Sam walks through roughly 10 businesses he started before making his first million — from flipping sports equipment on eBay in high school to a hot dog stand, illegal moonshine sales, a roommate matching app, and more. Shaan uses the stories to extract a framework: money-making skill, scrappy mentality, and project selection. The episode ends with a broader meditation on entrepreneurship as the management of uncertainty over time.
Speakers: Sam Parr (host, co-founder of The Hustle), Shaan Puri (host, founder of Milk Road)
Introduction: Failures Before the First Million [00:00:00]
Sam: All right, everyone. On this podcast, we talk a lot about the successes, but I want to talk about the failures. So here are about 10 different companies that I started before I made my first million. Almost all of them sucked. They didn’t work. But I’m going to explain how much I made for each idea and the lesson that I learned.
Shaan: All right. What’s up, Sam?
Sam: What’s going on?
Shaan: Let’s set this up. Name of this podcast: My First Million. When did you make your first million?
Sam: So cash — like a cash million. I made it when my wife worked at Airbnb and it went public. That’s when we made our first. And then about three months later — I think it was 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 a million before that.
Shaan: Okay. So you made your first million — let’s call it at 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?
Sam: Yeah.
Shaan: All right. Go for it. Give me number one.
Business #1: Flipping Sports Equipment on eBay [00:01:20]
Sam: In high school, I made $2,500 one summer by buying graduating seniors’ old sports equipment and selling it on eBay. I would just buy people’s track spikes or whatever, and I would sell it on eBay. And most of the time I didn’t even buy it — they would just give it to me. They would hand it to me. And I made $2,500 on eBay. That was my first business where I actually started making online money.
Shaan: And this is flipping, basically. Flipping assets that other people not only undervalue — they might not value them at all, to the point where they’re just happy you took it off their hands.
Sam: Yeah. And frankly, I did this in college too, which I didn’t list here. At the end of the school year, I would stay a few weeks after everyone left. 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 anyway — just give it to me.” And then I would resell it.
Shaan: Exactly. I saw people doing this in college with textbooks. They would say, “At the end of the year, you don’t want to take all these heavy textbooks home. You’re done with that class. Well, guess what? Next semester there’s a bunch of people who need that exact textbook and they’re happy to buy it used.” So they would just take people’s textbooks, and each book was like a $40 or $50 future sale they picked up for free.
Business #2: Southern Sam’s Hot Dog Stand [00:03:15]
Sam: Okay. And then at 20, I started a hot dog stand, which everyone makes fun of me for. You have a sushi restaurant. People are sick of us talking about it. But I had one called Southern Sam’s. “A wiener as big as a baby’s arm.”
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 could pay him on the 30th instead of the first of the month. So he hooked me up. With $500 I went to Restaurant Depot, bought a bunch of Vienna sausages, and I was in business within a week of having the idea.
I used to live in a bad neighborhood. Ryell was my next-door neighbor and became my best friend. He had served 20 years in prison for attempted murder, and somehow we became best friends. He had the spare key to my house. This was my guy. Ryell ended up working with me at Southern Sam’s. We spent all day outside. Some days I would make 50 bucks. Other days I would go to a concert or some outdoor event that was popping and I would make $1,000. I did that when I was about 20 or 21.
Shaan: This is your summer in college? What were you doing?
Sam: I was in college. I would work until 3:00 p.m., go to classes from 3 to 8, and then I had a night session out by all the bars from about 9 p.m. to 1 a.m.
Shaan: That’s amazing. How did you have the idea to do the hot dog stand? You just saw somebody else doing it?
Sam: I met a guy who had a cart and I wanted to do something. Yeah.
Shaan: Did he tell you, “I’m making 300 bucks a night” or something?
Sam: I saw a video online of a guy explaining how much money the Home Depot hot dog guys make. They make $100,000 a year, the ad said. [laughter]
Shaan: And you were like, “I’m in.”
Sam: Man, I was broke. I had my PhD — Poor, Hardworking, and Driven. I was in.
Shaan: Would you do this again?
Sam: No, man. It was so hard.
Shaan: Not now — but like if you were 19, 20 again and needed to make money?
Sam: I learned how to sell so well from this. This is what inspired me to get into copywriting. I realized you had to wheel and deal a little bit, you had to schmooze, you had to flirt. And then I realized: what if I could do this on the internet, where I could write something one time and have an infinite number of people come and read it — and I didn’t have to sell constantly?
Shaan: Didn’t have to stand there in the heat.
Sam: Didn’t have to stand in the heat. I’ll post a photo here. I mean, look at me — I’m like the whitest guy ever. I had these horrible sunburns where when I took my tank top off it still looked like I was wearing a shirt. Just a white beater-shaped tan.
Shaan: There’s this tweet that’s been going viral. It says, “Flirt with everyone. Flirt with women. Flirt with men. Flirt with old people. Flirt with kids. Just flirt with everybody. It’s nonsexual, but literally just be the most playful, charming person you could be at all times. Practice this muscle.” And I actually think this is 100% true. I know a couple people in my life who are like this. I’m not really like that, but I’ve been starting to do it just for fun, as a little mini-game. You know, when you’re living a pretty routine life and 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.
Sam: You know what I call it? You know how people say “nonchalant”? Be shalant. Don’t be nonchalant. Be shalant.
Shaan: Be shalant as hell.
Sam: Yeah. Be shalant. Try hard.
Shaan: I emailed my wealth manager at Morgan Stanley and I was like, “Hey, I made this trade and there was a commission of like $100-something.” I said, “Is there like a magic button you got over there, man? Do you have a magic button you can push that makes all those fees go away?” And he replied: “Magic button pushed. Trades and commissions reversed. Enjoy your trading.” And I was like, just flirt with everybody. I could have been an annoying Karen. I could have just taken it and done nothing. But just flirt a little bit. Everybody likes to be flirted with.
Business #3: Selling Moonshine Online [00:08:45]
Sam: So my next business after that — I started this thing in Tennessee. White whiskey, which is called moonshine. Moonshine technically means illegal whiskey, but there were these companies making whiskey in a mason jar and calling it moonshine. I started selling that online. I thought I was doing it the right way because I kind of Googled it and talked to a lawyer. I was selling it as a novelty — it was kind of like a gift item.
I did that for about two or three months. Then I went to my university’s entrepreneurship program where they had free legal advice and I said, “Hey, I’ve made 10 grand in the last 30 days or so selling this whiskey online. I think I’m following the right rules, but is there anything else I need to do?” They said, “Yeah, brother. You better shut that down tonight.” [laughter]
So that was my second internet business. It inspired me to get into the game of the internet. My lesson learned: 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 but I didn’t even like alcohol. I had a love-hate relationship with it and I was like, why am I going to start selling this? This is stupid anyway.
But you’re going to see a pattern. It was definitely a quick-money play, which I think everyone who becomes a good entrepreneur goes through — the gray-hat phase. This was my gray-hat phase.
Shaan: Okay. I like it. You started it online. Did you learn about online marketing through this? How did you get the 10K? Where did you get your customers from?
Sam: I posted on forums — motorcycle forums and things like that. People were already searching for this whiskey because the guy —
Shaan: Drink and drive, of course. [laughter]
Sam: That should have been the name. The people were already searching for this whiskey, but it was very early so I was able to rank super easily on Google. And I posted on message boards where people were looking for it. That’s how I made money.
Business #4: The AntiMBA Book Club [00:11:30]
Shaan: Okay. So now you move to San Francisco. You did a cross-country motorcycle ride to get there at some point too, right?
Sam: I did 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. So I was out there like, “What the hell am I going to do? I got to meet people.”
So I started a thing called the AntiMBA Book Club. I tried monetizing it but couldn’t at first. I posted ads on Craigslist, Reddit, and Facebook and got 2,000 people to sign up. The premise: it was called the AntiMBA because I was very envious of Stanford and Berkeley students. I envied that they had this network. So I said, “I’m going to read one book per month. We’re going to break it up by week — a week, a week, a week, a week. I’m going to find an expert on that book’s topic, and we’re going to come discuss it with that expert. I’ll organize and get the expert. You come. It’s free.”
I got 2,100 people on my email list and about 20 people showed up every single week. Some of those people include Sieva, who’s now one of my best friends and one of your close buddies. Neville Medhora, who was the best man in my wedding, came from that. Some of my best friends came through the AntiMBA Book Club.
I posted a photo — if you zoom in on the top left, you’re going to see a skee-ball machine. I found an arcade that let me host the book clubs for free as long as we played skee-ball.
Shaan: And you were reading books — were they actually useful for you in business? Or was selling white whiskey the right way to learn business?
Sam: I don’t remember everything we read, but it was like Tim Ferriss’s The 4-Hour Work Week. If I was a techie, I would have built something like Clubhouse, something actually cool. But I didn’t have anyone to discuss the books I wanted to read. It was a forcing function — I was like, I need to get good at business, I better get educated. What I could do is get these people to come to this book club, and I’ll read one week in advance, take really good notes, and sort of teach it. Because when you do a book club, by the way, no one reads the book — just the one guy organizing it.
Shaan: Right, so you were just going to organize and talk about it.
Sam: Exactly.
Business #5: Bunk — Roommate Matching App [00:14:20]
Shaan: Okay. What came next?
Sam: Around that same time when I moved to San Francisco, I met a guy who had an idea for a roommate matching app. I was like, “Hey, I don’t have anything to do. May I please join you?” I had a pickup truck in Nashville that I sold — I had roughly $5,000. He had a little bit of money. We put it together and started with this idea called Bunk.
The idea with Bunk was a roommate matching party website. We went to landlords who had two, three, four, five bedrooms and said, “We’re going to post an ad on Craigslist and advertise this three-bedroom as a one-bedroom apartment. Instead of a $3,000 three-bedroom, we’re going to advertise it as a $1,000 one-bedroom. We’re going to get 100 people who are interested and host parties to help them team up and move into this apartment — and potentially other apartments.”
It sounded interesting, and it was somewhat interesting. But we couldn’t figure out how to monetize it. Roommate matching apps are one of like four businesses that every just-graduated college kid tries to start. It doesn’t really work. So we got acqui-hired roughly nine months later — basically, we got a job and some bonus money if we accomplished a couple of things.
What we did do that was interesting — and I was not able to do this; I was definitely the marketing guy — was turn that idea into Tinder for roommates. Which was really dumb, because most people who were using it were just using it to date. We should have just done Tinder. It would have been way smarter. That didn’t really work out.
The Three Components of Business Success [00:17:10]
Shaan: Okay. So I think that to win in business you need essentially three components.
The first is a money-making skill. You need something that drives value — learning to sell, learning to make things, learning to hunt down interesting deals. What was your money-making skill developing across all these different projects?
Sam: Copywriting. And also just tenacity — getting after it. But copywriting was the one. And marketing.
Shaan: Marketing. Learning to sell. In your case, learning to sell through getting website traffic and getting the web visitor to do what you wanted them to do.
Sam: Exactly.
Shaan: The second thing: you got to learn to be 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. Once you find that gear, you know you have it. That’s how I would describe it. Is that accurate? Nobody wants to be scrappy. If you had the option to not have to tough it out, you would have taken it. But when you’re forced to do it, you learn: okay, I have this animal inside. I can do this. And now I’m going to use this in everything I do. Whereas somebody who doesn’t know if they could do it — they’re hesitant to go for it.
Sam: Yeah. And what’s funny about that scrappiness — there’s this chart where basically you start that way and you don’t like it. Then you get a little bit fancy. But once you’re already fancy or successful, you realize you should always be scrappy. There’s a reason Amazon has the two-pizza rule — only have a team small enough that two pizzas can feed it — because small, scrappy teams do significantly better in many cases than bigger teams.
So when we met, it’s actually hilarious. If you had taken a picture of both of our offices and said, “Which of these two guys is a successful entrepreneur?” —
Shaan: My office was like a museum. Dude, if you walked up to my office — we lived by the redwood trees in San Francisco, the huge ones you can cut a hole in and drive a car through. My office had a table like someone made a coffee coaster out of a redwood tree. It was probably 18 feet in diameter — like a half a million dollar table. [laughter] Yeah, it was. Four stories. An entire apartment built in, with heated bathroom floors. If you needed to stay the night, you could sleep there. Every wall was made of one-way mirrors so you could see out but they couldn’t see in. A chef there every single day. A masseuse on Fridays. Open bar.
It was a 30,000-square-foot office decorated by Ken Fulk, one of the fanciest designers in the world. And I remember Sam came over one time and he picked up the ashtray — nobody smokes inside, I don’t even know why we had an ashtray — he flipped it over and he goes, “This is a $700 ashtray.” The sticker was still on it. And I was like, “I don’t know what to tell you.”
Sam: And I stole it. [laughter]
Shaan: It’s like the Titanic got built and then they plucked a 23-year-old idiot and said, “You drive.” And I was just driving that company into the ground. And you had this half an office. It was literally someone’s apartment.
Sam: It was an apartment for $700. Me and SA shared it.
Shaan: The bathroom didn’t have a door. You just had to be like, “Hey, I’m taking a shit.” SA was just sitting over there — he wasn’t even part of your company, just another guy who was there. Nothing made any sense. You didn’t have Wi-Fi and you were building this internet company. And yet you were actually the one building something successful during that period. You were actually on to something. I was sitting there making things nobody wanted.
Your scrappiness was well-deserved at that time. It earned you good things. I had to go through my scrappy period at a different time.
Shaan: So the third thing — one was developing the scrappy mentality, being willing to be at the bottom and survive there. Two is the money-making skill. Three is project selection. Starting to figure out, almost through process of elimination, what are all the bad businesses you should not be in.
Sam: I was in the elimination phase for sure.
Shaan: Yeah. You eliminated: hey, I probably don’t want one where I’m standing outside in the heat selling hot dogs because I’m capped by how long I can stand outside. That’s not a good idea — manual labor, not scalable. Another one: illegal business. Great, a lot of people want this moonshine, but the bigger it gets, the more likely I am to —
Sam: Go to prison.
Shaan: Fail and go to prison. So that’s probably not a good project to select. You were going through process of elimination on project selection.
So what’s the Sam Parr criteria now, after doing all 10 of these things? What is a good project to be in?
Sam: I believe in ikigai — what does the world want? What will the world pay for? What am I good at? What am I passionate about? And I try to find that in the middle. That’s the woo-woo stuff that I totally believe in. But the other side is: can I bootstrap it to $100 million in revenue in 10 years?
Shaan: Okay, but “can I bootstrap it to $100 million” is like saying your strategy in chess is checkmate. Yeah, I get it — but how do you get there exactly? What do you look for that’s going to be a thing you can bootstrap? Are you looking for: I can see someone has done a similar thing in another space that I can recreate or apply here? It seemed like The Hustle was very much that way.
Sam: Yeah. The newsletter — you looked at the Skimm, you looked at a couple others, and you were like, “Oh, I get what they’re doing. I could do that in my way.”
Shaan: Right.
Sam: So I like to call it a “forgotten business.” There are a lot of businesses I haven’t even talked about on MFM, but basically there are businesses like Hampton that are doing hundreds of millions of dollars a year in profit. What I tend to do is research and go talk to the owners, do diligence. When AI started coming into play, it really solidified it for me — look for something that can’t be disrupted easily.
I also like looking at things that serious operators don’t take seriously, because there’s less competition. With The Hustle, people laughed at me when we started it. But I was like, if you do the math, it can definitely get to $100 million in revenue. And I sold before it got there. But Austin Rief, who founded Morning Brew — he only sold part of the business and kept running it — they’re in the $80 or $90 million revenue range now. So the math was right. I look for things that can be real opportunities but the ballers aren’t taking seriously.
Shaan: Yeah. Charlie Munger says the secret to success is weak competition. [laughter]
And if I was to say from afar — I’ve known you for, what, 12 years or something?
Sam: Long time.
Shaan: Three Obamas. 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 aren’t even looking. Which is mostly you following your curiosity and taste. But you go do a lot of research. You come across nonchalant but you’re pretty chalant about the research. You go really detailed. You go meet them. You talk to the bankers, you talk to ex-CEOs, ex-employees to understand what works and what doesn’t in a business.
Sam: Because I want to eliminate the uncertainty. And I’ve been thinking about this — the reason entrepreneurship is almost philosophical to me, and to a lot of people, is because entrepreneurship is about how much uncertainty and fear you can take and still continue moving forward. 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?”
The price you’re paying for potentially a big outcome — or potentially just being free — could take five 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. Dealing with uncertainty and dealing with fear.
You have fear over hiring someone when you only have $30,000 in your bank account. 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. This really has to sustain itself now. You have fear over finding your first customer and thinking, I promised them something — now I really have to work my butt off to make it work for them. You have fear over getting hate and people making fun of you. The name of the game in entrepreneurship is just: can you handle the fear? And worse — can you handle the uncertainty over potentially five or 10 years?
On Uncertainty vs. Risk [00:26:45]
Shaan: Beautifully said. Mohnish Pabrai had a good addition to this. He said: understand the difference between risk and uncertainty. He was talking about it with the stock market. Basically, the stock market hates uncertainty. If investors don’t know whether your earnings are going to be good or bad, they’ll just assume bad. You get a huge discount for uncertainty. But it’s not the same thing as actual risk.
Risk is: what do you have to lose? Uncertainty is just not knowing what’s going to happen.
And people think that entrepreneurs take a lot of risk. But I actually think you are a good example of what most entrepreneurs really do, which is: they are actual risk minimizers. How do I win while taking the least amount of risk necessary? I’m not trying to take unnecessary risks. I’m trying to vaporize risk everywhere I can. Whatever’s left over — fine. I’m willing to live with that.
He tells the story of Richard Branson. Branson is seen as this freewheeling gunslinger “Mr. Risk” type — partly because of his look, his brand. But when Branson started his airline — a very risky business, most airlines fail, most don’t even make money, razor-thin margins — he called up, I think it was British Airways, trying to get one plane. He was like, “Hey, do you have a 747?” They said, “We don’t just sell 747s to random guys on the phone.” He goes, “Can you connect me to the person who does?” They said we don’t sell 747s. He goes, “All right, do you have extra capacity in your fleet — a 747 that’s not currently in use?” They said yeah. He goes, “Would you lease one to me?”
He started Virgin by leasing the plane, not buying it. He was only on the hook for payments 60 or 90 days out, but he was already going to pre-sell the tickets. The airline business works where you sell the tickets before you pay for the plane and fuel and the actual cost of operating. He realized: what’s the worst case? I just give them the plane back. That’s all I’m on the hook for — give the plane back if I can’t follow through. But if I can get it to work, I’ll know ahead of time because I sell the tickets up front. So it’s actually a risk-reduction approach to what other people see as taking massive risk.
And I would say you’re the same way. When I’ve seen you go into a business, you’re looking to reduce risk everywhere possible. Does another business like this already exist and work? So I know there’s demand and I know the business model works. Can I apply it to a space with weak competition — not a lot of super geniuses running around trying to do what I’m doing?
A third way: you try to bootstrap it. You don’t take external investment. Can I start this with pretty much no money? So what do I have to lose? Just my time.
And fourth: can I use my copywriting skills to attract demand before I have to fulfill the service? I would pre-sell as much as possible.
Sam: Right. I would sell sponsorships before. I would pre-sell as much as possible.
Shaan: And you would do a bunch of research to reduce risk. Talk to the bankers, figure out what works in these businesses. Talk to ex-CEOs, ex-employees to understand what works and what doesn’t.
So I think you’re a master risk reducer. When somebody sees the businesses that you do, they all sound kind of random. But where you’ve come to, at the end, is: you’ve figured out your money-making skill, you figured out how to be tenacious and scrappy, and then you’ve gotten better at project selection. And ultimately, you use a risk reduction method to pick a project you think is kind of — I wouldn’t say a slam dunk, but you’re not hoping for a one-in-a-hundred outcome. It’s like, I have to fumble the execution for this to fail.
Sam: Yeah. And you should hold your breath and say “I had good project selection” because in 2015 I started a business called Itch Juice. A poison ivy treatment.
Shaan: Scratch your own itch, as they say. [clears throat] So stupid.
Business #6: Itch Juice (Poison Ivy Treatment) [00:33:00]
Sam: There was this type of lotion that mechanics used. A green scrub — I forget exactly what it was called. It turns out it had the same ingredients as poison ivy treatment. I bought it in bulk, like a barrel you’d have at a mechanic shop. It was like 20 cents an ounce. But as poison ivy treatment, it sold for like $20 an ounce. I realized I could rank high on Google. So I got into the poison ivy treatment business.
And I learned the same thing there that I had learned in the alcohol business: these short little get-rich-quick schemes you jump into without doing the ikigai preparation — without asking what am I actually passionate about — they’re stupid. I learned that one.
Shaan: 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 said, “I did it, by the way.” [laughter] It’s like, oh, I told you just don’t say anything.
Sam: Now I think I do good at selecting new things. So I got rid of that, and then I started working on other things.
It Takes 10 Years [00:34:30]
Shaan: Ten years, though. I think I have the same story — it took 10 years for me to even figure out what a good business is. I don’t know how I read about these prodigies who are so mature when they’re 26 or 27. When I was 26, 27, I knew nothing. And I actually felt this way about you — you write stuff on a whiteboard, you have these frameworks, these ways of thinking. I don’t think in frameworks. I just do.
Sam: Yeah. While I was sitting there with my whiteboard, you were out there just doing it. I was like, I have to do what this guy’s doing.
Shaan: It took me 10 years to even figure out at all what the hell was going on. Ten years. You could say that so quickly. Watch — “10 years.” That was so quick. When you’re in it, 10 years is an eternity. Especially because you don’t even know if or when it ends.
If I knew ahead of time — “it’ll take 10 years but you’ll figure it out” — it would have felt so much better. At the time, the tunnel is still dark and I don’t know if and when it ends, or how much time I have left to get there. So it feels much worse in the moment. So for anybody who’s in their kind of “decade of doing dumb stuff” arc — I feel you. It’s normal. It still works. Just keep going.
Sam: Lewis and Clark — one of my favorite stories. They were sent out from St. Louis. Thomas Jefferson said, “Hey, Lewis. Hey, Clark. Do me a favor: just walk in that direction and tell me, does it end? What’s it look like? What’s at the end?” And they just go. Back then, phones didn’t exist. Mail barely existed. They were just walking around not knowing exactly where they were going. And it took two years.
Imagine sending someone off on a trip for two years with no idea what’s going on, whether they’re ever coming back. That’s what entrepreneurship feels like. It could take two years. It could take five. Who knows? But we’re just going to go in that direction, and I pray and hope we’re going to find something. That’s what the uncertainty feels like.
Shaan: Yeah, exactly. And every year you’re like, “Now I know.” And then you say that again the next year — “Oh, well last year we were so dumb, but this year now we have it figured out.” It takes a certain amount of self-delusion to not be like, “Hey man, you’ve said that three times already. Do I really believe you this time?”
You need delusion. And I think that’s also why you have to move to San Francisco — because you’ll be surrounded by success stories. You’ll be like, “Okay, cool. That guy’s not special. I could do it. If he could do it, I could do it.” And also everybody around you is similarly deluded, which really helps. You brainwash yourselves into this mode where you’re going to keep going, keep taking shots, and 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 going to Silicon Valley.
The Small Wins: Frisco Disco, Copywriting Class, Real Estate [00:40:00]
Sam: Can I rattle off a few tiny ones? I did this thing called the Frisco Disco Taxi — we dressed up in disco outfits with afros and gave rides home to people on New Year’s Eve.
Shaan: Was this before Lyft?
Sam: Yeah, before Lyft. Or maybe like right as —
Shaan: You literally had Lyft figured out.
Sam: Yeah, yeah. Tinder too.
Shaan: Tinder too. [laughter]
Sam: 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 of failures. I bought some real estate and I learned that the way you make money in real estate is through doing the most due diligence up front and looking at tons and tons of properties, because you make your money when you buy. And that is not my skill set.
The Hustle, Trends, Events — and This Podcast [00:41:30]
Sam: And then of course I had The Hustle. The Hustle started as a conference, then became a blog, then became a newsletter — which worked. We launched Trends, which was a fairly successful product. And then we expanded our events business. Events business is horrible — the way that we did it. We had hundreds or thousands of people coming to each event. Way better to go after smaller groups and charge a lot more. But back then I couldn’t even imagine someone being willing to spend $2,000 to $5,000 per ticket to a trade show. I wish I would have figured that out.
Shaan: Yeah. And then this podcast turned out to be a business — we didn’t really realize it. I definitely started it alone. I still don’t think we thought of it as a business for the first two or three years. For the first nine months I’m almost certain it made zero dollars.
Sam: No, I had a sponsor somewhere in there. Round down to zero — yes, like 10, 20 grand.
Shaan: So I posted this photo. I want people to understand this. Shaan came up with the podcast I think in July and then I joined him in September. We did a bunch solo and then I joined later. Sometime in December — so we’re talking six months in — Lance Armstrong read The Hustle and I became friendly acquaintances with him. He wanted to use my office where Shaan and I were recording the podcast. He messaged me: “I need to use an office for a meeting. Can I use this?” I said yeah. We pulled him into the podcast as we were recording. I posted this photo of me, Lance, and Shaan — and we only have two microphones —
Shaan: And two chairs.
Sam: And two chairs. Shaan’s sitting on like the arm of my chair. During the episode, when Shaan wants to talk he has to lean in to reach my microphone.
Another episode, we had a guest call in — a digital guest. It was me and Shaan in real life, and a guest on the phone. One of us didn’t have AirPods, so we just shared one AirPod — we each had one in our ear. And I think we were recording on an iPhone. It was so janky, even six months in.
Shaan: Which was funny too because it’s not even like these were the early days of podcasting. It’s pretty late in the game of podcasting. [laughter]
Sam: Someone should go look at the old chairs we used. We picked them because there was a podcast at the time called Fighter and the Kid and they used these bright red chairs — the brightest red chairs. We figured if they use it, it sticks out on a thumbnail. And it is just a hilarious-looking set. [laughter]
Shaan: Honestly, it got to be pretty cool when we were in person together. It was pretty amazing. I wish we could be doing that — it was so good.
Sam: It would be the best. It was so much fun. We ran to Best Buy and bought a video camera and had an intern record us. The shot was just you and I, dead-on, talking. And the guys we were copying were Theo Von and Brendan Schaub — who obviously Theo is Theo now, but back then he was a cameo guest on another podcast.
Shaan: Good times. [laughter]
The Come-Up Was the Best Part [00:46:00]
Sam: Doesn’t this feel nostalgic going through all this? Because you were with me for most of it. Isn’t this kind of fun to look back on?
Shaan: Yes. When you’re in it, you just want to get out of it so bad. Like, “God, I just want something to work. Anything. Is this gonna work? I really hope this works.” I wanted to get out of it so bad. And then now — you look back and I’ve really never had as much fun since as I did on the come-up.
The come-up was a lot more — I don’t know — high variance. Unpredictable. Crazy stuff happened. Fun things 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 going to go do the hot dog stand now. But those were actually pretty fun, kind of random projects. Great stories, great photos, great memories of trying to pull it off — things you were, at the time, too dumb to know were dumb.
And now, unfortunately, you have the curse of knowledge. The further you go, the less likely you are to go try random dumb things that might actually have high upside or high fun or high memories at the end of it.
We have a lot of young guys listening who are in their 20s. Enjoy it, man. It was such a blast. It doesn’t feel that way, but I’d say with a high degree of certainty — if you do the same thing, or try really hard for 10 years and keep taking risks — Shaan and I have dozens of friends from that same era. We have seen many, many of them succeed. Not always total home runs, 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 look back and be like: it works. You just have to do it.
Sam: I mean, it sounds corny, but at the time you think your success is about how hard you’re working, your idea, your team, your execution of the individual thing. And that’s true at the project level. But at a personal level, the only thing that’s going to determine your success is basically your rate of learning. How quickly are you figuring things out? Are you adapting, learning, getting better at your next shot than you were at your last shot?
It’s the rule of 100, right? Try something 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. Looking back, that’s very much the case.
I’m sure there are people who get there a lot faster. For both you and me, it took 10 years — because we went through process of elimination and got rid of most of the dumb things. But you did do one thing differently than most people. You never made the mistake of building something nobody wanted, which is maybe the main mistake I made. I had a bunch of things that sounded great on paper — “if it works, it’s going to be huge” — but nobody even wanted the thing to begin with. You die on the launch pad.
Whereas you made the opposite mistake. Everything you made, people wanted. Whether it was hot dogs, whiskey, a way to get rid of their itch — you always made something people wanted. Sometimes the business model was broken or the scalability was broken. But you never committed the cardinal sin that most entrepreneurs make: doing something that sounds good on paper but nobody actually wants. And then spending all your energy trying to convince them they’re wrong.
Shaan: You know what’s funny? Looking back — The Hustle, I think we were at 100,000 subscribers in year one, 500,000 in year two, a million in year three or so. 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.
So you’re saying I made things that people wanted. Looking back, I agree. But when you’re in the thick of it — I remember Ryan Hoover launched Product Hunt and people were talking about his product way more than mine, and I was like, “That’s what product-market fit looks like. Not mine. I’ve never experienced that.”
And I look back and I did have it. So some of these things when you’re in the thick of it, you have to really work hard to extract the lessons in real time. There have been so many things looking back where I’m like, had I only done this I would have had so much more.
For example: I used to think I needed to act corporate to become a big company. Now I know — act small as long as you can. Or if you have something growing at 50% a year, don’t mess with it. That’s a great growth rate. I saw other people growing significantly faster but they ended up dying. And I was like, “I want to grow that fast.” Looking back: no. That was a rocket. That was fantastic. Bootstrapped. Beautiful.
I heard this line: 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 car you love — that could be an amazing life. It could actually get to the destination, but maybe a little slower. I thought being called a “car” instead of a “rocket” was an insult. I wanted a rocket and I wanted it to work. Nonsense. I wanted a car. I wish I would have had the confidence back then and learned that lesson.
Wrapping Up: Sam’s Story and What’s Next [00:55:30]
Shaan: 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 10 or 15 things he tried before that. The stumbles and fumbles on the way to success.
I’m going to do mine. We’ll do it next episode. I’ll tell you all the terrible ideas I had going up to finally making it.