This episode of the My First Million podcast features a conversation between hosts Sam Parr and Shaan Puri, joined by guest Greg Isenberg. The trio discusses various business ideas, the recent viral “slap” incident involving Will Smith and Chris Rock, and the potential for new business models in the Web3 and crypto space.
Topics: Business ideas, Web3, Crypto, Entrepreneurship, Will Smith, Chris Rock, Startups, Marketing
The Will Smith Slap Incident [00:00]
Sam Parr: What is everyone hate on getting rich quick? Get rich quick schemes are the best. I want to get rich quick. I don’t want to get rich slow.
Shaan Puri: It’s actually colder here than the Arctic Circle.
Sam Parr: Why do you live there?
Shaan Puri: Well, I mostly live in Miami, IRS, if you’re listening to this. But I’m sometimes in a mountain town in the middle of nowhere. Sam, I saw you posted today that you’ve got about 20 acres in Texas, but I’m staring out at 95 acres of Arctic winter winterland right now.
Sam Parr: Is that cool or no?
Shaan Puri: I mean, I love I love it out here. I’m from I’m from here, so for me, it’s it’s uh it’s slow living. It’s nice. Um yeah, I love it.
Sam Parr: Is that why you look like a pilot right now in the cockpit or what what’s going on here?
Shaan Puri: I mean, Sahil makes Sahil Bloom, my co-host on my on on the where it happens pod, we we do it together and he always makes fun of this, but I’m a I’m a gamer. So, I’m not afraid I’m not afraid to admit it.
Sam Parr: Be who you are, man. Be who you are. Uh Greg, so you’re here because I don’t even know why. You were talking we weren’t even I don’t even know what we were saying. We were talking about the Will Smith thing. You had some hot takes, Sam had some hot takes. How can we start with anything else but the bitch slap of the century? Will Smith bitch slaps Chris Rock for making fun of his wife. We I think we have a different opinion on each one of these things. Sam, give me your first where were you when it happened? How did you hear about it? What was your first take?
Greg Isenberg: I was laying in bed and I hear Sarah goes, “Oh my gosh, you got to come down and watch this. This is crazy.” And I saw it and here’s the thing. I I Are you the type by the way? Do you just go or do you wait? Do you ask, “What is it?”
Sam Parr: No, I go right away. I can tell. All right, that’s a good guy right there.
Greg Isenberg: So here’s the thing. Listen, I tweeted about this right away and people were like, “Well, what would you do?” The truth is, maybe the same thing. I maybe would do the same thing. But that’s wrong. And if I would have ran up there and bitch slapped Chris Rock, I would have been tackled and taken away and he should too. That’s what should have happened. I wanted to see him tackled and taken away or at least not allowed to be on stage for five minutes to an accepted award. That is ridiculous to me. I cannot believe that happened.
Shaan Puri: Greg, give me your where were you? What was your initial reaction?
Greg Isenberg: So my girlfriend text me and she’s like, “You’re not going to believe what just happened. Will Smith just slapped Chris Rock.” And then she’s like, “Wait, I don’t know if it was a slap, maybe it was a punch.” And so there was this confusion. There was this like five minute confusion where people didn’t know what it was. So first place I go to is on Twitter. I’m on Twitter and I I I looked at the video and I was like, I I couldn’t believe it was happening, right? It was like, you remember when um Janet Jackson with the whole Super Bowl thing? Yeah. Like, I feel like I remember what where I was with 9/11. I remember what happens when the Janet Jackson boob incident of the Super Bowl. It’s like And like OJ and then now Will Smith. Yeah, now Will Smith. So, I was in happy with the videos that were coming out, but I found the Japanese and Australian videos. Did you guys see those?
Shaan Puri: For sure. The uncensored, uncut versions?
Greg Isenberg: Yeah. Yeah. And and that one where uh you got a better view of the punch? Or you know, I needed a better view. It was a it was a slap though. I don’t know how good your view was. It was a slap. It was a yeah, okay. It was a slap. But what bugged me about the whole thing and and I’m glad you invited me to talk about Will Smith because, you know, that’s why I’m here. Is I think that, okay, obviously it was a douchey thing of Will Smith to do. But I was unimpressed with how Chris Rock wasn’t able to make a joke of the whole thing and he could have made comedic history and he didn’t. And I expected more from him.
Sam Parr: Wow, disappointed with Chris Rock. That is not the take I thought was going to come. That’s why we bring Greg on for the the when everybody’s zig, you zag with the new take. Disappointed in Chris Rock.
Greg Isenberg: Crazy impressive. He took it, man. He took it on the chin. He he took it. He didn’t tear up. He didn’t like when you get punched in the face sometimes, you’re not like crying, but your eyes water. None of that happened. He kept smiling and he was a pro, man.
Shaan Puri: You know, Sam, you know what happens. If you get hit in the side of the head, what’s the first thing that you feel or you hear?
Greg Isenberg: You you your ears hurt and you want to like grab your face.
Shaan Puri: Yeah, you you hear this ringing buzz and like the sound, you hear this just giant ringing and then you got to touch your face. He didn’t touch his face. And that you got to give him respect for the chin that he showed. Yeah, the round what that was a 10-9 Chris Rock round.
Greg Isenberg: But then Greg’s right actually. He had, I mean, the world was his oyster with all the potential jokes that he could have gone with, the one liners. If he had been like, “I can’t believe I can’t believe they had you and Ali or something like that.”
Sam Parr: Yeah, exactly. Could have given him the Oscar for best slap.
Greg Isenberg: Yeah, exactly. Could have given him the Oscar for best slap.
Sam Parr: You know, I don’t even know what the joke should have been. You know, Greg, what what what direction would you have gone with the joke?
Greg Isenberg: Uh, I would have said, “And the winner to the biggest bitch slap award 2022 goes to William Smith.”
Shaan Puri: Yeah, exactly. Could have given him the Oscar for bitch slap of the year.
Sam Parr: Okay, so I’m I’m outside of a cold stone. Just gave my daughter some ice cream. We’re trying to get back to the car. I don’t know if you know how it is. Getting kids in the car is like that’s the battle every day. That’s that’s the battle. In fact, there’s a great Louis CK joke where he’s like, the greatest moment of any Father’s Day is the like 30 seconds from when you close the door and you have them in the car seat and you walk around the car back to the driver’s car seat. It’s like the 30 seconds of peace that you have in that moment. That’s everything. So, I’m trying to get in the car and my wife is stopped. She’s stunned. She’s doing the like, “Oh my god” face looking at her phone, almost to there was like a cartoon character and I was like, “What?” And I can’t like, “Whatever it is, it can’t be can’t be much.” And then she was like, “No, Will Smith just punched Chris Rock.” I was like, “What?” And so then I watched the video. She made me pull over. We were driving. I pulled over to watch the the Japanese uncensored version because we just had to like debrief it in the moment. And um I was team Will Smith. I thought it was awesome, frankly. The only part that I thought was not cool, the only part I thought was not cool was that when they first said the joke, he’s laughing at the joke. So, bro, you can’t laugh at the joke, admit that it’s funny, and then basically two seconds later build up this rage and then pretend it was so uh not cool when it was you were laughing. Like, we got you on camera laughing two seconds before that.
Sam Parr: So, wait, you don’t think that he should have any consequences?
Shaan Puri: No, no, I didn’t say that. He should have consequences, for sure. Sure, lock him up, throw away the key, whatever you got to do.
Sam Parr: No, no, jail time. I don’t even think I’m not I don’t even want I don’t want handcuffs. I don’t want jail. Just like a, “Hey, Will, you can’t hit someone. You got to leave.” Like that would have been that would have been sufficient.
Shaan Puri: Well, the thing they showed uh in the in the uh I don’t know the Taiwanese cut, they had the the commercial break. I don’t know if you guys saw this. Somebody comes running up to him. I think, “Oh wow, they’re going to be like, ‘Dude, what the fuck? We need to get get you out of here. Sorry.’” It’s his publicist, just immediately giving him notes on how to how to play this. And so when he goes up for his speech, what do you know? The first line he says is, you know, Richard Williams was a fierce like protector of his family. That’s the publicist handing him the feeding him the line of how how you’re going to spin this to your advantage. Who hates a guy who protects his family? And guess what, it worked.
Greg Isenberg: Dude, I think the I watched his speech. I think he’s losing it. So in a in a way, I feel sorry for him. I I definitely feel a little sorry. He looked a little off, right? He looked a little off. He looked like he’s kind of he’s getting a little little something’s going on and I hope he can I hope he works through it and gets back. And also, there dude, him and his wife, man, that’s some weird stuff like what’s going on. Like, did you see that thing called Red Table that her show where she just like did a whole show with him on there talking about how she cheated on him and everything like that? And then she went to an award show with I don’t watch the news, but I watch everything that’s trashy like that. So yeah, I saw it. I saw it twice.
Sam Parr: Man, so like that’s weird to me a little bit. So uh there’s like a bunch this dynamic is is weird. He’s got a lot of pressure on him. I think he just kind of snapped. I think he’s working through some stuff. But dude, but so I feel a little sorry for him. Everybody everybody knows a couple that’s like this where they’re like kind of toxic. They’re like toxically in love with each other. It’s like they got some weird Bonnie and Clyde shit where they’re like they kind of like they like make the wrong decision. Sometimes they even like, you know, hurt each other’s feelings, but then they’re like, if anybody else ever tries to encroach, they like will murder for them. And it’s like, bro, where’s the balance here? It’s like us against the world. They love this like us there’s these us against the world couples and they’re definitely one of them.
Shaan Puri: Yeah, it was messed up. Do you want to talk about uh Alex Hormozi? Hormozi, Mozi? Yeah, what did you do? You were like, “Bro, I’m going deep on Alex Hormozi.” I was like, we are It would have been nice to do before we had him on the pod. You do it like 10 episodes later.
Sam Parr: I had a call with him today. Greg, do you know who this guy is?
Greg Isenberg: I don’t know who’s that.
Sam Parr: All right. Actually, I feel bad. I consider him a friend, but I don’t I don’t know if it’s pronounced Mozi or Mozi. Alex Hormozi. Is it No, Mozi. Alex Hormozi. It’s one of those things where it’s like two like you’ve known him for a decade and it’s like you can’t ask him now. No, you now you got to be like, “I just call him Moz. I just go by Moz.” because I don’t want to say his name. Dude, one of my best friends name is Siava and I don’t even know how to pronounce his last name. Um so and I’ve been best friends with him for 10 years. He’s in my wedding. Um so anyway, this guy Alex, so basically he had this company called Gym Launch. And it was really interesting because some people, and I wouldn’t call myself totally on that side, but I understand it, is they appeared a little scammy, but actually, I don’t think it’s scammy at all anymore. He ended up Wait, wait, wait. Sam, you got to describe the guy’s look first. So, he’s got he looks like a straight version of the construction worker in the village in the village what’s the village people. I mean, he looks like a construction worker. So he wears flannel, he’s got this beautiful thick mustache, long, awesome hair, like a like a Persian Samson. And he is just yoked. He’s jacked, he’s huge, and he’s like good looking and he just he’s like looks like Arnold Schwarzenegger a little bit. And he created this business called Gym Launch. And basically, you would pay either $4,000 for one thing or $20,000 for another thing. And it was for people who owned small gyms, whether that’s a CrossFit gym or a personal training gym, and he would basically teach you how to make your gym better because he owned gyms. And he would promise you something like, uh you’ll gain at least $75,000 in new revenue, but for a lot of people, he averaged that they would improve by $200,000 in revenue. But the business model that he had was crazy and the results were even crazier. So the business was by the time the business was four years old, he bootstrapped it and had paid himself $45 million in dividends. And then on the fifth year, I believe, he sold it and he netted something like 50 or 60 million dollars. And so he was like, “Yeah, I paid myself $45 million, so I had about 25 million just in cash in the bank, then we sold and I netted like another 50.” And that story alone is crazy. Is that right, Sean?
Shaan Puri: Uh, I don’t know if those exact numbers are right. It sounds like you talked to him, so let’s go with that. I don’t really know, but but yeah, you you got the the the product right. The the the the the kind of the the hook or what’s interesting is most gym memberships are like, you know, pay $20 a month and you get into a membership. And like it’s hard to sell people that. And what he was ended up doing was he was like, “All right, well, people don’t want a membership. What do they really want? They want to lose weight. They want to lose weight in six weeks or less. They want to lose weight so they look good on the beach. All right, so I’m going to basically sell you a program that’s going to make you look good on the beach in six weeks.” And he like he he got good at selling for his own gym where he’s like, “Oh, I can get people to pay like three grand upfront for like a fitness training package with nutrition meal plans and stuff like that.” And then someone pointed out to him, I think like Russell Brunson or whatever the the ClickFunnels guy, pointed out to him like, “Hey dude, instead of just opening gyms and doing this yourself, you should just teach other gym owners how to do this. Like that’s a better product is helping a gym like add 100 grand in revenue in 30 days is a better product than like trying to open your own gym and use that method.” So then he started doing that and then that’s kind of how he went. Now he owns something called acquisitions.com where he’ll like buy your business if you’re doing, I don’t know, 5 million or more revenue, something like that. Well, so he’s buying course businesses and like applying his methodology. And so, but basically what he sold was and this is where things got I went deep on. I was like, “How did this work? This is crazy.” So he basically sold not a franchise, but like an operating system. And so he used HubSpot as his back end and he would get people to sign up through these ads that he was running and you do an onboarding and you pay 20 grand and you get four months and then after the end of four months, you can decide to stay and part of the group and it’s 45 grand a year. But you get this after you sign up, uh you get this checklist of things that you have to do. So it’s like, raise your price to this, sign up for this software, use these emails, this drip campaign, get them get this many people to sign up by doing X, Y and Z. Here’s the ad campaign that you can just copy and paste and already use. And then he had a Facebook group where all the members could talk and that was it. That was the business. It was super simple and it was doing tens of millions a year in revenue and also tens of millions in profit. And I thought this was crazy fascinating and I wanted to ask you guys, what other he told me a little bit, but what other niches would you use this for? And also, does this model even interest you? It it it seems pretty amazing to me. I’ve never heard of it.
Greg Isenberg: I think that if you did this for agencies, like digital agencies, that this is a no-brainer. So, you know, we’re I run an an agency called Late Checkout. We’re about 50 people. Uh so we’re starting to really hit some scale. And as the Can you can you say your revenue? Uh I mean, I don’t want to say my revenue, but we have 50 people, so you can do some of the math yourself. Um I will say that um yeah, we work with some of the biggest brands in the world and it’s very lonely to be like the CEO of an agency. Like I don’t know if I’m overcharging or undercharging. I don’t know if I’m, you know, you know, doing the right thing. Should I be doing more marketing, less marketing? So like, would I pay 2, 5, 10 grand a month to for like something like this? Like probably, if the ROI is there. Yeah, it’s basically a sales machine, right? So what he what he said was, if you have a business and you have whatever number of customers you have, if I can get you more customers, that’s clearly of value to you. And I think he basically tried to get like capture 10 to 20% of the value that he was giving. So, you know, if if I’m going to get if I’m going to generate $100,000 in new incremental sales for you, how do I capture 10 to 20,000? And I and I’m taking the risk. If I don’t do that, then I don’t earn anything. I think that’s kind of how he started it at least. And so an agency is a perfect one like that because every client you sign is cash in the bank and um typically the agency might be good at one thing, but not necessarily good at going and getting new clients. So, what uh what you just read this guy’s book, Sean, Alex’s book. I’m reading it right now. What what do you think about it? The book is good. Uh the book is good. I it’s basically a it’s like a marketing book, right? So it’s a it’s essentially a marketing book. He does a good job of breaking things down and being simple. It’s not altogether new information, but um but who gives a shit? It’s like it’s good information, presented well, and if you’re running a business right now, it’ll help you. Now, the thing I think that he overindexes on is like he uses like the Gym Launch example really hard. So it’s like, yeah, this this is clearly he he talks about basically he says you the secret to sales is make somebody an offer so good they they’d be stupid to refuse you. Okay, how do you do that? It’s like, how do you get them to perceive that there’s a lot of value and that they’re going to get it in a short amount of time with a with a with not a lot of cost and that it’s highly likely to happen. And so his model was like, “Hey, gym owner, I on I’ve worked with 100 gyms, on average I can bring them each 100,000 in new new sales. I can do that for you in 30 days, and if I don’t do it, I don’t if I don’t hit that mark, I don’t get paid. How’s that?” And so yeah, that is what he calls a grand slam offer because it’s going to work. And if you make if you have a grand slam offer, you can win a lot of business. You can grow very fast. But I don’t think that works in a whole bunch of other product categories. So I think it works in the like agency consulting world, which is where he was. Services, I think. It works in Services, yeah. But you know, if I’m selling shoes online, it’s very hard to create a grand slam offer for selling shoes because uh you know, I can’t tell you how much more money this is going to make you, right? So already the offer is a lot less. I’m telling you, it looks cool, you know, that that people might like your shoes. That’s just fundamentally less compelling. So I just think it’s like really, really good for a service business, um especially a service business that’s in in the business of helping other people make money. But uh like if like for example, I wanted to send it to my accountant and be like, “Hey, you’re charging me like five grand or six grand a year, you should really be charging 50 grand and if you did this method, I think you would have, you know, like 10 times more clients and make 10 times more money off them. Um if you presented your stuff this way, because you’re an accountant, you’re saving people money on taxes, and you could basically offer a no-brainer offer like this and take more value and grow your business faster if you did it this way. But um it doesn’t work for everything. That’s kind of the the takeaway. I think the pitch I think the the pitch is is taking a consultancy from a consultancy and turning it into selling luxury. Like that’s the opportunity for a lot of these people, right? Like I think uh when you look at McKinsey, McKinsey is in a consultancy to me. McKinsey is selling like a luxury multi-million dollar contracts. Like that you’re buying confidence when you’re buying uh Right. a luxury product. Yeah, that’s exactly right. He talks about that uh pretty extensively in the book. But I got to say so I I have reading this book and I have two kind of like my two like my right hand man and my left hand man. I have I have Ben and then I have this guy Andre. And I told him I was like, “Guys, is this good stuff in this book that we should be using?” Uh and so I created like a little mini book club inside of our company to do this. Have you guys ever done that? Like have you have you basically and I’ve been wanting to do this with podcasts as well. Sometimes I’ll listen to a podcast that’s like fucking amazing and I what I want to do is just stop listening to it myself and be like, “Hey guys, we’re going to do a meeting, but the meeting is us listening to this podcast and every time they say something good, I’m going to pause and we’re going to talk about it. And it might take us like six hours to get through this one hour podcast, but I’m telling you, it’s going to be we’re going to actually apply the thing versus just, I share the link, you read it, I read it. We each kind of move on with our day and we’re busy. Have you guys ever done anything like this to like get more juice out of the out of the fruit? I haven’t. I haven’t. I’ve done a book club uh that I feel like book club is it’s like, you know, a lot of people go to the gym. It’s like you start going to the gym and then you kind of like stop. Like it’s really hard to create a really well-designed book club that keeps people engaged. Yeah, we did book club, but it was the same thing. No one fucking finished the book. So I actually think if we all just listen to a podcast together, it might be a lot easier. It’s a lot easier. It’s like when you go to school and the teacher brings in the TV. Uh that’s like how I would feel going to this meeting. I’d be like, “Oh, hell yeah.” Rolling in the TV. Magic school bus, baby. The um yeah, at Amazon they do this too where like uh people write all kinds of docs inside companies like memos, plans, whatever. And then it’s like, “Hey, did you read my plan?” And then you’re like, “Oh, yeah, either I kind of did or I didn’t.” Very rarely is it like, “I read it, I remember it, I took notes on it and I’m ready to take action from it.” And so at Amazon, they basically hack that process, which is the rule is you have to write if you’re going to make a plan, if you’re going to try to do anything, you have to write your memo. But the memo gets read in the meeting itself. So every meeting, if it’s an hour, the first 10 to 20 minutes are silent reading. Everybody reads it together at the same time and there’s zero expectation for you to ever read something beforehand or afterwards. So they like bake it into the meeting itself. Oh yeah, it was it was huge. Uh like and also while you’re reading, you’re, you know, you’re taking notes because you know right after this reading period ends in 20 minutes, like it’s a bit like school. It’s like, I’m going to have to have something to say, right? Like I need to have I need to be bringing something to the table from this. And so um yeah, that was huge and I think more I think way more companies should do that. It was like one of the few big company things that I was like, this is a process that is so much better than what I used to do at a at a at our startup. Yeah, well, I think that podcast idea that you just had is actually fantastic. Um cool. All right, we lost Greg for a second, but let’s let’s keep going. Um did you have anything more on Hormozi or you wanted to to go on? No. That’s it. What do you got? I was thinking about doing a like a a kind of like a summary/ lessons learned because I have a whole bunch of like screenshots and highlights from the book. I might do a separate pod that’s just that if you want to do that. I’m down. I just I just I just bought the book. I’ve been watching a lot of his YouTube videos. There’s just something about this person. He’s very interesting to me. He’s very interesting. He’s so transparent to the point where it’s weird almost. Like I’m it’s like I I like he reveals so much. I almost don’t believe you. Uh no, I believe him. I believe him for sure. But he’s revealing so much that I’m like, “Are you sure, man? You want to be talking about this? This is crazy.” Like you you like it’s just weird. It’s just weird, right? I mean, he talks like I don’t think it’s weird. I think it’s smart and that’s why I say like, uh do I believe this? It’s not that I think he’s lying about anything. I think he’s telling the truth. It’s that when somebody is that forthcoming, it’s sort of like, “Well, what’s in this for you?” And I think clearly it’s I’m trying to get you to trust me. Um and so I’m going to be like kind of like explicitly transparent about something because I there’s a there’s a motive behind that. And I think that’s okay. Uh but I think a lot of people are like, “Wow, thanks, dude, for the favor.” It’s like there’s no favors. Um people do things because they have a motive. They want to build their brand in a certain way. They want to attract more more readers or viewers or they’re trying to build trust in a way so that they can get some advantage, you know? And that’s okay. I think that’s a it’s a good thing. I I do it too. I do it all the time. Yeah. Um Yeah, I’ve got I’ve got to know him over the past few weeks. I I’m a fan, man. I’m a fan of Alex’s. But what do you got? Uh well, actually, we should so Greg, I I told you bring three or four bullets. I don’t know if you had time to do that, but I I have some if you don’t have any, but I’d like to use yours if you do because you’re here. You’re the guest of honor. Yeah, I mean, I always have a a notes file with some ideas. I can tell you I’m not going to say they’re great ideas, but let’s let’s start with that and I I’d love your feedback. Okay. All right, let’s do it. Um so went to a restaurant uh two nights ago, saw that a bunch of kids were playing these like picture like an Applebees and picture a bunch of vending machines. Um like you know those games that you can play. I’m thinking NFT vending machines. So you have to pay like 100 doge to get in. You can win a board ape. Um instead of winning, you know, collectibles, you’re winning digital assets. Is there a business to be created around that? You’re talking about the thing where you would like the old way is you, you know, you put your quarter in and there’s a bunch of plastic balls, you get one out, you got this little shitty toy and it’s like I think in Japan they call these the Gacha games. Is that right? Uh like Gacha mechanic where you have this sort of variable reward. You might win the good thing, but you almost never win the good thing and then you kind of keep wanting to open up these boxes and see what you get. Exactly that, but with doge. And winning an NFT. Do you uh And NFTs inside. Greg, do you own any NFTs? Are you on board with this or no? Yeah, I mean, I’ve got hundreds of NFTs. That’s crazy. Yeah. I think the problem is doge. I think not enough people own doge. Um you know, so I I kind of feel like it’s like you need to Apple Pay to quickly like instantaneously buy doge and then use it use it in the game basically. Like you need some way for their phone to just buy the thing and then just keep swiping their phone basically. Yeah, I guess like what I’m particularly interested in here is like what are you know, in real life experiences that you can create that connect with crypto. Mm. Yeah, another version of this by the way, because I don’t need a restaurant anymore. I just deliver everything. So it’s like um you know, a QR code that comes with DoorDash that I just scan and I get to play the game on my phone, right? Like why do they need to buy a screen when I carry a screen in my pocket? So like really all you just need is a QR code to do this game. You don’t even have to build the you don’t even have to build the vending machine necessarily. It’s true. It’s true. Um all right, I got another one. So I moved out of my apartment December 15th. It’s now March 28th and my landlord hasn’t returned my security deposit. Is that in America or It’s in Florida. Yeah, Miami. Ooh, there’s a bunch of laws around that in California. Well, there’s laws around it in in Florida, too. And I Googled it and there’s a whole process you can go into and I’m sure it’s probably not as intense as California, but you know, you have certain rights. Um there’s a whole process that you have to go and eventually you go to small claims court, etc, etc. What How much was it? Uh it’s a few hundred dollars, but it’s just like the pain to like go through it. It’s not really worth it. My security deposit is $5,700. Um so what I really want to do is scare my my landlord, basically, right? That’s what I want to do. So I want to I need to get his attention. That’s what I really need to do. Um so I Googled um you know, sending a lawyer letter. I didn’t want to call my lawyer because I was like at $750 an hour or whatever. It’s going to cost like two grand for this lawyer letter. So the idea is a $99 lawyer letter on demand, go scare go scare someone basically. What do you think? Have you um Scary letter. I love it. So listen, we got to talk about this, Sean. You know where we’re where I’m going to go with this, right? Do not pay. You’re going to petty court? Oh, I like petty court. Oh yeah, do not pay. I’m but I’m going to go Do not pay. Greg, have you not heard of do not pay? Yeah, so is is do not pay that service that like if you have a parking ticket, you like send it to them and they like they deal with it and you get a percentage of it back or something like that? They do a bunch of stuff, but that is one of the ways how they started. How do you explain this company now, Sean, now that it’s kind of they have so many features? Yeah, I think it started it basically it’s it’s just trying to save you money from shit that you you shouldn’t have to pay for, you don’t want to pay for. So it started with like subscriptions you’re not using. All right, cool. Unsubscribe me from a bunch of subscriptions I’m not using. Then it became uh then they also added, you know, like go contest this parking ticket because like I don’t know, 20 or 30% of parking tickets are like filled out incorrectly and you actually shouldn’t have to pay. And if we save you money, we will keep a little bit, but it’s just you do not work. And you’ll get uh they just keep a portion of the savings that they get that they earn for you. And then they expanded into like 83B election. Like, “Hey, we’ll do that for you for your startup.” So they’re just like trying to do they’re basically just trying to eliminate the busy paperwork that nobody wants to do and they’re like, “We’ll just take care of that shit for you.” How would that feel? And a bunch of like people like us who are like millennials who are like, “Ah, I just don’t know how to do it. I don’t want to do it. I don’t like printing things or going to the post office and like doing all this shit. Yeah, please take care of this for me.” So it’s a time saver company is how I think about it. And Greg, I had a landlord, I had a $16,000 deposit. This was for our office uh when COVID hit shut or our office lease just so happened to end right around when COVID was happening. So we got really lucky and we just canceled it. And this guy would not give me the 16 grand. I found out Dude, I got crazy on him. I found out where he lived and I showed up at his house and he wasn’t there. I found out where he worked and I showed up there and he wasn’t there. And I used DoNotPay to send him like a like a letter and finally he got back to me. He was like, “Oh yeah, you know, just slipped my mind.” Like he was like, “No big deal about it.” And I was like, “Dude, I’ve been hounding you for six weeks, man. Where’s this money?” And he So they they have that feature where you can just send a scary letter? Yeah. You send a scary letter and uh it worked. And so uh we we I got my 16 grand. But legally, you’re supposed to get 16 grand plus interest, which I did not get. And I uh I thought about like fighting over this just out of principle because I love petty shit. So, I feel like the idea is really, you know, do not pay obviously is getting really big. It’s like the unbundling of do not pay and it’s taking this idea and it’s like, “Okay, I’m going to run a bunch of Google ads against like getting security deposit back, Florida, getting security deposit back, California.” And I think there’s a big business to be created here because then that’s a that’s a good wedge to sort of expand a bunch of different services. And I think there’s the other version. I think we we once said, which was like, uh call my politician. There’s all these things where it’s like, “Ah, this bill could get passed that’s bad for crypto holders. Make sure you call your politician and and let them know you don’t want this.” And it’s like, “Ah, I’m not I don’t want to call my politician and like who what if they pick up? What am I going to say?” You know, like there’s like there’s all kinds of problems with this idea of calling. I don’t like calling. What happens if they pick up? You know, I I really want to go down that road. But I would happily, you know, sort of tip, you know, 10 bucks to just have someone annoy the shit out of my politician about this issue that I care about. Um like if my donation funded like 18 annoying calls, like if there was just a website that said, “Would you like to donate $10 to the cause and that will fund 18 annoying phone calls from Sri Lanka to this politician?” I’d be like, “Fuck yeah, put me down for 20.” And so I think that’s the other version of DoNotPay, DoNotPay is like, “Go hassle for me.” That’s awesome. I’m on board with that. Can you uh What else you got, Greg? My other one, I it relates to law, actually, a little bit. So, you know, we’ve been and I Sean, I know you’re into crypto. Um so I’ve been spending a lot of money on, you know, crypto accounting and crypto law firms. Um and I think that there’s an opportunity to create a Web3 crypto accounting firm and a Web3 uh crypto uh law firm. But all you have to do is basically you find an existing law firm that understands securities law and you’re like, “Hey, you know, you you you’re your shop of 10 lawyers and and you’re like, you know, you understand securities law. Maybe there’s some, you know, upleveling in terms of learning specifics about NFTs, etc.” I’m going to be the like marketing engine for you. You know, use things like the Milk Road and use things like Late Checkout. And I’m going to uh send you leads. Um so the customer is happy because they’re like, “Wow, this is like a Web3 related, you know, law firm and I want to work with someone who’s What does that mean? I don’t know what you’re using. You’re using words that I don’t have no idea what they mean. What does a Web3 related law firm mean? Okay, so let’s just say you’re creating an NFT project, but you want to make sure that you don’t go to jail. So, let you don’t do any SEC violations. Do you feel comfortable calling up your regular lawyer who’s might not even know what an NFT is, or would you specifically want to talk to a law firm that lives and breathes Web3? It depends if they have um what’s like for example, if I what what’s the term? If I follow something my lawyer says and they’re supposed to be the expert and I get in trouble, sometimes I can like blame them. Um what’s that called? God, I can’t remember that. I can’t remember, but but but it’s scapegoating. Yeah. No, it’s like a it’s like a it’s like when you hire a it’s like when you hire a if you hire a CPA and your CPA screws you like blatantly, sometimes you’re not always you you can you know, that goes that you’re taking to account like, “Ah, dude, I thought he was doing it right and he’s a CPA.” So, like your CPA can actually get in trouble, not necessarily you. So, it depends if that lawyer has that. But I don’t know, I’d rather just go to a legal for a lawyer that special Yeah, that specializes in this thing. But I don’t know why you’d call it a Web3 That’s what he’s describing. But he said a Web3 law firm. Yeah, like they specialize and they they know the laws around they specialize in advising. Okay, I think you meant like around this. Web3. Not a digital law firm. Yeah, okay. Yeah, all this is is like, I mean, this is a marketing challenge more than anything. And you know, one of the hardest problems about running a law firm is, you know, or an accounting firm is getting clients. And we talked about this with the agencies, the same thing is true with, you know, law firms and accountancy firms. I think, you know, I don’t know the like I I don’t know the margins of some of these businesses, but I imagine they’re quite big. Um, so I think there’s something there. So I considered doing this with my before I did the Milk Road, I was like, “All right, what do I want to do? Like I got this audience that’s growing, right? It’s like Twitter’s Twitter’s pretty big now. It’s like I don’t know, quarter million followers, newsletter’s growing. I could just like, you know, make no money off this. That’s fine. How big was your newsletter? I could put some ads in the newsletter. That’s What’s that? How big was the newsletter? It was like at 30 or 40k or something at the time. Before Milk Road. Oh, I could put something there. Oh, I I Yeah, before Milk Road. And uh and I was like, “I could teach a course.” So I did that. I taught a course. I was like, “All right, that’s cool. It makes way more money than ads, but it’s more effort.” And then I was like, “You know, what’s like the highest value business? What’s like the best fucking business?” And I was like, “So I started making a list of like places where I spend a lot of money that I feel like they’re just kind of like rinse and repeating the same stuff for me.” Um and so I I I narrowed it down to two. I’ll give you the second best one was accounting. Um and I was like, “I could just start a bookkeeping firm for uh for startups and entrepreneurs.” Just in my own portfolio, if I if I invested in 45 companies last year, just within that, I bet I could get 14 clients of just companies that don’t have a bookkeeper because most companies don’t have bookkeepers. So right off the bat. You were You were considering starting a bookkeeping service? That’s like the worst idea Yeah, I was like what’s the most boring thing I could do? for you. That’s a horrible idea for you. No, it’s great because I was just going to be the marketing front end. I wasn’t going to operate it. I was just going to buy or hire like a good bookkeeper and be like, “Cool, you’re going to do the books and I’m just going to send you clients and you just close the clients and we split this 50/50 or whatever.” And um so that was one idea. The the better idea is insurance because insurance is like the best business of all time. And um because for insurance, you don’t even really do insurance. You just broker the insurance with another like carrier basically. And um and most businesses don’t have uh most like especially like e-commerce businesses, you need business insurance and you don’t know exactly like I didn’t know exactly which insurance I needed, how much, uh how much coverage I wanted. Most traditional insurance firms don’t cover e-commerce, which is insane to me. And so I was like, “All right, well, I could just do that.” And so that was another one which is, you know, startup/e-commerce insurance was another one. I I basically did the math and I was like, “I could make so much more money doing that than if I ever did like ads in my newsletter. If my if all I did my ad was say, ‘Hey, by the way, don’t go to jail. You should have a bookkeeper.’ You know, like, ‘Hey, um don’t lose your business because somebody, you know, whatever, chokes on a button.’” That That What What was your math for the insurance? What was your math? That First of all, I think that’s I think you made 100% the right move doing what you did because those businesses do not fit your skill set or mine at all of like insurance, like that like being on top of things like crazy amounts, sweating the details, But you’re assuming you’re going to run it. I’m not going to run it. You’re going to be I’m just going to find a good person. You and I both know that’s a bad lead. I’m just going to send them leads. But all right, so what was your math behind it? Uh I don’t know. I have to pull up all the spreadsheets, but basically, just with my existing audience size, I think it netted out where it’s like I could be easily clearing, you know, three to five million dollars uh a year in profit if I like kind of like hit hit all my marks. Tell me more about this. This is actually really Full full capacity. This is actually really interesting. So what are we going to call it? Like Sean Churance? What was the name? No, it’s going to be something, I don’t know. The name was the last thing on my mind. Okay, so I even talked to the I I had this one lawyer one accountant who I really love. There’s this like Ukrainian woman who’s like this like amazing accountant. She was the first accountant I talked to that felt like they worked for me and not like as a they weren’t just like a narc. And so they were like, she was like, “Have you thought about this?” You know, like, “Does your business need a vehicle?” Because I think right now, just last week of the year, if you just bought a vehicle, we can actually like depreciate that and use that against your books here. Like, she was giving me ideas that were completely legal, but she wasn’t just sitting there and saying, “Yeah, if you give me all your paperwork and your receipts, I’ll uh I’ll file your taxes for you.” It was the first person who was saying, “Wow, you’re paying a lot in taxes over here and over here. Um let me just make sure I’m, you know, saving you money.” And so that was the first person so I was going to basically talk to her and be like, “Hey, should you do this? Uh like do you want to do this? Do you want to like leave? Start your own firm. I’m sure you’re scared of all that. But guess what? Uh you would just do the thing you’re really good at, which is doing people’s, you know, like tax strategy and accounting, and I will get you all the clients.” That was, you know, the core premise. But of course, I I went down I said I created a free crypto newsletter uh because I just figured it’d be more fun. Dude, I think these are great ideas, by the way. I think you made the right decision, but these are actually This is crazy interesting. I wish you would have told me that you were working on this. Can I tell you about a a fucking genius idea that came out of that? So, um have you, I don’t know if you’ve ever like onboarded, well, like you’ve probably done some onboarding with some some software that you’re trying to use or some company you’re trying to use. So, for example, with this with this bookkeeping company, right? The one I hired, I eventually hired for my e-commerce thing, they sent me this like super long checklist. It was like, “All right, um great, excited to work with you. Do these 54 things and then we’ll get started. Like that will be the start of your journey. That will get you to the starting line.” It’s like, “Go to Shopify, give us access. To do that, you need to go to view accounts, permissions, add us there, add us as a bookkeeper, blah, blah, blah. Now go to QuickBooks, do the same thing. Now go to Stripe, do the same thing. Now go to Bank of America, do the same thing.” Like, and there was just all these fucking steps. It’s like, “Then send us this, then send us this.” And it just felt and it was all done in Excel, right? So I discovered this startup that basically takes that process and just wraps a beautiful user experience around it. And I saw it and I was like, “This is so smart.” I invested in instantaneously, didn’t have a meeting with the founder. I was like, “I totally buy it. In fact, any word you say is only going to make me less bullish on this idea because I’m already convinced this is like one of the best ideas I’ve ever seen.” So it’s called Doc, so it’s doc.us. I don’t know if you guys have have checked this out. Um and uh Julian, Julian Shapiro sent this to me after I was like seeing this problem and then coincidentally he sent me the same idea. So so here’s how it works. So basically, it just creates like kind of like a notion space. So the company who’s trying to onboard you, they just create this thing that’s like, it’s like this just a beautiful experience. It’s like, “Hey, Sean, so glad to have you on board. First three things we need you to do are these three. Click the checkbox when you’re done with them, so I’ll know that you did it. If you have any questions, just put it in the comment thing here, or click this to watch our tutorial from our library that we have about how to do it.” And so it just turns that like back and forth email or like Excel spreadsheet like um janky thing into like like workflow for a client and um and a service to like onboard each other. And I was like, “Dude, that’s a problem that like, I don’t know, like I don’t know, two million businesses a year have with every one of their clients.” This is going to work. I think this is going to work. What do you guys think of this idea? Brilliant. Well, I love it. I just I just bought a a mortgage um after my landlord stiffed me. Same thing. And, you know, I go on to Chase’s website and I don’t know if you’ve done this, but you go go on Chase’s website, you go to the mortgage and there’s like a thousand things to do, plus you’re like transported back to 1996 because you’re in this like weird thing. There’s like JavaScript breaking everywhere. There’s like you like forgot about Flash and like Flash is somehow in there. Uh my my my uh banker calls me and just like, “You didn’t finish this one thing.” And I was like, “What?” She’s like, “I added it to your client portal.” It’s like, “Dude, I don’t get a notification. I don’t I don’t go check that. I hate that place. I fucking hate that place.” Yeah. So, yes, yes. This is one of those no-brainer ideas. I I hope that they they actually embed like create an SDK. They do. Okay. I I I I I think I don’t know if they already do or they’re going to, but that was like a big part of Yeah, I was like, this can live inside of your app or whatever. So you, you know, you uh you can just kind of like onboard people right there inside their experience. This landing page is beautiful. This is a beautiful website. Yeah, so it is absolutely beautiful. But I have a question for you for you guys, um because it it relates actually to to this and also Gymshark and even the the lawyer stuff, which is you know, sometimes when we’re creating businesses, you can do one of two things. You can either like create something brand new, which is like this, um or create like a new gem, like a new way of, you know, doing something, or you could like help existing people, you know, do some marketing, make some money that way. Do you guys, you know, and the Silicon Valley way is is very much like go raise a bunch of money, invent something new, um and it’s really frowned upon to do, you know, the marketing piece of it and sort of positioning on top of it. Um what are your thoughts and, you know, do you think about that a lot? You know, because I’ve been thinking about it a lot. Say it again. Give give us two examples. So I’ll give you an example. So um you know, my last company, the founder of 24 Hour Fitness invested in my company and he told me that before the 1980s, there weren’t membership-based gyms. Like it was a new thing. Um and he invented the first one and it became 24 Hour Fitness. I think they sold for three or four billion dollars. It was a major success. And then there’s a lot of people who copied membership-based gyms. That’s an idea of going zero to one, creating an absolutely new product. Whereas what he could have done was created a Gymshark of that era or whatever and consulted Gym Launch. Yeah, exactly. Gym Launch, sorry. Um and consulted to, you know, add additional revenue to existing, you know, trainers, etc. Um so the question is, do you, you know, how often are you thinking about creating something brand new versus, you know, just kind of a money-making additional marketing layer on top of. Sam, what do you think about that? I don’t think I think of anything that I think of I don’t think any of it’s brand new. I think zero. Close to zero, I think about that. Do you agree, Sean? Um, no, I think there’s sometimes new things, but it’s extremely rare. It’s extremely rare. Extremely, extremely rare. But I would even argue that most anything that’s new, you could probably actually say, “Oh, well, it’s just like a different version of blank.” You could trace back, right? So like, let’s take a Airbnb for example. Airbnb was clearly like kind of like this breakthrough product, became this huge success and it’s like the category killer, the category leader for sharing economy, whatever. Um and it now it’s like bigger than hotels, like than all hotels or whatever. So it started off as this fringe thing. But there was like couch surfing before that and like that was like a product that did a very similar thing. Um you know, and VRBO and there was there’s other stuff that’s like around it. So I think you’re right that it’s very hard to do something completely original. But let me frame it slightly differently, which is it seems like what Greg is almost saying is like do you want to go for uh try to try to have either a new behavior or an existing behavior? Or another way of looking at it would be um do you want to create a product or do you want to have a service company, right? Like it’s kind of to me that in those examples, it’s like 24 Hour Fitness was a new was like a new product you needed customers to go buy versus servicing, you know, trainers and and and whatever, whoever else. Um that was that’s like a service business that’s going to have great cash flow and doesn’t require you to have this like winning brand and new product and new customers from scratch. Is that is that kind of is it more about the services versus product? Is that the Yeah, exactly. Yeah, I think um you know, Sean and and um Sam, like, you know, having spent time in SF, I feel like when I got to SF, I was all about new behaviors. Um that was really important to me. And Sean, I know that was true for you too because like Blab, you’re always pushing, you know, the envelope with like, you know, and Bebo, it’s like new, you know, user interfaces and like new friend finding and new just like new ways of doing things versus now that we’re in our 30s, it feels like we’re doing less and this is just an observation and correct me if I’m wrong, but it feels like we’re doing less of like the new behavior type stuff and more of like, “Hey, let’s just like iterate on this thing and like focus it on this niche and and and do that.” There’s this guy named Roger Dickey. I don’t know him. I think Sean knows him, right? Uh I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier than the last. It’s like, you know, and it all appealed to me that way. And now I’m like, “Cool, I can um sell a product that I, you know, maybe import a product from China and sell it through a Facebook ad, I click three buttons, I can just sit in my chair and do that. I don’t really need a staff. I don’t really, you know, I’ll just kind of outsource this and that. I’m just going to write a newsletter um and I’ll just write it in my browser and then that’s it. Uh like I don’t have to like become the next Mark Zuckerberg. I just need to get to like enough people where I’m making a few million dollars a year and living a sweet lifestyle. Um like that’s that’s a win, you know, and that’s a and I don’t have to manage anybody and I don’t have to like stress out about this thing and I don’t have to know how to code. I don’t have to know any of these things. Oh yeah, great. And so I basically now I’m in the the sort of sandals resort part of my career. And I mean that in the best way possible, which was back then, I was like almost like intrigued by the degree of difficulty. And now I’m completely put off by the degree of difficulty. And instead, I just do the thing that sounds like what’s going to be easy, simple, fun for me. And um and you know, I’m just going to go that route. And so I am much less interested in like inventing the next big thing as I am like crafting a dope lifestyle doing something I enjoy. Do you think that’s going to change? But do you think that’s going to change when your kids get older? So when your kids become 8, 9, 10, maybe 8 to like 16, they think that you are the coolest guy ever or if they don’t think that, maybe it’s on the other end of you wanting to think that you’re cool and you want to impress them. Um and I’ve been thinking a lot about that lately. I’m like, “Do I think that my attitude will change when my kids become 5, 6, 7, 8 and I want to impress them?” Do I think like instead of just like having a sick lifestyle, I’ll be like, “Oh man, I want to do something like that they are proud of.” Do you think that’s going to change? Not because of that reason. I do think it’s going to change, but not because of that. Like uh I don’t think your kids think you’re cool based on like your business success necessarily. I don’t I don’t really think that that’s the the main the main way that kids think you’re cool. Um and I even if it was, that’s not why I would do something. Um I would just have more free time, right? Like when my kids go to school, that’s going to be like a fucking game changer. It’s like I’m going to get a third of my day back uh that I you know, I don’t have today. And so when they go to school, I have a lot more bandwidth. If I want to do something more intense, I can ratchet up the intensity and the difficulty level if I so choose uh at that time. Right now, like, dude, before I do this podcast, like I’m not uh I’m not like you know, researching every detail for the 20 minutes before this podcast typically. I’m like reading a this book called Goofy’s Adventure to my daughter, putting her down for the nap. You know, like that’s how I prep for this pod. Like 20 minutes before is like I’m literally reading Disney books, putting my daughter to bed in time to come back out here, right? So it’s like there’s a lifestyle I like right now that’s doing this. And so I’m optimizing for that. I think in five years, I’m going to be picking a very different challenge than I’m picking today. Just because it’ll be time for another chapter and I’ll probably be like, “Oh, that lifestyle shit’s boring. I want to go do something big.” Or I’m going to be like, “Fuck business. Business is stupid. I’m going to go like try to write a comedy show and I’m going to like try to sell a show for TV.” Like I don’t know. I’m going to do something else with my life. Every five years I want to kind of reinvent myself in terms of what I’m doing. So, you’ve come a long way, Sean. So, one of the first times I met you, you invited me to the Bebo launch party. And I invite I was like, “Can I bring a plus one?” You’re like, “Sure.” I bring this friend who is visiting and we walk into this warehouse or something in San Francisco. I remember we had to like walk upstairs and like Where was it, Sean? It was in a uh you know, like a car manufacture a car uh repair Yeah. like like a garage that’s like for car repairs, whatever. I don’t I don’t know. I forgot how to speak English. But like basically, Michael had bought one of those, like got rid of all the car like car maintenance stuff and just turned it into like his man cave. And he hadn’t filled it up yet with his his like fancy cars and cool shit yet. So it was just an empty warehouse in the middle of San Francisco, downtown San Francisco, and we threw our launch party there before he filled it up. So, I’m there with one of my buddies from this small town in Quebec. The guy has never left his town basically in his entire life. So he had lands in San Francisco, he’s staying with me. He gets into this, you know, car shop or whatever and it’s like dark and there’s smoke and there’s lights everywhere and then you walk in and there’s all these people and there’s lights everywhere and he like literally whispered to me and he said, “Is Kanye West coming to this?” Did you say yeah? I should have said, “Yeah.” And it was like the one of those moments like I’m sure a bunch of people have like watched the social network when it’s like Justin Timberlake is like talking to uh uh I guess it’s uh Mark Zuckerberg in the club and it’s just like it’s intense and It’s like larger than life. larger than life and you were kind of like living that lifestyle in San Francisco. Not like I mean, I I’m painting you as very playboy and I won’t tell you you’re 100% playboy, but um in the sense of like you were living that lifestyle, you were you were doing that like Zuckerberg thing. And now um you’re not you know, you’re kind of doing the complete opposite. And my question to to to actually both of you, but particularly for Sean, is if you could redo it, would you have done more more of these product bets that are uh there’s it’s really less risk. Like for example, Milk Road, like there wasn’t that much risk there. Yeah, let’s yeah, let’s be real, right? So like I feel like people like we’re now that we’re in our 30s, we’re focusing on different niches and we’re taking things that are working, different communities and we’re just pushing that out there with you know, low product risk. Would you have done that or do you think that you needed to do these crazy bets in your 20s to to to be where you are today? I have a very easy answer, but I’ll let Sean go first. No, no, go. No, I want you to go first. I want to hear what you’re going to say. Playboy Sean. Well, as Playboy Sean, by the way, for that, I flew in this painter that I had met and he did a I don’t know if you remember this, he did a live painting where he he’s painting this like abstract thing. He’s break dancing while he’s doing it. And this is a guy I had seen at a at a fair in Greely, Colorado, many years before that. And I was like, “Hey, dude, I have like a like I have a company that has like a bunch of funding. Like you want to just like fly out for this party and do something dope? Do that thing you did at that little town fair. Do it in front of a like hundreds of people at this thing.” And he’s doing it and then he had the end, he spins the canvas and what looked like this crazy abstract thing was he had painted like a fucking Bob Marley upside down. And it’s like he does this like whatever, he flips the thing and then he’s like done and he slaps it with his hand and it’s full of paint. And it was like, “That was the moment.” And I was just like, “That party was dope. That was a dope party actually, now that I remember it.” So, do I regret it? Well, now that I’m thinking about that party, no, I don’t regret it. That’s that was pretty awesome. I’m glad I did it because I’m happy with where I am now. Having said that, there were so many things that I did foolishly during that time, and I’m not just talking about like, you know, “Oh, you know, I wasn’t as good at this thing as I am now.” It’s like, no, like there was so much opportunity right under my nose and I was blind to it. And like one of the biggest like scary things for me now is like, what are those things today that are right in front of me that I’m too stupid to see, just like I was too stupid to see it seven years ago when I was doing that other thing. Um, for example, Greg, you were in our early mastermind groups and the founders of Calm were there and they were talking about how hard it was and how they’re just, you know, it was just Alex and it was just kind of like, “Yeah, it’s hard to raise money right now. I’m trying.” And and we were just like, “Dude, it’s cool app, man. You should stick with it.” He’s like, “Yeah, I’m I’m going to just keep going.” And like that’s a $2 billion plus company now and we were helping him like Dude, why didn’t we cut the check? You were there too. I don’t know. You didn’t take cut a check either, did you? I I remember at the time, like if I’m being honest, like I felt that it was too niche. Like I was like, we were like, Sean, you and I were focusing on like We were doing big stuff. Stuff that was going to be big. Yeah, exactly. Here we are. All one acquire later. And he’s he’s got the huge company. Exactly. Uh there was so many of those. So in our masterminds itself, I think uh Loom was in there. That’s a billion dollar company and I remember kind of like trying to mentor Shah and being like, “Bro, like, you know, the don’t worry, you’ll figure it out. It’s maybe it’s not this one, but like when you get to your real game, you’re going to be like good because of this experience.” You were friends with him too. Like did you invest in that? Like I never met him. I think Greg actually knows him. Oh, great. So, I don’t entirely know his full background, but he used to do like a bunch of high-tech stuff. He I know that he had the uh what’s the startup that helps you code stuff? It’s like a new age new agency. What’s it called? Starts with a G. Gigster. Gig Gigster. Okay, and before Gigster, Greg, what was he doing? He was doing something like very traditional Silicon Valley, right? I just know him from Twitter, but yes, he was doing uh he was the co-founder and CEO of Gigster, which was which was which was huge. But he did it through a really interesting way. I think he did it through a search lab. Do you guys know what a search lab is? Yeah. And but I think before that, like he maybe was at Zinga or something like like like a like a He played He made like a mafia game or something like that. Yeah, like something No, he made Mafia Wars, right? That’s what it was. He made Mafia Wars. Yeah, okay. Which at which at the time was cutting edge. Now, his latest business, I think it’s called Revolution. Is it called Revolution? Made. Made. Made. Made. And they are renovating bathrooms. And as a recent homeowner who needs a new bathroom, I went to the website and I was like, “This is sick. I love this. I’m in.” And it looks from the outside like the company is just crushing it. Uh I saw another guy, the guy who started Casper, his name’s Luke, uh one of the four founders, his name’s Luke. I think he has a new business that’s also renovating bathrooms or maybe kitchens. And I thought it was interesting that these guys, Casper, not exactly like cutting edge, but kind of, like kind of new behavior, buying a mattress online. Uh Roger Dickey, you know, the definitely new behaviors. They’re going to like these like older businesses and they’re definitely using technology, but at the end of the day, they’re not like re they’re not inventing anything new. They’re just inventing maybe a a a more efficient process. And in my opinion, those things are far more interesting and it’s kind of intriguing to me that they’re these guys are doing that as opposed to some new cutting edge thing. So, so I’ll give you my my take on your on your question, Greg, which is uh in my 20s, it’s like the way I traveled was I’d be like, “Oh, you know, fuck it. I’ll go tomorrow. I’ll spin the globe, put my finger down. All right, I’m going to go backpacking through, you know, Eastern Europe or I’m going to go to Australia and I’ll be, you know, sleeping in a van type of thing.” And I wanted the adventure. It was actually the right move to do at that time because it’s like, how do you get max adventure, max sort of like discomfort and like out of your comfort zone, you know, max spontaneity, all that stuff. And um and then like now it’s like, where is like a sandals resort that I can take my kids and like, you know, I just want to sit down. I just want a place I can go sit. That’s not my house. And like this is like basically the extent of my adventure right now. And so similarly, like that’s my whole my business career was the same. It was like, at the beginning, it was like, “Yo, I’m going to build the next social network. I’m going to build a a dating app where you, you know, you might die or whatever.” This is like these crazy ideas. It’s like every idea was like trying to be crazier