Sam and Shaan recap their live podcast event in Austin, sharing interesting entrepreneurs they met — including a guy doing $50M+ selling gear to fire departments, the founder of Boom and Bucket (a Craigslist for heavy equipment), and two guys running a digital marketing agency exclusively for franchisees. They riff on Nick Gray’s Two-Hour Cocktail Party book and whether it could become the next Toastmasters. The episode then shifts into a broader philosophical conversation about searching for direction, time-boxing, constraints, and what it means to feel secure. It closes with a tribute to Jerry Springer and his unlikely cultural legacy.
Speakers: Sam Parr (host), Shaan Puri (host)
Austin Live Pod Intro: The Revenue Staircase Game [00:00:00]
Shaan: At the beginning of the show we do this thing where we’re like, raise your hand if you’re an entrepreneur. Most of the hands go up. Okay, keep your hand up if you’ve launched your business. About 15 of the hands go down. Keep your hands up if you have more than a hundred thousand dollars in revenue. Hands go down. A million dollars in revenue. Ten million. Thirty million. We just keep going up to see who is who — who wins the “no small boy stuff” competition in the crowd.
Shaan: Because we’re like, there are people there who already know our story and know our bits. We don’t know them, and so that might be actually more interesting.
Sam: There was a guy who was at like the 30, 40, 50 million level. He’s like, “Yeah, I sell gear to fire departments around the country.” We’re like, hoses? He’s like, “Hoses and uniforms and nozzles — just stuff for the fire department.”
Shaan: Did he say he did 57 million in revenue? Is that what he said?
Sam: I don’t remember the exact number. It was something like that.
Back Home After Austin [00:01:30]
Shaan: All right, we’re live. What’s going on? I’m back home, the live pod is over, the show is over. Let’s talk about your time in Austin.
Sam: The live pod — we should talk about that a little bit. We might be airing that episode. We’ve got to go back and listen to it to make sure there’s nothing we have to bleep out. But what did you think about Austin? It seemed like you had a great time.
Shaan: Had a great time, dude. I know more people in Austin than in San Francisco somehow. I don’t know if that’s about Austin or that’s about me. I think it’s more about me not leaving the house here in San Francisco. But when I left my house and went to Austin I saw tons of old friends. You and a bunch of the crew — had a great time. Started off in a haunted hotel, then moved to a better hotel. Yeah, it was a good time.
Sam: You came in on something like a Tuesday, left on a Sunday? Five days?
Shaan: Tuesday to Sunday, yeah.
Sam: You spoke at two conferences, you were on the Chris Williamson show — that guy’s interesting. But what was cool having you here was I felt like I missed our times in San Francisco. The 2012 to 2018 era where it felt like all of us were doing the same stuff. Then when you came to town we had like three or four dinners of eight friends and it felt like, oh wow, this is happening again. It’s not happening to the extent of what we experienced then, but there are a lot of really special people here and it felt really cool to appreciate that.
Shaan: Yeah, you’re right. I think people should do whatever we did in our 20s, which was move to the city where there are a bunch of other people chasing the same dream as you. You could pick a city based on weather, based on location, based on cost — those are some factors. But if you’re in your 20s and you’re the type of person who listens to this podcast, you’re somewhat entrepreneurial and ambitious, I think the move is to go to a place — doesn’t even have to be a city, could be a house in whatever town you’re in — where you’ll be around other people who are chasing the same dream as you.
Shaan: It is massively underrated. You will not only get smarter faster, but you bond with people and those bonds don’t go away. You’ll always kind of remember when you were all at the very upstart phase of what you were doing.
The Live Pod Crowd [00:04:15]
Sam: We did this live podcast — it was me, Shaan, and Andrew. The content was fine enough, we’ll talk about that later or just air the episode. But what was cool was I met people. We had 550 or 600 people, it sold out. We stayed afterwards — Shaan and I and Andrew — and did a meet and greet with everyone.
Sam: And you always talk to these people and I’m amazed that they would fly in from all over the place. I met a guy from Malaysia. I met people from all over Mexico, America, North America, who came and they were like, “I came here because in my town I’m a weirdo and it feels nice to be around other non-weirdos.”
Sam: And I looked at Twitter afterwards and saw pictures of — we didn’t let people into the venue until right before it started, and in the line, I don’t know if you saw this, there were people interviewing each other for their own content channels. People were like, “Oh I met this person who’s doing this, I met this person who did that.”
Sam: Did you meet this Mexican lady who moved from Mexico City to Ann Arbor? She flew down from Michigan — it was her and her 12-year-old daughter.
Shaan: I did. I love them. She was like, “Hey, love the pod — this is my daughter, she listens as well. We listen together.” And I asked the daughter what she liked about the show. She was quite shy but she said, “I just like that it’s fun. It gets me laughing, and I just learn different things, and it makes me want to go do stuff.” And I was like, you know, that is the actual sales pitch. You’ll laugh, you’ll learn something, and it’ll get you excited to go do stuff.
Shaan: And the mom said, “Thank you for the pod, because it’s the only podcast we can listen to together that we both enjoy, so it’s become a thing we do.” That was probably not that common, but that was one of my golden nugget takeaways from the whole thing.
Sam: She was my favorite person I met. But my point is, what we saw in micro with 500 people was: go to the place where there are other weirdos like you, and cool stuff happens.
Sam: I met a lady who was like, “You talked about me on the pod, and I recently sold that thing for 30 million dollars.” She had been waiting in line for 30 minutes to tell me that.
Interesting Entrepreneurs at the Event [00:07:30]
Sam: So there was a guy who gets to the 30 to 50 million revenue level in the staircase game — he sells gear to fire departments. Hoses, uniforms, nozzles, just stuff for the fire department. He said he had an exclusive right to sell in nine states. Beautiful business — basically a monopoly on selling in these certain states. He won the contract or whatever. Really profitable business.
Shaan: And who even thinks about that? Like, who is the B2B e-commerce for fire departments? It just gets you thinking about how many niche businesses are out there, because you just kept meeting one after another. Do you have any others that stood out?
Boom and Bucket: Craigslist for Heavy Equipment [00:08:45]
Sam: We went to dinner the night before and one business that I really like — I’m eager to see if it’s going to work out — is called Boom and Bucket. What Boom and Bucket does is, if you need to buy a tractor or a Caterpillar, dump trucks — basically anything with a bucket that carries stuff — it’s a marketplace for that.
Shaan: That’s a really good name.
Sam: Boom and Bucket. It’s a really cool website. The founder, his name is Adam Lawrence — he previously was the CEO of Bolt. Bolt was like this high-flying one-click checkout startup, raised something like hundreds of millions of dollars at a multi-billion dollar valuation. He left there after a while, then went and started Boom and Bucket. I think it’s only a year or two old, still figuring out if it’s going to take off. But really cool business that I think will work once they can get the supply and demand side working. You know how marketplaces are.
Shaan: I’m on their site right now. So Boom and Bucket — which also sounds like an amazing name for a bar in Austin, like dollar Jell-O shots and ax throwing in the back.
Sam: That’s literally what people do in their backyards here.
Shaan: The first listing on here is a 2012 Caterpillar 420F, $77,000, ships nationwide. You click it and it’s basically: here’s the thing, previously used in construction for concrete work, here are the specs, here’s what we found was great about it, here’s what needs work — “residual oil buildup on the engine valve cover, no active leak seen.” So they’re adding value by doing inspections, detailed photos, and then they say you can buy through them, they’ll finance it, and they’ll take care of shipping.
Shaan: This seems like a great idea. I don’t know anything about this niche so take that with a grain of salt, but I love the name, I love the idea, and I love that this guy went from the most Silicon Valley VC thing you can do — a network-effects, VC-funded, multi-billion-dollar unicorn that’s either going to become worth 100 billion or go to zero — and he’s like, “I’m going to move to Austin, grow a mustache, and start selling tractors online.”
Sam: Dude, he had a thick beautiful mustache and he was wearing cowboy boots. He looked exactly how you want him to look. He looked like he was in disguise.
Shaan: Like you’re just trying to blend in in Austin.
Sam: This guy’s awesome. His name’s Adam Lawrence. I love Adam. I’ve gotten to know him over the past year.
Franchise Digital Marketing: A Hidden $100M+ Business [00:11:30]
Sam: Another one that I thought was cool — these guys were in the meet-and-greet line. They come up and they’re like, “Hey, love the pod, no questions, just want a picture” — actually, they had one question. They said, “We do franchise marketing.” And I was like, franchise marketing? Say more.
Sam: They’re like, “Basically five percent of McDonald’s stores use us as their digital marketing and social media agency.” And I was like, five percent of McDonald’s franchises? That seems really significant. They’re like, “Yeah, it’s going great.”
Sam: This is actually the second time I heard about it, which is my rule of two: if I hear about the same thing from two completely separate people, it’s time to roll up the sleeves and go down a rabbit hole.
Shaan: You heard someone talk about the same type of business?
Sam: Same style of business. Our buddy Cieva had told me about two businesses. One’s called Scorpion Marketing and the other is called Ferocious Marketing.
Shaan: Okay. The name seems like a little bit of an overcompensation, but they actually sound like badass businesses.
Sam: I need like a Rabies LLC. Fever Marketing. Something like that.
Shaan: Genghis Khan Incorporated. Kill the competition.
Sam: He had told me that one of those two — I don’t remember if it’s Scorpion or Ferocious — does over $100 million as just a Google pay-per-click plus Facebook ads agency for franchises. They go to every Goodyear Tires franchisee in America and they’re like, “You need a good presence online. We help Goodyear Tires franchisees make more money at your location — you pay us, say, $10 grand a month, and we take care of your website, your marketing, we’ll make sure you’re visible on Yelp and on Google when people are searching for tires.” Then they go do the same thing they did in tires and they’ll do it in Jamba Juice, and then they’ll do it in one franchise after another.
Sam: I kind of love this model. The idea of a generic agency, but tailored specifically toward franchisees. Here’s why it’s great: first, all franchisees are going to have the same problem set — you’ve got a cookie-cutter customer. I love that. Two, if something is a franchise, it’s got scale already, so you know the niche is validated. Three, it’s the easiest marketing pitch in the world once you get started, which is: “Yeah, five percent of McDonald’s franchisees use us. We are the largest agency for McDonald’s franchisees. We serve over 150 stores.” The 151st franchisee is way easier to sell to once you hit 150. It’s a snowball.
Sam: Your operations can get streamlined because they all need the same thing. And that type of customer — a franchisee — they’ve basically put their net worth on the line to own these franchises. They’re typically not super tech-savvy or online-savvy, and so I think they’re the perfect kind of customer. You can provide clear ROI from month one.
Sam: And I think you could do this in a lot of niches. I think you could do this in senior living. My father-in-law has a senior living facility, and basically the entire business comes down to one question: how’s our occupancy? If occupancy’s at 55 percent versus 65 versus 75 versus 85 — that’s a swing of like 10 million dollars right there.
Sam: So I’m like, what are we doing to fuel that occupancy? And he’s like, “I don’t really know how to do online marketing.” Most people who own senior living facilities are not the most tech-savvy. He’s like, “We host a coffee and donuts brunch for local hospital nurses because that’s our number one source of deal flow right now. And there are these search engines like Place for Mom — you tell them, ‘I’ll pay you for leads,’ but they just don’t bring that many.”
Sam: Somebody who can rank you at the top for a search like “Senior Living Austin” or “Memory Care Austin” is going to be the difference between 55 percent occupancy and 75 percent occupancy. So if you found a franchise niche like that and did digital marketing for it, it becomes very appealing.
Shaan: Yeah. You just have to run it, which can be challenging. Running those companies is very hard. But getting customers is actually easier.
Sam: What’s the one thing that makes everything easier in running a company? A good way to get new customers. It’s like Advil for all aches and pains — well, at least we’re getting a bunch of customers reliably. Every other complaint from there is a little bump and bruise.
Nick Gray and the Two-Hour Cocktail Party [00:17:00]
Sam: Another interesting person you met for the first time was Nick Gray. Nick Gray — we asked him to MC our event, and then he ended up just attending every other dinner we had and embedded himself hardcore.
Sam: What’s interesting about Nick Gray is you guys should look him up, because in real time you can watch him become an authority on this very strange topic of hosting small gatherings. And he might be able to turn this into something substantial.
Sam: To give you an example of what happened: we had this fancy restaurant booked for one dinner, it got rained out because part of the table was outdoors. So we went to a kind of crappy bar and then moved to another bar next door. Andrew, one of our guests, was like, “Oh man, is it going to be cold?” And Nick was like, “Yeah, it might be cold, hold on” — and he ran to a shopping mall across the street and bought a hundred-dollar long-sleeve T-shirt and came back and goes, “I got you.” How impressive is that? He was the ultimate party host, which is no surprise because that’s what he does.
Shaan: I just met him and I got my first dose of Nick Gray, and I can’t wait for my second dose. Basically it sounds like he ran a company called Museum Hack, which was a kind of adventure company. You’d go to a museum, the tour would be hosted by a local stand-up comedian or magician or somebody with showmanship, and basically he paired showmanship with something that needed showmanship — museum tours. Good company. I think it was making a couple million dollars a year in profit. He sells the business, takes the proceeds, and invests it.
Sam: Did you say he put it all into Tesla?
Shaan: Previously he had made money because he and his family started an aviation parts business — they made the navigation screens that go in private jets. With the earnings from that business he invested it all in Tesla. There are these funny pictures of him during the New York Marathon years ago holding up signs that said “Buy Tesla” — he was trying to Tesla-bomb everywhere.
Sam: Yeah, yeah.
Shaan: And then he killed it on that, started the Museum Hack company with those proceeds, then put it into Cloudflare — which has not done well. But you’ll see him all the time: someone will post, “What’s the best service for X?” and he’ll reply on Twitter, “I hear Cloudflare is really good, you should check out Cloudflare” — like he’s just out there promoting it.
Sam: And with his book he does the same thing. He’s got this book called The Two-Hour Cocktail Party. If you go on Google Maps and look at the reviews of any bar in Austin, he’s been there and reviewed it. When he reviews it he takes a picture of his book in front of the sign or the food — like guerrilla marketing. That’s all he does. Little things.
Sam: You told me about this guy as this super social connector in Austin doing this thing called the Two-Hour Cocktail Party. He’s sold 10,000-plus units of the book. And I couldn’t tell at first — I’m playing the Indiana game: is he an idiot or a genius?
Sam: The case for idiot: he sold his company and he’s all-in on perfecting this little content brand around hosting a two-hour cocktail party. I can’t tell you the last cocktail party I hosted. He spent three years all-in on this. And books in general are not a great business model. So I was like, what is this guy getting at?
Sam: But very quickly I shifted into: no, this guy’s a genius. Here’s why.
Sam: First of all, it’s a real problem. Hosting a dinner party is something that is valuable if you do it well, kind of stressful when you do it, and there’s a difference between bad, good, and great. The details are things like: when you invite people, how do you prep them for it? What is the email you send beforehand that reminds people this is happening, what it’s going to be about, and how they should show up?
Shaan: He’s a big name-tag guy.
Sam: Name tags! You gotta have name tags.
Shaan: Yeah, you gotta have name tags. Okay, what else?
Sam: He’s like, you want the event to flow versus just having it be, well, whatever happens — if we break out into random cliques of people who already know each other, or it becomes a giant group where it’s kind of awkward. He has some structured time and some structured conversations, and then back to unstructured after — because the structure gave everyone something to talk about in the unstructured time.
Sam: He goes into little things like: if you host something at your house, nobody knows where the trash is. So they’re opening all your cupboards, going through all your stuff, then just leaving it on the counter. Put a label on the trash can. Just do that. He’s got all the little reminders and tips for a host.
Sam: So: solves a real problem that’s kind of stressful and kind of valuable if done right. We’ve both been to parties where the magic happens — the conversation gets really interesting, you meet three or four people who become really good friends. This is actually how we met, right? You hosted a dinner party at your office. The right dinner party can lead to some really great things.
Shaan: So why do I think it’s actually genius? I think he’s got a win-win scenario. Whether this becomes a big deal or not, he wins.
Shaan: The first part is: by doing this, he is building the ultimate friend group and network. Andrew Wilkinson called him a “friend billionaire.” He goes, “Nick’s a friend billionaire.” Nick won’t brag about it, but I’d be like, “What’d you do this weekend?” He’d be like, “Oh, I was at a friend’s house.” “Who?” “Matt Mullenweg, the guy who started WordPress. We were just hanging out all weekend.” And I was like, how do you know Matt? He’s like, “Oh I met him at a dinner.” He just has so many stories like that.
Shaan: When you’re a friend billionaire, you know a lot of cool people. So you’re constantly inspired, you’ve got a lot of people who have your back, and you have a real social life. I think it’s like one of these silent epidemics going on right now — most people I know have a really weak and feeble friend group. Maybe I’m just in that world, I don’t know. But a lot of people have this feeling of: I work from home, I live at home, I eat at home, I order food on DoorDash, and I can go seven days without seeing another person with a pulse. Or even if you are seeing people, it’s all transactional — you live in SF or LA and you go to Barry’s Bootcamp and everybody rushes in, does the thing, and rushes out. Where am I supposed to make new friends? That’s not really easy for most people.
Shaan: So what Nick has is actually quite rare. Whether this becomes a thing or not, at minimum he makes a bunch of friends and has a bunch of fun experiences. He was showing me this video on his phone — he’s like, “Check this out, last night after we hung out I was on my way back and my friend texted me: you gotta see this.” It was flooding on some street, water running really fast, there was a lip in the road where you could go on a boogie board and basically feel like you’re surfing. And they just did that for hours. He had these fun videos and I was like, cool — I was just on my phone scrolling. This guy’s not only a friend billionaire, he’s an experience billionaire.
Shaan: So that’s the bottom of the win. But at the top I’m like: dude, I kind of think this should be a local franchise. I think he should basically turn this into the modern-day Toastmasters. If he wanted to, this could be an enormous business that helps a lot of people. He could say: open up a local chapter — like Toastmasters — but dedicated to hosting awesome get-togethers of awesome people. I’ll train you how to host them. You fly out to me, you attend one of these, that’s part of your training, and then go wherever you live and start hosting these things. Pay your membership dues. Let’s create an international wave of people who want to get better at hosting things and having an awesome social life.
Shaan: I think he could create the next Toastmasters. What do you think?
The Toastmasters Business Model [00:25:30]
Sam: So Toastmasters — for those who don’t know, I knew it as a public speaking club. You pay 50 or 100 dollars a year and you go to a local chapter where everyone practices public speaking. They also weave in some leadership component. They’re non-profits. Toastmasters has 63 million dollars in assets, of which about 35 million is cash. Last year they did something like 25 million in membership dues and about 30 million in total revenue.
Shaan: Oh, that’s very nice.
Sam: That’s very nice. It definitely worked.
Shaan: And I think there are a lot more people who want to be able to host a party and build an awesome social life for themselves than there are people who want to get better at public speaking. So I think this actually has a lot more legs.
Shaan: It reminds me of The Game. I haven’t read the book, but Neil Strauss wrote it — “Hey, do you want to get better at meeting women? This book is going to tell you some war stories plus techniques to help you do that.” This reminds me a little bit of The Game — it’s got the benefits of The Game without the sleaze factor.
Sam: I just gave him the thought leader triangle with my hands — for those who are listening, you start with a pyramid of hands pointing upwards, and then on the inflection point of the sentence, you flip it down.
Common Questions in the Meet-and-Greet Line [00:28:00]
Sam: Did you meet anyone else that was interesting, or have any other thoughts about people you met or experiences?
Shaan: I got a couple of high-level thoughts. So we do the meet and greet for almost two hours after the show. Were you tired after?
Sam: I have this thing where relief gives me a lot of energy. I was so relieved that the show was over, that people had a good time, that my trip was done and I was going home to my bed — I was traveling with my two little kids, which has its own challenges. I had no less than 10 people reference the size of the cotton candy that my children had. My wife wanted to see the show, so she brought my kids — who were two and three years old — to the show. That’s like opening a lighter inside a natural gas factory. You know this thing could combust at any second. She had a backpack of bribes, which I think should actually be its own product for traveling moms: a pre-made backpack full of little dollar store toys you can hand out every 15 minutes to keep them occupied.
Sam: And just unbelievable amounts of candy they never get to eat. Bathtub-sized containers of cotton candy. Someone told me, “We saw Shaan’s kids eating a kebab, except it was Sour Patch Kids.” Like a 95-story Dubai tower of lollipops.
Shaan: Yeah, I had a bunch of people tell me about that. But anyway — what were you saying?
Sam: In the meet and greet line, the most common question — and I don’t know what you experienced because you had your own line and I had mine — but I got a lot of people being like, “Love the show, can I take a selfie, and I’ve got one question for you.” And I’m like, oh this is going to be a doozy, they’re using their one shot. And the most common questions had the most obvious answers.
Sam: It would be like, “I’m trying to decide between this or this — what do you think I should do?” “Well, what do you want to do?” “I really want to do this.” “All right, well then you should probably do that one.”
Sam: Or it’d be like, “I’m doing this, this, and this.” And I go, “Oh cool, what are the results?” They tell me. I’m like, “What were the results last year?” “Okay, well — keep going.” Either it’s working, don’t mess it up. Or it’s not working — sounds like you’re asking me for advice, not investment. Same thing: “I’ve got two ideas, one company does this and another does that, and it’s really hard because…” Cool, sounds like you’re running two companies. Do you think the optimal strategy is going to be to do two startups at once or one? “Well, yeah, probably one.” Cool, so which is the better business? Which one do you want to do, which one is working better? “Well, see, this one feeds into this one—” No, it actually eats away at all of your time and mindshare. It doesn’t feed into anything.
Sam: Elon Musk can run two companies at once. He might even be able to run three. But unless you’re built the way he’s built, it’s probably not the optimal strategy. If you’re in this meet-and-greet line, I’m just going to tell you right now: probably don’t be CEO of three startups at once. If you just focused on the one you like more or the one that’s working better, that would probably work better than trying to make both of these fledgling things work simultaneously.
Sam: I felt almost silly that that was the case. But what we’re saying here — everyone was searching. We met a bunch of successful people. Probably one of the more successful people we met was this guy named AJ Patel, 32 or 35 or something like that. He started a dog supplement company — whenever I hear that I’m like, that’s the greatest thing ever — originally sold a portion at a $200 million valuation, then a few years later sold it for $650 million. He seemed pretty zen-like, had his act together, but still there were some things where he was trying to figure out what to do next. Normal questions everyone else had.
Everyone Is Searching [00:33:30]
Shaan: Actually I want to say one last thing about that previous thing — about most common questions having the simplest answers. That’s not a knock on those people. What I meant is: dude, this game is not as complicated as we make it. I make those same mistakes. All it takes is a third party with a fresh set of eyes just saying, “Well, sounds like just pick the one you want to do.” Or: “Instead of doing three things, try focusing on one and it’ll probably work better.” It’s useful to have that be your own inner coach and save yourself a lot of heartache. Because it wasn’t a knock on those individuals — it’s that this is the common problem. We don’t have complex problems, we have simple problems. A simple problem doesn’t need a complex answer, it needs a simple answer.
Sam: All right, so the second thing.
Shaan: Everyone is searching. It didn’t matter who we were hanging out with — net worth zero, net worth 100K, net worth one million, 10 million, 100 million, or the billionaire we had dinner with — everybody was searching. Searching for meaning. Searching for what’s next. Searching for what they should be doing with their time. Searching for a better challenge. Searching for a way to solve their problem.
Shaan: It just felt like everyone was searching, and specifically a lot of people were searching for direction. It really highlighted to me the value of when you know what you want — when you have a clear direction. Be grateful for that. And find people who are good at figuring that out, because if you stay in that searching state for too long, that’s dangerous.
Shaan: It’s like an Inception thing — we can only be in the dream for an hour before we forget it’s a dream. There is an okay amount of time to be in a wandering mode or searching mode. But after six months, after 12 months, after 18 months, that becomes you getting lost in the sauce. I felt like there were quite a lot of people who were lost in the sauce, where their search was sort of almost indefinite. I think that’s dangerous.
Sam: That’s interesting, and that’s actually really scary, because it’s one of those things where if it goes on for too long it gets even worse. You forget how to even start the engine — it’s like this car hasn’t been on for a long time. Does the engine start?
Shaan: And I think you’re really good at this. The way you’re very structured helps you. My read of it is: you time-box things.
Sam: That’s exactly right. I time-box things. And there’s an argument for just wandering around and not trying to control everything. But I think having these creative constraints, these time-box constraints, keeps you honest. Am I really learning from my wandering? Or have I forgotten my head from my feet? Do I even remember what the hell I’m supposed to be doing right now?
Sam: You had a period post-Hustle and pre-Hampton that was your searching period. But you knew you were going to search, you knew you were going to wander and explore — which meant don’t jump into something really fast, but also don’t let that last forever. Is that right?
Shaan: Yeah, well — I’m obsessed with time. Even when I was 20 years old I had this document — I think if you Google my name and “CEO doc” you’ll find this spreadsheet — where I mapped out thousands of biographies I’d read, typing in when people started their apprenticeship, when they got successful, and the time it took. I was obsessed with time because I think the constraint is incredibly necessary. I read this book by Robert Greene where he talked about urgency, and that was the first time I learned about the importance of urgency.
Time-Boxing, Worry Time, and Constraints [00:38:45]
Shaan: What I do is I have this thing called “worry time.” It’s very similar to searching time. Worry time is: here’s the period where I can worry about these specific things. So I’ll make a list of everything in my life that I’m not sure about — could be this podcast, could be a relationship, anything. Then I’ll say: on Sunday from 3 to 8 PM, I’m going to worry about those things. And I’m not going to let that worry seep into every moment of every day as this underlying anxiety that just plagues you.
Sam: Have you ever used Headspace, the meditation app? There’s this cool thing — Andy, the guy who narrated it, would say: “All right, today we’re going to do the meditation. A cloud is above you. Put all of your thoughts, feelings, and worries in that cloud. Now let’s walk a few feet away. We’re away from the cloud. We can acknowledge that our worries are up there, but we’re no longer under it. We can go back under it when we’re ready.” That’s kind of where I came up with worry time.
Shaan: So I have worry time and I do the same thing with searching time. I’m going to search for this, and in three months I’ll ask: did I find it or not? No? Fine, we’ll give it another three months. Once I find it, searching is done. And I actually turned off the Twitter DMs on my handle because I would get all these interesting opportunities, but I said: nope, we are done with opportunities. I have the opportunity, we’re going to pursue that. At a later date we’ll open back up. Right now, nothing new.
Shaan: My wife and I were joking — but it’s not really joking — my rule right now is: No New Friends. I don’t need new friends. I have the friends I want. I’m not going to go out and hang out with new people. No New Friends. Because the searching time is done for now, and we’ll open it up at a later date.
Sam: Dude, that’s great. I love the way you said that. I do a similar thing, but without — I hate the word “time.” I’m the opposite of you. I want to get off the concept of time altogether. But in reality the result is very, very similar.
Sam: What I do is I focus on the word “constraint.” How can I use a constraint to my advantage? Like, naturally I’m always constrained. Let’s say I’m traveling and I don’t have the time or equipment to get to the gym for my normal workout. How do I get excited about the constraint? I’ve got this wall, the floor, my suitcase. Interesting. I can air squat the suitcase. I could do a push-up challenge where I’m going to do 100 push-ups in the next five minutes and see how far under that time I can get. You’ve used a constraint to your advantage to have a better experience.
Sam: So I always have this thing: I’m not going hour to hour — I think time creates a lot of stress in people’s lives. I want to use constraints without the stress of time. What I say is: I’m trying to have an experience right now, what kind of experience do I want? I want a sweaty workout experience. Okay, how can I now use a constraint to ratchet that up and make it even better?
Sam: I’ll do the same thing where I’ll constrain myself: I’m going to turn off DMs, or do a No New Friends season. And I’ll use words like “season” to time-box things without the urgency or stress. The thing you did — mapping out how successful guys were by age 30 — dude, that would have made me feel miserable. So I had to tweak it a little bit where I didn’t want to always feel perpetually behind in life. My way of doing that was: focus on what kind of experience I want to have, get good at choosing that, then ask how a constraint can level that up rather than making me feel limited.
The Art of Fulfillment vs. the Science of Success [00:43:30]
Shaan: I think the time thing is important because you do compare yourself to others. Comparing yourself — everyone says it’s bad, but I actually think in some ways it’s really great. You see what’s possible. Just like if you’re an athlete, you see what you want to be like. But whenever we do these events and I meet all these amazing people — an AJ, an Andrew Wilkinson — and I hang out with them and think “I’m behind,” that’s dangerous. That’s the thing I referenced: the science of success versus the art of fulfillment.
Shaan: Comparing yourself will help you in the science of success. It’ll motivate you, put a chip on your shoulder, light a fire under your ass. But it’s not going to help on the art of fulfillment side.
Shaan: So what some people try to do is solve the success thing first and then do the happy thing after. What ends up happening — back to my “everyone is searching” point — is people solve the success thing and try to throw money at the happy thing. It works to an extent but not all the way. They feel disillusioned and fall back on: “Well, let me just do more success stuff. At least when I was only focused on success I felt like I knew what I was doing.” Or it’s: “I thought this number would give me the answer, but turns out I was just one question away — and now the number is five times higher.”
Sam: Yeah, it’s never 50 — it’s always 150. People always think: three times more and then I’ll chill out and move to the next phase.
Shaan: I think while that’s not a terrible path, there’s probably a better version of it: can I do happy and successful at the same time? Is that possible?
Shaan: We had dinner with Andrew, and as of Friday his company was worth 850 million Canadian. We were talking about personal motivating factors and he said, “I was motivated because I wanted to feel financially secure — I always felt insecure as a kid.” And I asked, “Do you feel secure now?” And he said, “You know what? Not really.” And I’m like — wow. You’re still not going to feel secure at that number?
Shaan: I couldn’t decide if I felt negative or positive about that feeling. But I’ve realized that might be the learning: you don’t feel secure — a lot of people don’t feel secure regardless of what they have. It’s the same feeling of: it’s not enough, it can get taken away.
Sam: I view it a little differently. The security doesn’t come from the money. That feeling you want isn’t going to change when the money changes. I feel secure now and I have a tiny fraction of what he’s got. Because I just view it differently. I have different insecurities than he does. On the financial one, I’m like: as long as I’ve still got my wits and my two hands, I’m always going to be fine. If I’ve got my brain and my hands, I’ll always be fine. The podcast could tank, I could say the wrong joke and get canceled — still got my hands and my brain. I’ll be all right.
Sam: Think of it like fitness. If I put you in any fitness test, I think you’d feel pretty secure. If you invited me over for a hard workout, I’d be stressing out — wait, was creatine working? I don’t have the fitness security. Whereas if I invited you over for a hard workout you’d be like, “We’ll see.” Maybe if David Goggins invited you for a workout you’d feel a little lacking, but for most people in most situations you’d feel pretty secure.
Sam: Everybody’s chasing a feeling they think comes from a thing. The feeling doesn’t come from the thing — the feeling comes from you. It comes from practicing having that feeling. And until people clock that, they’re just not going to have the kind of happiness and fulfillment they want.
Shaan: Speaking of which, we have a very sturdy audience. I was going around putting my hand on people’s backs to take pictures — there were a bunch of deadlifters there. What was going on?
Sam: There were a bunch of sturdy people — maybe it’s a Texas thing. A bunch of big boys. And women too — so many strong people. The meet-and-greets are weird, I don’t know what to say to people, so it’s usually like, “Oh I like your shirt” or “You look huge, you’re yoked.” But I said that so many times.
Shaan: We have an interesting demographic. There’s people that look like you, people that look like me, and then people that look like neither of us. It’s kind of amazing how well-distributed it is — a bunch of Indian guys, a bunch of really strong white guys, and then a blend of everyone else.
Sam: We had so many Indians, so many with really thick accents. Do you think we’re popular in India because of the topic or because of you?
Shaan: I mean — like anything, where’s Chamath from?
Sam: Sri Lanka.
Shaan: So they probably love him too. But yeah, Naval, Chamath — those people are like cult figures in those communities. It’s like Kobe Bryant in China. They piped Laker games into China for a period, and he was just the star of stars in everyone’s mind. People look up to people who are like them but more successful — like, “I could be them.” And then there are people so unlike you that you’re just in awe of them.
Shaan: It’s like the Björk effect. Björk is from Iceland, which only has like five million people, and every once in a while she’d be number one on the charts because everyone in Iceland was cheering for her — she was doing something interesting in America. Or Bruno Mars: if you go to YouTube, his videos have three, four, five billion views because everyone in the Philippines is like, “That’s our guy.” So I guess that’s why we have a really nice Indian contingency — because you’re their guy. Whereas with me it’s just a bunch of guys from Ohio.
Jerry Springer: Career, Legacy, and Pioneer [00:51:00]
Sam: Can I do a little bit here on Jerry Springer? He died two days ago. RIP. His story is kind of crazy. Do you know much about Jerry’s backstory?
Shaan: Wasn’t he the mayor of somewhere in Ohio?
Sam: Basically — so his career goes: at 25 he’s an advisor to Robert Kennedy during his presidential campaign. Then he goes into local city politics and ends up becoming the mayor of Cincinnati for a brief period of time. Gets fired because he solicited a prostitute and got busted for it. So now he’s out of the political game, in his 30s, like, what do I do next?
Sam: He gets cast on local TV to do a political show. “You could be our political talk show type of guy.” He does that for a little bit, then gets his own show. This is like 1991 or something. He does his own political talk show. Three years go by — kind of unspectacular. And then the moment happens: a new producer comes in and says, “Hey, look — this political show isn’t going anywhere. Let’s switch it up.” And the Jerry Springer Show is born.
Sam: The producer says: we’re going to shift it toward controversy, dirty laundry, captivating TV by putting scandal on air.
Shaan: Was it fake though?
Sam: There are different opinions on this. I read a bunch of Reddit posts from people who were producers on the show or went on the show. Here’s where I think it shook out: they would cast for scandal. People would say, “Yeah, that happened to me.” The producers would intentionally not fact-check anything. So for some people it was truly real — but for a lot of them, they were like, if I do this, I get to be on TV, I get a flight to New York, me and my person get to basically go on a vacation to New York and be on TV. So they would embellish. It’d be like, “Yeah, I cheated” — but actually they weren’t best friends, they kind of knew each other, he already knew about it, he’s not finding out on air. But whatever, we’ll recreate it.
Shaan: Was it daily or weekly?
Sam: Daily show. And at its peak, higher rated than Oprah. So he becomes the number one daily show. Jerry knows it’s stupid but he’s like, “This is what people want, and I’m going to give them what they want.” It goes 18 years on TV.
Sam: I had a few takeaways from this. First: he gave people what they wanted, not what he thought they should want. He started with what he thought they should want — here’s the latest on local political issues — and he pivoted. And he pivoted the right way. I think as entrepreneurs, there’s a great Gary Halbert quote: “Never has more money been lost than trying to market to somebody what they should do versus what they want to do.” As a marketer you have to internalize that.
Sam: Now, there are some people who hate that phrase. They think: shouldn’t we strive to make the world a better place? Not these sugar-filled cereals and dopamine social networks. Some people are fighting against it. But as an entrepreneur, I’m in the camp of: you are here to serve customers. You’re here to give them what they want. If you want to win, you give them what they want. If you want to win really big, you give them what they want in a way that no one else is giving it to them — or maybe even in a way they didn’t even realize they wanted.
Sam: Two: he pioneered a new format. His whole format of putting dirty laundry on air — the fights, the bouncers, the DNA test reveals — this guy’s a damn innovator. Three: he became number one, bigger than Oprah in his prime. And lastly: he got his friends to win too. His security guy Steve became a character on the show, his best friend — and Steve gets his own spinoff show later. So I love that he brought friends along for the ride. When he eats, they all eat.
Sam: And the other funny thing — people liked working for Jerry. It was like the opposite of Ellen. Ellen was seen as America’s sweetheart but apparently behind the scenes was a menace. And apparently Jerry was the opposite — seen as a menace to society but actually kind of a sweetheart, from what people said.
Sam: The last thing I thought was interesting: because the show was really popular in the early ’90s, it was actually the first show to expose a lot of people to people being gay or trans or anything in the LGBTQ spectrum. For a lot of people in America, they had never met or heard of anybody in those categories. And he was kind of the Band-Aid rip-off moment for a lot of America on these things, which I think is also kind of amazing.
Normalizing the “Other” — A Mini-Jerry Moment [00:57:00]
Shaan: The real world was kind of like that too. I went to an all-boys high school and I remember being like 14 or 15 — for some reason our school had a culture where young men felt fine coming out. And I remember meeting these kids for the first time. Someone who admitted to being gay. At first I was like — you know, back then you might make fun of people. And then you realize: oh, that’s horrible. Obviously we shouldn’t do that. They’re my buddies.
Shaan: And it goes back to: because I love you, I’m going to make fun of you — just like I make fun of all my other friends. Because I love you, I’m not going to treat you differently. We’re all boys and we’re just going to tease each other. Someone has braces, someone likes men, whatever. We’re going to make fun of ourselves — that’s how young boys show that we accept each other. That’s how we show love.
Shaan: It was a mini-Jerry. Jerry was first — we’re not going to make fun of this person because of this particular thing, we’re actually going to do it because it shows we’re going to normalize it.
Sam: So who knew Jerry was so progressive? Robbie, Rosa Parks, Martin Luther King, Jerry Springer — just one of many in a lineage of pioneers breaking down social barriers.
Shaan: Yeah. He always seemed really likable. Did you watch him? Like, did your grandma babysit you with Jerry Springer on?
Sam: That’s exactly what I remember. Like at 4 o’clock when you get home from school, watch Jerry and Oprah.
Shaan: Or when you stay home sick from school — Price Is Right, then Maury.
Sam: I loved Maury. Maury was the best too. He’s going to die soon, I just looked him up — he’s 85 I think. The Legends. It’s a passing generation.
Cheaters and the Legacy of Scandal TV [01:00:00]
Shaan: Who’s doing this now? Is there like a thing now — does this happen on TikTok, Twitch, YouTube?
Sam: That’s a good question. You know another great one like this? My sister still listens to this every day when she drives her kids to school: Cheaters on radio. The show where they bust cheaters — that’s still a thing. It’s a big thing in the FM morning radio space, which is a very small thing in the world now.
Shaan: It is actually good though. Was it Joey Greco?
Sam: Joey Greco was the more famous host of the TV version. At one point he got stabbed — you remember that episode where he gets stabbed?
Shaan: Dude.
Sam: And the thing about that era of the ’90s and 2000s: the reason it was cool was we didn’t know if it was fake. There’s no one tweeting it out. You’d think it might be fake but nobody has a platform to actually expose it. Like I wasn’t sure wrestling was fake until like five years ago. I held out.
Shaan: Tooth fairy and Vince McMahon.
Sam: The radio version of Cheaters — they call the wife, or the wife calls in: “I think my husband might be cheating.” Then they call the husband, pretending to be another woman. Or actually what I think happens is: “He might be cheating with my friend Rebecca,” and they fake-call as Rebecca to try to catch him in the act. Then they hit the button and three-way merge the wife in, and she just goes off on him on air. Incredible content.
Sam: If you’re a content creator out there and you’re not studying Cheaters, you’re not even trying.
Shaan: There’s a subreddit called r/PublicFreakout. Ever go to r/PublicFreakout?
Sam: That’s my favorite subreddit. That’s my version of Jerry Springer.
Shaan: r/PublicFreakout and r/Popping — where they just pop zits and stuff.
Sam: I love that one. Big fan.
Shaan: And r/PublicFreakout. I was on the front page of r/Popping one time. I had a picture get 60,000 views.
Sam: Can I endorse you for that on LinkedIn?
Shaan: Dude — I had to get a cyst removed from my head, and right before I went under surgery I said, “Hey, Dr. Brian, can you do me a favor? Here’s my cell phone number — can you take some pics while we’re in surgery and send them to me? I want to post them on this subreddit.” And he did. And I got 60,000 views. I have a folder right here in my browser called “Brain” — before, during, and after photos. I was number one on r/Popping. No big deal.
Sam: I think it’s literally no big deal. Actually, that’s the cool part about it.
Shaan: All right, that’s the episode. We did a recap and we talked about Jerry Springer.