Sam and Shaan run through an “awards show” of one- and two-person businesses doing millions in revenue, organized by categories: biggest, hardest to build, easiest to recreate, most fun, businesses they’d most want to own, rookies of the year, and worst of the best. They close with sharp takeaways on what it actually takes to build a mighty solo business — and why doing it entirely alone is probably a bad idea.
Speakers: Sam Parr (host), Shaan Puri (host)
Cold Open: The Window Deal [00:00:00]
Sam: I was like, “Have you done any deals I would have heard of?” And he’s like, “You know Disneyland?” I was like, yeah. He’s like, “A lot of windows in Disneyland. We do all the windows in Disneyland.”
Shaan: Oh my God. They bought a window company, got him a Disney contract.
Sam: We do all the windows at Disney.
Intro: The Mighty Business Concept [00:00:15]
Shaan: All right, what’s up. We are talking about something pretty special this episode. This is going to be different than our normal episodes, which are freewheeling, freestyling. Today we’ve got a plan, and the plan is we’re going to talk about companies that crush it with only one or two employees.
The reason we thought about this: there was some news a couple weeks ago that a company I had never heard of called Wargraphs sold for $54 million. Yeah — that’s obviously impressive, but the most impressive part was that Wargraphs was just one dude. One guy sold his company for $54 million.
Do you know what Wargraphs did? Is it a gaming thing?
Sam: It’s a gaming thing, yeah. So he built basically a companion app for League of Legends. If you play League of Legends, this was a thing that would keep track of your stats and help you get better at the game. He built this little companion app, and it had gotten really popular. I think he got to like a million players using it and was generating serious revenue. So he sold it for $54 million in cash. He was upfront about it — he said: I got half of the $54 million in cash up front, and I have the other half as an earn-out that I have to earn if it hits certain milestones along the way. Which is just super impressive for a one-person company.
Shaan: How old is the person?
Sam: I think he started when he was young, but it’s been like seven or eight years. I’m gonna guess something like 30.
But it got me thinking: everybody talks about big businesses, for good reason — big businesses are awesome. But what about mighty businesses? What about the guys who are punching above their weight? Somebody who has just themselves, or one or two people, that does millions in revenue profitably and flies under the radar. How many other Wargraphs are there out there?
So we did some research and found some, and that’s what this episode is going to be about. We’ve kind of touched on this before — we’ve done some of our most popular episodes. If you go on YouTube you’ll see the episode with Peter Levels, which has a couple hundred thousand listens. And the episode about Amit Agarwal — the guy who builds G Suite plugins, basically Google Sheets plugins. He does millions of dollars in revenue as basically one guy, a blogger turned app builder. Those were some of our most popular episodes, so I think this is going to be a good one too.
Anything else before we jump in?
Shaan: Yeah, I want to give an honorable mention. Have you listened to Juvenile growing up? The rapper?
Sam: Of course.
Shaan: So NPR does this thing called the Tiny Desk concert series — they’re in the office playing acoustic songs. Someone suggested they have Juvenile, and Juvenile replied: “WTF — what the f is a tiny desk? Hell no.” And you know what? They got him to do it anyway. This past weekend he did it, and in preparation I’ve been listening to that Juvenile concert. It was awesome. He did “Back That Ass Up,” Manny Fresh was in it — it was awesome. Awesome, awesome, awesome.
Sam: So honorable mention to Juvenile!
Shaan: Let’s call these the Tiny Desk Awards — businesses that can be run off of one tiny desk because it’s just one or two people.
Sam: And we’re going to do this like an awards show. We’ve got a long list, but that’d be kind of boring to just go through, so we’re breaking it up into categories. We each have our answer for each category. First category: biggest one-person business.
But we also have to set some rules here.
Shaan: Yes, some of these “one person” things can be a bit vague. Oftentimes it means the founder plus a team of contractors, or agencies they work with. Or in many cases it started as one person and was that way for a long time and then they hired a team.
Sam: Exactly. So it’s more the spirit of the law than the letter of the law. They don’t have company t-shirts because there’s nobody to give them to. They probably won’t have an office where a bunch of people go in. It’s either one or two people who are the core drivers — maybe they use some contractors or vendors or agencies for other things — but that’s generally how we’re looking at this.
Shaan: Yeah. So you know, they don’t have like the morale events and the all-hands meeting. It’s one or two people who are the whole thing.
Sam: Right. And so let’s get into it.
Category 1: Biggest One-Person Business [00:05:00]
Shaan: All right, let’s get into it. First category: biggest one-person business. You go first.
Sam: I’m going to do another gaming one that I doubt you know. Do you know what Stardew Valley is?
Shaan: No, what’s that?
Sam: So Stardew Valley is this game. If you look at the game art, it looks like 8-bit art — very, very simplistic. And it was made by one guy. This guy Eric Barone. He gets out of school and doesn’t want to get a job, so he’s like: I’m going to teach myself how to code. But instead of coding for coding’s sake, he decides to build a game — he always liked these games from when he was a kid. Harvest Moon, this kind of Farming Simulator game that had a cult following. He’s like: I’m going to make my version of Harvest Moon.
He spends basically four years in solitude just building this game by himself before he releases it. Did he have a job during that time?
Shaan: He just lived off his girlfriend. She had a grad degree stipend, and he had a part-time job as an usher.
Sam: An usher is a terrible job — unless you’re literally trying to be a cover artist covering the artist Usher. When you’re working as an usher, that’s not a sign things are going in the right direction for your crew.
Anyway, he launches the thing. Stardew Valley has sold 20 million copies at about $13 a pop, so it’s done something like $150 million in sales or revenue. And he’s the only person who built it — just by himself.
Shaan: Honestly, it’s not that uncommon. Minecraft was largely built the same way. There’s this guy Notch, the developer behind Minecraft — if you’ve ever seen him, he’ll get on Twitch and just stream himself coding Minecraft for like 12 hours straight, just building the game. I think Minecraft had more people overall, but one guy was really the driving force and driving energy around it for many, many years.
But Stardew Valley is my pick — $150 million off of one solo game dev.
Sam: Notch, when he sold — wasn’t it like multiple billions?
Shaan: Two, three billion, something like that. And then he outbid Beyoncé for like an $80 million mansion in LA. But he was tweeting about how everyone hates him now. He was like: “I’m so lonely, this sucks.” Still in this fancy $80 million mansion.
Do you remember that whole ordeal? He was talking about how he didn’t give equity to people, so some of the people he hired ended up hating him. He was having all these huge parties but was deeply lonely. He was just lost. He went through this whole thing on Twitter about how he hates his life.
Sam: I missed all that. He went through this whole thing on Twitter?
Shaan: Yeah, like he hates his life. But he’s sitting there in this insane $70 to $80 million house. Honestly, I remember looking at that house — it was a fat mansion.
Sam: I would love to just see Beyoncé getting the news. “Who? Who outbid me? Was it Spielberg? It must have been Lenny Kravitz — no, it was Notch.”
Shaan: All right, mine is StreamYard. I think they launched in 2019, right before the pandemic hit. It was basically a way to stream events online and stream interviews online. These two guys scaled it to $30 million in revenue in about one year or 18 months, and this mostly happened because of the pandemic. They ended up selling it to Hopin for $250 million — a mix of cash and stock.
Sam: Have you heard what’s going on with it since?
Shaan: I’ve heard the opposite of what you’re saying. After COVID, events came back in person — which is naturally going to hurt the business. They had massive layoffs. And I heard the founders took a lot of secondary — over a hundred million in secondary.
When you hear those three things together: massive layoffs, the crazy event that was driving your growth has stopped, and founders took huge secondary — it’s usually because the business is going in the wrong direction. People don’t complain about secondary when the thing is exploding.
Sam: I heard the other way around. I also thought that, but I heard the other way.
Shaan: We talked about StreamYard right when they were getting going, and then again when they were acquired. I think I met them — back when I was doing video streaming I met kind of everyone in this space. I do know they got to $14 million ARR when it was just the two of them, and then got to $30 million when they’d hired up a team. So this is kind of a hybrid — they got really far with just a couple of people and then hired up as they scaled before they sold.
I remember going to their website when it was just them. The founder was on the homepage giving a tutorial video. It was just him, practically holding the camera on his lap. He looked exhausted. He looked so worn out. I remember this during the pandemic when we were thinking about using them for something. He looked super haggard. But it’s very impressive that these two guys built something that sold for $250 million.
Another big one — this happened a long time ago, so I have no connection to it: Plenty of Fish. How much did Plenty of Fish get acquired for?
Sam: Like $550 million.
Shaan: Yeah. Started by one guy named Marcus, who I now see online — he seems to just live the most lavish life and does crazy stuff. Plenty of Fish was basically one of the early dating websites. Like OkCupid, but I think predominantly Canadian. That was probably the biggest exit I’ve ever heard of for a really small, small team.
Sam: That guy — the Plenty of Fish founder — isn’t he a bit of a character? I feel like that’s a whole other episode we should do one day.
Shaan: I think so. I haven’t researched it enough to actually verify the claims, but I’ve heard little grumblings, little stories that something weird is going on. I don’t know the truth though.
Also, I love the fact that you met the StreamYard guys and they looked haggard — and you’re like, it’s like in Silicon Valley when you see somebody like that, you put your arm around them: “Hey, you all right? Is it too much traction or not enough? I just need to know how I’m going to help.”
Sam: If it’s too much traction: “Come here, sleep on my couch, let me feed you, just take this check, put me on your cap table.”
Shaan: Yeah. One out of ten of the haggard people are getting beat down by too much demand, and nine out of ten are just being beat down by not enough demand. You just need to know which one it is.
Sam: If there’s too much demand: “Come here, sleep on my couch, let me feed you.”
Shaan: Exactly. Put me on your cap table.
The Abner / Twitter Trending Story [00:15:00]
Shaan: Who else have you met like that? I remember you talking about a guy named Abner.
Sam: Yeah. I met him after the fact, but he told me this story and it stuck with me. I was in a car with him in Ethiopia for four hours — there was nowhere to run. So I’m hearing this and I’m like: all right, go ahead.
So Twitter started taking off in popularity right when it got going in Silicon Valley — it became a thing. Abner and his team were kind of data science types, and they’re like: what can we build that makes Twitter work better? Twitter was such a simplistic product at the time, almost like a protocol — anyone could build apps on top of it or use the data.
He’s sitting on a train, starts coding this thing. He’s like: “Oh, I’ve done this research on sentiment analysis.” And right when he said that, I could feel my channel start to drift. I was like: is there anyone else in this car I could talk to? But I’m in a car in Ethiopia. There’s nowhere to run. So I’m like: all right, tell me more about your PhD and sentiment analysis.
But he’s like: “You could figure out how people are feeling about a certain topic because they’re talking about it in a certain way. But then I realized — actually, what I’ll do is, instead of figuring out their mood, I’ll just figure out what they’re talking about a lot more than usual. That’s kind of interesting.”
And he basically created trending — for Twitter, off Twitter.
Shaan: Oh cool.
Sam: So he’s like: “I can figure out that the word ‘Olympics’ is normally said this much, but right now it’s being said 10 standard deviations more. That means Olympics is trending — it’s above par.” He creates this and builds a separate website off of Twitter — I forget what it was called exactly — and they start getting millions of hits on it. They’re basically drinking from the Twitter firehose, trying to keep both sites running.
Eventually Twitter buys them, so they become like employees 10 through 20 or something.
Shaan: Oh, nice.
Sam: At the time Twitter had the fail whale — the service was constantly going down because it had so much usage, and it was Web 2.0, not yet scalable. They hadn’t figured out how to scale it. He told me: for six months, he just woke up every day with the imprint of his keyboard on his forehead. He’d passed out working, would wake up, not even know where he was, and just keep going. Six months straight. He said: I’ve never experienced anything like it.
And at the time I remember thinking: there are levels to this thing. That’s what it feels like when you really have one of the winners. If you talk to people who were early at Facebook — when you’re inside one of these generational companies at the early stage when they’re scaling too fast — it’s like when people talk about living in New York. They’re like: the energy, you can’t explain it. That’s what it was.
Shaan: Dude, that’s exciting. I love those old stories. I always read those old books like The Hatching Twitter and all that stuff.
Sam: Me too. All right, next. Let’s skip a category and come back to it.
Category 2: Highest Degree of Difficulty [00:21:00]
Shaan: Let’s go to highest degree of difficulty — the hardest example, the one where you’re like: how the hell did you even do that? There’s no way anyone else would have done this. You go first.
Sam: All right. It’s called TinyWow — the URL is tinywow.com. I met this guy through Hampton. His name is Evan Gower. He had another website called TechJunkie — they just talked about tech topics, a pretty normal content site — and he ended up selling it for eight figures. On the side he started this thing called TinyWow, which is a bunch of tools: how to convert a PDF, image editing tools that use AI. It’s one of those sites where you Google “convert this file to PDF” and he’s able to come up first.
Right now it has 6.6 million visits a month. The reason it’s interesting: it only does $20,000 a month in revenue — because, as he says, I haven’t turned on any of the monetization yet. He’s just got some light ads. He goes: I’m going to turn it on eventually, but right now I’m enjoying the summer with my family. I just haven’t really dug in and built it out.
Shaan: Evan wasn’t talking about the weather, put on AdSense! What are you doing?! This is insane, dude.
Sam: That’s the cool part about these one-person businesses. This is another guy who’s said the same thing: I felt like taking the summer off, so I just let it ride for a while.
He basically had a history as a developer, though he says he doesn’t do any development now. He has a team of one contractor overseas who helps him build and implement things — Evan basically just draws and designs. The reason the site took off: do you remember those TikTok videos that say “here are five websites that should be illegal, they’re so good”?
Shaan: Yeah.
Sam: That’s basically how it got popular. Getting 6.6 million visits a month mostly from social is very challenging. We’ll see if he’s able to turn this thing on.
I asked him: how big can this get? He said: I think of Canva. I think it can make tens of millions of dollars a year in revenue — we have this traffic, we can have a feature that says “hey, you can edit this picture using our platform and we’ll charge a small fee.” He thinks this can actually be a big business. But right now it costs $10,000 a month to run and it’s making $20,000 a month in revenue. That’s the current state.
Shaan: Do you know how much remove.bg makes?
Sam: Oh, that was the old way. It’s like if you need to remove a background from an image — cut out the object, remove the background — remove.bg was the go-to. Super quick. You drag your image in, it removes the background, boom. They started charging for things like high-res exports and removing the watermark. I’m sure this thing crushes.
Shaan: Yeah, 50 to 60 million monthly visits. And then Canva acquired them. So you can probably dig through Canva’s numbers — I think Canva just went public last month, actually.
Sam: Wow. That’s crazy. That’s so much traffic.
And TinyWow started in 2019. The company behind remove.bg — I think it was Colido or something — started in 2019, sold in 2021, two years later, for roughly $100 million.
The reason I said these are the hardest to make: getting that scale of traffic that fast is so challenging. There are a lot of software products we’re going to name as one-person companies, and that’s challenging — you have to put in a ton of hours, you have to invent stuff. But getting traffic to me is more of an intellectual challenge where I have no idea where to start. Whereas with software, I’m going to make this one feature, then this other feature, talk to my users — it involves a mix of luck and skill. Getting a lot of traffic to your website early on, I think fewer people know how to do that. That’s why I think this is one of the harder things to start.
Shaan: My pick for highest degree of difficulty is Photopea. Photo P — basically, one guy recreated the entirety of Photoshop in a web browser, for free. Photoshop is one of the most complicated products in the world. He recreated it by himself, gave it away for free, and made it work in the browser — which Photoshop doesn’t do. You have to download the app.
It’s just remarkable. The guy barely monetizes it. Doesn’t want to sell it. If you go search “Photopea Reddit” or look him up on Hacker News, he goes and talks about why he built it, how he built it, how he thinks about it. It’s pretty insane.
Traffic-wise: about 13 million monthly visits according to SimilarWeb. At the time he posted about it, he was doing $100,000 a month off literally the most basic ads — a simple banner ad on the site. He did a post on Hacker News — April 11, 2021 — and he goes: “Hey guys, I’m Ivan, I’m the creator of Photopea. I made almost a million dollars in the last 12 months. 90% from ads, the rest from premium, which is basically useless — you pay to hide the ads, so it’s not even much of a premium. When you start your own project, you never know if it’ll make $250,000. But if you get hired, you can be quite sure you’ll never make more than $250,000. That’s why I started it.”
I don’t know exactly how big Photopea is now, but depending on how many users it has, I could see this getting sold for nine figures — over $100 million.
He did an AMA on Reddit and someone asked: “Have you hired your first employee yet?” This was a year ago. He says: “After I did my first AMA on Reddit, lots of great people got in touch. I did end up hiring one guy from Prague who went to my university. But it’ll take some time for him to get familiar with the code.” It’s pretty crazy how this guy operates.
Sam: Why do you think this is the most challenging?
Shaan: Technically, recreating Photoshop feature for feature is absolutely insane. And making it performant in a browser is not easy either. For one person to do this — I think it’s crazy. That’s just an insane endeavor.
Sam: That’s insane. The cool thing about these one-person companies — but also the downside — is that everything relies on you. You don’t have anyone else to ask for help, you can’t hire anyone, you can’t have anyone better than you doing something because you’re the only person.
This guy says he put 7,000 hours into it before he made any money from it. That’s insane. I don’t understand how he could grind that hard for that long with all that pressure on him.
Shaan: It’s like when you go to someone’s house and they’re like, “Oh do you want to see my model train set?” You’re like, “Sure, why not.” They take you to the basement and they’ve recreated the city of Vienna, and they’re just tinkering on this one thing. You’re like, “How many hours have you been doing this?” And they go: “Oh, I just come here every night. I love it. It makes me feel so good.” And you’re like: holy shit. That’s how I think about this guy.
Sam: I’m not that type of person.
Shaan: I’m not either. I envy it. That’s amazing willpower.
Sam: Do you remember Viral Nova? It was a guy named Scott DeLong — basically an Upworthy clone. The content was like: “Here’s a list of 10 reasons why you don’t want to go swimming after eating — you’re not going to believe number seven.” That kind of thing. And this guy would talk about how it was just him writing 10 articles a day, and the pressure of all that traffic and success was killing him. He felt so worn out all the time. I don’t understand how some people can sustain that for a really long time — like this Photopea guy.
Category 3: Easiest to Recreate [00:34:00]
Shaan: Let’s do the opposite end: easiest to recreate. Which of these one- or two-person businesses are the easiest to start?
Sam: Mine would be anything that sells information or services. Broadly: course creators. You and I know a bunch of these people — we’re both those people. We make hundreds of thousands to millions of dollars a year from a course or two, and I think they’re fairly easy to recreate.
Another one is Design Joy. You know what they do?
Shaan: A design subscription, basically?
Sam: Basically, yes. The way he positions it sounds really hard to imagine that’s the truth, but it’s just this designer that you pay thousands of dollars a month for and you ask him to make small changes to design-related stuff. He claims it’s just him, and he claims he does about $100,000 a month, so around $1.2 million a year. You buy a subscription plan — four or five thousand a month — and you get one request at a time. You say “I’d like this design thing done,” and he turns it around. It’s cheaper than hiring a full-time designer in the US.
I think that’s the easiest to recreate. But also the worst to run, which we’ll talk about later.
Do you know any other course people doing like — I know Sam Evans does $10 million in revenue, $5 million in profit, and for a while it was just him. I’ve met these people.
Shaan: Yeah. I met a guy recently who does a product management course. I was like: oh my God, who’s taking a product management course? He goes: no, no — it’s how to ace your job interview as a product manager. How to get a job as a PM at one of these tech companies.
He was doing something like $2.5 million a year in revenue. Probably 80% margins or so. What they’d do is give away free content — how to get a job as a PM, how to interview, how to prep, what it’s like talking to a Facebook PM — to get you on the email list. Then they pitch: “Hey, do you want to actually get a job as a PM? That job pays $120,000 a year. Buy this course, join this cohort.” A couple thousand dollars for a course that’s going to help you get a job that pays over $100,000. Very simple value proposition. And it was just three PMs who got together and built the whole thing.
Another easy one I think I mentioned before: Cyber Leads. The URL is getcyberleads.com. It’s a newsletter by this guy named Alex West. It costs somewhere between $400 and $1,000 a month depending on what you get. He goes and hand-picks different companies that have recently raised money and, based on a bunch of attributes, he thinks are about to hire an agency. Then he emails this list out once a month to agency owners with the contact info, who’s managing ad spend, whatever — you can just contact them directly.
He’s got my face and a quote as a testimonial on his website.
Shaan: Do you use it?
Sam: No, I don’t use it. But I talked about it on the pod like two years ago. Said it was so freaking simple, the value’s so clear. He uses that quote. I’ve never used it. But he sure used me.
Shaan: He was a big fan. Is there anything you can do? Can you say anything about people who do this?
Sam: I talked about it on the podcast. I said it was simple. He uses that as a quote. I guess I could decide to take them down?
Shaan: You can always do that.
Sam: Anyway — selling information. Anything that sells information, that’s the easiest thing to start.
Shaan: I went the same route, but I want to give more detail. When you tell somebody “selling information is the easiest way,” they’re like — cool, what do I do? So let me break it down a bit further.
You know this guy Lenny? Lenny Rachitsky, or something like that — something along those lines. I think he used to work at Airbnb as a growth and product guy. He’s got Lenny’s Newsletter, Lenny’s community, Lenny’s job board. He was basically like: I’m going to put out tons of free thought-leader content on a super niche topic that only certain people are going to care about — but they’re going to care a lot. And that’s kind of the key with this stuff: how do you put out free content to establish yourself as an authority in a niche, so you can then monetize through consulting, a job board, a paid community, or a paid newsletter?
That’s the formula. Design Joy does exactly this — he puts out free design examples, then says: hire me for design. Lenny does the same — he puts out really good stuff like “how did these 10 huge marketplaces get their first thousand users?” He goes deep, interviews them, gets the real answer on the specific zero-to-one question that’s highly relevant to other people going through that same challenge.
Sam: He’s got a podcast too. At one point his job board alone was doing a couple hundred thousand in revenue. I’m sure the newsletter does a couple hundred thousand in sponsorships, at least annually. And I’d bet those are minimums — probably way more. I know at the beginning his job board was crushing. I don’t know what they’re doing now, but I’d bet his entire roll-up — job board, newsletter sponsorships, podcast, paid community — what do you think Lenny’s total is? Two million, three million?
Shaan: Yeah, for sure. About two to three million a year. And he did that in something like two and a half to three years. He kind of appeared on the scene — I’d say two-ish years ago — and obviously you have to know your stuff. He spent a decade being awesome inside these companies in order to be able to do it. So I don’t mean to make it sound overly simplistic. But there are people who did it without that background too.
Shaan: Another example: Harry Dry. One of my favorite content creators in the whole world. A guy I’ve tried to recruit like a hundred times to do something with me — I feel like he’s made to do something great. He keeps putting me off, but he’s going to say yes eventually.
He’s got Marketing Examples, this great blog. I don’t know exactly how much it makes. I’d guess between a quarter million and half a million as just him making content. He’s very young. He didn’t do the “put in 10 to 15 years at a company, become an industry expert, cut your teeth, then go make content” route. He’s like: no, I’m pretty sure I can just look at what’s out there, give my opinion on it, and it’ll work. I’ll study this stuff, and that’s how I’ll do it.
And that’s how I feel like a lot of people can do it. You can be the curious novice approaching these topics and become an expert just by studying them intensely. Anyone could say: I’m going to study what makes TikToks go viral, become the expert at breaking down viral TikTok content, and then brands are going to know me as the person they should talk to about TikTok consulting or advertising on TikTok. Build your niche audience and niche authority in that space. Harry Dry would also be one of the easiest to recreate — not because he’s not talented, he’s super talented — but I think that’s something anyone can do.
Sam: A lot of people are trying to do this with AI right now. But what’s interesting is that both Lenny and Harry were both early-ish. There were others talking about that type of stuff, but they both felt early when they were talking about it to this community on this platform. Both got popular on Twitter right before the pandemic. I remember seeing Harry in 2018, 2019.
So timing matters for a lot of these things. Speaking of which — that Facebook Threads thing. No idea if that’s going to be a thing or not, but that’s an example of: hey, there’s this new thing right now. If you want nothing to lose, you better be there.
Shaan: Yeah, just go get in there and see what’s going on. That’s one of those things people did with Clubhouse too. I don’t know if that worked out in the end, but the idea is right.
Sam: The way I say it is: most entrepreneurs are actually surfing waves. You don’t get to create the wave, but you do have to paddle out. You have to be on your board in the water — that takes effort. Then you wait. Sometimes it’s a dud. Sometimes it’s a small wave and you paddle back out. But when you catch a good one, that’s when you find out how good you are at surfing. You might wipe out the first couple times, but that’s your job as an entrepreneur — paddle out, be out there, start trying to catch these waves, get a sense for where the big waves are, and how not to wipe out when you find one.
Shaan: So this episode you’re giving a really in-depth surf analogy. Last episode you gave us a fat pitching analogy — fat pitches, right?
Sam: If you ever played baseball — which I did, I was starting right fielder for my high school team. Which, anyone who knows baseball knows that means you’re the biggest scrub on the team. That’s who they put in right field — the ball never comes to right field. But did you play baseball?
Shaan: In China? No. I went to high school in China.
Sam: Hey, it’s a different experience.
Category 4: Most Fun One-Person Business [00:43:00]
Shaan: All right, most fun. The one that seems like the most fun to work on. I’ll go first.
Joe Rogan. I’m pretty sure Joe Rogan’s media enterprise is bigger than all the late-night talk shows combined. Forget the Tonight Show, Letterman — Letterman’s been retired for 10 years. Jimmy Fallon, whoever — his audience is bigger. He’s made hundreds of millions doing it. And I’m pretty sure it’s just him and Young Jamie.
I’ve heard from a few friends who’ve been on it how it works: it’s Jamie who produces it, Joe, and then one other guy named Matt. Matt sends Joe a list of like 30 people they can get. Joe sometimes just ignores it, and every once in a while says, “That person and that person.” That’s all he says. Just three people.
That’s amazing. Most people think: oh, Joe Rogan, he’s just a podcaster. Yeah, he is a podcaster — but that thing is a media juggernaut.
Spotify paid him hundreds of millions to be there for a couple of years. Before that, just off the sponsorships and off the Alpha Brain product he built around the podcast, Joe Rogan was doing incredibly well. I think he has the most fun of probably anyone on the planet. He took all of his hobbies and made them his work.
He likes UFC: he’s the UFC commentator, sitting ringside, analyzing the fights — but he only does it for the ones in Las Vegas, an hour flight from him. He doesn’t do any of the ones that require a bunch of travel. He does all the best ones, none of the worst ones.
He wanted to do stand-up comedy: he does stand-up, sells out theaters around the country, makes people laugh for a living. He does this podcast where he says: I’m going to have conversations with the people I want, for as long as I want. People were like, “Joe, three hours is too long.” He said: that’s the type of conversation I want to have, so I’m going to do it my way. And it worked.
He just dictated how he wants to live life, on his own terms. If you have a thing that does $100 million a year in revenue for multiple years — you know, it’s not apples to apples, but traditionally that’s a billion-dollar property. You can’t really sell “The Joe Rogan Experience” because you need him — it’s tightly branded with him. But let’s say he’s built something worth at least $100 million, because it’s generated $100 million of profit for him. A multi-hundred million dollar business built with a very small team.
And he’s got this new thing called The Comedy Mothership, like a mile from my house in Austin. There’s always a line out the door to get into that place.
Sam: Why not? It’s a comedy club. If you drive by at six o’clock, every single night there’s been a line out the door to go there. It looks awesome, right?
Shaan: Yeah. Joe Rogan just dictated how he wants to live life on his terms. I think he has the most fun of probably anyone.
Who you got for most fun?
Sam: All right. So scroll up to the top of this doc — I put a link in here. I don’t want it to sound like I’m promoting Hampton, but I had to prepare for this episode and I went through our database and pulled people. We had just written a blog post about this guy.
His name is Joseph Mambra. He started a company called GymStreak. This guy is super fascinating because he has all the attributes of what a lot of these tinkerers have. He’s from Zimbabwe, moved to England when he was about 12 or 13. That was the first time he ever experienced the internet. He taught himself how to code, taught himself design, then launched this thing called GymStreak.
At first it was just an app for tracking your workouts. Then what he did: he got his buddy to wear one of those motion capture suits so he could do 3D visualizations of exercises — hundreds of them. The app is free to use with a premium tier. You track your workouts, he uses AI to suggest what weights you should do for the next workout based on previous performance. And if you don’t know what an exercise looks like, there are hundreds of 3D models showing you how to do a proper bicep curl, whatever.
In year one — 2021 — he did $300,000. Year two, $2.5 million. His goal: in the next two years, get to $15 to $20 million a year in revenue. He’s the only employee. He told me he got most of his users from Facebook and TikTok ads, hired a consultant and an agency to help him learn how to do that, and now he runs them himself. He also said: I’m taking the summer off right now, so my growth this year might still only be $2.5 to $3 million — but I don’t feel like buying ads or staying on top of that right now. We just had a kid.
It’s super fascinating to see a guy who came from Zimbabwe, didn’t use the internet until he was 12 or 13, taught himself everything. In that blog post you can see pictures of him arriving from Africa, learning how to use a computer. Pictures of him with his iPhone and laptop at the gym, filming people doing curls so he could use AI to get the 3D imaging. Really fascinating company.
Shaan: Love that story. Good for him. That’s really, really cool.
If GymStreak can get to $15 to $20 million a year in revenue like he thinks, that would be a monster business for one person.
Category 5: Business We’d Most Want to Own [00:52:00]
Shaan: Next category: business we most want to own. I think this is specifically a good question for us because a business we’d want to own would be the lowest-maintenance business — neither of us wants to run an extra business right now. So it’s like: which business would you want to own because it’s very much autopilot?
Not Design Joy — that’s a subscription where people are paying you and you’re providing work. Not a course or content business where you constantly have to create new content to stay relevant and get more customers.
I think we’ve got the same one. You explain it.
Sam: Milled.com — m-i-l-l-e-d.com. Really simple website. It’s a compilation of email marketing that different companies send. If you want to see what your competitors are sending for their Fourth of July sale, you go to Milled, search the brand, and you’ll see: here’s what Ridge Wallet sent for their Fourth of July email. You click it and you see the exact email — the design, the offer, the copy. You use it to get inspiration for your own email marketing.
This one guy built the site — I don’t know exactly how long ago — runs it as a side project, does a million dollars a year on it. He posted on Hacker News about it and said: I was doing email marketing for a brand. I noticed two things. One, it took us several days to create each email blast. Two, I had to subscribe to dozens of other competitor newsletters just to do research. My hypothesis was: I could create a site that signs up for all the brand newsletters and makes it easier for anyone trying to do email marketing.
That’s the core pitch. He’s just been running it as a side project. Doesn’t take much maintenance. He could do nothing on it for a while and it still makes money.
He makes money through display ads on the left side of the page. But here’s another way he makes money: if you’re a marketer, you go to Milled, you see a shoe brand ran this campaign, you read the email, get inspired, and click through to the shoe company — that’s an affiliate link. If you buy the shoes, he gets a cut.
Shaan: This is a horrible way to monetize. This is a really amazing product with an under-monetized website. Good for him for getting the traffic in the first place, but that’s a horrible monetization model.
Sam: I agree. But I think the guy just doesn’t care. He’s like: this is easy, low maintenance. That’s why it’s in my “want to own” category — low maintenance and a lot of upside left.
Shaan: I’ll do one for businesses I’d want to own. Anything that’s kind of marketplace-y — because sometimes if you do it right, the community kind of handles the business. Built with.
BuiltWith was started probably around 2015 or 2016. It’s like the most niche thing ever, but it’s a really big niche. You go to BuiltWith to see which plugins and technologies a website is using. WordPress, Shopify, whatever. And also — Shopify started with just WordPress, I think, but now it covers both. If you see a website you like and want to know what they’re using — their checkout, their CRM, their email tool — just go to BuiltWith, type in the URL, and it tells you everything they’re running.
It has something like tens of millions of people going there a month. When I first found them around 2020, I think they were doing $14 to $15 million in revenue with just one person. I think that would be a really cool company to own — super valuable once you have all that traffic and those people coming back to you consistently.
Sam: Yeah, I’ve been using BuiltWith for a long time. It’s kind of like a data index, right? More like a database than a marketplace in a way.
Shaan: Exactly. But I agree — it’s pretty amazing.
Category 6: Rookie of the Year [01:00:00]
Sam: All right, let’s keep going. Rookie of the year — a new one we found.
Shaan: I think you might have already covered yours.
Sam: I did, but this Joseph Mambra / GymStreak guy — I love his story. I take a lot of pride in finding people before they’re really popular. I think this guy’s going to be a winner. Read the blog post I have linked from the Hampton site. It’s really good. That’s my Rookie of the Year.
Shaan: Mine is OnlyFinders. So OnlyFinders is a search engine for OnlyFans. If you want to find a certain type of creator on OnlyFans — you know, whatever you’re into — you search on OnlyFinders and it gives you a ranked list of top profiles for that category.
I’ve been down the OnlyFans rabbit hole — I think there’s a lot of potential in businesses around that ecosystem, and this was one I found. OnlyFinders is run by one guy. He’s awesome. He listens to the pod. And he crushes the SEO game for OnlyFans.
What he did was smart: he didn’t just want to rank for general searches like “best OnlyFans” or something like that. He wants the high-intent ones. The person searching for something very specific — like, I don’t know what people search for, but say, redhead. If you go to his site and click the button on the right, it shows you the top searches. He ranks really high for the specific categories that are clearly people’s things. Those are really high-intent searches.
Then on the other side, he goes to OnlyFans models and agencies and says: if you want more traffic, I have tons of people searching for exactly your thing — pay me per click for every person I send to you. He basically recreated Google. A search engine where you get paid per click to send someone with high intent to a specific destination.
And here’s the thing that makes this even more interesting: OnlyFans does not have a discover section on purpose. They decided they don’t want to be in the discovery business — they want to be the underlying tools underneath these creator profiles. So there’s a gap there, and he’s filling it.
He’s just been surfing the growth of OnlyFans, which has grown exponentially. OnlyFans a few years ago was very small. Now it’s bigger than Twitch. It’s bigger than some of these massive websites. The curve is unreal. And it generates billions in payouts to creators. If you can be part of that ecosystem, it’s really valuable.
Sam: I’ve now met multiple people on OnlyFans that you’ve never heard of — women doing between one and two million dollars a month on their profile. Their body is the COGS, so it’s basically all profit. Some of them, as they get bigger, have an agency managing the account.
Shaan: What are they doing with that money?
Sam: Just huge income. And how long can they sustain it — three years, five years? And it’s funny, some of them will just sell their name, likeness, and photo library when they’re done. They burn out and say: you run it, just give me 50%. It’s like what Bruce Springsteen did — same thing.
Shaan: This is insane. The engagement on these things is wild. If you have an OnlyFans business, reach out to me at shaanpuri.com. I want to invest in OnlyFans businesses that are just pure cash flow.
Sam: Are the creators cool? Like, when you met them?
Shaan: The problem is these businesses are very hard to sell and very easy to kill — so they need strategy around that. But to your question about the people — yeah, they’re nice people. I don’t know much more than that. I talked to them, they’re just people.
Sam: You said you hung out with a couple of them?
Shaan: I just talked to them. Yeah, they’re nice people.
Sam: That’s insane. How did you even get in touch with them?
Shaan: It’s the internet. How many times on here have I talked about OnlyFans? People basically start emailing — oh, you’re into that, here’s what I do. When you see a big line at the front door, you don’t wait in that line — you find a side door. The side door is generally some dude who listens to our podcast who runs their business or manages their account.
Category 7: Worst of the Best [01:07:00]
Sam: All right. Last category: worst of the best. These are all cool businesses, but which one is our least favorite to run?
Shaan: Yours is going to be OnlyFans, no?
Sam: I mean, it would be — but I already had something else.
Kevin Van Trump. So Kevin Van Trump — I met him in 2018 at a conference. He’s like six feet tall, really big guy, very large. He walks up to me with this super thick accent: “Hey, what’s up, man, how you doing?” Just starts talking to me. He’s talking about my newsletters, The Hustle, all this stuff. He’s wearing a Ramones t-shirt with Converse. He just looks like a Walmart guy.
Then he drops a line — we were talking about art — and he says something like, “Oh yeah, that Picasso, I got one of them.” I let it slide. Then I go: “How many subscribers does your newsletter have?” He goes: “Oh, about 60,000.” And then he goes: “Hey, how much do you guys charge for yours?” I say: “Oh, it’s free, we make money on ads.” He goes: “Yeah, we charge like $300 a month.”
I do the math in my head. That’s $18 million a year. He goes: “Yeah, something like that. I don’t even know.”
I start hanging out with him more and he’s got this newsletter called Kevin Van Trump — he talks about agriculture and how it impacts commodity prices. He’s brilliant. He sounds like just a thick Southern accent guy, but the man was a Wall Street trader. He lives in Kansas City and he’s got custom-built motorcycles in the back of his house, all these Picassos. Killing it.
But that same day — we hung out, got dinner — at 8:30 he goes: “Hey man, I gotta run, I gotta write tomorrow’s newsletter.” I was like: what? He goes: “I do it every day. Six days a week, 2,000-plus words. It’s really long.” And he’s been doing it for 18 years. Almost 20 years, every day.
He was making all this money. I don’t think I would trade lives with him though, just to have all that money.
Shaan: I had the same answer. I think he’s amazing. You put me onto him. I met him and his son — such awesome people. So fun to be around. Smart, really nice, kind people. No pretense whatsoever.
Sam: And same thing at FarmCon — he was hosting FarmCon, which is like the biggest farming conference get-together. So fun to be around, smart, really nice, just kind people. No pretense.
I went because Sam told me about him and introduced me. I go to Kansas City — was it awesome?
Sam: Yeah, it was amazing.
Shaan: I’m there and it’s 11 at night, the whole event’s done, everyone’s at the bar. Every single person is drinking a beer.
And he’s like: “I gotta get up, I gotta go back to my room — I gotta write tomorrow’s edition.” I was like: wait, you’re still writing it yourself? And he’s like: “Yeah, I write it. I’ve written it by hand every night.” And he started this thing more than 10 years ago — like 18 years ago. Almost 20 years every day.
And it’s not some cookie-cutter “here are three links” thing. It’s: Powell came down and said this, and he said that, and here’s how this is going to affect corn futures, and here’s what I’m betting over here. Deep market analysis for crops and commodities. Then a bunch of memes. And he’s like: “Nope, never do ads. I just wanted to build as much trust as I could in this community. I charge for it and I never advertise. That’s why we have FarmCon — everybody shows up because I built a lot of trust over the years.”
I learned more about business from that guy in one hour than I did in my entire four-year education at Duke. He said a bunch of things I loved.
One: the content’s cool, but he goes — and he just said it so matter-of-factly — “Being an investor is the best job in the world. It is the best job in the world. There is no better job.” And you sort of think about that and you go: okay, if that’s true, how do you architect your life to get there? Because he’s basically saying: this newsletter is great and makes a lot of money, but I wish I was just an investor. It would have been a better choice.
He’s also been pretty good at investing. He said: I was early into Bitcoin. I was early into Facebook. We started hearing about Bitcoin at FarmCon around 2013, 2014. I didn’t buy until 2015, 2016. I should have been in right when I first heard it. Same thing with Facebook. He said: here are two lessons I learned in investing.
Number one: the best trades are the ones where you buy them, put them in the drawer, and never think about them again. With Bitcoin — I bought it, put it in the drawer, heard all the news, didn’t care. It’s in the drawer. I was going to let the 10-year bet play out.
I was like: “in the drawer” — that’s a cool concept. What investments can you have the conviction to just put in the drawer, say I’m not going to react to the daily news cycle, I’m going to let the 10-year play out?
Number two: you always get a second chance to get on the train with the best investments. The price will come back down — that’s your chance. Most people spend the whole way up wishing they’d gotten in earlier. Then when it crashes, they’re too scared to buy because they feel like: is it over? Did it pop? And then you lose either way — you buy high and you don’t buy low. That’s a recipe for being poor.
He said that also happened with Facebook. It went up, then crashed to $19 on the public market. He got back on the train. The train came back around, and he got right back on.
He said: you want to figure out how to override the psychology that most people have. When it’s going up, you wish you had gotten in earlier. Then when it crashes, you’re too afraid to buy because you feel like: is it over? Did it pop? Did I miss it? Was I wrong? And so you lose twice — you don’t buy on the way up and you don’t buy on the way down. Buy high, don’t buy low. That’s a recipe for being poor.
Sam: This guy breaks every stereotype. You think he’s just some hickey guy from the country. Turns out he knows way more about Facebook and Bitcoin than you do. He’s brilliant. And I love hanging out with him and his friends because it teaches you: I’m an idiot for judging people a certain way. These guys are all badasses. And they’re fun as hell.
I did a call recently with another guy from FarmCon — same sort of person. White guy, maybe early 50s or so. I wasn’t sure if he was super rich, because so many of those guys are super rich. The guy who introduced me to him said: yeah, this guy’s worth $300 to $500 million personally. I was like: wow, okay. That’s crazy. Because I’d been like: does he actually make money on these deals? Does he have a track record of success? And he was like: yeah, he does.
So this guy’s got phrases for days. I keep a document on my phone called “phrases” — whenever somebody says something that’s just funny or worded really well, something punchy that sticks, I write it down. At FarmCon I filled that thing up, there were so many good ones.
This one guy — I don’t want to put him on blast by name — he was at a private dinner at FarmCon, and people are doing introductions around the table. I’m like: “I’m Shaan, I work in tech,” basically dying inside during my own introduction. This guy stands up and goes: “I don’t know who won the World Series. Can’t tell you how to get six-pack abs. Hell, I don’t even know where the remote is in my house. But I know one thing — I know how to structure deals. And today I’m going to tell you about a deal I’m doing.”
Sam: What an incredible way to introduce yourself.
Shaan: Then he’s talking about his age, and someone says: “Cut him in half — there’s going to be a lot of rings.” Amazing.
Then I did a Zoom call with him. I had just finished my workout and my trainer was insisting I do some myofascial foam rolling at the end, like rolling out. I’m like, I gotta be on this call. He says: just do it while you’re on the call. So I turn on the video and I say: “Sorry if this looks weird, I’m doing some stretching.” He immediately goes: “Okay, cool. If it looks like I’m stretching, call 9-1-1 — because I’m having a stroke.”
Sam: Why would you even take a call like that? But that line, immediately ready — I was blown away.
Shaan: Incredible. And then I asked him: “Have you done any deals I would have heard of?” And he goes: “You know Disneyland?” I go: yeah. He goes: “Lot of windows in Disneyland. We do all the windows in Disneyland.”
Sam: So what does that mean — cleaning the windows?
Shaan: He bought a window company, got them a Disney contract. They do all the windows at Disney. This guy is incredible.
Sam: What state does he live in?
Shaan: Tennessee, I think.
Sam: What the hell is a “deal struck”? I don’t even know what that means.
Shaan: He does private equity. He buys companies. He’s like: “I just know how to find a great deal, how to put the financing together, and how to structure it so I get maximum value out of these deals.” That’s basically what he does.
What’s yours for worst of the best?
Sam: I had both Design Joy and Kevin Van Trump. Because of the time thing — I love that Kevin Van Trump has built this amazing power niche in the farming industry, but I wouldn’t want to be the person who has to write the newsletter every night. The pressure of having to get it out every morning. I felt that during Milk Road for one month and I was like: nope, not doing it this way.
Shaan: Although if I was him I’d just find a way to hire somebody to do that. I can’t believe he hasn’t done that yet.
Sam: Does Ben Thompson still do his daily thing?
Shaan: Oh yeah. Ben Thompson. He does Stratechery and every day he writes a newsletter about basically the same four topics — Facebook, Google, Amazon, Apple, Netflix — and what’s going on in their business and strategy. These are so long. He does this daily long-form and his audience has the highest bar — the smartest people in the tech industry, VCs and founders, reading him every morning. So he has to come with original, super smart content about the same topics he’s been covering for like a decade. He makes roughly three million dollars a year doing this and he only charges $120 a year. I think it was $100 and he raised his price to $120.
He writes from Taiwan. Every single day.
Sam: That is the worst. That is absolutely the worst.
Shaan: I literally don’t know how he does it. If someone told me they were going to do that, I’d say: what are you saying? This makes no sense. And he does it every day. Ben’s awesome — I don’t beat this as a knock, I’m just saying I would hate the pressure of the daily super-insightful thing. Original content, every morning, about the same like 10 companies. I don’t know how he does it.
Sam: Yeah, I would never want to do this. So what do we think — I want to know what listeners think about this. Do you think going all-in depth on one topic, doing this award category style, works? Or not?
Takeaways: What All These Businesses Have in Common [01:22:00]
Sam: Can I give some takeaways? I don’t think we covered those.
Shaan: Do it.
Sam: Here are my quick takeaways.
The most common industries where you see one- to two-person businesses that crush it: thought leadership on social media — just putting out free content on social media. E-commerce — we didn’t do any e-commerce examples in this episode, but there are a bunch of e-commerce businesses that could do a million dollars a year in profit run by one or two people. Agencies for everything else. Games — we talked about Stardew Valley, Minecraft, there are a bunch of games built by one or two people. Apps and plugins on top of existing platforms — a Figma plugin, a Google Sheets plugin, a Gmail plugin. And data aggregators, like BuiltWith — basically compiling data so you go search and find what you want because they’ve aggregated everything. Milled is the same thing. OnlyFinders is the same thing — it’s a data aggregator.
Strategy-wise: you need to be either amazing at distribution — you’re the influencer, the content creator — or amazing at product — you’re the guy coding the game, and you’ll hire a publisher for distribution. If I was going to try to make this happen, I’d ask: where can I be either incredible at distribution or incredible at product? Put all my emphasis on that one thing.
Second: you need attributes. A lot of these we’ve made sound simple, but you’ve got to have some skill — copywriting, design, coding, investment judgment, market analysis. You have to get to master-of-your-craft level if you’re going to do this.
Third: it’s all about leverage. The way a one- or two-person company gets to millions — or tens of millions, or hundreds of millions — is leverage. You need code: build it once and it runs as software. You need media: podcasts, newsletters, content. Or you need capital. You’re not going to use labor the way most companies do — that’s why most companies have hundreds of employees. If you’re going to skip that, you’ve got to use these other levers: code, capital, or media. Figure out which one you can use and build around that.
Shaan: And the beauty of it: because of the internet, if you’re the best at X, you now get to sell to the whole world.
Take Miss Excel — we didn’t give this example during the episode, so I’ll throw it in now. This is a girl who goes on TikTok and in a high-energy, dancing way teaches you how to use Microsoft Excel better. She’s the best in the world at teaching Excel. It turns out the best teacher of Excel knows how to do the useful stuff and can dance. That’s what the best teacher of Excel looks like. And she now gets to teach the entire world Excel. The best of anything gets to provide that product, service, or education to everybody. That’s the beauty of the internet. You need to figure out how to become the best at X, and then just make it available to everybody.
Sam: The last thing I’ll say — and I think this is important — it’s lonely. The best times I have in work — whether it’s a shitty day or a great day — are when I’m in the trenches with coworkers, or celebrating with them. These solo jobs are lonely.
I’m actually surprised when I hear about how they’re able to push themselves. I push myself because I have mouths to feed, or because I want to be held accountable to other people and make them proud. It’s really hard to push yourself this hard and to think big when you’re by yourself. It’s just hard to do this every day alone. Hopefully you have a good spouse or significant other or something, because it’s just challenging.
When I started, I wanted to be a solopreneur — they call it a “solo capitalist.” I raised a fund and I was like: I want to be a solo capitalist and just invest by myself. And very quickly I was like: this isn’t fun at all to do this by yourself.
Shaan: Yeah. And not only is it not that good to do things by yourself — a little bit of help goes a long way, and a complementary person who’s good at the things you’re not good at is really, really useful — but on top of that it just ain’t no fun. Most of life is the journey, not the destination. You don’t want a shitty journey for this awesome destination.
Very quickly I was like: this is a duopreneur thing. It’s me and Rameez doing this, and I’m going to do it in fun. Even my econ business — I gave a chunk of it to a guy who was smarter than me and had done this before. Why? Just because I don’t want to be reporting into myself, only have myself as a thought partner, sparring with myself on ideas about this. I want to have somebody awesome just to do some idea jousting on this.
Doing it by yourself is honestly a terrible idea. You should definitely try to get one other person to do this with you. I think two people is the sweet spot where you get the most autonomy, the least management headaches, you still get the most stuff done, and you have a lot of fun along the way.
Closing [01:30:00]
Shaan: All right, that’s the pod. This is an experiment for us — doing a few focused, themed episodes. Today’s theme was these one- or two-person businesses that crush it.
Do you like this format, or do you like the freestyle?
Sam: The freestyle’s a lot easier. This one took a lot of work. I stressed out for so long doing this. These are emotional for me.
Shaan: We’ll see what you think. If people love this, you’ve got to go to the YouTube comments and show us if we should do more of these or not. We’re cool either way, but this is an experiment — so let us know in the YouTube comments.
Whether you’re listening on iTunes, Spotify, or whatever — go search “My First Million” on YouTube and go to the comments on this video and let us know. We’ll read them and see. That’s it.