WEBVTT 00:00:00.000 --> 00:00:02.419 OK, I want to start this deep dive with a number, 00:00:02.580 --> 00:00:06.480 just a single number, one dollar. That is a number 00:00:06.480 --> 00:00:08.800 that breaks pretty much every business school 00:00:08.800 --> 00:00:11.019 textbook in existence. I mean, it just doesn't 00:00:11.019 --> 00:00:13.259 compute. It really doesn't. Because usually when 00:00:13.259 --> 00:00:14.800 we talk about media acquisitions, especially 00:00:14.800 --> 00:00:17.679 involving these massive, you know, publicly traded 00:00:17.679 --> 00:00:21.320 casino companies, we're talking billions or the 00:00:21.320 --> 00:00:23.660 very least hundreds of millions. Right. Billions 00:00:23.660 --> 00:00:27.480 with a B. But today we are talking about. a guy 00:00:27.480 --> 00:00:30.559 who sold his company for an absolute fortune 00:00:30.559 --> 00:00:34.299 and then in a twist that I still frankly struggle 00:00:34.299 --> 00:00:37.289 to wrap my head around bought it back for A single 00:00:37.289 --> 00:00:40.450 dollar bill. And that deal, that singular moment 00:00:40.450 --> 00:00:44.130 in August 2023, is really the skeleton key to 00:00:44.130 --> 00:00:46.189 understanding our subject today. It tells you 00:00:46.189 --> 00:00:47.609 everything you need to know about the collision 00:00:47.609 --> 00:00:50.350 between corporate America and this new concept 00:00:50.350 --> 00:00:53.210 of the uncancellable internet celebrity. Exactly. 00:00:53.350 --> 00:00:55.950 We are diving into the world of Dave Portnoy, 00:00:56.070 --> 00:00:58.869 the Presidente, the founder of Barstool Sports. 00:00:59.149 --> 00:01:00.609 And look, if you were listening to this, you 00:01:00.609 --> 00:01:02.770 probably have an opinion on him. For sure. There's 00:01:02.770 --> 00:01:05.200 no middle ground. Maybe you love the pizza reviews 00:01:05.200 --> 00:01:08.200 and swear by the app. Maybe you despise the politics 00:01:08.200 --> 00:01:11.560 in the online aggression. But our mission today 00:01:11.560 --> 00:01:14.359 isn't to judge him. It isn't to decide if he's 00:01:14.359 --> 00:01:17.319 a saint or a sinner. It is to disassemble the 00:01:17.319 --> 00:01:19.180 machine. Right. We want to understand the mechanics. 00:01:19.480 --> 00:01:23.379 How does a guy who failed as an education major 00:01:23.379 --> 00:01:27.079 build a counterculture empire that rivals legacy 00:01:27.079 --> 00:01:29.859 media? What is the actual math behind the... 00:01:30.219 --> 00:01:32.819 barstool conservatism brand. And how does he 00:01:32.819 --> 00:01:36.120 manage to be a philanthropist, saving small businesses 00:01:36.120 --> 00:01:39.120 and a self -proclaimed union buster at the exact 00:01:39.120 --> 00:01:41.920 same time? It's a paradox. And to explore it, 00:01:41.980 --> 00:01:44.140 we are pulling strictly from the biographical 00:01:44.140 --> 00:01:46.079 data, business records and public statements 00:01:46.079 --> 00:01:48.879 detailed in his Wikipedia entry, current as of 00:01:48.879 --> 00:01:51.299 early 2026. We are stripping away the noise to 00:01:51.299 --> 00:01:53.819 look at the facts. The raw data of the man, so 00:01:53.819 --> 00:01:56.359 to speak. Exactly. So whether you love him, hate 00:01:56.359 --> 00:01:58.900 him or just know him as the one bite guy, this 00:01:58.900 --> 00:02:01.030 deep dive explains how he became one of the most 00:02:01.030 --> 00:02:03.189 influential and, let's be honest, divisive voices 00:02:03.189 --> 00:02:05.750 in modern media. And what his career says about 00:02:05.750 --> 00:02:09.289 the current state of fame, finance, and cancel 00:02:09.289 --> 00:02:11.770 culture. So let's get into it. Let's do it. I 00:02:11.770 --> 00:02:13.819 want to go back to the beginning. Because the 00:02:13.819 --> 00:02:15.819 current image, you know, the private jets, the 00:02:15.819 --> 00:02:18.939 Hamptons parties, the courtside seats, it really 00:02:18.939 --> 00:02:21.520 masks a pretty desperate origin story. I think 00:02:21.520 --> 00:02:23.419 people assume he burst out of the womb with a 00:02:23.419 --> 00:02:25.780 cigar in his mouth, ready to take on the world. 00:02:25.979 --> 00:02:28.199 It definitely wasn't like that. Yeah. Not at 00:02:28.199 --> 00:02:30.879 all. And to understand the desperation and the 00:02:30.879 --> 00:02:32.599 drive that came from it, you have to look at 00:02:32.599 --> 00:02:35.199 the timeline. Dave Portnoy wasn't a prodigy. 00:02:35.199 --> 00:02:38.000 He was born in 1977 in Swampscott, Massachusetts. 00:02:38.479 --> 00:02:40.379 OK, so a pretty standard suburban background. 00:02:40.500 --> 00:02:42.789 Very standard. It was a Jewish upbringing. His 00:02:42.789 --> 00:02:46.129 dad, Michael, was a lawyer. His mom, Linda, was 00:02:46.129 --> 00:02:48.370 a high school teacher. I mean, it's the picture 00:02:48.370 --> 00:02:52.069 of a stable, middle -class American life. And 00:02:52.069 --> 00:02:54.650 I saw a note here about a weird coincidence with 00:02:54.650 --> 00:02:57.949 ESPN's Todd McShay. What's that about? Yeah, 00:02:57.990 --> 00:02:59.969 it's one of those small world details that you 00:02:59.969 --> 00:03:01.650 almost wouldn't believe if it was in a movie 00:03:01.650 --> 00:03:03.969 script. They were born in the same hospital on 00:03:03.969 --> 00:03:07.009 the exact same day. Yeah, they were classmates 00:03:07.009 --> 00:03:10.439 at Swampscott High. But their paths just diverged 00:03:10.439 --> 00:03:13.580 so dramatically. While McShay went the traditional, 00:03:13.719 --> 00:03:16.680 you know, polished sports journalism route, Portnoy 00:03:16.680 --> 00:03:19.080 went to the University of Michigan. And here 00:03:19.080 --> 00:03:21.699 is the first major contradiction in his life 00:03:21.699 --> 00:03:26.300 story. He graduated in 1999 with a degree in 00:03:26.300 --> 00:03:29.120 education. So technically, in another timeline, 00:03:29.520 --> 00:03:31.780 Dave Portnoy is teaching high school social studies 00:03:31.780 --> 00:03:34.099 somewhere in Massachusetts. Technically, he is 00:03:34.099 --> 00:03:37.300 qualified. But he's been very clear in interviews 00:03:37.300 --> 00:03:39.460 that he had zero intention of actually teaching. 00:03:39.599 --> 00:03:41.939 He just needed a degree. It was a means to an 00:03:41.939 --> 00:03:44.039 end. So the real education was happening elsewhere. 00:03:44.340 --> 00:03:46.340 His real education happened on a site he launched 00:03:46.340 --> 00:03:49.199 while he was still in college called thegamblingman 00:03:49.199 --> 00:03:51.759 .com. Which sounds less like a business plan 00:03:51.759 --> 00:03:53.659 and more like a warning sign for his parents. 00:03:53.800 --> 00:03:55.759 It was definitely a precursor, a sign of things 00:03:55.759 --> 00:03:58.819 to come. But the reality check hit him hard after 00:03:58.819 --> 00:04:01.939 graduation. He moves back to Boston and takes 00:04:01.939 --> 00:04:03.919 a job at a place called the Yankee Group. What 00:04:03.919 --> 00:04:06.680 did they do? IT market research. So just imagine 00:04:06.680 --> 00:04:09.360 that for a second. The guy who runs the wildest 00:04:09.360 --> 00:04:12.979 carnival in sports media is sitting in a cubicle 00:04:12.979 --> 00:04:17.160 analyzing tech trends. And he hated it, I'm assuming. 00:04:17.319 --> 00:04:19.920 He was miserable. Absolutely miserable. He was 00:04:19.920 --> 00:04:23.300 grinding in that cubicle. And to escape the boredom, 00:04:23.300 --> 00:04:25.980 he was betting sports heavily on the side. And 00:04:25.980 --> 00:04:28.680 when I say heavily, I mean. Destructively. How 00:04:28.680 --> 00:04:31.300 heavily are we talking? He calls himself a degenerate 00:04:31.300 --> 00:04:33.639 gambler during this period. He wasn't just losing 00:04:33.639 --> 00:04:37.060 his paycheck. In his mid -20s, he lost $30 ,000 00:04:37.060 --> 00:04:40.899 in a single year. Wow. That's a lot of money 00:04:40.899 --> 00:04:43.660 for a guy in his 20s in the early 2000s. It's 00:04:43.660 --> 00:04:46.180 a huge amount. And by 2004, the hole was too 00:04:46.180 --> 00:04:48.540 deep to climb out of. He actually filed for bankruptcy 00:04:48.540 --> 00:04:52.980 protection. Pause there. Bankruptcy. Before Barstool 00:04:52.980 --> 00:04:56.240 was even a thing? Yes. This is the crucial detail 00:04:56.240 --> 00:04:59.279 so many people miss. He owed $59 ,000 to credit 00:04:59.279 --> 00:05:02.079 card companies and another $18 ,000 to his father. 00:05:02.240 --> 00:05:04.819 He was completely underwater. So this whole empire 00:05:04.819 --> 00:05:07.399 wasn't founded by some wealthy entrepreneur with 00:05:07.399 --> 00:05:09.800 a venture capital check and a vision board? No. 00:05:10.060 --> 00:05:12.379 It was founded by a guy who had hit financial 00:05:12.379 --> 00:05:14.699 rock bottom. He was born out of desperation. 00:05:15.060 --> 00:05:17.980 He had nothing to lose, which probably explains 00:05:17.980 --> 00:05:20.689 a lot of the early risk -taking. So Barstool 00:05:20.689 --> 00:05:24.910 starts in 2004, but it's not a website yet. It's 00:05:24.910 --> 00:05:27.410 not a podcast network. What was it? No. And this 00:05:27.410 --> 00:05:30.050 is the grind part of the mythology that he always 00:05:30.050 --> 00:05:32.410 references. And for good reason. It was a four 00:05:32.410 --> 00:05:36.529 page black and white print newspaper. And he 00:05:36.529 --> 00:05:39.329 wasn't mailing it out. Portnoy was physically 00:05:39.329 --> 00:05:42.569 standing on subway platforms in Boston, handing 00:05:42.569 --> 00:05:44.899 these things out to commuters. That is a tough 00:05:44.899 --> 00:05:47.279 sell. Here, take my gambling pamphlet. I can't 00:05:47.279 --> 00:05:49.339 imagine the reception was great. It was brutal. 00:05:49.560 --> 00:05:51.680 He's talked about waking up at 4 a .m., standing 00:05:51.680 --> 00:05:54.360 in the freezing Boston cold, trying to get people 00:05:54.360 --> 00:05:56.920 to just take a piece of paper from him. The content 00:05:56.920 --> 00:05:58.980 was designed to reject political correctness. 00:05:59.120 --> 00:06:01.740 It was aimed squarely at that bro culture demographic. 00:06:02.199 --> 00:06:03.459 The guy at the end of the bar? The guy at the 00:06:03.459 --> 00:06:05.800 end of the bar, exactly. Yeah. But the financials 00:06:05.800 --> 00:06:08.120 were bleak. I mean, who wants to advertise in 00:06:08.120 --> 00:06:10.620 a pamphlet handed out by a random guy in a windbreaker 00:06:10.620 --> 00:06:14.600 on the T? And this leads to the first major strategic 00:06:14.600 --> 00:06:19.819 pivot. We talk about sex cells as a cliche, but 00:06:19.819 --> 00:06:22.240 for Portnoy, it was literally a survival tactic. 00:06:22.480 --> 00:06:25.540 The cover strategy. That's the one. He realized 00:06:25.540 --> 00:06:27.500 that a picture of a spreadsheet or a football 00:06:27.500 --> 00:06:30.480 player wasn't stopping commuters in their tracks. 00:06:30.939 --> 00:06:34.199 So he stopped putting sports stats on the cover. 00:06:34.600 --> 00:06:37.079 And he started putting photos of local women 00:06:37.079 --> 00:06:40.139 in bikinis. And I'm guessing the graph went up 00:06:40.139 --> 00:06:42.560 and to the right. Immediately. It changed the 00:06:42.560 --> 00:06:44.519 entire distribution model because people actually 00:06:44.519 --> 00:06:46.939 started picking up. Suddenly, the stack of papers 00:06:46.939 --> 00:06:49.319 he brought with him would disappear every morning. 00:06:49.420 --> 00:06:52.300 It was a crude, maybe even cynical move, but 00:06:52.300 --> 00:06:54.339 it worked. And where was the money coming from? 00:06:54.379 --> 00:06:56.639 If local businesses weren't advertising, how 00:06:56.639 --> 00:06:59.019 did he fund it? This is another key part of the 00:06:59.019 --> 00:07:01.680 early DNA. He was funding this paper largely 00:07:01.680 --> 00:07:04.519 through ads from offshore betting sites, places 00:07:04.519 --> 00:07:07.230 like Party Poker. Which were operating in a legal 00:07:07.230 --> 00:07:09.949 gray area in the US at the time, to put it mildly. 00:07:10.029 --> 00:07:13.170 Gray is very generous. They were largely illegal. 00:07:13.470 --> 00:07:15.689 The Department of Justice was actively cracking 00:07:15.689 --> 00:07:18.569 down on them. So from day one, from the very 00:07:18.569 --> 00:07:20.730 beginning, Portnoy built his business in the 00:07:20.730 --> 00:07:23.269 margins, completely outside the establishment 00:07:23.269 --> 00:07:25.509 rules. He was taking money from companies that 00:07:25.509 --> 00:07:28.589 ESPN or Fox Sports wouldn't touch with a 10 -foot 00:07:28.589 --> 00:07:30.850 pole. Exactly. And that freedom from corporate 00:07:30.850 --> 00:07:34.589 oversight became part of the brand. Then in 2007, 00:07:34.829 --> 00:07:37.689 he finally pivots to the blog format. And that's 00:07:37.689 --> 00:07:40.189 where El Presidente is truly born. Let's talk 00:07:40.189 --> 00:07:43.430 about that persona. Because there is Dave Courtenoy, 00:07:43.430 --> 00:07:45.290 the human, and then there's El Presidente, the 00:07:45.290 --> 00:07:48.129 character. And sometimes it feels like even he 00:07:48.129 --> 00:07:49.910 doesn't know where the line is. It's a total 00:07:49.910 --> 00:07:52.269 blur. But the character was a reaction to the 00:07:52.269 --> 00:07:54.470 environment at the time. You have to remember 00:07:54.470 --> 00:07:58.089 the context of 2007 -2010 sports media. Very 00:07:58.089 --> 00:08:00.660 polished. Very corporate. Incredibly polished. 00:08:00.740 --> 00:08:03.060 It was ob costas, it was suits, teleprompters, 00:08:03.100 --> 00:08:05.420 protect the shield. Portnoy offered the absolute 00:08:05.420 --> 00:08:07.939 opposite. He offered the way guys actually talked 00:08:07.939 --> 00:08:09.899 at a bar. It was crude, it was unfair, it was 00:08:09.899 --> 00:08:12.959 biased, but it felt real. Authenticity. Or at 00:08:12.959 --> 00:08:15.139 least perceived authenticity. That's the magic 00:08:15.139 --> 00:08:17.939 ingredient. That's everything. It built a connection 00:08:17.939 --> 00:08:22.089 that was incredibly sticky. His fans? The stoolies, 00:08:22.149 --> 00:08:24.589 they didn't just like the content. They identified 00:08:24.589 --> 00:08:26.509 with it. They felt like they were part of this 00:08:26.509 --> 00:08:29.269 renegade crew fighting against the suits. And 00:08:29.269 --> 00:08:32.590 that loyalty, that army he built, is what eventually 00:08:32.590 --> 00:08:35.070 attracted the big money. The really big money. 00:08:35.169 --> 00:08:36.649 Okay, let's fast forward to that money because 00:08:36.649 --> 00:08:39.110 the valuation ride here is where this story gets 00:08:39.110 --> 00:08:42.470 really technical and, frankly, fascinating. This 00:08:42.470 --> 00:08:44.269 is where the business students listening need 00:08:44.269 --> 00:08:46.529 to pay attention. It's a classic three -act play. 00:08:47.080 --> 00:08:50.240 Act one is 2016. A company called the Churning 00:08:50.240 --> 00:08:53.000 Group buys a majority stake. And what did that 00:08:53.000 --> 00:08:55.919 do for them? That was the legitimacy phase. It 00:08:55.919 --> 00:08:57.860 professionalized the operation. They moved the 00:08:57.860 --> 00:08:59.740 whole thing from a small office in Massachusetts 00:08:59.740 --> 00:09:03.059 to New York City. They got a real office. They 00:09:03.059 --> 00:09:05.820 started hiring real production staff, video editors, 00:09:06.120 --> 00:09:08.200 you know, the works. They became a real media 00:09:08.200 --> 00:09:11.360 company. They did. But act two is where it gets 00:09:11.360 --> 00:09:13.759 crazy. That's Penn Entertainment. This is the 00:09:13.759 --> 00:09:16.500 big one. And Penn isn't a media company. Not 00:09:16.500 --> 00:09:18.860 at all. They are a massive casino and gambling 00:09:18.860 --> 00:09:21.500 operator. They own racetracks and casinos all 00:09:21.500 --> 00:09:24.100 across the country. And they look at Barstool 00:09:24.100 --> 00:09:27.120 not as a blog, but as a customer acquisition 00:09:27.120 --> 00:09:29.399 funnel. They didn't want the content. They wanted 00:09:29.399 --> 00:09:31.639 the audience. They wanted the stoolies. They 00:09:31.639 --> 00:09:33.860 wanted all those young men to stop betting on 00:09:33.860 --> 00:09:36.179 DraftKings and start betting on the pen app, 00:09:36.399 --> 00:09:38.740 which they would rebrand as the Barstool Sportsbook. 00:09:38.879 --> 00:09:42.659 So they buy in. They buy a 36 % stake in early 00:09:42.659 --> 00:09:47.720 2020 for $163 million. That evaluated the company 00:09:47.720 --> 00:09:49.980 at, what, almost half a billion dollars? Which 00:09:49.980 --> 00:09:52.399 is an astronomical sum for what started as a 00:09:52.399 --> 00:09:55.320 newspaper handout. And it gets better. In February 00:09:55.320 --> 00:09:58.159 2023, they decide to buy the rest of it. They 00:09:58.159 --> 00:10:01.320 acquire the remaining 64 % for another $388 million. 00:10:01.600 --> 00:10:04.159 So Portnoy is out. She cashes out. He has hundreds 00:10:04.159 --> 00:10:06.419 of millions of dollars. The company he built 00:10:06.419 --> 00:10:08.820 from nothing is now wholly owned by a publicly 00:10:08.820 --> 00:10:11.480 traded corporation that's subject to gaming commissions 00:10:11.480 --> 00:10:15.100 in every state. And that right there is where 00:10:15.100 --> 00:10:17.679 the friction started. You see, you can't have 00:10:17.679 --> 00:10:21.519 El Presidente. A guy who is getting into public 00:10:21.519 --> 00:10:24.059 shouting matches, sparking controversies and 00:10:24.059 --> 00:10:26.960 being generally ungovernable, running a brand 00:10:26.960 --> 00:10:28.700 that's owned by a company that needs regulatory 00:10:28.700 --> 00:10:31.279 approval in strict states like Massachusetts 00:10:31.279 --> 00:10:34.240 or Nevada. The regulators started asking questions. 00:10:34.320 --> 00:10:36.000 I remember reading about this. They did more 00:10:36.000 --> 00:10:37.720 than ask questions. They looked at Portnoy and 00:10:37.720 --> 00:10:40.120 said, if you want a gambling license in our state, 00:10:40.299 --> 00:10:43.379 you can't be associated with this guy. There 00:10:43.379 --> 00:10:45.899 are public hearings where regulators specifically 00:10:45.899 --> 00:10:48.980 cited Portnoy's past comments and behavior as 00:10:48.980 --> 00:10:52.500 reasons to deny Penn a license. So Penn was facing 00:10:52.500 --> 00:10:55.259 a choice. A very stark choice. Keep Barstool 00:10:55.259 --> 00:10:57.419 and risk losing their licenses, which is their 00:10:57.419 --> 00:10:59.419 actual, you know, multi -billion dollar business. 00:10:59.539 --> 00:11:02.860 Or dump Barstool and save the mothership. So 00:11:02.860 --> 00:11:05.279 they dumped it. But the price tag, going back 00:11:05.279 --> 00:11:09.240 to our intro, $1. August 2023, just six months 00:11:09.240 --> 00:11:11.679 after spending $388 million to buy the rest of 00:11:11.679 --> 00:11:14.080 the company, Penn Entertainment sells 100 % of 00:11:14.080 --> 00:11:16.820 Barstool Sports back to Dave Portnoy for $1. 00:11:16.919 --> 00:11:18.740 I still need you to explain the economics of 00:11:18.740 --> 00:11:21.340 that. Penn spent over half a billion dollars 00:11:21.340 --> 00:11:25.080 total. Why give it away for a buck? Why not sell 00:11:25.080 --> 00:11:28.259 it to someone else for, I don't know, $50 million, 00:11:28.659 --> 00:11:32.220 $100 million? Two reasons. Speed and liability. 00:11:32.519 --> 00:11:35.440 To sell it to a third party takes months, maybe 00:11:35.440 --> 00:11:38.179 even a year. You need due diligence, negotiations, 00:11:38.600 --> 00:11:41.620 lawyers. Penn needed to stop the bleeding immediately 00:11:41.620 --> 00:11:44.940 to save their licenses. Every single day they 00:11:44.940 --> 00:11:47.679 held on to Barstool was a risk to their core 00:11:47.679 --> 00:11:49.860 gaming operation. OK, so speed was a factor. 00:11:49.899 --> 00:11:52.399 What about liability? Portnoy was the brand. 00:11:52.879 --> 00:11:55.360 Without him, the asset is worth significantly 00:11:55.360 --> 00:11:58.179 less. I mean, who buys Barstool without Dave 00:11:58.179 --> 00:12:00.759 Portnoy? The brand is completely tied to his 00:12:00.759 --> 00:12:02.909 personality. So they couldn't just sell it to 00:12:02.909 --> 00:12:04.750 a private equity firm and keep him on. Because 00:12:04.750 --> 00:12:06.590 he's the reason they had to sell it in the first 00:12:06.590 --> 00:12:09.450 place. Exactly. It's catch 22. So they essentially 00:12:09.450 --> 00:12:11.870 wrote it off as a massive marketing expense that 00:12:11.870 --> 00:12:14.269 went horribly wrong. They took a half billion 00:12:14.269 --> 00:12:16.250 dollar loss on the balance sheet to save the 00:12:16.250 --> 00:12:18.169 rest of the company. But Portnoy didn't get it 00:12:18.169 --> 00:12:20.029 back scot -free, right? There were some strings 00:12:20.029 --> 00:12:23.169 attached. Oh, yeah. There are some serious golden 00:12:23.169 --> 00:12:26.429 handcuffs in that deal. For one, he signed non 00:12:26.429 --> 00:12:28.830 -compete agreements regarding gambling. You can't 00:12:28.830 --> 00:12:30.309 just turn around and start a sportsbook with 00:12:30.309 --> 00:12:32.129 DraftKings the next day. That makes sense. And 00:12:32.129 --> 00:12:33.889 the big one, the one that really matters, is 00:12:33.889 --> 00:12:36.309 a clause stating that if he ever sells Barstool 00:12:36.309 --> 00:12:39.529 again, Penn gets 50 % of the gross proceeds. 00:12:40.009 --> 00:12:42.190 Ah, so they kept a lottery ticket just in case. 00:12:42.190 --> 00:12:44.450 If he built it back up and sells it for a billion 00:12:44.450 --> 00:12:48.169 in 10 years, they get half a billion back. Precisely. 00:12:48.549 --> 00:12:51.309 But from Portnoy's perspective, he got his empire 00:12:51.309 --> 00:12:53.620 back. He kept the hundreds of millions from the 00:12:53.620 --> 00:12:56.779 initial sale, and he regained total and complete 00:12:56.779 --> 00:12:59.759 editorial freedom. He no longer has to answer 00:12:59.759 --> 00:13:01.600 to a board of directors or a gaming commission. 00:13:01.860 --> 00:13:04.480 It's arguably the greatest trade in media history. 00:13:04.600 --> 00:13:06.299 It's unbelievable. And since getting it back, 00:13:06.399 --> 00:13:08.580 he hasn't exactly stayed small. We are recording 00:13:08.580 --> 00:13:11.700 this in January 2026. What has he been doing 00:13:11.700 --> 00:13:14.919 with that freedom? Well, paradoxically, he pivoted 00:13:14.919 --> 00:13:17.629 back toward the mainstream. In a huge move in 00:13:17.629 --> 00:13:20.769 July 2025, he announced a wide -ranging partnership 00:13:20.769 --> 00:13:23.289 with Fox Sports. He became an analyst on Big 00:13:23.289 --> 00:13:25.330 Noon Kickoff, which is their flagship college 00:13:25.330 --> 00:13:28.269 football show. Which is just so ironic. The guy 00:13:28.269 --> 00:13:31.090 who spent 20 years mocking the suits at ESPN 00:13:31.090 --> 00:13:34.350 and Fox is now sitting at the desk wearing a 00:13:34.350 --> 00:13:36.789 blazer. Well, maybe not a blazer, knowing him. 00:13:37.070 --> 00:13:40.370 But he is part of the broadcast. It signals a 00:13:40.370 --> 00:13:43.120 major shift. He's now powerful enough that the 00:13:43.120 --> 00:13:45.320 establishment needs him more than he needs them. 00:13:45.759 --> 00:13:48.460 Fox knows that traditional TV viewership is aging 00:13:48.460 --> 00:13:51.379 out. Portnoy brings the youth. He's a direct 00:13:51.379 --> 00:13:54.200 pipeline to the 18 to 34 -year -old male demographic. 00:13:54.519 --> 00:13:57.000 He also launched a new product line with a pretty 00:13:57.000 --> 00:14:00.379 big partner. Yeah, Lucky One Lemonade. It's a 00:14:00.379 --> 00:14:03.580 vodka -based, ready -to -drink beverage. And 00:14:03.580 --> 00:14:05.580 he partnered with High Noon, which is a giant 00:14:05.580 --> 00:14:07.679 in that space. But the branding is all built 00:14:07.679 --> 00:14:10.200 around his dog, Miss Peaches, with a goal raising 00:14:10.200 --> 00:14:12.299 a million dollars for animal rescue charities. 00:14:12.639 --> 00:14:14.360 We'll definitely get to the dog because she is 00:14:14.360 --> 00:14:16.080 a celebrity in her own right. But I want to talk 00:14:16.080 --> 00:14:18.059 about the content engine that makes all of this 00:14:18.059 --> 00:14:20.919 possible. Because for millions of people, especially 00:14:20.919 --> 00:14:23.480 on platforms like TikTok, Dave Portnoy isn't 00:14:23.480 --> 00:14:26.100 the guy who swindled a casino company. He's just 00:14:26.100 --> 00:14:28.559 the guy who eats pizza. The One Bite Reviews. 00:14:28.960 --> 00:14:32.460 It is a masterclass, a true case study in how 00:14:32.460 --> 00:14:35.340 simple, niche content can absolutely dominate 00:14:35.340 --> 00:14:39.480 an algorithm. He started it back in 2017. The 00:14:39.480 --> 00:14:42.259 premise couldn't be simpler. Review every pizza 00:14:42.259 --> 00:14:45.179 place in Manhattan. One bite, everybody knows 00:14:45.179 --> 00:14:48.240 the rules. That's the catchphrase. And he has 00:14:48.240 --> 00:14:50.759 a 0 to 10 scoring scale. The whole thing feels 00:14:50.759 --> 00:14:53.200 very lo -fi, very authentic. He's just a guy 00:14:53.200 --> 00:14:55.580 on a sidewalk with an iPhone. But it's the economic 00:14:55.580 --> 00:14:58.240 impact that's just wild. The Portnoy bump. The 00:14:58.240 --> 00:14:59.960 New York Times and other outlets have analyzed 00:14:59.960 --> 00:15:03.759 this. They found that a score over a 9 .0, which 00:15:03.759 --> 00:15:06.000 is incredibly rare, he's a very tough grader, 00:15:06.059 --> 00:15:08.700 isn't just a nice compliment. It is a winning 00:15:08.700 --> 00:15:10.980 lottery ticket for a small business. What does 00:15:10.980 --> 00:15:13.620 that actually look like for a pizzeria? We're 00:15:13.620 --> 00:15:15.159 talking about pizzerias that were just doing 00:15:15.159 --> 00:15:17.480 OK, maybe breaking even, that suddenly have lines 00:15:17.480 --> 00:15:19.600 around the block for six months straight. They 00:15:19.600 --> 00:15:21.620 go from a local neighborhood spot to a national 00:15:21.620 --> 00:15:23.299 destination overnight. They have to hire more 00:15:23.299 --> 00:15:25.320 staff. They start shipping frozen pizzas nationwide. 00:15:25.779 --> 00:15:28.220 Their revenue doubles or triples, sometimes more, 00:15:28.360 --> 00:15:31.259 literally overnight. But it cuts both ways. A 00:15:31.259 --> 00:15:34.159 bad review can hurt. Oh, absolutely. He can crush 00:15:34.159 --> 00:15:37.259 a place, too, or at least create a massive headache 00:15:37.259 --> 00:15:40.730 for the owner. The dragon pizza incident in Somerville, 00:15:40.750 --> 00:15:44.169 Massachusetts, back in August of 2023, is the 00:15:44.169 --> 00:15:45.850 prime example of that. That was the shouting 00:15:45.850 --> 00:15:48.830 match that went viral, right? It was ugly. It 00:15:48.830 --> 00:15:50.970 was really uncomfortable to watch. He took a 00:15:50.970 --> 00:15:52.690 bite of the pizza and called it a floppy mess. 00:15:53.029 --> 00:15:56.539 He gave it a low score. And the owner... A guy 00:15:56.539 --> 00:15:58.580 named Charlie Red came storming out of the shop 00:15:58.580 --> 00:16:00.940 and confronted him. He wasn't having it. He didn't 00:16:00.940 --> 00:16:03.299 care about the camera at all. He told Portnoy 00:16:03.299 --> 00:16:05.419 to leave his property, called him all sorts of 00:16:05.419 --> 00:16:07.779 names. They stood on the sidewalk just screaming 00:16:07.779 --> 00:16:10.139 expletives at each other. Portnoy was yelling, 00:16:10.240 --> 00:16:12.360 I judge pizza. And the owner was yelling back, 00:16:12.460 --> 00:16:14.720 I don't care. Get out of here. And the Internet 00:16:14.720 --> 00:16:17.799 ate it up. That's the entire point. The conflict 00:16:17.799 --> 00:16:20.460 drove just as much engagement, if not more, than 00:16:20.460 --> 00:16:23.460 a glowing review. Portnoy understands a fundamental 00:16:23.460 --> 00:16:26.370 truth of the Internet. Anger travels faster than 00:16:26.370 --> 00:16:29.590 praise. And he even monetized the pizza concept 00:16:29.590 --> 00:16:32.009 further, didn't he? Yeah, the One Bite Pizza 00:16:32.009 --> 00:16:35.090 Festival. It started in 2023 in Brooklyn. He 00:16:35.090 --> 00:16:37.610 basically brings all the top -rated pizzerias 00:16:37.610 --> 00:16:39.850 from his reviews together in one place, sells 00:16:39.850 --> 00:16:42.669 tickets for $100 or whatever, and thousands of 00:16:42.669 --> 00:16:44.470 people show up to eat pizza. It's brilliant. 00:16:44.809 --> 00:16:47.470 It is. But he also seems ruthless about his own 00:16:47.470 --> 00:16:49.789 content performance. Yeah. He treats his own 00:16:49.789 --> 00:16:53.509 shows like stocks in a portfolio. If one is underperforming, 00:16:53.740 --> 00:16:56.700 He just cuts it. He is completely unsentimental. 00:16:56.700 --> 00:16:58.919 He had a podcast, The Dave Portnoy Show with 00:16:58.919 --> 00:17:01.460 Eddie and Co. It was doing fine by any normal 00:17:01.460 --> 00:17:04.299 standard. But in 2022, he just put it on hiatus. 00:17:04.919 --> 00:17:07.259 Indefinitely. And his reason. He publicly said 00:17:07.259 --> 00:17:09.299 it was terrible. He said the quality had dipped. 00:17:09.319 --> 00:17:11.180 The energy wasn't there. And instead of letting 00:17:11.180 --> 00:17:13.440 it limp along and collect ad revenue, he killed 00:17:13.440 --> 00:17:16.119 it. That is so rare. Most creators have a huge 00:17:16.119 --> 00:17:18.279 ego about their shows. They want to keep the 00:17:18.279 --> 00:17:20.220 streak alive, keep the numbers up, even if the 00:17:20.220 --> 00:17:22.799 quality suffers. His ego seems to be tied to 00:17:22.799 --> 00:17:25.339 winning, not just to existing. You see that with 00:17:25.339 --> 00:17:27.960 his expansion into golf as well. The Internet 00:17:27.960 --> 00:17:30.180 Invitational. It's this big YouTube golf tournament 00:17:30.180 --> 00:17:33.319 he puts on. The 2025 edition, which aired late 00:17:33.319 --> 00:17:37.210 last year. It got over 25 million views. 25 million. 00:17:37.470 --> 00:17:41.569 That's a number that rivals major network broadcasts 00:17:41.569 --> 00:17:45.609 for actual PGA Tour events. And he's doing it 00:17:45.609 --> 00:17:47.549 just by putting a bunch of influencers on a golf 00:17:47.549 --> 00:17:49.690 course. It's a whole new media model. Okay, so 00:17:49.690 --> 00:17:52.250 we have the business genius and the content machine. 00:17:52.549 --> 00:17:55.769 Now we have to wade into the murky waters. Politics. 00:17:56.329 --> 00:17:58.849 This is where people really start to divide on 00:17:58.849 --> 00:18:00.549 him. This is where it gets really complicated. 00:18:00.750 --> 00:18:03.509 The barstool conservatism. Define that for me. 00:18:03.950 --> 00:18:05.750 Because he doesn't seem to fit the traditional 00:18:05.750 --> 00:18:08.890 Republican mold at all. He absolutely doesn't. 00:18:08.890 --> 00:18:12.289 He describes himself as socially liberal, fiscally 00:18:12.289 --> 00:18:14.670 conservative. And there's some evidence for that. 00:18:14.769 --> 00:18:17.569 Back in 2013, he actually tried to run for mayor 00:18:17.569 --> 00:18:20.089 of Boston as a libertarian. I did not know that. 00:18:20.170 --> 00:18:21.930 Yeah, he failed to get enough signatures to get 00:18:21.930 --> 00:18:24.269 on the ballot. But he did raise about $17 ,000. 00:18:24.430 --> 00:18:27.279 It was a real campaign for a minute. But the 00:18:27.279 --> 00:18:29.940 modern definition of his politics is defined 00:18:29.940 --> 00:18:32.839 almost entirely by his relationship with Donald 00:18:32.839 --> 00:18:34.700 Trump. But it's not a straight line of support, 00:18:34.900 --> 00:18:37.480 is it? It feels, well, it feels complicated. 00:18:37.839 --> 00:18:40.960 It's transactional and it's aesthetic. He endorsed 00:18:40.960 --> 00:18:44.019 Trump back in 2016. But you have to look at his 00:18:44.019 --> 00:18:45.880 reasoning. He wrote a blog post about it and 00:18:45.880 --> 00:18:47.980 he said, quote, I don't care if he's a joke. 00:18:48.200 --> 00:18:50.900 I love the fact that he is making other politicians 00:18:50.900 --> 00:18:53.710 squirm. So it wasn't about policy. It was about 00:18:53.710 --> 00:18:56.130 the disruption. He liked that Trump was upsetting 00:18:56.130 --> 00:18:58.490 the same people in the media and politics that 00:18:58.490 --> 00:19:02.130 hated Barstool. He likes the chaos. He loves 00:19:02.130 --> 00:19:05.690 the chaos. He likes that Trump plays by a different 00:19:05.690 --> 00:19:08.150 set of rules, just like he does. He ended up 00:19:08.150 --> 00:19:10.309 interviewing Trump at the White House in 2020, 00:19:10.569 --> 00:19:12.809 which was a massive coup for a sports blogger. 00:19:12.869 --> 00:19:15.049 A huge moment of validation for him. Absolutely. 00:19:15.349 --> 00:19:17.849 And he voted for him again in 2024. But then 00:19:17.849 --> 00:19:21.849 look at April 2025. The event that traders started 00:19:21.849 --> 00:19:24.930 calling Orange Monday. This was the tariff issue. 00:19:25.109 --> 00:19:27.450 Right. Trump's second term tariffs hit the market 00:19:27.450 --> 00:19:30.029 hard. And Portnoy is a heavy day trader. He has 00:19:30.029 --> 00:19:32.569 this live stream called Davy Day Trader. He went 00:19:32.569 --> 00:19:34.690 on camera and revealed he had lost $20 million. 00:19:35.150 --> 00:19:38.690 $20 million? $20 million. 15 % of his net worth 00:19:38.690 --> 00:19:41.349 at the time. Gone. Basically instantly because 00:19:41.349 --> 00:19:43.710 of the market reaction to the tariffs. Now, most 00:19:43.710 --> 00:19:45.829 people would turn on a politician who cost them 00:19:45.829 --> 00:19:49.950 $20 million in a single afternoon. And he criticized 00:19:49.950 --> 00:19:52.109 the policy for sure. He was on camera shouting 00:19:52.109 --> 00:19:54.309 at the screens, totally panicked. But he also 00:19:54.309 --> 00:19:57.529 said, this is a direct quote, I'm going to roll 00:19:57.529 --> 00:20:01.049 with him. See how this pans out. He respects 00:20:01.049 --> 00:20:03.690 the high stakes nature of it. He views politics 00:20:03.690 --> 00:20:06.029 almost like sports betting. You know, sometimes 00:20:06.029 --> 00:20:08.230 you lose big, but you respect the game. It's 00:20:08.230 --> 00:20:11.089 an interesting perspective. But where he truly 00:20:11.089 --> 00:20:13.890 breaks from the traditional right is on social 00:20:13.890 --> 00:20:17.339 issues, specifically abortion. He was incredibly 00:20:17.339 --> 00:20:19.720 vocal when Roe v. Wade was overturned in 2022. 00:20:20.099 --> 00:20:22.819 And not in a subtle way. Not at all. He released 00:20:22.819 --> 00:20:25.359 a video rant calling the decision pure insanity. 00:20:25.839 --> 00:20:28.259 He said it makes voting for Republicans dangerous 00:20:28.259 --> 00:20:30.059 because of the Supreme Court appointments they 00:20:30.059 --> 00:20:32.460 make. He has this very pure libertarian view 00:20:32.460 --> 00:20:34.519 on it. He said it makes no sense how anybody 00:20:34.519 --> 00:20:36.640 thinks it's their right to tell a woman what 00:20:36.640 --> 00:20:39.079 to do with her body. And that must have alienated 00:20:39.079 --> 00:20:42.299 a lot of his Magie -aligned fan base. It did. 00:20:42.720 --> 00:20:45.009 But he didn't seem to care. He has these core 00:20:45.009 --> 00:20:47.390 principles, and that's one of them. But then, 00:20:47.410 --> 00:20:50.069 on the flip side, he'll turn around and say something 00:20:50.069 --> 00:20:52.670 that completely enrages the left, like the Greta 00:20:52.670 --> 00:20:56.190 Thunberg comments. That was from June 2025. What 00:20:56.190 --> 00:20:58.630 happened there? Reports came out that Greta Thunberg 00:20:58.630 --> 00:21:01.910 was on a boat delivering aid to Gaza. Portnoy 00:21:01.910 --> 00:21:03.630 discussed it on one of his shows and basically 00:21:03.630 --> 00:21:05.869 said he hoped a missile would hit her boat. That 00:21:05.869 --> 00:21:09.869 is... extreme, even for him. It's the shock jock 00:21:09.869 --> 00:21:12.490 DNA coming out. He pushes the envelope right 00:21:12.490 --> 00:21:14.269 to the edge of the cliff and then a little bit 00:21:14.269 --> 00:21:16.589 over. He wants the reaction. He wants to say 00:21:16.589 --> 00:21:18.589 the thing you're absolutely not supposed to say. 00:21:19.049 --> 00:21:21.470 And this brings us right to the central paradox 00:21:21.470 --> 00:21:24.509 of the man. How can a guy who wishes violence 00:21:24.509 --> 00:21:27.710 on a climate activist also be considered a hero 00:21:27.710 --> 00:21:30.089 by so many communities? The philanthropy. It's 00:21:30.089 --> 00:21:31.970 the other side of the coin. It is the shield 00:21:31.970 --> 00:21:34.559 that deflects so much of the criticism. You cannot 00:21:34.559 --> 00:21:36.519 have an honest conversation about Dave Portnoy 00:21:36.519 --> 00:21:38.480 without talking about the Barstool Fund. Take 00:21:38.480 --> 00:21:41.440 us back to 2020. The world is shut down. It's 00:21:41.440 --> 00:21:43.819 the height of the pandemic. Lockdowns are everywhere. 00:21:44.160 --> 00:21:46.779 Small businesses are just being absolutely crushed. 00:21:47.099 --> 00:21:49.559 The government relief, the PPP loans, it was 00:21:49.559 --> 00:21:52.079 all slow and confusing and hard to get. And Portnoy 00:21:52.079 --> 00:21:55.420 steps in. He launches a fund with a dead simple 00:21:55.420 --> 00:21:58.940 premise. If you're a small business owner. Send 00:21:58.940 --> 00:22:01.539 us a video telling us your story. If we like 00:22:01.539 --> 00:22:03.720 it, if we believe in you, we will cut you a check 00:22:03.720 --> 00:22:05.299 to keep your lights on, no strings attached. 00:22:05.640 --> 00:22:08.160 And just exploded, right. It went viral instantly. 00:22:08.759 --> 00:22:12.680 By May of 2021, he had raised over $39 million 00:22:12.680 --> 00:22:17.359 for 348 businesses. He was saving mom and pop 00:22:17.359 --> 00:22:20.619 shops, dry cleaners, bowling alleys, little restaurants 00:22:20.619 --> 00:22:22.880 and bars, while the government was still arguing 00:22:22.880 --> 00:22:24.920 about the paperwork. And he would call the owners 00:22:24.920 --> 00:22:27.220 personally? He would FaceTime the owners to tell 00:22:27.220 --> 00:22:28.900 them they were getting the money, and he'd post 00:22:28.900 --> 00:22:31.420 the videos. And these videos were incredibly 00:22:31.420 --> 00:22:33.420 emotional. You'd see these 50 -year -old guys, 00:22:33.599 --> 00:22:36.059 tough guys, just breaking down in tears because 00:22:36.059 --> 00:22:39.160 their life's work was being saved. It softened 00:22:39.160 --> 00:22:41.480 his public image immensely. It proved he could 00:22:41.480 --> 00:22:44.400 mobilize his army, as he calls them, for good. 00:22:44.839 --> 00:22:47.099 And lately, that mobilization has been about 00:22:47.099 --> 00:22:50.099 animals. Miss Peaches. He adopted her from a 00:22:50.099 --> 00:22:52.400 shelter in Atlanta. She was a rescue pit bull, 00:22:52.480 --> 00:22:54.640 and she looked pretty rough when he got her. 00:22:54.980 --> 00:22:57.119 He nursed her back to health, and she became 00:22:57.119 --> 00:23:00.140 this massive Internet sensation. So he uses her 00:23:00.140 --> 00:23:02.839 fame for fundraising. Constantly. He uses her 00:23:02.839 --> 00:23:05.299 likeness on merchandise, hoodies, T -shirts, 00:23:05.359 --> 00:23:10.240 all that stuff. In 2024 alone, he donated $277 00:23:10.240 --> 00:23:13.640 ,000 to the Lifeline Animal Project in Atlanta, 00:23:13.880 --> 00:23:16.160 which is where he got her. And he also puts his 00:23:16.160 --> 00:23:18.380 own money up for law enforcement families, too. 00:23:18.500 --> 00:23:21.420 Huge amounts of his own money. When NYPD officer 00:23:21.420 --> 00:23:23.539 Jonathan Diller was killed in the line of duty 00:23:23.539 --> 00:23:27.259 in 2024, Portnoy launched a fundraiser, and he 00:23:27.259 --> 00:23:30.400 personally matched donations up to $750 ,000. 00:23:31.150 --> 00:23:33.730 The fund raised over $1 .5 million total for 00:23:33.730 --> 00:23:35.630 the family. He did it again recently, right? 00:23:35.789 --> 00:23:38.849 Just in December 2025. A Delaware state trooper 00:23:38.849 --> 00:23:41.450 was killed, and he raised nearly half a million 00:23:41.450 --> 00:23:43.269 dollars for that family. So here is the tension. 00:23:43.710 --> 00:23:46.490 He saves puppies, he saves businesses, he supports 00:23:46.490 --> 00:23:50.849 grieving widows. But then, union buster. Right. 00:23:51.309 --> 00:23:53.210 This is the dark side of the business model. 00:23:53.509 --> 00:23:55.690 You can't separate the charity from the combat. 00:23:56.289 --> 00:24:00.380 The union issue goes back to 2019. Employees 00:24:00.380 --> 00:24:03.440 at The Ringer, Bill Simmons' company, were unionizing. 00:24:03.579 --> 00:24:06.259 And Portnoy had thoughts. He had some very strong 00:24:06.259 --> 00:24:09.420 thoughts. He tweeted that he would fire any of 00:24:09.420 --> 00:24:12.279 his own employees on the spot if they so much 00:24:12.279 --> 00:24:14.700 have contacted a union organizer. Which is, I 00:24:14.700 --> 00:24:16.559 should point out, completely illegal under U 00:24:16.559 --> 00:24:18.759 .S. labor law. You cannot threaten to fire people 00:24:18.759 --> 00:24:21.119 for organizing. 100 % illegal. And the National 00:24:21.119 --> 00:24:23.730 Relations Board, the NLRB, they stepped in. They 00:24:23.730 --> 00:24:25.630 launched a formal investigation. He eventually 00:24:25.630 --> 00:24:28.210 had to settle with them, delete the tweets, post 00:24:28.210 --> 00:24:29.990 notices in the office acknowledging workers' 00:24:30.170 --> 00:24:32.829 rights, the whole standard punishment. But what 00:24:32.829 --> 00:24:36.109 did Dave do? Did he apologize? Did he say, I 00:24:36.109 --> 00:24:38.309 learned my lesson about labor law? Let me guess. 00:24:38.430 --> 00:24:40.950 He made a T -shirt about it. He made a T -shirt 00:24:40.950 --> 00:24:43.869 with his own face on it that said Union Buster 00:24:43.869 --> 00:24:47.789 and sold it to his fans for 25 bucks a pop. He 00:24:47.789 --> 00:24:49.769 took a federal investigation and turned it into 00:24:49.769 --> 00:24:52.900 a new revenue stream. It was a masterclass in 00:24:52.900 --> 00:24:56.039 defiance. That seems to be the pattern. Controversy 00:24:56.039 --> 00:24:59.140 equals cash. But surely there is a line. What 00:24:59.140 --> 00:25:02.279 about the sexual assault allegations? That felt 00:25:02.279 --> 00:25:04.420 different. That was the biggest threat to his 00:25:04.420 --> 00:25:07.579 uncancellable status. It was a series of articles 00:25:07.579 --> 00:25:10.059 from Business Insider. They published two major 00:25:10.059 --> 00:25:14.660 exposés in late 2021 and early 2022. And these 00:25:14.660 --> 00:25:16.960 weren't just about offensive jokes. No, these 00:25:16.960 --> 00:25:19.440 are serious allegations. Multiple women came 00:25:19.440 --> 00:25:21.960 forward and alleged violent, aggressive sexual 00:25:21.960 --> 00:25:24.500 encounters and in some cases non -consensual 00:25:24.500 --> 00:25:26.559 filming. How did he respond to that? He denied 00:25:26.559 --> 00:25:28.740 them vehemently. He went on the offensive immediately. 00:25:28.980 --> 00:25:31.059 He claimed every single encounter was consensual. 00:25:31.180 --> 00:25:33.420 He called the articles hit pieces and character 00:25:33.420 --> 00:25:35.799 assassination. He basically argued that Business 00:25:35.799 --> 00:25:37.960 Insider was a competitor and was trying to take 00:25:37.960 --> 00:25:39.559 him down because they didn't like his politics 00:25:39.559 --> 00:25:41.920 or his style. He sued them for defamation, right? 00:25:42.059 --> 00:25:45.470 He did. He filed a lawsuit against Business Insider 00:25:45.470 --> 00:25:48.410 and its parent company. And what was the legal 00:25:48.410 --> 00:25:51.430 outcome of that lawsuit? A federal judge dismissed 00:25:51.430 --> 00:25:54.970 the lawsuit in November of 2022. The judge ruled 00:25:54.970 --> 00:25:57.950 that Portnoy, as a public figure, had failed 00:25:57.950 --> 00:26:01.710 to prove actual malice, which is the very high 00:26:01.710 --> 00:26:03.490 legal standard you have to meet. So what does 00:26:03.490 --> 00:26:06.410 that mean in plain English? It means he couldn't 00:26:06.410 --> 00:26:08.250 prove that Business Insider knew the stories 00:26:08.250 --> 00:26:10.980 were false and published them anyway. It's not 00:26:10.980 --> 00:26:13.099 a judgment on whether the allegations were true 00:26:13.099 --> 00:26:15.680 or false, just that the reporting met the legal 00:26:15.680 --> 00:26:18.059 standard for journalism about a public figure. 00:26:18.799 --> 00:26:21.039 Portnoy initially appealed the decision, but 00:26:21.039 --> 00:26:23.299 then he dropped the appeal in February 2023. 00:26:23.759 --> 00:26:26.640 So legally, the defamation case failed. But because 00:26:26.640 --> 00:26:28.740 it wasn't a criminal trial against him, he was 00:26:28.740 --> 00:26:30.680 able to maintain his innocence in the court of 00:26:30.680 --> 00:26:32.420 public opinion, at least with his followers. 00:26:32.680 --> 00:26:35.430 And his audience stayed with him. They bought 00:26:35.430 --> 00:26:38.130 his narrative completely. They viewed it as the 00:26:38.130 --> 00:26:40.809 mainstream media attacking their guy. And this 00:26:40.809 --> 00:26:43.069 is where the uncancellable theory really holds 00:26:43.069 --> 00:26:46.069 up. If you own your platform and your audience 00:26:46.069 --> 00:26:47.910 doesn't care what the New York Times or Business 00:26:47.910 --> 00:26:50.829 Insider says about you, you are essentially immune. 00:26:51.269 --> 00:26:53.569 Advertisers might leave for a while. Advertisers 00:26:53.569 --> 00:26:56.049 might leave. But if you have subscriptions and 00:26:56.049 --> 00:26:58.490 merchandise and direct -to -consumer revenue... 00:26:58.990 --> 00:27:00.950 You can survive. You're not beholden to them. 00:27:01.069 --> 00:27:03.910 He also has a long history of refusing to apologize 00:27:03.910 --> 00:27:07.470 for offensive humor. The rape jokes, the videos 00:27:07.470 --> 00:27:09.549 that surfaced of him using racial slurs in the 00:27:09.549 --> 00:27:12.349 past. He views an apology as blood in the water. 00:27:12.690 --> 00:27:14.730 It's his core philosophy, and he has said this 00:27:14.730 --> 00:27:17.450 many times, is that if you apologize to the Internet 00:27:17.450 --> 00:27:19.869 mob, they don't forgive you. They just sense 00:27:19.869 --> 00:27:22.029 weakness and attack you even harder. So he doubles 00:27:22.029 --> 00:27:24.789 down every single time. Every time. He says, 00:27:24.869 --> 00:27:26.569 I'm a comedian, it's a joke, and he moves on. 00:27:26.859 --> 00:27:29.099 The skinny jeans comment from way back in 2010 00:27:29.099 --> 00:27:31.720 is the classic example. He wrote a blog joking 00:27:31.720 --> 00:27:34.079 that a woman who is size 6 and wears skinny jeans 00:27:34.079 --> 00:27:37.279 kind of deserves to be raped. Which is just, 00:27:37.339 --> 00:27:40.400 it's horrific. It's indefensible. It is. But 00:27:40.400 --> 00:27:42.420 when Inside Edition confronted him about it years 00:27:42.420 --> 00:27:45.180 later, asking him if he knew how offensive that 00:27:45.180 --> 00:27:47.099 was, he looked right into the camera and said, 00:27:47.220 --> 00:27:49.599 no, I obviously don't. I think it's a funny joke. 00:27:50.039 --> 00:27:52.680 It takes a specific kind of personality to stare 00:27:52.680 --> 00:27:54.960 into a camera and say that without flinching. 00:27:54.960 --> 00:27:58.559 It does. And clearly it pays. I mean, let's look 00:27:58.559 --> 00:28:00.980 at the lifestyle this uncancellable brand has 00:28:00.980 --> 00:28:03.480 bought him. We mentioned the private jets, but 00:28:03.480 --> 00:28:06.079 the real estate portfolio is just staggering. 00:28:06.079 --> 00:28:09.180 The total portfolio is valued at around $65 million. 00:28:09.759 --> 00:28:12.019 The Nantucket house made national headlines. 00:28:12.339 --> 00:28:17.380 He bought it in 2023. for $43 million. At the 00:28:17.380 --> 00:28:19.660 time, it was the most expensive home ever sold 00:28:19.660 --> 00:28:21.660 in the entire state of Massachusetts. That is 00:28:21.660 --> 00:28:23.859 succession -level wealth. That is not blogger 00:28:23.859 --> 00:28:27.140 wealth. Not even close. He also has a $14 million 00:28:27.140 --> 00:28:30.279 waterfront place in Miami, a nearly $10 million 00:28:30.279 --> 00:28:33.480 home in Montauk out on Long Island, and a smaller 00:28:33.480 --> 00:28:35.519 spot in Saratoga Springs because he loves horse 00:28:35.519 --> 00:28:38.160 racing. He's collecting trophies. These houses 00:28:38.160 --> 00:28:40.900 are trophies. But there is one detail about his 00:28:40.900 --> 00:28:43.519 finances that I found really interesting, and 00:28:43.519 --> 00:28:46.319 it involves his ex -wife, Renee. Renee Satterthwaite. 00:28:46.339 --> 00:28:47.920 Yeah, this is a fascinating part of his story. 00:28:48.059 --> 00:28:51.519 They were married from 2009 to 2017. So she was 00:28:51.519 --> 00:28:53.160 there for the really tough years. He was there 00:28:53.160 --> 00:28:54.619 for the bankruptcy. She was there when he was 00:28:54.619 --> 00:28:57.140 handing out newspapers on a freezing subway corner. 00:28:57.380 --> 00:28:59.559 She was the one behind the scenes when absolutely 00:28:59.559 --> 00:29:01.960 nobody knew who Dave Portnoy was. Lean years. 00:29:02.140 --> 00:29:05.519 Exactly. And Portnoy has stated publicly. even 00:29:05.519 --> 00:29:08.099 after their divorce, that he allows her complete 00:29:08.099 --> 00:29:11.200 access to his money and his assets. He takes 00:29:11.200 --> 00:29:14.019 care of her financially to a huge degree because 00:29:14.019 --> 00:29:16.740 of her loyalty when he had absolutely nothing. 00:29:17.019 --> 00:29:19.420 That creates such a complex picture. He is this 00:29:19.420 --> 00:29:22.000 aggressive, sometimes toxic internet warlord, 00:29:22.099 --> 00:29:25.440 but he has this intense, almost mafioso -style 00:29:25.440 --> 00:29:28.180 code of loyalty to the people in his inner circle. 00:29:28.420 --> 00:29:31.980 That is the core of the Portnoy paradox. If you 00:29:31.980 --> 00:29:34.460 are with him, He will run through a brick wall 00:29:34.460 --> 00:29:36.539 for you. He will give you his credit card. If 00:29:36.539 --> 00:29:38.880 you're against him, like the union organizers 00:29:38.880 --> 00:29:41.420 or the pizza shop owners he doesn't like, he 00:29:41.420 --> 00:29:43.940 will try to publicly destroy you. There is no 00:29:43.940 --> 00:29:46.700 middle ground. You are either Ace Dooley or you 00:29:46.700 --> 00:29:49.220 are an enemy. So as we wrap this up, looking 00:29:49.220 --> 00:29:51.619 at the Fox Sports deal, the buyback, the incredible 00:29:51.619 --> 00:29:55.240 influence, what is the final takeaway? What does 00:29:55.240 --> 00:29:57.380 this all mean? I think we are looking at a new 00:29:57.380 --> 00:30:00.480 model of celebrity and maybe a new model of power. 00:30:00.619 --> 00:30:03.799 Yeah. Dave Portnoy proved that you don't need 00:30:03.799 --> 00:30:06.500 the approval of the traditional gatekeepers, 00:30:06.700 --> 00:30:09.079 you know, the legacy media, the HR departments, 00:30:09.180 --> 00:30:11.759 the cultural critics to win. In fact, fighting 00:30:11.759 --> 00:30:13.880 them is the business model. The opposition is 00:30:13.880 --> 00:30:16.180 the product. The opposition is the entire product. 00:30:16.319 --> 00:30:18.819 He proved that if you build a direct, unwavering 00:30:18.819 --> 00:30:20.740 relationship with an audience, you can survive 00:30:20.740 --> 00:30:22.880 almost anything. But now that he is on Fox Sports, 00:30:22.940 --> 00:30:24.759 now that he's a legitimate part of the establishment 00:30:24.759 --> 00:30:27.799 he used to mock, has he become the gatekeeper? 00:30:28.329 --> 00:30:30.970 That is the big provocative question for the 00:30:30.970 --> 00:30:34.049 next decade, isn't it? Can you stay a renegade 00:30:34.049 --> 00:30:36.170 when you're worth hundreds of millions of dollars 00:30:36.170 --> 00:30:38.369 and you're appearing on national broadcasts every 00:30:38.369 --> 00:30:41.029 Saturday? Can you still represent the common 00:30:41.029 --> 00:30:44.769 man from a $43 million estate in Nantucket? Or 00:30:44.769 --> 00:30:47.869 does the system eventually absorb everyone, no 00:30:47.869 --> 00:30:50.710 matter how much they fight it? It feels like 00:30:50.710 --> 00:30:53.890 he is trying to ride two horses at once, the 00:30:53.890 --> 00:30:57.390 outlaw and the mogul. The guy on the street corner? 00:30:57.799 --> 00:31:00.779 And the guy in the boardroom. And so far, somehow, 00:31:01.019 --> 00:31:03.519 he hasn't fallen off. Well, I guess we'll see 00:31:03.519 --> 00:31:05.720 if he starts censoring his pizza reviews now 00:31:05.720 --> 00:31:08.279 that he's on network TV. Knowing Dave, I would 00:31:08.279 --> 00:31:11.079 not bet a single dollar on that happening. That's 00:31:11.079 --> 00:31:13.640 it for this deep dive into the world of El Presidente. 00:31:13.640 --> 00:31:15.519 Whether you're Team Portnoy or not, you absolutely 00:31:15.519 --> 00:31:17.880 can't deny Len Impact. Thanks for listening. 00:31:18.039 --> 00:31:18.559 Stay curious.