Introduction: Substitute Teacher Energy [00:00:00]
Sam: I went to school at Belmont University. It was like a southern Christian university that had low standards.
Shaan: That’s amazing. Is that what it says on their website?
Sam: Like “a home of mediocrity — mediocre people, exceptional prices.”
Shaan: All right, we’re live. We’re doing a Q&A session. We decided this kind of last minute. It’s like when a substitute teacher comes in, they roll out the TV on the trolley, and they’re like, “Hey guys, today — you know what, I decided I want a day off.”
Sam: No, no, no. “I wanted you guys to watch this movie.”
Shaan: It works out because frankly I think people like this and we like it too. It’s a win-win. We have to do very little work and people like it. Let’s just get right into it. We’re going to keep each question at around three minutes, which — you don’t have to worry about me going over, it’s Sam.
Sam: Let’s do it. Ben, what do you got?
Shaan: Let’s do a little Q&A. So basically the background is we both tweeted out, “What questions do you have?” and we got a bunch of them. We had hundreds and we selected maybe ten or so from each of our twitters. We’ll see which ones are interesting.
Sam: All right, go.
Sweaty Startups vs. Internet Businesses [00:01:00]
Shaan: Okay, from someone named NewBET — a pretty basic one: what is your opinion on sweaty startups?
Sam: All right, here’s my opinion. I think it’s cool. Any way you can get your money, you get it. That said — the philosophy you’ve had since you were a teenager?
Shaan: Yeah, get that nut.
Sam: I think if you can get it, it doesn’t matter which way you get it. There are lots of examples of people succeeding in all different types of industries. Personally, I think making money digitally is significantly better because it requires close to no capital in some cases. You can work from anywhere. There have been times I’ve sent an email from my phone and it made a whole bunch of money. I think it’s way harder to make a million dollars a year from a brick-and-mortar business than it is digitally.
I also think that the laptop class — I saw Elon Musk call Tesla headquarters employees “the laptop class” — I think those types of people, of which most of you are, including myself, we want to do stuff with our hands. I think it’s significantly better to make money on the internet and then with all your free time go get a hobby. If you go talk to a blue collar worker, they sure as hell don’t want to be there. I’d rather be in the situation of being able to choose to spend my time that way versus being stuck in it.
In this question, the person mentioned Nick Huber — our buddy Nick — so Nick makes great points about not wanting to compete with Stanford grads, generating real cash flow, and getting rich the slow way. I agree. This might be the best path for some people.
Shaan: Nick’s great, and he’s totally right that however you want to win, win. There are many, many ways to win. If this podcast teaches you one thing, it’s how many different ways there are to win. But given that, you better choose the one you actually want. For me, I might as well choose the one most in tune with the lifestyle I want. I don’t want to worry about roof damage at my self-storage facility, or the fifteen-dollar-an-hour employee who called out sick and now there’s nobody at the front door to take customers. I don’t want those issues. I’m happy bearing a different set of issues.
I also think this whole idea of “you don’t want to compete against Stanford kids” — it’s a great sound bite, but it’s true and it doesn’t matter.
Sam: I used to say this all the time and it pissed everybody off in the office. I’d say, “That’s so true and it doesn’t matter.”
Shaan: It’s like, dude, I just want to win my high school conference championship. I don’t need to worry about you saying whatever. And if you’re doing an internet company, nobody’s like, “God, these wretched Stanford kids keep beating me.” If I did see a Stanford kid — you’ve seen those dorks — that’s not a problem. Give them a wedgie and push them out of the way. You don’t have to worry about these guys. Noogies are very effective.
The problem is not the Stanford kids. If you fail on the internet it’s because it’s a noisy place and you couldn’t get anyone’s attention. You die of starvation, not murder, when it comes to internet startups. If you’re failing, it’s not because Stanford kids beat you.
And look, this sounds like I’m making fun of Nick and Cody — both of whom are my great friends, Cody Sanchez — I’m not. But just ask them: which one is making more money, the digital stuff or the brick-and-mortar stuff? I don’t actually know the truth. You guys are pretty active on Twitter. Which one do they think is better? Who knows.
Interesting Businesses That Didn’t Take Off [00:07:00]
Shaan: All right, next up. Someone named “it block mates” asks: what’s the most interesting business you’ve seen that didn’t take off, and why do you think that was? Go for it.
Sam: So there was this app back in the day, and when I saw it I was like, “This is gonna hit.” It was made by these Russian dudes and it’s called Povio.
What Povio used to do — every other social network was about posting. Facebook: I go to a party, I post an album of photos. Instagram: I’m on the go, I’m at a cafe, I’ll take a photo of my cappuccino. It all had this look-at-me, I’m-kind-of-bragging-about-my-life thing.
I’ve always said that when a social network hits, it’s not because of a feature, it’s because of a change in the privacy policy. Facebook was the first time you used your real name on the internet, because you were doing it with other college kids from your same school. That’s why Facebook got your real name, your real relationship status, your real courses. Twitter was, “You don’t have to be my friend, you can just follow me.” That’s a change in privacy policy. Snapchat: this is a disappearing photo, it’s private. Every great social network has a change in the privacy policy.
Povio had a genius one. You would request a photo from someone else. I would ping you, it would open your phone, go three, two, one, and take a picture of wherever you were or whatever you were doing. You could basically say “what’s up,” and the person would default-reply with a photo. I was like, “This is genius. They’re giving people even more excuses to take random, useless pictures. This thing’s gonna fly.”
Sure enough, on the first college campus it started to work and was growing. And then it just kind of faded away. It never made it. I still believe in this mechanic — if somebody made an app where you’re basically saying “what’s up” and they reply with a photo, you’re pulling the photo from them rather than pushing it online — I think that’s a game changer. But I was wrong. It never worked.
Shaan: Mine is Doorsey — D-O-O-R-S-E-Y. I’ve always wanted to invest in companies that have a good chance of making buying a home online possible. I’m a firm believer that people will end up buying almost everything online, and there are only a few categories left. Hardware is one — Home Depot still crushes it because you don’t buy a screw on the internet. And homes — nobody’s figured it out yet. This company hadn’t worked yet and I still think there’s an opportunity for a company to let you make a hundreds-of-thousands-or-millions-of-dollars purchase on the internet.
Do you remember when Mark Cuban bought a jet on eBay and it was all the rage?
Sam: I didn’t even know about this.
Shaan: Yeah, when he sold broadcast.com he became a billionaire and bought a fifty-million-dollar Gulfstream on eBay. People were freaking out. It’s not even that interesting, honestly — a jet, if it’s the same model, you kind of know what you’re getting. But homes are a different story.
Sam: I just asked Google’s AI what percentage of Home Depot sales are online, and it said in 2022, sixty percent of its sales were online.
Shaan: Even Home Depot is selling the majority of products online. But I’m into things that can’t be sold online yet that should be. And I think homes are one of them.
What Does “Enough” Look Like? [00:17:00]
Shaan: All right, what do we got, Ben?
Sam: This is something we’ve talked a lot about recently: what does “enough” look like for you? Shaan’s got a much better answer than I do. For reference, I put a bullet point in and wrote out what my answer might be — mine’s this long thoughtful thing — and then Shaan’s answer basically just says “I don’t think there’s ever enough.”
Sam: Whenever you explained your point of view it sounded like… there have been multiple times in my life — a hundred thousand dollars, five hundred thousand dollars — where I thought “I won’t worry anymore.” And I’ve hit a lot of those different targets and I still worry. There are times where I worry less for a little while, but… have you ever heard the idea of people who lose a limb? They’re bummed for like six or twelve months, and then they go right back to where they were. I think it’s the same with money stuff. You make the amount you thought would do it, and then you go back to where you were. That’s why I said “never enough.”
Shaan: All right, let me say a couple of other ways I think about this. Paul Graham did this thing where he created Y Combinator — basically the most successful company in Silicon Valley besides Google and Facebook. And then he retired. He moved to the woods in England and just writes code in his cabin with his kids, writes poetry, paints, goes for walks.
And I was like, “This guy thinks he’s got enough, huh?” All of us rats were shaking our fists being like, “You get your ass back in here.” And I got inspired by that. What’s the “enough” state — not money, but what would I want to go do?
So instead of thinking “what number would feel like enough” — because I think that’s a trap — I thought about what I would do if I felt free. Here’s what I came up with.
I heard this Naval quote: “Retirement is when you stop sacrificing today for an imagined tomorrow.” That hit home. What it means is: the moment you do things in your day where the act of doing them is the reward — not you’re doing them today sacrificing for some future payoff — at that moment you are free. That’s the goal. The goal is to on a daily basis do things where the act of doing them is the reward.
So if I did that, what types of things would I want to do? Here’s what I came up with. I think having a big podcast is actually the best job in the world — obviously I’m biased, but I’ve tried a bunch of things and this is the best. If you have a big podcast, you’re famous but only famous amongst nerds, which is kind of the not-annoying way to be famous. All the good parts of fame without the bad. You get rich but you didn’t have to chase money. You get to create content, but you’re not the annoying twenty-four-seven vlogger who’s got their phone out and ruins their actual life for content. With a podcast, we sit here for like two or three hours a week and record, and that’s it. The other 165 hours in a week we do whatever we want. We don’t have to think about creating content and we don’t have to get hurt doing it — not like that YouTuber who crashed a plane on purpose for views.
And then for fun, I would basically coach a basketball team Mighty Ducks style. And I’d want to just chill out and shoot the shit in a writers’ room for a TV show, or teach at Stanford twice a week. Those are things I would do for the pure joy of doing them, not for some future reward. To me, I’ll have enough when my day is mostly stuff like that.
Sam: Why haven’t you tried to get a teaching job or a coaching job?
Shaan: I haven’t put enough attention on it. This question made me think, “Oh, why don’t I just go do that now?” And often life is that simple. It’s not that there’s actually any barrier in the way. I just didn’t put my attention on what I actually want.
Sam: A good excuse is you have young kids, so maybe once they go to school.
Shaan: I’m not a believer in that. I think it’s really just a matter of — I didn’t put focus on what I really want. Okay, then go get it.
By the way, there was a good Paul Graham thing. This guy tweeted, “There are very few second-time founders, because anyone smart enough to succeed the first time isn’t dumb enough to do it all over again.” Paul replied: “Anyone smart enough to succeed the first time is still running that company.” And then our friend Akita jumped in: “Wonder what happened with that washed-up Viaweb founder and what he’s doing these days.”
So even the smart guys like Paul can get things wrong once in a while. He says he’s got enough — but who knows. I actually do believe that he does.
Sam: I think your answer is better than mine. It’s about enjoying the experience more. When I was running The Hustle, I look back and wish I’d enjoyed it more during the process. But it’s a very challenging thing to do.
Shaan: I’ll ask you one thing: are you okay with knowing that you’ll never have enough?
Before you answer, let me put it the other way. If you feel like you’ll never have enough, to me that means you’re never really free. The most fun interactions you know — this is like when you meet with somebody you want nothing from and need nothing from. Those are the best interactions with people. There’s no more freeing feeling than literally “I don’t need you and I don’t want anything from you.” Versus the opposite, when you want someone’s approval, or you need them to like you, or you need them to hire you. Those are the most stressful interactions. So to me, if you want to be free, you’ve got to believe that there is such a thing as enough.
Sam: I think we’re thinking about it differently. Let’s say you’re a comedian — you’re Hasan Minhaj. Is he ever going to be like, “I’m funny enough, I don’t need to improve my craft anymore”? I don’t think so. He could find a bit of contentment being on top of his game and awesome, but he can always get better. That’s kind of what I mean when I say “never enough.” If my craft is building companies, there’s always more I can do to be better. But that doesn’t mean I’m unhappy or unsatisfied with where I am.
Shaan: Fair enough.
College Regrets [00:30:00]
Shaan: All right, Ben, let’s go to the next one. “If you could go back to your college days, what’s the one thing you would have done differently, knowing what you know now?” That’s from Sam Faber.
Sam: I was a huge idiot in college — and not even the cool kind of idiot. I was just doing dumb stuff, going to parties, late nights.
Shaan: Did you love it, or are you saying it was bad?
Sam: I was just doing nothing. I was a do-nothing idiot. That’s the worst kind. Now I look back and I’m like, wow, college is a gold mine. You can make lifelong friends, meet future business partners. I wish that when I was in college I’d been launching businesses. I had a captive market of students I understood and could reach. I could have been working on my skills then versus starting after college.
And the alumni thing — I didn’t realize how powerful it is to just be like, “Hey, I also go to Duke.” And they’re like, “Cool, you want to hang out?” It’s that easy to connect.
I would mine that gold mine. I was sitting on a gold mine and didn’t even look down and realize what I was sitting on. The only smart thing I did was study abroad. I went to Australia.
Shaan: Sydney? Man. I think Sydney, Australia is the greatest city. It’s the best place to be a nineteen-year-old. The greatest place on Earth.
Sam: My biggest regret is that I didn’t take high school seriously enough to get into some of these amazing schools. I went to Belmont University — a southern Christian university with low standards. Back then it was very expensive, and it was just like such a mediocre situation. When you say you went to Duke, I envy you so much. At least you got the basketball guys were the best, and a lot of your peers were very smart. I bet you met tons of people from all over — foreigners, people from New York, people from California.
I didn’t get to meet any of those people. The first Jewish person I met was when I moved to San Francisco at twenty-two. It was just mostly one kind of person. I wish I was around more of a global group of people.
I also wish I’d taken seriously the idea that the things you do in college aren’t that important — they don’t have to be the thing you do. But if you take your hobbies seriously, it’s a really fun time to try on different personalities and things. I wish I’d taken that more seriously.
Shaan: I totally agree with that part. I thought in college the “thing” was your classes and the result was your grades. But that’s completely backwards. The thing is the people and the environment — that’s the one thing you’re never going to get back. And if you really wanted a result, the way to take it seriously wasn’t to get A-pluses or be an amazing chemistry major. It was actually, “Hey, this is four years and after this I’m supposed to figure out a job and pick a career. I should dabble. I should sample things — it’s Costco at noon and I should sample a bunch of different things. Meet people who do them. Take this time to figure out what I actually like to do.”
I wish colleges were oriented like that. But they’re oriented around the opposite assumption: pick what you want to do, put your head down, focus. That’s the wrong time to focus. You should be dabbling at that stage.
Sam: Do you have good credit?
Shaan: I’m okay — good enough credit.
Sam: I wish I had gotten a credit card at eighteen and used it for everything and always paid it off so I could build credit history. I didn’t get a credit card until I was twenty-four. Then I started my company and I’d max it out constantly, and always pay it off right before I had to. My credit card utilization was always like a hundred percent and I didn’t have a long credit history.
Shaan: Did that come back to bite you?
Sam: When I tried to buy the house I’m living in now, I couldn’t buy it. My wife had to buy it — because my credit history wasn’t long enough, and because you’re a business owner, getting a mortgage is really really challenging.
Deal-Making: When Deals Fall Through [00:40:00]
Shaan: All right, what do we got?
Sam: This next one is: “Have you had a deal not go through when close to finishing it? If so, what did you learn to do better, and how did your mentality regroup to start the process over?” Not sure, but: “I feel like the sellers are trying to tank this business acquisition which is supposed to close on May 31st.” That’s from Mackenzie Reed.
There’s a recent media company that went bankrupt that tried to buy The Hustle. We got to an LOI and it completely fell through. There were like three others that also fell through. And I was devastated. So I changed my opinion to this: any deal I have, I will act as if it’s going to happen, but assume it’s not going through. And if it does, I’ll be happy — because most fall through.
To address the last question — “I feel like the sellers are trying to tank this acquisition” — I had that exact same attitude when I sold to HubSpot. And then one day I got to know the woman I was working with there, and she was like, “Look, you don’t understand. We’re worth twenty billion dollars. This deal is really not a big deal to us. It’ll do a little something but we already got board approval to do it — which means I told my boss, and that boss told their boss, and then that boss reported it to twelve people who are billionaires. If this deal doesn’t go through, all twelve of those people have to change something, and I’m going to look stupid, and my boss is going to look stupid, and the other boss is going to look stupid. So because we’re a big publicly traded company, if we say we’re going to do something, we’re going to do it — not necessarily because it’s a logically great deal, but because I don’t want to look dumb in front of all my bosses.”
Versus when you sell to a smaller company or an individual with money — a lot of times they will nickel-and-dime you or try to dock you. When you sell to a big publicly traded company, nine out of ten times it’s not in their best interest to screw you.
Shaan: That’s a great answer. I’m the same way. I go into every single deal assuming the deal is not going to go through, because — as Emmett said to me — “Birds fly, fish swim, and deals fall through.” That’s what they do. Deals fall through. It is not an outlier or exception or disaster when that happens. A deal did what deals do. They fall through. What are you worried about? Sit your ass down. That’s how I talk to myself when I get emotionally attached to a deal.
So the emotional detachment is key.
Sam: How do you do that?
Shaan: Part of it is you need a bulletproof mindset before you get into an M&A transaction. It’s too late when you’re in it to be like, “All right guys, I’m gonna toughen up this brain to be able to operate in a very tricky circumstance where I might get life-changing money or it might all fall through.” You’ve got to train before that.
Second thing — not only do deals fall through, it’s also not fatal when they do. In fact, every deal I’ve done has had a fall-through moment, if not two. My rule of thumb is: every deal that does close will have two walkaways along the way. You’re going to walk away, or they’re going to walk away — that’s going to happen twice before this deal actually happens. There will be two moments where it feels like the deal is dead.
Sam: Have you ever mentioned the other two people you almost sold to instead of Twitch?
Shaan: I think I said before that we got pretty far down the road with Facebook. One of the good things the Twitch / Amazon Corp Dev guy told me was, “Look, I’m sorry we’ve been so slow and can’t give you everything you want on price. But here’s the good news — we will not retrade this deal.” Retrading is when you come back and try to change the terms in the second negotiation once everybody’s fully emotionally invested.
But then you think, “Oh, you’re just like a doctor who tells everyone their kids look great.” He confirmed he was an investment banker, had done 100+ transactions, and said, “Yeah, both Facebook and Amazon — if they give you an offer, they’re solid on that. It won’t close because you didn’t disclose something that later comes out, or you change your mind. It’s not going to be because of them.” The good news about big companies. The bad news is deals get hung up or delayed for all kinds of terrible reasons.
When we were doing the Milk Road sale, I got some great advice. The M&A advisor basically said the offer I had in hand was a solid one and shouldn’t be discounted. But the competing offer, which was nominally higher — its fair value was probably half as high once you applied the discount of “this deal might not close.” He said, “If I’m honest and apply a discount, it’s at least fifty percent based on the normal way that M&A deals work.”
That turned out to be exactly right. We tried to go with the higher offer, and sure enough more stuff came out of the woodwork that gave us hesitation. We realized we couldn’t just take the headline numbers — we had to factor in the ability to close and the credibility to close.
The way you get around all of this is: say the bad things up front. You say anything that will potentially ruin it as early in the process as possible. You actually gave me this advice when we were going through the Milk Road process. You said, “Here’s what you’re gonna do. You’re gonna go to dinner and say: ‘Awesome, sounds like we’re all excited. Now I’m going to tell you every reason you should not buy this company. I’m going to show you every skeleton in the closet right now, to save us pain later. If anything here scares you, I’m happy to explain it — or if it just doesn’t work, we can know now.’”
And I did exactly that. After the deal went through we did a postmortem and they said that’s exactly how you move — you don’t waste three months dragging it out when you could have known up front.
Sarah’s List: Safe Jobs with High Upside [00:55:00]
Shaan: All right, Ben, next question. “Do you have any updates to Sarah’s list, or any new additions?”
So Sarah’s list is this list I made — it’s named after my wife — basically companies where you could join and have a safe job. You’re hopefully not going to get laid off like at a ten-person startup. You can still get paid a lot in salary, still have maternity/paternity leave, and also your stock could potentially 10x.
The real story is: Sarah joined Facebook, and then Airbnb — not super early when they were in their apartment figuring it out. These were already multi-billion-dollar companies. You get the fat salary, the unlimited oat milk in the break room, the maternity leave, everything you want — but also you get a stock package that, even if you’re not an AI engineer, could make you a millionaire in a four-year vest cycle if the company 5x’s. Nobody talks about this, but you have to correctly identify which companies those are.
Sam: The opposite list matters too. What companies raised too much at the wrong time at the wrong valuation and are basically underwater? You could go to TechCrunch, sort by the bull market years — 2020, 2021, maybe even a little 2019 — and anything that became a unicorn in that era, assume the likelihood is bad until proven otherwise. Ask your CEO: “What is the fair market value of this company right now? What did we last raise at? How much total money have we raised?” If the answer is 600 million dollars, that means if you sell the company, the first 600 million goes back to investors and nothing goes to employees.
Shaan: Did I ever tell you the craziest thing about Airbnb? They had a cafeteria, and their whole shtick was that every single thing — from the ketchup and mayonnaise to the Coca-Cola to the trail mix — was made in-house on premises. Everything was made right there on the spot. It was amazing.
Sam: I remember the same thing at Zynga. I went to Zynga and met the head chef. The culinary team was forty people. I showed up and I had some Cheez-Its. I opened up the bag and they heard the crinkling of a packaged good in that kitchen — the whole kitchen looked at me like I’d said “bomb” on a plane. I was like, “I’m so sorry, I don’t know how this got here.”
Shaan: Do they still have it?
Sam: Of course not. The whole building got sold for more than the company was worth at the time. I think Zynga sold their San Francisco building for 250 million dollars when the market cap of the company was 200 million dollars. Either that or more than all the profit they’d ever generated. Now it’s owned by Take-Two, who makes Grand Theft Auto and NBA 2K.
Shaan: I love those chef companies. Sarah’s list — you’ve got to go date somebody who works at a tech company with all-you-can-eat food. What are you doing otherwise? You need to bring some attributes to the relationship.
Sam: I was like the Pablo Escobar of smuggling Clif bars out of tech companies for a three-year period. I had free prosciutto for a year. I used to bring Tupperware containers. Make sure you stay till seven. Facebook dinner didn’t start until 5:30. It takes you an hour to get home — where’s my prosciutto?
Maintaining Friendships at a Distance [01:05:00]
Shaan: Ben, what do we got?
Sam: “Do you have any frameworks for maintaining healthy friendships, especially when you’re separated by distance?”
Shaan: Mine’s simple. I’m in the phase of life right now where I’ve got one simple phrase when it comes to friends: No New Friends. If you’re in, you’re in. It’s a mental problem if you’re out. Say no to everything. If you’re in, you’re in. If you ain’t, you ain’t.
Sam: Same. I suck at this. I apologize to my friends — I’m a shitty friend to them and they know it. I do feel bad about it. But you can only try to be great at so many things at once. I’ve got kids. Which things are you gonna be great at? Great dad. Try to make a bunch of money. Try to get into incredible shape. Those are the things I’ve prioritized right now, and friends had to take a little bit of a hit.
Shaan: All right, you loser.
Stupid Business Ideas Worth Doing [01:08:00]
Sam: Ben, what do we got?
Shaan: “If you were to start a business based on the quirkiest or most ridiculous idea you’ve ever had, what would it be and why?” Your answer is actually good, Sam.
Sam: Did you have an answer for this?
Shaan: No, because I’m not that quirky of a person. Say yours — the IQ test is actually a good idea.
Shaan: All right, so I remember I met a guy who would sell stars — literally a star in the solar system for twenty-five dollars. He would name it after you, just in his own database. And then I saw this guy who’s been crushing on TikTok — they own a small piece of land in like Dublin or somewhere, and they’ll officially knight you as a “Sir.” You get an official title, you own a one-foot-by-one-foot plot of land on this property.
When I see things like that, there are really two reactions. Most people roll their eyes and say, “This is what’s wrong with the world.” And then there’s me, who says, “Man, what’s wrong with me? Why haven’t I done this?” That’s kind of where I’m at. I would love to just do some of these stupid things. I want to be the Pet Rock guy or the Million Dollar Homepage guy. That would just be fun as a challenge.
Sam: I have an idea. I want to create a new IQ test. Who doesn’t want to seem like they have a high IQ? You could build a D2C IQ test that people would pay to take. Or go all in on something super woo-woo — horoscopes, crystals, something like that.
I actually launched a D2C crystal brand, an e-commerce brand, for a month. Now that I know how e-commerce actually works, that brand was actually working. I was just too much of a noob to understand it. E-commerce is basically CAC versus LTV — what’s the lifetime value of a customer compared to the cost of acquiring them. My LTV-to-CAC was actually good. I just didn’t trust it enough at the time.
My first e-commerce business before the one I made was a crystal brand. In my garage right now I have like 4,000 rose quartz coasters, because I didn’t sell them. I shut it down. How much did it cost you to buy and sell?
Shaan: These are very cheap to buy. Gross margins are like 75-80%. You buy it for two bucks, you sell it for ten.
Sam: I was looking for new ideas outside my normal box, so I opened up Cosmo magazine. There was this two-page spread about crystals: Adele will not go on stage until she uses her rose quartz crystal. Kim Kardashian, after she got mugged for her four-million-dollar diamond ring, claims crystals are one of the only things that kept her anxiety down and she keeps one in her bag at all times. Gwyneth Paltrow from Goop — obviously huge into crystals. There was also the Adam Sandler movie with Kevin Garnett where he buys that million-dollar black opal. That came out after I’d already done it.
I basically saw that and thought, “If Kardashian, Adele, and Jennifer Aniston are all into crystals, trust me — your perfect e-commerce customer, a woman in the midwest, is going to buy this stuff.”
Shaan: But also, you don’t want to be a fraud. If you’re selling crystals — “fraud is in the eye of the believer,” as I say. There are a lot of people who genuinely believe crystals are good and help them.
Sam: So you know Kinsey in Idaho — she wants to buy the heck out of your rocks. If you have a sign that says “Simplify” or “I Love Us,” she’s going to be one of your customers.
Hampton’s Origin Story: Sam’s First Five Big Moves [01:15:00]
Sam: All right, Ben, what do we say? Where are we at?
Shaan: This one is mostly for Sam. “What were the first five big-boy moves you made at Hampton?” — from Joe Watkins.
Sam: I don’t know about the first five, but — I didn’t even buy a domain name. It was just Hampton at hampton.squarespace.com, and I sent the link to a bunch of friends, then they sent it to a handful of others. People would sign up on that page, which was just a Typeform. Then I called every single person and interviewed them. Me and Joe did the back-end stuff, but I did the front-end stuff — calling all the potential customers. I must have interviewed a hundred to two hundred people. I was the one who sold and got us the first million dollars in sales. My calendar looked like I was going to exceed my personal capabilities and skill sets very soon, so I should hire a CEO. But getting the first million in sales is what I did for like two months.
Shaan: The other thing you did is nail the brand and the name. The name won’t break you, but it can make you. Hampton is a perfect name because you borrowed the prestige of the actual Hamptons.
Sam: I hired an agency for fifteen thousand dollars. Basically what I did was send them a whole bunch of really old Rolex ads and said my favorite color is British Racing Green — I love that color, I’ve had motorcycles in that color, I have all types of toys in that color — and I said, “Make it look like an old Rolex ad, use British Racing Green.” That’s how it came to be.
Shaan: Fifteen thousand dollars for you — is that just nothing? Are you just like, “Let’s do it”?
Sam: Let’s just say this: last Saturday I drove twenty minutes to return a spatula to Target for seven dollars. I had to make sure there wasn’t a second one stuck on there.
Shaan: That’s hilarious.
The Three Small-Boy Moves [01:22:00]
Shaan: All right, what do we got?
Sam: Next up is from Josh Redd, who wants to know: what are the three most common small-boy moves that you see?
Shaan: So we have this phrase — “no small-boy stuff.” What is small-boy stuff? The first rule is: if you think something might be small-boy stuff, it is. But besides that, the three big buckets are the three W’s: waiting, worrying, and wanting.
Anytime you find yourself waiting to do something you actually want to do — that’s a small-boy move. You’re focused on the wrong things. Worrying — same thing. Worrying hasn’t done a lot of good for anyone. Sam’s “worry time” framework is a fantastic approach for that, go look that up. And wanting — meaning wanting what other people have. People are happiest when they’re grateful, meaning they want what they have versus wanting what they don’t have.
So if you find yourself in a state of mind you don’t want to be in, that small-boy state of mind, it’s probably because you’re waiting to do the thing you actually want to do, you’re worrying about something that might happen that might be bad, or you’re wanting something that you don’t have that other people have — you’re being bitter, jealous, and so forth. The three W’s capture most of the things that are small-boy activities.
Sam: Have you heard of the phrase “external locus of control”?
Shaan: I have heard this phrase many times and have no idea what it means.
Sam: Locus is a bug — that’s where I started.
Shaan: You’re totally wrong. So internal locus of control means you believe your position in life and how you feel is because of your own choices. External locus of control means you think, “I’m in a bad mood because traffic is bad and it’s their fault,” or “I’m poor because the government won’t help me” or “everyone’s out to get me.” Internal is the opposite — I control how I feel, what I do, where I am in life.
There’s a direct correlation between small-boy thinking and external locus of control. When you say “I am the way I am because I choose to be” — that’s internal. Anything where it’s “I have to wait until this is ready” or “I have to please these people” — that’s typically a loser mentality.
Shaan: I was actually telling somebody this yesterday. I said: where do you think the power lives in this scenario? Let’s say there’s a plant that’s not growing. Where’s the problem?
They said: “Well, it could be the soil — it’s the environment.” Or: “Maybe it was just a bad seed — the genetics.” Or: “It’s not getting enough sunlight because other plants are blocking it — competitors taking the finite resource.”
And the answer is: there is no problem. You are the plant. Just grow. Don’t blame anything. Don’t feel lack in any one of those areas. You want to be the plant that can grow under any conditions, from any seed, in any environment.
Sam: I get along with myself the least, I hate myself the most, when I think that way.
Shaan: See, you didn’t know what the term meant but you came to the same conclusion that hundreds of years of psychologists figured out. Thousands of years of wisdom — and you just sort of came up with a better version on an afternoon and a better analogy.
Sam’s Best Quality, Shaan’s Best Quality [01:33:00]
Shaan: All right, Ben, what do we say?
Sam: We got an emotional one, ladies and gentlemen. Grab your tissues. Sam, what is in your opinion the greatest quality that Shaan has? And Shaan, same question about Sam. That’s from Griffin Humphrey.
Shaan: Good question. Shaan’s greatest quality is — I feel like I don’t want to look you in the eye right now.
Sam: Should I close my eyes? It’s like when someone puts their palms out on the table and you’re supposed to put your hands in theirs.
Shaan: That’s weird. You don’t look people in the eye when you’re doing that — just like complimenting each other and going to the bathroom.
Sam: Have you ever noticed when you go to the bathroom with someone, even if you’re walking there together, as soon as the zipper goes down the conversation stops? The fly is like the off button. Then you zip up and go back and right back to the conversation.
Shaan: That’s what this is like. Shaan’s best attribute is that his attitude is always positive. I don’t think I’ve ever gotten him rattled — and not that I’ve tried. He’s very pleasant, almost 100% of the time. I’ve never seen him get upset about stuff. That’s actually the frustrating thing about him — he doesn’t get frustrated sometimes. But at the same time I’d rather have that, because I’m fairly emotional and I get frustrated easily. So I’d say his best characteristic is the ability to stay even.
Shaan: Internal locus of control, baby. You control your mindset. The locus is inside of you. It never goes outside.
So I’d say that’s easily your best attribute — the ability to manage your own mindset.
For Sam’s best quality — the reason I keep saying what I keep saying about this — it’s not like, “Sam got lucky because of this,” or “He’s got people helping him,” or “He’s just born with some talents others don’t have.” It’s that I think Sam just does a better job of cranking the intensity to twelve when it’s time.
If you’re going to get in shape: inject TRT, build a home gym, hire a personal trainer, hire a coach, buy the best equipment, wake up every day, do the program, push to your actual max during the workout, measure everything, post publicly so you’re ashamed if you don’t do it — you go the full way.
I had a very similar idea for a peer group thing years ago. I kind of dabbled with it, it was actually going pretty well, but I got bored, decided it wasn’t the right thing, didn’t see the big picture. And then watching you take that same idea and do it at level-twelve intensity — that’s such a gift for me. I get to see a without-intensity approach to the same idea and a with-intensity approach. And it shows what the difference is. The difference is everything.
I also wrote: Sam’s got a code and he lives by it. I think you’re more honorable than most — and definitely more than me.
Sam: What code? I don’t view myself as having a code.
Shaan: Do you feel like when you give someone your word that it’s done?
Sam: Yeah, for life.
Shaan: Do you feel like if someone’s your friend they should fight for you and die for you, and any small slight is a loyal stab to the heart?
Sam: I feel like if we’re in public and you get in a fight and throw a punch — even if it’s your fault — it’s over. And then afterwards I’ll be like, “You’re an idiot, that was really inappropriate.” But in the moment? Yeah. We die together. I disagree privately, publicly I show up.
Shaan: I don’t even agree with your whole code. I think you’re crazy. Like when you chase down people who broke in because “you broke in, now we duel” — I’m like, “Sam, you should not do that.”
Sam: I feel that way, yeah.
Creative Entrepreneurs Worth Watching [01:42:00]
Sam: Let’s do a creative one really quick. “Who are the Creator-preneurs you are paying attention to and why?”
Shaan: I like Isaac French. Someone who’s creating content but also an entrepreneur — building a business around their podcast or YouTube or Twitter. I hung out with him and asked, “Why are you so purposeful with everything you do?” He goes, “That’s just part of our religion. We feel like we have to be excellent — that’s how we show that God’s great.” I was like, “Okay, that’s it.”
I like Jasmine Star. She’s got a software company. I met her through Hampton. Whenever I hang out with her, I feel like I might cry — she’s so intense. She describes herself as a Latina woman from East LA, and she’s like, “I’m going to crush all these tech nerds.” I love that attitude.
And Jason Yanowitz and Austin Rief. Jason runs Blockworks, a crypto company that just raised some money — I would never bet against them. Austin Rief, the founder of Morning Brew — I would never bet against that guy either. He’s a stone-cold killer. And I admit I used to be biased against Morning Brew because of loyalty to The Hustle. Since we were friends, your enemies were my enemies. But Austin’s actually awesome. He’s not one of those successful-but-stupid guys — he’s genuinely smart. And he’s young, I think only twenty-seven. I think he’ll have north of a hundred million dollars before he’s thirty.
Sam: My Creator-preneurs — I try to look at people in different bubbles, because if I just look at other business content creator entrepreneur people, I’ll become the lame Twitter-thread copycat guy. So I look outside my normal areas.
For example, Courtney Shields — a mommy influencer. First thing I subscribed because when you look at what mommy influencers on Instagram do, it’s a whole different style of content you can steal ideas from. The second thing: every other mom influencer created a fashion brand — my swimsuits, my dresses, the same merch and apparel playbook. Courtney picked an incredible business that was perfectly aligned with her story: a scalp-care thing. High margin, only a couple of SKUs, none of the headaches of fashion, a beautiful business, and crushing it — something like forty million dollars last year in revenue without much ad spend. That’s perfect project selection. That should be a multi-hundred-million-dollar business. Two hundred and fifty million, at least. I couldn’t admire it more.
Others in our niche: Pomp — I’m inspired by his level of output. The guy’s a machine. I’m super weak and inconsistent with output and he is super regimented. I also want to see how he’s redefining himself outside of Bitcoin right now.
Tim Ferriss — very different than me. He’s ultra-thoughtful about his brand. Measured, thoughtful, cites his sources, doesn’t say yes to a lot of things. He’s the opposite of me in every way. I like to see what he does because I want to learn from people with different play styles.
Steve Bartlett — same thing. He’s high style. Everything Steve Bartlett does is cool. I buy a hat, he buys a hat, and mine looks shitty and his looks awesome. He’s also like six-foot-one and pretty fit.
Shaan: I always look at Steve McQueen — “the king of cool.” I look at clothes he wore, and then you see on Reddit someone’s like, “I tried to buy the Steve McQueen outfit,” and you look at them and you’re like, “Oh, you look like store-brand Steve McQueen.” Some people just have it. I’ll look at Brad Pitt’s clothes and see people try to dress like him and think, “Dude, you just don’t got it.” You’ve got the face, you’ve got the body — sometimes that’s just it.
Who Would You Want to Live Like? [01:53:00]
Shaan: Here’s a really quick one. They asked one thing but I’m going to phrase it differently: who would you want to live like — Gary Vaynerchuk, Elon Musk, or Mr. Beast?
Sam: I think all three of those guys would be horrible to live like.
Shaan: Only Elon because he’ll just never be there. The guy’s got the empty room and it’s actually all yours. You’re living in a double but it’s all yours. That’s actually a pretty good deal.
Sam: I’ve lived with and hung out with a handful of highly successful people. I hate going to their house. Their homes are usually a wreck.
Shaan: If I panned a camera around this office right now, people would unsubscribe. Think of your worst episode of Hoarders — that’s currently what my office looks like.
Sam: That’s disgusting to me. How do you live that way?
Shaan: I just do, bro. My room’s like a mullet — it looks great from this angle but you’ve got all this party nonsense in the back.
Sam: After I record —
Shaan: I’m interested in having a lot of fun with my life. I only have so much time on this little planet. I want to enjoy it. This is a great question. I’d be really curious to hear yours — I think yours would be very different than mine. Does anybody come to mind?
Sam: Rob Dyrdek.
Shaan: Say a few more words about that.
Sam: Rob Dyrdek — when I think of what I want my life to be, it’s basically to have a Fantasy Factory. Rob Dyrdek, I think, has a ton of fun. He views business as an art instead of a McKinsey spreadsheet. This is how he expresses himself. He broke nine World Records or something like that just because — I love people who do dumb stuff just because it seems fun. He’s up there.
And Joe Rogan. He seems like he’s living his life. What are the five things you most enjoy doing? Comedy. UFC. Talking to smart people and learning new stuff. Hunting. Cool — that’s my life. He integrated his career, his life, and his friends. His friends are other comedians, people in the UFC. His career is: I’ll be the top broadcaster for the UFC, the top podcaster, and one of the top twenty comedians. He’s made a bunch of money doing his art.
And he draws hard boundaries. He loves the UFC but won’t travel to Senegal for a pay-per-view. Only does the ones within a two-hour flight. That’s his rule. And he’s okay not doing the rest. He’s not divorced. He seems like he’s got his head on straight.
Bill Simmons is the same thing for sports.
And then my uncle Vinnie. Literally his nickname that his whole company calls him is “Smiley.” I was on the phone with him — he’s so excited, he’s doing a webinar about multi-family real estate right now. Not something that sounds super glamorous, but he is excited about it. He is having the most fun in his life. He wears what he wants, dresses the way he wants, talks the way he wants, does what he wants with his time, travels the way he wants. His joy meter is permanently stuck on max.
I admire that because with Joe Rogan it’s easy to say, “Yeah, if I also had the best podcast and the UFC and great friends, I’d be having a lot of fun too.” My Uncle Vinnie’s a great example because he doesn’t have any of that, and he’s having all the fun right now. He’s not waiting to achieve all this stuff to have fun. He’s having it now.
Shaan: What type of Indian guy has the name Vinnie?
Sam: He went with Vinnie to make it more acceptable when he moved here, and then his whole company just called him Smiley because the guy never stopped smiling.
One time in Austin we had a bad office that had rats. We nicknamed one Vinnie — like Eddie from New York — and that was the name of our office rat.
Shaan: If you’ve named an office rat or mouse, you’ve grinded. You’re on the right track.
Closing [02:02:00]
Sam: All right, Q&A — this is the easiest stuff ever to talk about. Maybe we should just do this every time.
Shaan: Now I know why Gary Vaynerchuk did that whole show — it was just asking GaryVee. All you have to do is just answer questions.
Sam: Yeah, this was fun. We should do more.
Shaan: All right, that’s the pod. Thank you.