know, like those D straws, like I remember for years, I'm like, I remember seeing you guys when I'm an adult, like why you drinking from a straw? Men don't drink from straws. And people are like, what are you talking about? I'm like, what my dad told me, that, you know what I mean? It all comes, everything comes from when you're a kid.

Yeah, you, you spoke about your dog, Sid, and there was this post you did. You said, Long Live Sid. This dog saved me from being a degenerate. A man's dog in his 20s is special. They see the evolution. I love him so much. I got my life together because of him, got sober because of him. Why do you say that? Why was he so meaningful to you?

So I got this dog because I knew a guy who was a drug dealer, and the drug dealer got arrested, and they were like, hey, can you watch Jake's dog? I was like, yeah, I'll watch him. And they're like, he'll be back in two weeks. And he just didn't get out. And that's how I got this dog. And he was a huge like white pull, like the meanest-looking dog ever. And uh, he didn't get out of jail, so I got him. And so I had him for 15 years, and he, the reason I loved that dog was because typically when you're 20, you don't have the same friends when you're 20 as you do when you're 35, at least my age, like, and you're for a man, you know, men develop later than women. For a man, you're developing in your 20s, like well into your late 20s. And like there's not that many people that are around for the whole evolution. So it felt special to have like a being there who could see that. But also dogs are special, man, because you got to, you got to take care of them. I like having responsibility. Having responsibility makes me feel good, you know what I mean? And so I have a family, and it's like the greatest feeling on Earth. It's the most masculine feeling you could have is to take care of someone or something. And so it just, yeah, I love that. I think that like men should try to have children. You should try to have a family. Like that's cool. Like having someone to like devote yourself to is a really good feeling.

Yeah, you said this dog saved me from being a degenerate. I'm, I'm curious in those kind of like early stages of having, having Sid, like what were some of the changes that you were seeing in yourself?

So I'll give you an example. So I, I was like an okay student, but I didn't really take it that seriously. But I remember there was an accounting Meetup, and at this accounting Meetup, they were going to give away $200 in a raffle, and I needed that $200 to hire a trainer to teach me how to train this dog because I didn't have any money. And I went to this accounting Meetup, and they were like, if you switch your major to like accounting, by the way, like we could, you can come to these all the time. And I was like, [ __ ] yeah, sign me up. So I switch my major to accounting just to like go to these meetups. And I eventually won $100 or $200 at one of these things. But then I liked accounting. And so like, like I would like do these things just for this freaking dog. And like it actually meaningfully changed my life, but that's like one example. But I remember like, I can't get in trouble tonight. I got to go home, you know what I mean? Like just that simple feeling.

Yeah, you know what it's funny because you, you mentioned responsibility. I think it's actually a really big thing for men is like you almost need something larger than yourself to be a good person, for like something like it makes you better because you're there's some, there's someone or something that you're doing it for. It's not just purely selfish.

Yeah, I think that like, so I had that 20-million-dollar goal partially because I was like, I'm going to have a family, and it would feel good. And I didn't have, I wasn't dating anyone then, like it, I was way off, but I felt good to like think, like this is for the share with, with my people. And that's like a really good feeling. I think that a lot of people, particularly in business, when you're like making money just to make more money, that's a really empty feeling. But when you're doing it to give it away, or you're doing it to create jobs or something like that, when you climb up that Maslow's hierarchy of need, it feels really good. Like it's a very good feeling.

Yeah, uh, and yeah, I just enjoy having, I remember when I was 26, one of my employees got pregnant and was going to have a baby, and I was like, feels like I'm having a baby, like what the hell, like how am I going to like, how am I going to make this business work to be able to support this woman and her husband and her child? Like that, that was the feeling. And I was really, really nervous, but it felt amazing. It was like a, it felt awesome to have that pressure. I'm like, I have to make this business work to support this woman and her family, or to like create a workplace where we can like pay salaries. And it was very scary and awesome feeling. I, I really like that. I'm a big fan of um, have you heard the phrase burning the boats?

Yeah, yeah. I love burning the boats. Like basically it's like uh, this Spanish conquistador, he came from, you know, Spain to America, and lights his boats on fire, and he goes, look, boys, we better, you know, take care of business, cuz we don't got no boats, we ain't going home. And like, I love that feeling. I thoroughly like that feeling. I think it was also, I hope I'm getting this right, otherwise my like uh, my like uh, primary school like Latin teachers going to get mad, but like I think there was also a story of um, when they came to like sack Troy, they obviously came on boats, and they turn up on the beach, and there's like this...

Huge wall that they have to scale in order to get into Troy, and so to create the, um, the impression, to create the belief in the minds of the soldiers that they either had to sack the city or die. They burn all the boats. Yeah, I love, we don't have a choice; it's like you just get it done. I love that feeling. I think that we should put ourselves in some more situations like that. I think that that is where greatness kind of comes from, is when you're like your back's up against the wall. That's why like a lot of badass businesses are founded by entrepreneurs or immigrants. It's like when you come from nothing, it's like, I got to make this work. So I love that, that feeling. I'm, I'm a big fan of that.

Yeah, and so it seems like in your story, that feeling of the back against the wall—it's like you come out of jail, you see, um, the effects that it even had on Sid and like the people around you. Now it's not just something that's detrimental to you; it's actually beings, animals, people around you are actually—it's hurting them. And so you start to make this progress from being a degenerate to like actually starting to get your life in order. You mentioned there were moments where you relapsed, and I, I think that's interesting. It's something that I've heard, um, Alex Horsey talk about, is something that I experienced, which is that whenever you make a journey of like change and you go on this path of like, you start at Point A and you're trying to get to Point B, and it's completely different; you start on this path, and every now and then you start looking back to where you were before, like you kind of get tempted with your old life. Yeah, you know, talk to me about those relapses. Like, what was happening there?

Dude, being the, so the lifestyle that I had of like being drunk all the time and like, so basically I lived in, um, this in Nashville at the time, and I lived next across the street from the projects and just chilling on the corner and drinking all day with these guys. It was so fun; like it was so much fun. You know what's that—have you ever seen that YouTube video where kids like, "I just want to do hood rat stuff with my friends?" That's what I did every night, and it was honestly so much fun until you realize you're a [ __ ] loser, you provide no value to anyone, and you feel sick all the time. Like, it's fun until it ain't fun, and it always becomes not fun. And so I remember, uh, like getting my act together a little bit for about four months, and I get out to San Francisco, and immediately I'm in a new place, and I'm super uncomfortable, I'm super awkward, I'm nervous, I'm by myself, I don't have a lot of money, I'm nervous about paying rent. I just moved out there to join—I basically left school and went, moved to San Francisco to like join Airbnb, and that didn't work out, and I'm like, "I don't know what the [ __ ] I'm going to do," and I'm trying to fit in. And so it all came down from not being confident in my own like values and things like that. And so I started drinking again to like escape, but also to fit in. And then about a year later, I, um, really like kicked it for good, and it was, and and it worked out. Yeah, it's, it's interesting, even with the context that you provided earlier; it's like as soon as you start to feel out of control, it's like reach for the alcohol; it's like that stabilizing kind of, yeah. And it's rooted down into like—and so I think I told you, like I'm obsessed with like reverse engineering things. So like, um, I'm, I'm pretty into like discipline and like, um, now I am into discipline and like having a routine and things like that, because—and then having a plan and like executing towards a plan, because when you, when you're someone like me or—and I would think you—I told you this analogy, but it kind of feels like when you're like this, like there's a bunch of people out there who are these like high-energy people, and they're like a car, and someone's sitting in the car and like pressing the gas as fast as they they can, but your back wheels are lifted up, and it's like you have to make sure you point that car in the right direction, because if you point in the wrong direction, it could be like destruction; you're going to get to where you, you're going to go to a place you don't really want to go, and you're going to get there fast, or you're going to like get in a wreck along the way. Like picking that right, uh, picking the right lanes to stay within is really important. And so for people like me, like if I have like a plan and like a clear destination—that's where you're going—uh, I feel very happy, and I feel unstoppable. But as soon as like that plan goes away or, uh, uh, you know, things like that, like then it's like, "Oh, let's go this way; let's," you know what I mean? And so it's important—that's why I love like reverse engineering and having a very specific plan, so why I always have like five- and ten-year goals and things like that, because without it, I just kind of can go off the rails.

Yeah, and I think to your point, it's like we have this—and I think people relate—you have this energy, you have this like fire, and if it's not directed in the right way, it can be completely detrimental, but if it is directed in the right way, it can achieve incredible outcomes, with which we saw with your media company. And by the way, that's why I love UFC—UFC fighters, they're freaks, right? They're animals; like they're these men who want to fight to the death in their underwear in front of millions of people, and like there's a funny Dana White quote where they're like, "Hey, this one guy got arrested for like getting a dii—getting in a fight or something," and he's like, "Yeah," and they like, "Well, are you angry?" He's like, "I'm angry, but these guys are animals; what do you expect?" Like, so my goal is to point him in the right direction and give him some—and put point that car the right way. But when you're crazy enough to do that, you're going to do other crazy things, and I think that for anyone who's like wants to achieve anything interesting, they probably have a little devil in them, you know what I'm saying? Yeah, and it's just about keeping it in bounds.

You know, one of the things you mentioned, even with the relapses, is that after about a year and a half, you actually kicked it for good. I'm curious, like what was the difference? Like, what was, what made that time different? Whatever happened within that period of time? Okay, one second. This episode is sponsored by our friends at Cloak. Now, one of the most annoying, irritating things is when you get these spam calls on your phone; an unknown number pops up, you answer it thinking it may be something actually important, and it turns out it's just a spam call. Well, I was shocked to find out that if you're getting these spam calls, there is a high probability that your phone number and personal information is on the dark web or on other data broker websites. And the scary part is that by having your phone number or email address, spammers can stalk you, hack into your account, and even get access to your home address, banking information, or social security number. And so when I found this out, I had to make sure I was protected online, and the first thing I did was go to cloak.com and use their free security scan. And it's so simple to use; you type in your phone number, which they keep secure, by the way, they do not share it, and Cloak will check over 120 different data broker websites to see if your information is there, and if they find anything, they can help you remove it and stay protected online going forward. Here's what you're going to do: this is step one. I'm going to link Cloak's free security scan in the description; click on that, check if you are protected; it only takes 30 seconds. They keep all of your information secure and private, and if you want to try their paid plan, use the promo code Callum at checkout to get 20% off a Cloak subscription. That's Callum, C-A-L-U-M, at checkout to get 20% off Cloak. Without further ado, let's get back to the show.

Yeah, I went to this clinic; it was called the San Francisco South of Market Mental, Mental Clinic, I guess, uh, and it was basically homeless people, and I met this doctor named Joselyn Porz, and Joselyn was like, "You know, you, you don't seem like a lot of the other people that are here; you're pretty articulate; you don't seem like that mentally ill; like what's going on?" And I kind of told her my story, and she really believed in me. And so she was my doctor for like eight or nine years. And so once I made above $155,000 a year or something like that, or I had income, I no longer qualified for Obamacare, so I just started paying her out of pocket. And so she actually saw me go from like, um, whatever I was like a loser to like meeting my girlfriend who became my wife, starting a business, selling that business for many tens of millions of dollars, and she's like, "It was so awesome to like impress her." I was like, "I want to impress you; like you believe in me; I'm going to, I'm going to, I'm going to be the best story that you've like—I want to be like your win story." And so having her like on my side like really helped me like, because I wanted to show off to her and like make her proud, things like that.

Yeah, someone that believes in you—it's interesting in everyone's story; I feel like that's a success, even if it's just one person; there's always that one person that believed in them; it's so critical. Yeah, like I wanted to go back to her next month; I mean, like, "Check this out; like look what I'm doing now," you know what I mean? It was, was very exciting, and and uh, progress is pretty like addicting, like to like progress on something; like it feels pretty awesome. Yeah, like whether it's weight loss or whatever, like it feels awesome to like get results. Yeah, you know, we're going to get into the newsletter stuff and how you built like a multi-million dollar newsletter and the blueprint behind it, but before we do, talk to me about some of your early businesses. I actually even have a list of them. What do you have—you, you've got the, you got a hot dog stand, you had an online business selling whiskey, yeah, matching app. So yeah, so I, I had a hot dog stand; it was called Southern Sam's Wiener, as big as a baby's arm. I met a guy who had a hot dog stand in storage, and he wasn't using it, and at the time I had $500, and I was like, "I bet you I can get a day's worth of supplies for a hot dog cart," and that's—so I went and got my like food license or whatever, and he let me rent his cart, and I would pay him at the end of the month, so he would gave me a month for free basically so I could start this business, and it was awesome, it was badass, it was so much fun. I, and I did it because that was like one of the jobs that you could have like, and you could still drink during the day, because I would work from like 11:00 to 3:00; I would go to class from like 3:00 to 8:00, and then work from like 9:00 to like 3:00 in the morning, you know, the bar scene, and uh, I would kill it, man. Some days I would walk home with like a grand in like $1 bills, and me and my, like I would hire this young woman to work with me; we called it being Hood Rich; we just had, we just had a, a stack of cash, just like a fat stack, and it felt awesome. And then other days we'd make like 80 bucks, but it was like 110 degrees in Nashville in the summertime; it sucked; it was so bad. And I got curious about like the internet because I was like, "I don't want to work outside all the time; this is really hard." And so I started an online website that sold a very special type of whiskey that you could only buy in a handful of stores in Nashville, but like people all over the world wanted it. And so I started selling this thing, and I'd be in finance class, and I'd hear PayPal go kaching, kaching, kaching. I'm like, "Dude, I just made $500; I made $1,000," and I start thinking, I'm like, "By the way, do I need like a [ __ ] liquor license to be doing this? Like, what am I doing?" And so I go to the, uh, the lawyer, like they would—a lawyer would come to school, uh, and like the entrepreneurship like clinic, and you could ask him questions, and I told him what I was doing; he's like, "Yeah, you're breaking the law, dude; you can't do this." And I was like, "Well, [ __ ]." Uh, so I bailed on all that, and I moved to San Francisco, and when I got fired from Airbnb, I happened to be staying on an Airbnb at a guy's house who had an idea for a roommate matching app, and it was basically like Tinder but for roommates, which was stupid because it should have just been Tinder for Tinder, like that would have been a way bigger business; like it should have been—I dated a girl who I met on the app; like I started—I was like, "I don't even need a roommate right now; I used the app to find my roommates," and I was like, "[ __ ] I want to meet people; like what's going on?" And uh, we sold it for not a lot of money, um, but enough. And then after that, I started, uh, a conference company, yeah, and the conference company did all right, and then I started The Hustle after that, which eventually was, was life-changing.

Yeah, you know, it's actually funny watching you even talk about it because I can see like your emotion; like you still get so amped about it; it's like so fun to you. It's kind of like—like listening to your stories; it's like it's the degenerate guide to business. And yeah, it's, it's the same—it's all from the same place; like it's fun to do bad stuff sometimes, and like when you're making money online, as long as you're doing it in an ethical way and supplying customers, and it, it sometimes it feels like what you're doing is illegal; you're like—have you ever made money on the internet and like seeing like a got like the kaching; you're like, "Oh my God, this is [ __ ] awesome; like I got my first sale; it's like the greatest feeling on Earth; you're like, 'How's this legal? This is so cool!'" It like kind of is that same energy. So yeah, it felt awesome. Yeah, no, I love it; I love it. Okay, so it's interesting, actually, the story of The Hustle—of course, you go on to sell it for rumored $27 million, uh, to HubSpot—but it started as a conference, so, so talk to me about that; like what was kind of the early origin of The Hustle?

Yeah, I, um, sold the app; I worked at the company that bought it for one year and one day, and then I started this conference, and the idea was like, "I'm going to do this conference called Hustle Con; it was a horrible name," uh, it was like TED Talk for entrepreneurs; yeah, it was like a horrible name, but I thought it was funny, and I was like, "I'm going to meet someone at the event hopefully, and I'll partner with them, and we'll start a business together, but this is a cool way to kill time." And I did the first event; I think I had the idea, and then six months—six weeks later—the first event happened, and it, and it made like $60,000. And then I was like, "That was amazing; I just made 60 grand in six weeks; that was awesome." So I said, "Let's do it again." And so I spent six weeks or eight weeks or something driving around the country on my motorcycle just celebrating, and I did it again. I think the next time it made like 150 or 180; I don't remember, something like that, over $100,000, and I was like, "That was amazing; let's do it again." But then I started thinking, I'm like, "Man, if it rains, like my business is like out of business; like if something bad happens, like I'm doing all this work for one day; like that's not the savviest business." And in order to make people come to the conference, I created this newsletter where I would write stories about, uh, were about each speaker, and I made them look really cool, and I got like 10,000 people to sign up to that newsletter, and I was like, "You know, maybe this newsletter thing is kind of interesting." And I'd read the biography of Ted Turner; he was a, um, he owned CNN; he founded CNN; he was from the South; he was from Atlanta, and he was kind of like me; he was kind of crazy, uh, like a Southern guy; was—I identified with him, and I was like, "If this [ __ ] guy can do it, I could do it." And so I had this idea of like, "If we create a daily email—if you do the math—the math is such that if I can charge $50 per 1,000 cents to my email, which is was roughly the going rate, and I can get a million people to subscribe, and if I send them an email every single day of the month, that would be like, uh, like $1.5 million a month. And and if I, I'm pretty good at writing; Tech is like a pretty big sector; I bet you I can get a million people to subscribe to this newsletter and build an $18 million business." And then I was like, "But—and if I get 5 million people, you know, I could, I could get close to $100 million; I bet you I could do this." And so that was like the concept early on was, uh, that we're going to create a daily newsletter that tells you everything you need to know about business and Tech, and we'll have some ads in there, and we only need like two or three writers to, to do it. And so it's going to be like a really, really profitable thing, and that was the original premise, and I showed this to a bunch of people, including like—I cold-emailed like CEOs of like billion-dollar huge media companies, and they were like, "This is silly; this will never work." And uh, I sold the company the year I sold; we were probably going to be in the $20 million in revenue range, uh, so I sold before I was able to get to 100 million, which was my goal, but some of my great friends, like Austin from Morning Brew, um, they're around $100 million now, so like my premise, my theory was, was on point, which I'm very proud about, but I sold, uh, before we actually got there.

Yeah, you know, I, I quipped earlier; I said it's almost like the degenerate guide to business, like listening to you. And it's interesting because you have—there's like zero fear; like when I listen to you recount the story, you'll mention cold-emailing certain CEOs or when you started Hustle Con, um, starting this newsletter to promote it, and I'm just thinking to like the average or like the normal person, even someone that's listening, even me, if I was listening to that, I would be like—if I wanted to do a conference and I was like, at the time, kind of like I wasn't in a great position—you would have so much procrastination, so much fear, like, "No one's going to come, or how am I going to get any of these G-dudes?" But what's the alternative? You like go in a cubicle doing [ __ ] that you hate until you die? I'm afraid of that; like when people do that, I'm like, "Aren't you fearful? Like, aren't you fearful of spending your time, your life, your one life; aren't you nervous about spending your time in a way that you don't want to spend?" That's what I'm fearful of. So, and what's the downside? You look silly? I mean, I don't know; like that's not that big a deal. And, and and dude, even if you fail, you look pretty cool; like if you do something like spectacular and you put your effort into it, like that's the difference between America and England; that's one of the—when we were joking—is like in America, if you try really hard and you fail, you're, you're still, like in many cases, you, you can love it; you're like, "That's sick; you, you, you swung; that's great." So I kind of like, in the back of my head, I thought that I also always drisk things, so like I get crazy about it; like I, I remember I had $1,000 that I had in a bank account, and I'm like, "Worst-case scenario, I'm, I'm going to move to in my mom's house, and I got $1,000; I can get my plane ticket home, so I'm good." So everything plus that is upside. Yeah, uh, that's kind of was the attitude.

Yeah, I actually love that; it's like in the beginning, almost set up that it's like the ultimate like fail-safe. Yeah, I always have those, so I, to this day, I have a certain bank account where it's like, "Everything goes to [ __ ]; we're good as long as this is good; we're good." Yeah, I believe in like protecting the downside and drisking things because that makes it way easier emotionally. Yeah, you know what—when you, um—and it also means you can start, you can take more risks, like 'cause now you're like, "Oh, okay, like it's not going to go to complete [ __ ], and now I can kind of, I can really go for it," and the fear should be, uh, "If I don't take this risk now while I'm young and have few responsibilities, if I don't have a sense of urgency, that window is going to pass." So like the fear of that—what you were saying—of like sitting on your ass, it should be the other way around; it's like, "If I don't get to work now, it's never going to work because I'm always going to be too afraid to do it." And so yeah, that's like, that's what I think I, I have, I have, I have a homemade tattoo on my feet that says "Act Now!" Like, I'm like homemade tattoo, yeah, with like a—you use like a sewing needle. Yeah, it's called a stick-and-poke; it's super ghetto; it's like pretty lame; like it's very dangerous; it's a very dumb thing to do, but I did it when I was 21, uh, and and I believe in like action, uh, big time.

Yeah, you know what, before, before you start Hustle Con, you sell this, uh, roommate matching app; you work at that company—selling it is like even glamorizing it—I think I made like 30 grand, like that's how much I made. You, you work at the company that you sold it to for 13 months—I'm curious—someone—no, 12 months and one day—I'm curious for someone with your personality, like what was those—they should have fired me; I shouldn't have even worked there—is that what you're going to ask? What they should—they should have fired me. No, it was—I was horrible. Did that create—almost—that created that feeling of like, "Okay, I'm just going to go for it again the second I get out of this; I'm going for it again." Yeah, yeah, yeah, yeah. And it wasn't like I was a bad employee because I wanted to be a bad—like I wanted to contribute; I just didn't have a lot of skills or anything, uh, and I just didn't—I hadn't had a job before; I didn't know how to like interact with people, uh, so I wanted to do it, but yeah, it was just like a—I knew—I'm like—I basically like read and studied for like a year and like learned and networked, and I was like, "This is my apprentice—this is like an apprenticeship for me, so I'm gonna take advantage of it," and then on that one day, I'm out.

When you—so the first—you said the first Hustle Con that you did, you made $60,000 from that, I think.

It did between 50 and 60 in revenue, and I probably walked away with 40 grand. Yeah, was that crazy to you? Yeah, it was awesome. That's like, like $1,000 a day you make in profit. Yeah, it was awesome. What was the feeling like you deliver the [ __ ]? Like, what's the feeling? I called myself a $50,000 millionaire. Like that first 50 grand might as well been a million dollars. I felt—I remember I was like, should I go to Thailand? Should I bring these girls with me to Thailand? Like, like, like 27 grand might as well have been 25 million. Yeah, it felt awesome. Yeah.

How quickly do you have the feeling I'm going to do the next one? Um, uh, October 1st. Uh, so I did the first one in July 1. On October 1st, when I got back from my trip, I said, "Let's get to work." Yeah, so uh, just a few months. Um, and then I was ruminating on the idea of um, turning it into a media company during that period, and then I launched the media company in April. Uh, it was April 19th of 2016, it's when I launched the media company. Yeah.

I'm curious for you, like when you reflect back on it, when you did that first one, why do you think the speakers that you had came? Because I was up-and-coming. Like, I, I wasn't—I had good energy. Like, I, I it was like clearly like I had the energy of like, "I think he's going to go somewhere. I don't know where or how far, but like he'll do something." Because I was very good at, at making it exciting for them. Like, "I'm doing this thing; it's going to be awesome. I've got these other 10 people as speakers who are also interested." Oftentimes I didn't, though. I would—I said that line to all 10 of them, uh, and that kind of helped each one say yes. Uh, but I had this like energy where I was like pretty positive on the phone with them, and I was like, "I'm gonna, I'm gonna make you look really cool. It's, it's a no-brainer for you to show up, uh, because I'm gonna make you look awesome. I'm gonna make it so you're just going to walk out your door. I'll have a car waiting for you. You're just going to show up. You're in San Francisco; you're going to do your thing, and you can leave right away, and I'll promote your company, and you're going to look great. I'm going to make you look so good. I'm going to work on your talk with you. This is like a no-brainer. Uh, it's going to be so much fun." Like I had this type of energy, uh, and like it was easy to say yes.

I guess you know what's interesting. I was, um, I was watching *Owning Manhattan*. It's, um, the show on Netflix. Ryan—Ryan's—yeah—um, real estate agent sold billions of dollars of real estate, really successful, came to New York City in the beginning and wanted to be like an actor or something, was like a hand model, completely broke. Um, ends up selling—he was a hand—yeah—like he used—that's how he used to make money like when he first got to New York. God bless him. Um, apparently, I guess he has good hands, whatever. But um, he says that—he says this thing; he goes, "Sales is the transference of enthusiasm." Yeah, I totally believe that. Yeah, I 100% believe that. Yeah, that and like I use that with copywriting, but yeah, it's 100% the idea of like getting my energy and my thoughts in my brain into yours and like infecting you with that. Yeah, I'm a big fan of that. Yeah, and you know, I think it's so good because I think a lot of people listening that want to start businesses, but there's something holding them back. They don't see the logical path of how they can get from where they are to where they want to be, and you're missing out the piece which is just, "What about the energy, enthusiasm?" Like that's how you're going to get the speaker; that's how you're going to get the subscriber, the, the reader, is the enthusiasm piece. Yeah, I mean that's like—it's very—that's a very big deal because like anytime you're starting anything, but even if you're not starting something, even if you're trying to convince someone to like be your friend, to date you, to donate to your charity, like we're all selling some [ __ ] right? We all trying to convince someone of something, and like usually enthusiasm and energy is like one of the easiest ways to get people to like buy into you because you're like, "Oh, this person's like—I want to be part of that. That feels awesome." It feels really nice to be led by a confident person, and so if you like act confident, even if you're just pretending, like people like getting behind you. Yeah, that's a really good line. It's really nice to be led by a confident person; feels good, right? Even like really—even like the leaders of the world, like if they have an employee who like, like seems like they know what they're doing, it's like, "All right, I'll trust you. You show me the way." Like that, like—so it's like everyone likes to be led, not just like followers. Everyone likes to be led in things where they're not an expert in, and so, uh, you know, I learned that in—with—by the way—in dog training, like with the dog, like uh, it's called, um, um, being calm assertive, uh, like, like a confident person. People love—like dogs want to be led; the same—same are with humans. Like it's fun to—they—it's fun to follow sometimes and have to think.

Okay, so you—so you build, uh, you start with Hustle Con—first event, 60,000; second event, 150,000. In the act of like promoting Hustle Con, you've also built this newsletter where you're promoting the speakers that gets you, yeah, 10,000 subscribers, and you could Google it, like SAR Hustle Con, um, first one or something like that, and I show all the emails that I sent. Uh, there's like a blog post where I've shared all of them, but yeah, I started that—that's when I started the newsletter. Yeah, that's awesome. So even when we hear the narrative, it feels like it was just going from like one success to the other, and I know from even doing my business for the last 18 months, it is not that—there are really tough—if you're like—your growth chart can look like this, but if you zoom in, it's like that—you know—it's like lots of ups and downs, and like it looks nice and smooth, but there's all these times when it's down, and the time that it's down that could be like six months. Do you know what I mean? In those six months, that's uh, uh, 180 days—that is miserable. That's miserable; it sucks. So, no, it sucked all the time. Um, it sucks most of the time, but yeah, it worked, but it sucks most of the time, and there's certain moments that stand out to you of like, it just sucked a little bit more than all the other ones.

Yeah, dude, the first—first of all, I wanted to quit all the time. Like I'm happy that my girlfriend, who now my wife, was with me. I was like laying on the floor all the time. I'm like, "I can't [ __ ] do this; this sucks. I'm out. If someone wants to buy the company, I'll sell it to them for anything. I can't stand this." Um, the first week that I started the company, so the idea of the hustle was a daily newsletter, and it was news and business that you needed to know in order to get customers. I started blogging; I would blog like crazy. I would blog so much that I—in order to make people believe that it wasn't just me blogging, I had like fake authors, and like I had one author that was a woman, and I would write like a perspective from a woman all the time, and it was just me. Like I did this all the time, but one of these um, blog posts that I wrote, I met this guy who was making $60,000 a month on Kindle, and what he would do is he would find really top-selling pickup artist books and kind of like plagiarize them. I thought that was really sleazy, but I thought that was interesting, and so I wrote an article explaining how he did it, and then the next week I thought it would be funny to, to kind of like stick it into Amazon's face. I found a romance novel—romance has a lot of high liquidity, lots of buyers and lots of sellers. I found a bestselling romance no—novel, and we plagiarized it, and we put a d title on it and a new picture, and we posted it, and we got like 50 friends to quote buy it, and we just refunded them, and it like started going up the charts, and people actually started buying it, and the book publisher who we—the book that we plagiarized was owned by the largest romance novel, uh, publisher in the world, which I didn't—I didn't know that, and they called me and they're like, "You, you, you just broke the law, and we're absolutely suing you," and I was like, "[ __ ]"—my second day of business, like—and I wrote a post saying like, "I'm about to blow $400,000 on my media company," because that's how much money I'd saved, and "I'm going to build this huge media company," and I looked like a total douche, and I'm like, "These guys are going to take all my money that I have. This business that I wanted to start and have dreams for is it ended on week two," and then they email me the next day and they're like, "Look, it's not a big deal. Just write a blog post saying that you apologize, and we're going to forget all about it," but like I sweated for like 24 hours. I was like, "We're done; we're done. Like I can't afford a lawyer," um, and so yeah, that like right off the gate it was hard, um, and then like I had so many issues with hiring—hiring people is—being—leading people is quite—Chen—leading people's, uh, I think kind of easy; managing them is, is hard. So there was all types of, you know, when I started the business I was 24, 25, and so I didn't exactly know what I stood for, so I kind of hired all different types of people when it's best to hire just like people who are aligned with whatever you're trying to do, and I hired all types of people, and it—I made a lot of hiring mistakes. Yeah.

You know what? Those—and I, I resonated with it so deeply, like doing what I'm doing at the moment. There are certain nights where I'll like look at the ceiling and you're like, "How am I going to get out of this situation?" Like it's not immediately obvious to you what the next step is, and particularly if you're the type of—you're working or the type of—I'm work—I'm work in where you have to like create—you're on the treadmill. It's like, "I got to create. Like I, I have a deadline; I have to do something." In my case, it was six days a week, and so yeah, it's very stressful. Yeah, and, and even the thing you spoke about, like leading with confidence, one of the most difficult things to do, especially when you have employees, is like you have to wake up the next day and be like, "Here's the plan," and seem confident. In your mind, you're like, "I have no idea what we're going to do." Yeah, and I feel great with that now. I'm very, um, comfortable saying, "I don't—I'm not sure," but I wasn't comfortable with that then, uh, and so I—yeah, you just got to—you just lie basically, and you're like, "It's going to be great; it's going to work out. I think," uh, but yeah, it's very stressful. That's a very hard thing to do.

Those nights when you would be with your girlfriend, now your wife, Sarah, and you're lying on the floor, you're looking up at the ceiling, and you, you have that feeling of like, "I want to quit. Like I don't know what I'm going to do next," like what keeps you going in those moments? Like take me back, because I put myself in a situation that I couldn't bail. Like I had—like I—I would always hire people before I could kind of entirely afford them. So like I would hire people when I'm like, "If this person doesn't help me—like if I don't make more revenue off this person in 3 months, I don't—I'm out of money," and so I, I would do that a lot—lot, and that—and so it kind of was like, "Dude, I have to make this work, otherwise like these—" Like I think after one year, I think we had seven employees, and I remember thinking like, "I—this has to work, otherwise I got to lay them off," and so I—like those types of situations—I, I hate them, and I like them at the same time. Um, I also had all my eggs in one basket, so I kind of screwed myself, I think. In the first year, business we did 300,000; the second year we did 2.2; third, 5.5 million; 5.5 million. Year four was I think around 12, and then going—we sold—going into year five, I think we were going to do 18. Um, and throughout that whole period we had money—I always had at least $2 million in the business bank account. I paid myself $440,000, uh, like or $20,000 and like $40,000 and then like another 40,000, and then last year I paid myself a lot of money, but I like—was—I felt broke the whole time, which was insane. I shouldn't have done that, and so I felt desperate like a lot while running the business, and I'm thankful that I married a woman who had a great job, and she was kind of my Sugar Mama, but like I was—I legitimately felt broke while I was running the business.

Yeah, you know what? We're going to get into the blueprint of how you did it, but before, before we do, have you reflected on like what that was? Because I think it's, it's interesting, right? Like sometimes as humans, things—and we even spoke about it before—things that we experience as child—as children, it's like you're almost like comfortable—it's weird to say it like this, but you're almost comfortable being broke. Like that's the thing that you know. So even when you have—you're making like a ton of money, it's still like—actually in your personal account, it's broke. Like have you reflected on like why was it that you had millions of dollars in your, in your business savings? Yeah, and I treated the business like its own entity, even though I owned most—all of it. I didn't—I was like, "That's not my money; that belongs to this business, and I'm the steward of the capital, and I like—I might have the keys to it, but it—it ain't mine," and so that was—that's a good attitude, but pay myself more. But sorry, what were you saying? Why, why was it that you think that you did that—paid myself little? Yeah, because I had low confidence, and I was like, um, "I'm not worthy of taking a lot of money. These people should have way more. Um, my time should be free." Like I thought that was cool, and I also was like, yeah, that's how it should be. Like I'm a nobody. Um, and that's how a lot of people are with business where they're like, "I pay myself last." I think the owner should pay themselves first a lot of times, um, not all the time, but a lot of times, but I think it was just rooted in—I'm uncomfortable taking—taking this.

Yeah, you know, I think that's so relatable. I think there's so many people that are listening that you can have all of the accomplishments, almost all of the evidence in the world that you are someone, but deep down you still feel like you're nobody. Yeah, and the—I, I don't struggle with that as much anymore because when I did Hustle Con, I would basically—like we had—we did it from 2014 up until close to COVID, so 19 or 20, and we would have the founders of all these amazing startups, and they were like billionaires and stuff, and if they had to speak at let's say 1, I would be like, "You gotta be here at 10:00 a.m." They're like, "Why?" I'm like, "You got to do sound check," and that was a total lie. There is no sound check at a conference. Like the mic works every time. Like I, I just take it off this person and put on that person. Like it works, but I told them that so we all would get to hang out in the green room together, and so I would have like the founder of WeWork and like the founder of like Away Travel—that suitcase company—and I would just get to listen to them talk to one another, and I would throw out a question there every once in a while, and I would get to hear them like complain, and I would get to hear—I would kind of do like what you're doing to me where I would ask them questions, and I would get them to like dive deep a little bit, and basically my takeaway was that there were stories like where someone was like a billionaire, and he's like, "I'm afraid to fire this person because this—the con—this person's very Alpha, and the confrontation scares me," and I'm like, "But you're a billionaire. Why are you afraid?" He's like, "What do you mean? Like I, I don't get it." You shouldn't be afraid. He's like, "Dude, I'm afraid about everything all the time," or I would see someone, uh, who was just in the New York Times for like a $200 million funding announcement, and they're with me two weeks later and they're like, "I don't know how I'm going to make this work," and I found that to be very invigorating—that the people that I looked up to were like basically the same ballpark as I am in some cases in terms of IQ. Like I could keep up with them in some ways, uh, but they still like were kind of a [ __ ] [ __ ] like I am, like—and that was very invigorating. Yeah, but it's at the end of the day—we're, we're all human. Like no one—no one escapes that—like anxieties, insecurities, fear of failure, scarcity mindset—everyone—everyone has. Yeah, and it's cool to like meet some of the people you look up to and hear that many of them have that same thing. It's a very—that's a very good feeling. Yeah, 'cause they're just like you. Yeah, it feels great.

What did you learn about how to overcome it? You just do it anyway. I mean, it's just—it's, it's a very relieving feeling to know that none of us really know what we're doing, and so if I just act more confident and I have a plan that I've thought through, even if that plan screws up, like that's—it's pretty—it's a worthy cause to go after it, and as I can lead people to—I can lead people down that path if I'm a—if I act confident about it, and I'm honest about it the whole time. I'm like, "I think this is going to work; I think this is going to work. If we do this, then this is going to happen; then this is going to happen. That's the plan. It hasn't been done yet; it hasn't been done before, but I think we're going to do it." So I try to be honest about it, but like, yeah, you just can—if, if you're confident and enthusiastic, people will follow.

Okay, so you—so you build the hustle, um, to this point, you now have huge—of viewership—what—or readership I should say. I think—I think when we sold, we had roughly two million people a day. Two million people—that's crazy. Yeah. Was there—what was the point where you felt—and we even mentioned it in the beginning, right? Like you wanted to have this feeling when you were a kid of, "I don't have to worry about money anymore." When—when was the feeling that you genuinely 100% just felt like, "I've made it"? When I saw—I felt like that—it took about a year till I get used to it, but basically my plan was if I can—if I can—so there's a lot of rumors for what we sold about—sold for. Um, for most every rumor I've seen, it was—it was a bit more, um, than than those rumors. Um, and when we sold, like I remember thinking like it definitely made me happier, like to have that like fortress of—so like that fortress that like, "You can't [ __ ] with me right now. Like I'm good." Like that made me feel good, but then like I'm 35 now. I think I sold when I was 31, something like that. Um, like you—there's always levels though. So now it's like, "I need to get to 500," you know what I mean? Like there's always like CR levels, and that sounds like ridiculous, but it's no different than any sport where like you become elite and you do something amazing, you're like, "But I could do it even better." So there's always levels. So I definitely think about it all the time. Uh, money is not my motivating factor anymore, but it is fun to compete with myself and other people on that game, but that's not the number one motivating thing, but I felt like six months after I sold, I felt like—like I—I could breathe. I was like, "Oh my God, mission accomplished!" Like that was a very proud feeling. I—like I could breathe. That is powerful.

Okay, I'm, I'm curious actually, when you sell a company, is the money just in like an account? Like you could search it up, and it's just like a number on the screen? Basically, so I'll walk you through. So they emailed me, and uh, September, I think they emailed me in September, and they said, uh, "Hey, this company's cool; the hustle is cool. Like do you guys want to talk about partnership?" And the person who emailed me, his name is James Gilbert; he was from like corporate development, and I had had people reach out to me and email me about buying us, and they kind of like, uh, like I was—I've been like dragged through a process before, and they weren't that serious, and so I was kind of fed up with it, and so I just said, "Hey, James, it looks like you work in corporate development, um, do you want to buy the hustle? Is that why you're emailing me? Yes or no, uh, because partnership is like a very vague term, so just tell me, are you trying to buy us? If yes, let me know, and I could—and I'll come with that in that mindset," and he was like, "Yes, we want to buy you." That's all he said. I said, "Great, here's a Google doc that I just made, and I'm going to list out all of the reasons why you should not buy me. If any of those reasons scare you away, just—it's all good; we'll end it here, but if you're still interested, let me know," and I listed like anything that would be potentially bad about my company, like uh, "A few months ago we missed on our revenue target or something like that." I don't know; it wasn't that big of a deal because in due diligence they find all this anyway, so I was like, "Let's just get it out the way," and he was like, "No, no, I'm still interested. Let's talk," and so we signed a term sheet, I think on October 1st, and it was a 90-day closing period, and so for the amount—I, I sold for, uh, we'll say mid-tens of millions of dollars—they take it as serious as a billion-dollar multi-billion-dollar company, and what that means is basically that they have to do all this due diligence—like a crazy amount. So like if I used Fiverr or some type of freelancing marketplace website and I just paid some guy $10 to make a logo, they need to know who that person was, and if I made them sign an NDA and like the receipt for it—like it's crazy. The—now the problem with this is that at a small company like mine, you don't really have like a full—I have like a full-time HR person and like one accountant, and it was the same person. Uh, like it's really [ __ ] hard to get all these files because you can't tell anyone at the company what you're doing. Yeah, partially because uh, that's insider information—so a publicly traded company—my company—so you can't talk about that with anyone. It's like you can go to jail if someone like—like if I bought and sold the stock based off that information, you—you can get—you get in—

Big trouble. And so it was so hard. And then the deal went through on February 4th or 2nd, I think. And a week before it went through, I went to Chase. I just walked off the street to a Chase, and I was like, "Hey, uh, I'm going to be getting a deposit next week, and it's going to be kind of big. Do I need to like warn you?" And they're like, "What do you mean?" I was like, "I don't know, like I just thought I should give you a heads up, like I'm not sure how this works." And I was just literally at like the, the glass, yeah. And they're like, "Hey, why don't you come over and talk to this guy over here?" And I talked to him. Like, "Hey, I'm gonna be getting an eight-figure deposit like on Monday. Like, do I need to like show you my ID or something?" I know, I was like, "I don't even know what to do." And uh, they're like, "No, you're good. Just accept the money." And then uh, on Tuesday or whenever the deal happened, they just, "Why are you the cash?" And it's in your checking account.

I had previously used this thing called Personal Capital. It's like, you know, Mint, you know, like yeah, yeah, Mint, like a net worth tracker, yeah. And uh, I put like $20 million into a fake, like manual account, like six months prior, yeah. Because it's your net worth, a lot of times is just like this number on the computer screen. And so I was like, "Let me just feel what it feels like to have like a $25 million net worth," you know what I mean? And I kind of got used to it, like over those six months, just like seeing that fake number on there. But um, yeah, they just long story short, they just uh, they just wired it to you, just sitting there in in an account, yeah. You remember that feeling when you just first see the number? Yeah, it's it's it's great. I mean, they say money doesn't make you happy, um, makes you happier. I don't know if it makes you happy; it makes you happier; it makes you happier knowing that like if you get sick, like you're okay. I mean, yeah, it made me happy; it made me happier for a very long time, yeah. You know, I want to I want to get into how to how the people that are listening can do it. And and I think the thing that's special about you is that not only did you do it for yourself, there's people around you that have followed kind of the blueprint of how you built the Hustle.

I'm very proud of that. A lot of people have done that. A lot of people who worked at my company have gone on to build media companies. Very awesome, yeah. You know what, let's get into it. And I actually have um a post, a LinkedIn post from—by the way, I have to say there was so much luck involved in my journey, so I don't want to I always want to make sure I don't like—I had a plan, but there was a shitload of luck that it worked out. Yeah, yeah. And and actually your co-host on my first million, Sean, um, I want to read this post then get your reaction to it. So he said, "I just sold my second company, the Milk Road, and I'm super happy. We grew it from 0 to 250,000 readers in less than a year, self-funded and profitable, biggest daily crypto newsletter." He then goes on to say, "I was inspired by my buddy Sam Parr, who I got to watch step by step build the Hustle from scratch over several years. I copied and pasted his blueprint, but for crypto." Yeah, he did. He used the same ads and everything. Um, so you know what, let's let's get into the blueprint. Someone sitting at home, obviously they got their laptop in front of them, they think that building a newsletter could be a good start.

I remember when when we spoke about it, you said first you have to be a good writer. Yeah, if you're going to be like if you got to be talented, yeah, you got to have skills, you got to have attributes, you know what I mean? So talk about talk about how does someone become good at the skill of writing? I don't think everyone can be good, but I think everyone can improve. The way that I did it was I used this technique called copywork, which is basically where I would get like the—and it's like a proven method to learning writing. It's the same way where if you were to learn piano, I wouldn't just point at the piano; I'd be like, "Go write me a song." I would say, "Learn Happy Birthday," and then we're going to do Jingle Bells, and then we're going to move to like some simple blue L music, and then eventually you're going to do that for 5 years, and you're going to learn to like steal and be influenced by a bunch of your favorite people, and you're going to have your own flavor. That's I think it's the same case with writing. And so what I did was I found my favorite books, my favorite um, famous newspaper articles, I found famous um sales letters, like like website copy, and I would spend an hour every day, word for word, writing it by hand. And that's how I learned how to do it.

You know what, I think in the beginning part of the the reason that makes it difficult—you don't even know what's good. Like, I remember when I started the podcast, like I don't know what a good podcast episode is from the perspective of someone who's like a host, from the perspective of someone who's world-class. You don't really even know, as the beginner, what's good. So how does—when you say find good writing or like sales letters, like who, what are some examples or people that you were following? That like—I would Google like, "What's the world's greatest sales letter?" Like, it was that simple. And there was like a famous Wall Street Journal advertisement that went out that told a really good story, and they the Wall Street Journal claimed that this was the most successful ad of all time. So like, it was that simple. Or it would be like The Catcher in the Rye, like a very famous American book. Like, I would just Google like, "What are some of the most like beautifully well-written things?" Like that, that's what I did. J.N. Appal, the famous comedian, uh, D, the comedy director, he would do like famous SNL skits where he would write it out word for word. Um, and so just whatever you like aspire to be similar to or to write similarly to, you just copy it word for word.

You know, actually, I actually love that framework. I think the thing I love about it as well—you made it like a daily practice. Every day you have to do it, yeah, yeah. To this day, sometimes if I have to write something, I'll I'll go and do it. Yeah. Can you can you talk about more of that process in detail of like what was it that you were doing every day? Like, it has to be done not on like literally with a pen and a and a notebook. So in my home, I saved them; I have got stacks of yellow notebooks, and I would spend roughly an hour every day for like 10 months uh, just writing it word for word. And it was even—and then I would like underline it. I'm like, "Oh, that that phrase, the way that he the way that he instead of using a comma there, he used a period, and he started the second sentence with the word 'and.' That was kind of intriguing how he that made me feel," you know what I mean? Like, I would just like write little notes in the margins like that. Yeah, you would get into the specifics of it. There was even—you actually wrote out the framework; I saw it in an email. You said, "Step One is read and absorb. Find a great piece of writing that you would like to copy. Write it by hand on a piece of paper. Got to be by hand. 30 minutes a day. You say do not miss a day. This can potentially change your life. Skip one day, and you'll likely skip the rest." You then go on to say, "Make a swipe file throughout the day as you see writing you like, save it. A swipe file is just a folder of writing examples that you like." And then number four, the final one, you say, "Before writing anything important, spend 3 to 5 minutes copying your favorite writer." Yeah, that shit works, man. And I didn't I didn't invent that process. I mean, that's like uh, up until like the probably 1920s, I believe that's how we learned how to write in America. Uh, but yeah, it's the best way to learn how to write in my opinion, yeah. And so it's even like I'm curious like even when you were building the Hustle in those initial days, each time because there was a point where you were the only writer there, yeah. So when you would do these posts, three to five minutes before you even started, you would be there just like copywork. Yeah, I had I had authors who I loved, and I would just copy them for a few minutes, and I said, "Today I want to act like this person. Today I'm going to write like this person." Yeah, I did that all the time. Yeah. You know, I actually think both parts are important to your point, which is like you were doing the copywork, but then you were actually applying it somewhere as well. Yeah, and that's why it's addicting, yeah, because I would hit send, and then people would buy conference tickets, and I'm like, "It fucking worked! I got to learn how to do this more." Like, it was awesome; it was a really good feeling. Yeah.

How do you come up with your own style there? Well, you're just influenced by a bunch of people, and you you steal from five of them. So like, for example, I love this writer named Felix Dennis. My favorite favorite writer; he's got a book called How to Get Rich, and he's hilarious, and I think his writing is the best. I'm also inspired by Anthony Bain; I love his writing. Um, this other author um or this copywriter, Robert Ogie, or sorry, um, David Ogilvy, uh, I just like would find people. I'm like, "This is great; I love this; I aspire to be like this." You know what I'm curious like, before someone actually like how do you even know that you're a good writer? Like, before someone even starts a newsletter, like most people suck; most people suck when they start because the way that you're trained in school isn't exactly the most entertaining way. Um, and so like, for example, my favorite framework is AIDA: Attention, Interest, Desire, Action. And in high school, you're taught—have you heard of Bing Bang Bongo? Do you remember that? No? Do you remember like—I don't know what they did where you grew up, but in America, it's like you have to have a thesis that like says like, "Today I'm going to explain why running is such an an uh why running is so good for your health," um, and it starts with why it's good for your cardiovascular system; it's good for your muscles, and it's good for your lungs, and then you have paragraph one for cardiovascular system, paragraph two for your muscles, paragraph whatever, and it files—it's like horrible. And then you end with, "In conclusion," it's like the most like unengaging way to like write. We actually had the same thing; we didn't call it what do you say—Bing Bang—there's like a lot of ways to do it. I there's what do they call like a three-point thesis? Yeah, we we put it PE, so it's Point, Evidence, Explanation, and like every paragraph would have to have that follow that structure. Yeah, I don't like that at all. Uh, so I like AIDA: Attention, Interest, Desire, Action, uh, and that's like a way better format. And so like if you—most people suck because they're following these things that they were taught in school, but that's an incredibly unengaging way to write. Yeah. You know what, can you can you explain AIDA? I think it's going to be so good for someone. Yeah, so let's say that I'm trying to convince you to drink more water. I could say, uh, "Drink more water; it's good for you." That's not the most convincing or engaging thing. Instead, I could say—let's say that you are into like building your muscles. I'm like, "Hey, dude, have you ever seen those bodybuilders with huge muscles at the gym carrying around a gallon of water?" So that's an attention-getting uh sense. Um, you see uh, and this is the interesting the uh the reason they're doing that is because water actually grows your muscles by 20% if you drink it while you're working out. I don't know if that's true; I'm just making it up. Um, and so that I got you interested; you're like, "Oh, I want to learn more about how to get big mus big muscles." And then desire is like, "Look, um, it's actually proven that if you drink this muscle, it does this one thing to your to the oxygen in in your muscle, and it grows it by 30%. The only thing you really have to do is drink water every single day, um, and you can't skip a day, uh, but but if you do if you do that after one year, you're going to look like starting here, but now you're going to look like here. Here's your after photo." I just made you desire it. And then the action is like, "So all you need to do is go buy a water bottle, make sure it's at least one gallon tall, or just use a milk jug, fill it up with water at 8:00 a.m. every morning, and make sure it's completed by 9:00 at night." That's the action. I told you specifically how to take action. And so that AIDA formula, I use for everything. You know what? It's so good, and um, it's interesting like once you start to understand that framework, you'll see see everywhere; you'll see it everywhere, like even even with—you're talking about writing; it's exactly the same in short-form content, right? Everyone always talked about the hook; the hook is the attention; it's the attention grabber. And then like the sentences that come afterwards, they're building on whatever the theme was in the hook; that's the interest. And then the desire is like making you want it at your core. Yeah, it's—you see it everywhere; it's just uh, it's in it's in sales; in s—like when you have—have you heard like cold call people like in like you're in like a boiler room? I used to be like have to like do cold calls, and they would say uh, they would say AIDA: Attention, Interest, Desire, Action; this is what we have to do. Uh, and so yeah, it's just a very easy framework for selling. Okay. You know what, let's move on to the next step. So let's assume let's just assume that the person that's listening is a great writer; they're using their AIDA. Yeah, you have to be good. People forget that step; they like, "I want to get in the newsletter." I'm like, "Dude, but you suck! Like, you're not—" Yeah, your product isn't good. So you have to have a good product. Yeah. Let's say that the product is good; what is the next step? I know when we we spoke, you said you have to plan the business; like you have this process of reverse engineering your success. Do you have your phone on you? I do. All right, you're gonna help me do some math. So there's a few assumptions that we're gonna have to make. We're going to have to make the assumption that you're going to make money through advertising. There's a bunch of ways to make money through a newsletter; advertising is the most popular. At the Hustle, we actually owned an advertising newsletter as well as a paid subscription newsletter, but let's just assume it's advertising. So a lot of people, they'll say, "I want to create—" I just had this one kid email me, say he's going to create a newsletter on how to um pick which is going to be the winning fight for a UFC fight. And so I'm like, "All right, so let's do the math." So so you're going to send that email one day per week because there's four fights per month. How many people in the world are going to want this? Let's say you kick ass; I don't know, 50,000, maybe 50,000. Now the ad rate for them, I would I I could go and find this by just typing in um like, "How much does DraftKings pay per thousand impressions?" It's called CPM. I'm just going to guess and say it's $10. So you're going to do—on your phone, do—so 50,000 divided by 1,000, that should be 500. 50,000 divided by 1,000, yep. All right, times four because we're sending four times per month, yeah. And then what did I say the CPM was? 10. 10 times 10, that's what—times 10. So I got 2,000. $2,000. That's how much money you're going to make. That's shit. The reason it's shit is because—and people say like, "Well, but I'm passionate about this." And I'm like, "Yeah, dude, but the CPM sucks, and not that many people want this thing," uh, or if they really do want it, their buying power is like really low. They're just like—what does a bunch of people who want to bet on sports have in common? They're going to make some bets, but they're probably small, and like the commerce is not particularly huge. Now let's say that you have um doctors. Let's just say that you have doctors um, and there's 50,000 doctors in the world. Now let's say they need news uh like every day, six days a week. You're going to send them um the latest and greatest on what's happening in the world of heart surgeon heart surgeon news or something; I don't know uh, for them, I bet you can charge $1,000 per th uh per thousand cents. And so let's say there's 50,000 of them, so there's 50—so that would be uh 50 times, and we're going to do it—we're going to send because it's news—we're going to send it more than one day per week; we're going to send it six days a week because it's news; they want something on Sunday as well as well as Monday to Friday. So six times four is what? 24. 24. So we're going to send 24 times a month. So 24 times uh um 50 is what? Is 1,200 times a thousand. 1.2 million. Okay. So you see the difference. So that's 1.2. Now a thousand is quite high for a CPM, but what the point of this exercise is to show you that if you pick the right market and you if you pick the right type the right type of content that you're sending—so I can't send UFC picks that often because they don't happen that often, but I can send you doctor news. I bet you there's something going on in the doctor world all the time. I can send you that six days a week. And so I just showed you with 50,000 uh in one industry and 50,000 subscribers in another industry—one makes two grand a month; one makes $1.2 million a month. You see what I'm saying? Yeah. So the math for the Hustle when I started it was um—I think I can get three million people to subscribe to this newsletter. I'm going to email them 26 times per month, and I think I can charge $50 per 10,000 cents on average, and that came to be—you know, we could do the math again, but that came to be like $50 million. And so whenever you're starting a newsletter, you have to do this math to determine how big is the potential opportunity that you want to go after. And so you have to do this thing called an E-K-Y guide, you know, E-K-Y guide is—yeah, so it's like it looks like Olympic rings, and so it's like a it's like a Venn diagram. So what I'm good at, what I love to do, what do people want, and what are people willing to spend for? You want to find something right in the middle of all that because a lot of times people be like, "Well, I love sports; I'll make a sports newsletter." But it's like, "Dude, people don't pay for that shit for to advertise because that has like such a low advertising rate." You need something like B2B or something where like the person reading your newsletter has a will spend a lot of money—a doctor, for example. If they're making decisions for a hospital, an advertiser would advertise with you because they say, "If this person buys MRI machines from my account, I'm—they're going to—you know, I'll be able to sell $5 million worth of MRI machines to them," you know what I mean? So that's the math behind the whole thing that you have to do early on, in my opinion. Yeah. You know what, that's so good, and I I love it that we actually went through it step by step because it just shows—it shows the difference. Um, here's the thing that I'm curious about, and I think it's what's going to be the objection of people that are listening, which is—I think most people—even this is questionable—but most people know the things that they like, and they tend to have an idea at least about what they're good at; they don't really know what people are going to pay for. So how do you even figure out—it's very easy. So it—so to determine a CPM, here's how you—so an advertiser—so let's talk about it from an advertising perspective. So a person advertising on your newsletter, sometimes they're either brand advertisers, which means they just want to spend money to look cool, like a Toyota. Like, if Toyota runs commercials on TV, I'm not entirely sure if that's going to make me buy a car, but like if I see it a fuck ton of times, some people will. Or they're direct response, meaning they're going to click a button right there in on the ad and buy a buy something. And so they're usually one or the other, sometimes a little bit of both. But if you're buying an advertising uh an advertisement in a newsletter, you're going to want to see a profit. So if I spend $10,000 with you, I better make at least $10,000 in sales. So in order to do that, you have to do the math. So if I'm um let's say I'm selling a newsletter—let's say I have a newsletter that is only to 500 people, but it's the 500 people in the whole country who make decisions on buying supplies for the top airlines. So what do you think the top airline average contract value would be if you're like the guy who makes decisions for which type of tires go on the the wheels, you know, of the airline? Yeah, like millions, right? Millions. I don't know what it is, but it's millions. Now what do you think if it's for um 25-year-old dudes who like comedy? Like, not a lot. So like if I'm going to advertise—well, there's 25 dudes who like comedy; I mean, I guess I can advertise a comedy show, but I don't even know if they're all going to be in that city. So maybe I'll make like 500 bucks back if I advertise, you know what I mean? And so the ad rate is determined by the uh quantity and the quality of the reader. So for example, 1 million mothers who live in Middle America who make $40,000 a year, that might be the equivalent to 100 or 1,000 airline parts buyers, you know what I'm saying? And so the the equation of how uh valuable your newsletter is, it basically would look like number of people multiplied by how engaged they are, so how influential you are over them. So if you get behind a product, do they actually like that—like where they follow what you say—multiplied by uh uh the price of the product—H. Does that make sense? Yeah. You know, it's actually such a good point because I think when people think about things—my rambling, I'm sorry. No, no, no, you're good. When when people think about a newsletter or the value of a newsletter, they think purely about the number of subscribers. No, what you're saying is actually the spending power of those people that are subscribed and how engaged they are—how much influence do you have over them? Yeah. So for example, MrBeast has huge engagement; so his engagement is crazy high over a huge amount of people; they aren't exactly the biggest spenders; they're kids, but that adds up to a shitload of chocolate bars being sold, you know what I mean? Can you can you actually—I like I like one of the pieces that you brought up, which is actually engagement and influence. How do you actually—say I'm a great writer, and I've actually chosen an audience that has a good level of—

Spending power is what kind of things were you doing with the writing to actually have influence, to actually be able to sell products off the back of it? I wrote like a person, and so they felt like they were my friend, and they liked me, and that was like the easiest way to do it. Um, to test that you could, I would write an email that says, um, “I need a good book to read. Reply back with a good book.” And if I was sending an email to 10,000 people and only like three people reply back with a book, I’m like [ __ ] these people don’t care about me, you know what I mean? Like things like that. Like I would just write to them.

The cool thing about a newsletter is you write it as if it’s just me writing to you, not me to millions of people. Just I’m writing to you, that’s it, and I’ll talk to you as such. Like I’ll, I will ask for a recommendation sometimes, or I will like, um, tell you something silly that’s going on in my family life. And uh, that built a lot of loyalty.

Yeah, would you almost say there’s a direct correlation between like the more personal you get, the more that you almost feel like a friend to them, the more influence you had? Yeah, 100%. That was our slogan, by the way, at The Hustle was like, “You’re smart, no-nonsense friends who’s going to send you [ __ ] free news every day.” Yeah. You know what, now that you say that, it makes sense what Sean said that he kind of like the blueprint with the Milk Road was like exactly the same as that. It was exactly the same. It was like your friend that understands crypto, basically. He stole that line for line from me, and then, and then we grew to 100,000 people organically, and then after that we used paid ads to grow. And I came up with this ad; it was um, it was a qu- it was a quote that I just made up. It was, um, “My boss thinks I’m smart. I’m not. I really just read The Hustle.” And I spent probably $10 million on that ad or more; I don’t even remember, promoting that across Facebook. And if you Google that ad right now, so many other people have used that ad. That ad was like a really good ad. I got lucky; it just worked out. And Sean used that exact same ad. Yeah, “My boss thinks I’m smart. I’m not. I really just read the Milk Road on crypto.” Yeah, uh, and a lot of people have used that ad. Yeah, that’s hilarious.

Okay, so, so the equation is almost like it’s the like the number of people in your audience, so your subscribers, yeah, and then it’s the engagement, and then it’s the spending power of those people. So I’m curious, cuz I’m sure it’s like a balance across all three. When does someone know that they have something that they should put more into it? Like you’ve got a niche that is worth building around. For me, it was a little bit of a gut decision. I just like, I looked at how much traffic Wall Street Journal got and Business Insider got, and they got tens of millions of people per month. So in my head I was like, I definitely, there’s definitely a million people in this world, and at least in America, that want this. Like I feel pretty certain. And if I can get those million people, here’s the outcome, is that a worthy endeavor? Yeah, that will allow me to hit my goal. So it was just kind of a gut feeling like that.

Yeah. You know what, one of, one of the things you mentioned earlier, you said that in the initial stages you were doing all of the writing yourself, the newsletter, all of the writing you were doing? Yeah, but then I, I, I hired someone eventually, but yeah, I did a lot of it early on. How big can someone, like what revenue number could you think someone can grow a newsletter to, just doing it themselves? Um, I got it to 30,000 a month in revenue, uh, there’s a world, but back then there weren’t a lot of tools, but there’s like ad networks now that you could use. So I had to like go and email people and cold call them and ask them to buy ads in my email. Now there’s more like networks that you can use, but uh, I didn’t have a reputation then, so I was just cold emailing people. Nowadays, I could probably find five advertisers that would each pay a set rate every single month to advertise, and that would make my life way easier. I mean, if I were to start a newsletter, and I, which I never would, I don’t want to do that anymore, I definitely could do probably, uh, 300, I, I probably do at least three million a year, I would think, which just by yourself, just mean an assistant.

Dang. Yeah, I mean, yeah, because I would write the newsletter from 3:00 p.m. to like 6:00 p.m., and then all day I was spending growing it or doing business development. And I think I could get like five, there’s six advertisers to each pay me 50,000 per month, given I had at least 250,000 subscribers, and I could get to 250, I mean, I got to 250,000 subscribers in one year, so I, I could do it again probably. Yeah, now it’s a lot of work; you got to write a newsletter all the time, so I don’t want to do that, but it’s a lot of work. Yeah, but I think even for people listening that’s like an insight, like that’s almost your mind opening up to the fact you can build a $3 million newsletter with just yourself and an assistant, with like crazy margin. Is yeah, I mean, and I know possib- I have friends that do that. I’ve got friends that do two and three million with like them and two other people. Yeah, like you could do it for sure. And if you really wanted to do this, it would be harder to start, but it’s way easier to run. You do uh, paid a paid newsletter, so people like, I have a friend who does roughly 20 million a year and paid subscriptions, and he’s been doing it for 10-plus years, so it’s, but he’s doing 20 million a year just him writing.

Dang, that is crazy. Okay, you know what, so you mentioned obviously the writing piece, and then growing it and business development. Let, let’s start with business development. In the initial stages, you’re getting on these calls and like selling these ad spots. Yeah, this guy named Chris at Wealthfront, I called, emailed them, I said, um, well, I had a little bit of an advantage because I think the founder of Wealthfront spoke at one of my events, but I basically had like, at that point, 3 times 15, so 35 people spoke at different events, and I emailed all 35. I, I just used LinkedIn, and I found the marketing managers at all 35 of the companies. I was like, “Hey, um, my uh, your founder spoke at my event. I’ve now started a newsletter. I currently have,” I think I started advertising when I had 50,000 subscribers. I was like, “I have 50,000 subscribers. I think this is worth uh, at least like uh, $5,500 or $2,000 for you to advertise on. You want to do it for a grand, uh, and if it works, keep on going.” And they were like, “Yeah, I, I’ll try it for $1,000.” Yeah, I, I’ll try it. And I did, and it worked a little bit, uh, and they would keep on going. And I did that to get to 30,000, and then I hired an advertising sales person, a full-time person, and within two months we got to like 70 grand per month. Like once I hired someone dedicated who knew how to do, I’m not that good at, to, to sell advertising. You got to be pretty organized; I’m not that great at it, but once I have like a really organiz-IED person who knew how to do it, I mean, we, it, it got you 100 grand in like a few months.

Yeah, that’s awesome. Okay, did you, was there, was there ever any stories? I know people fear this with sales, cuz once you sell it, you have to deliver. Was there one where you got like someone in, they like agreed to the rate, and then you almost like hopelessly under-delivered? I felt like that all the time. I mean, we, we did a good job of delivering, and if I didn’t deliver, I had a policy that like, “Dude, if we don’t deliver, just give them their money back, or like, give them, make them whole.” So if I, the cool thing about a newsletter is that like my production costs are like nothing. So if you’re not happy, I’ll just add you again in tomorrow’s edition, do you know what I mean? Like, and that was, and that’s what I would do. I was like, “I need you to be happy,” because with the advertising business as well as any other business, repeat customers is key. And so we ended up hiring account managers who’s sole job was to like say, “Hey, uh, HubSpot or Salesforce, here’s the results of your campaign. We got a lot of wonderful feedback for it, um, we had, you got this many clicks; it looks like you had this many signups for whatever. How, how are you feeling? You know, like, let me get you on the phone and walk me through how you’re feeling about this. If you’re happy, we can do a little, we can iterate, we can like, like, like it was like a, it was like an enterprise sales gig, you know what I mean?

Yeah, I love, I love the way that you said that, like, “Make it whole,” like make them whole, because I think so many people when they’re doing sales, they get the sale, and I’ve done this actually, you get the sale, instantly move on to the next one, like you deliver the thing. No, you gotta like provide value, dude. You gotta, you gotta, you gotta like, I won’t. Yeah, like I have a podcast now, and like, I, I don’t want you to advertise unless you’re going to make a profit, you know what I mean? It’s got to be a win-win, otherwise you’re just a fool, and you’re going on to make a little bit of money, and then in a few months you’re never going to see it again. Yeah, they ch- it’s the death of your business. Yeah, churn is, is the most important thing I think for, for every business is, is retention.

Yeah. You know what, let’s quickly talk about the, the growth piece. So let’s say that I, I have the sales locked in, I’ve got, you know, I’m good at writing. How do I actually grow this thing? Like what are the best ways in 202-? The key, so I’ll tell you what we did, and then I’ll, I’ll, I’ll guess what I think the best thing today is. So the key is you have to know, “Who am I targeting?” Like literally name them. Like what is this person? So for me it was like a 26-year-old who lives in New York, San Francisco, LA, works at any of these thousand tech companies and makes like 100 grand a year. That’s who I’m going after. So they’re kind of a nerd, but where do they hang out? In my case, they hung out on Reddit, uh, that was like a nerdy hangout place at the time, um, so I was like, all right, what subreddits were, where were they hang out, and, and what subreddits and what topics are they currently reading about? And so I went and created content that I felt had a good chance of ranking high on those subreddits that were relevant to the person who I wanted to attract. And so for example, you remember Soylent? Yeah, yeah, yeah, the drink, right? Yeah, it’s like a Dr-, it’s like a meal replacement drink that like engineers would drink. I paid a guy two grand to live on it for 30 days and like write about it. Yeah, and so I had the headline, I thought about the headline first, the action, the ADA, uh, of, “I lived on Soylent for 30 days; here’s what it made; here’s, here’s what happened.” And I posted that in the subreddit for Soylent, and we got like 50,000 people who came to the site that week. And I would do these like big articles like that all the time, and a lot of them hit, some of them didn’t hit, but I would always think like, all right, so my audience is on Reddit, it’s on Hacker News, and at the time it was in a variety of Facebook and Facebook groups. So I’m going to create content that’s long-form articles that’s tailored for those people using headlines that will capture their attention. And then when they come to my website, I had a really funny popup that followed ADA, and it said, “Oh, [ __ ] not another popup,” and I said, “Hey, look, while you’re here, here’s the deal. This is actually a blog that I’ve written to promote my daily newsletter where I tell you all the business news that you need to know. Sign up now; if you don’t like it, I’ll owe you a dollar.” And we would get like 30,000 people a month signing up for that, um, and I would just churn these articles out like crazy. So only like 30% or 20% of them got a lot of traffic, but I would churn out so many that it kind of added up. So we were able to get 100 or 150,000 subscribers in the first 12 months, maybe. And so if you do that full time, you could bang out that many articles too.

Yeah. You know, it’s, it’s so good, and it’s like it shows how foundational and how important that ADA framework is, right? Because all that you were doing is that you’re creating the attention, is like the viral article, the thing that gets, I don’t know, hundreds of thousands of people see it, maybe like a smallish segment of those then click through to your page, maybe 10,000, and then you, then have the interest and the desire built in the popup, which then convert any of the call to action. And then my welcome email was really good. If you Googled The Hustle welcome email, a lot of people like wrote blog posts about it. It was like a very famous welcome email that I wrote that was really good. Um, I try to do what’s called the forgotten text, so the for- so your welcome email, your unsubscribe page, things where you just use the stock text from a your web provider. Yeah, I always would customize those, that like, or your popup, I would like customize them to like stand out, um, and that really worked well.

Yeah. You know what’s interesting about business and entrepreneurship? I think a lot of people that are really good at it, especially guys, started off as like gamers. And when I, when I hear, when you, even the way you’re explaining it, it makes sense because it’s kind of like, I don’t know, it’s like when you learn, I’m trying to think of the right game, but like it’s when you learn those like strategy games or like those games growing up where you kind of figure out the way it’s played and the rules, and then you’re just optimizing the [ __ ] out of it. And it’s just like, and that was the thing with the newsletters. A lot of people didn’t think that it could be a real business, but I was like, but no, like the math says this, and they’re like, “But dude, an email is like a joke.” I’m like, “No, no, no, this is like the rules of the game are this, like, but let’s just add like three zeros behind like your subscriber count, you know what I mean?” And, and that math still works.

Yeah. If you were going to use the same strategy in 2024, what would you do? Well, it all depends on where your audience is already living. So if I was going to do tech and business, my audience is living on Twitter right now, so I would get popular on Twitter. If you’re appealing, you know, if you’re into a car newsletter or something like that, car YouTube is like pretty popular, then I would make YouTube videos and get them to convert to um, a newsletter. If I’m, for me, I would never do a consumer newsletter; I would only do B2B, and if it’s B2B, I could probably advertise to get them, and they would be on LinkedIn, and I could probably acquire a customer on LinkedIn. I don’t know what that goes for anymore; I haven’t done it forever, but like I get, I bet you I can get a LinkedIn subscriber or a subscriber from LinkedIn for like five bucks, and I bet you I can make like five bucks a month off of them through ads in my newsletter, do you know what I mean? So the reason you, um, the reason that you say you would do B2B if you were doing it now, they spend more; they spend more, and because the, the, the bar of content is [ __ ] like a lot of like B2 boring. Yeah, so [ __ ] boring, so it’s like it’s not that hard to like be cool, you know what I mean? Like I was a tech news newsletter; it’s not that cool; the industry wasn’t cool. So if I just said a silly joke every once in a while, people thought it was like the greatest thing they ever heard. Yeah, you know what I mean?

Yeah. You know, I was reading someone say this, um, recently, like everyone thinks about like TikTok or YouTube, Instagram, all these platforms. No, dude, it’s way too hard. LinkedIn, and it’s like still wide open to. Yeah, it’s way easier; it’s way easier to go B2B, and you make so much more money, uh, like I’ve got a friend, um, or a guy I’m friendly with, and he’s got a company that had only like a million subscribers, and he sold it, I had two million or three million subscribers, and we sold for tens of millions. He had like a million subscribers, and he sold for 500 million, and it was like all B2B, like the most boring [ __ ] like HR and [ __ ] like that, uh, because like the head of HR like makes software buying decisions that are really costly, important, right? So anyway, like B2B is way better, way better. What makes someone buy you? Like when, when you get the, I don’t even know if you’ve had this conversation with the people at HubSpot, like what is it that they’re seeing that makes them buy the news? The HubSpot, on. So there’s basically two reasons: one is they just want the IDA. So do you know anything about PE or anything like that?

Yeah, it’s a hard industry. I don’t like PE; I’m not an expert into it, but basically, uh, private equity, private equity, uh, you have a fun, let’s just use math, um, you have $100 million fund, and what you do is you say, “I’m going to with $100 million fund, I can buy 10 companies that are collectively worth a billion,” and the reason I could do that is because I’m going to use my 100 million to buy the companies, and then I’m going to borrow $900 million to pay for the company, and in doing that I’m going to buy companies that have uh, cash flow, and I’m going to slowly grow the cash flow, and then I’m going to sell that business in seven years, and I’m going to return 1.8 billion dollar. These guys get one bill, they’re 1 billion plus a percentage of the 800 additional million that we made, and I’m going to turn my 100 million into 500 million. You understand what I’m saying? So that’s how PE works. And so a lot of buyers in newsletters are, they just want that cash flow. In my case, it’s a called the strategic, it’s actually way better. So HubSpot is a company that sells CRM and website software; they sell it to small business owners, and the average um, price of their software I think is around $20,000 a year. The Hustle had roughly two or three million people on their newsletter, of which a lot of them were small business owners as well as people who made software buying decisions. So HubSpot is thinking, “Well, I could go and buy ads to grow HubSpot, or I could just buy this newsletter and never have to buy an ad in newsletters ever again,” because if I convert 0.1%, which would be of a mill, 0.1% of a million people is what, 10,000? So if I can get 10,000 of them to buy my $20,000 software, that’s a lot of money, you know what I mean? And that’s how they thought about it, and, and there was good math; they did a good job.

That makes sense. So it’s either, it’s just such an extreme cash-flowing asset, or it’s just a strategically, strategically for their business. Strategic is a way better way to sell, by the way; you get way higher multiples. Yeah, that makes sense. Okay, no, this is so good. You know what, here’s, here’s where I want to end. We spoke kind of like in your origin, like wanting to be in control of your life; that was like the big thing, that was the thing that you really felt is like you just wanted to have this autonomy, this control over your life. I’m curious now because you seems like you’ve kind of done all of the things right, like you have great wife, you have child, you’ve made the money, like what is, what is your, even, you know what, let me put it like this: if the self that’s before me now, you’re 30, you spoke with the self that was 21 or 15 or I don’t know what age is the one that’s like an inflection point for you, what would you tell them? Because it’d be an interesting conversation to just achieved. Yeah, because you got the thing. Um, I really believe in like making a plan and following the plan and trusting the plan. I would tell myself to do that. I think, um, I think I would tell like 15-year-old me, I’m like, “You’re the [ __ ] man, you can do it.” Like I, I really was not a very confident person. I knew I had some type of like, I mean, everyone has a little bit of special stuff about them, and I wanted to like hide like my uniqueness. I like kind of felt like it wasn’t cool to be like a dork and [ __ ] like that. I’ll be like, “No, like lean into that [ __ ], lean into your weird quirkiness.” Like I remember being a kid, I’m like, “Dude, I wish I was like in part of a family like these TV shows where like they were all nice to each other, or like I wish I lived in like one of these nice houses like in California; I’ve never been.” I’m like, “I wish I want all these things.” Like, no, like it’s, it’s cool to be different, and like lean into like your kind of weirdness, and that is cool; people will be attracted to that, and you will get to where you need to go if you lean into that and don’t be self-conscious about like being quirky or being weird. And uh, I just be like, “No, you’re, you’re the man; it’s cool; it’s cool to be unique.” Make sure you beat, uh, what’s the phrase, uh, uh, “Watch your own drum beat” or something like that, like do that. March to the beat of your own drum. Yeah, I wish I would have had more confidence in doing that earlier on than I did.

Yeah. And you know what, it’s, it’s even funny just, um, when I’m doing these interviews, having these conversations, I observe the guest, right? As you’re speaking, and it’s like I said it earlier, it’s almost like the degenerate guide to business. Every time that you speak about these stories of you like doing these, you’d be really embarrassed of that stuff, by the way. I was really embarrassed about it. I was like, “I’m just like a [ __ ] redneck; like what am I doing? I want to be more…” But now your face lights up when you talk about it. Yeah, I was like, “I want to be more refined; I was like I want to be all, all the…” Like, no, like be unique, and um, like even now I’m 35, and I hang out with people that are a little bit older than me sometimes, and they’re more, I’m like, “I’m still a kid,” and I was like self-conscious about that for a minute. I’m like, “No [ __ ] that, dude; that’s the way to go.” And so I’m now, I feel very confident, um, that like the world is shaped by people, just normal people, and like I can make my own reality. I could kind of kick my Deb in the world. And so now I’m a lot more confident of like not bending into other people’s reality; I’m going to bend my own. And so now I’m a lot more confident, but yeah, I wish I was more confident about that early on of like, you don’t have…

To do it the way other people do it, you don't have to act the way other people are acting, like it's all right. You could have your own path. Yeah. You know what's funny? I actually wrote that in my notes. I said, "I want to maintain my childlike wonder." That's like the biggest thing. Like, if you can maintain your childlike wonder.

I was on the subway on the way over here; there's this little kid sitting next to me, and everyone's quiet. He just starts shouting out. Kids would do that; they'll just—they're just themselves; they control their own reality. And it's like, if you can maintain that, and you can lean into it, the things that you're good at, you can achieve incredible outcomes. Yeah, and it feels awesome. Like the world wants you to be vanilla; don't—don't give into it. You know what I'm saying? Um, um, also, life goes by really fast, and like you got to do it your way a little bit. You know what I'm saying? Um, and I get care of that. Yeah, yeah.

Thank you so much, man. Appreciate it. Thank you so much for watching this episode. I hope you enjoyed it. It's really a dream for me that I get to do this. It's surreal that this is what I do full-time, and every week. So if you enjoyed the content, if you enjoyed the conversation, the stories, please hit that subscribe button. It helps us immeasurably with growing the channel, with getting guests, all of those things. So please hit that subscribe button, and I'll see you next time.