Andrew Wilkinson, co-founder of Tiny, joins Sam and Shaan to unpack his summer digital detox — how burning out on Twitter taught him about dopamine, addiction, and what actually makes life feel good. The conversation expands into cruise ship investing (buying boring businesses that just work), AeroPress’s zero-marketing acquisition story, mimetic desire and the dangers of wanting what your peers want, and what meeting Steve Jobs at 15 was actually like.
Speakers: Andrew Wilkinson (guest, co-founder of Tiny), Sam Parr (host), Shaan Puri (host)
Matthew McConaughey, Audiobooks, and Introductions [00:00:00]
Shaan: Apparently Matthew McConaughey, when he wanted to write his book, drove four hours into the desert and literally lived in a shack for two months and wrote it. Did you read it?
Sam: I read part of it. If you read it using Matthew McConaughey’s voice while you’re reading it, it’s actually pretty entertaining — good stories. But it’s like, I’m not sure I care that much about Matthew McConaughey’s life.
Shaan: Why wouldn’t you just listen to the Audible book? If you wanted his voice to read it?
Sam: I don’t know. I’m not smart enough. That would have been way better.
Shaan: You should have done the Audible book.
Sam: I just honestly didn’t think about it. Sounds like a good idea — I should probably do that.
Sam: Okay, so Andrew — we’ll do the intro now. Andrew is a great friend of ours. He has this big business called Tiny, where they own a bunch of different businesses, north of $100 million or so in revenue. Took a company public. You’re successful in the traditional sense of the word. You’re a good friend. You normally come on a lot, but you just tweeted about how you kind of took off for all of August and bailed — you were having a meltdown. A digital overload meltdown. You just bailed, right?
Andrew: Totally. It was bad. It’s interesting to think about — I think this happened to a lot of people over COVID. Life just shifted in a weird way. My life became crappy over COVID, which is strange because I had this amazing year. We took a business public, we raised a big fund, we got to work with all these interesting people, we bought some great businesses, I didn’t die of COVID — all these great things happened. And yet I was totally miserable.
Andrew’s COVID Meltdown and the Dopamine Problem [00:02:10]
Andrew: When I zoom out — I live in Victoria, Canada, and I didn’t even have an office. I worked out of cafes. I’d go to the same cafe every day, sit there with headphones on, three or four friends would always be working there. It was kind of like Cheers. There were always interesting people to talk to, and my day was broken up into chunks. Any given day I wouldn’t really be on the computer or in one place for more than an hour or two.
And then my day went from that to sitting in a house on my computer all day on Zoom and email. It just made me miserable. When I look at what I love about business — I don’t actually love just doing business. Business is a hack, right? If you’re interested in health, you start a health business and suddenly you can meet all the most interesting people in that world. I’m an extrovert, so I was totally bummed.
I started going on Twitter a lot because I was craving socializing. I went from about 20,000 followers to 170,000. I got completely hooked. A good day would be I have a viral tweet or go on your podcast. A bad day would be I say something on Twitter and get dunked on, or something doesn’t do well. I’d tweet and it would only get 50 likes instead of 5,000, and it would throw my whole day off.
So I got to a point where I was like, “Jesus Christ, this is totally ridiculous.” I’m thinking about Twitter constantly, checking it constantly. On top of that — email, checking stats, stocks. If I went to the bathroom without my phone, I felt like I was going to freak out. Constantly listening to audiobooks, constantly listening to podcasts. No silence.
Andrew: I hit this weird breaking point on August 1st. I woke up and I wasn’t stoked to get out of bed. I wasn’t depressed. Objectively, everything was fine. I just wasn’t excited about anything.
Shaan: What’s that word — anhedonia? An inability to feel pleasure?
Andrew: Yeah, exactly. Nothing would get me pumped, nothing would give me a hit. You know when you go on Netflix and you’re scrolling endlessly for the perfect thing you just can’t find? That’s how my life felt.
So basically, it’s the middle of August, I live in British Columbia, it’s super beautiful, and I said to my wife, “I’m out for the next month. Let’s go off to our cabin, go on some trips, and I’m just going to totally check out.” I set a few rules for myself: no phone, no email, no computer, no podcasts, no phone calls, no social media, no news. I couldn’t even read non-fiction business books. Pretty extreme. I put on my Apple Watch — which has cellular, so if there’s an emergency my wife can call — put my phone in a drawer, and disappeared. Went up to the cabin and hung out with my kids.
The Dopamine Withdrawal [00:05:30]
Andrew: For the first three or four days it felt like there was a bug in my brain. I was so irritable, being a huge jerk. I was slapping my pocket every five seconds to check stuff. I’d be sitting on the beach with my kids and constantly think, “Oh, I need to text this to a friend, I gotta take a photo of this.” Really horrible withdrawal.
But then after three or four days I was like, “Holy crap, this is really interesting.” I started reading fiction books and just sitting for hours. Enjoying a sunset. Taking a silent drive. It’s kind of like if you eat junk food all the time — drinking Coke, having burgers — and then you eat broccoli, it doesn’t taste that good. Your brain is primed for extreme flavors. But if you don’t eat those things for a month and then eat broccoli, broccoli is like orgasmic.
So I did this for four weeks. When I came back to life, it was really bizarre. I’d hear a song playing in a cafe and it’d be like the greatest song I’d ever heard. I’d read some random article and it would be fascinating. Problems I had to solve that would have pissed me off seemed like no problem — I was excited to solve them.
And around that same time I started listening to podcasts again, and I listened to Andrew Huberman’s podcast. He did this deep dive on addiction with Anna Lembke, who’s a Stanford addiction doctor.
Sam: He’s coming on the podcast.
Andrew: Oh, amazing! So I start listening, thinking it’ll be about heroin addiction or alcoholism.
Shaan: So you can learn about other people who have those other bad problems.
Andrew: Exactly — I was like, maybe I can fund the heroin addiction center in Victoria or something. And as I listen, I go, “Oh my god. This is universal.” The neurotransmitter dopamine is the thing that makes you feel craving and pleasure when you do things. She said something along the lines of: if you eat chocolate cake once a month, it tastes amazing and you don’t crave it much. Once a week — still enjoyable, but not as good, and you start having cravings. Every day — your brain literally craves it and you’re in pain until you eat it. And when you eat it, it’s not even that enjoyable. It just makes the pain go away for a little bit.
She compares that to heroin addiction. And here we all are, stimulating ourselves with social media 24/7, constantly taking these hits. The hits become less and less enjoyable. She talked about students at Stanford who were addicted to social media and video games, with no motivation. She basically recommends a dopamine fast for four weeks: no social media, no video games, go walk in silence, drive in silence, have quiet moments. And I realized I’d basically done that for myself, and that’s why I felt better. I was an addict.
Practical Approaches to Digital Detox [00:10:15]
Sam: How do you propose doing this though? I hear everything you’re saying and I think I have the exact same problem. But I’ve got to record this podcast, I’ve got to text people. I mean, I guess I don’t have to. But it’s easy for you to say — you’re a rich guy. For somebody who’s listening, the practicality of detaching for four weeks is hard.
Andrew: Oh yeah. My version of it was extreme, but there are many different forms. It could be as simple as: you just wear your Apple Watch and the only way you text is clumsily on your watch, you take calls on your watch, you do Zooms on your laptop — but you just don’t have that constant 24/7 iMessage coming in. Or maybe you just use Screen Time aggressively.
How do you not eat junk food all the time and have a good diet? Don’t keep junk food in the house. Don’t keep booze in the house. Self-bind yourself. Today, for example, I drove to my office and just have my Apple Watch. No phone. I know if my kids fall down and hurt themselves, my wife can call me — but otherwise I’m not really texting.
Shaan: I’ve consciously picked two parts of my day where I disconnect. I heard two things that kind of shifted my view on this. The first was Naval had this great thing he used to say: the ancient struggle was scarcity — not enough food, not enough water, not enough entertainment. The modern struggle is abundance. We’re overloaded with cheap dopamine.
And literally last night — this is funny — it’s like the addict learning about rehab while shooting up, because it was 3 AM. I had stayed up way too late already. I’m the type where if I’m going to the bathroom without my phone I’m like, “Oh, I’m going to miss out on my entertainment right now. I could watch something, listen to something.” I had literally bought headphones I can wear to sleep — it’s like a soft headband with small earbuds baked in — because I was like, pipe that content into my ears while I’m falling asleep. I didn’t even want to fall asleep. I wanted to be entertained and pass out.
And so I’m listening to Huberman, and he says something that struck me: one way to think about addiction is it’s a progressive narrowing of what gives you pleasure. You are narrowing the things in your life that give you this rush. Andrew, when you dopamine fasted, you started getting pleasure from silence in the car, from the sunset, from fiction books. But before that, Twitter was this cheap, fast, instantaneous, guaranteed source of pleasure. It had narrowed down to just that one thing.
Andrew: It also became more painful over time. When I first started Twitter, it was pure pleasure — so fun. Then over time it took more and more to satisfy me. You build up tolerance, like you would with alcohol or anything else.
Andrew: And of course, you turned your experience into a thread, which probably became one of your most-read posts.
Sam: Of course, totally. Well, and this is the debate, right? Obviously it’s a good thing that we can use iMessage and these devices. They’re a bicycle for the mind, there’s amazing things you can do, you can meet amazing people. But the question is how to use them responsibly. On Twitter I have a one-way client where I don’t actually see the results of my tweets — although in this case I’ll admit I did look.
Earl Nightingale and the Farmer [00:14:30]
Sam: Have you guys heard of Earl Nightingale? He probably died in the ’70s, was famous in the ’50s and ’60s — almost like a Tony Robbins of that era, but more mainstream. He told this famous story on his radio broadcast about a farmer. He went to this farmer’s house right when the telephone got popular. They’re having a conversation and the phone starts ringing. The farmer doesn’t flinch — just keeps making eye contact and talking. About five minutes later the phone rings again. Same thing. A few minutes after that it rings a third time. Earl goes, “Hey, do you need to answer that?” And the farmer goes, “What — that thing? No, no. That’s just there for my convenience. I answer it whenever I want.”
When I heard that story a couple years ago I was like, that’s how I’m going to treat my phone. It is there for me. So I don’t feel guilty about clicking ignore or not replying. This phone exists for my convenience, not the other way around.
Andrew: The other thing is — in the 1950s, if you were an executive at a company, you would have a secretary keeping everyone away from you. And you’d get your mail once or twice a day and batch it. You get 100 letters, half handled by your secretary, you deal with 20 or 50 of them over an hour — write all your responses, done. Whereas now we have a mailman coming to the door every five minutes. You’re doing it in the middle of everything. Batching is incredibly helpful.
And the other thing — people who’ve had family members with alcoholism talk about how if someone gets in between them and the alcohol, they will always choose the alcohol. I think about all the arguments I’ve had with my wife where, if she messed with my dopamine routine — you know, I like to listen to podcasts in the shower, then I like to do x and y and z — if she’d say, “Hey, I need you to go do this,” I would rage. And I just thought I was an asshole or OCD or something. Now being off of that, I’m not raging and getting frustrated in the same way. The addiction stuff really flows through all of this.
Exercise as Disconnect and the Dopamine Stack Problem [00:17:45]
Andrew: I’ve created two windows in the day for real disconnection. Exercise is one. I have a very low urge to check my phone when I’m working out anyway, so it becomes almost 90 minutes of not looking at my phone. I don’t care what’s happening, who’s emailing me, who’s slacking me.
Sam: I don’t look at mine during workouts at all. What I’ve been doing lately is marking down my workout on a notepad and transferring it after, specifically so I don’t touch my phone.
Andrew: Do you guys listen to music while you work out? Because one of the things Huberman talks about is you don’t want to dopamine stack. People work out to experience pleasure and dopamine, but if you start stacking — I watch Game of Thrones while I work out, I get a smoothie after — you start to not enjoy the actual workout. Whereas if you do it for intrinsic reasons, you can train yourself to enjoy it.
Sam: I do listen to music, and I love that. That’s my music-listening time.
Shaan: That’s funny, Andrew — I’m getting between you and your addiction right now.
Sam: He raged out immediately.
Shaan: I’m doing the opposite, actually. Dan Ariely, the behavioral economist, talked about this. He had really bad facial burns and had to apply this ointment that burned and was really uncomfortable. Instead of trying to convince himself through logic that this is good for me, he attached something he loved to taking the medicine. Every time he took it, he’d watch his favorite movie or show. That helped him stick to his routine and actually get healthier.
For me that’s like working out. Working out wasn’t something I found super pleasurable — that’s why I didn’t do it for so long. So I had to retrain myself using music, having a trainer I like hanging out with, doing different types of workouts that are more sporty — so that I would actually get pleasure from working out. I stacked things I knew I loved onto working out so I’d start to love it.
Sam: But Andrew — is addiction necessarily bad? I’ve had alcohol problems, and one way I got off it was I started smoking. Then after smoking I started doing sugar or something. I went to the doctor and she said, “Is it helping you not drink?” I said yeah. She said, “Then just do it.” Some addictions are replacing worse ones.
Andrew: There are a lot of different levels to it, right? Obviously heroin and drug abuse lead to guaranteed misery. But the fundamental question is: is the highest order bit that I’m feeling good on a daily basis, that I enjoy my life? Then cool, whatever your system is, it’s serving you. But as soon as that spirals out — the same behavior might start that way and then over time you stop feeling good. That’s kind of what happened to you, Andrew — at first you were getting great pleasure and rush from connecting with people on Twitter, and then everything in excess has the cons reveal themselves.
Andrew: Totally. The other thing that’s interesting — I’m the kind of person who’s always hacking everything. I was like, okay, if I do the dishes, I found a way to enjoy it: I stack on my podcast, my music, I get a treat after. But recently what I’ve been trying to do is just do the best job of doing the dishes I possibly can, in silence. Almost a meditative practice. The first couple times I did it I was raging. “This sucks, I don’t want to do the dishes.” But after a while of silently doing the dishes, I started really enjoying it. The hot water, washing the pan, doing a good job. Sounds ridiculous, but it’s no different than gardening. It’s just tuning your brain.
AeroPress: Buying a Cruise Ship Company [00:22:30]
Sam: Can we talk about something that doesn’t seem similar but kind of is — Andrew, you bought AeroPress, which is in my opinion probably one of the best companies you could own if you’re trying not to get addicted to fast-twitch notifications. It’s been around forever. You don’t even really sell it online much, right?
Andrew: Only about three percent of sales are online. It’s a pretty low-stress business.
Sam: AeroPress — if you don’t know what it is, it’s a coffee maker. It’s been the same since the beginning, right?
Andrew: Yeah, since around 2006. It’s this thing that looks like a PVC tube. You put some coffee in the bottom, add some hot water, press down, and it makes concentrated coffee. It was started by the guy who made the Aerobie frisbee — he’s a serial inventor. Those neon pink frisbees from the ’80s.
Sam: Amazing product. Can you say what you bought it for?
Andrew: The deal was $70 million.
Sam: And how did you find it? Was it not for sale?
Andrew: Four or five years ago I was making coffee — I’ve been using AeroPress for years, someone brought one into our office about 10 years ago. I looked down at it and thought, “I wonder who owns this.” I started Googling and realized the founder still owned it. He’s this 80-year-old serial inventor who lives in Palo Alto. I sent him an email — looked up his address on Voila Norbert — and said, “Hey, can I come to Palo Alto? Would you ever explore selling?”
He said, “I don’t know if I want to sell, but I’m happy to meet.” I flew down and spent a whole day with him. There’s just so much to love about this business.
Sam: What was he like?
Andrew: Like a really funny old guy. He reminded me a little bit of my grandpa. Hearing aids, clearly loved inventing and coming up with ideas. He walked me through all the different inventions and things he wanted to make.
Sam: Did he actually work there?
Andrew: Yeah, he was really responsible for the product and invention, and there was a president running the day-to-day. It’s such a crazy business — zero marketing. They spend absolutely nothing on marketing. It’s sold in pretty much every single gourmet coffee shop in the world. Walk into anywhere from Blue Bottle down to little independent shops — everyone sells it. It’s a category owner. Like Kleenex or Band-Aid, it’s the category-defining brand. No one searches for “pneumatic tube coffee maker.” They just search AeroPress. It’s literally written on grinders as a setting. So this is an opportunity to buy a category — a way of making coffee — and people are fanatical. There are world AeroPress championships, baristas get tattoos of AeroPresses. It’s totally nuts.
I spent four years trying to convince him to sell. I emailed him every single month for four years. I call it the Dennis the Menace — I have an email reminder in Superhuman and I just kept asking. Finally, over the last six months we negotiated and got it done. The idea is very simple: incredible product, just about selling it in more places. They had no DTC strategy, so we’re coming in, focusing on DTC, keeping the business as is otherwise, and scaling that channel.
Shaan: What you just said is wild to me. When Moiz Ali was selling Native — just a deodorant, one product with a couple of scents — part of the sales pitch for getting more upside in the deal was “imagine if we expanded.” But the way he said it makes a big difference. One way: “There’s lots of room to expand into other product lines.” Emotionally registers as a one. The way he actually said it: someone asked, “What’s the upside here?” And he goes, “Do you know how to write the word Native on other bottles? Could you write it on a shampoo bottle? Could you write it on a toothpaste bottle? That’s your upside.”
When I heard about AeroPress I thought of that. Do you know how to make a website? Because right now if it’s all done through retail and not online — it doesn’t take a genius to make this better. The genius thing was buying it. And that’s your sweet spot, right? You’re not looking to be a genius.
Andrew: There’s this period where factories went from steam power to electricity, and you could go buy a factory and convert it. There was a lot of money to be made in just electrification. This is one of those things — you find a business that’s using a legacy sales process via retail, which we’re going to keep, it’s an amazing advertising mechanism, we love all the distributors. But also: hey, we can sell DTC. Simple insight. And even if we don’t do as great as we think, we’ll still do fine. We’ll have a great business.
Sam: One more point: you bought it for $70 million. What is the annual marketing and advertising spend that created this business?
Andrew: About $20,000. If you include salaries, maybe $150–200K.
Sam: Hold on. How many people work there? Why do you have marketing people if you’re spending $20,000?
Andrew: They do a lot of PR and outreach, but I wouldn’t even call it influencer marketing. The company is like… it’s like Carmex or something. You made it once, and then—
Sam: What do the people do every day?
Andrew: I think there are under 10 employees. They’re managing distributors, making sure manufacturing is good.
Sam: A 10-person company for $70 million. That’s freaking awesome. That’s so cool.
Cruise Ship Investing vs. Speedboats [00:30:00]
Sam: Can you explain the cruise ship investing philosophy? You said something about it.
Andrew: When I talk to any young person — myself included — I really glorified startups. I like to turn these into analogies so they’re easy to explain.
A startup is like a speedboat. It’s exhilarating, it can go anywhere, but at the end of the day you’re driving over waves, your body is getting destroyed, you’re freezing cold, you might hit a rock, you’re always worried about running out of gas. You have to white-knuckle it and pay constant attention.
A cruise ship is slow and steady. It moves on a straight course, so you can pretty much estimate where it’s going. You can make an educated guess you’ll end up in Hawaii versus Antarctica based on its course. You get a comfortable sleep, lots of amenities, very low odds of failure. And best of all, you don’t have to buy the whole boat. You just buy a ticket — a stock certificate.
So when I look at a business, I ask: is this a speedboat or a cruise ship? Do I need to white-knuckle this and need an amazing captain? Or can I just board a cruise ship that’s already doing really well? More boring to ride a cruise ship — no one’s going to give you an award for an amazing Atlantic crossing. But it’s very comfortable and enjoyable.
Shaan: There’s a similar one. This guy Joel Spolsky — Joel on Software — he started Trello and Stack Overflow. Amazing blog, joelonsoftware.com. He’s got this post where he talks about different strategies. He calls it Ben & Jerry’s or Amazon.
Amazon: new technology, very little competition at first. You need to go balls to the wall, go as hard as you can early to grab market share, you’re okay losing money, you have to go fast or you’ll lose. Zero-sum game.
Ben & Jerry’s: lots of ice cream competition already. You can do a good job and this could last 50 or 100 years. But I think the cruise ship analogy is even better.
Shaan: Andrew, you said something about the cruise ship thing — you don’t get to be the hero because you didn’t white-knuckle through the crazy storm and come out the other side, the startup founder who disrupts an industry. And you had a related thing about Twitter: what’s the perfect amount of notoriety? What’s the perfect amount of fame? What are your most up-to-date thoughts on that?
Notoriety, Fame, and the Consistency Trap [00:34:30]
Andrew: This one I’m still figuring out. I don’t really know if I have the answer.
I was sitting at a cafe one day — my wife said go take a couple hours to yourself. I was reading a book. A friend showed up, I started talking to him. About 20 minutes in, this guy sitting to our left goes, “Hey, I’m really sorry to interrupt, but I heard you on My First Million. I’ve got a business over in Vancouver.” And that was cool — and I’m sure you guys have that too, every once in a while.
Sam: Is that a real story?
Andrew: Yes, 100% real. He runs the best gourmet coffee shop at UBC — a big university in Vancouver. It’s called Bulldog Coffee. Anyway. What was going through my head after that was: oh my god, what did I say? Here’s this person who heard everything I was saying. I don’t think I said anything bad or overly personal, but there’s this sense of a loss of privacy. And not only that, but you have to be consistent. If I go on this podcast and say I’m about x and y and z, every time I talk to someone, if I change my mind or want to be a different person, they kind of call you out.
And there’s commitment bias. I talked about a sugar-free bakery thing I was doing, and we ended up getting shut down — we weren’t legally allowed to use a key ingredient in Canada. But I didn’t shut it down for two months longer than I should have, because I’d made a public statement to everyone: “Hey, look at this awesome thing I’m doing.” I felt ashamed to admit it wasn’t working.
There’s this great Bill Murray quote: “If you think you want to be rich and famous, try being rich first and see if that covers it.” I think in film you’d want to be like the Coen Brothers — no one knows what they look like, but if they’re at the Oscars, they’re total ballers. And Daft Punk — they’ve got the best job. They don’t even have to show up. They probably each make $10 million a year from concerts, and they could be anyone under those masks.
Sam: I get stopped probably once or twice a week.
Shaan: More of the cool ones for me are secondhand stories. My trainer came to me the other day and said, “I met these two guys in the gym, they’re 21, 22 years old, and they were telling me ‘You gotta listen to this podcast, we’re so fired up, we’re going to quit our jobs and do the stuff.’” And he’s like, “What’s the podcast?” and it’s My First Million. He’s like, “Bro, that’s my buddy.” Those are the moments that light me up.
And the serendipity — Sam and I were riffing on ideas, and one of them was DTC pregnancy health: how do you build a super baby using supplements and blood work? Now I’m in a partnership with this woman named Katie Dewhurst and we’re working on this business together. I never would have met her without the podcast. The pros are huge.
Andrew: But then there are the odd downsides. And for you guys, I’d assume you’re probably addicted to your podcast stats, right?
Sam: I’m more addicted to Twitter. I was like, I’ll be slick and turn off notifications, but what I do is search my Twitter handle and type “latest” so I see my face. So that’s… dumb.
Andrew: Podcast is not designed to be addictive, right? It’s slow and steady, compounding, with no immediate feedback. You don’t get comments after every episode. That makes it suck in a way, but the good thing is it’s very zen. Of all the things I’ve done — newsletter, Twitter — I like fade out because I don’t like what it does to me. I think one of the most toxic things you can do is care too much what other people think of you. And that’s fundamentally what the loop of social media is: you post something, other people react to your photo, what you look like, what you said, what you thought.
Sam: Although, Andrew — I’m a fitness influencer now. I’ve got about 4,000 followers. I started posting on Instagram constantly, kind of as a joke but kind of not. I wanted to get very fit this year, I’d hit a plateau, and I was joking with Shaan — I’m just going to post constantly and change my identity to become a fitness person. And it’s made me not eat certain foods, because in my head these people are expecting me to hit this weight. Is that unhealthy? Kind of. But I’m getting a great result.
Mimetic Desire and the Wanting Book [00:41:00]
Andrew: We got to talk about this book I read called Wanting. Have you guys heard of it?
Sam: No.
Andrew: Have you ever heard of Peter Thiel talking about mimetic desire, René Girard?
Shaan: I buy the books and I can’t read them. They’re so dense. David Perell did a bunch of articles and even then it was too academic.
Andrew: Finally one of my friends who’s super into Peter Thiel gave me this book Wanting, and it was kind of a revelation.
The idea is basically that you want the things that are modeled to you by other people. You’re at a bar with a friend, there’s a martini — you go, “Maybe I do want a martini.” That’s a meaningless example. But what if your friend just raised a round from Sequoia? You start asking yourself: why didn’t I raise from Sequoia? Why does his startup have more employees? Why didn’t I get that job title? He has a sailboat — why don’t I have a sailboat? He moves to Brooklyn — why don’t I live in Brooklyn?
When you surround yourself with peers, you start competing with them and wanting those things. I see this in my own group of friends: when one of us buys a new car, within a year we’ve all bought a new car.
The book talks about thin desires — extrinsic things coming from the modeling of others, like wanting a Rolex because your peers value Rolexes. And then there’s thick desires — intrinsic, they come from inside. You enjoy working in your garden. You don’t need to tell anyone, you don’t post about it, it’s not part of your identity, you don’t do it to impress anyone. It’s just something you quietly enjoy.
The big thing is coming up with: what are my thick desires? What’s real versus what comes from wanting to be like my heroes or my friends? Because if you’re not careful about pruning this, you will become it. If you spend too much time around people who want things you don’t actually want, you will still desire and achieve those things.
Shaan: Love this. So you read the book — what did you take away? Who are your models?
Andrew: Like, am I jealous of Jeff Bezos? No. Jeff Bezos is not someone you really compete with. He’s off in this celebrity world. The people you compete with are within your bubble. It could be each other — us three. Anyone on Twitter in business: the Morning Brew guys, whoever. It doesn’t matter if you like them or not. You’re in a memetic competition.
Shaan: When I see Sam’s fitness post, I work out harder that day.
Andrew: Exactly. And he now values health, so if you want to be healthy, hanging out with Sam will probably make you healthier. Good outcome.
There are so many different bubbles. If you live in San Francisco, everyone wants fundraising and valuation, who your investors are. In New York it might be wealth, your art collection, your fashion. In LA: what awards have you won, where do you get restaurant reservations? Athletes: Olympic medals. Chefs: Michelin stars. Comedians: Netflix specials.
The way to figure out who your models are is to ask an odd question: who do I not want to succeed? It might be that guy on Twitter who you’re friendly with — everything’s fine — but he bothers you, he’s maybe a little ahead of you, has 10,000 more followers, and you just don’t want him to succeed. That’s probably who you’re in mimetic rivalry with.
The real question is: how do you align with people who will lead you down a path of mimetic copying that will actually make you happy? Spending time with people who want things that are your thick desires — health, safety, gardening, whatever it is. And then: how do you opt out? That’s pruning. What do you read, who do you listen to, who do you spend time with?
Andrew: I’ve idolized Warren Buffett forever, but when I think about what Warren Buffett actually does in his day — he’s a guy who can sit there and read annual reports all day. I would kill myself. I have no interest in doing that. So I have to be careful not to over-index on Warren Buffett.
You can also opt out entirely. Dave Chappelle moved to Ohio — just a redneck in a small community. For me, I live in Victoria. I’m not as exposed to this as other people.
The Michelin Star Chef and Removing the Ticker [00:47:00]
Andrew: There’s this great story of a Michelin-star chef. The ultimate for chefs is you open a restaurant, you get a Michelin star. This guy — Sébastien Bras — did that. All he wanted was a Michelin star, and he got it. And when he got it, it didn’t make him happier. He just wanted a second star. He got a second star, still not happy, and he lived in fear of losing it. They can just come inspect you unannounced — tablecloth not perfectly clean, food a certain way, you get rejected. So you end up living by these arbitrary rules that don’t actually make you happy, fighting for something that’s not what you actually want. This guy just said: “Michelin, I want you to remove my star. Take me out of the guide. I’m out.” That takes brass balls, but it’s possible.
Andrew: Why did you mention Readwise on your notes document?
Sam: I just read all sorts of random stuff and make a huge impact on myself but then forget everything. So I use Readwise — my Kindle highlights get emailed to me once a day at random. Spaced repetition. Every week or month, these ideas boomerang back to me.
Andrew: When you’re reading, do you just read book after book?
Sam: Yeah. Although I’m thinking — if I find a book that has a ton of learnings, I should probably reread it every handful of months. Do whatever it takes to really understand and grasp it. Not just go from thing to thing to thing.
Andrew: Do you know the Feynman Method? You read the thing and then you teach it. You can’t truly understand it until you teach it. Coming on this podcast and summarizing what you’ve learned in a cogent way — that’s how you really hammer it in.
Sam: That’s how I studied in college. I figured out pretty early that the way to get better grades without spending hours in the library was to quickly skim the material and then lead a study group where I’d teach it. I was a horrible teacher for the first hour because I barely knew the material — but by teaching it, I remembered what I knew and quickly figured out what I didn’t. I studied half the time as other people and retained it better, because they’d just keep re-reading notes. They never tried to articulate it off the top of their head.
Andrew: It’s such a hack. I used to run this thing called the Anti-MBA — a weekly book club. We’d read a book a month, divide it into quarters, talk about a quarter each week. I’d be leading 10 or 20 people through it. I was mastering every book I led. You could also do it through blogging.
The Trap of Constant Optimization [00:52:30]
Shaan: One thing I’ve seen — and I’m trying to stop doing this — is the constant optimization. Andrew, you’ve got Readwise set up to email you highlights. Sam’s like, “I should reread the important books.” Old me would have been like: “Dope, love that, that’s my solution to this underlying problem.” I’d keep seeking these solutions — new hacks, new optimizations, new techniques.
The one realization I’ve had — and my trainer really drilled this in — he would say something wise during a workout and I’d run to my notepad to write it down. I wanted to remember the nugget, tell other people, say it on the pod. My head was actually thinking: “This is my next hit, my next tweet, something that’s going to be great.” Lame to admit but true.
He told me: “You won’t have to write these down.” I go, “What do you mean — I’ll forget.” He said, “You won’t feel like you lack something, so you’ll stop trying to catch everything and grab everything and learn the next new thing. You’ll realize you already know the answers.”
It’s like a diet book. You can keep searching for the next fad diet — Atkins, slow-carb, carnivore — cycling through, trying to find the next solution. But you kind of know the answer: don’t eat too much, eat real food, mostly plants. Three lines. That’s it. But instead of sitting with it, you want it to be more complicated. You want there to be more to go learn and find. Get the app that does intermittent fasting, put the ketone drops in your drink, wear the glucose monitor patch — all these optimizations.
I’ve found a lot more peace in getting rid of that underlying feeling of lack that’s causing you to constantly chase the next method.
Andrew: That really resonates. Routines are great, best practices are great — but they end up creating conditions under which you can have a good day, and if you don’t follow the conditions, your brain starts saying it’s not a good day. I didn’t get my workout in. I didn’t do my cold plunge, my Tim Ferriss tea, my Evernote routine, my gratitude journal. There are endless things. For me: how do I not check my Oura Ring, how do I not check my blood glucose?
Shaan: They’re all tickers. They’re tickers for life. And tickers make you miserable. Look at a stock ticker, look at KPIs, look at revenue hour to hour — you’re miserable. You shouldn’t have those for your life.
Andrew: And I should say — it’s bad for business for me to say this, because this podcast and all my content is about optimizations, hacks, shortcuts, ways to be better. So I’m juggling two things that are almost in complete opposition. I still wake up and swipe over to check the Bitcoin price, and when it’s red I’m starting my day with a tiny jab, and when it’s green I start with this little delight that I don’t control. My first mood is up to crypto prices. Silly.
Who’s This Episode For? On Authenticity and Audience [00:57:15]
Shaan: Sean, what do you think people are going to think of an episode like this?
Andrew: I sometimes get nervous talking about this stuff. I don’t want to pontificate. I don’t want to act like my way is necessarily better than anyone else’s. I get nervous about having a guru productivity vibe. And then I also think — these people just want money-making schemes, let’s just give it to them.
Shaan: I think two things. First, you’re not giving the audience enough credit. The people who really listen to this podcast — they know this isn’t just money-making schemes. We’re shooting the shit about business stuff. We’re business nerds. That’s what they like. When you get through the door, you realize that’s not really what it is.
Second: this feeling of “what are people going to think of this episode” — I’m trying to rid myself of that question. It comes up less and less. Because: who are my customers? The people that love what I do. Period. If we’re talking about something we’re interested in, they’re always going to be into it. Keep that as the method. Then I don’t have to worry about did they like me, is this good, is this bad. I liked what we talked about — I don’t need to worry about it anymore.
Sam: I go back and forth. Sometimes I think, “I’m going to do whatever the hell I want.” Other times I think, “I’m here to serve others.” It’s a fine line.
Andrew: One of the things on the list is being you — that is the service. Being you, publicly, transparently.
Andrew: Lately I’ve been watching all the Dave Chappelle standup on Netflix. If you watch the first one, it’s kind of generic dirty standup. As you watch them, they get more introspective, darker, longer stories, different style. Cool to see someone evolve and show deeper emotional range.
Look at Rogan. Do you think Rogan gets on the pod every day and thinks, “What do the people want? How do I make this conversation entertaining for them?” It seems like: no. He’s just having a conversation with somebody he finds interesting. The format broke a bunch of rules — one day he’s talking to Neil deGrasse Tyson, the next it’s an MMA meathead. And Lex Fridman — talking about the nerdiest subjects in a monotone voice, not charismatic, not talking about pop culture. He found the balance of doing what’s interesting to him in his normal personality.
Sam: But also, Rogan’s a comedian. Comedians are inherently the neediest people — they get on stage, they need the audience to laugh. He’s not not human. He breaks rules in format but he’s still got the same insecurities. I don’t buy that you don’t care. I think everybody cares.
Andrew: Oh totally. We all give a shit how we’re perceived. I made that tweet about my August breakdown and a friend messaged me: “Are you sure you want to tweet that?” He’d gotten messages from people saying, “Oh my god, Andrew’s having a mental breakdown on Twitter.”
Sam: Is that why you tweeted it?
Andrew: Yeah — that’s exactly why I tweeted it. It got lots of traction and lots of nice notes, but it’s scary putting that stuff out there.
Sam: I would hate that interaction — “Are you sure you want to tweet that?” That’s like a double down for me. I just spent an hour writing that.
Andrew: You know what, that’s a valuable service from a friend if they actually think that.
Sam: Yeah, and if a friend — like my friend Jack — replies on Twitter to argue with me publicly, I text him: “Jack, don’t argue with me in public. You defend me out there. What are you doing?” He always does it. One time I tweeted out our podcast numbers and he was like, “But Megaphone is wrong” or something. I’m like, “Jack! Just text me.”
Screen Time Numbers and Andrew’s Apple Watch Life [01:03:30]
Andrew: Anyway — how often are you holding your phone? How much are you using it?
Andrew: I’m down from six hours a day of screen time to just over two hours. On random days I’ve just been taking my Apple Watch. If I have a Zoom call I’ll take my phone, but otherwise just the watch. It’s strangely freeing, because you can still see texts and get calls. But texting on the watch is this stupid scratch-out or Siri thing, so it’s just not fun to text. So I just don’t.
Meeting Steve Jobs at 15 [01:04:30]
Sam: Andrew — you met Steve Jobs. Tell me what happened.
Andrew: A lot of people don’t know this, but when I was 15, my very first business was a website with an incredibly embarrassing nerdy name: MacTeens.com. Me and a kid from Hawaii and another Canadian kid. We made this tech news website, started writing reviews and news, started getting a lot of traffic, breaking Apple rumors.
I ended up getting invited to go to Macworld as a member of the press and to this tour of the Apple Store in New York when it was brand new — the first one, I think. I walk into this tour thinking we’re just going to get a PR flack. I’m standing outside waiting and a limousine rolls up. It’s Steve Jobs. He gets out and shakes my hand. I’m 15. The guy’s my hero. I’ve read every biography of him. I’m a quivering mess. And I spent the next hour — me and like five other journalists — getting toured around the Apple Store with Steve Jobs.
Sam: What was his presence like? How did he treat people?
Andrew: He was in Steve Jobs PR/Macworld CEO mode, so he was incredibly polished. I remember he was talking about the CD burner in the 17-inch iMac and I was enraptured — it’s a standard OEM CD burner, right? But he’s making it sound like the greatest thing in the world. The reality distortion field is obviously real. It was cool — on the bucket list.
Sam: Did you read this story that went viral on Twitter? This guy tweeted out that he was trying to sell his company to Steve Jobs and he blew the deal.
Andrew: No. What happened?
Sam: The CEO of iLike — a music discovery service, popular in the early startup days. Apple was interested in acquiring them. He gets a meeting with Steve Jobs. Starts off a little rough because he’s so nervous. But they hit their groove in the presentation, hit the demo — first the exec suite Wi-Fi was down, but they recovered. Steve was asking questions and clearly digging it.
At the end, Jobs says, “Look, I think you guys are great, I’d like to buy your company. I’ll talk to Eddie, he’ll handle the details.” The guy doesn’t want the meeting to end there. He asks: “What range would you be thinking about for price?” Jobs gets more serious. He asks: what’s your revenue? How much did you raise? What was the valuation at your last financing?
The guy says: “We’re pre-revenue, pretty small. We raised at a $50 million valuation and we’ve added like millions of users since then.” Jobs says: “We’d probably acquire it for $50 million.”
The guy goes from this high — Steve Jobs just said he wants to buy my company — to: oh shit. We’ve been working for two years since the last round, we’ve grown all these users, and I’d have to go to my team and be like, “Hey, we’ve created essentially no value.” So he doesn’t want to just leave it there. He says he doesn’t think his team or investors would find that acceptable. Jobs says something like, “We’ll convince them.” The guy presses: “I think we’re worth $150 million. Actually, I know we’re worth $150 million.”
Jobs pauses. Then: “Do you have another offer? Has someone offered you $150 million? Is that how you know?” The guy pauses. Jobs says, “You’re a liar.” And basically walked out. They tried to salvage it through Eddie Cue, but Jobs called later and said: “I don’t trust you. You overplayed your hand. We’re not doing this.”
Andrew: Oh, I love that. That is awesome. Who wrote that?
Sam: This guy Ali Partovi — his Twitter handle is @aparTovi. His company, I think, was soon acquired after that Apple released the iTunes Genius sidebar, which was a ripoff of their thing. Facebook copied it too. They sold the company for a loss within a year.
Andrew: The other good one is Drew Houston going to meet with Apple about Dropbox, and Steve Jobs just starts saying, “Feature, not a product. You’re a feature, not a product. We can just rip you off.” And in some ways Steve Jobs is right. But Drew Houston went on to become a billionaire and build a great public company.
Sam: I love stories where Steve Jobs is wrong. The guy was brilliant, but also — I was thinking the other day about that famous quote where he says to the Pepsi CEO, “Do you want to sell sugar water your whole life, or do you want to come change the world?” And part of me is like: badass, great job Steve. And then I’m like: dog, what you’ve just created is candy. If I’m supposed to hate Zuckerberg, I should dislike you too. You’re selling the crack pipe, he’s selling the crack. What’s the difference?
So whenever I hear these stories about him being arrogant, I’m like: yeah you’re awesome and you’re always right, and also: you’re a dick sometimes.
Andrew: I was a CEO and I could never bring myself to say something like that. “Do you want to come change the face of publishing forever?” You just sound like such a douche. But you talk to most Silicon Valley CEOs and they say something like that.
Shaan: Part of me is envious — wow, you actually believe that you’re doing something that important. And part of me is like: you’re full of it.
Endurance, Shackleton, and What Makes Great Men [01:12:00]
Sam: I just read this book called Endurance. Have you guys heard of it?
Shaan: I know the cover. I’ve never read it.
Sam: If you never want to feel like your life is hard, read that book. I couldn’t put it down.
In the early 1900s it was called the heroic era of Arctic expeditions. They had steam engines and combustible engines, but still sails. No radios. These guys would sail from England all the way down to Antarctica to figure things out, map the world. This guy Ernest Shackleton led an expedition of 30 people, they got stuck in Antarctica, and it’s the story of their two-year expedition to survive.
What I learned: the people you’re leading mimic the behavior of the leader. For a while I was against this “we’re gonna change the world” thing, and I thought I should be vulnerable and let people know when things aren’t going great. But after reading that book I’m like: no, you gotta convince everyone it’s gonna be okay no matter what.
Andrew: It’s an amazing book. When I get stressed out at work, one of the things I love is watching Alone — have you seen it? They dump people in the middle of nowhere in a competition to see who can survive in the wilderness the longest by themselves.
Sam: How long do they last?
Andrew: Some people make it three, four, six months. A lot are out pretty quick. Somebody cuts their leg open with a hatchet. I watch it and I just feel so relaxed. I’m cozy on the couch and warm, and it makes you appreciate how comfortable our lives are. The Shackleton book is exactly like that. It’s riveting. I can’t believe people survived that. And it made me feel thankful, and showed me that in order to be a leader, you do need to convince people — and yourself — that everything’s going to be okay.
Sam: When I read that I thought: I don’t want to be that good of a leader. I’m not willing to do what that guy was willing to do.
Elon vs. Bezos: Memetic Rivals at the Top [01:16:30]
Shaan: Something funny just happened on Twitter. Speaking of distractions and mimetic models — Bezos just tweeted this thing. He posted a photo of a Barron’s cover from around 1999. The headline says “Amazon.bomb.” Picture of Jeff Bezos’s face on a bomb. The title: “The idea that Amazon’s CEO Jeff Bezos has pioneered a new business is silly. He’s just another middleman and the stock market is starting to catch on. The real winners on the net will be firms that sell their own products directly to consumers — just look at what happened to Sony and Dell. That’s what’s going to happen to Amazon.”
Bezos was basically saying: people told us we were going to fail. Today Amazon is one of the most successful companies and has revolutionized two entirely different industries.
And then Elon Musk replied with just a silver medal emoji — number two.
Sam: You gotta give him — Elon is currently richer than Bezos.
Shaan: If it’s about space, that’s not douchey. If it’s about the rich thing, that’s douchey. But it’s so funny because these guys are in a memetic rivalry. To us, Jeff Bezos isn’t really our rival. It doesn’t hurt us personally when Jeff Bezos wins a little bit more. But for those two, these are their peers, they’re in competition.
Sam: I do want to see Elon lose a little bit — he gets too smug with his helps, gradius, be smart thing. Because he is, in fact, amazing. But how baller is that tweet?
Andrew: In order to be that successful, you have to have some kind of personality disorder. You look at Musk or Bezos — if you read more about Bezos, he’s apparently a really difficult person to work for. These guys are complicated. And a hundred years ago you just wouldn’t know. There wasn’t Twitter. This would all go on behind the scenes.
Sam: I don’t even think it’s that complicated. Musk is really successful because he’s incredibly smart and has a complex because his father probably didn’t love him. It’s probably quite simple. But it works.
Andrew: There’s this quote I always say: great men are bad men, or great men are sad men. In order to be great you have to do things others think are bad. Or there’s a sadness or personality disorder driving it — why else would anyone choose to do what Shackleton did? Why would anyone choose that unless they have deep trauma?
Shaan: Andrew, your Obama example was a little extreme — I think it’s more like: Elon Musk is a great inventor and businessman, that doesn’t also mean he has great views on vaccines, or that he’s a great husband. We can praise someone for a specific aspect without saying they’re perfect.
This is like the Jake Paul thing I did — I said Jake Paul is a great marketer and self-promoter. People were like, “Yeah but he’s accused of assault on this girl, he’s a jerk.” I said: did I say he’s my hero? Did I say he’s a great boyfriend? I said he’s a great self-promoter and you can learn from that.
Andrew: I appreciate that. Anybody you praise for being awesome or call out for being bad — you’re not saying they’re all great or all bad. They’re great in ways and bad in ways. You can like how he builds cars but not how he treats his marriage.
Sam: Yeah. Exactly.