Every Business I Tried Before Making My First Million
All right, everyone, on this podcast, we talk a lot about the successes, but I want to talk about the failures. So here's about 10 different companies that I started before I made my first million. Almost all of them, they sucked. It didn't work. But I'm going to explain how much I made for each idea and the lesson that I learned.
I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel. All right. What's up, Sam?
What's going on?
Let's set this up. Name of this podcast, My First Million. When did you make your first million?
So cash, like cash million, I made it when my wife worked at Airbnb and it went public. And that, that's when we made our first. And then about 3 months later, I think it went later in December, my company sold in February, and then we made a lot. Leading up to that, we were doing pretty good too, but I don't think we had crossed $1 million.
Okay, so you made your first million, let's call it 31 years old. Here's all the businesses you tried before that, before making your first million, which I think is pretty fascinating. I want to go down this list. Does it start in high school? Yeah. All right, go for it.
Give me number 1. In high school, I made $2,500 one summer by buying graduating seniors' old sports equipment and selling it on eBay. And so what I used to do is I would just buy like people's like track spikes or, uh, you know, whatever. And I would sell it on eBay. And most of the time I didn't buy it. They would just give it to me. They would hand it to me. And I, on eBay, I made $2,500. That was my first business where I actually started making online money.
And this is flipping, basically. This is flipping assets that other people not only undervalue, they might even not value to the point where they're just happy you took it off their hands.
Yeah. And frankly, I did this in college too, which I didn't list here, is when at the end of the college year, I would, I would stay a few weeks after the end of the school year. And when people were moving out, I said, I have a storage unit. You can come and put it here and just give it to me. You're going to throw it away. Just give it to me. And then I would resell it.
Exactly. I saw people doing this in college with textbooks. They would just say, oh, at the end of the year, you don't want to take all these heavy textbooks home. You're done with that class. Class. Well, guess what? The next semester, there's a bunch of people that are going to need that exact textbook that were happy to buy it used. And so they would just go buy up people's tech. They would just take people's textbooks, and each book was like, you know, a $40 or $50, uh, you know, future sale that they were able to pick up for free.
Okay. And then at 20, I started a hot dog stand, which everyone makes fun of me for talking about. I have a hot dog stand, you have a sushi restaurant. They're sick of us talking about it. But I had one called Southern Sam's Wieners as Big as a Baby's Arm. Basically, I knew a guy named doc who had a hot dog stand. He let me rent it from him with very little money up front. I had— I was able to pay him on the 30th as opposed to the first of the month. So he hooked me up and with $500 I went to Restaurant Depot and I bought a bunch of Vienna sausages to get my supply. And I was in business, baby, within a week of having this idea. And I used to live in a bad neighborhood. Rydell was my next door neighbor and he became my best friend. He had served 20 years in prison for attempted murder and somehow we became best friends. He had the— he had the spare key to my house. This was my guy. And Rydell ended up working with me at Southern Sam's, and we spent all day outside and it was a pain in the butt. Some days I would make $50, other days I would go to a concert or like an outdoor place that was popping and I would make $1,000. And I did that when I was about 20 or 21.
This is your summer in college or what were you doing?
I was in college, I was in class. And so I would work until 3 p.m., I would go to classes from 3 p.m. until 8 p.m. And then I had a night session where I was out by all the bars and that would be like 9 p.m.
to like 1 a.m. That's amazing. How did you have the idea to do the hot dog stand? You just saw somebody else doing it?
I met a guy who had a cart and I wanted to do something.
Yeah. Did he tell you, like, I'm making $300 a night or something?
What did he say? I saw a video online of a guy saying how much money the Home Depot hot dog guys make. They make $100,000 a year, the ad said.
And you were like, in.
I was in, man. I was, I was broke. I had my PhD. Poor, hardworking, and driven. I was—
would you do this again?
This one? No, man. It was so hard. It was so hard.
No, not now. But like, if you were 19, 20 again, you needed to.
And I didn't have to sell constantly, didn't have to stand there in the heat.
And didn't have to stand in the heat. I will post a photo here. I had these horrible— I mean, look at me. I'm like the whitest guy ever. I had these horrible sunburns that when I took my tank top off, it still looked like I was wearing a shirt. Just a white—
like, Peter, there's this, uh, there's this tweet that's been going viral that's, um, so they said flirt with everyone. Flirt with women, flirt with men, flirt with old people, flirt with kids, just flirt with everybody. It's non-sexual, but literally just be the most playful, charming person you could be at all times. Like, practice this muscle. And, um, I actually think this is 100% true. I know a couple of people in my life that are like this. I'm not really like that, but I've been starting to do it just for fun. Just as a little mini game. You know, when you're just living a pretty routine life, you're just going to the grocery store. It's either going to be a forgettable experience or you try something to make it a little more fun. I've been doing this and it's kind of amazing.
Like, you know what I call it? You know how people say nonchalant? Be chalant. Be chalant. Don't be nonchalant. Be chalant.
Chill out as hell.
Yeah, be chill out, try hard.
I, uh, I emailed my wealth manager at Morgan Stanley and I was like, hey, I made this trade and it like, it was like a commission of like $100-something at the end of like the trade. I was like, is there like a magic button you got over there, man? Like, do you got this magic button you could push that makes all those fees go away? And that was what I sent, you know, the private wealth manager. And he goes, he just replied, magic button pushed. Trades, commissions reversed. Enjoy your trading. And I was like, just flirt with everybody. Like, I could have been an annoying Karen. I could have just— I could have just took it, done nothing. I could have been a Karen complaining. Just flirt a little bit. Everybody likes to be flirted with.
So my next business after that, I started this thing basically in Tennessee at the time, white whiskey, which it's called moonshine. Moonshine technically means illegal whiskey, but there was these companies making whiskey that was in a Mason jar and it, they called it moonshine. And I started selling that online and I thought I was doing it the right way because I kind of like Googled it and I talked to like a lawyer where I was like selling it as a novelty because it was kind of like a gift item. I did that for about 2 or 3 months and then I went to my university's like entrepreneurship program where they had free legal advice and I was like, hey, I've made $10 grand in like the last, like, you know, 30 days or something selling this whiskey online. I think I'm following the right rules, but is there anything else I need to be doing? And they're like, yeah, brother, you gotta— you better shut that down tonight. And so that was like my second internet business, which inspired me to get into the game of the internet. And my lesson learned on that one was, if you're going to do something like this, you better really do it right. And you better pick something that aligns with your values. Around this time, I was still drinking and I didn't even like alcohol. But I mean, you know, I had a love-hate relationship and I was like, why am I going to start selling this? I don't want to do this. This is stupid anyway. But you're going to see there's a pattern. It was definitely like a quick money, which I think everyone who becomes a good entrepreneur, they do the gray hat, gray hat area phase. And this was my gray hat phase.
Okay, I like it. You started it online. Did you learn about online marketing through this? Like, were you— how did you— how did you get the $10K? Where did you— where did you get your customers from?
I posted on forums like motorcycle forums, like, so basically like this whiskey that I was selling, people were already searching for it because the guy— drink and drive, of course. Yeah, that should have been the name. People were already searching for this whiskey, but it was very early. And so I was able to rank super easily on Google and I posted on message boards, forums of people who wanted it. And that's how I made money. Nice. All right. So a lot of people watch and listen to the show because they want to hear us just tell them exactly what to do when it comes to starting or growing a business. And really a lot of people who are listening, they have a full-time job and they want to start something on the side, a side hustle. Now, a lot of people message Sean and I and they say, all right, I want to start something on the side. Is this a good idea? Is that a good idea? And again, what they're really just saying is just give me the ideas. Well, my friends, you're in luck. So my old company, The Hustle, they put together 100 different side hustle ideas and they have appropriately called it the Side Hustle Idea Database. It's a list of 100 pretty good ideas, frankly. I went through them. They're awesome. And it gives you how to start them, how to grow them, things like that. It gives you a little bit of inspiration. So check it out. It's called the Side Hustle Idea Database. It's in the description below. You'll see the link, click it, check it out. Let me know in the comments what you think.
Okay, so now you move to San Francisco. I think you, you don't you just do like a cross-country motorcycle ride to get to San Francisco as well?
I do it at a later date, but this time I flew out there because I had a job offer at Airbnb, which got rescinded when I got there because I'd lied on my resume about getting a DUI. And so I was out there. I'm like, what the hell am I going to do? I got to meet people. And so I started a thing called the Anti-MBA Book Club. And I tried monetizing it, but I couldn't really at first. And so what I did was I posted ads on Craigslist and on Reddit, and I think I posted on Facebook and I got 2,000 people to sign up. But here was the premise. It was called The Anti-MBA because I was very envious of Stanford students and Berkeley students. I was very envious that they had this network and said, I'm going to read one book per month. We're going to break it up into a quarter. So a week, a week, a week, a week. And I'm going to find an expert on that book's topic and we're going to come and discuss it with that expert. I'll organize and get the expert. You come, it's free. And I got 2,100 people to sign up to my emailing list and I had about 20 people show up every single week. Some of those people include Sieva, who's now one of my best friends. It's one of your close buddies, Neville Medhora, who's now— who was the best man at my wedding, came from that. And so it was my best friends came to the Anti-MBA Book Club. And if, and I posted a photo, if you zoom in on the top left of the photo, you're gonna see a skee-ball machine. I found an arcade that let me host the book clubs for free in that place as long as we'd play skee-ball.
And you were, uh, reading books. Now, what kind of books were you reading in this? Is this like, were the books actually useful for you in business or was selling white whiskey the right way to learn business?
I don't remember everything we read, but it was like, it was like Tim Ferriss's book, The 4-Hour Workweek. So you know how like you want to like, if I was a techie, I would have built like Clubhouse or something actually cool. But I didn't have like anyone discuss these books that I wanted to read. But it was kind of a forcing function because I was like, look, I need to get good at business. I better like get educated. What I could do is I can get these people to come to this book club and I'll just read one week in advance and I take really good notes and I'll sort of teach it. Because when you do a book club, by the way, no one reads a book, just the one guy who is organizing it. And so I was just going to organize it, organize and talk about it.
Okay. What came next?
Okay. And then around that same time, when I moved to San Francisco, I met a guy who had an idea for a roommate matching app, and I was like, hey, I don't have anything to do. May I please join you? And so I previously had a pickup truck in Nashville where I live. I sold it. I had roughly $5,000. He had a little bit of money. We put it together and we started with this idea called Bunk. And the idea with Bunk was it was a roommate matching party website.. And so we went to landlords who had 2, 3, 4, 5 bedrooms, and we would say, we're gonna post an ad on Craigslist and we're gonna advertise this 3-bedroom as a 1-bedroom apartment. Meaning instead of a $3,000 3-bedroom, we're gonna advertise it as a $1,000 1-bedroom, and we're gonna get 100 people who are interested and we're gonna host parties to help them team up and move into this apartment and potentially other apartments. Hmm. Sounded interesting and it was somewhat interesting. Couldn't figure out how to monetize it. Roommate matching apps are one of like 4 businesses that every just every graduated college kid tries to start. That's one of them. It doesn't really work. So we got Aqua hired roughly 9 months later, which basically meant we got a job and we got some bonus money if we like accomplished a couple things. But what we did do that was interesting, and I was not able to do this, I was definitely like the marketing guy, but we turned that idea into Tinder for roommates. And that was really dumb because most people, when we launched, when we got, we actually got tens of thousands of people to sign up for it via these infographics that I linked to that we made., but most people or many people who were using it were just meeting it to date. We should have just done Tinder for Tinder. It would've been way smarter. Um, and so that didn't really work out.
Okay. So I think that to win in business, you gotta have essentially 3 components. The first component is you need to have a money-making skill, meaning you have to have something that drives value. This is either gonna be learning to sell, learning to make things, learning to hunt down interesting deals. Right? You need a moneymaking skill. What was your moneymaking skill you were developing during all these— across all these different little projects?
Copywriting. And also just like tenacity, but like getting after it. But copywriting was the one. And marketing.
Marketing, right? Learning to sell. In your case, learning to sell, learning to sell through—
Getting website traffic and getting the web visitor to do what I wanted them to do.
Cool. The second thing is You got to learn to be sort of tenacious and scrappy, which comes not as a thing you want to do, but as a thing you are forced to do because you really have no other choice. But once you find that gear, you now know you have it. That's how I would describe it. Is that accurate? It sounds like it's what happened in your case too. Nobody wants to be scrappy, to be clear, right? Like, if you had the option to not have to tough it out, you would probably have taken that. But when you're forced to do it, you learn, okay, I have this sort of animal inside. I can do this. And now I'm going to use this in every single thing I do. Whereas somebody who doesn't know if they could do that, they're hesitant to go for it.
Yeah. And what's funny about that tenacity or sorry, being scrappy is there's this chart where basically like you, you start that way and you don't like it and then you like kind of get some, a little bit of fancy. But then once you already are fancy or successful, you realize you should always be scrappy. You know what I mean? There's like a reason that like Amazon has like the pizza rule where it's like you'd only have a team of people that are like 4 people. Because small, scrappy teams do significantly better in many cases than bigger teams.
And so, yeah, when we, when we met, it's actually hilarious. If you had just taken a picture of both of our offices and you had said, which of these two guys is a successful entrepreneur?
My office was like a museum.
You had a—
dude, if you walked up to Sean's office, I'm not exaggerating you. In San Francisco, we live by Yosemite and the redwood trees. They're huge. You could drive it. You could cut a hole in it and drive a car through it. Sean's office, as it's as if they made a, like, a coffee coaster for your cup out of a redwood tree. And it was the size of like 18 feet long. It was like an 18-foot in diameter circle that was like a probably a half a million dollar table.
Yeah, it was. We had 4 stories. We had an entire apartment built in with heated bathroom floors. So if you needed to stay the night, you could sleep there. Every, every wall was made of one-way, one-way mirrors. So you could like see out, but they couldn't see in.
You had a chef.
We had a chef there every single day. We had a masseuse on Fridays. We had open bar. Uh, so every Friday we had— so all these things. It's a full— it's a 30,000 square foot office decorated by Ken Folk, one of the fanciest designers in the world. And, uh, that was my office. I remember Sam came over one time and he picked up the ashtray, which nobody smokes inside. I don't even know why we have an ashtray. It's like illegal to do that. And he picked up the ashtray, flipped it over, and he goes, this is a $700 ashtray. 'cause the sticker was still on it. And I was like, I don't know what to tell you. I don't know what I'm doing here.
And I stole it.
It's like the Titanic got built and then they just plucked like a 23-year-old idiot and they were like, you drive. And I was just driving that company into the ground. And you had this like half an office. It was like literally like somebody's apartment.
It was an apartment that was $700. Me and Siava shared it.
Yeah, like the bathroom didn't have a door. Like you just had to be like, hey, I'm taking a shit. You know, like it was like the craziest scenario. Siava was just sitting over there. Wasn't even a part of your company. Just like another guy was just there. And, um, like the, the, the wall, like there was, everything was so strange. Like nothing made any sense. You like didn't have Wi-Fi and you were building this internet company and yet you actually were the one who was building something successful. And at that period of our lives, like you were actually onto something and I was sitting here just like, you know, making things that nobody wanted. And so, uh, you know, your scrappiness was well-deserved at that time and, and, and earned you. Some good things. I had to go through my scrappy period at a different time. So the third thing I would say, so one was, uh, the tenacious side, developing that scrappy mentality and being willing to be at the bottom and like survive at the bottom. Two is the money-making skill, and three is project selection. So starting to figure out like almost through process of elimination, what are all the bad businesses that you should not be in?
I was in the elimination phase for sure.
Yeah, you eliminated like, hey, I probably don't want one where I'm standing outside in the heat selling hot dogs because I'm going to be capped at like how long I can stand outside in the heat. That's probably not a good idea, right? So manual labor, it's not scalable. Um, you know, another one that you did was like illegal business. Like, oh great, a lot of people want this moonshine, but like, it's only going to go— the bigger it gets, the more likely I am to go to prison, fail and go to prison. So that's probably not a good project to select. So you were going through process of elimination on project selection. And so you go through this roommate matching app, you're making apps now, that's already better. If I say like, what's the Sampar criteria now after doing all 10 of these things? What is a good project to be in for you?
I believe in Ikigai, which is like, what's the world want? What's the world want to pay for? What am I good at and what I'm passionate about? And I try to find that in the middle. But I— my goal and then, okay, so that's like the woo-woo stuff that I totally believe in. But then the other side is, can I get something? Can I bootstrap it to $100 million in revenue in 10 years?
Okay, but can I bootstrap it? So there has to be some— something you're answering underneath that. That's like saying, you know what, my strategy in chess is checkmate, right? Like, okay, yeah, I get it, but how do you get there exactly? So what do you look for that's going to be a thing you can bootstrap? So are you looking for, I can see that somebody has done a similar thing in another space that I can recreate or apply over here? Seemed like the hustle was very much that way. Yeah. Um, the newsletter, right? You looked at the scam, you looked at a couple others, you were like, oh, I get what they're doing and I could do that just in my way.
Yeah. So I like to, I call it like a forgotten business. So there's a lot of these businesses that I haven't even talked about on MFM. But basically, like, there's a bunch of businesses like Hampton that are doing hundreds and hundreds of millions of dollars a year in profit. And what I tend to do when I look for— I mean, Hampton's my only company. That's what I'm going to be doing for a very long time. But before I started it, I research and I go and talk to the owners and I do diligence. And I thought of it this way. But then when AI started coming in play, it really solidified it, which is like something that can't be disrupted easily. I also like looking at things that serious operators don't take serious because I think that there's less competition. So like with The Hustle, people laughed at me when we started it, but I was like, well, if you do the math, it definitely can get to $100 million in revenue. And I sold before it got there. But Austin Reiff, who founded Morning Brew, he only sold part of the business and still kept running it. And they're in the $80 or $90 million revenue, I think, range now. So like the math was right. And so I look for things that can be real opportunities, but the ballers aren't taking it serious.
Yeah. What Charlie Munger says, the secret to success is weak competition. And so if I was to say from afar, I've known you for, I don't know, how long have I known you?
12 years, maybe. Yeah.
Long time. Um, 3 Obamas. And what I would say is I've noticed that one thing you do really well is you're very good at sniffing out interesting things in spaces where other people are not, not even looking, which is you mostly just following your curiosity and taste. Uh, but you go and you do a lot of research. You do, you come across nonchalant, but you're pretty fucking chill about the research. I'm very like, you go, you go really detailed, you go meet them, you like talk to the bankers, you talk to a lot of people in a space to get a real, like a real idea of like what those companies look like.
And because I want to eliminate the uncertain, like, okay, so entrepreneurship, I've been thinking about this. The reason I think entrepreneurship is almost philosophical to me and a lot of people is because entrepreneurship is sort of like how much uncertainty and fear can you take and still continue moving forward. Because entrepreneurship is basically like you work on the same thing for 6, 12, 18, sometimes 24 months and you're like, I still see barely any progress. Is this going to work? And the price that you're paying for potentially a big outcome or potentially for building a business or potentially being free, it could take 5 or 10 years. And the ones who win are the ones who can handle that uncertainty for a long period of time. That is what entrepreneurship is ultimately, in my opinion. It's dealing with uncertainty and dealing with fear. You have fear over hiring someone when you only have $30,000 in your bank account. You have— I remember when my first employee had a kid and I was like, it feels like I had a kid. I felt so much fear. Now this really has to sustain itself. You have fear over finding your first customer and thinking, I promised them one thing. Now I really have to work my butt off to like make it work out for them. You have fear over getting hate, uh, and people making fun of them. And so the name of the game of entrepreneurship is just, can you handle the fear? And can you handle what's worse is the uncertainty over potentially 5 or 10 years.
Beautifully said. Mohnish Pabrai had a good, uh, addition to this, which he said, understand the difference between risk and uncertainty. So he was talking about it with the stock market. He goes, basically, the stock market— stock market investors hate uncertainty. Like, if they don't know whether your earnings are going to be good or bad, they will just sort of assume bad, right? Like, you basically get a huge discount for uncertainty, but it's not the same thing as actual risk. And, you know, risk is like, you know, what do you have to lose? Uncertainty is just not knowing what's going to happen. And so people think that entrepreneurs take a lot of risk, but I actually think that you are a good example of what most entrepreneurs really do, which is they're actual risk minimizers. It's like, how do I win while taking the least amount of risk necessary to win? I'm not trying to take risks. I'm not trying to take unnecessary risk. I'm trying to vaporize risk everywhere I can. And whatever's left over, fine, I'm willing to live with what's left over. And he tells the story of Richard Branson. So he says Branson is seen as this like freewheeling gunslinger, Mr. Risk type of guy, partly because of his look, his brand, etc. He goes, when Branson started his airline, which is a very— what people would think is a very risky business to be in, most airlines fail. Even today, most airlines don't even make any money, though even the airlines that exist are very razor-thin margins. And when he started Virgin, he called up, I think it was British Airways, and he was trying to get one plane. So he was like, hey, do you have like, whatever, a 747? And they were, they were telling him, no, we don't just give out, we're not going to sell you, random guy on the phone. Like, he called the customer support. We, we don't sell you a 747. Can you just connect me to the person who does sell 747? We don't sell 747. He's like, all right, do you guys have extra capacity of 747s that are not currently in use in your fleet? They're like, yeah, we do. He goes, okay, well, would you lease one to me? And basically he started Virgin by leasing the plane, not buying the plane, which reduced risk. He released it and he was only on the hook for the payments like after, like 60 or 90 days later. But he was already going to pre-sell the tickets for the flights. Like the airline business works where you sell the tickets before you end up paying for the, for the plane and the fuel and all the the actual cost of operating it. And so he realized, like, actually, well, what's the worst case that happens? I just give them the plane back. Like, that's all I'm on the hook to do is give them the plane back if I can't follow through on my commitment. But if I can get it to work, I'll know ahead of time because I sell the tickets upfront. So it's actually a, a very like risk reduction approach to doing what other people see as taking massive risks. And I would say you're the same way where when I've seen you go into a business, you're looking to reduce risk everywhere possible. So you're like, do, uh, does another business like this already exist and work? So I know that there's demand and I know the business model works. Can I apply it into this space where there's not a lot of competition or there's weak competition? There's not a lot of other really smart super geniuses running around San Francisco trying to do what I'm doing. Cool. That's a way of reducing risk. A third way of reducing risk is you try to bootstrap it. You don't take on external investment. You try to do it where I can start this with pretty much no money. So what do I have to lose? Just my time. I'm not actually going to be in the hole if I— if this goes wrong. That's another way that you reduce risk. And the fourth one is, can I use basically my copywriting skills to attract demand before I have to fulfill the service?
I would sell sponsorships before. Yeah, I sold sponsorships. I wouldn't sell, but yes, I would, I would pre-sell as much as possible.
Right. And so, you know, and you would do a bunch of research to reduce risk. You would talk to the bankers to figure out, you know, what works in these businesses. You talk to the ex-CEOs, the ex-employees to understand what works, what doesn't work in this business. And so I think you're a master risk reducer. And so when somebody sees the businesses that you do, they all sound kind of random. But I would say like where you've come to, I think at the end is you've figured out your moneymaking skill, you figured out how to be tenacious and scrappy. And then lastly, you've gotten better at project selection. And ultimately we'll use sort of a risk reduction method to pick a project that you think is like kind of a— I wouldn't say slam dunk, but like you're not hoping for this sort of 1 in 100 outcome. It's kind of like I have to fumble execution for this to fail. Today's episode is brought to you by HubSpot because using only 20% of your business data is like dating somebody who only texts you in emojis. First of all, that's annoying. And second, you're missing a lot of the context. But that's how most businesses are operating today. They're only using 20% of their data unless you use HubSpot. That's when all your emails, your call logs, your chat messages, they turn into insights to help you grow your business. Because all that data makes all the difference. Learn more at hubspot.com.
You should hold your breath still on saying I had good project selection because in 2015 I started a business called Itch Juice, a poison ivy treatment.
Scratch your own itch, as they say.
So stupid. So there was this like type of lotion that mechanics used. It was like a called a green scrub. I forget exactly what it was called, but it, it turns out it was also had the same ingredients as poison ivy treatment and I bought in bulk like a, like a, like a barrel that you would have at a mechanic shop. And it was like $0.20 an ounce. But that as poison ivy treatment, it sold for like $20 an ounce. And I realized I could rank high on Google. And so I was, I got in the poison ivy treatment business and I learned the same thing there that I learned in the alcohol business, which was, and this, this did, this was starting to make money, which is like do these short little get rich quick schemes that you jump into without like doing the Ikigai preparation of like, what am I actually passionate about? They're stupid. So I learned that one.
I feel like I was a lawyer who just stood up and told the jury my client is innocent. And then at the very end you were like, I did it, by the way. Yeah, it's like, oh, I told you, just don't say anything.
Now I think I did good at selecting new things, so I got rid of that. And then I started working—
10 years. I think that I have the same story where it took 10 years for me to even figure out what a good business is.
Dude, I don't know how, like, I read about these prodigies, um, who do, who like are so mature when they're like 26, 27. And I just, I'm like, am I, was I just like slow to develop? Like when I see some of these smart 26, 27-year-olds, I think to myself, I still don't behave that way. And I'm 10 years older than that. So I don't, like when I was 26 and 27, like I, I didn't know anything. I knew nothing. And I actually felt this way about you. And I was like, he writes stuff on a whiteboard and he's got these frameworks way of thinking. I don't think in frameworks. I just do. Yeah.
While I was sitting there being like, why am I just on a whiteboard? This guy's out there just doing it. I got to do what this guy's doing. It took me 10 years to even figure out at all what the hell was going on. 10 years. And 10 years, you could say that. Look, I said that in 10 seconds. It took me 10 years. Watch. That was so quick. When you're in it, 10 years is like an eternity, especially because you don't even know that. If I knew, by the way, It'll take me 10 years, but I'll figure it out. It would've felt so much better. At the time, it's like the tunnel is still dark and I don't even know where, if and when the tunnel ends. And I don't know how much like time I've got left to get there. So it feels much worse in the moment. So for anybody who's out there who's in their kind of tenure, tenure doing dumb stuff arc, you know, I feel you. It's normal. It still works. Just keep going.
So Lewis and Clark, it's like one of my favorite stories ever, but they basically, they were sent out starting in St. Louis. Thomas Jefferson was like, hey Lewis, hey Clark, do me a favor. Just walk in that direction and tell me, does it end? And what's it look like? And what's on the end? And they just go. And back then, obviously phones didn't exist, mail didn't exist. They were just walking around and they didn't know where they were going exactly. And it took them 2 years. So imagine that. Imagine sending someone off on a trip for 2 years and having no idea like what's going on, if they're ever going to come back. And that's what entrepreneurship kind of feels like. It could have took 2 years, it could have took 5 years, who knows? But we're just gonna go in that direction and I pray and I hope that we're gonna find something. That's like what the uncertainty feels like.
Yeah, exactly. And every year you're like, now I know now. And then you say that again the next year, like, oh, well last year we were so, so dumb, but this year now we have it figured out. And it takes a certain amount of self-delusion to not be like, hey man, listen, you said that 3 times already and now do I really believe you this time? And so you need, You need delusion. I think actually that's also why you got to move to San Francisco is because you'll be surrounded by success stories and you'll see them and be like, okay, cool, that guy's not special. I could do it. If you could do it, I could do it. And also everybody around you is similarly deluded, which really helps because, um, you sort of brainwash yourselves into this mode where you're going to keep going, keep taking shots, and that that's a normal, rational thing to do, even though it's a completely abnormal, irrational thing to do. I think it's one of the biggest benefits of coming to Silicon Valley.
Can I rattle off just a few tiny ones? So I did this thing called the Frisco Disco Taxi where we dressed up in disco outfits with afros and we gave rides home for people on New Year's Eve.
Yeah, Tinder too. Tinder too. Yeah. We made $800 that night. I did a copywriting class with Neville. We actually hosted it at your office. I think we each made $10,000 or maybe made $10,000 total. And then another couple failures. I bought some real estate and I learned that basically the way you make real estate is through doing the most due diligence upfront and looking at tons and tons and tons of property because you make your money when you buy. And that is not my skill set. And then of course I had The Hustle. The Hustle started as a conference, then to a blog, then to a newsletter, which worked. We launched this thing called Trends, which was a fairly successful thing, and then we expanded our events business. Events, businesses, horrible. The way that we did it, horrible. We had hundreds or thousands of people coming to each event. Way better to go after smaller groups and charging a lot more. But back then I couldn't even imagine the idea of someone being willing to spend $2,000 or $3,000 or $4,000 or $5,000 per ticket to a trade show. And I wish I would have figured that out.
Yeah. So me and Tyler, the CEO of Beehive, came up with a little challenge for you. It's the newsletter challenge. Now, if you know me, You know that I'm a big fan of newsletters. I got my own newsletter. I also had a business that was a newsletter business that was amazing. I wrote this newsletter about crypto. We grew it to quarter million subscribers and we ended up selling it after a year for millions of dollars. And I want you to be able to do the same thing in your business. So we're doing a challenge. $10,000 is on the line, plus me and Tyler will actually be in your corner as growth advisors. You just need to go to beehive.com/mfm and you either start a new newsletter or you move your current newsletter over there and 5 5 finalists will get picked to pitch me and Tyler, sort of like Shark Tank, and the winner gets $10,000. So go to beehive.com/mfm. That's beehive.com/mfm to enter the challenge today. And then this podcast turned out to be a business. We didn't really realize it. You know, I definitely, I started it alone. I definitely didn't think of it as a business. Then you joined. I still don't think we thought of it as a business for what, the first 2 or 3 years?
For the first 9 months, I'm almost certain it made $0. Right?
No, I had a sponsor somewhere there. I mean, round down to zero.
Yes.
Like, you know, like $10,000, $20,000 or something.
So I posted this photo. I want— I want people to, like, understand this. So Sean came up with the podcast, I think, in July, and then I think I joined him in September. So he did a bunch alone and then I joined him later on, I think sometime in December. So we're talking 6 months in. Lance Armstrong, for some reason, read The Hustle and I became friendly acquaintances with him. He wanted to use my office where Sean and I were recording the podcast. And so he came that day when Sean and I were recording because he messaged me saying, I need to use an office for a meeting. Can I use this? And I said, yeah. We pull him into the podcast as we're recording. And I posted this photo of me, Lance, and Sean standing there. And we only have two microphones and two chairs and two chairs. And Sean's just like, Sean's like, sitting on like the arm of my chair. And during the, and during the episode when Sean wants to talk, he has to like lean in to reach my microphone. And then another episode we had someone like, we had a guest call it. It was like a digital guest. It was me and Sean in real life, not a guest. For some reason, one of us didn't have AirPods. And so we just like shared an AirPod. Like we each had one in our ear and I think we were recording on an iPhone. Like it was so janky even 6 months into it.
Yeah. Which was funny too, because it's not even like these were the early days of podcasting. It's like pretty late in the game of podcasting.
Someone should go and look at those old chairs that we used. We picked these chairs because there was a podcast at the time called Fighter and the Kid, and they use these bright red chairs, the brightest red chairs, and we figured they use it so it sticks out on a thumbnail. Which I don't even know if we did YouTube at the time, but we wanted those chairs and it is just a hilarious looking set.
Honestly, it got to be pretty cool when we were in person together. It was pretty amazing. I still wish we could be doing that.
Oh my God, it would be the best. It would be the best. It was so much fun. And we had like a— we ran to Best Buy and bought like a video camera and we had an intern record us and the shot is just you and I like it's dead on you and I talking. And the guys that we were copying was Theo Von and Brennan Schaub, who obviously Theo Von is Theo Von now, but back then he was like a cameo. He came in as a cameo for this other podcast.
Yeah, good times.
It feels nostalgic going through this stuff, doesn't it? Because you were with me for most of it or a lot of it. But doesn't this— is this kind of fun to like look back and like, it's crazy, this stuff that we've done. Yes.
I mean, when you're in it, you just want to get out of it so bad, right? God, I just want something to work. Anything. Is this going to work? I really hope this thing works. And I just wanted to get out of it so bad. And then now you're right. You know, you look back and I've really never had as much fun since as I did on The Come Up. Like, The Come Up was really— it was a lot more, I don't know, high variance or just like unpredictable and like crazy stuff happened. And it was fun things that I would never make the time to do now. Like, you're never going to go do Sam's Frisco Disco now. You're never gonna go do the hot dog stand now. But actually those are pretty fun, like kind of random projects, great stories, great photos, great like memories of trying to pull it off that you were at the time, you know, too dumb to know it was dumb. And now unfortunately, you know, you sort of have the curse of knowledge the further you go where you're less likely to go try random dumb things that might actually have high, you know, high upside or high fun or high memories, you know, that come at the end of it.
We have a lot of like young guys listening to this who are in their 20s. Enjoy it, man. It was, it was such a blast. It doesn't feel that way. But I would say with a high degree of certainty, if you do the same thing or you try really hard for 10 years and keep taking risks, you and I, Sean, have dozens of friends from that same era and we have seen dozens of them, like many, many, many of them succeed. Not always like total home runs, but we have many of those. But a lot of base hits, a lot of doubles, a lot of life-changing businesses have been built. And it's so exciting to like look back and be like, it works. You just gotta do it.
Yeah. It is, I mean, it sounds corny, but the truth is at the time you think your success is about how hard you're working and maybe your idea or your team or your execution of the individual thing. And that's true, like at the project level, but at a personal level, the only thing that's gonna determine your success is basically your rate of learning. How quickly are you figuring things out? Are you adapting and learning and getting better at your next shot than you were at your last shot. It's that rule of 100, right? Like, do 100, try it 100 times, and each time try to make one thing better. If you do that, success is pretty much inevitable. But at the time, you don't think like that. At the time, you don't really realize that. But looking back, that's very much the case. I'm sure there's some people who have a way to get there a lot faster. You know, for both you and I, it took 10 years because we sort of, through process of elimination, got rid of most of the dumb things. You did do one thing differently than I think most people did. You never made the mistake of building something nobody wanted. Which is maybe the main mistake I did. I had a bunch of things that the business sounds great on paper. If it works, it's going to be huge, but nobody even wants the thing to begin with. So you die on the launchpad, whereas you made the opposite. Everything you made, people wanted, whether it was hot dogs, whiskey, whether it was like, you know, a way to get rid of their itch, whatever it was, you know, you had a way. You always made something that people wanted. Sometimes the business model was broken or the scalability was broken, but I feel like you did the— you did one thing really well, which is you never made the cardinal sin, which I would say most entrepreneurs make, which is you do something that sounds good on paper, but nobody actually wants the thing you're making. And you spend all your energy trying to convince them why they're wrong and why you're right. And actually, no, they just don't want it. They don't need it.
You know what's funny? Looking back, I like, for example, The Hustle. I think we were at 100,000 subscribers in year 1, and then I think it was 500 in year 2, and then 1,000,003, something like that. And that sounds lovely. It didn't feel like it at the time. It still felt like I was pushing a rock up a hill. And so you're saying I made things that people wanted. Um, looking back, I agree. But when you're going through it, like I remember Ryan Hoover launched Product Hunt and people were talking about his product way more than like my product. And I was like, that, that's what product market looks like. Not mine. I've never experienced that. What the hell? And I look back at it and I did have it. And so some of these things, when you're in the thick of it, you have to really work hard to try to come up with these lessons in the, like, at the time. And you have to, like, sit by yourself to come up with these lessons in the time because there has been so many things looking back where I'm like, had I only done this, I would have had so much more. I would have worked so much better. But I didn't learn those lessons in the process. So for example, I used to think that it— I was like, I want to become a big company, so I have to act corporate. Now I know you want to act small as, as long as you can, or if you have something that is growing at like 50% a year, don't mess with it. That's a great growth rate. Whereas if you see other people or I saw other people at the time growing significantly faster, but, but, but they ended up like dying and blew up. But I was like, I want to grow that fast. What the hell? And I'm looking back, I'm like, no, no, no, that was, that was a rocket. That was fantastic. That was great. It was bootstrapped. It was, it was beautiful. I think that that I heard this line that basically says VC is like rocket fuel. And you know who deserves rocket fuel? Rockets. Not fast cars, not cool cars, not cars that you love. Rockets. And the thing about rockets is most of them blow up and don't go anywhere. A cool car, a great car, a car you love, that could be an amazing life and it could actually get to the destination eventually, but it might go a little bit slower. And I thought that was an insult to me. I said, but I want a rocket and I want it to work. Nonsense. I wanted a car and I wish I would have like had the confidence back then and learned that lesson that that was the way. All right.
So that's Sam's story. Made his first million at 31. But instead of focusing on how he did it, which we've talked about before, it's the, you know, I don't know, 10, 15 things he tried before that, the stumbles and fumbles on the way to success. I'm going to do mine. We'll do one next episode. I'll do my— I'll do my version of that where I tell you all the terrible, terrible ideas that I had going up to finally making it. I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back. Hey, let's take a quick break. I wanna tell you about a podcast that you could check out. It is called "The Science of Scaling" by Mark Roberge. He was the founding CRO of HubSpot, and he's a guest lecturer at Harvard Business School. The guy's smart, and he sits down every week with different sales leaders from cool companies like Klaviyo and Vanta and OpenAI, And he's asking about their strategies, their tactics, and how they're growing their companies as, you know, head of sales or chief revenue officer. If you're looking to scale a company up, if you're a CRO or head of sales that's looking to level up in your career, I think a podcast like this could be great for you. Listen to The Science of Scaling wherever you get your podcasts.