Sam and Shaan discuss the steel-manning technique and how Peter Thiel uses it, trace common success paths (speech and debate, hardcore gaming, arbitrage), and explore niche internet businesses like RockAuto and ManualsLib. They then debate the creator economy and WorkWeek’s business model, with Shaan arguing the talent paradox makes it nearly impossible to build lasting value, before closing on personal timing, free agency, and a Dane Cook growth hack story.
Speakers: Sam Parr (host, co-founder of The Hustle), Shaan Puri (host, founder of Milk Road)
Intro Banter and Peloton Philosophy [00:00:00]
Shaan: Solving for demand problems suck. Solving for technology problems rocks.
Sam: So we have two things going on. The first is we have a new intro philosophy. Have you ever watched a Peloton class?
Shaan: Yeah.
Sam: They always do this thing — I don’t even do Peloton but I’ve seen two or three, so I’m gonna say always. It’s always like, “All right everybody” — they come in like they were just having the best inside joke with somebody. They’re like, “Okay, we’re gonna start with the ghost star. What’s up everybody, Jamal here and we are gonna rock!” It’s like they always start with this laughter to make you feel like: we were having such a good time, you’re in a good place right now.
Sam: Okay, so here’s the deal. We’ve got a couple things happening. The first is last month we did a contest where people reviewed us and we gave out… was it a thousand dollars? Did we give five thousand? Six thousand dollars to six different people?
Shaan: Oh wow. So six people won a thousand dollars each?
Sam: Yeah. We even gave it to two or three people who gave us negative reviews. If you’re watching on YouTube, click the link and you’ll go to the end of this episode — that’s where you’ll see the names. You have to contact Ben if you’re one of those people.
Shaan: By the way, the people commenting on YouTube get a bigger prize, which is that me and you go and reply to everybody who comments on the YouTube channel personally.
Sam: They talk shit? Yeah, especially if they talk shit. I like the comments. There’s really two that I like — when they say “great episode” I don’t know what the hell to say back, so I just say “yeah, thanks.” But if they talk shit, or if they reference some inside joke or call us out on one of our mannerisms, those are great.
Shaan: It makes me uncomfortable when that happens. I get self-conscious.
Sam: To summarize: yes, we announced the winners at the end of a different episode. We’re going to link to that clip in the show notes of this episode. Click there, listen, see if you were one of the winners. If so, email Ben. What’s your email, Ben?
Shaan: bwilson@hubspot.com.
Sam: All right. Now the second thing — this is actually significantly cooler. We are giving away five thousand dollars to two fans. Here’s what you have to do: take our content, whether it’s audio or video — it’s all on YouTube — and remix it. Chop it up into little viral clips, then use the hashtag MFMClips on all the popular social media. We’ll find you. We’re gonna do a combination of cool stuff and popular content, and we’re gonna give away five thousand dollars to two different people.
Shaan: There’s somebody who did this for the All-In podcast. There’s just a TikTok channel somebody created called All In Talk, and they just chop up clips from the pod and put them up there. No contest — it’s just a fan account — and this account is getting hundreds of thousands of views because the content’s already good. All you have to do is grab the best thirty-second back-and-forth. Not everything hits, but definitely one per week is hitting and this account is getting huge.
Sam: If you just did that — if you just made the TikTok account for MFM and put the best nuggets on there — your account’s gonna get popular, which is more valuable than the five grand we’re giving you. Whoever does that consistently, we’ll just employ you. And yeah, we’ve talked about doing this every month. If someone’s good at this, we’ll give you five thousand dollars a month. Maybe. That’s in the cards.
Shaan: The hashtag is MFMClips. Instagram, TikTok, Twitter — we’ll follow it all. The right thing to do is take something from a podcast like this and find the best rant, the best back-and-forth, the thing where we’re yelling at each other — those will hit.
The Noah Kagan Podcast Debrief [00:07:00]
Sam: Shaan, I got a bunch of stuff you want to talk about. Did you listen to the Noah Kagan pod?
Shaan: I listened to it, yeah. In the car. It’s great because I normally never listen back to this pod — it’s awkward to hear your own voice — but this was different. I got to basically hear an episode of MFM with somebody else on the other side.
Sam: What’d you think of it? Before I give you my take.
Shaan: I didn’t think it was that good, actually. I thought it was good, but the flow was awkward. I don’t know if that’s just how the podcast sounds when we’re on it too, but there was something very start-stoppy about it. The topics were great — I liked the stuff you guys talked about — because it hit the thing I always want: I felt like these were just two cool people I would be friends with, hanging out, and I got to hang with them. It didn’t feel like a show. You’d just be like, “Do you have a will?” and he’s like, “Yeah, I got one, but I don’t have kids so I put in my brother’s kids.” And you’re talking about shit that, like, just dudes would talk about. That was good. But the start-stoppy thing bugged me.
Sam: I think there was maybe a weird delay, because it happened consistently. I’d say something and there was just this weird pause, like “oh, I’m sorry, you go ahead.”
Shaan: We have the opposite problem — we talk over each other, but that actually makes it flow faster. It’s just whatever, I’m talking over you, you’re talking over me, let’s keep it going. Versus waiting like: “Okay, you go, now I go.” That’s the problem with Zoom pods in general. In-person is just so much better because you can start talking over each other and that’s a normal thing in a conversation. You can interrupt each other. But if you interrupt someone on Zoom it’s very abrupt — it kind of stops the flow of everything.
Sam: What did you think of the Peter Thiel stuff?
Shaan: That was cool. Some of the nuggets — I don’t know if they’re all real. Does he really have blacked-out Mercedes waiting outside the building with the engine running and the jet fueled on the runway at all times?
Sam: That’s what the book says, so I was quoting that.
Shaan: I liked the poker story where he bought in at the tournament, then had to go meet with Zuck, came back, and asked for his money back. That should be a clip, by the way.
Sam: Those are the nuggets that make you feel like you kind of get to know the psyche of somebody. We already know the resume — you don’t need to talk about what Peter Thiel has done. You’ve got to talk about what it’s like.
Peter Thiel, Original Thinkers, and Steel-Manning [00:13:00]
Sam: I’ve told this story — maybe not on the pod. I met a guy in college who was friends with someone who worked under Peter Thiel at PayPal. Friend of a friend. The intern gets invited to go to Peter’s cabin at Tahoe, like a vacation with twenty people. He gets there and the first question Peter asked him was, “How much money do you have?”
Shaan: Peter Thiel asked the college kid that?
Sam: Yeah. The kid is like, “None, basically. I have a checking account at Wells Fargo.” And Peter goes, “I don’t care how much you have, but whatever you have you should invest in a company called Facebook.” This is back in 2005, 2006 maybe. Peter was the main investor in Facebook at that point. The kid is like, “Okay, maybe, but I’m not comfortable just investing all my money in it when I just met you.”
Sam: Every question Peter asked was very thought-provoking or reaction-provoking. And that’s something I’ve heard from many people who’ve met him: he has pretty much zero interest in small talk. He’s looking for original thinkers. He’ll ask you a question and hear you, and if you’re just saying the same stuff everybody says, he mentally buckets you as “this person is not going to give me original thoughts.” But if you have original thoughts, he doesn’t really care about your pedigree or your accomplishments — you’re in the circle of people he wants to talk to.
Sam: Which goes back to the famous Peter Thiel interview question: “What’s something you believe that few others would agree with you on?” He’s looking for the secret — what do you think is true that others don’t? That question filters for people who have unique insights.
Shaan: I’ve also noticed he does another thing that’s actually pretty interesting, and I think it’s one of the reasons he’s hated by a lot of people. He’s shockingly open-minded almost to the point of seeming stupid. Like when he supported Trump, people were like “what are you doing?” And I heard his explanation and I was like, that’s logical, but my emotions feel this way so I just can’t go along with it. He was very logical about it.
Shaan: He does this thing where when he answers a question he says, “Well, a lot of people believe this, and then other people believe this, and some people believe that.” He presents both sides of everything.
Sam: I heard you say that on the pod and I was like, “Oh, I have something I would add to this conversation.” Because that’s actually a technique. Have you ever heard of steel-manning?
Shaan: No.
Sam: Do you know what straw-manning is?
Shaan: Yeah.
Sam: Straw-manning is when you’re debating somebody about something, and you kind of pigeonhole their view into a really weak version of their argument so you can knock it over easily. Like a man made of straw — you could just blow a gust of air and it falls right over. So it’s like saying, “Well Sam, I know you think everybody just needs to close their eyes and put their money into a Vanguard ETF no matter what.” That’s not actually my argument, but if you make that weak version of my argument, it’s really easy to contradict.
Sam: That’s what most people do — when there’s something they disagree with, they present the straw man, the absolute weakest version of that argument, so they can knock it over. What the smartest people do is the opposite: steel-manning. Even when they disagree with something, they’ll go into it and say, “People who believe X would say…” and they’ll make the strongest possible argument for that thing. It’s an in-good-faith way of figuring something out.
Sam: So the straw man example — say you disagree with Trump supporters. The straw man is, “They’re just racist people who hate Mexicans.” The steel man version is: “Some people’s top priority is their economy, especially if they live in states like Ohio and Michigan that have been decimated by job losses. They see Trump as willing to invest in their jobs, which could actually be really great for X, Y, Z reasons. Although he says things that are offensive to certain groups, the pros outweigh the cons for them.”
Sam: Steel-manning is: how do you understand the other person’s viewpoint and actually build their argument stronger than they could build it themselves? It doesn’t mean you have to agree with it — it means you’ve presented the strongest case on both sides, and then you decide which one is more correct. I think that’s a legitimately life-changing lesson. And I think Peter Thiel does that — he steel-mans both sides of the argument and then decides which one he believes is correct.
Shaan: That’s a good one. Other smart people I know do that too. I’m gonna start doing that. I didn’t know what it was called — I don’t know too much about logic and formal arguments.
Success Paths: Speech & Debate, Hardcore Gamers, Arbitragers [00:22:00]
Sam: Give me one other thing I’ve been observing. People who grow up doing speech and debate in high school or college — I’m just noticing that’s a common thread among successful people I know.
Sam: I’d say there are like three or four really common success paths I’ve identified when I look at a whole bunch of successful people I’ve met. This cluster of people all had that same experience. One is speech and debate — this comes up most often with entrepreneurs, investors, or salespeople. They’re able to just really effectively tell their argument.
Sam: When I did the episode with Hasan Minhaj, the comedian, I was like, “You’re like me — an Indian kid growing up. Stand-up comedy isn’t usually the career choice. When did you figure out you wanted to do that?” He goes, “I went to a Chris Rock show and as soon as I saw it — I was a speech and debate kid in high school — I just saw it as humorous speech and debate.” He has a stance he has to take, like a comedic premise, and all it is is supporting arguments that ladder back up to re-support that premise at the end. Except the supporting arguments can be humorous rather than literally true.
Shaan: I said on this podcast before — I think my speech and debate class in college was the only effective class I ever took.
Sam: Oh, you were one too? I didn’t even know that. That makes perfect sense.
Shaan: And the really good part is when they make you argue about stuff you don’t actually believe in. In debate you don’t get to choose the thing you already agree with — you’re assigned it. You’re going to argue for this thing whether you believe it or not. So you have to get good at steel-manning that argument basically.
Sam: Okay, speech and debate is one. I’ve traced another one: hardcore gamers. People who get really freaking good at video games — competitive, or just complete obsession. If channeled properly, that same type of person uses the same kind of strategy, cooperation, grinding mindset, ability to understand the rules of the game and then find the shortcuts, the hacks, the glitches to get the infinite money hack.
Sam: I know a whole bunch of people who got super successful in crypto and they all came from this RuneScape mafia. It’s basically a bunch of dudes who used to play RuneScape and trade in the arena. They’d go farm, get some virtual goods, and flip them — they were digital flippers. That same group of people is really good at crypto. They were early, they figured it out early, they were good at poker too. The same skill set applies.
Shaan: These are ironic because if your parents saw you doing it, they’d say, “What a waste of time, go learn something useful.” When in actuality the skills you build gaming are so applicable later.
Sam: There was this thing recently — I forget exactly what it was — but it was some kind of protein-sequencing or DNA problem, something incredibly hard. Some medical board couldn’t figure it out for a decade or two. They put it out to gamers and turned it into a game. They solved it in three weeks or something like that.
Shaan: No way.
Sam: Yeah. Like, all of the world’s problems — peace in the Middle East — just give it to gamers.
Shaan: We both invested in Synthesis School, which is basically teaching kids through games. It’s a riff off Elon Musk at SpaceX — he designed a school for his own kids called Ad Astra. The premise is kids learn more when they’re having fun and engaged. Nothing is more fun and engaging to a kid than a game. When they play the game they will learn all the necessary skills and strategies to win it.
Shaan: They spun that out as Synthesis School, now available to anybody, making a few million dollars a year in recurring tuition revenue. The application process is a game. I played it. I couldn’t even beat it — the game an eight-year-old is supposed to beat to get into the candidate pool. There’s no instructions. It’s you versus a computer, dots on a screen, you make a move, the computer makes a move. Eventually the computer wins and you’re like, “Okay, I’m supposed to get to the green dot.” And your brain is just fully locked in.
Sam: There’s actually an AIDS-like virus — scientists couldn’t figure out the structure of a protein-cutting enzyme for a decade or two. They set it out to gamers and they figured it out in three weeks.
Shaan: Even Ethereum — I don’t know if you know the founding story. Vitalik Buterin was a hardcore World of Warcraft player. He’d gotten to level 60, the max at the time, and earned all this stuff. Then the game maker changed the rules — changed the way items worked, and some of his character’s items he had worked so hard for just got taken away. He was inconsolable for three weeks. He couldn’t believe it — the game maker owned the items, not him. They could just change the rules and rug-pull you at the last second.
Shaan: Ethereum is basically this global computer where users own their own tokens, their own items, their own private keys. There’s no company that can do that to you. The whole platform is designed so the app makers could never rug-pull you. He credits that as a pretty major influence in his thinking.
Sam: I never heard that story.
Shaan: So what’s the last archetype or two?
Sam: Arbitragers. These are people who love the action. You’ve probably met a bunch who are like, “Yeah, I got my start doing affiliate ad networks, sending traffic to, you know, questionable sites” or “I realized I could drop-ship this t-shirt and get a ten-point vig just in the arbitrage between this ad network and this retailer.” They learn internet marketing at a very fundamental level. And at some point they get disillusioned — “Okay, I’m just sending clicks to Plenty of Fish and making seven dollars per click margin. What am I actually doing here?” Could I apply the same skill to a brand I create? To a product I genuinely believe in? To an education app I make? And they go on to do some pretty great things.
Sam: Teachers is another one. I met Jack Ma — I don’t know if you know that story.
Shaan: When did you meet him?
Sam: In college. There was this trip organized called Kairos — the top 100 college entrepreneurs. It was a total horse-shit situation, honestly. We applied the night before. They didn’t know anything about us. We got in because they needed a quota of a kid from Duke. Just to show you how fake the world is — we got into this “top 100 entrepreneurs” thing, the event took place at the New York Stock Exchange, Bill Clinton came to speak, CNN showed up. I got on CNN pitching my sushi restaurant as like the next big thing. They ran it as “college breakout success.” No — I just happened to be in front of a camera and CNN was filling airtime. No quality filter.
Sam: But at the end of that event, they said: through our connections, we got the CEO of Alibaba to pay for all of us to go to China for a week, all expenses paid, to hang out with him and see their headquarters. So I got to go with Jack Ma.
Sam: And Jack Ma tells the story. People were asking what are the keys to success, and he goes, “In China, there are two successful CEO types.” Can you guess?
Shaan: Teachers. Teachers is one. He was a teacher.
Sam: Yeah. Military — correct?
Shaan: I don’t know how you knew that. That was amazing.
Sam: He was like: military — the rigor of operations that you need in business. There’s no better training than the rigors of military. So any manufacturing business in China, the best leaders are ex-military. And for the non-factory type businesses like Alibaba, teachers tend to do pretty well.
Sam: We said, “Why?” He goes, “A teacher is one of the only professions where the success of the student matters more than the success of the teacher.” In management, that is the best principle for breeding great managers: if your success was not in how high you climbed, but how great your people became.
Shaan: I can’t believe you’ve never told me that story before. You got to go meet Jack Ma — that’s actually badass.
Sam: There were some crazy stories there. But we’ve got other stuff we should talk about.
RockAuto: A $100M+ Hidden Business [00:37:00]
Sam: Let me tell you about something. Go to RockAuto.com.
Shaan: Rock Auto — like auto, like car. Okay.
Sam: I’m on a Craigslist-looking-ass site. What is the traffic?
Shaan: This is a Sam Parr classic find.
Sam: This company is called RockAuto. I was listening to an MMA podcast — Michael Bisping’s podcast — and he does this ad read: “If you’re buying car parts, go to RockAuto.com. They’ve got every car part you could ever want.” I’d never really heard of an auto parts site other than Napa and the famous one. I went to this website because they were sponsoring a bunch of podcasters and it’s the most bare-bones site I’ve ever seen.
Sam: I was trying to do research and there’s close to nothing about them online — a few articles from five, six, seven years ago. Started by two brothers in Michigan. Over a million parts. The traffic, according to SimilarWeb, is north of 20 million monthly.
Shaan: Oh wow.
Sam: And look at the traffic source — mostly all direct. People just typing in RockAuto.com. So these guys must be something that car repair shops go to order from, or just customers ordering themselves.
Shaan: It’s meant for individuals — just guys who are tinkering. If something broke on your car and you want to replace the little part yourself.
Sam: Do they inventory parts themselves?
Shaan: No. What they do is they connect with dozens or hundreds of suppliers and have this intricate system of distributors all over the country. Their goal is to have at least one part for every car you could need — kind of like how Bezos said if a book exists, we should sell it.
Sam: I was thinking about this for a few reasons. With e-commerce, what doesn’t Amazon crush it in? They don’t crush it in hardware. HomeDepot.com is the fourth or fifth largest retailer in the world and hasn’t gotten hurt much by Amazon. And auto parts — for cars or motorcycles — same deal. There’s this company called RevZilla that was acquired for around 500 million dollars — they sold motorcycle gear and parts.
Sam: I looked up the CEO of RockAuto. He looks like Jeff Bezos before Bezos got ripped.
Shaan: Like the before photo.
Sam: Yes. It’s amazing. The problem with this business is you’d have to have so many SKUs. If you just go to BMW — cars going back to 1939, every model, every part for the cooling system of a 1939 BMW. It’s incredibly hard to manage. But what’s interesting is I don’t think this is a demand problem, which is cool. Solving for demand problems sucks. Solving for technology problems rocks. It’s far better to figure out how to build a better mousetrap than to figure out if mice are going to go into the thing.
Shaan: You want to be supply-constrained, not demand-constrained.
Sam: Exactly. And to get popular you’d crush SEO. You’d sponsor a lot of YouTubers. I’d think they have to do at least 100 million in sales. I’d bet they don’t spend any money on marketing other than maybe sponsoring some car shows. Virtually all their traffic is coming from search and direct.
Shaan: Amazing. Great find. Props on that one.
The Fitness Hotel Idea [00:46:00]
Sam: What’s this hotel thing you’ve got?
Shaan: Okay, I’m gonna start a hotel. Not today, definitely not today, but soon. Let me explain.
Shaan: I went and met with some Olympians the other day. This guy who’s an Olympian in track and field — he heard I liked running and asked if I wanted to get dinner. I went and got dinner with him and like eight of his athletes. He was an Olympian and now has an agency with about 41 track and field athletes. Not really popular for most people, but for me it was cool — I knew who they were. A triple jumper, a miler. I was talking to them about money and they don’t make anything. Some of them have little Airbnbs on the side, or bought a car to put on Turo. One of them is an American record holder. One won a gold medal.
Shaan: I started thinking: if I wanted to pay one of them to be my coach, I bet I could get them to do that — they can’t be that expensive.
Shaan: You know how the UFC has the Performance Institute? They built these state-of-the-art UFC gyms where athletes can go train. I’ve only heard about it but I’m like, I want to go there, I want to work out there. Do they have a hotel? I would love to stay there.
Shaan: I think I could create a hotel or a large piece of property where you go just to train and work out with competitive athletes. I think I could convince the competitive athletes to live there most of the year as a training base — they do a camp in the morning, train for the rest of the day, and get paid to do it.
Sam: My brother-in-law Aaron — the OG listeners remember him — he loves jiu-jitsu and combat sports. He’s created this thing called Bali Fight Club. It’s almost exactly what you’re talking about. He’s like: a lot of people want to go to Bali, be on a beach at a resort. So he found a spot with a bunch of little villas — you’re on the most beautiful beach, private villa, a chef cooking for everybody, each family or resident gets their own villa. And then the best trainers in the world for combat sports are often in Thailand, so he got a pro boxer, a pro Muay Thai guy. They’re coming on the trip too — they want a vacation also — and they’ll basically train the people.
Sam: “You get to train like a pro athlete trains: two-a-days, massage in between to recover. We’ll treat you like a pro athlete, while also being on vacation.” The whole thing is like five or six grand. This is live — he’s got two people signed up and he’s waiting until he has eight, and then the trip happens.
Shaan: I’d do getaways first, then eventually I’d acquire a piece of property within an hour of a major international airport. In the US — Austin, probably, because Austin is becoming a hub for health nerds. Maybe California, Boulder, or somewhere in Florida.
Sam: Yeah, that’s a cool idea. The getaway is a great MVP. Easy, builds momentum.
ManualsLib: Another Hidden Cash Machine [00:53:00]
Sam: Let me tell you one more thing. It’s called ManualsLib.com — the ultimate manuals library. A website that’s just full of manuals.
Shaan: Oh, this is great.
Sam: Like, I’m assembling something, I don’t have the manual. I need to fix something, I don’t have the manual. It’s just there. My KitchenAid — yes, it’s on there.
Shaan: The way you find out if a business is interesting: if they make money through advertising, scroll down, click “advertise with us,” and find out the numbers.
Sam: According to their media kit, they get at least 16 million monthly uniques, of which nearly 90% is from search. They’ve got around 3.8 million products with 5.2 million manuals, 106,000 brands, and 3.2 terabytes of data indexed. They just have every manual — they scan it and SEO the hell out of their rankings.
Sam: But it gets more interesting: I cannot find anyone on LinkedIn or anywhere online who mentions these guys or works there. I found one person who listed themselves as a freelancer based in Europe. That’s basically all I saw.
Sam: Their main competitor is this company called Owner IQ, which owns ManualOnline.com. Owner IQ is a weird business — they sell data to retail stores or brands that somehow helps them figure out who’s buying their stuff. And they do well over a hundred million in revenue, and ManualOnline is one of their products.
Shaan: Is that nutty? This is wild. And if you look at their traffic, they really grew starting in 2012 — shot up the rankings almost instantaneously, within the year, became an ultra popular site.
Sam: These types of businesses just print money. It’s ad-based, so you’re looking for a manual, and they’re trying to get you to buy something else because you don’t want to deal with fixing this thing.
Sam: There’s this company called TechTarget — publicly traded, market cap is whatever, but they do nine figures in revenue. TechTarget owns websites like CFO.com, SecurityDocs.com, TechGuy.com. Basically: if you’re the CFO of a 5,000-person company and you’re the decision-maker for buying, say, QuickBooks instead of some other software — that’s a 10-million-dollar-a-year product decision. TechTarget creates CFO.com with news hoping the CFO reads it while deciding, captures their email, and sells it to QuickBooks and their competitors. It’s rooted in influencing what you buy.
Shaan: The manual one is a little different because that assumes you’ve already bought the thing. So I guess the monetization logic is different. But yeah — these are great little secret jam businesses.
Sam: When Andrew Wilkinson came on, we asked him what type of business he wants to buy. He said a “New Zealand business” — a business that is just independent, sustainable, doesn’t rely on Facebook ads or some paid channel that could change any minute, won’t be competed against by Google, Facebook, or Amazon. They’ll never care to compete against this.
Shaan: RockAuto and ManualsLib are both New Zealand businesses.
Sam: I think they’re cool. TechTarget is in Newton, Massachusetts. RockAuto is in Madison, Wisconsin. ManualsLib is in Croatia, apparently — I can’t find a thing about them.
Sam: I feel like there’s a business you can create here. What’s new? What’s a new thing where you need manuals? Maybe software, though software is maybe not new enough. Or you could go vertical — any professional search. What does only a dentist search for that’s really obscure but really important to them? Maybe tools, software, equipment manuals, prescriptions. Some people have tried to create a separate Google for doctors because doctors Google everything. But I think the easier play — though less valuable — is figuring out how to rank at the top for everything a doctor would search for and becoming the definitive authority for some profession. Car mechanics, dentists, doctors, insurance agents, real estate agents — anything where there’s a lot of searches and nobody’s created the definitive central repository.
Dental Digest and Niche YouTube Creators [01:02:00]
Shaan: That’s a perfect segue for what I’m about to say. Speaking of dentists — I was reading about the top creators on YouTube this year. Number three for most popular YouTube Shorts creator is called Dental Digest.
Sam: Wow.
Shaan: Description: “satisfying dental reviews, dental education, and dental lifestyle content.” This kid’s got 6.1 million subscribers on YouTube, only doing dentist stuff.
Sam: Is that ridiculous?
Shaan: His about page says he’s a third-year dental student who wants to help you discover your best smile. He’s represented by Night Media — that’s the guy Reed who came on the podcast, who also represents MrBeast. Number six on this list is also a dentist.
Sam: What is going on?
Shaan: Dental content must just be interesting for non-dentists. That’s the only explanation. He’s not doing like tooth-pulling videos — I think he’s reviewing products, doing designer toothbrush reviews. Eight million views.
Sam: So weird.
Shaan: The world’s funny. We’ve identified dentists, manuals, auto parts — we’ve talked about so much stuff in a short amount of time.
Sam: What do you want to do?
Shaan: Let’s wrap it up. Let me think — okay, let’s do the WorkWeek creator economy thing.
WorkWeek and the Creator Economy Critique [01:05:00]
Sam: So I saw that Adam Ryan — I think that’s his name — he used to be president of The Hustle, sort of. He led our sales team, he worked for me.
Shaan: He was kind of like your number two guy at The Hustle for a period.
Sam: He left, went and did a couple things — some education thing, I don’t know exactly what happened. He came out with a new company recently called WorkWeek. Give me the simple description and I want your honest opinion.
Shaan: WorkWeek.com. It says “a new kind of media company.” “You want to follow people, not institutions.” So it looks like he’s scouting creators who have their own niche newsletter — like someone doing a healthcare newsletter, someone covering fintech, someone covering cannabis. They were already creating content. He brings them all under one umbrella, gets the rights to their content, and in exchange gives them distribution and money — that’s my guess.
Sam: What’s your honest opinion? You know media better than anyone.
Shaan: A few things. The way it’s positioned now, it looks like it’s just an ad agency, which in itself isn’t horrible — “we represent these creators, here’s ad inventory.” But the hard part is the creators they represent are nobodies. Maybe they’ll be somebody someday. But right now: the cannabis newsletter, the healthcare huddle — I’ve never heard of any of these people. The healthcare guy has 500 followers on Twitter. So there’s basically no ad inventory to sell.
Shaan: I think it’s going to be a very hard business. I would never raise money for this. It could potentially make money, but a few perspectives.
Shaan: First, I don’t love “a new kind of media company.” Anyone who positions themselves that way is positioning only to other media people. That’s not who your customer is. Just jargon — easily fixed, but a mistake.
Shaan: From a creator’s point of view, I think the whole creator economy thing is incredibly overhyped.
Sam: Tell me what people are saying about the creator economy that you think is incorrect.
Shaan: People are saying it’s this new economy, that now anyone with a voice can make a living. That’s true in that more people than ever before can do it, but the ratio who are going to succeed is still really small, and I think it should be small. Only the best should survive. And the best likely don’t need you. They wouldn’t be silly enough to sell you their IP or their content. No one would be crazy enough to do that — it’s the whole reason why Call Her Daddy bailed and started their own thing.
Shaan: It’s a paradox: the ones you can acquire you don’t want, and the ones you want you cannot acquire because they’re too savvy. Or you acquire them early, bet on them early, they do in fact blow up — and then they’re like “I’m leaving,” and you have no recourse. You bet everything on this creator, this personality, and when they leave you have nothing.
Sam: There’s a reason why none of the multi-channel networks worked. MCNs — one big one was called Maker Studios, I think that’s what you’re referring to.
Shaan: Yeah. They had a fantastic exit to Disney. The business wasn’t really working but they timed it well — Disney bought it before the truth came out. And then the business kind of fell apart.
Sam: Good for them.
Shaan: Right. So they timed it well. But the truth is now, what happened on Twitch is a perfect case study. Ninja became the number one gaming star in the world when Fortnite became the number one game. He was making 30 million dollars a year between fan revenue and advertisers. This team that had bet on him — Luminosity — they basically acquired commercial rights to his channel early on, when he had no following. Like picking up the option cheap. This guy’s talented, he could become something someday.
Shaan: But sure enough, Ninja was like, “Hey, Luminosity, I’m not sharing revenue with you.” And they’re like, “But the contract—” and he’s like, “I just don’t think that’s fair. If you want to enforce this, you can, but I will drag you through the mud. Every new player will know that ninja is so unhappy with you.” Luminosity sat quiet and took the L. They didn’t get the upside of their great bet. Then he goes to Loaded, the talent agency that had all the top streamers, and sure enough he’s not with Loaded anymore either. Same thing with DrDisrespect. You’re competing for these stars and the next agency will do it for less.
Shaan: The talent wins. It’s like what’s going on in the NBA right now.
Sam: This business — can it work? Yes. But it depends on your goals. If you want a tech company or a VC-trackable thing, I wouldn’t go this route. It’s going to be a huge headache.
Shaan: One of my biggest fears is starting something in the prime of my youth, when I have the most energy — for most people that’s their 30s and 40s — and going down this path and looking back after toiling for five years going, “We should have done something else.” I think there are potentially other opportunities even in this space that are better.
Energy vs. Wisdom, Timing, and Personal Free Agency [01:17:00]
Sam: There’s a graph: energy starts high in your 20s and goes down over time. And I don’t mean just physical energy — the amount of energy you can put toward your work. You get married, a little less time. Kids, less time. Other responsibilities come up. When I was in my 20s I used to work 15 hours a day. I slept in the office 200 nights one year when I was 24, 25. Max energy. Now I work on average five hours a day.
Sam: But then wisdom goes up, judgment goes up, skill goes up. In your 30s the lines cross — it’s the highest energy you’ll have while you have some good wisdom and judgment. In your 40s wisdom keeps going up but energy goes down.
Shaan: And my point is: we’re in this crazy world where if you want to work in the creator space, there are a few routes. A lot of people are creating little pieces of software to sell for five, ten, fifteen dollars a month to creators. I don’t love that. Nine out of 10 times — 99% of the time — those businesses fail. Look at the difference between a Buffer, which is a five-dollar Twitter scheduling tool that plateaued, versus HubSpot or Hootsuite that scaled way beyond that because they were selling the same category of tool but to a much larger market. The thing we’re recording on right now — Riverside — charges maybe twenty dollars a month to podcasters. It’s hard to imagine that business ever getting to 50 million in revenue.
Sam: Very hard.
Shaan: So I think of creators and I’m like, man, that’s gonna be really hard. If you just want to make a lot of profit early on without hiring a lot of people, the ad route could work. But if I was in this space I would totally look at the markets.
Luck of Timing and Free Agency [01:23:00]
Shaan: This brings me to one thought I didn’t want to bring up because it seems disconnected, but you kind of tied it in nicely. There’s a certain luck with your timing — with the timing of your free agency.
Shaan: I thought about this with basketball. Every year the salary cap changes. Every seven years they renegotiate the overall deal between players and owners. There was a time in the late 90s where players could get 200-something million dollar contracts over seven or eight years, no limits. Then owners got wise and capped the maximum at five years. Whenever you become a free agent is your moment to negotiate.
Shaan: Magic Johnson, back in the day, signed a deal — something like a 20-year deal at one million dollars flat per year. At the time it was the fattest contract because he was Magic Johnson. But what Magic Johnson made was nothing compared to what even a scrub makes today in the NBA. Just by being in the 80s, Magic Johnson missed out on hundreds of millions — probably a billion dollars total, with off-court endorsements.
Shaan: So: luck of timing in business. Not even “time the market” stuff. As an entrepreneur, the random time when you free up — when you quit your job, when your company gets acquired — there’s so much luck involved in what’s going on in the market at that exact moment.
Sam: We have a friend Sully, who was episode one of the podcast. He says: “I was at Microsoft, I quit my job, I went home to Florida, and I was just like, okay, what the hell am I gonna do now?” He didn’t have a grand plan. He had that “what do I do now” moment at the same exact day that Facebook launched its app platform. He’s like, “I was doing nothing, and Facebook launched, so I was like, okay, I want to build a Facebook app.” If he had still been employed, or had a different idea six months earlier and been in the middle of that, he would have never built that app, which never would have led to him coming to Silicon Valley, getting acquired, and getting his first million dollars.
Sam: Not to say all his success was luck — he did a lot of good things. But there is some luck of just when you’re free and what’s going on in the market. Where are the waves happening? Right now I’m doing all this stuff at this e-commerce company. If I didn’t have that, I would have been all in on Web3. I would have been investing more, building more, maybe started a company in that space — because I would have been free at a time when that’s clearly the thing to do. But if you’re occupied, you can’t do it.
Shaan: And that’s a little bit of my point. If you create a restaurant that’s really good — like Momofuku or Milk Bar — that will work in the 1920s as well as in the 2020s. Some stuff you can just make work if you give it enough time. But then there’s other things where there’s a tidal wave coming, and if you just catch the wave, even if you’re bad at surfing, it’s gonna be awesome.
Shaan: Michael Acton Smith — the guy who started Calm — told me he felt like there was this huge wave coming in meditation and mindfulness, and if he could just paddle a little bit and catch that wave, success was going to be incredibly easy. And he was right.
Sam: Same thing happened with us at The Hustle. Our newsletters weren’t this tidal wave of a business — our exit wasn’t a 20-billion-dollar thing — but we just caught this little trend at the right-ish time.
Shaan: The part most people get is market timing — “I can’t control that, I just hope I get it.” What I’m talking about is the one thing you can control: your own personal availability. Two things from this. One: if there’s a wave going on and you’re occupied with something that’s not ideal, get the hell out. You just need to be free right now. It doesn’t matter what you go do — you don’t even need the idea yet. You just need to be available. You need to be single when all the eligible bachelors are walking down the street.
Shaan: Two: don’t pick up a mediocre project that will occupy you just because you think “it can’t hurt, I’ll make some money, meet some people.” It will hurt in this silent, invisible way — you become occupied. And that likely has no long-run payoff. Lack of focus is more likely than not what ruins most everyone who tries to do anything interesting.
Career Advice: Know When to Leave [01:33:00]
Sam: I tweeted out something to do a little research. I kind of messed it up — I tweeted “What is the biggest problem in your work life right now? I don’t care if you’re mega successful or just starting out, everybody’s got some career challenge on their plate. DM me.” And I got a bunch of DMs. Should have said I’m not going to help everybody — I actually wanted to do research. I wanted to know what problems people had so I could make content that speaks to them.
Sam: At least 100, maybe 200 people DMed. One of the most common ones was some variation of “I don’t know what I want to do with my life but I know this ain’t it” or “I kind of know what I want to do but I’m afraid to go do it.” The answer to both is basically the same: whether you don’t know what you want to do, or you know this isn’t it — the first step is make yourself single. Get out of the bad relationship. Your brain is not going to properly assess the cost of staying because you’re going to see the small benefits and not see that nothing new can fit in because that thing is taking up all the space.
Sam: I don’t care if you’re at Microsoft or wherever. That was the number one and number two thing, but to me they’re the same: “I don’t like what I’m doing now, should I go do X?” It doesn’t matter — the answer to both is you’ve got to get out. If you really want to get to that amazing level, you’ve got to get rid of it. That’s the only decision you need to make right now. You don’t have to make the other decision yet.
Shaan: I completely agree. Just take enough swings and you’ll get a hit.
Sam: I have this guy who does work for our e-commerce show — he’s amazing at website optimization. He’s like, “Hey, I want to talk to you. I can’t stop thinking about Web3. I’m super interested in it but I don’t know if I’m just following a hype train. And I’ve got a good thing going.”
Sam: I ended up talking to him — I didn’t talk him out of it, I just let him talk out loud. By the end it was blatantly obvious he needs to throw away a good thing to maybe be working on something amazing. His e-commerce optimization business is doing gangbusters and he’s very good at it, but he’s unstimulated. He’s super curious about this other thing but afraid to let go because it brings in money and his whole identity is tied to it.
Sam: I go, “First question: how much runway do you have? If life costs you four thousand dollars a month, do you have enough savings?” He had six months totally liquid and another six to twelve months he could eat into without feeling bad. I think 24 months is ideal — that’s very safe. But waiting has a real cost too.
Sam: I said, “You presented three options but really there’s two. One: take on more clients and lose all your free time — do not do this. Two: keep your current clients, have some free time, collect more data for six months — do that if you’re not sure. Three: quit everything, drop all clients including me, go all in — do this if you know what you want.”
Sam: At the end I asked him three questions. One: “If you weren’t afraid of failing, which path would you pick?” — because that’s what you really want. Two: “Do you believe that if you put your mind to something you’ll succeed at it?” — I asked him this because I could see he’s a star, he’s really good at what he does. Yes. Three: “So if you know what you’d do without fear, and you know you’d succeed if you committed — what should you do?” He goes, “Well, the answer is obvious. I should go do that thing.”
Sam: I ended up talking one of my star guys off my team, which kind of sucks. But it happened. He knows what the answer is from his own reasoning. I just asked leading questions but the answers were very obvious to him. It traced back to some version of fear and anxiety.
Shaan: Fear and anxiety — you want them in the car, but they’re not allowed to hold the wheel. They can be a passenger.
Jake Paul vs. Tyrone Woodley and Dane Cook’s Distribution Hack [01:43:00]
Sam: Can we wrap up with one quick thing?
Shaan: Yeah.
Sam: Tyrone Woodley is now fighting Jake Paul. The other guy dropped out?
Shaan: Yeah. Let down.
Sam: Let down as well. Woodley’s just the most boring fighter. I wanted Tommy Fury to fight him.
Shaan: Jake Paul though — I’m gonna pay money to watch this stuff.
Sam: Do you pay money to watch fights?
Shaan: Yeah, when I feel like it’s somebody I really care about. A McGregor fight — I’ll pay. I don’t want to hassle with a bootleg stream crapping out at the wrong time. But if it’s somebody I don’t really care about I’ll just watch clips or find another way. I won’t pay 60, 70, 80 bucks for that.
Sam: What website do you use for— hey, what are we trying to do here?
Shaan: Are you a narc now?
Sam: I used to use this website called Project Free TV. I don’t think it’s around anymore. Now apparently there’s CrackStreams, which is pretty good.
Shaan: May have taken a glance at that one. I also pay for YouTube TV so I get a lot of stuff there and ESPN.
Sam: You’ve heard the Dane Cook story?
Shaan: Was it from Kazaa?
Sam: Do you know what he did? Genius distribution hack. This is one of the greatest growth hacks ever. When Kazaa and Limewire and all those torrent-type downloading programs were out there and people were downloading music — he created files that would say like “Chris Rock Stand-Up” or “Dave Chappelle Best Stand-Up.” It would be four minutes of Chris Rock, and then the next 56 minutes would just transition to Dane Cook.
Shaan: That’s how he got famous.
Sam: People were searching for those guys, they’d download the file thinking they’re getting an hour special, it’d start with a few minutes of that guy — and then: “And now, Dane Cook!” And sure enough people would listen and that’s how he got his name out there initially.
Shaan: If you think back to it — the internet was so small. I remember I would wait for something to get released, I knew all the titles, I knew how many seeders were on there. I totally could have manipulated it. I wouldn’t have thought of it back then, but me today would have. When I heard that I thought it was genius. I’m a little skeptical it’s actually true but I’ve heard it enough.
Sam: I bet that guy made so much money. Because if you could make money when CDs were eighteen dollars — that was the best time in music and comedy — all of that has basically gone to zero now. Now it’s only live shows. Back then you had live shows, CDs, and then he got into movies. He became like the most popular comedian in the world for a couple of years. Remember the movie he was in with Jessica Simpson?
Shaan: Yeah — where he runs like a Sam’s warehouse. I love that movie. I used to love Dane Cook. He’s like Coldplay — you’re a little embarrassed to talk about it.
Sam: Except I’m like, what’s the problem? This is good music.
Shaan: All right. That’s the episode.