The Pomp Podcast - Dave Portnoy GOES OFF On Bitcoin, AI, Socialism & Being Fired From Barstool

Episode Date: June 30, 2026

Dave Portnoy is the founder of Barstool Sports and author of Cancel Me If You Can. In this conversation, we break down how ESPN tried to force him out of his own company and how he engineered the legendary $1 buyback, his days as "Davey Day Trader" during Covid and the GameStop saga, his history with Bitcoin and crypto, and why he's considering running for mayor of New York City.========================Turn every conversation into a searchable business asset with PLAUD NotePro. Visit https://Plaud.ai/pomp and use code POMP for 15% off.========================BitcoinIRA: Save up to 37% in capital gains taxes on your retirement investments. Take 3 minutes to open your account & get connected to a team of IRA specialists that will guide you through every step of the process. Go to lp.bitcoinira.com/after-crypto to win up to $4,000 in rewards.========================Arch Public is an agentic trading platform that automates the buying and selling of your preferred crypto strategies. Sign up today at https://www.archpublic.com and start your automated trading strategy for free. No catch. No hidden fees. Just smarter trading.========================0:00 - Intro0:52 - How ESPN tried to fire Dave from his own company & the $1 buyback12:47 - How Pomp and Dave first met & the Barstool Finance deal14:55 - Davey Day Trader, Covid, & going to war with Wall Street18:33 - GameStop & Steve Cohen23:30 - Barstool's content model & talent machine29:45 - The Business Insider hit piece34:05 - Running for mayor of New York City37:36 - How many houses does Dave have?39:26 - AI and the future of content41:51 - His ex-wife & the bank account story44:12 - Bitcoin — bad trades, losses, & where he stands now47:32 - Crazy Barstool moments54:35 - The new book "Cancel Me If You Can"

I walked out of that meeting, called Rene, my ex. I go, I just got fired from Barstool. I couldn't believe it. And we're changing. It's changing from Barstool Sportsbook to ESPN Bet. And they did this gigantic deal. I think it was 10 years, 2 billion is what this deal ended up being. And ESPN would market everything. I talked to Erica. I talked to Dan. And we all kind of regrouped. What do we want to do here? All right, guys, today we got a conversation with Dave Portnoy. He's founder of Barstool Sports, and he wrote a great book, Cancel Me If You Can. It is absolutely hilarious. In this conversation, we talk about how he almost got fired from Barstool, or he did get fired. We talk about his investments, how much money he's got,

how much money he spends on a monthly basis. Talk about AI, what stocks he likes, what stocks he doesn't like. Bitcoin, is he a fan? Is he not? How much does he hold? There's incredible amount of detail in here, and he does it all in his own style. He just tells you the truth. It's pretty entertaining. Enjoy. Here's my conversation with Dave Portnoy. All right, Dave, you got a new book out. Everyone is worried about all these little anecdotes, but the craziest story to me is that Penn, the company that had bought Barstool, fired you from Barstool Sports. How's that happen?

Yeah, so I thought that would be the number one story in the book. It hasn't been so far, but essentially what happened, and I tell this story, we're in New York, and I had a great relationship with Jay Snowden. Like, we were- The CEO of Penn. Yep, CEO of Penn.

Like, we were lockstep. I trusted him totally. He trusted me. We hadn't met in a bit. He's like, I'm gonna be in New York City. Can you meet me for lunch? Of course, sure. and hand to god walking into the restaurant it's a little italian place no empty i know this looks

like where somebody would get whacked like in a mob movie i literally said it to him to him as we're walking and we sat in the the back table in the corner nobody around and he starts telling me updates like updates in the business he's like we uh are doing a huge deal with espn um which is shocking to me but great i didn't know in my head i'm like all right so is espn going to promote barstool sports book are we like what's going on because you guys were kind of competitive a little bit in terms of you had a sports book and espn wanted to have a sports book and now the company was going to essentially do a deal yeah espn was it was basically a hired gun at that point like they could advertise that they may have been advertising draft kings fanduel whoever they

didn't have a specific company that they're advertising with we were branded so when you think fanduel draft kings we had barstool sports book along those and we hadn't actually promoted the sportsbook in quite a while because we got this new technology overhaul so we had waited i think we skipped an entire football season of doing any promo the thought being um we once the new technology launched we would want to put all our marketing weight in and the market share would go up so don't promote it till we're ready market share lower we promote boom we got the new technology or proning goes up so i thought that was going to be what the meeting was about and he says we did this big deal with ESPN I I was wow that's that's crazy and I asked him some

questions great is McAfee gonna promote it Scott Van Pelt gonna promote he's like yeah they're all in this should be big for us okay great and then he segued to the next point which was like the only caveat to this deal which was a done deal is ESPN said Dave Portnoy can absolutely not be part of barcelona sports or this deal it was stunning i mean i was stunned and he continued what i didn't get up be like oh my god what are you talking about i was taken aback and it takes a lot for me to be taken back but i was stunned and i just kind of sat there i was processing it and he continued and he's like all your stock options and when we did the pen deal we didn't get paid out immediately a lot of it was stock a lot of invested all that was going to vest instantly

How much money was it? Tens of millions. It was tens of millions. So I think maybe close to 30 or 40, if I'm going off memory, would have, I would have had to wait for, I get right away. And I'd be done with Barstow as a way out. And at that time, I certainly was getting a little tired of- How much money do you think you had made from the whole deal before this?

A hundred? I think the whole deal I was making about $100,000, if I recall. Maybe you had made $60,000 or $70,000. Yeah, exactly. So $30,000 or $40,000, though, is very material. Oh, super material, super material. So he explained this all to me, and I'm listening, and he goes through the deal, and I'd be out of the contract, everything's vested, and I just kind of listened to it. The deal was already done.

so we leave the meeting and i did say casually what what if i don't want to be done like what he's like well this is good you get to go on your way but he knew it wasn't like it wasn't like i'm so gung-ho in the company right now i walked out of that meeting called renee my ex i go i just got fired from barstool i couldn't believe it he had set up uh meetings with erica and dan big cat after me and same story here's what we're doing and we're so everything's erica's a ceo barstool dan's our like number one guy and we're changing it's changing from barcelona sportsbook to espn bet and they did this gigantic deal i think it was 10 years 2 billion is what this deal ended up being um and espn would market everything i talked to erica i talked to dan and we all kind of

regrouped and you're like what do we want to do here and they both are like we do not want to become espn employees we don't want to work with espn they wouldn't become employees but for lack a bit of words they kind of would have um also i think we all realize certainly i did most of barcelona would have been fired like no use for them like we have our our bullpen of idiots and people been with us a long time what are they going to do they would have probably cut costs because they have this new media behemoth so came around talked about it and it came to conclusion we weren't going to go along with this. So I called Jay and I'm like, listen, I cannot let ESPN fire me from my own company of 20 years at this point. This isn't going to work. They had already

gone down the path. The ESPN deal was pretty much inked with the understanding I want to be part of it. And I pitched him the concept to make this work for you guys, to go into your new venture with ESPN and to have us be happy and no problems because if we were like, holy cow, we just got fired. This new ESPN deal with Penn is probably dead on arrival. Because you don't have at that time a legal right to block the deal or to block yourself getting fired. No, they don't. It's more of just like the power of Dave and Barstool. These people on the internet pissed at us. It's going to be bad news for our company. Correct. If you're going to ESPN and creating ESPN bet with Penn and you have me in the street saying, hold on, ESPN just fired me from my own company

of 20 years. You're going to go bet with them now? I don't think that would have gone over that great. They don't want to go to war with you. No. And I did have a great relationship with Jay. So I pitched the concept, sell me back Barstool for a dollar. That's where that mythical dollar everyone's- That was your idea? Yeah, that was my idea. Where'd you get it from? uh well we couldn't do it for free because you have to do the transaction but you talked like a lawyer well yeah we had we have lawyers involved to do it but they couldn't just give it to me you have i know but like when you first were like hey i think i'm gonna pitch him on a dollar did

the lawyers over there like that's a great idea or they're like there's no way they're gonna there was no lawyers at that point it was jay and i talking like how do we make this work for everybody involved so it was like i'll inherit all of our expenses and there were expenses and all the payroll and everything. I'll take it over. You got to give me the company back for a buck. And I believe there was till after the Super Bowl, somewhere about six to 12 months, we couldn't compete versus them. Then after that, we could go get a contract. So that was the deal we struck. And it was really to part good ways with us, Penn, let them do the thing i signed a 10-year nda that said i could never discuss the details of this you got fired

that i got fired that was espn because they don't want the blowback even now right saying espn tried to fire dave like what the what i can say anything why are you talking about it now what the beauty of this i'm finishing my book and the pen espn deal falls apart this brand new book cancel me brand new book and i'm writing the last chapter i didn't know how to finish it to be honest i knew it was the perfect ending, but it's like, I can't tell it because they had an, if I tell, if I bash ESPN, they can come after me for everything. So I knew I couldn't do it. Word comes out. The ESPN pen deal is a total disaster. Like we weren't even promoting, we were getting better numbers than ESPN. So the deal falls apart. The very first thing I do, I didn't talk to Jay in forever.

Hey, I just saw this deal fell apart. What do you think about me telling the truth about ESPN? and he gave me the green light so that provided the perfect ending to this book i mean pretty good dude if he lets you buy the company back for a dollar and he lets you tell a story 100 and i always got along with him uh you know and i asked him after it was all over what because we always saw eye to eye i'm like and espn i don't know what went on behind their doors i don't know why they were so i've always i've clearly maybe not clearly but i've had you know headbutts and in disagreements with ESPN. But is it like, are they like a mortal enemy who deserves like a champagne bottle? Or is it more of just like it's healthy competition and all is fair and love and

war? ESPN has been the best thing that's ever happened to the history of Barstool. They've given us two gifts beyond belief. So I don't look at them as that mortal enemy. They canceled Barstool Van Talk and reunited Barstool and put our best talent back together and kind of united. Then they handed me the company back for a dollar. So I don't look at them like that. We have gone to war i guess or exchange words with certain employees of theirs like mina kines works there who i absolutely despise and think she's one of the biggest frauds of all time um but why they single that like who knows if barstool with espn could have been a successful venture it was a interesting thing they did to put almost pen in that corner like we'll do the deal but dave can't

be part of it. It helped us greatly. I asked Jay, I'm like, what made you think, you know, me as good as anybody at this point, what made you think I would let ESPN fire me from my own company? And he, he, it was a fair answer. He's like, I just thought you were done. Like you had been doing content for so long. He was with me through a lot of the worst parts of basically my life and attacks and things. And he stood by me far more than a lot of other companies would of so he i i got where he was coming from like hey let's try espn barstool is two steps forward eight steps back because they get attacked by everybody in this legalized gambling world it's very difficult so i got all that and he just was like i thought you'd be happy to get the money

go buy your place in nantucket and disappear if i the regulators liked you or no hated hated you a couple states you want to go to the deep south in louisiana they may like me massachusetts my home state despised me. There was like a meeting. I used to watch it online, the gambling like council. There was one particular lady who was so biased against us. Another member actually had to literally stand up and be like, I need an objection to be filed that Barstool is being treated differently than all the other companies we've interviewed because they would go read old articles about me that aren't facts, but treat them as facts. So it was, I think I say in the book. We had a very early discussion when Penn bought us. Do we name the gambling app Barstool

Sportsbook or come up with a new name? And it was a discussion, a round table. And I argued we keep it. I'm like, we have so much equity in the name. I think it's important. Hindsight probably would have been better off going a different name and pushing people to it because people have so many opinions about us. And that's fine. In my world now, I don't care. You say whatever you want about me. And if I want to come back at you, I will. Can't do that when you're regulated by the government. And that was part of the deal I made with them when we did the deal. It's like, I won't attack government officials. I won't talk on politics as much as I can because we have to deal with these people. And guess what? One state may be very red where you need a license. The next

may be very blue. So you can't win unless you just keep your mouth shut. I think a lot of people try to figure out how did you build this thing, right? And so I can only talk from my personal experience interacting with you. The first time I think you and I ever met was during COVID. You were doing unboxings you're a day-to-day trader you know all this stuff you you cost me a lot of time getting ready to i had you made me have to accept bitcoin for the barstool fund before that before that uh you just randomly dm'd me and said i'll come on your podcast why i would love to know because i didn't ask you there had to be something that somebody tweeted at you i think but you you said yeah so i was like okay fine you know you were uh that was like your uh hall of fame years

I think of content creation was during COVID. So we do it. And then afterward, I think we both had fun. And then you were like, Hey, uh, let's try to figure something out. And so you, Erica, et cetera, we all started talking about stuff and there's two defining moments that I remember. The first is, uh, I was sitting in the office, uh, with Erica and we were talking and you came in, you had about maybe twice as big of a iced coffee that you were drinking and you were pacing back and forth and we were talking about doing barstool finance and partnership all right and one of the things we kept talking about was should we invent some kind of game or sport and i remember talking about like should we do heads up trading what all stuff you're just pacing back and forth and all

of a sudden you just start muttering i don't know to us or to yourself they never saw me coming they never saw me what was i talking about wall street because i look at you and i say and i say dave Three days ago, you're on TV. You had a cigar in your mouth saying you're the king of Wall Street. And yesterday you were pulling Scrabble letters out of a bag saying, you know, this is so easy. I'm better than Warren Buffett. And Erica and I both were like, this is electric content. Like there's no way to beat this. And of course, Wall Street doesn't know how to compete with, you know what I mean? Like, like CNBC can't do this, none of this stuff. And so I don't think any of that was planned. Like, I think the Scrabble bag, you probably just grabbed and was like, this will be funny. And then it turns into a thing. is that like how most of the content got created all of the content i mean there we we we do we have a lot of people a lot of talented people myself included you try different things you see what resonates but yeah uh like ddtg was massive when it was going and clearly that was never something i thought that was uh early days of covet it was we just did the deal with pen it's supposed to be sports gambling we signed the deal the ink's not even dry one of the all-time

most this barstool stories ever is when we rang the bell on nasdaq it was the worst day in the history of nasdaq like we're pumping champagne and the entire board behind you is just bright red like the country is ending the world is ending no one knows what's going on like clinking champagne bottles um to celebrate the sale but that was that's how recent like the deal was signed covid sports go away good thing you got assigned really and i didn't know if they were going to business. Their stock went down to like three or $2. And I wasn't that close with Jay yet. We just did the deal. So I didn't know what was going on, but I knew we were supposed to promote sports gambling. That's why they bought us gone. So it was like, all right, well, the stock market's

still going. And I decided to do that a day. We had Glenny balls, big fat Glenny. And I'm like, first day, I'm like, Glenny, give me a stock. It was around 1145. He goes, people get hungry at lunch, Shake Shack. So I bought Shake Shack and we just started watching the stock market and people were riveted. And I was all through COVID. I mean, to be honest, people do eat lunch. They do eat lunch. They do eat lunch. And I think he bought that stock around like 30. And at one point it was like triple. So I went live every morning, the stock market opening bell, closing bell for about 15 20 minutes putting millions like into it day trading it in it it took off and wall street at first i think hey it's funny this queue we're gonna have fun with them and then

i think they started not liking me as much and everything but i still like think wall street is just an insider's game and and the biggest casino and the people try to like you know the gate keep it basically my take on it was they didn't like that you were saying the truth in such a like crude transparent way because you were like stocks always go up yes right and they were like oh you're not supposed to say that right you're like no no literally just look at the look at the history of the stock market it just keeps going up like you guys are not smart and the stock market they had never dealt with an internet guy so you know i'm saying i'm the new captain of the internet and warren buffett's old and and like would you trust like

an 80 year old guy to run any business. Why are you listening to him? And there was also one of those moments, those peak moments where I was like, I don't think airlines or cruises are going out of business. So Spirit Airline, which is now out of business, was trading down to like six bucks. I'm like, I'm going all in on Spirit Airlines. Big whoop-dee-doo. We fly in this country no less than 10 minutes later. Warren Buffett's like, I'm selling all my stock in the Airlines. So I posed it, me versus Buffett, and Spirit Airlines actually ripped. It went from like six to 21 in that span. So I'm like, you follow this idiot. Now I'm putting on a show. It's- But you were right though.

I was, in that case, I was totally right. But I'm still, I'm talking in Barstool language. Well, when you see Dave Portnoy, he says he's the new captain of the stock market, Warren Buffett's old and washed up. In the Wall Street Journal, it hits a little different, but that's what was I was spoofed on Billions. They, like, they had a guy sitting at a desk, whacking. So that was a whole new audience that was introduced. But I think a lot of people also started to realize, like, you were essentially a mirror

to what was really happening in the market. Like, there was tons of young people coming in, robbers, all this stuff, right? So, like, in a weird way, maybe you were just, like, an older version of what was actually happening, but you were the one who was communicating it as directly as possible to the people on the internet.

Yeah, and then the GameStop thing happened, happened and i was dead smack in the middle of it because i'm day trading and like didn't you bully steve cohen off the internet yes steve cohen deleted uh his that story because so i know i actually know the other side of that story yeah so the game stop thing happens and i'm trying to ride it like everybody else i was maybe a day or two late but i'm like oh my god the wall street bets things going bananas roaring kitty had posted a video about me like before this happened he's like, people are making fun of Davey Day Trader. He's going to the moon, like before Roaring Kitty was Roaring Kitty. So I was in the middle of it. And then all of a sudden, you can't buy it. You

can only sell it. And the thing craters. I think I lost 70 grand on it. I'm like, what is going on? As was everybody else, mostly novices. And a lot of people actually who didn't trade stocks, who had heard about it, friends who signed up for accounts and put money into this thing to be totally screwed, like totally screwed. Vlad Tanoff, his first interview was with me. I had on DDTG and I'm grilling him. He's trying to be like hipster. He's wearing a Lakers hat. I didn't know half the stuff I was talking about because I wasn't overly fluent. And Steve Cohen, it went through. So the way I remember it is it appeared to me that Citadel, Steve Cohen were trying to bail out all the hedge funds,

the people who are shorting it. So I was hammering Steve Cohen, who doesn't have the best Wall Street reputation. I'm like, did you guys do the inside trade? Are you getting the information from Robin Hood? Are you involved in this? He had just gotten on Twitter. Yeah, because he bought the Mets.

Because he bought the Mets. So he got on it. So the side of the story I know is that he basically was like, I'm going to talk to the fans. And when this is all going on, he has a bunch of people around him who are like, hey let us help you let us review the tweets you know like kind of doing the thing that you're there to like mitigate risk yep number one is don't let the billionaire tweet directly

to the people yeah right yeah and supposedly he was like nah i got it and he just told everyone like leave it alone and then he did not i think realize who he was engaging with yeah he he came and went quick and and who i i've gone back and forth like i i've never met him i've heard stories like he's somebody if you want to put down a list of people you don't want to cross he's generally high on that list so i don't know if that has complicated things down the road but yeah he deleted it quick like so he deleted the entire account yeah gone and what'd you do when that happened i said i ran him off i ran him off twitter he's come back but and i still ask every once in a while i mean they the movie dumb money which was about that whole thing i still don't

know how because we get threats like takedown requests all this the movie dumb money used a clip of me in the movie without asking me which i still don't know how they had the clip of me talking to vlad tenoff except instead of vlad they put in the actor who played but i was still real and it was still the real conversation no one no one told me it's like oh i'm in the movie do you want a royalty check no my ego is fine with being in the movie and maybe they knew that like trust me this guy's just gonna be happy as mentioned but yeah so it was like every somehow a trait of mine and ability of mine is not on purpose we're pretty good at ending up smack dab in the middle of big things like how in the world was i in the middle of the game stop controversy but i was

there and i but it's also on the internet and i think that there is something about like having your finger on the pulse of what's happening and and i think being able to communicate what you're thinking one of your greatest skills is just like you just say what you think yeah right and so you're like hey what are all these people over here doing it's kind of like you're walking down the sidewalk you see a big group gathering and you're just nosy right you're just like hey what's exactly what's this group and for the for the for the finance they just had never there hadn't been an innovation in how people talk about finance probably till mad money like and mad money had been around forever there weren't people making hype videos like i was

making a green dildo or whatever the green i had a green hammer i mean i was going after these these like hedge the people on tv i mean i was crucifying them and they didn't know how to react and by the way if you react you probably lost because i have a team of like ninjas making these hype videos for me. So it was, uh, it was something. Yeah. I mean, it was pretty entertaining at minimum, right? All right. Um, so the second interaction, uh, or part of this interaction is we started talking about, Hey, should we go do this deal or whatever? And, uh, I never really thought that this was like a, a big deal or anything that was noteworthy, but I heard big cat on a podcast say that I was one of the only people to ever go through, Hey, should we do

something together and walk away? And he was very, uh, shocked because the deal that you had offered at the time was let's do barstool finance and we'd be 50 50 partners on it and the part that i got hung up on was i was to take all of the assets and contribute them to it and you guys would bring the barstool machine and what i come out of is you got to buy it right and so we just were like hey look we like each other we think this could be pretty powerful whatever but i'm like hey look you guys got to buy it you guys like now you just contribute it and the reason why that was so interesting to me was i think i got an insight into how you guys worked with so many these creators right most of them aren't business oriented they don't selling their instagram

account or whatever it's like not a thing but then you look at your track record and the ability to supercharge these people whether it's the you know call her daddies or whatever like i don't know if there's anybody who's got a bigger hits business than you guys have had over the last 15 years or so taking people who nobody knows and making them huge stars right yeah i i've said that uh i think i would put our roster of digital media new age media stars up against any network really um you know if you include me but me big cat pft and then you look i mean busting with the boys spitting chiclets uh call her daddy call her daddy jenna marbles even kfc on instagram one minute you know man also yeah yeah it that is that is the model what you just described

I mean, that is how we do the model with a lot of the people it's, uh, now I don't know if we had to like a term on yours. Like the, the talent is generally, well, you do two or three is very similar to an athlete in a way. You basically sign them and then there's some sort of like revenue share component to it, right? Yeah. It depends how big they are when they come into our world on what that is.

Now you've started to, uh, eat into more. So now you guys, you know, you've gotten into alcohol, you do the events, you sign the big deal with Fox, do, you know, the Saturday football stuff. Like it almost feels like you guys as a business have graduated. Are you still looking for some of like the undiscovered talent and that's still part of the model? Or do you feel like you've reached a point now where we always are? It's,

it's far more difficult to find that talent now because they don't need us as much. It really, you're evaluating two things. Hey, we can, as you said, supercharge your career.

If you're talented, you can basically cut the line. You can grow really fast, but in this day and age of you know streaming and twitch and instagram and snapchat and and tiktok you can build a pretty big brand without being attached to a network it's a lot easier so you that that's what people who try to hire half the way um we're always looking but it's we're not going like it's not the number one priority if we find them great we will hire them, but we're not out there scouring. Yeah. Ladies and gentlemen, I'm a software guy,

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in capital gains taxes. And it's just going to take you a few minutes to open an account. Their IRA specialist will walk you through the entire process. But if you want to enter into a potential winning of a one hour Q&A with me, plus up to $4,000 in rewards from Bitcoin IRA, you're going to go to lp.bitcoinira.com slash after crypto. So again, go in the description, click on the link there, download that free guide, you're going to enter to win. You can learn more there. Go to lp.bitcoinira.com slash after crypto. out. I think one of the aspects is like, you guys have always been edgy, right? And so you have this line in the book that's like, you don't cancel me. I cancel you. And you look at, you know,

Penn deal, right? You look at Steve Cohen. I mean, we can just go through all these examples. There's some people who are really attracted to that and they want to come and work with you guys, et cetera. And there's a lot of people who are just like, these guys are fucking crazy. I don't want to be associated with them, whatever. A huge reason is because the media came after you. How bad was that? Like, I know that people look at you and they're like, oh, he punches back. and there's a lot of folks who i think are inspired by that or whatever but like i've had people come after me i've had you know death threats all this it's not fun i can't imagine that you were in a good spot the business insider stuff was the lowest i've been uh probably in the

barstool 20 something years like you felt like you were under attack yeah it's not only under attack i i knew there are lies and i knew what they were going to write and you know the day before the article comes out like i call my parents to be like just heads up this is gonna be written about me tomorrow and everyone's gonna be talking about it that's a horrible thing to do my girlfriend at the time ex-girlfriend i hadn't met her parents yet they're saying really i mean if we're just being blunt they got away with saying they didn't accuse me of rape and in the article it's like there isn't but the headline's right like they said it's basically reads as rape um totally made up it was to me it was very depressing it was very scary that that can be done on that level

and i you know i fought that tooth and nail i tried to sue didn't get anywhere with that uh and even that will be misconstrued dave lost the lawsuits like i couldn't prove malice like because they didn't they didn't say i was in jail when i wasn't but if i could ever get like the emails on how this happened and where it came from there's no amount of money i wouldn't pay for that because i know it was a hit piece i don't know where it came from so yeah that uh that was a bad time i don't care about a lot of the other stuff like i it's so but that's the one that bothered that's the one and still did you think about giving up at any point just being like i'm just gonna go away no but i mean i still live with it every day like you know we were just talking a

little bit about politics before we started and and people don't like me like they'll quote that article like it's real and be like oh you're gonna listen to this guy and there's nothing i can ever do to change it but that's that'll be with me forever on totally false and when i say false i always make it clear i'm not talking like oh there's 0.11 chance there's zero it's just a made up article um so that that was low you i think you are the uh i don't know if you call uh the wall street communications strategy innovation i know you call it that i don't know if that's really innovation but i do think the innovation was like oh you're a journalist well why don't we just sit down have a conversation and we'll just roll the cameras no editing and we'll just

see what happens which i'd never heard anyone say that to a reporter before that was the funniest shit of all time and they won't do it like which is which is always my points like the business insider and then the new york times each spent a year plus in my life and didn't want to sit down with the subject they were interviewing and by the way they never talked to my ex-wife who was married to for five years dated for five never talked to erica and ardini never talked to any of our female employees they were just calling every people would send me uh audio recordings of the reporter and they were crazy that it's like they're so digging so yes i've always said even this book tour people would come up and and i'd be like yeah i'll do it but uh i'm recording

it the wall street journal literally came over and and he he said i i hadn't read your book and i heard all your requests to do this interview and i was very confused why you were like i have to record it and then he's like i read your book i understand now why you want to record it and i learned that early on i learned that uh from inside edition and a clip that will still this is when i was young naive dumb i thought they were going to do a fair interview it was a hit piece and it was all it was two hours chopped into 45 seconds of making me look like hitler and i'm like okay i'm gonna have to be a little more careful because i am i was naive at that point well you come from the internet you come from newspapers right and then all of a sudden

it's like hey these people have an agenda and they've got distribution in a game where you don't have a megaphone back like you can't reach the tv audience without going through correct right and i grew up in a household like my dad new york times gospel like cnn gospel that's that's the household i grew up in and it's kind of what i just thought i like i never till i got into barcel really thought about oh the the times is left or the washington post is left that never crossed my mind really i i didn't pay that much attention uh you mentioned politics uh you're all over the news right now because you said that you may run for mayor of new york city why not just run for president i mean it really the the new york city thing is because i'm specifically it's

not i guess only here but i am overly disgusted with what is going on with who's being elected from mandami down to these primaries and the things they've said they've let the fox into the hen house and i am as i'm sure you are but i'm an entrepreneur i'm a capitalist i'm not saying this country is perfect but i do love this country and they're openly like saying they hate the country and they want over i mean it doesn't even sound real when you're like well she found a group that wanted to overthrow westerner society and that she said like state the stated uh yeah mission of the group correct and it's like that we're electing her like and mandami's got her hand in the air and they're doing a pub crawl so that's that's shocking to me that's really uh that's why

i said new york city because you know he he is doing what he said he wanted to do before he got elected which is get as many socialists elected and then basically seize the means of communication And they truly seem like they don't like this country and they want a major change. So that's when, you know, I get asked, I go back and forth on it. I like, could I went in New York? Probably not. A lot of people being like, you're going to win in New York because the demographics stronghold. Yeah. Yeah. I think it'd be really hard and outsider, but who knows?

Would you run as a Republican or an independent? Probably independent, but I'll tell you what I would do, which would be a little shift from Mandami. he's got these idiotic politicians who don't know what the internet is and he uses it like a weapon he's never gone up against somebody who can be like not so fast like you think you're good at the internet i'm pretty good at the internet myself so it would be a very different type of opponent for him than what he's used to it's almost like he's treating like how i was treating wall street they don't know what to do when he's making these cutesy videos yeah he's got kind of

like a mr rogers neighborhood vibe yeah in the videos by the way he's an excellent communicator he's doing it very good he's very savvy um and he knows how to use the internet and social media and appeal these people and the people he's campaigning against have absolutely no answers and no idea how to combat that i i may not win but you can run for some internet stuff i'll do some internet stuff i think that uh your meme warfare would be very good compared to like mr rogers neighborhoods totally and i'm sure i could raise an absolute war chest because there's a lot of people who do not like this guy so uh yeah i mean you asked in the beginning off camera like is it real it is real do i think it's going to happen no but there's a lot of times i feel

like my dad on the other side i i can't get out of this space like it's social media it's the tv and i really am like what is going on in this country specifically starting in new york i feel like mandami is the head of the snake um so that's why i said new york and then other days i'm like dave you have a great life you're in isle mirada half the year in the keys and then talk it you've made it why like why do you want this i mean i said that about trump like what made trump want to be president seem to have a pretty good life and there's no dirtier game than politics 100 percent how many houses you have great question uh i have five five houses one's got mold and it being fixed so it's pretty crazy to go from the newspapers to you had to think for a second

how many houses you have yes yeah i yeah listen in barstool has been that that's what the book really did it's like you look back and it's like how did we do this i don't even know could it ever be done again in the probably not the right time right place um i never dreamed we'd become this successful it's been a wild wild ride how much money do you think you spend in a month i have no clue i mean i'm actually not an overly i like horses yeah uh and i bet on sports but i'm not like flashier going out so like i i my take on you is like you don't really party and do all like the crazy things where like most people blow a bunch of money but you know horses and houses like those are expensive yeah yeah those are but the houses are an investment so it's like if the

house listen i don't think you can go wrong where i'm getting the houses and and if this the money is sitting in a stock market or sitting in real estate to me that that's did you buy any of the houses sight unseen or did you visit each one of them i visited each one of them and i had the same feeling so nantucket's my favorite place in the world dream place going had the absolute like best feeling when i walked through the door that was the same with my isle mirada house you just knew just knew and then saratoga i bought a tear down and rebuilt it near the track so those are the three that i'm really in all right um in the content game one of the things that i hear people talking about but i haven't really seen anyone do yet is all this ai content you worry

about that at all with barstool in what sense like if somebody shows up and it's like hey we don't even need the talent anymore forget like i think you called it you know your your circus of idiots and we can just like remove all the cost of this and we're just going to use computers yeah well that luckily for the morons who work for me i i wouldn't do that but i could i could replace 90 of my staff with ai i did my audiobook and i couldn't read like i can't read i actually think i do have dyslexia a little bit like i hated it so i spent 10 grand to have this very advanced ai read it you could not tell the difference i couldn't tell the difference my parents couldn't tell the difference they won't let me do it the book company's like can't do it like so you had

read it yeah so i had to read it but the ai was so good it was scary like nobody would ever know it was me it was picking up everything so of course ai could replace these fools i have although we have had a couple employees try to use ai and it almost makes them too intelligent where we're like that's not you because it's too good so but it is it is a tool that if i wasn't working for us like if we sold or i was out and it was espn and pen 100 that would be a concern do you use any other ai tools like on a daily basis no none i mean well i use like chat yeah yeah we gotta get you on sylvia you you seen that yet no we built this product you uh go in and you attach all your accounts like your financial accounts you just talk to it about your finances

oh so if you were like uh you know hey should i buy the horse or not yeah it has all i don't want to disparage one of your products since it's yours but that sounds like one of those horror movies where the robot takes over your finances and you go and log in no i'm out of money it can't touch the money you can't touch the money well maybe it'd be too smart right it is like eventually it eventually one day there's a like one of these and there's been a lot of movies where the robots become too intelligent like of course turn around kill the humans yeah that's gonna happen with ai and we're gonna be like we who couldn't have seen this coming i mean it's becoming that smart Do you worry about that?

No, I'm not a conspirator. But, I mean, it's crazy what it can do. Yeah. Cfosylvia.com. You should check it out. Your ex-wife, you said that she was the first person you called when they tried to fire you from Barstool. I also saw a clip that she still has access to your bank account. Yeah, that's a Shan Sharp clip.

It went like crazy viral. Okay. So explain what's going on there. Yeah. So she's really one of my best friends still to this day. uh she was with me from day one literally in the book it's like she would hand out newspapers day one so we always had a great relationship we didn't separate because there was some scandal or anything else we both it we had love for each other but maybe we weren't in love if that makes

any sense but i've trust her implicitly she's somebody who was there with me from day one like living every up living every down hey we gotta go move in with your in-laws we have no money we can't do this we can never complained always like very supportive had my back so to me she's she's part of the growth and really we separated when the thing exploded trust her always um so it never really occurred we didn't get divorced right off the bat in fact we still haven't but it the reason the beginning was like, let's see what separation's like. And we stayed separated and you know, the money was coming in. She can do whatever I trust her. She could have always at any point still today, be like, I'm taking all the money I'm running. I just know she would

never do it as trusting somebody as much as I trust my parents. Really. Um, we did try to get divorced. It got denied by Massachusetts. Uh, so I didn't even know they could do that. Neither did it was news to me um we had an agreement set up it's like a reverse arranged marriage yeah it's great i didn't know they could do it they said it was unequitable um but she also was like i think at the time i was buying the nantucket house it's like well it if we just split everything it's just going to sit there in the bank count anyways the same way except i don't have the collateral to get the nantucket house and she didn't want it and we had a very good it's like she gets it was set up in a way exactly pretty much how we were living for the past five to six years except to

make it legal and the judge was like no so it's very rare i think in life that you have somebody that you can trust like that which you've been through the ups and downs and everything and she's one of them and i'll always be there for her and i think she'll be there for me yeah makes sense uh bitcoin you went from uh i think hating it to you became again you became the diamond hand Yeah, I hate it again. Yeah? Why? Well, what do you think? Why? It's like I'm always in at the wrong time.

When you start talking about it, I do get nervous. Yeah. As soon as I see you, you start talking, I'm like, oh, shit. So I originally, the whole Winklevoss disaster was, it was 11,000. When the Winklevosses explained to me what Bitcoin was. They came to your house. And the first time, we're both in the Hamptons. They're at the same hotel.

And they're like, we own like whatever the Bitcoin, and we're 6'2", and there's two of us. So we'll come explain it to you. And they said, Elon Musk will go to outer space. He's going to mine gold from outer space and rain down plentiful. So these fucking guys are crazy. So I had bought 2 million of it at 11,000. They walked out of the room, sold them. I do not understand any of what they're saying.

It went to like 50,000 or 60,000 in fast order. Like you can probably find the date of when they did that and see how quickly. from like august or september of 2020 to like march of 2021 six months yes so and that's when they were there august so it's like all right i if you 6x 2 million that's 12 million i was not happy and then i was like i gotta get back in it everyone's talking about this thing i've been in out i'm in right now probably at an average of like 100 bucks something like that what do we have 59 i don't know what the hell's going on with it i really nobody knows no i mean you got sailor selling it saying it's good that he's selling it who knows who knows i'm not gonna

sell it may go zero i may lose millions again all right but it's not like a material part of your net worth it's enough that i'm like i look at it every day will i be fine yeah uh but i probably had you know 15 million in it at some point 15 million dollars a bit not anymore i don't know know. But I probably did. Yeah. Yeah. You know, you know how to get 10 million as you start with 15. Yeah. I mean, I'm always, always, always on the wrong side of Bitcoin and crypto. Always. Well, there's other coins that you bought along the way and I could see like the chats, right? The chats would convince you. Well, I dabbled with meme coins, which was honestly, maybe in 20 years the craziest thing i was ever involved in like remember we did the hat uh like a college

selection and uh you picked one of the coins yeah that that was safe moon safe movie yeah and then i got mentioned in a lawsuit they're like you were an insiders like i literally picked out of a hat said i have no idea it's probably a scam and i lost all my money so but i had to hire a lawyer because there's all these influencers i guess were given free safe moon and didn't disclose and i got included in that and it's like i got my i got killed i told people but i had to pay a lawyer and then they laid out and they dismissed me from the charge but i still had to pay for it yeah so i i'm always always always on the wrong side of everything regarding that how do you pick what stocks you buy now uh i'm fairly safe right now like i i have a guy who helps me like a broker

but it it's fairly safe there's nothing crazy in there all right i want i want to uh mention three moments in barstool history you tell me what you remember from them uh brady six going to jail clearly that that's the most did you think you were going to go to jail no no they're very barstool it's like i we don't think too far in advance um i thought even when we're changing just for people don't know you change yourself so when the nfl so when brady got the four game suspension from the nfl for the valley gate we're like we gotta do something we're still in boston drove to new york put like one two eye black on patriotic year we went to nfl headquarters demanded to speak to roger goodell they said no they actually first asked if we had an appointment

and then uh they said no we handcuffed ourselves to each other in the headquarters and did a sit-in and got arrested and and the police were kind of they knew who we were at that point a little bit they're kind of joking so i didn't think we were gonna get arrested uh i was wrong we spent a day in jail it was horrible so that that's the memory did people in jail know who you were no oh the cops did the cops thank god because they were trying to move us around what do they call the tunnels that's where we were i mean if you like commit murder you go to the tunnels like it's where everybody goes who commits a crime in new york city that night and there can be some scary people there the cops knew we were not a threat and they were trying to move us around to keep

us kind of separated from like hardened criminals um yeah that you mean the guys in the patriots gear yeah right like the guys protesting brave when the judge saw us the next day and it would be like the case before us would be like domestic abuse something serious or like a murder and then we get up there and she's like what'd you do it's like we protested protested tom flick tom brady and she cracked a little smile it's off our record so yeah all right howitzer gate is probably one of the the craziest ones yeah it's funny because will compton who worked for us busting with the boys big star uh is he a star he's a star he's he's a star and i like will he's one of the guys i wish we could have back but um he texted what's he called like seal uh seal team six or whatever

what does he do what dad team six yeah he does all sorts of stuff like that but uh he texted me this morning didn't even know about brady gate that shows how long we've been doing he worked for wow had no idea what it was wow that i mean he's viral he brings you in the closet you know farts in the phone yeah yeah no he he's he is a big star yeah um howitzer gate that was was that our first really huge controversy so that's back in the blogging days when i'm just cranking out 10 to 15 blogs a day every 45 minutes looking for something uh that's interesting it's also the height of the patriots colts rivalry specifically brady versus manning like i hated peyton manning i was so team patriots whatever at this point every the

media is always peyton manning this peyton manning that colts this colts that colts 14 and 0 to start a season pages got no respect but we whooped him every year talk one day so and i'm doing my scrolling across the internet to talk about find things to talk about and lo and behold there's a picture of giselle uh brady's wife their little toddler on the beach it's an infant toddler well endowed to say the least it was like shocking so i wrote a blog check out the howitzer on brady's kid and then the sentence below is peyton manning could never have a kid like this that was it it was like a shot at peyton manning moved on didn't think anything of it like that was the whole blog yeah that was it it was like just peyton manning could never have a kid like

this press publish move on yeah i don't know how long it was a couple hours all hell breaks loose dave's a pedophile dave's posting pictures of uh kids dicks a lot of people didn't know how the internet worked people were acting like i was in the bushes with a camera a long-range camera taking the picture the picture was all over the paparazzi pages like the same pages we went to get photographed it was everywhere and i thought i was making a very clear peyton manning joke well i mean people were calling for my head the state police showed up at my house uh i was on howard stern howard stern trashed me it was it was nuts and people still in the book i talk about it people still bring up out of context tweets from that controversy as like trying to say got him

yeah like there's a tweet i have that says where where he's he's two years old it's child porn i this sounds horrible even saying i'm mimicking people who are saying that because it's like the kid's so young if you sexualize the kid you're screwed up it's like the gerber baby but people have no idea what the quote came from or what it's in con so they're like dave it's crazy um so yeah that was a that was a wild time wild all right last one is uh tico texas i didn't see that one tico texas i mean that's got it that's like catch me outside before catch me outside yeah tico texas tico texas how do we even start here so so loud sean is a rapper loud sean what a name yeah uh no was it loud no little sean big sean big sean loud sean was a

crazy employee we had big sean rapper was dating ariana grande yep they broke up kevin clancy who works for us was like what a what what a fumble by big sean you're never going to get someone bigger than aria better than aria grande you're lucky you had ariana grande there was a rapper in texas called tico texas who i don't know how her twitter feed found kevin's tweet but it did and she did not like it she was a big big sean fan how dare you say that about big sean you're an idiot she was black kevin's white she started calling him a baseball fan that was her word for like white fans and she's like you're the worst it turned into this battle and tico texas wrote a rap song about kevin dissing him kevin wrote a rebuttal rap song about tico texas also killed me

in it because i was on tico's side i was like go get kevin he's such a baseball fan whatever tico did i was like tell me more tico and uh i ended up then writing a rap song getting in the rise page use rise i went to self by self west to visit tico and one of the crazier three-day trips i've ever had she eventually was a full-time employee tico texas she just stopped showing up to work um but you had to fire oh yeah yeah just another one it is hard to get fired from barstool real hard she just wasn't showing up yeah her contract was probably up and we didn't renew uh just another one of those crazy shooting stars we've had in our universe all right you got this book uh that came out uh dave portnoy cancel me if you can i gotta say the best marketing i've seen for

book is you sitting next to the pool just open up to a random page you just start reading and it's electric oh yeah i mean that is like there is no better like let me show you yeah i wish i could read the whole thing that voice i the audiobook you can't be like that because it's hard to read like that an entire book but yeah that that i haven't felt pressure to market anything in a long time i feel pressure with the book like i don't know why i do like if it's not on the new york best best sellers list i i do you think they would put you on if you had the numbers so i didn't know that it was editorialized yeah correct now they did promote it as saying it would be one of the bigger books of the summer so maybe but yeah i i i don't know why i don't know why some things

put pressure on me i feel pressure for this to be successful all right well we don't want you to feel pressure so i do i feel pressure no i know but like if people go by the book then the pressure need to buy book by multiple they're not that expensive and for the first week when's this dropping uh today so i'm doing ten dollars because i didn't do this for money and to be honest i don't even understand how the book industry works it seems like not the most lucrative thing of all time to spend your time on a book um no offense to you know our publishing is great gallery but i don't get the finances i didn't do it for the money but so ten dollars every book i'm giving to Lifeline Animal Shelter this week,

which is basically probably all the profit, which is where I got Miss Peaches and Beat the Beetle. Barstool Fund, you did a great job there. Now you do more with the animals, right? Yep, yep. How many businesses with the Barstool Fund? We're close to 450, raised about 50 million. Yeah, that's great.

Yeah, that's probably the proudest thing that I have. Actually, that's another, I should have said, another interaction with you, Erica, and Barstool was watching you guys try to figure out how to take crypto was quite hilarious. Yes. Yeah. And there were a lot of big mouths in crypto who got shut up real quick though, because they're like, if you get it, we'll donate all this money. And that just never came. It's like, we spent all this, where's our crypto? It just never came.

I remember I introduced you guys to a company, like I will help. And then they called me back and they were like, I don't know if anyone can help them. We had no idea how to do it. None, zero. But all these people like take crypto, we'll do it, we'll do it. We did get it done and it just never came. But yeah, that was, very proud of that. I mean there's a lot of business still if i see them like we saved a lot of business a lot of great businesses so i'm proud of that listen i think that uh you probably get too much shit for the uh for the bad stuff you don't get enough credit for the good stuff so i think you're doing a great job cancel me if you can everyone go pick it up appreciate it