This Week in Startups - E1153: Dave Portnoy on the business of Barstool, talent acquisition, Call Her Daddy controversy & more

Episode Date: December 15, 2020

Check out Barstool: https://barstoolsports.com FOLLOW Dave: https://twitter.com/stoolpresidente FOLLOW Jason: https://linktr.ee/calacanis ...

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Starting point is 00:00:00 This week in startups is brought to you by Masterworks, the first company allowing investors exposure into the blue chip artwork asset class. Twist listeners can skip the 25,000 person wait list by going to Masterworks.io and using promo code Twist, Squarespace. Turn your idea into a new website. Go to Squarespace.com slash twist for a free trial. When you're ready to launch, use offer code Twist to save 10% off your first purchase of a website or domain. And Gusto. Running a startup is hard work, but thankfully, Gusto makes payroll easy. They also offer flexible benefits, onboarding, and so much more.
Starting point is 00:00:50 Twist listeners get three months free at gusto.com slash twist. Hey, everybody, welcome to this week in startups. We've got an incredible guest. You know him as El Presidente. Everybody knows the rules, one slice. Stonks only go up. Dave Portnoy is the founder of Barstool Sports, which he has been building for two decades. It's another overnight success, 20 years in the making a great, great entrepreneur.
Starting point is 00:01:22 And an amazing ability to get attention, Dave. you've been able to just absolutely crush it the last year or two in terms of getting attention for the brand. But I've been watching you over these 20 years. What was the origin story of Barstool? I know it was like a zine or kind of a zine? Yeah, it was a newspaper. It was a newspaper.
Starting point is 00:01:44 So it was like a four page, like, and then slowly to eight, basically gambling rag. It was fantasy sports and things of that nature, black and white. I used to hand it out outside of like subway stations outside of Boston. Austin, we had news racks. So it was a free, a free newspaper is what it started as, a really a gambling rag. And it's really interesting because people now don't know about, you know, the 90s and into the 2000s. When you wanted to be an entrepreneur and you wanted to get the word out, the internet was still pretty nascent. And zines, photocopied magazines were kind of how you started on entrepreneurship. I started Silicon Island Reporter in the 90s. You started this.
Starting point is 00:02:23 The source was kind of like a zine. Paper magazine was a zine. and you actually went and handed these out personally because you didn't have any distribution. Right. Yeah. And we weren't even online. It was purely like a physical publication. So, you know, I was interested in the gambling industry. I flew out to Vegas. I met with casinos, different companies trying to get involved in the industry. And they were all like, well, you've got to be a dealer first. And I didn't want to do that. I had been working a job for four or five years out of a college sales job. So, but they did say at the time, which was like early 2000s, the internet was so cluttered. Like if you went to a gambling website, you'd see fireworks and spam ads.
Starting point is 00:03:04 It looked like you were getting your credit card information stolen. So they actually wanted to move offline into a physical newspaper. So that's why I came up with that concept. Our early advertisers were like party poker. Online poker was just starting then in some offshore like gambling companies. So that was the general. of it. Yeah, and back then there was this massive poker revolution going on. People don't know, but it was basically up until pre-Bahara, the Attorney General of New York, he just shut all the sights down that one Friday, the Black Friday, and all the revenue from that advertising, which was pouring out all over the internet, was gone. Yeah, so I actually flew out to Vegas. Our first advertiser was party poker. It was the year Chris Moneymaker won. That ushered in sort of the revolution. But I was with like the Indian software developers who like made the game.
Starting point is 00:03:58 So yeah, they, I remember it was like a $20,000 like year long contract was our first deal with them. And at some point you start building an online presence and it becomes more like a blog and it gets a lot more attention. Yeah. So it wasn't intentional. You know, I used to hand the newspapers out and people would like it in the Boston area. And I met a guy who used to take the newsreepers. and he was moving from Boston and New York. He's like, I love reading it.
Starting point is 00:04:27 It's not online. If I build you a website, would you use it? I was like, yeah, knock yourself out. If you're going to do it for free. His name was Ian White. He ended up being the CTO for Business Insider down the road. So a smart guy and one of, you know, many breaks along the way that helped. But once he built the website, I was like, oh, I can just type in stuff daily.
Starting point is 00:04:48 Like, and we really kind of became a blog. At the time, if you're like, hey, we're a blog. People are like, what is blogging? Like, no one knew what it was. But that quickly was a way for us to grow faster than the newspaper, which had the physical distribution. And obviously, the more you print, the more costs and you need everything. The website, we could reach people faster, easier, and cheaper than we ever could before.
Starting point is 00:05:11 And the common thread was, you're a gambler. You like to place bets. You like action. What was the first moment in your life? Do you remember your first bet? Were you doing football cheats in high school? Did you, were you throwing shoes against the wall and doing dice in middle school? I remember like betting a dollar on the Patriots like in the 85 Super Bowl versus the Bears.
Starting point is 00:05:32 So at that age, I'm eight years old. I was a huge Patriot fan. They were down like 30 to nothing at halftime. And I actually bet at a half time they come back and win. They ended up losing by like a gazillion. But that I think was the first. Yeah, lost by 50. Yeah, no, they got hammered.
Starting point is 00:05:48 55. That was your first taste of action, eight years old. Yeah, yeah, yeah. And I mean, I always, my dad would take me to horse racing when I was a kid. So I always enjoyed it. Yeah, that's a day at the track is amazing. Like, if you can make a day out of it. Yep.
Starting point is 00:06:04 And I still love it. I love horse racing. I'm still heavily involved in it. Yes. We used to go out to San Anita track. I grew up in Brooklyn, but when I lived in L.A. for a while, we go to San Anita. What a day that is, man. Beautiful track.
Starting point is 00:06:16 You battle all nine, ten races. Yeah. A great day out. But then podcasting video comes out. And your personality starts to really blossom online and you start being like a page view machine. When did that happen when you started realizing audio video was like going to be a key driver? You know, I had become well known and well like entrenched in Boston and like podcasting probably. So we started 2004 around 2010 maybe.
Starting point is 00:06:46 It wasn't even me. It was one of our guys, Kevin Clancy, who had a podcast. and he was talking about, I really didn't know what it was. And I'm like, yeah, do it. I didn't never saw, to be honest, the future in it. He did it. It went well. And then we had part of my take, which was another one of our employees, Dan Katz, did it with PFT commentator.
Starting point is 00:07:07 And that exploded. And then we started saying, you know, oh, there's money to be made here. And we really did more. But I personally haven't done much with podcasts. Our company has. It's a huge podcast company. and we're good at identifying talent. And we have a huge network and it resonates with our demo.
Starting point is 00:07:24 And it resonates across all like skews, you know, caller daddy is like the number one female podcast. Parmite, which we have is number one sports podcast. You have the number one golf podcast, foreplay. So we have a lot. But I personally, in terms of people recognizing me through podcasts, hasn't really been that. Why do you think podcasting became so addicting and so,
Starting point is 00:07:48 why do you think it broke out? I mean, blogs were pretty obvious. It was so cheap to do. You don't have any editors. You can be up to the minute. But what do you think it was about podcasts? I mean, I think it's a lot the same. You know, when I started, it's always like there was a barrier to entry.
Starting point is 00:08:03 Like I remember the local radio stations, they kind of thumb their nose on bloggers. It's like, oh, bloggers in their basement. But it didn't matter how talented you were. You may, if you don't get the right opportunity, you're kind of stuck. There's no way to get your voice out. And, you know, like Bill Simmons is an example of that. He couldn't get a job in Boston. It's like obviously a super talented guy, but if nobody gives you the opportunity, what do you do?
Starting point is 00:08:27 Well, somebody like me or a lot of people, it's like, you know what? No one's going to give me an opportunity. I'm going to create my own. And if I'm talented enough, work hard enough, I'll be able to create an audience. It's really no different than podcasting. It's not expensive. And if you're talented and you have the motivation, you can do it. And if you're really good, you can find audience.
Starting point is 00:08:46 And there seems to be some. real significance to doing it consistently and showing up every day. That is the key, isn't it? Like, if you just don't stop doing it, you build an audience. Yeah, like, you know, the number one thing, which I always, I want to say, bothers me, but everybody who sends me resumes and we get a gazillion of them, as you can imagine, because like kind of a fun looking company on the outside, we cover sports, girls, girls cover guys. So like, if you can't throw a baseball 97 miles per hour, what's the next best thing? like here would seemingly be it. But people sent resumes, I'm perfect.
Starting point is 00:09:21 I want to work here. I'm made out. Give me a chance. Like, yet they've done nothing. It's like you don't need me. It's like, you don't need me. Right. Like, yeah.
Starting point is 00:09:28 It'd be so impressive if the person just did 100 days of blogging and said, hey, I'm a big fan for the last hundred days. I wrote 100 blog posts on the NBA on, you know, movies from the 90s. Here's my resume. Here's my body of work as opposed to a resume. But young people are so dumb. They don't do any work. It's crazy. I don't even look at the resume.
Starting point is 00:09:49 And the people that we've ended up hiring have been much more of the unique ways to get my attention, whether it's creating content. But I've always said the beauty of now, you don't need, like, whatever you're saying you can do with us, you can do without us. You don't need us to do it, do it. So, yeah, they are idiotic in that regard. And we preach it. It's like just sending emails saying you're perfect and you're born for this does nothing. Well, you guys know all about Masterworks. If you don't, it's the first company that allows any type of investor, whether you're
Starting point is 00:10:24 retail or accredited, to gain exposure into the blue chip artwork asset class. I had the founder and CEO Scott Lynn on the program. Back in July, it was episode 1087. Now, I had one question that I wanted to answer during the podcast with Scott Lynn, which was what are the signals that a young artist is going to break out and maybe appreciate? How do you know that? Because that's what I do with startups. Well, here's his answer.
Starting point is 00:10:50 What gallery represents the artist. So mega galleries tend to influence artist's careers in a huge way. We look at what institutions own an individual artist. So the more institutional support an artist has, we like to think the more sustainable that artist market or their artist's career is. Then we also look at who else is collecting that artist. So are major influential collectors buying that artist? And those are the three things.
Starting point is 00:11:16 things that are early signals that help understand where an artist's career could go. What an amazing clip. Bottom line, you can diversify your portfolio by investing in an asset class that is not correlated with the stock market. And there are 25,000 people on the wait list for Masterworks.io. But if you use the promo code twist, TWIST, bump, you get to skip the waitlist. So go ahead and visit Masterworks.com. And use the promo code twist.
Starting point is 00:11:44 There's a bunch of disclaimers you need to read. at massworks.io slash disclaimer. If you want to check out the full episode, search for episode 10087, Scott Lynn, L-Y-N-N-N on This Week in Startups. And you have been exceptional at scouting talent, I guess, and keeping talent as well. That's the hard thing, I guess, if they break out. You had that little kerfuffle with Call Her Daddy.
Starting point is 00:12:10 Two really talented hosts. They obviously are just super authentic and, and just crushing it. And then one of them's boyfriend decides they're going to roll you and they're going to hold a gun to your head. And you broke the backstabbers. And you and you, I mean, this is the greatest story ever. I love this hardcore shit where they tried to roll you. They tried to stab you in the back.
Starting point is 00:12:38 And then you flipped one of them. Tell the story of the call for daddy like literally trying to like. They tried to kill the king. You come for the king. You got to kill him. You can't come in halfway, right? Yeah, that was an interesting thing. And, you know, if they stayed united, it would have been an ugly scene.
Starting point is 00:12:59 And it would have been a he said, she said. And their crowd, which was gigantic, would not have believed anything I said, even though we did have some of the receipts. But it's as you grow a common thing. And I'm sure I'm not the first. I've used the athlete analogy of a player. You know, if you sign a comment. contract with the Red Sox.
Starting point is 00:13:17 You can't just be like, oh, I hit 50 home runs at all start breaking. I'll go play for the Yankees because they'll offer me more. But it's no different. A lot, I feel like what we dealt with, which is they were unknown talent that we found. We paid them more probably than anybody else in the world would have at that time. And they exploded more than I thought, more than they thought. And Quiglin's like, wait a minute, if we weren't with these guys, we could be making a shit ton more.
Starting point is 00:13:40 And they could have. They definitely could have. But that's what we want. For every home run we have, there's 10 that don't. That's how a company like us work. It's very much you always hear like band disputes. Like, you know, someone hits it. It's like now they don't like their label suddenly,
Starting point is 00:13:54 even though they're probably over the moon when they sign that contract. So it is not a new phenomenon. But, and ironically for me, I'm always in a weird spot because I'm negotiating as management, but I'm also kind of talent. So it's like, well, if we're going to pay you that, that puts me actually an strong. position, but I generally go from the management side of it and there, and really the fair. Like what I didn't get in the whole call or daddy, they went from nobody's to they were each going to be multi, multi-millionaires if they just played.
Starting point is 00:14:31 Yeah, make it like a million dollars a year. And then one of them, Sophia, her boyfriend over at HBO is like, you're getting screwed, even though they're getting the bulk of the revenue and they're under contract. And you were willing to up their deal. So you were being completely reasonable. you even gave them a path to owning the IP, which I thought was crazy. I would have never given that.
Starting point is 00:14:51 I would have given like, hey, we'll do a three-way split for the IP if you put in two more years. That's it. Yeah. And again, they kind of held us, they had,
Starting point is 00:15:02 it was an interesting situation because it was COVID and they're big revenue drivers and we're trying to save every penny because it's tight. Advertising is disappearing, no fault of our own, but naturally everybody's feeling it. And we have two people basically holding out.
Starting point is 00:15:18 And we also had a situation, we would have ended up in a protracted lawsuit fine. They were willing to do that. They had people, whether it be, as I call them, Superman from HBO, laundry, scumbags. They just scold for a lot. But they were where they were going. I'm 99.9% positive, willing to incur the cost of the lawsuit.
Starting point is 00:15:41 And again, the bigger thing is, the color daddy audience at the time really didn't know who I was. And if they just split and said, hey, we're getting screwed and told their story, it would have been, like I said, he said, she said. Now, people who know me know over the course of two decades, for better or for worse, I'm pretty honest. But their crowd would have believed them. And still some I see believe Sophia's side of the story, which is insanity.
Starting point is 00:16:06 But you went over the top. You were like super candid. You went to the RSS feed. You said, hey, daddy's here. Yeah, pretty much. And here's, and you've just basically released a pot on their RSS feed, and you're like, hey, listen, I offered them a half-milly a year. This is legit cash. And I offered them a path to owning it.
Starting point is 00:16:24 So dumb. The Call Hard Daddy brand is making millions of dollars a year for you. They try to screw you when they know you're weak. That's really not cool. Like they're supposed to be on your side. You guys are running up the hell and you got friendly fire coming over your head from somebody who you gave the opportunity to. No loyalty. for Sophia.
Starting point is 00:16:43 Zero loyalty. It was infuriating. And then, you know, again, I take things personal. Like, I know it's a very person. You should take it personal. 100%. And then, but from their perspective, which I occasionally try to put, it's like, you know, is call her daddy going to be relevant in two years?
Starting point is 00:17:01 And if Sophia is like, maybe it won't be, they're trying to hit it right now, right when they're hot. Now, it's not right. It's not fair. We were overly fair with them. I think everyone who's heard the story has been like, oh my God, what are these girls doing? Alex realized that as like, this is, we have a great deal. How can we not take it?
Starting point is 00:17:20 And then Sophia refused to. So that, you know, it was an interesting set. So the deals are on the table simultaneously. One person takes it. One person doesn't. That gives you the ability because I'll be totally honest. I don't listen to every episode of it, but I've listened to a couple. It feels like Alex was carrying the show.
Starting point is 00:17:36 I'll be honest. She felt like she was 60, 70% of it. And, you know, Sophia was kind of chiming in. But I thought she was the true talent, but she just took the deal. Yeah. And, I mean, they were definitely a team. The one thing that Sophia has said, it's like, we found them through Alex. Like, I didn't even know if Sophia existed.
Starting point is 00:17:54 And, I mean, Sophia in the beginning was very, like, cool with that. She's like, yeah, I just came along with Alex. That's kind of the Alex's deal. I'm just here because Alex brought me. That's really how it was in the beginning. When it exploded, it became way more of a team. And we, and they became like equal partners. So anything other than that is revisionist history.
Starting point is 00:18:13 The only thing that makes sense on why Sophia didn't take the deal at the time is because her boyfriend at all if they're still dating or what was shopping them around. And it became like kind of mixing business and pleasure type thing. I mean, this is basically tampering, though. They're under contract with you. This guy is going out and trying to get a better deal from one to read, then getting them to back the lawsuit or whatever to try to get them free. This is like NBA players who are like James Hartons, like, I'm going to the
Starting point is 00:18:39 the club. I'm not showing up for practice. Like, you're under contract. It was 100% tampering. And that's why I think it would have gotten really ugly, because I think there would have been a lot of accusations and lies thrown around about what forced them to leave. That would have been wildly untrue. I mean, the other thing that's crazy is they know you're a crazy gambler. You're a principled person. Like, I mean, are they not paying attention to the fact that you would rather have the entire ship burned down than get screwed, right? I mean, that's my perception of you. that is a great question and i always said once this started going down it's like i want to be in
Starting point is 00:19:15 the room with this HBO guy suit man like does i i got the impression that he was the most arrogant human of all time and maybe he thought he was dumb or an idiot and i don't want to say didn't know who he was dealing with necessarily i don't even mean that like i'm some super genius but what you just said you're dealing with a very somebody who i think is very straightforward very honest in business, but it feels he's been fucked over, will be as vindictive and spiteful as anybody. That's just my nature. It's been that I've said I have champagne bottles on my desk with people who I feel have crossed me.
Starting point is 00:19:51 You're also like a Boston guy. Growing up in Brooklyn, like we didn't care who we got in a fight with, but getting in a fight with a group of guys from Boston, I mean, that's just going to be chaos. I mean, these are guys who do not stop. You're right. And that's a fair description. and what you just said, I would much rather the entire ship burn and I drown with it than everybody gets off the ship and survives.
Starting point is 00:20:16 Yes. They can't steal from you. You can't steal the ship. Ship's going down. Yes. 100%. I'm watching this. I'm thinking to myself, if this is a made-up controversy, Dave Portnoy's in an even bigger
Starting point is 00:20:30 genius than I think he is. But I was like, this can't possibly be. It's too fantastic. It's not a put on. right? This only shit just went down is not a PR strategy to create drama. I've heard that about a bunch of stuff, this being whatever, like that way it's a work, it's a WJ. It isn't. We don't do that. You know, a lot of the controversies we end up in, I have no idea that they're going to happen. They're not planned out. But we always seem to be in
Starting point is 00:20:56 the mud somehow one way or the other. And I think a lot of it is I don't mind it. Like I don't get uncomfortable around controversy. I kind of embrace it. And a part of me in Joyce, it like my heart gets going it's like all right this is this is why i'm doing this stuff so um no there was it was as authentic i mean how could not be if sophia's off on her own we have alex so it it the results clearly show it was true yeah and i'm sure like then you came over the top i love that the first episode you do when you bring it back is myly cyrus i mean that was like a super flex dunk i mean yeah we're bringing it back and we're bringing myly cyrus on to talk about hardcore, like, you know, sex stuff.
Starting point is 00:21:37 And she's more than willing to talk about her sex life on the pod. Yeah. And Alex has been great. I mean, the pod is killing it. It's never been more popular. She's never selling more merch. So, you know, she came out smelling like roses. And it's been actually probably better for us.
Starting point is 00:21:55 Does she get ownership of it down the road or you gave her some equity in it? We're splitting it. So, like, if she leaves, which I hopefully we can. renew her contract. She's happy. But if she does go down, we now are partners in it moving forward. That's fantastic. I mean, everybody wins in that. So you raised money
Starting point is 00:22:13 at some point from who churning, right? Like, uh, yeah. And churnin's like a former media guy. He was Rupert Murdox guy. He made a fund. They gave you a low poll offer, but you know, I don't know, 12 million. $12.5 million dollar valuation. Seven and a half million. Then
Starting point is 00:22:31 it went up to 12. They valued that 12. and a half. So this is 2016. Yeah. So, and you at the time have a couple of million in revenue, but you're throwing off a million in cash profits consistently. Yeah, at least. I think it was making a million or two million profit. I mean, we ran a very tight ship. Like, you know, there was nothing extra. There was no extra. In hindsight, like, I wasn't really outside of we built a company. I wasn't a business school guy. I didn't ever really anticipate taking investment. So I didn't know how we get valued, but I didn't care about our revenue. I cared about our profit. So if I went back in time knowing what I know now, I could, I could juice our revenue a lot,
Starting point is 00:23:13 but I just didn't because, you know, I was only concerned about the bottom line. That was my salary, basically. Media is like the hardest business you could ever do. You got somebody to invest in it. And then I think the brilliance of what you've done is not only did you take the opportunity of the blogs, you took the opportunity of podcasting, but you actually saw pretty clearly that wagering, gambling is going to become more normalized in the United States. It's going to become more like Australia or the UK where you go into a bar, you can place a bet. From websites and online stores to marketing tools and analytics, Squarespace is the all-in-one platform for you, yes you, to build a beautiful online presence
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Starting point is 00:24:27 Boom, I told my team, I want it up tonight. We set up the Squarespace, and that was the easiest part of it. It took us longer to write the copy and do the images than it did to set up the website. And so far, remote demo day.com has been a huge hit. We've invested in six of the companies. And you know what a brand you can trust is Squarespace. And I've trusted them for, I think, a decade now. And they've been involved in this podcast for close to a decade, longest running partner of the podcast.
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Starting point is 00:25:13 Let's get back to this amazing episode. When did you realize that that was going to be the path forward? Was that just they came to you and again once? You know, Tern and I think saw that more than I did before I, before I did because that's always and we kind of, he wanted Mike Kearns, who was the guy who was rid of the mastermind behind the original deal, was very gambling focused. I was as much. I knew because it was illegal. Now, when the law changed, the second the law changed, I went to Erica, our CEO, and like, this is it.
Starting point is 00:25:51 This is the moment for us. And we shifted 100% back into it. But I didn't know that law was going to change anytime soon. See, this is the interesting thing. It's an important lesson for, we got a lot of founders who listen to the pod. If you stay alive long enough, opportunities occur that you did not anticipate when you started the company. But if you're just hardworking, you run the business reasonably like you did for profit.
Starting point is 00:26:14 You're not in debt. You control your destiny. Something like podcasting can change your destiny, something like blogs. And then, of course, this, you know, I don't know, Supreme Court said in 2018, you could do wagering what they call PASPO, whatever that act was. Yes. And it is amazing to me that the NBA, the league that was plagued by betting scandals from Michael Jordan potentially having to retire because of that. I don't know if you think that's true or not.
Starting point is 00:26:39 To Donahey, Tim Donahey, the crooked ref who was, he was doing the over under, right? He wasn't fixing, he was fixing not the winner of the game, but it was the over unders. I forget. I just knew him as fixing games. He was fixing games. in games. So they, all of a sudden, Adam Silver's like, we think wagering, in-game wagering is totally cool. Yeah, he was at the forefront of that. And what you said, my dad, you saw he say that, but it's like his, which is, it's not his expression, but if your oars are in the water,
Starting point is 00:27:13 at least you have a chance. What does it mean your oars in the water? Like, if your oars, it's what you just said. Oh, I see you're saying, yes, in terms of the business, right? Yeah, right. Yeah. No matter how bad the storm is, if you got your oars in the water, you got some control of this boat. That's a great line. And you don't know what's coming down the pike. You're there to take advantage, basically. What did your dad do? I'm curious.
Starting point is 00:27:34 My attorney. He was an attorney. What kind of loaded a practice? Corporate? No, he was like, state collection lawyer, basically. I don't know. He worked out of my basement. He wasn't some huge law firm, I'll say that.
Starting point is 00:27:47 Yeah. And now, what's his take on your incredible success now? I know. It took him a while to get accustomed to it, understand it. But, you know, he's proud, obviously. So he's, people know him. He's a character in our world. Yeah.
Starting point is 00:28:03 Maybe not intentionally, but he is. And then he sees you go, like, have this incredible exit that's got to be mind-blowing for him. Yeah. You see you take down nine figures. I mean, that's just, that's a big head. It's stunning. All of it's stunning.
Starting point is 00:28:16 You know, I've been lucky, right person, right place, whatever you may be. But it's been successful, I think, beyond my, beyond my parents, beyond anybody who kind of was there wildest dreams. And the humor, the irreverence, the sort of SNL plus sports coverage or man show plus sports coverage. I don't know how you like to frame it, but I've heard you use the SNL analogy. That is the thing that people don't understand about Barstool that sometimes gets you into hot water is people think it's ESPN when they really should be framing it as,
Starting point is 00:28:49 hey, this is like a comedy central show covering sports. They're just framing you wrong, correct? Yes, so we've always said now for a long time we consider ourselves comedy website, comedy company more than anything. And I think if you look at it under that light, a lot of the things are controversies we've been in would not be controversial at all if you think of it from a comedy perspective. So, yes, there's a lot of examples of that. And they can't cancel you. Well, and I've said that. The thing about Barstool, it's been around for so long.
Starting point is 00:29:22 and yeah I've always told this story but I forget somebody it was either New York Times or Wall Street Journal reporter was doing a story on us and I don't think the guy liked us to be honest he didn't like me but he has a at least he came in not liking me I think he had a perception of what I was and what we were and there's an article or a quote it's like a lot of my friends I consider highly educated liberal Northeast people and I asked do you like Barstool do you like Dave they're like yeah we love it and then he's like how can you like This guy's like, well, we've been reading for 15 years and we know who he is. So, again, a lot of the things are people who criticize us.
Starting point is 00:30:00 I truly believe they really don't know anything about us. They see a quote. They see an article. And if I read some of the stuff that has been written about me, I mean, this guy is Hitler. But there's no context. If you think about cancel culture, like it's so selective that you could take something Howard Stern said or you could take a bit from South Park. You take out the one sentence. You put it out there.
Starting point is 00:30:21 and there's no context, and there is no room in this world for any type of comedy. And if you look at brands that have existed for over 10 years, the Overton windows, it shut so tight now that if you started 17 years ago, the stuff that you did is going to just be completely different than the absolute mental breakdown that people are having online at anybody making a joke that has in any way to do with gender or race or class or education or any of that. I mean, you can't make any jokes anymore. And then it's so weird how South Park is allowed to exist and be completely irreverent. But then something like Barstool makes a joke and we got to try to cancel Dave and shut the company down. Yeah, it's crazy how
Starting point is 00:31:06 that is. I've, another thing, it's like, I feel like sometimes the people don't like me. It's like, they act. It's like if you go to a comedy club, you hear a joke, you run out to the street, you didn't buy a ticket for the show, you don't like the comedian, you're run into the street, you'll be like, you'll never believe what this guy said, but you don't mention that it was in a comedy show or any of it. You just say, look what this guy said. So, yeah, like the South Park example, I don't, for example, a lot of people hate me, love the office, the TV show. Michael Scott, obviously the main character Steve Perel is like, we wouldn't be able to do it now. People would go bananas over it. It is interesting. And I
Starting point is 00:31:43 noticed that a lot, how the people don't like me, but then, you know, like Larry David, I once wrote a blog I'm I'm bringing back the word like I that was a long time ago that I wrote that blog but there's an entire episode of Kirby enthusiasm about that exact it was after that's funny but when I wrote it even though it was meant to be funny it's like oh look at this guy so you know what do you go to it's so weird it's like if you go to London you'll heal the word 50 times you know a night when you're out being said by women men the bartender everybody and we're in this very weird where people are hurt by words and they are, I mean, I don't know how much of this has to do with just Twitter, but you're pretty active on Twitter.
Starting point is 00:32:28 My God, people are just so sensitive to anything you say. You get somehow invited to go interview the president, who also is a bit irreverent. And I think part of the reason he got in office, I don't know if you agree, is people kind of looked at him as like the anti-politically correct. Stop telling us we're idiots. we're going to show you liberals, hey, we can be irreverent and not give a shit. How did you wind up, did like Jared Kushner or Ivanka just text you?
Starting point is 00:32:58 How do you wind up interviewing the president? So I was in Antarctica. It was a Wednesday around probably one o'clock. And a guy who works here is like the president of Trump wants you to come interview him in the Rose Garden tomorrow. And I actually didn't think it was going to happen. I was like, first of all, I was like, what are you talking about? I don't interview people. what are you talking about?
Starting point is 00:33:20 But then a couple of hours went by and they confirmed it like, yeah, they wanted to do it. And, you know, he was obviously trying to get different demos at that time. So next thing, you know, I'm there doing it, even though I've never conducted an interview in my life. And it did a solid job and you got a suit on, you suited up. Yeah. Did you have the suit already in the closet? Or did you have to just make like a run to men's warehouse? Somebody went into my apartment in New York and brought it.
Starting point is 00:33:45 So they met me in D.C. And is he a fan of yours? I mean, he's obviously addicted to Twitter. He must be on Twitter five hours a day and golfing for four. I don't know that he was a fan. A junior is Donald Trump Jr. is definitely a fan. I had talked with him in the past. I don't know that Donald was.
Starting point is 00:34:04 Yeah. I found that incredible. Now, you start trading stocks, sports betting stops. And it's very interesting. I invested in a company Robin Hood, which I just, you know, their idea was to get millennials to invest. And they spend whatever, three or four years working on this, slowly millennials, young people are starting to invest. That was kind of the premise of the entire company.
Starting point is 00:34:29 And someday millennials and will get off their parents' Netflix account, they'll get an apartment, and then they'll want to buy stocks. Sure. We have this crazy pandemic. And then one day I wake up and I see you day trading. And I'm like, oh my God, that's fucking genius. He's actually like talking about his trades. He's saying what his bankroll is, three months. Millie. He's going up and down 500. Then I see on CBC and I'm like, oh, this is so brilliant.
Starting point is 00:34:53 You probably inspired low millions of people, I would say a couple of million people to join Robin Hood and other services. Why did you, what even gave you that inclination that, hey, fuck it, I can't bet on sports. I should just pick some stocks. Yeah. So, I mean, I was, I was, again, I'm a gambler by nature. Sports went away. I thought it would be interesting to try it. What, where? good at is identifying, I think, something that resonates quickly. So I never dreamed it would turn into what it did. But almost like when I used to do pizza reviews starting, it's like, okay, instantly there's something here. Like I can tell it's resonating. I can tell I'm a tracking audience. I can tell people are interested. And then when we do it, we do it full. So it became
Starting point is 00:35:41 an everyday thing. I mean, I got the logo up here. It, there's a lot of that. aspects of Barstool that if you told me this was going to happen like a year ago Dave you're going to become the most talked about guy on Wall Street I'm like what are you talking about like I've never traded this dog in your life I don't know much about it and again we're good at I have or we barstool a sense of okay how do we play this because like the Warren Buffett when I said he was old and you know I'm the new captain now that was a joke on the stream like I was right about So the genesis of that, I decided to go all in on airlines.
Starting point is 00:36:22 And they were getting murdered. And after I did this whole speech about doing it, like 10 minutes later, Warren Buffett is like, I'm out on the airlines. I mean, the timing was impeccable. I said to go all in. He said I'm out. So it was so obvious to see what happened. And the second it happened, airlines skyrocketed. And he looked like an idiot in that regard.
Starting point is 00:36:44 I look smart. But I was just kind of, you know, I had. I know Warren Buffett is a legend of the game, but I rant and rave on these DDT streams, but it's towards our audience, but like Business Insider and all these other publications took the quote. And they're tweeting it out and they're running with it. And that's hilarious. And we're even raw meat in front of me.
Starting point is 00:37:05 It's like, okay, I'm going to start having fun with this. And bang, it just exploded. And people still don't get that you're having fun, that it's, there's some amount of comedy here. I'm watching the thing. I'm becoming addicted to watching you trade because I just thought it's hilarious. And you're like, oh, there's a deer outside my thing. I'm going to buy John Deere.
Starting point is 00:37:25 It's just like, if anybody needed any indication that you're not giving them stock advice, it's that you just bought John Deere because there's a deer outside. You're improving. Literally. I'm criticizing you. Like, you're bad influence. I mean, I'm going flipping coin. Yet there's people you look at these investment people and they're losing their
Starting point is 00:37:46 minds on these shows about me. And what's really probably killing them is I've been 100% right because I've been doing it because I just keep saying stocks go up. Stalks go up. We all know this. We all know this. We have gone up since I've been doing this while they've been sitting on the sidelines saying gloom and doom for since March.
Starting point is 00:38:06 I mean, it's been a long time now. Yeah. It's amazing how tweak they got that you were just saying stocks go up when the entire concept of Wall Street is if you hold stocks long enough, they go up. It's literally the premise of all financial money management. You have some equities and that equities go up 7% every year on average and just don't sell when they're down. And you're having fun with that.
Starting point is 00:38:31 I looked at and said, this is fucking fantastic. Young people who have no financial literacy are going to open up a trading account and they're going to figure out what options are and puts are and just what stocks are. So you're basically doing the financial education that parents didn't do with their kids. A couple million people get on to Robin Hood or whatever app they want to use. 2020 has proven to be a year of many things. And 2021 is the year you are going to switch to a better payroll program. And Gusto is the way to do that.
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Starting point is 00:40:15 Get started today right now by going to gusto.com slash twist. Why didn't you make Barstow finance? I mean, this would be like the, I mean, you have the DDTG brand, but I mean, this feels like a category that you could keep going all into. And there are so many endemic advertisers. And it's never going to end the number of public companies because of SPACs are going through the roof. I mean, this could be like a whole second chapter of the, of the empire here.
Starting point is 00:40:41 Yeah. So it's definitely something that we've given a lot of thought about. And I think we will be involved in in the coming months. You'll have to. I mean, if you just think about the bar stool, you got sports, finance, and sex. Yep. I mean, think about what people like. I mean, the only thing you got to add is like you could add, I mean, vice was kind of drugs.
Starting point is 00:41:02 And then there's food. There's really only two things left that would build out the empire. Yeah. And I mean, I'm heavily involved in food. Oh, you can say drugs. I'm heavily involved in drugs. No, no. I mean, the pizza reviews.
Starting point is 00:41:14 are hilarious. I mean, I think that actually is the number one thing people know me by, to be totally honest. You've done like a thousand of them now or 700 or something? And it's like, oh, you know, I never know who's going to come up to me and say hello and why come up to me. Like, are they like, oh, you're the guy to start Barcelona? Are they Robin Hood guy? Are they a sports guy, patriots? Or are they like, now he gets a TikTok guy. Are they pizza? It's just I never know. Nothing too crazy has happened. I saw the episode where the guy had the truck that was like three times bigger and you were goofing on even breaking his jobs. Oh, yeah, yeah.
Starting point is 00:41:52 Fantastic. But you basically, do you do like five of those in a row? I'm just curious of the mechanics of how you actually get these in. Yeah, it varies. Like, the longer it's going on, the more we will stack multiple in a day because we have to travel so far to find places that I've done everything around me. but it used to be literally one a day, but there was a lot more, but I've done so many in my general vicinity
Starting point is 00:42:18 and I've been in Philly a lot. So if I'm on the road, I stack them. If I'm in the office, like today I did one, there's a new place that opened, so I just did one. But it really varies. And you're dabbling in cheese steaks now.
Starting point is 00:42:32 For Philly, yeah. For Philly. Cheastakes are overrated. They're heavy. They're great, but you can't eat it. Like pizza, I'll never get sick of.
Starting point is 00:42:41 I feel okay. after I have a slice. A cheese steak is heavy. I mean, there's going to be eight hours of pain and suffering after a cheese steak. There's a lot. It takes a lot to be eating. And I,
Starting point is 00:42:54 you know, the cheese steak, people love the food reviews. I know they kill. We're in Philadelphia for the gambling app. It generates a tremendous amount of buzz when I go to popular places. Everyone wants to see it. Everyone likes to talk about their favorite food.
Starting point is 00:43:07 So it makes sense. Another great moment in El Presidente history. you told everybody like the unions can go fuck themselves whatever and all these media companies my friend jib vancoff's company who bought my company weblogs ink the blog company at aOL then he went out and took the engage team and started vox he got unionized and then they had to lay everybody off and the union had no recourse they were just like yeah they didn't even consult with us they just laid everybody off the idea of starting a union in a media company when the media industry is circling the drain and being just hemorrhaging jobs and
Starting point is 00:43:47 their advertising is completely getting screwed and going to Facebook and Google is insane. Yeah. So I got a lot of trouble for that on something that was clearly, and I mean clearly a joke. There was truth to it. But then like the people here who we treat very well, we haven't had layoffs, they were like trying to troll the union people by like sending fake emails to be like, hey, how can you help us? we were all in on it. But that became like a huge story. Like we were getting federal agencies sending us like letters.
Starting point is 00:44:18 And I think the end of this thing was I had to like send an email to the company being like, I was just joking. Like that was the literally you have to explain the joke now. You're right. For real. And of course, you know, there's some politicians tried to use it as a way to garner like publicity for themselves. It's crazy. Basically, my analogy on it, it would be like if, well, they do, but you don't, if you're talented in our business, if I don't pay you what you want, you should theoretically be able to go get a job somewhere else because you're talented you need it. If they won't pay you what you want and I won't pay you what you want, you're probably getting paid what you deserve.
Starting point is 00:45:01 We're not talking about putting, you know, bolts in a car where you can, you know, get a monkey to do it and you can pay the monkey. We're talking about talent business. It's pretty straightforward in how you get paid. It's a free market and you have massive competition as the caller daddy kerfuffle showed. Exactly. I mean, the idea that you're going to unionize a bunch of people who are making a massive amount of money, if they are talented, making hundreds of thousands of dollars years. What is the union going to even do for those people? Right.
Starting point is 00:45:30 Those people have agents. What managers? Exactly. And they do. And what was loss on this, there was never any talk about union. unionizing here. It was like a joke. It actually was because Gawker unionized. I hate dead spin. And it's like they were struggling and going down the drain. And it was like the two things in my head is like the company that nobody's reading and can't get advertising and doesn't have talented people is unionizing when the company that's actually very successful and has talented people and are paying people as talented people. We're not talking about it and we're successful because we're paying the talented people.
Starting point is 00:46:04 So like that dynamic is kind of what I was making fun of. And it's a scary, insane dynamic right now. You have a group of young people who actually believe socialism and being given free stuff is better than having a free market and being able to have unlimited upside. I mean, you feel like you're a Gen Xer to me. I don't know how old you are. Yeah. Yeah. I mean, I'm 43.
Starting point is 00:46:28 But that element always fundamentally, like, I didn't get here by accident. I worked my ass off. I didn't take a vacation day for 10 years, like every day. And there was no guarantee. And I worked, I didn't have any money. Like I literally did nothing forever. I couldn't afford a hamburger. And we pay pretty well.
Starting point is 00:46:51 And now you're going to like tell me how I get to like treat my employees. It was like, what are you talking about? Yeah. There's a very weird. I think a lot of this has to do. I don't know if you agree. But our generation, I don't know if you went. Did you go to college?
Starting point is 00:47:06 I did. Where'd you go? Michigan. Okay. Did you go like horribly into debt? No, I was lucky. I was lucky enough. My parents helped me with the education.
Starting point is 00:47:17 See, I think this next generation, they all thought you go to college, you get a $100,000 a year job. So fuck it. I'll take out $100,000 in loans or $200,000 in loans. Now they got some liberal arts degree. They can't get a job where they get a job for $40,000. And they're like, okay, the system's rigged. Everything needs to be free.
Starting point is 00:47:34 Capitalism is broken. when in fact capitalism has never been more vibrant. Right. And the union thing, and I always said, it's like, I'm not fundamentally opposed to unions. I think there are some industries that 100% need unions. I don't think we're vulnerable. So, you know, I'd have union people getting very mad at me in jobs and industries. Like if you're a fucking coal miner, yeah, you probably need unions and things like that.
Starting point is 00:48:01 And there's some that do. We don't. We're a talent business. The talent rises and gets paid and they hold us hostage of anything. What is the secret you think to finding emerging talent and why you've been so good at? Well, we had a- Is it the nurturing? Is it the identifying, you know? Yeah, it's a combo. We had a big advantage in the beginning because I would hire anybody. I don't care what your degree was. I don't care if you went to college. I didn't care anything.
Starting point is 00:48:27 Like our people did not have, you know, network or comedy backgrounds, but nobody would hire you if you didn't. I would. So I had people that nobody that I'm like, oh, this guy's super funny, but it didn't, no one else would give him a shot. I would. And then I always said when Churning did the deal, I'm like, my goal is that every college graduate who thinks they're very funny, or not even a college graduate, but everyone who used to apply to Saturday Night Live or maybe like in the old days, I'm Toronto. Yeah, what's the, yeah, what was that Harvard magazine? National Lampoon. National Lampoon. Yeah. So now... Mad magazine, that kind of genre. Correct.
Starting point is 00:49:07 Like, now we get the resumes and we do. So we have an immense pool of talent to pick from. And, you know, we're kind of like the first... A lot of times to say we're like the oldest digital media company. Like we started almost 20 years ago. We're just different than the established people. But we're big enough where we have this reputation and we can get... We just have a lot of people who want to work for us.
Starting point is 00:49:32 and we're pretty good at, you know, giving people shots and some work, some don't. And we let people just do what they want. Like, call their daddy, I saw it. I was like, this could work, may not work, here you go, run with it, see what happens. And that's kind of how we work. This is as entrepreneurial company within it as you'll find. Yeah. The secret is based on your being open to new talent and giving them
Starting point is 00:50:02 some amount of freedom to pursue their vision. That's the combination, which means you can make some crummy content. You can make stuff that sucks, right? Yep. But you only need to have one thing become a winner out of 10. And like I'm not, not everything I think is great or bad works or doesn't work. The beauty of what we're in is kind of the internet. Like the results speak for themselves.
Starting point is 00:50:27 We're a big enough platform. We have a big enough hose. and anything new will market. If people like it, it works. It takes off. People give it the chance. And so the market tells us whether it works or not. Pennstock has gone through the roof.
Starting point is 00:50:44 I think it, maybe it's gone five or six X since you guys merged. Is that about right? Yeah. So, I mean, today was a huge day for it. Actually, it was up 9%. So it's at 7885 right now. Oh, my Lord. Yeah, it was at 26 when we did the deal.
Starting point is 00:50:59 then when COVID hit, it went all the way down to five. Oh my God, that's a gut check, huh? So you got 100 million in paper and it goes down 80%. I got it on half. So I did get cash, half, equity, half cash. But yeah, I mean, at first. That's a gut check. Yeah.
Starting point is 00:51:17 It's one of those things. It sucked. But I'm able to compartmentalize it. It's like COVID hit. It's like what, I mean, there's nothing. I get much more frustrated when I feel like I had control or I screwed something up. But the company that just bought me, a casino company, their casinos got shut down.
Starting point is 00:51:36 It's like, what, it threw no fault of anybody. It's a bad deal. Yeah, you got your money and good. Right. And you flopped your stock. And somebody hit up on a runner. Exactly. You take that situation every day.
Starting point is 00:51:49 Exactly. And I can run. That's fine with me. Now, my biggest regret, and I didn't know, the deal was really new. Like when that stock was tanking, Like, I didn't know. It's like, could Penn go out of business? I really had no idea.
Starting point is 00:52:02 And it's not like they're telling me. I wish I bought a ton of stock at five, obviously. I didn't. I think everybody probably does. Well, I mean, here's the thing. When you're so concentrated, it does fuck up your bankroll strategy. Right. I had the same thing with Uber.
Starting point is 00:52:17 I had so much Uber that it became 95% of my net worth. You had so much bar stool becomes 95% of your net worth, I'm assuming, or something like that. Yep. At some point, you got to take some chips off the table and buy a house and, you know, and then talk it or something and not, and be able to sleep. at night, not going through his whipsawes, but concentration is also how you can generate wealth. And, man, watching Uber go down to $15 a share was, I mean, I felt like I was going to puke.
Starting point is 00:52:39 That was, I mean, I think a big question people had when we did and why other companies may not have done the deal, which Penn did, is they didn't know how Wall Street would react to us. I was as confident because, like, generally finance likes Barstool. They're like similar type people, whatever. Of course. But once we did that deal, Wall Street reacted very positively. It went from 26 to 40 quickly. And then COVID hit and everything went, you know, a hell in a handbag. But obviously, it has rebounded and rebounded in a kind of astounding manner so far. What's your best take on? I mean, it's pretty obvious that, I don't know if you saw Biden said today, first hundred days, a million vaccines a day is what, or it's going to be deployed. That's 100 million. 100 million people already have it.
Starting point is 00:53:27 That puts us at 200 out of 300 plus a million Americans are basically going to be there, something like April 1st. This thing's basically getting anybody done. It'd be in the Rivier Mirror. Anybody who dies from will be somebody who didn't get the vaccine where it's incredibly old and incredibly unlucky or something. Yep.
Starting point is 00:53:42 So do you believe in some sort of this permanent reset and the Great Reset or do you believe roaring 20s? Do you think people are going to go fucking crazy Yolo and EDC and Coachella and Burning Man are going to have twice as many. people aren't people going to lose their shit and go crazy or yes go crazy they're already going crazy i mean i've been in miami i go to miami in the weekends um and you know you may not know that covid's even around they're just yolo fuck it no masks i mean there's restrictions so the they're limited capacity but you know i've had covid and i must assume at this point that the antibodies are
Starting point is 00:54:21 still inside of me course yeah like i'm not getting it again and you're in crowds. I mean, you are in crowds there. What was it like? Was it hard COVID or you just wrote it out? No, for me, I believe I've had it twice. I only officially got diagnosed once. I had it in March.
Starting point is 00:54:37 And, well, I thought I did because I'd never been sick in the manner I was, which was gassed. Like, I couldn't get out of bed, sweaty, and I was achy. But I didn't lose sense of smell. I wasn't like stopped up or it's like I can't breathe. And then I got it again in August, same exact symptoms. This time I got tested. and I did have it. But it just felt like almost,
Starting point is 00:54:59 I've never had mono, but I feel like that's how tired you are with mono. And I get wiped out at night, but I was never nervous, so to speak, like, oh, I can't breathe.
Starting point is 00:55:10 Yeah, I mean, when we do the post-mortem on this thing, we're going to see young people got it and got a mass, there were a massive number of cases, small amount of debts, and then just terrible people over 65 die from it. Yeah,
Starting point is 00:55:24 I look at, sports, which they didn't want to do and they're forcing it to do it, but college football, college basketball, NFL, lots of people are getting it. Nobody, you don't hear anybody being like seriously ill because they're
Starting point is 00:55:40 young, healthy people. And for the most part, you can say what if you want. There's rare examples in everything. It doesn't matter if it's the flu. Like, something can, you know, uniquely affect somebody. But if you're young healthy. It's a cold. Like that really seems to be what it is. I believe that. I am firmly
Starting point is 00:56:01 against restaurants being shut down. I think, you know, livelihoods are going to be lost. They're talking about shutting them down for good. I think indoor, not good, but indoor again in New York. It's like, there is no comeback. You have to let small businesses, restaurants control their own fate. And if you are worried about COVID or you're old and immunity impaired, stay inside for the next six months, get the shot. I think it's going to be three months. I got to be honest. I mean, they're doing 40 million shots this month, 50 million next month, $6 million in February.
Starting point is 00:56:33 And we're not going to be in your house if you don't go outside. Yeah, it's impossible. What's the story? You got like a couple of years left. You're obviously deep in this pen gaming stock. So there's a good, they got a good reason to keep you around because you're tied to it. You got a lot of equity. But I assume at some point this deal runs out. Do you thinking about because you're young, you're 43, people tend to do their best work in their late 40s or early 50s. That seems to be when entrepreneurs are dialed in the most.
Starting point is 00:57:03 Do you have another thing you want to do in your life? You want to make movies. You want to retire to Nantuckia. What do you want to do? I'm so focused on Penn. So the Penn deal is going to be about a year in January. I signed a five-year deal. And, you know, I said this on a different podcast, one of ours earlier.
Starting point is 00:57:21 when you pay what I feel is like a good price and you do a partnership with me and you get me. Like I don't have that. You're going to get everything I got full speed. And Penn did that. Penn, we named our price. Penn said yes. And it really is all I think about all the time. I'm so far from, you know, what it'll look like when that contract is done.
Starting point is 00:57:47 I'm just like, how do I basically destroy everybody? That is my mindset right now is just how do I destroy everybody? You're wartime CEO right now. Who's on the shit list right now? I mean, you look at ESPN and say you've got to beat them or I mean, you obviously dominated dead spin. Yeah, they're dead. Dead spins out.
Starting point is 00:58:05 But that's kind of like beating like the JV team. It's not. Yes. It's very clear for the first time in my career, very clear competitors. They're the other gambling companies and there's lots of them, you know, the Fandals, the draft kings. I don't hate them. like I hate a deadspin because they haven't made it personal,
Starting point is 00:58:23 but I hate them as, you know, an athlete hates the Red Sox Yankees. It's like, we have to be. Did they make a run at you? They try to buy you or no? We met with everybody and they both passed. Really? You're using a banker, using Allen & Company or somebody? We were using a banker, Mollis.
Starting point is 00:58:38 Ah. So the banker takes you around and they're just like. With the exception, the banker, the one company they didn't introduce us to was actually Penn. Huh. Yeah. Great. Great job. They are near 3%.
Starting point is 00:58:51 These guys aren't a couple million bucks and you brought the buyer to the table. But those guys just didn't want the Presidente Bowl in the China shop. They just don't know your level of personality the brand? I don't think that was that. What I believe it was
Starting point is 00:59:06 is we work with like Vandal and Drop Kings forever. I know them very well. I know they spent a lot of money with you, right? They did over the years. And maybe the effects started to wane because we were working with like five, six. You brought them as many customers as you could. And we were working with five, six, seven different gambling companies by the end of it.
Starting point is 00:59:25 So it's like our energy wasn't focused how it was. Like once Penn came in, it's like for the first time, everybody in the company was focused. All right, we're now Penn and that's it. It's a very different vibe, a different, different type of like pitch. I'd never endorsed anything like that. So I think they underestimated. what would happen when we had skin in the game, basically. What's your favorite thing to bet on?
Starting point is 00:59:55 Is it sports? Is it blackjack, poker? I love horses and football. Horses in football. And no table games? You go to Vegas, you know? I like table games, but not nearly like the others. Like, I can get up blackjack.
Starting point is 01:00:08 I can take or leave it. I mean, I enjoy it, but nothing like the others. What's the better rush, just running the table and winning a bunch or coming back from being stuck? coming back from being stuck. I see, I 100% agree. And people, this is how I know if somebody's a true degenerate gambler and they love it. Because when you're stuck 50 dimes or 25 dimes and you've got to crawl your way back and you're stuck only two.
Starting point is 01:00:32 Or you're stuck 50 and you get back to stuck five where you're plus two. That's the best feeling in the world. It's better than just running the table being up 50. No different than sports. You remember your loss is a lot more than your wins. It's like losing is harder. Yeah. What's the worst?
Starting point is 01:00:48 beat you ever got. You stared at the ceiling, couldn't sleep, grind your teeth. I mean, how the fuck did I do this? Wow. I'm never going to gamble again. Yeah, I mean, there's two recent. There was the Packers Eagles, the Hail Married end the game, and then they went for two for the Eagles to cover.
Starting point is 01:01:05 And then the Bills Cardinals, the Hail Married end that one. I had the bills, money line. I had the bills everywhere. So, I mean, I lost in two Hail Marys already this year. And what is that like? You're doing 20. 100 grand swings. 100 grand swing.
Starting point is 01:01:21 So that'll keep you up for a night or two. Yeah. As somebody who went through getting a couple of life-changing, you know, deposits in their bank account, have you modulated and given yourself some limits as to gambling? Because your net worth goes up. And then we both know, once you start betting at that level, you can't go back down. Correct. Right.
Starting point is 01:01:42 You got to get the rush. And if the amount money doesn't matter, the rush, you don't get the rush. What's the even pointing to doing it? What are you doing in terms of like bank role management? You got some limits for yourself or do you think you have a chance that you can hit the risk of ruin? Yeah, no, I've always been enough where it's like, okay, I can't, I got to take a break because I won't be comfortable losing anymore. It's more feel, but I've always been okay with that. Right.
Starting point is 01:02:08 Yeah. You can not chase it. Correct. I mean, I chase it and then to the point like, okay, enough. You know what I lost what I can lose. I'm uncomfortable and miserable about it, but it's not going to change my life. On a scale of one to uncut gems, where do you put yourself in degeneracy? I mean, uncut gems would be...
Starting point is 01:02:30 Like a three. A three, okay. So you're nowhere near... No, well, he killed himself. I know. I mean, was this the greatest movie ever? The only thing about it, and we've had their producers or whoever on it, nobody bets a three-team parlay for that amount of money on the tip of a basketball game.
Starting point is 01:02:48 No, of course not. That drove me not for like what supposed to be realistic. Like nobody does that. No, I mean, much simpler if he was just betting, you know, straight. Correct. Yes. But I mean, he played the degeneracy. So I thought Adam Sandler has got two great performances in a career.
Starting point is 01:03:05 That one. And I hate all his other stupid movies when he plays like knuckleheads. But I don't know. You ever see funny people? No, actually, I haven't. You have to see funny people. It's basically him playing himself. is Selma Gomez?
Starting point is 01:03:19 What's that? Is Selma Gomez in that? No. Funny people is like that whole, who's that guy who produces all those movies? Jud Apatow. It's one of those Jed Apatow movies. Yeah, yeah, yeah, yeah. But it is, when he's serious, Adam Seller is funny.
Starting point is 01:03:36 Like in both of these roles, he killed it. Listen. I mean, I like, it was all the movies. I like Happy Madison and I like, what was the other one? Those are the ones I can't pop, but they're just like. Oh, Happy, Madison's funny. I like Happy Madison. It's a classic and I like the
Starting point is 01:03:51 when he goes back to, yeah, he's got to go to the school. He's got to like graduate. Happy Gilmore. Excuse me. Well, it's Happy Madison. Happy Gilmore. And then there's one more that I can't remember. He's a cool cat. Billy Madison. I met our kids were in the same one other than LA. Our daughter or daughters or I don't know his daughter, whatever, we're in the same
Starting point is 01:04:09 gymnastics class. And he just walked over me at one point and he says, hey, I look at them. They're doing good. And I was like, yeah, they're doing great. How you or just like completely normal, cool person. You're a famous now. You got a bunch of upgraded new famous friends, or are you still just with your squad? I'm pretty much still with, eh. I'm still with my squad, but I definitely have been like,
Starting point is 01:04:32 like I said, I was in Miami. I've become friends with, you know. Pit bull? Who? Pit bull, Arod. No, not pit bull. Much more like the nightlife guys. So I went from like having to spend a shit.
Starting point is 01:04:45 a ton of money to get like a table at a club to like just calling up and being a walk in and sit down at a club and not have to pay for it and shit like that that's nice when you don't have to drop 5k on it on a table yes and 5k in miami's getting you like in the coat room so it's very nice oh really that that's not yeah it's crazy how bottle service happened i remember in new york when it tipped over new york it used to be in the 90s you got into places because you were cool limelight palladium tunnel whatever and then i remember marquis and uh Bungal 8 started doing bottle service and you get to the door and they're like, how many bottles do you want? I'm like, well, I don't know.
Starting point is 01:05:20 I drink a glass of champagne. You give me a bottle of champagne. All of a sudden you got 600 bucks. Then it went $6,000 and $6,000 and $6,000. Yeah, it's crazy. That's stuff. I mean, you're not getting out of there for a good table for like $15, $20,000 a night in Miami. Really?
Starting point is 01:05:32 Yeah, really. That is dumb. Is you going to go down there and live there and get out of the New York tax craziness or? No, I can't. I got to work here. I don't know that I would ever want to live in Miami. me if I could live somewhere taxes regardless of just living in Antucket in the summers. That's so great.
Starting point is 01:05:49 Antucket's the best. All right, listen, I appreciate you coming on the pod, continued success. I love watching. I love everything you do. I think it's hilarious. Everybody knows the rule, one slice, one bite. But then you take four bites. That's my favorite part of it.
Starting point is 01:06:01 I just entrepreneur to entrepreneur. It's been great to see, you know, somebody win after being at it for 17 years. Congratulations on that. And keep making great content and breaking people's chops. It's hilarious. Thank you. I appreciate it.

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