Greg Isenberg joins Sam and Shaan to rapid-fire six business ideas, ranging from an athletic greens for dogs to a Stripe Atlas for trademarks. Along the way the conversation explores the Dollar Shave Club-ification of boring service businesses, luxury newsletters for the ultra-wealthy, and why Veblen goods like Birkin bags explain NFTs, status apps, and the psychology of exclusivity.

Speakers: Sam Parr (host), Shaan Puri (host), Greg Isenberg (guest, Late Checkout)

Intro and Greg’s Stolen Producer [00:00:00]

Shaan: We’re live. Greg is here — friend of the house, one of the originals. You said something on an earlier pod that has always stuck with me. You were talking about names, you had your iPhone out and you were on the Notes app, and you go, “I just got banger names for businesses that don’t have a business yet.” And you were just spitting off names. One of the formats was anything with the word Bueno at the end.

Shaan: I can’t tell you how many times I’ve used this when somebody’s asking me about a name and they’re like, “Yeah, we do medical imaging scans.” And I’m like, “Scan Bueno.” And they’re like, “What?” They never pick it, but goddamn if it doesn’t break the ice. Greg, welcome. Do you still have that note with all those names?

Greg: I’ve got all the names. I’ve also got I don’t know, 150 startup ideas in a notes file. But before I started, I got to get something off my chest. I gotta be real with you.

Shaan: All right. What do we got?

Greg: Producer Ari — you stole my producer.

Shaan: Did we? We don’t know about this. Fill me in.

Greg: So all of a sudden you guys send me a text and you go, “What do you think about Ari as a producer?” I see you work with her and I go, “She’s amazing. She’s the best.” And then all of a sudden I’m getting a text from Ari being like, “Dude, thank you so much. I just got the craziest job at My First Million.” So if I ever call you for a reference check, just know it’s Mr. Steal Your Girl coming at you right there.

Shaan: I thought she worked on it in the past. I thought there was an end date.

Sam: That’s what I thought too.

Greg: It happened.

Shaan: Is it okay?

Greg: It’s not okay.

Shaan: Sorry and thank you. Okay, moving on. Greg, people should know what you do. You have Late Checkout, which is badass. You have one of the best websites of any company. You make really amazing landing pages. Late Checkout is a combination studio, agency — how do you describe it?

Greg: Holding company. Building businesses that have audiences and communities as part of them.

Shaan: And you are kind of becoming this like “Greg the community guy.” I feel like that was a phase of your life. Is that still the phase we’re in? Did it stick? Did the Greg the community guy thing happen, or what?

Greg: I think so, man. I feel like if other people are calling you that, it’s a thing. If you start calling yourself “the community guy” — yeah, it’s definitely working.

Sam: I feel like that’s a mistake I’ve made many times, trying to call myself the guy.

Shaan: Actually, today I was thinking about Gary Vee, thinking about one of my favorite YouTubers, Cody Co, and I was like, why am I not Shaan P? What is “Puri” doing for me? I gotta drop the rest of the last name. I just need to be Shaan P. And I really wrote a note to myself: go all in on Shaan P.

Greg: That’s stupid.

Sam: Workshop it yourself. You’ve got a weird enough first name — S-H-A-A-N. I think you’re good.

Greg: The only reason Sam is saying that is he wants to be Sam P.

Sam: No, man. I’ve got a two-syllable first and last name. I’m good. I don’t need a nickname when it’s that short.

Shaan: Sean Bueno.

Venture Path vs. Cash Flow: Greg’s Philosophy [00:04:30]

Sam: Greg, Late Checkout Studio — I hate your website. You’re doing this designer website thing. I can’t click anything. I’ve got to scroll around a map to find what you do. What’s going on, man?

Greg: There’s two ways to create a website. One is to be conversion-centric — convert as many people as possible. The other way is you’re building a brand, and this is unlike any other website on the internet. You’d be surprised how many million-dollar deals we’ve been able to close because people like our website.

Shaan: You’ve done something that a lot of people were trying to do but you’ve done it well. Let’s talk about this personal holdco thing. You went the venture path when I met you. You were raising money from all the big-name VCs. You were building a social network. We were both playing that game — and the analogy I give is somebody handed us a bottle and we started running around trying to catch lightning. That was our stated game plan: “I shall create the next hit social network now, on demand.” Which is not how any of them actually got built.

Shaan: So you played the VC game and you’ve backed off of it. Give us your two-second philosophy on how your mindset changed going from the Silicon Valley venture path to what you do now.

Greg: There was a group of us, now in our 30s, who watched The Social Network and all thought we could become Mark Zuckerberg. I mean, I would have been happy with a Winklevoss too, but I wanted to be Zuck. We saw that movie, it jazzed us up, and there was a whole generation of us who moved to Silicon Valley to raise a bunch of money and build social apps. We tried. And the truth is, I remember meeting one of the world’s best investors and he once told me: a third of our deals fail, a third we get our money back, and a third we make 1x to Google times. So what he’s basically saying is that the best founders in the world — because he’s only backing the best founders — two-thirds of them basically don’t see any money from acquisitions. It’s just so difficult to win in that game.

Greg: So that’s why I’ve been focusing more on profitable, cash-flowing businesses.

Sam: Are you making more money now doing the cash flow thing versus when you sold your company?

Greg: Yes. Absolutely.

Sam: Do you like your life better?

Greg: Yeah.

Sam: Do you have a goal — like a cash flow goal, like “I want to get to $10 million in cash flow”? Is that the game you’re currently playing?

Greg: No. The game I’m playing is — I’m playing for style points, baby.

Sam: What does that even mean? Is there anything else to say?

Shaan: No, that explains everything. Next question.

Shaan: What Sam was talking about — when Sam was working at HubSpot, he was like, “I’m an artist, baby.” I think that’s what Greg’s talking about when he talks about style points. The other part of style points is the lifestyle. In Silicon Valley, “lifestyle business” is like a backhanded compliment. It’s a way for people to pat you on the head and be like, “That’s cute. Good for you, that’s swell.” But to me, I’m like, that’s crazy. The point of these businesses is to give myself and my team awesome lifestyles. What else are you trying to do if not that?

Shaan: I feel like one of the arbitrages right now — especially if you’re from the tech industry — is that the whole tech industry is so brainwashed about creating multibillion-dollar companies that a lot of people who would actually be super happy with a lifestyle business that gave them $25 million a year in cash flow won’t ever go that path because it’s seen as this lesser thing to do.

Sam: We all have friends who do that. I tease Andrew Wilkinson for doing that. But you know what’s funny? You guys saw Chamath from All-In — I would assume he’s a billionaire. Very, very wealthy. The other day he announced he was starting a paid newsletter at $100 a year. Two things I’ve found to be true: the people who say “I don’t want to be public” — they get on Twitter, they taste that dopamine, and they go “oh, this is nice, I’m gonna do this again.” The second thing: even people running venture-backed companies where there’s a likely outcome they’re wildly wealthy — even making $50,000 or $100,000 a month can be addicting.

Sam: He was like, “Yeah, the revenue from this makes the whole thing sustainable. We can use it to hire researchers.” It’s like, hey, why don’t you just take the 0.1% interest on your savings account with JP Morgan and use that to pay for seven researchers? It’s fine. It’s crazy that people say, “What’s the point of money if you don’t use it?” Like, what’s the point of being a billionaire if you’re gonna do a paid newsletter?

Sam: The point is it’s addicting. I was texting Andrew Wilkinson making fun of him too because he was doing a paid Twitter subscriber thing. I was like, “Dog, you have a foundation. You’re signing the Giving Pledge. What do you care about this $10K a month subscriber revenue that you now have to tap dance for?” But it hits for him.

Shaan: The only explanation I had for Andrew doing the premium X thing was: he’s using Twitter paid features so that Elon is like, “See, this guy’s doing it,” and starts retweeting him, and Andrew ends up becoming friends with Elon Musk. I said that’s the only reasonable explanation. And he denied it.

Idea #1: Good Water — Athletic Greens for Dogs [00:14:00]

Shaan: Greg, did you have any other niche businesses you wanted to get off your chest? Let’s rapid fire.

Greg: All right. This one’s a happy idea. It’s a crazy one, but a happy one. Listen to me now: athletic greens for dogs.

Sam: Okay. Keep going.

Greg: AG1 came out of nowhere, started sponsoring all these podcasts and YouTubers. What do you think their revenue is, Sam?

Sam: 600 million? 500 million?

Greg: I think they kill it. I’ll do the homie move and say 100 million.

Sam: More than 100 million. They’re really crushing it.

Greg: Using that model — dogs are similar to humans in the sense that they drink water. They drink tap water. And the question is: what if dogs drank something that was better for them than plain old water? Here’s the playbook: you find the Andrew Huberman for dogs, you sponsor every top dog creator and animal-lover podcast, you give packets to restaurants and put bowls out that say this brand. Then you profit. The name we call it: Good Water. And our slogan: “Good dogs deserve good water.” We have to figure out what we can put in the water so that it actually is better than water itself. But this is a good example of how you create a category of one — how you build something where no one else is playing.

Shaan: “Formerly respected individual Greg Isenberg disgraces himself with Good Water.” “Shaan P says it’s really better than water, I swear.”

Sam: Is this Gatorade for dogs? The next great thing?

Shaan: This sounds like something Mischief would do.

Sam: I gotta tell you — when Craig Clemens came on the pod, many years ago, he was like, “Guys, VR for dogs.” This is the guy who’s made like 10 hit products. On our pod he comes on and says VR for dogs. And both me and you — we didn’t know him well enough to roast him like we just did Greg, but we were like, “Tell us more.” We were not in on it. But then I swear, every time I leave the house and my dog is just staring at a wall, I’m like: I’d strap on a pair of Oculus dog goggles if it actually kept my dog entertained. I think he was right.

Idea #2: The Daily Fable — Ryan Holiday for Aesop [00:18:30]

Shaan: Greg, I want to talk to you about some of these ideas. The first one you talk about is Ryan Holiday, who’s been on the pod and is my buddy. You seem like you’re in a spicy mood.

Greg: I’m always in a spicy mood. For the record.

Shaan: Let’s talk about it.

Greg: Ryan Holiday — incredible guy. He’s built such a huge brand around stoicism. Stoicism was basically dead unless you were studying philosophy. These people like Seneca, Aristotle — you’d see quotes here and there, but it was basically dead. And what he did was introduce stoicism to millions of Gen Z and Millennials.

Greg: I think there’s an opportunity to do exactly what Ryan Holiday did, but in the fable space. Do you remember Aesop’s Fables?

Sam: What is that?

Greg: Aesop is one of the most well-known storytellers of all time. He wrote things like the tortoise and the hare, the wolf in sheep’s clothing. These little stories that use animals to tell you the moral of the story. It’s got a lot of great stuff in there, just like Seneca had a lot of great stuff.

Greg: So I think if you got the handle “The Daily Fabler” and started telling these incredible stories and quotes from it, you could build an audience really quickly. And similar to how Ryan Holiday monetized — via courses, via books, but my favorite part is he literally sells a coin. He calls it a medallion. It’s called Memento Mori.

Sam: Hey, I have one.

Shaan: Why did you get one?

Sam: Because he gave it to me and I thought it was awesome. I carried it around for years.

Shaan: What does Memento Mori mean?

Greg: Basically, “Seize the Day.” You’re going to die. If you know you’re going to die and you’re facing mortality—

Sam: It’s Greek for YOLO.

Greg: Memento Mori is Greek for YOLO. And people pay $30 for this coin. I’m sure he’s making millions of dollars selling coins to his audience via Twitter, TikTok, Instagram, and YouTube. It’s the same model but for fables.

Shaan: He told us this on the pod and it blew my mind. He was like, “I sell this coin, cost me — let’s call it a dollar.” He partnered with a mint in the US. They mint the coin, he sends it. He said, “I’ve sold shirts before, I worked at American Apparel as head of marketing. Apparel sucks. Merch sucks. T-shirts suck because there are so many sizes and colors. There’s one SKU. It’s one coin. No returns. I sell it in a two-pack. It ships in an envelope because it’s the lightest weight thing — easy shipping, easy manufacturing, easy to sell.” It was the low-headache way to have a merch store for stoicism. And I’m pretty sure he’s made over $20 million just selling this coin.

Sam: I think on the pod he said he sold tens of thousands of coins.

Greg: Yeah. And then if you do the math — $20 to $25 a coin.

Greg: You said something here: it’s harder to be Seneca than it is to be Sahil Bloom. It’s harder to be Aristotle than to be Alex Hormozi.

Sam: So there’s a bunch of tailwinds with this business. Creating content is way more difficult than curating and distilling content. I want people to know that because there are a ton of businesses where you don’t need to come up with any original ideas — you can just curate amazing ideas that other people have.

Shaan: You’re talking to two guys who did that. The Hustle did that, Milk Road did that.

Greg: Exactly. It’s way easier to get your own podcast producer than to steal your podcast producer, you know what I’m saying? My newsletter “Five Tweet Tuesday” — it’s the highest-rated newsletter I’ve ever made. High open rate, most feedback. And it’s also the easiest because I’m just curating five of the most interesting tweets versus trying to create my own original blog post every Tuesday. It is easier to be Sahil Bloom than Seneca, and it is easier to be Alex Hormozi than Aristotle, because they can just take other people’s concepts and curate them.

Greg: The Daily Fable idea has that tailwind. It’s also got this other tailwind: Gen Z basically doesn’t believe in God. Almost 50% of Gen Z is either unaffiliated with any religion or does not believe in God. But it’s just human nature to seek out some greater meaning and purpose in life. That’s why they’re filling their time with Daily Stoic — and could fill their time with something like the Daily Fable. This is what I call the unbundling of religion.

Idea #3: Pinks — Dollar Shave Club for Boring Service Businesses [00:26:00]

Greg: What is this Pinks thing?

Sam: So someone I work with — partner of mine, Jordan — he’s rolling around Austin and he sees this pink truck outside a house. And outside this pink truck are these men with mustaches and mullets and pink shirts tucked in. He’s thinking, “Is this a porno shoot? What is going on?” And then he sees the logo: Pinks. Pinks window cleaning. He finds out it’s a new window cleaning service based in Austin, and it’s a franchise business. If you go to their website, pinkswindows.com, they’ve got this boring business — window washing — and they’ve jazzed it up. They even have a merch store where they’ve apparently sold thousands and thousands of hats.

Sam: I was at dinner the other night and Baro is wearing this hat, and I even said, “What’s this? You’re doing something cool, what is this?” Because he’s one of those guys who knows the indie bands, knows the cool restaurant, knows cool. I’m like, why is he wearing a window washing hat? This makes no sense. And he’s like, “It’s this brand called Pinks. They’re really cool.”

Greg: Style points, baby.

Sam: And that was the end of that story. I went home and I ordered a Pinks hat.

Greg: This is part of a bigger trend. I think this is the Dollar Shave Club-ification of boring businesses. A lot of younger people are going to be buying some of these businesses — Boomers are retiring, you know the story — but what they’re going to do is make it feel like an indie band. The Dollar Shave Club video was funny. It took something boring — razors, Gillette — and made it super cool and fun. That’s what Pinks is doing.

Shaan: That’s actually super smart. Dollar Shave Club kicked off a huge wave of DTC brands — Casper, Away luggage, one after another. Hundreds of them. Basically: take boring category, do best-in-class branding, put a ton of creative effort into it, sell that commodity product online. And what you’re saying is people are now going to do that for sweaty startup businesses. Instead of the lowercase block-letter font with Millennial pink, maybe it’s this vintage retro indie band look that becomes the go-to thing for window washing, trash haul removal, HVAC, all that stuff.

Greg: I’m going to call my shot here and say that Pinks is the beginning of a whole new generation. Over the next 5 to 10 years you’re going to see Pinks for lawn care, pest control, car wash, catering, pet grooming, snow removal.

Sam: The brand behind Pinks is called Resi Brands. They own three or four things — one called Garage Up, which is about making your garage look clean and cool, then Pinks, then a painting brand. The guy who owns it is named Stephen Montgomery. He’s young, like 30, sleeve tattoos. He graduated college like five or six years ago.

Greg: Their painting brand — One Painter — is apparently the fastest growing painting company in the United States. This is a model that’s starting to work. If I’m a PE fund, this is what I’m doing: acquiring boring businesses and hiring a creative agency like Late Checkout to build brands, not boring businesses.

Sam: I used to be close with Brian, the guy who started 1-800-GOT-JUNK. He was telling me all about franchises. He started it with just one truck and grew it. I think now he owns 100% of it. It does $200 or $300 million in revenue. But dealing with franchise owners — he said it’s very, very hard. It’s like the agency business where it looks simple from the outside but doing it every single day is a huge challenge. Almost like working in the restaurant industry. Your server won’t show up because they’re hungover, you get fights.

Greg: I want to be clear: Pinks started as one location in Austin and now you can franchise your own Pinks. They charge a 2% marketing fee, a 7% royalty fee, and a franchise fee of $49,000 to $100,000. And they actually share revenue numbers. For one of their Austin locations — seven employees, $714,000 in revenue, 36% profit margin. It’s a pretty good business.

Sam: Disclaimer: we don’t know if this is a great business. It’s not advice. Franchise headquarters tend to share numbers from their best-performing locations, not the average.

Internet Franchises and EOS [00:37:00]

Greg: Going down the Pinks rabbit hole, I found that franchises are actually regulated by a franchise board — there are portals, you have to apply, and there’s specific information they can and can’t disclose. And then I started thinking: what is the franchise model, and what does it look like for the internet?

Greg: A franchise is basically a business model, a brand, and support in a box for an entrepreneur. How could we bring that to the internet?

Shaan: I had the same thought when you were talking about your agency earlier. Scaling agencies is hard. I wonder — if I have a big audience and a strong ability to create a brand and get customers, the painful part is the operations. What most people do is partner with somebody to run the operations. But what if I franchised it? I could spin up operators — you could become one of my operators, I’m going to hand you customers automatically. You don’t have to know how to do internet marketing, you just have to fulfill the demand I generate. Maybe there’s a way to do it without a 100-person agency headquarters with managers managing managers and all those layers.

Greg: Maybe what we’re saying is the next generation of creator-led agencies actually looks more like franchises than what they are now. Normally you franchise because you can’t geographically expand. With the internet you don’t have the geography problem — that’s why most internet companies never franchise. However, for things that are service-based, you run into servicing bottlenecks.

Shaan: Where I disagree on the geography thing is I think it’s not that we don’t have a geography problem on the internet — it’s just that geography is defined differently. On the internet, your audience is your geography. If someone could figure out how to take the benefits of a franchise model and apply it to the internet, there’s something there.

Greg: There’s another version of this that’s kind of on the internet. Are you guys familiar with EOS?

Sam: No.

Greg: EOS is basically an operating system for an entrepreneur. You’re a CEO running your business and you’re making it up as you go. It’s not just “building the plane while flying it” — it’s like, we’re trying to figure out what shape will fly while we’re flying it. But you don’t need to. There are best practices for how to run a company that apply to 80-90% of businesses. So this guy wrote a book called Traction, and in it he’s talking about how to run your business: “Here’s an annual plan, here’s a scorecard template you can download for free.” It’s like a full blueprint.

Sam: I’ve used it. I know a lot of people who use it. You have “rocks” — each person is responsible for three rocks. It’s this whole strategic framework.

Greg: EOS is actually quite a large business from what I understand. They have “implementers” — EOS takes the lead and then connects you with one. It’s quite expensive. What’d you do it for?

Sam: For The Hustle, I just read the book and implemented it myself. I couldn’t afford the normal thing. But it’s many tens of thousands of dollars — like $25,000 or $50,000 for the implementation.

Greg: There are people who are simply EOS implementers. They’re not part of the company but they’re basically freelancers who come and do this. From what I understand, the book Traction generates leads of people interested in implementing this. They go to the website, book a call, they buy the system or the system plus implementation, and then they’re paying a person who’s like their coach to help them implement it.

Sam: I’ve noticed it tends to be more beginning entrepreneurs. The best operators I know weren’t typically the ones telling me they used EOS.

Greg: I’ve had this craving to do a lightweight version of EOS. I have a system that works for me, I’ve fine-tuned it for 15 years, and every time I meet an entrepreneur with some bottleneck I can trace it down to the root cause. Usually there’s something in their process that’s causing them to run into this issue, and if you fix the process you fix the issue. But I don’t want to run a giant consulting company. If there was a franchise model where people could come to my workshop or seminar, do a four-week certification process, learn exactly how to do it, and then go do it on their own and make their own money — I would do something like that.

Sam: I think that’s how EOS works. And I wouldn’t be surprised if that thing makes $30 million a year and $15 million a year in profit. The people who are into it are obsessed.

Idea #4: Playing Field and the Luxury Newsletter [00:46:30]

Shaan: Greg, what’s this “Playing Field” thing? I go to the website and you can’t even sign up.

Greg: Nathan Barry from ConvertKit told me about this one. Basically it’s Tom Brady’s manager. He’s got a newsletter. It’s the most expensive newsletter in the world.

Sam: You had my attention, and now you have my interest.

Greg: His company is called Playing Field and his newsletter is called The Brief. It’s invitation only. I think there’s a maximum of about a thousand subscribers. In order to get on the list you have to be an NFL owner or just a really, really top player. This is part of a bigger trend — luxury newsletters. Or even a bigger macro trend: there are all these mega ultra-luxury experiences popping up for the top 1%. Like Soho House, private Disney tours, that hotel that charges $5,000 a night. You’re seeing it reflected in the market — Hermès has a bigger market cap than Nike.

Greg: I think the same thing is happening with newsletters. And I think there’s an opportunity to do the complete opposite of what everyone is trying to do. Everyone is trying to build a newsletter to get to the Hustle level or the Milk Road level. But what if you created a newsletter for the top 1% that was very niche-focused and treated it like a nightclub?

Greg: My favorite quote is Andy Warhol — I think he said Studio 54 is a dictatorship at the door but a democracy on the dance floor. I think there’s a way to bring that Studio 54 mentality to building luxury newsletters in a bunch of different spaces.

Sam: How much do you think they charge for this?

Greg: I mean, we’d have to buy an NFL team to find out.

Sam: How much are the Jets, Shaan?

Shaan: This idea — style points. Incredible. What a hilarious and incredible idea that actually makes sense when you think about it.

Sam: There was a big article in Forbes or whatever about this guy who created like the Raya of experiences. I saw this — is this the guy who partnered with Justin Timberlake?

Shaan: Yeah. Andrew Wilkinson told me about it. He went to the Grammys or the Oscars — he sent me this picture of him in a tuxedo on the red carpet. I was like, “What the hell?” And he goes, “Yeah, I was part of this service.” I forget what it was called, but the guy started it with Justin Timberlake or something, went through YC. It’s about getting experiences you can’t normally get but you can buy your way into if you know the right people.

Sam: Here’s what it says: “Someone will call him and say, ‘I need this epic party in Mexico with a private chef — just tell me what you need and it’s going to happen.’ And you’re not just going to the Beyoncé concert — you’re going to get into the dressing room, hang out afterwards, or she’s going to call your kid onstage.” These one-of-one style experiences. The company — Mirra — only accepts ultra high net worth individuals, defined as people worth over $30 million. He says, “This isn’t the 1%, it’s the 0.003%.” You must be willing to spend an average of $1 million a year on lifestyle alone. He’s focusing on the needs of the top 10,000 people in the world. He’s like the Wolf from Pulp Fiction — the one you call in when you need that special something.

Greg: That’s for physical experiences. But I think you’re also starting to see this trend around apps, software, and newsletters as a status symbol. Raya was a great example. But superhuman is another good example — that email software that a lot of VCs use. It’s like $30 a month and it’s kind of a flex to say “sent from Superhuman.” Gmail is probably better than Superhuman, let’s be real. But having “sent from Superhuman” adds this layer of “I take my job really seriously, I’m part of the 1%.”

Greg: So I think there’s an opportunity to create Playing Field for X, but also Superhuman for X — software for X.

Shaan: The easiest version of this on the internet is NFTs. NFTs were exactly this. When NFTs were out, they were basically luxury art. I forgot who said it but: “Art is just money you can hang on your wall.” Well, NFTs were basically money you could hang on your profile. That’s why people would spend hundreds of thousands of dollars on an Ape or a Punk, because it meant something.

Veblen Goods and the Psychology of Exclusivity [00:54:00]

Shaan: When NFTs were happening, my buddy Val told me, “These are Veblen goods.” I was like, what’s a Veblen good? You guys know?

Sam: No. What’s that word?

Shaan: A Veblen good is something where the demand increases as the price increases. Most goods follow the traditional supply-demand curve — as price decreases, demand increases. A Veblen good works the opposite way: as the price decreases, the demand also decreases. This is why NFT projects can get huge overnight — if the price runs up, it puts the product in more demand. But if the price starts to crash, the demand crashes with it.

Shaan: Once you understand this, it explains a whole class of things. The first time I heard about a Birkin bag, I was like, “What’s the deal? Why is this so expensive? Why do people care?” And I’m told: well, you can’t buy it. You have to earn the right to buy a Birkin bag.

Sam: I had a cousin who flew to Paris to go to the store to try to buy a Birkin bag. She’d been working her way up, buying all these other luxury bags just to be invited to possibly buy a Birkin.

Shaan: I’m looking at used ones on some website — a quarter million dollars. And then there are other used ones for $30,000, so the cheap end is $30,000. I think it’s around $50K if you just buy it from the store. And you can have all the money you want — you can walk into Louis Vuitton and buy everything — but you can’t buy a Birkin. Why? Because a Birkin is elevated above all of that.

Shaan: There is no end to the status game that gets played with this stuff. Remember when the iPhone came out and that guy made the app that cost $1,000? The “I Am Rich” app — it was just a red light that turned on. It got so popular Apple removed it from the store because they were like, “This is not what we want.” But the fact that it worked tells you something about the psychology of people.

Sam: This is wild to me. These bags are insane.

Idea #5: Stripe Atlas for Trademarks [01:00:30]

Greg: All right, one more. Stripe Atlas for trademarks.

Greg: We recently filed a trademark. We bought the domain boringmarketing.com, and the business started scaling and we were like, we need a trademark. I don’t know if you guys have filed for trademarks, but the process is insane. It’s a pain in the butt. It’s quite expensive, and you’re navigating these Craigslist-looking sites.

Sam: Let’s explain it. What happens?

Greg: You typically hire a lawyer — so you’re already starting off on the wrong foot. Then they’re like, “We can’t just file this, we’ve got to do a search first. Do you want the light search for $300 or the comprehensive search that might actually find the thing for $800?” And you’re like, “I guess I’ll do the comprehensive search.” Then they file it. Then nothing happens. A year later you’ll get a letter saying you got approved and you’re thinking, “Was that even necessary?”

Sam: It’s very similar to what happened with Stripe Atlas. For those who don’t know, Stripe Atlas is $500 and you can basically form a legal entity, issue stock to founders, file an 83(b) election — which is super painful to do in the United States. They took something that was really painful and expensive and made it easy and cheap. And the smartest thing about it for Stripe — obviously a payments company — is that once you’ve set up all those things, they basically send you a Stripe link. Stripe makes money when you sell stuff. So you’re all ready to go, and it onboards you to Stripe. That’s brilliant.

Greg: There’s the same opportunity to do that for trademarks. The name I would use if I was doing this: Mr. Trademark. The slogan would be something like “putting you out of your misery.” I think either something like this gets bought by a Stripe, or you hold out and allow yourself to onboard to other different services. And you could expand this beyond just trademarks to patents.

Sam: I have some thoughts on patents and trademarks. I don’t know if patents and trademarks are just astrology for entrepreneurs. I’ve been at companies where we had patents — I was on the management team at StumbleUpon after they acquired my company. I find out one of the reasons I sold was because they had the patent on a recommendation engine. They had the patent on: if you thumbs-up or thumbs-down something and there’s a recommendation engine at the core, that’s their patent. AKA TikTok.

Shaan: That’s worked a couple of times on the internet. I believe Reed Hoffman and Mark Pincus — the guy who started Zynga — owned the patent on the algorithm for social media. I think they sold it or gave it to Facebook in exchange for shares.

Sam: When we bought the Bebo brand back, we got these patents with it. They had a patent for the Whiteboard feature — you could go on someone’s profile page and doodle, like Microsoft Paint on a profile. We had the patent for that. But Facebook had the Wall, which was basically the same thing. And they were like, “These don’t mean anything.” My experience is that trademarks kind of mean something — if you don’t own your trademark and somebody else does, they can tell you that you can’t keep operating under that name, which is painful. And when you sell a company, buyers like everything buttoned up: incorporated, taxes paid, trademarks in order. But I don’t think patents do anything on the internet.

Greg: So in 2012 or so, Pincus and Reed Hoffman owned something called the Six Degrees patent. Facebook bought it from them for $700,000. There’s an article called “Who Owns Facebook’s Most Important Patent” — apparently it was a thing.

Outro and Greg’s Little Life Hacks [01:08:00]

Sam: Cool. Greg, so you’re going to come on next time? Are you going to have goodwater.com or not? You’re a .io type of guy.

Shaan: You’re what? Your agency now, it’s — that was a hate crime you just committed calling him a .io guy.

Greg: All I know is I’m wearing glasses, and if that—

Shaan: Oh, here we go. S.io just joined the chat. Where do people connect with you?

Greg: It’s latecheckout.studio.

Sam: See, I knew you’re not a .com type of guy. You have Late Checkout. Substack? .com?

Greg: Yeah.

Sam: I like your newsletter. What else?

Shaan: Greg, back in the day you wrote a series of blog posts called something like “Little Life Hacks” — guarantee Tim Ferriss your life, was that it? Like ten years ago.

Greg: Yeah. Before thread-boy culture. I was ahead of my time.

Shaan: Now you see these all the time, but back then these were great. I actually implemented many of them. You did like a three-part series. It was so good people called you back for an encore, and a second encore. Go read that series if you want to love Greg.

Sam: Your first one is “dress formal when you go on flights.” Do you still do that?

Greg: It worked back in the day. Actually worked, years ago.

Sam: What else on that list?

Greg: When you’re out with people breaking bread, put your phone on airplane mode.

Sam: That’s a good one.

Greg: Pour people’s drinks before yours. People appreciate that. My buddy Cece did that to me this weekend and I was wooed.

Sam: He woed you. I saw a picture of you and Cece today and it looks like you guys are dating, so obviously it works.

Greg: I’m leaning into his arms. It definitely worked. Schedule 30-minute meetings, not one-hour meetings. You get through just as much.

Sam: I totally believe that.

Greg: This is all obvious now. I looked like an idiot back then. All these ideas might sound like stupid ideas right now.

Shaan: Good Water you could definitely make work.

Greg: I’m the guy who looks stupid in the moment but looks good in five years. A cursed life.

Sam: Well, number three on that list is to send postcards to friends. I’ll be on the lookout for a postcard.

Greg: You had one that was like: go to this little website, they have a bunch of unique gifts, and show up not on a gift-giving occasion. Just bring one of these when you meet someone.

Sam: Yeah, people remember it. Especially in Silicon Valley where the social IQ is so low that if you do any of these things — in Texas people would be like, “Well yeah, you pour the other person’s water first.” But I almost sold my last company because I gave someone a tiny Buddha and they remembered me and made an offer to buy my business. It does work.

Shaan: It’s one of those things where you’re like, “Of course I should do this.” But you don’t actually do it. And then you read it and you’re like, all right, fine, I’ll start sending gifts.

Sam: That’s the perfect way to explain it. All of these are things you’re like, “Yeah, I know, those aren’t new.” And then if you flip the question to “How many of these do you do regularly?” — instead of knowing 10 out of 10, you do 1 out of 10 regularly. That gap is why I like that blog post.

Shaan: Greg, we appreciate you coming on. You’re full of ideas. You were supposed to be solo with me, sorry Sam crashed your party today.

Sam: Things change.

Greg: I appreciate you doing this and coming with me. This was a blast. I was smiling the whole time.

Shaan: Good. That’s a win. All right, that’s the pod.