Shaan does a trip report from a real estate conference in LA, walking through 21 micro-notes he took. Topics range from a networking technique called the “low status move,” to why the richer someone is the weirder they tend to be, to dressing well, small luxuries like great socks and towels, and a conversation with Mike Posner that covers his full three-act life story.
Speakers: Shaan Puri (host), Sam Parr (host)
Trip Report Format and Micro-Memories [00:00:00]
Shaan: All right, we are going to do an episode that people really liked before. It was a trip report. I did one when I went to Austin. I just went to LA and I wrote down a bunch of notes. Most people when they travel don’t do this, but I call them “micro memories” — I just write down one to three words that wouldn’t make sense to anybody else, but there’s a story behind it for me. Some insight, some story, some crazy thing that happened. I write them down all trip.
What I did this time was I just published them on Twitter and said, “Hey, here’s all my notes — ask me about any of these.” I wrote down 21 things. Why don’t we try that, Sam? Why don’t we take this list of 21 and you just pick numbers you think are interesting, and I’ll explain the thing.
Sam: By the way, when you take these notes, where are you taking them? On your phone? You just have a running notepad on your phone?
Shaan: I have two. I have pen and paper that I take everywhere I go, and then I also have my phone in case I’m just not there. Apple Notes, nothing fancy.
Sam: And you discard the notepad after, or do you refer back to it constantly?
Shaan: Most people come home and they unpack their bags. I basically just unpack my notes. My bag is actually still sitting over there — it’ll be there for three months. But what I do is the very next day, instead of saying “Oh, I’ve got to catch up on work and emails and Slack and all this stuff,” the first two hours I basically just take my notes, type them out, and try to squeeze 20–30–40% more juice out of the trip just by reflecting. Like, “Okay, what was that story? Oh, I should follow up with that person. What’s the takeaway there? How am I going to implement that? Oh, I need to share this story — let me write it and make sure I send it to that person.” I take a couple hours first thing and basically unpack my notes.
The Low Status Technique for Becoming High Status at a Conference [00:02:30]
Sam: All right, tell me about the low status technique for becoming a high status person at a conference.
Shaan: All right, so I went to Reconvene, which is a real estate conference, and I met this guy there that I really liked right away. Then I noticed that he was probably the most popular guy there. There were maybe 150–200 people there. He was my favorite, and I think he was everybody’s favorite just based on the reactions I got. I was watching him and thinking, “What is this guy doing that has made him everybody’s favorite person here?” I think that’s what we all want — we all want to be liked, especially when we go to these big public events with strangers.
He’s a big fan of the pod. His name is Will, and he’s got a Twitter account called Student Rent Pro. Basically what he does is he owns a bunch of rental properties — student housing in South Carolina. Frat houses, sorority houses, just students living together. Bootstrapped it, no outside investors. As soon as I got there he makes a reference to the pod from like three years ago. He introduces me to somebody and goes, “Oh, this is Shaan, he’s real good friends with Orlando Bloom” — remembering some story I told. I was like, wow, that was a deep reference.
So I’m watching him and I go, “How come everybody here loves you?” And he goes, “You know that thing when Hasan Minhaj came on the podcast? He shared this insight about comedy.” This was before me and you were going to get on stage — we were doing our first live show in Vancouver. I had texted Hasan a picture of like 2,000 people in the audience and was like, “Dude, give me some tips. How the hell are we supposed to entertain this crowd? We’re podcasters.” And he said two things. First, start by talking about things you see right there — make a reference so it’s like, “I’m here with you right now, you’re not getting my usual spiel, you’re getting me here right now.” Presence. Second, comedy is a low status art form — meaning self-deprecation. Make fun of yourself, call yourself out, poke fun at yourself. That’s how you connect with people.
Will goes, “I stole that. I stole that hard.” He’s been doing it ever since he heard that. So at this event, somebody would say, “What do you do?” And he’d be like, “Oh, I do the hardest form of real estate that will pay you the least amount of money, so you don’t even want to talk to me. You should go talk to him, he’s awesome.” And somebody’s like, “Wait, what does that mean?” And he’s like, “I do student housing.” But then he’d always make it about you or somebody else. If anybody gave him a compliment — even when I called him the favorite guy there, he was like, “Oh, thank you so much for saying that. I’ll be sure to disappoint you next time.” Just a master of this low status thing.
He said he does the same thing on Twitter. Everybody at this conference on Twitter just brags about their returns, brags about how awesome they are, brags about their method. He does the exact opposite. He’ll go on there and talk about how today some 19-year-old’s toilet needs fixing. “Wish me luck.” He’s always talking about how hard his business is, how he doesn’t envy himself. He shines a light on the worst parts and the uncertainties. But he goes, “I’ll tell you what — I think I could out-raise everybody here if I wanted to, because what I’ve been doing on Twitter has built a lot of connection and trust.”
And when I watched him at the conference, he was doing something that Ben LeBlanc is a master of — he realized that the way to build value at a conference is not to puff your chest out. What he would do is connect any two people to each other, get the goodwill of having made that connection, and just keep doing it. He’d be like, “Oh, this is Shaan — he’ll never tell you this but his podcast is a huge deal. And Shaan, this guy — we call him the multifamily king of Dallas.” He’s like the Flavor Flav of the conference. Just hyping people up, connecting people, giving everyone this hyperbolic intro where he’s your hype man.
What that does is create this enormous glue and goodwill. You need people like that at a conference. But also for him — he ended up being the high status guy. He’s the guy everybody loved, the guy everybody knew, and the guy nobody felt on the defensive with. Because people felt they could be real with him, they actually formed real connections. I thought it was really awesome to see in person.
The Richer the Guy, the Weirder the Guy [00:10:00]
Shaan: Two things: dinner with millionaires, and “the richer the guy, the weirder the guy.”
Sam: “The richer the guy, the weirder the guy” — that’s an obvious one for me.
Shaan: So what we do with these events is we stack meetings with a bunch of interesting people who live in that city. When we go somewhere, Ben will say, “Here’s a bunch of friends or people we loosely know — who do we want to hang out with and how busy do we want to make this trip?” One of the things that really stood out was: the more successful the person, the richer the guy, the weirder the guy — with really no exceptions during this trip.
And when I say weirder — weird hobbies, weird marriages or relationship dynamics, just really weird social skills. What I realized was that I always assumed by default that people are just normal, chill people. That was my default assumption. And I realized I really need to stop making that assumption, because it is way, way wrong when it comes to these outlier successful people.
I thought about it — like, are they successful because they’re weird, or are they weird because they’re successful? I think there’s a bit of both going on. They’re successful because they’re weird in that they were willing to be unconventional. They didn’t just go get a job. They didn’t look at some industry and assume it was well-run. They actually disrupted it, they grinded for 10 years taking no salary. So because they were willing to be unconventional in their career, it really shouldn’t surprise me that they’re also unconventional in their marriage and unconventional in their hobbies.
Sam: What’s an example?
Shaan: I don’t want to put specific people on blast — they listen to the podcast. But I mean, you’ve seen this in San Francisco.
Sam: I have. I think those particular people tend to be on the coast — LA, San Francisco, New York. I know a handful of people worth nine figures who live in Missouri where I’m from, and they are shockingly actually normal. I think if you’ve gotten extremely wealthy at a young age and you live in one of these cities, you should just assume they’re gonna be a freak.
Shaan: Yeah. There are also just rough social edges. We were at a breakfast and there were two people there who didn’t know each other. I was like, “Hey, maybe you guys just introduce yourselves.” Sam, if I said that to you, what would you say?
Sam: I’d say, “Hey, what’s going on — my name’s Sam. I live on the East Coast, I work in the media industry, I do a podcast, and I’m super into health and wellness.” You say your name, where you’re from, what you do, and maybe one hobby or thing you’re really into.
Shaan: Totally normal, chill thing to do. This one guy starts with his name and finishes two minutes later with his company’s EBITDA and the terms of their recent acquisition.
Sam: I was like, what is going on.
Shaan: I think rich people are just really, really out of touch with what they’re willing to share — they overshare. But I think that happens to you and me too in a way. If they listen to the podcast and realize we talk about numbers a lot, he was probably trying to connect by doing what he thinks is just what you talk about.
Sam: Yeah, and it wasn’t bad — it was actually really fascinating. I did note like, wow, that’s not a normal thing to do. But I enjoyed it in the moment. The other person at the breakfast did the same thing. I was like, okay, we all just went deep really fast. Weird, but cool in its own way.
Shaan: So yeah — the richer the guy, the weirder the guy.
Dressing Well vs. Dressing Comfortably [00:17:30]
Sam: All right, what about dressing well versus dressing comfortably?
Shaan: Okay, this is right up your alley because I think you are on a big “dressing well” kick. Not displayed today with your white T-shirt, but right now this is like a fascination for you.
Sam: This is an $80 t-shirt, Shaan.
Shaan: Is that an $80 t-shirt?
Sam: It’s the t-shirt the dude Jeremy wears in The Bear. So it’s called fashion.
Shaan: Nothing like buying an $80 t-shirt and having somebody say, “Is it an $80 t-shirt?” Makes you feel great. I apologize. Fashion.
Sam: Yeah, you’re speaking a language I don’t even know. That’s the problem — I can’t even recognize it. I paid $80 for this t-shirt, so I know a thing or two about fashion.
Shaan: All right, so obviously when you go to Los Angeles you see a bunch of beautiful people, and I started paying attention to it. On the flight I was like, “Man, people really dress beautifully for this flight. This is really cool.”
I remember Paul Graham wrote this essay called “Cities.” He says every city is whispering something in your ear. San Francisco is whispering, “You’re not ambitious enough — go bigger, launch rockets, artificial intelligence.” New York tells you, “You’re not powerful enough — you’re poor.” LA basically whispers, “You’re not hot enough.” This is why people are injecting all kinds of stuff into their faces and lips and everything. That part is a bit of a turnoff for me. But I do appreciate the “dressing well” component of “you’re not hot enough.”
The funniest part was I went and our buddy Suly lives in LA right now. I saw Suly a few months ago when he was living in San Francisco. The guy transformed, dude. He went from SF startup-scrappy style to cool-guy LA chic — and not even in a try-hard way. Just very casual, but well-dressed casual. I was so inspired. “Wow, this is my same friend, two different cities, comes across two different ways just by a couple of choices.”
I literally was like — he was explaining something to me and I just looked at his tag, took photos of his shirt while he was wearing it. “I’m buying this exact outfit. That’ll be my starting point.”
What I realized was I’d had this false choice in my head: dress comfortable or dress nice, one or the other. When I saw him I was like, “Oh, he’s comfortable AND well-dressed.” Duh. That was a false choice. Pretty easy to change.
I also remember 10 years ago I hired a stylist in San Francisco to come to my house. She threw away all of my clothes, took everything out of my closet, and took me shopping for one day. We bought a whole bunch of new stuff — it was like three grand to do it, and it was great. But that was 10 years ago. Since then I’ve gone back to my old ways. I’ve copied many things from Suly in life — mostly business stuff. This is something else I’m going to copy from him: do a very simple upgrade to style.
Sam: Do you know why you thought dressing well is the opposite of comfortably? It’s just because your clothes didn’t fit right. If you wear really nice clothes — as much as a tie and a nice shirt — if it fits well, it’s not uncomfortable.
Shaan: I think that’s right. Do you value art at all? Like, does art talk to you? Do you ever feel inspired by beauty?
Sam: Not paintings. But things that are beautifully simple in design, yeah. A lot of furniture or interior design — a space. If I walk into a space that’s got a certain vibe, I just can’t pay attention to anything else in that moment, because I know that same space with just a different set of lights and furniture and plants would feel completely different. Same shell, but somebody created this vibe.
Shaan: I agree. I like architecture and the energy of a room. For years I thought art just meant paintings or sculptures, and I don’t find inspiration from those things. So I thought, “Architecture, clothing — that’s not art, that’s a waste of time.” Then I kind of realized — no, it’s actually just as important as art. It’s not a waste. When I started giving into that feeling, I realized this is what speaks to my soul. I should give into this. It’s worth the effort. This isn’t simply utility — it can also inspire me, sing to me a little bit. Once I realize they’re all related to self-expression and it’s all art, it changes my perspective.
Music is probably the easiest one to appreciate. And instead of saying “Well, I’ll just pay someone to do this,” I realized — no, I want to learn what these things are communicating. In a weird way, I don’t want to just phone it in with art. I want to figure out what makes beautiful art, and what language do I want to speak when I’m communicating through it.
Sam: I’m also probably the only sucker that bought two NFTs because I was like, “Oh, that’s beautiful art.” And I didn’t mean it as a cover-your-ass “I’m just trying to get rich.” Was that the holographic Kobe thing?
Shaan: The Kobe floating-into-heaven one?
Sam: That one, and there was another one — just a strawberry. I was like, “Wow, this is beautiful.” I bought this strawberry NFT that is currently worth zero. But in my heart it’s still worth something.
Little Luxuries [00:29:00]
Shaan: All right, let’s do one or two more things. Which ones do you think are interesting?
Sam: I think “little luxuries” is a good one. And Mike Posner is a good one.
Shaan: All right. Little luxuries. We meet a bunch of people. One of the things we noticed was, we’d have a meeting or lunch or hang out at someone’s house who was super wealthy — and we noticed that even if this person has like 10 times the net worth we have, they don’t have 10 times the better life. They don’t even have maybe two times the better life. I actually don’t think there’s really any link. And I don’t mean “better life” as in health or family — forget those things. I’m talking about even just material life. There’s not that much they can spend on that we really need or would want.
So I’m on the lookout for it — what are ways that people use money or spend money that’s interesting to me? And what I noticed was there were very few luxuries that I actually wanted that other people had. Instead, we flipped it — and there were actually some really small little luxuries of life.
When I was talking to Ben, he’s like, “Dude, there’s this little luxury of life I miss at this Airbnb.” He said the Airbnb had really cheap towels. He’s like, “I just recently splurged on having amazing bath towels. I use two every time I shower. It drives my wife nuts. I bought the $40 or $50 towel instead of the $5 towel. But it’s the little luxuries, man.”
And I was like, “Dude, that’s me with socks.” I hate having mismatched socks, so I threw all my socks away when we got acquired. The only thing I bought was — I threw all my socks away and asked, “What is the highest quality sock you can find?”
Sam: What’s the answer, by the way?
Shaan: At that time it was Bombas. And now I actually have custom socks. I went to a manufacturer and said, “I want a sock like this,” and now I have like 100–200 pairs of custom-manufactured socks from a factory I found off Alibaba. I like wearing crew socks — calf-length, mid-calf. But the Nike compression ones are too tight, and the cheap ones are kind of basic. So I made my own hybrid.
Sam: Do you know that Gen Z makes fun of Millennials for wearing ankle socks?
Shaan: Good. I knew fashion would come back around and be on my side. I’ve been a dork for a long time wearing non-ankle socks. You’ve been winning this one.
Sam: Young people don’t like ankle socks. They like socks that show. And skinny jeans aren’t cool anymore either — you’ve got to wear big jeans.
Shaan: Baggy and high-waisted pants are in. Thank God, because they’re way more comfortable, by the way.
Sam: They call it “cheugy.” When you’re a 35-year-old wearing skinny pants or skinny jeans, that’s being cheugy.
Shaan: How do you use it in a sentence?
Sam: “You’re being cheugy.” Or “He is cheugy.” You could say, “I don’t want to wear skinny jeans, that’s pretty cheugy.” Tight jeans, ankle socks — super cheugy. You don’t want to be cheugy, man.
Mike Posner: The Three-Act Story [00:34:30]
Shaan: All right, let’s talk about Mike Posner. I want to learn about him.
Sam: I know Mike Posner from his song “I Took a Pill in Ibiza” — I think that was his biggest hit. But I also know him because he’s kind of a hippie, mellow guy. I watched a YouTube video about him walking across America. So I look to him as a bit of an energy guru — not that he’d describe himself that way. Is that right?
Shaan: I wouldn’t call him an energy guru, but I know exactly what you mean — he’s an inspiring guy. The backstory is I went to Duke, and in my freshman year I heard there’s a guy in the dorm next door who’s some white guy rapper from Detroit. I was like, “Okay, cliche.” Turns out that was Mike Posner — same year as me, lived one building over.
I remember hearing his songs before they ever went public. “Cooler Than Me,” which was his first kind of hit — I remember hearing that and thinking, “Okay, this is actually kind of catchy.” But at the time it seemed far-fetched, like, yeah, sure, this guy’s really going to make it. He wasn’t the best rapper and he wasn’t the best singer.
While we were at Duke he blew up — second or third year, “Cooler Than Me” took off. We used to hear that he was traveling every weekend, going to do shows at other campuses. He’d fly out Thursday, fly back Sunday night, there on Monday for classes. I remember being like, “What the hell?” He had a meeting with Jay-Z’s record label. I was like, “What is going on?” So that was how I first knew Mike Posner.
Over the next 10–15 years he went on this journey that is a perfect three-act story — which is kind of ironic because when I did the podcast I covered almost none of it. He’s a podcaster’s dream. Act one is the unlikely rise: college musician in his dorm room becomes an international pop star. Act two is the fall: he’s a “one-hit wonder.” His next song goes triple platinum, but it’s still not enough because it’s smaller than the first. The next song goes double platinum, which is even worse. His record label shelves him and won’t even let him release music for years.
Sam: Does he also get into drugs and alcohol?
Shaan: He gets depressed. He’s like, “I lived this lifestyle — I was on the road, taking my shirt off on stage, I was the man. Now I’m not the man anymore.” He hits rock bottom when he goes to a concert with his friend Avicii — the one friend in the music industry who didn’t write him off as a has-been. And he’s now in general admission. He’s in the crowd. He’s watching his friend on stage doing the thing he used to do, the thing he wants to do — performing in front of thousands of fans who love him. And he’s just standing in the crowd like a normal civilian.
He’s hoping someone recognizes him. Someone comes up and says, “Hey, are you Mike Posner?” And then he realized that was his worst nightmare, because the next thing they say is, “What are you doing here? Why are you in the crowd?” Then someone offers him a pill and he takes it. That rock bottom becomes the genesis of the song “I Took a Pill in Ibiza,” whose first line is “to show Avicii I was cool.” That becomes a new hit — two billion streams on Spotify.
And then he feels a bit depressed again, like, “Is this what I want out of life? Am I just chasing this fame high?” That’s when his dad dies. Now it’s act three — the rebirth. He ends up doing a bunch of things. He climbs Everest. He and his friend climbed 71 mountains to prep for it. He has this quote: “You train for climbing a mountain by climbing mountains.” He climbs 70 mountains, then climbs Everest.
Then he decides to walk across America after his dad dies. He walks two-thirds of the way, gets bitten by a rattlesnake, almost dies, has to relearn how to walk after months of therapy. Then he goes back to the spot where he got bit and resumes the walk and finishes it. He’s become this very happy, positive, upbeat guy. He’s sober — doesn’t do drugs, doesn’t drink. He just wants to make art that inspires people.
Sam: Cool. So he’s got this amazing story. Why didn’t you cover it?
Shaan: He’s told that story before. I’m in a season of indulging my actual curiosities. Let me have the conversation I actually want to have. So I talked to him about — how do you actually make the songs you make? What is the creative process? Where does a hit come from? How do you do that? And a lot of his mindset and mentality stuff. I think the podcast is going to be great, but it’s different from what people probably expect, which is just beginning, middle, and end of his story.
Sam: For someone like him who is famous but maybe doesn’t regularly have hits or a tour — how does he survive between them? Like, how does he have super lumpy income?
Shaan: He told me — I asked him that. He said, “Part of it is I got financial freedom.” His wealth manager sat him down and said, “We ran Monte Carlo simulations and look — you’re good. You can always make more, and anything could happen, but by and large you’re good if you don’t let your lifestyle get crazy.” So that gave him the freedom of like, “I don’t even need to have another hit.” Which is kind of the irony — all of his hits have come from a place where he wasn’t trying to make a hit, and every time he tried to make a hit, he didn’t make one.
So I go to his house. And the best thing to do with these podcasts is go to the person’s house to film it.
Sam: Was it nice?
Shaan: We filmed in his studio, which is like a side-house he has — we didn’t go to the main house. But it was cool. It’s at the top of this mountain, so you basically make a trek up this windy road. I was like, “Cool, I’ll pass on driving this windy road every day.” But the house itself was cool, right at the top of the mountain.
I’m standing there at the studio, and his guy says, “Oh, he’s got a meeting right now, he’ll be out in a second.” Then I just hear from the other side, “Wooooo!” Just so happy, outside enjoying his day. He didn’t even realize we were already there. He comes in and he’s just a ball of good vibes. Energy was really off the charts.
People don’t know this, but we’ve talked about it before — we get to see the guest before the lights turn on and after the recording is over. It’s very striking what people are like. Some people have a stark contrast between before and after versus when they’re recorded. Some people are just the same, or even better when they’re off camera. Mike was a great example of someone whose off-camera energy was very, very contagious. Extremely positive person, very nice to everybody in the room. Even afterwards, when he had to leave — his manager was like, “Hey, we’ve got to go, Mike, we’re late” — he stopped and said, “Hey, I gotta go do this real quick, but I don’t want to leave without coming back to say bye.”
Most pop stars don’t do that. They’re just like, “Yeah, thanks everybody, see ya — I’m on to my next important thing. Remember, I’m a very important person.” Instead, he made you feel important.
Sam: Did he remember you from Duke?
Shaan: We didn’t actually ever really cross paths. We didn’t know each other when we were there. I knew of him; he didn’t know anything about me.
Wrapping Up [00:50:00]
Sam: All right, well — that’s it. That was your LA trip report. You had 21 things, we talked about a few of them.
Shaan: All right, that’s the pod.