Our buddy sold his app for $200M in just 6 weeks?!

25:54It was insanely fast. And the funny thing is that I went to GDC, which is a game developer conference. And the year before I went and like nobody knew who I was. And it just so happened that it happened at the peak moment of the game. And I went and like everybody knew who I was, but then I could meet with like seriously, like every buyer, like in two days, because everybody was in San Francisco for that conference. And we also got a term sheet for$50 million, which I had folded up and put in my pocket and went to a vent and I dropped it and I couldn't find it. And I only had the printout. So I had a rough idea of what the terms were, but it was on the floor of some party somewhere.

26:33And I came back and I asked kind of like the OGs who had been there for four or five years and there were only seven of us. And we were working above like a combination Taco Bell, Dunkin' Donuts, where the smell was different on which side of the room you were on. And I was like, do you guys want to raise money and like build something really big? Or do you want to sell a company? And they were like, sell the company. And I get it. They had put five years of their life. They were at a pivotal time in their life and it was life changing for them. So I think that was the decision. And I think people asked me a lot of times also, listen, we were really, really good at making games and we made a really popular game and we were good at the community management and the social media around it.

27:14But you take$50 million and you spend a lot of that on building a legal team, building a sales team, building all these commodity things that I didn't think we were necessarily going to be better than anyone else at. So we just wanted to be in a place where we could make games. How did you negotiate the price? They, the buyers came back and they were like 120, 150 million dollars. The board was ecstatic. Well, where'd they come up with that number? Um, I think they were looking at probably we were making a ton of money because, uh, we had so many screens in the game when you go back and forth and back and forth.

27:57So we're trending out of advertising revenue. You're looking at, you know, roughly kind of how much is an MAU or a DAU interesting to you. And so we bring it to the board and the board is ecstatic because we go from being like, oh, should we essentially wind this thing down? And so now we have this thing that's popular and somebody wants to buy it. And so they're like, great, like$120 million. I was like, this thing is worth$250 million. Because like anyone, I'm extremely high on my own supply at that time. And, you know, there's this moment where basically the message they're saying to me is like, you're the CEO, but it's not your company.

28:32It's our company. Like you don't control this thing. And there's kind of a subtle message from me to them being like, well, fine, fucking sell this thing without me because this thing is worth so much money. And that's 50 % complete delusion and arrogance and adrenaline and all the other things that happen. You know, when you're in the desert and you have a couple million users and now you have hundreds of millions of users. And part of me thinking like, maybe I actually am right and like, maybe it is worth more. And so they give me this small window and I go back, bluster, draw something's the greatest thing.

29:07somebody tweets like, you know, Y Combinator pitch, the draw something of X. And, you know, that matters to all of those people. And so I go back and I'm like, I need this and I need that and I need this. And, you know, it's a it's a gamble, but it was right. Like we got way more money and a way better deal because a segment of the buyers really, really needed it because they were, you know, they were telling results. This hit to their stock was bad. You know, somebody like EA was invested in sports games. Somebody like Zynga was overinvested in Farmville. You know, you have strategic imperative to people.

29:50So sure, you're super valuable, but they're all playing a much bigger game. And if you can understand that, that's where your leverage is. And then boom, all of a sudden we do that. I come back, I'm like, the company's sold. and it's, you know, this whole crazy kind of episode. And the funniest thing to me is like, I start reading all of these things, like why draw something succeeded? And then these other articles, why draw something failed? And, you know, when you're an entrepreneur, you read a ton of these and you come back and you're like, did you see these? You tell your team, you see this article?

30:23We need to be doing this. And the reality was, is that every single article was wrong. Like it was completely wrong. like their analysis was wrong. Like there was this whole thing about why we failed, but they were analyzing our iPad app and we didn't have an iPad app. We just had a stretched out mobile app for iPad. And then all of a sudden you just realize, oh shit, I've been reading these articles as an entrepreneur about why things succeeded and failed. I've been making decisions and they were probably wrong there. And now when it's happening to me, they're really fucking wrong. But it was this like crazy ride.

30:57And then all of a sudden, you know, we're part of Zynga and then all of a sudden a year later, I'm not working there. So it was an amazing rise and fall, totally turned around the company, saved us. And we did a whole bunch of things. There were a bunch of employees who I had to let go. And I just made the decision on my own to rehire them like the day before the deal closed, that their options would still vest. There were people who had taken more cash than stock because they had little kids and I got a cash component that I could use at my discretion. And so I just gave them the money that they would have made.

31:35This is this chance to do like all this insanely non-capitalist, but like super cool shit to change people's lives. And after the deal closed, they had a debt-free club where all the employees who had college loans all paid off their college loans. And there's a moment when you have a little bit of money left in your bank account. And that's going to go to the other companies. I ran to the Apple store in Soho. They used to love me and I bought a hundred thousand dollars worth of iPads and all this stuff. And I just gave it out to everybody who worked at the company. And every now and then somebody will text me and they're like, I still have that iPad from 2012.

32:10And so all of a sudden you just do kind of all the cool, fun shit that they would never teach you to do in business school. They'd teach you to do the opposite, but you can do it because you have this superpower, which is not only does somebody want your company, but you have this ability to impact the lives of all these people who've given you their all for the last five years. And to me, that was the coolest part of it. Sam, you know, one of the things I love about Dan is we meet a lot of founders and entrepreneurs and almost all of them. I would actually say 80, 90 % of them will say, it's not about the money.

32:41Money's not the biggest thing for me. I would say most people want that to be true. And then you go look at their actions and it's like, those people are the most transactional. They're the people that want the money the most. And they want to not want the money, but they want the money. And I'm guilty of that too. Dan is one of the few people I met. I believe who plays a game with money. It's not that money doesn't matter to you, but he's told me a bunch of stories of it wasn't about the money. Like he made a decision that was actively not money driven or not even like logical, but he just does it for the fun and for the kicks.

33:14It's like the Joker in Batman, right? Like most people want to be Batman. Dan, I feel like you want to be Joker where you're just like, I just want to see what happens. If I do this, what if I tie up this, this person you love over here and this person who you love me, who are you going to go get? I can't wait to find out. Have you read his LinkedIn? So his LinkedIn is pretty hilarious. So it's, it starts with, I think you were the president of Teach for America. When I, when I think of Teach for America, I think of like kind of hippie-ish, like do good for the world type of vibe. Then you go to gaming, which is in my opinion, the gamers are typically like the hardest core capitalists there are.

33:46It's just like, you're practically working on an Excel sheet on how to change things. But then, so you got this like weird hippie side, but then you're also this capitalist, but then his late day to Sean. So after selling Draw Something, he goes to work for Ari Emanuel at Endeavor, who Sean and I love, we love reading about Ari. Listen to what he says. He goes, I told Ari to pass on five companies for investing that he ignored me and he invested in them anyway. All of them are now out of business. Know what you know, my guy. He's got this like shithead vibe that I love, that I love. And that he's also like does good stuff for America.

34:22And there's also this like greedy capitalist. He's the perfect combination of like a being a holistic balanced human being. I love it. I appreciate those nice words. I will say, I think like none of it is intentional or by design. It's just kind of instinct. And I think I understand what it's like to, you know, be average or not have no money, but not have any spectacular upside and also have that potential in front of you. You know, I have a guy who worked for me at overtime for six years. He left to take another job, which was the next step in his career. And he didn't have enough money to exercise his options.

35:03so that happens all the time and so he just left them so one of my investors is like I want a bigger piece of overtime and I was like you should buy his options like there was no incentive for that he wasn't even working in the company but it was just the right thing to do like the dude worked for us for six years like if I could help him make some money based on that then I think that that part of it was was really cool and I would say like there's two things that really motivated me. One was somebody who once said to me, he was kind of Oprah's manager and helped her be really big. And when I was in my twenties, he once said to me, the most powerful people are the people who know how to give up power.

35:46And not a lot of people say things to me that I either remember or have an impact, but I just always was like, wow, that's so interesting. It is like, Like, it's not hard to be powerful and consolidate power. It's way harder to be powerful and somehow let go of power. And I think there's some aspect you could substitute money or anything else like that. Sure. Like Zynga said, here's$5 million in cash. I could have put that whole thing in my own bank account if I wanted to. And sure. Do I wish I had that money today? Sure. Who doesn't? But like to be able to release that and give it to other people and change their lives is just it's just fucking cool.

36:25And then I would say to me, like, and I told this to staff at the whole time, the number one thing that motivated me was every day I rode the subway and every day people played games on their iPhone. And I was just like, I want to make a game that people play on their iPhone. And I remember there was a point at which the game was so big. It was like, everybody I knew was playing it. It was everywhere. And I was walking my dog with one of my kids in Prospect Park. And there was like this couple and they were like canoodling on a bench and they were laughing and I'm thinking, oh my God, I wonder if they're playing draw something.

36:58I got to go check it out. So I kind of like walk behind the bench and I look over and they're playing it. And I think in that moment, I'm like, cool. But I, of course I can't help myself. I tapped them on the shoulder and I'm like, I made that game. And they were like, looked at me, like I was like a stalker and they were like, oh, cool. And they went back to doing what they were doing. But to me, it's the same thing. It's like I walk to an airport and I see some kid wearing an overtime shirt and I just think like, that's fucking cool. Like I made that. Everyone who I work with, we made that. And like the fact that you can make something that's out in the world that people love, they don't even know you have anything to do with.

37:40I did a whole music festival when I was at Virgin and I remember standing on stage next to Richard Branson and like Roger Daltrey and the Who were screaming and like dads have their kids on their shoulder there's like 80 000 people there and i'm thinking like i was a spark that like made this happen and i'm not interested in these people ever knowing who i am like that's not the point the point is you made something and it existed in the world and it touched people who have no idea who you are and i just can't tell you how fucking existentially cool that is can i ask you a little bit about uh branson and ari so yeah Sean and I have been on this Ari Emanuel kick because he's not probably like us at all in that he's significantly more intense.

38:25Go, go, go. Take over the world. Sean and I care a little bit more about just having our ideal lifestyle. But then you've got Branson. So you said the guy was like, it's more about who can release power. So Branson seems like a guy where it's like decentralized. Ari is like a guy where it's like he's the boss and it's a little bit more dictatorship. This is just an outsider's observation. but what can you say about the difference between the two of them and what attributes each person had that made them kick ass? Yeah. So let me say like Ari is an amazing guy and I learned a ton working for him.

38:58And Richard is also an amazing guy. I would say in Ari's case, when I worked at WME before they bought IMG, before they bought UFC, three months into it, people were like, what is it like to work there? And I was like, it's the greatest fucking Jewish family dinner you've ever been. You just sit around the table and everybody's screaming at each other at the top of their lungs, but they actually love each other. And I had just never worked in an environment like that. Like, Ari is going to walk into somebody's office and he said, listen, you fucking schmuck. You know, what about this or that? And they're like, that's not true.

39:33And I'm like, wait, they're yelling at each other, but they love each other. It was actually wild. And I think that Ari is an example of somebody in a number of ways. One is he's relentlessly curious. He reads, he consumes information. There's nothing he doesn't want to learn about. And I think that that is this incredible spark for him and within the company to clearly like Richard, but in a different way. He has an incredible amount of personal charisma, but he uses his personality to his advantage. And in a way, the person he actually reminded me the most of, who I worked with later, was actually David Stern, the former MBA commissioner.

40:12because like I'd be in a room with David and we'd be talking about basketball and he'd look at me and say, listen, Dan, I get it. You're good at raising money, but are you fucking good at anything else? Because clearly it doesn't seem like you are. And so it's almost like this Catskill comedian style of using humor and your personality that's probably rooted in some like Jewish humor and whatever that says to you, hey, like maybe you should turn left instead of going straight here, but I'm going to say it in a way that that is funny, but you get what I'm saying. And it's going to make you love me in the end too.

40:50And I think that Ari is very, very funny and was very good at that by strength of personality. And also he could call you every single day. That's how he recruited you, right? What's the story of how he recruited you? When he wanted me to work there, he just decided he wanted me to work there and he called me every single day for four months. And what did he say? He would just be like, you know, we have all this IP. We need to do this. We should come here. And then I'd go to talk and I'd realize he wasn't there anymore. And that's the problem with cell phones. Wait, did he did he did he hang up without saying bye?

41:25Yeah, that's awesome. That's what the agents do. They roll calls. He had a list of 300 people. Hey, hey, how you doing, Larry David? Goodbye, whatever. And then he's on to the next one. And they understood it. And I was an idiot. I just wasn't from that environment. So I didn't really understand it. So I'd be talking and I'd look and I'd just see the time on my phone because he'd have hung up and he'd on to the next call. And I just think there's this incredible personal force and momentum that he has. And sometimes I think for some people, they have that, but it can lead to a really toxic work environment and there are all kinds of exposures.

42:01I think he loves life. He enjoys everything. He's very funny. And I think he could have both of those in a way. And he was good at understanding what made you tick and connecting with that. I think Richard is really different. Richard is very laid back, but very cool. And I remember going to this meeting at Virgin Mobile in Canada, and he wanted to talk to all the people in the phone room, the customer support people. And people just don't do that. And he basically just tells them this story about when he lost his virginity, like no pun intended. And it's this very funny story where he humanizes himself and he's just this regular guy and he's not talking to the C-suite.

42:44He's talking to all people who answer the phone and they just leave that thing and they think, fucking love Richard Branson. He is like the man. And it's just charisma. It's just different for each of them. And it's very rooted in what their brand is. Their brand is extremely clear and articulated, but it's clearly they've understood how to make who they are. They're not trying to be anyone they aren't, but they've rooted that. And I think in this world where people become very studied and they read articles and they hire coaches and they do all these other things like that, both Richard and Ari had this superpower in that they just knew exactly who they were and they tapped in who that was.

43:26And that was their brand. And maybe you make some comment about my LinkedIn. It's not like I wake up in the day and I think, I just want to fucking troll everyone who reads my LinkedIn. I just think like, maybe this would be actually funny. And so I think there's some self-realization and it helps to be charismatic and that's really hard to learn and otherwise. But I think in a way they both tap into it and they both are relentless, but not in this grind set way, in this way that like everybody reads on Reddit about how they're supposed to go and grind and grind and be relentless. They just have the zest to do something that matters and something that's bigger.

44:04And where does that come from? That's for the psychiatrist couch. But again, it's authentic and it's unique to them. It's not studied. And I think that's part of what makes it so powerful. The internet community or industry, whatever you want to call it, we need more of that. My father is a small business owner and he does all of his business via phone. And I used to sit in his office and he'd be like, I remember he just like would call someone be like, Hey, sweetheart, look, what's money amongst friends, right? It's just money. We got to make some we got to make something work here. Like just like, yeah, like charm, sweet talk.

44:39I remember hearing this, or just just like little things like, look, it's a little early for you to be busting my balls this morning. We go let's make something, you know, just like this, like gifted gab. Yeah, we don't have that in our industry. It's significantly more formal. It's like, calls are scheduled. I recall is like the default calendar length of the Google calendar, which is 30 minutes. Like, it's just different. And I actually love that type of stuff. It's the in-between stuff that makes those things happen. Look, Ari was an agent, maybe like the most super, super agent of all time.

45:14And he definitely understood that. David understood that. He was not a basketball player. He didn't play basketball in college, Commissioner Stern. And he came into a thing and he's dealing with basketball players and coaches in China and international. And it's just, you know, there's like a human connection. There's humor, there's charisma, there's all those things that kind of fit into it. And I remember, you know, a thing that someone else said to me at some point, this guy, Dick Parsons, who had run a big bank and at some point was the chairman of Time Warner and very, very influential. And he said, listen, whenever I do a deal with somebody, I always just leave a little bit extra on the table because you never know when you're going to come back.

45:57I want to do another deal with them. And like, you know, the internet is filled with, here's how do you extract maximum value from the other person? Here's how you fucking win in negotiation. And the reality is it's like, maybe there is enough to go around and maybe I'm going to let you have a little wins because I care about our relationship and maybe we're going to do business in the future and everything else like that. So I think, you know, per your dad's story and otherwise, there is a bunch of that. And sometimes it makes it easier. You know, they just sent me this thing. They're like, what do you think about all these things we're proposing?

46:32And I just wrote back and I was like, these are seriously mid. And that's like in front of 50 people. So we have this meeting and the guy says to be, listen, my only goal in this meeting is how can we not be so mid? So I'm like, okay, you get my point. And yet I haven't crossed some crazy HR line and you've given it back to me. And so what is the goal? The goal is to actually make something that's slightly better, but it requires, you know, trust and humor. And maybe there is a lost art in Catskills humor and business. And maybe that's going to be my next company after this. How old are you? I'm 58 years old.

47:08So you started Overtime when you were, what, 50 years old? And your partner, did I read your partner was 24? Yeah, when we started, Zach was 22. That's some Leonardo DiCaprio shit. I like it. I would only doubt Dave Fallon is under 25. So you, by the way, the hilarious thing is I saw Overtime and I was like, man, this brand is awesome. Sam, I don't think you're as into kind of like the hoops, mixtape culture. Sam's not about the culture. Yeah, you know, like you are, Sean. Exactly. I've been waiting for somebody to call Sam out. Look, more than you know. More than you know. Come on. It's all good.

47:44So we see Overtime, and Overtime just takes off amongst basically like the young black market in America. It's the coolest brand. It's the shirt everybody's wearing. It's the Instagram page people are following. I'm looking for the founder of this thing. I remember when I first saw it. I'm looking for the founder, and I have an image in my head of what I think the founder of Overtime looks like. What was the image in your head? some guy maybe 28 years old he's got to have some business savvy to him but I figured it was like a 28 year old black guy who used to play basketball or still playing basketball maybe comes from the music scene as some sort of music promoter or record label exec because there was definitely like a culture crossover aspect to this where it was not just prospect rankings or shit like that like not just like a database of athletes or it was not done that way and then I see it's Dan Porter and I meet Dan and Dan actually really helped us out with Milk Road I don't know if I ever told you this, but no, I didn't know that he was.

48:36I don't know how we got connected. He was reading the milk road early on. We asked him, you know, big fan of what you did. Can we just get on the phone for an hour? And Dan's like, you got to do this. And he's like, this is working. And I think the instinct when something is working is to kind of button it up and grow up. And he's like, no, no, no. That's exactly the thing that's great about this is that it's not as buttoned up because I think there was a big Bitcoin conference going on. He's like, you should host the anti-conference. It's like, you know, just PBRs in people's backyard or something like that.

49:02Just like, what's the counter programming you could do against the traditional thing? And I started asking him about the brand that he built with Overtime. And Dan, you told me you studied soccer clubs and bands and cults, and you wanted to figure out what they did differently. And you shared with me two or three things that we used at the Milk Road to help grow that brand. So I definitely learned a lot about brand working for Richard. You know, and he really understood the idea of challenger brand. And I think for me, I was really interested in community, especially coming from gaming. And I was like, what is the challenge around being in the media space and, you know, being tangential, the digital media space?

49:45I'm like, it's all content and views. And it's like, you're looking on your phone or somewhere else. And it's like, that's funny, but it could come from anywhere. And so I was like, you know, maybe what the audience wants is a sense of community, a sense of being part of something, you know, belonging to something. I think that was a clearly a growth hack for religion thousands of years ago. Like let's get a place where people can get together and make them feel part of something. And I think people wanted that. And so to me, it's, it's just like, you start from that standpoint and you just start to observe the world around you.

50:23So you go, you know, you go to a British soccer game and you realize like, They're singing Sweet Caroline. And you're like, what does Neil Diamond have to do with soccer? I never understood that. And it's such a good sing-along song. And then all of a sudden, you're just like, where else can grown men, I guess aside from church, go someplace and sing in the top of their lungs? And why are people fandom? And why do they paint their faces? And I remember I went to a little baby birthday concert at State Farm. and everyone was holding up their phone and I was trying to make a video to put on my story to show that I was valid.

51:00And all of a sudden I realized they were all filming themselves. I was like one of the only people actually filming a concert. Like they were all content creators. They went to a concert as a platform for them to make content about themselves. And I was like, I'm not that way. But like, to me, it was so fascinating. There's some anthropological understanding about, you know, you ask people which way you point your camera and at a certain age, you're, you know, you're filming other people and at a certain age, you're filming themselves. And I just think I've had this relentless curiosity about that.

51:38and to me you can google brand and you can read a lot of shit that has a high ranking in you know in google about how to do this and that but the passion of the soccer team or the passion that you feel for a sports team you think about things like the grateful dead that just gave away their music and let people record it when all that would happen when i was a kid is you'd go to a concert and they'd frisk you to make sure you don't have a recording device on you and how they understood like, well, shit, I could let my fans be the distribution and it could grow 10x bigger than anything else like that.

52:13And then all of a sudden, it's not about your song. It's like, well, I have that song at this show at Nassau Coliseum and I have this show at Hampton and I have this song, this version of that. And so I think in a way, like all of those examples exist out there. And I remember I watched the Travis Scott documentary that's on Netflix. And it's so interesting to me that his audience is so much more passionate about him. They literally cry when they're coming out of the show and he dives into the stage. And you just ask, there are a hundred rappers out there. Why is Travis Scott over here? And they're all the way over there.

52:49Like, why do people literally go? Do people go to a Lil Uzi Vert show and cry? I don't know. Maybe they do, but I don't think in the same way. Well, what's that answer? I spend hours of brain power trying to figure out what that is and reverse engineer it because like, why is this person or this brand so much more beloved than the other? Why is Ari so much more effective in his business than other people are? I think for Travis Scott, it's something about the music, but it is something about the fact that he cares so much more about his fans that he is literally able to jump in the middle and be there with him.

53:25And then when you magnify that, the symbolism around that, the storytelling, I think even for me, it's, listen, I, you know, sure, I'm a guy who is not the same as the people who put on my account, but I'm willing to get in there and answer DMs and talk to them and connect them without music and ask them a hundred questions. I have this like, you know, they always have this thing. They say, if you can give respect, you can get respect. I don't walk into a room and think that anyone will ever respect me or care about me based on who I am unless I am the first one to give respect. And I know that every single person in that room, whether they're a 16-year-old hooper or a talent agent or a YouTuber, has something incredibly deserving of respect.

54:10And my job is to figure out what that is and honor that and learn about that. So over time, Instagram has like, I don't know, 11 million followers, probably billions of views over the years. and it's one thing to say, you know, I learned a lot from Branson or I've watched how other brands work and I've noticed these two or three things. It's like me watching jujitsu versus going in there and rolling with, you know, Hoist Gracie. You've gone there and you've rolled with the Gracies, which means you actually then went and did it with overtime. Can you talk about a couple of the things that you did intentionally that you think helped build more of a cult brand?

54:48So, you know, for example, the hand symbol. Yeah. Tell me, what's the hand signal? Every great gang in the world has a hand sign, you know? And so like, we need a hand sign. And I was like, O, O-T. And they were like, simplify it, make the O, throw up the O. Which is hilarious. Just imagine your CEO sitting in an office and he's just throwing up symbols. He's like, I'm really working on something today, guys. It's going to be big, okay? What do you guys think? Do you think the O should be oval or more circular? and it sounds silly, but I think you even, you told your people, you're like, if you go to this event and you record every video, you got to get them at the end to be like, put up the O and say shout out to overtime.

55:28The same thing. Because I remember, I saw it once, forgettable. Saw it twice, forgettable. Once you see it like 25 times and you got the like cool high school athletes to do it, it was like, now it's a thing. I've had people do it to me at TSA. Actually, when they see my shirt and stuff like that. I think it comes back to just, if you want there to be community and you care about community and that was a premise, you have to give community a way to interact and to share what makes that special with them, right? So I'm a Philadelphia Eagles fan. I live in New York, which is clearly not Philadelphia.

56:09I'm walking down the street and I see somebody in an Eagles baseball hat. I say, go birds. and they're like, go birds. You've given us this common language to say, I don't know who you are. We might have nothing in common, but we got one thing for sure in common. And so being maybe nerdy or cerebral on that thing, I'm like, what are those things that are going to give our community? They're not just going to be like, hey, my good fellow, I enjoy the content on overtime. And he says, thus I do too. Do you prefer TikTok or Snapchat or Instagram? And so instead you give them this little shout out to overtime or this hand sign as a way to say, yeah, we're part of this community.

56:50You know, this kind of, if you know, you know, not unlike the secrets, right? It's like somebody, it's like my father-in-law is always like, I'm going to tell you the secret handshake for our fraternity, but he never gives you the secret handshake. He just like tickles your finger or something like that. Oh, sorry. I can't really tell you. I'm like, you're a hundred years old. Who cares about the secret handshake? Oh, we're word of secrecy, right? And so you have these things, the secret handshake, knock on the door, what's the password? I can't tell you, I can't let you in. And I think you create, you understand in consuming culture and even pop culture, that there are these things that bind people together.

57:29And sometimes you've got to strong arm them into existence. Using the superpower of social media as a customer relations platform, like a CRM as opposed to a publisher, every single DM to overtime and even to me starts out the same. Yo, I don't know why, but that is apparently a very popular thing for people to DM large accounts. Yo, and you go back and they're like, yo, and the next thing is, oh shit, I didn't think overtime responded. I mean, I was talking to this 21 year old kid who works for me and we were talking about going and doing something. He's like, listen, you all understand. Like I was like 15.

58:06I DMed overtime. I just was like, yo, and they DMed me back. And I'm thinking not they, you work here, we, but he's saying they. And so I think just figuring out how to connect with people, how to use those superpowers, what are the things that around religion, around cults, their songs, their hand signs, there's things that you wear. You know, part of the reason that I created this like shirt with the O that, you know, eventually all the talented people who worked for me made way better and bigger was that people used to steal our content all the time. So we'd go and we'd cover somebody and they'd just rip our video and then I'd make a watermark and then they'd zoom the video out of the watermark to crop it.

58:48So I was like, you know, what if we just made a shirt with our O on it? Then we have like a permanent watermark in our thing. And if they rip our video, then that's fine. Then our O is actually everywhere. We've turned our biggest challenge into our biggest opportunity. And so all of a sudden, There were people with shirts with O's everywhere because people were ripping those videos. And, you know, everyone would say, oh, shit, how do I get one of those? Because it must mean you're famous. So the biggest thing we did is for two years, we refused to sell it. Well, you can't buy one of those shirts.

59:17Like you have to be on overtime to have that. And then eventually you create so much pent up demand. And I can't say that was in the deck or the business plan. But as you start to get into a dance and a romance with culture, you start to observe what's happening and you make some kind of audibles around that and you figure that out. But like to be part of culture is to be part of community, to be what's relevant to happening around you. And, you know, listen, we start a basketball league. Every single startup sports league in America has failed pretty much, you know. And by the way, the NBA, the NFL, these are 50, 75 years old.

59:56And you can think about all these startup football leagues that have spent hundreds of millions of dollars. And it's like, why is OTE Overtime Elite, a startup basketball league in its fourth season and every other league has gone out of business? Well, it's because we're focused on the audience. We weren't focused on just playing the sport. It's like, you know what people want? They want more football. They want more basketball. They want more baseball. So it's another league. And it's like, well, they just, they want to know, why should I care about this? Why is this league about me? Who is playing?

1:00:26What are the hopes and the dreams of the people who were playing there. Instead, it's like, well, we got a field and we had a bunch of city-based teams and we said, here, America, you'll like more football. But like, if you can't appeal to the aspects of culture and community and emotion to them, why should they, Karen? And listen, me, I wasn't a gamer and I made a pretty popular game. I didn't know a lot about ticketing and I started the first live event ticketing company. I like sports. I'm not a sports Wizard, I would come in last on a sports quiz show. But it's like I am more like the consumer in that I don't want to get sucked in.

1:01:01So I'm so deep. So it's like, what is resonating? Oh, shit. There's a simple story about that. I'll tell you one side thing that made overtime big. When we started, I was like, here's Sean. He's like 6 '2". He has an eight foot wingspan. He plays for George Washington in high school. He's a point guard. He shoots 50 % for three. and like we'd put the video up there because that's what sports is about. Stats and all those things. Every single time I removed one piece of metadata, it got bigger. Down to the fact that it was like, Sean is fucking dope. Boom! Everyone can love that. Because as soon as you tell me, Sean went to George Washington High School, I'm like, I don't know where that high school is.

1:01:41I don't care anymore. You know, as soon as you tell me he shoots X from three, I'm like, is that good or is that bad? I don't care anymore. So in this weird way, similar to the Draw Something game, the more you can simplify it, the more it's available to everyone. The more you tell me this wine is from this country with this, that, and it's DOC and it's this grape and whatever, I just think like, fuck it, maybe I'm just going to drink tequila. Can you do this stuff with nerdy products or B2B products? Or do you think that it's much harder and only possible for pop culture or consumer products?

1:02:16I think everything has a story at its core. I always think of this dumb example from like a business book that I read 30 years ago where, you know, they used to like do door-to-door selling of vacuum cleaners. And a guy would go around and he would tell the person who answers the door, you know, the suction is so strong and it's got these things. And they sold all the features of the product and he sold 10 vacuum cleaners. And then the next guy comes around and knocks on the door and he just fucking sells you the dream of a clean house. And every time like you find your own salespeople and they're in how many views we have and this is why our product is so great.

1:03:01And I'm always thinking just got to fucking tell them the dream of the clean house. And so in a way there is some abstract simplification of the core of what makes everything great. And the more you know about it, the worse you get and the further away you get at telling that story. So it's like we have this basketball league. We have the number two pick in last week's NBA draft. We have the number eight pick. We have four lottery picks in two years. X number of people watched it on here. You know, all these people are playing professionally. And at the end of the day, like somebody from the NBA is like, why do people care about your basketball league?

1:03:36I'm like, because it's their shit. The NBA, that's your shit. That's old people's shit. This is their shit. And I can never forget that. I can't be distracted by the fact that Alex went number two and Rob went number eight and now they're on these max contracts and they went to OTE and whatever. It's like, if you can keep that fundamental core aspect of why it matters in mind at all time and not get sucked down the vortex, I think that that's the key. All right, let's take a quick break because I got to tell you a story. Let me tell you about the first time I tried to run payroll for my team. I was using a traditional bank and you know the type.

1:04:15It's got a janky interface. It's built like a 2002 tax form and it was open only during business hours. And I hit send and it froze. They flagged the transaction. They locked my account. They put me on hold for 45 minutes and then they told me I got to visit my local branch. And that was the day I started looking for a new banking solution. After asking a few founders what they were using, I found out about Mercury. And so now my payroll is two clicks. I can wire money. I can pay invoices. I can reimburse the team all from one clean dashboard. That's why I use it for all of my companies. And so do 200 ,000 other startup founders.

1:04:45And so if you're looking to level up your banking, head to Mercury.com and apply in minutes. Mercury is a financial technology company, not a bank. Banking services are provided through Choice Financial Group, Column A, and Evolve Bank & Trust members FDIC. It's like nearly impossible the bigger you get not to do that stuff. Sean and I both love UFC. And the reason we like Ari Emanuel is in part because he owns the UFC. And what Dana White has done there, we love because like when Sean Strickland fights, you're like, well, this guy, he's a crazy person who just says wildly offensive stuff. And it's really fun because he's insane.

1:05:16Or this guy's from Brazil and he's really scary looking and he doesn't even speak English and he wears a red paint painting on his face. And it's really intimidating looking. They do such a good job of telling a story, even though they're a massive company now. And they haven't. Well, you know, you know, what's like, I remember I was a fan at the core of the UFC and the core of the UFC was every martial art against each other, right? This guy's a standup guy. This guy's going to take him to the ground. This guy's a college wrestler. This guy's a judo guy. Like that is the easiest fucking story to tell in the world.

1:05:45You could even look at the NBA finals or the Superbowl or whatever. Ultimately we're in these rivalries, this city versus that city, this boxer versus that boxer. But if you could abstract to tell me this is actually a story about passing versus running, or this is a story about something else like that, then you're just like, oh, I want to know how that's going to play out. Like, that's so interesting. I was trying to tell people I went to the Euro League championship with all these kind of young people and Greece was playing Turkey in the semifinals. And they're like, wow, these fans are really passionate.

1:06:20And I was like, yeah, let's talk about the history of two countries, Greece and Turkey. And it's not clear to them, but I'm like, yeah, there's something so elemental at the core of the passion. I think the NBA finals are amazing. I'm not quite sure that Boston and Dallas have existential beef against each other that go back hundreds of years. So you've got to find some other core elemental story in it. Like these guys bought their team and these guys drafted their team. Master, he says your karate is better than my kung fu. If you can stay to that in all those stories, and that's clearly a huge aspect of, I think, what UFC had in the beginning that was so powerful.

1:07:01And I think that's part of Ari's genius is he does understand at its core, like what makes you like Mark Wahlberg when he signs him as an actor? What makes these stories kind of simple in a way? Because as soon as you find yourself having to oversell, you've lost the cause. As soon as you're talking about the third switch on the vacuum cleaner that has seven HEPA air filters, you've lost the whole thing. That's a great story. You're fun as shit to talk to. Like, I could hear stories that you say all day. I'm just trying to figure out how it all works. Can I ask you like a life advice thing? So, you know, if you were my dad, so you did a bunch of things, right?

1:07:43You were a teacher in schools, then you did Teach for America. You worked for these like high powered organizations like Virgin and, you know, Endeavor with Ari Emanuel. You started your own company in the gaming space. You started your own company in the media space. If you meet like a 24 year old, you know, ambitious person who just wants to have an interesting life, want to have a great life, they don't even really know exactly what they want. What's your approach? Like what does Dan think you should be doing in your 20s? You know, what do you think you should be doing in your 30s? How do you, what is like the nutshell of your career advice?

1:08:15First of all, there's a lot of ways you can learn about the world. I learned about the world by being a public school teacher. I learned about the world by, you know, giving guitar lessons. Like there's so many different ways. And I think that, so I have this thing where I just, I really don't like to hire people who went to business school and I'm kind of anti-MBA because to me, if there's a funnel and it starts when you're like five years old and you ask, why is this guy blue? Why do people walk on two legs? That funnel goes through the education system and then it gets to business school and then it narrows and it closes and they're just like, this is the way you do things.

1:08:56And then you've lost all that like pie in the sky, whatever. So I kind of say to young people, like your 20s, it's like the time for you to get fired from a job, the time for you to stay up way too late and go to a club, time for you to like take a Euro pass across England, a time for you, for your friend to say, I'm going to do this crazy thing. And you're like, yes, you know, the time to just say yes and do all those things and ingest and experience as much of the world as possible. A, because all of those experiences come and form you in some way. Like if I didn't go to the concert or I didn't sing at a soccer show or I didn't do any of these other things like that, I don't think I would have ever understood of these, but also because the world is so big and so vast.

1:09:44Like if you haven't, you know, hitchhiked through some other country or stayed in a hammock somewhere or done anything else like that, you just have no context and appreciation for that. And you think your job is to graduate and then to get the job and then to be the analyst and then the associate and then this and then the managing director. And now you're on this pipeline. But you've failed to do all these other things. I have a master's degree in 19th century Mexican history that I did while I was working. My focus was the cast war of the Yucatan. People were like, why are you doing that? How does that help you in your career?

1:10:20And I'm like, it doesn't. It just seemed interesting. And like, if you look on my LinkedIn, I'll say it never had any impact. Nobody ever asked me about it. I never got ahead by having a master's degree. I don't do business in 19th century Mexico. I don't know. You just do shit when you're young because that's the time you do shit. and you just learn about the world and you experience things and you laugh and you cry and you get out there. And like, if you think it's all about this ladder that you get to this other thing, it really isn't. And every single one of those things that you do that has no rationale is really actually about opening a door to something else.

1:10:59That's kind of my advice. You have to go to your rate, your rate my professor profile. Your top tag, your top tag is inspirational. to which I would, to which I agree. You are, you are inspirational, gives good feedback. Just like, uh, what your coworkers, you said, eh, mid, uh, you're inspirational. You love, do you love group projects and get ready to read? Those are your tags for rate my professor. Listen, I like, there is so much from business you can learn from the wire, from breaking bad, you know, all the conference rooms in my last company were named after characters in the wire. I just think I learned stuff from books.

1:11:38I learned stuff from fiction movies. I learned stuff from listening to a song. I'm just like, you know, I remember like the first time one of my kid's friends said, I went to Irving Plaza and I saw this artist, Billie Eilish. And I was like, who is Billie Eilish? And he's like, I would do anything for Billie Eilish. And I was like, whoa. And I look and she has like one Spotify stream. And I'm like, holy shit. Like, what is going on here? and you know what is the thing there whatever she was not marketed she was discovered the audience was the one they were like she is by billy eilish no executive in a high in a you know tower somewhere said you're going to take billy eilish now and so they're all just like if you unpack why things work in the world and you're willing to get out there and experience them then i i think that that's the opportunity the one second piece of advice i would give is that a lot of times you think it's about adapting to your environment.

1:12:36I had a student of mine and she went to work at consulting and she was the only one who didn't get a job offer. You know, you get your whatever offer to come back and she's like, I don't know what's wrong with me. Like I messed up and like, I got to figure out how to change. And they told me I should stop talking so much in meetings or whatever. And I said, you just shouldn't work in consulting. Like you are just you, you are the best version of you. You're just in the wrong situation. And then she goes to this startup and they're like, you can't talk enough. And they love her and she's so happy.

1:13:08And I'm like, you're the fucking exact same exact person. You just got to find the place that celebrates you for who you are. And by the way, you are you and you got to do the best to be the best you can, but you got to put yourself in the best place and you got to think about your inputs. And And, you know, your inputs aren't necessarily like, you know, the things that you think they are. They might be going to the Sri Lankan restaurant in Staten Island and having a life-changing roti and just rethinking everything you ever knew about the world. There's some episodes where in the YouTube comments, people are being like, well, I saw Sean put his chin on his hand and just stare into the screen.

1:13:50or Sam just sat back across his arms and kind of had his mouth open and he was just staring at the guest. These guys have a new man crush. I would say this is one of those episodes where I definitely do. I appreciate you coming on. Thank you for not only this episode, but also helping us when we were doing the Milk Road. It's not even one specific piece of advice you had, but after we talked to you, we were like, we came away with a very strong sense of, okay, cool. We're just going to do this our way. like we don't need to conform this in any way if anything let's double down into all of the like quirks and weirdness and fun versions of what this could become and let's just play that out and see what happens and so that was the the one thing that we took away from from hanging out with you and i hope uh you know other people do that too because i don't think you get that advice i don't think you get that vibe from most people i get that listen i just play the long game if i can be helpful to you and then you're successful and then you buy an NBA team and then it's the playoffs and I want my feet on the hardwood then I'm hoping the days off I got you Dan thank you so much for coming on I appreciate you I appreciate you guys for having me see you soon I feel like I can rule the world I know I could be what I want to I put my all in it like my days off on the road let's travel never looking back

1:15:13All right, this episode is brought to you by Mercury. They are the finance platform of choice for over 200 ,000 companies. Shouldn't be surprised because I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of, and then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive. And you can tell that it's actually made by a startup founder.

1:15:41It's an entrepreneur. You can tell it's made by somebody who used other banking products in the past and didn't like all the different rough edges and annoyances and decided to actually fix it himself. And really, any type of entrepreneur you are, let's say you're an agency, well, one of the things every agency has to do is be able to send invoices, easily create them, send them to customers, and stay current on your balances with all your customers. Well, you can do that inside Mercury. And so I think that Mercury is great. Highly recommend you check it out. And thank you for sponsoring the show.

1:16:06For more information, check out Mercury.com. Mercury is a financial technology company, not a bank. Check show notes for details.