818. - Pablo Torre

26:22But like some form of like celebrity psychoanalysis where you're also trying to check a fact that's clearly also an interpretation. and you're kind of like being like, I don't want to give you the line they used, but I do need to sort of ascertain whether you are in fact haunted by your parents' disappointment. Sure, sure. Yeah, yeah, yeah. Like, can we figure this out without me bumming you out and everybody walks away happy until the story comes out, of course. Can I prevent me, fact checker, getting a call from my editor being like, why the fuck are you preemptively undermining this story that we're about to publish?

26:57That's really funny. That's really funny. What a job. I just, I feel like that. Checker's going to check. I feel like that really used to be a job that was like, you got your foot in the door. That was a common way in, you know? It was the bottom line of the ladder. It was like, from there, much like the camera view that I got of Jason when I first logged on here, you were looking up. Keep sucking. You were looking up towards. It's the CAA or William Morris mailroom of publishing. Absolutely. Yeah, yeah. Absolutely. I guess at least you get to touch a lot of things. You get to see a lot of things from a lot of people.

27:28So, you know, at least it's that. At least you're getting to get familiar with several voices. Yeah. By the way, I have friends who, you know, tried to do the agent mailroom thing and they they they were they had voices foisted upon them as well. I just think it was less upwardly mobile, at least for me. Part of like the whole game here was if I could be so retrospectively cynical was like, I'm going to do this, but I'm also going to like pitch stuff. I'm going to be annoying in an editorial meeting. I'm going to say, I have an idea. I can tell you're annoying, so that's good to you. I'm glad you admitted that.

28:01Jason Stewart:You're going to be the squeaky wheel. Yeah. I think that unfortunately I've glamorized the Hollywood agency mailroom to the point where I regret not doing it, even though I know it's awful and I'm not really a glutton for punishment like that. But I do think there's a badge of honor you get from doing that, especially in the heyday. Oh, yeah. My God, what it would have been like. If only I could have been yelled at by Harvey Weinstein. Look, as far as things that Harvey Weinstein could do to me, I think yelling is the best case scenario. Touche. Best case. Yeah, but if he yells at you, then you might get that best supporting actor role, Chris.

28:45Jason Stewart:Yeah, exactly. Do the math if it's worth it. Do you think that now the fact-checking role has sort of been replaced by Grok? It sort of has been in my life. Yeah, I think anecdotally, it's funny that both of the sort of like sliding doors possibilities in front of me, I was going to go to law school probably was almost definitely the thing I would have. You fucked up. I mean, but but except except except for the fact that I believe rock or any of these LLMs, they are actively also just eating that. So anything that resembles like document analysis, I think, however overly confident these decision makers are about how we're going to replace humans doing document analysis with AI doing document analysis.

29:32Certainly, I think the first place you start is like, hey, do this immediately, actually. And yes, seemingly that's better.

29:41Jason Stewart:I wanted yesterday and they're like, OK, I could actually I could literally do that. I think I'm going to start saying when I'm reading a book, instead of reading a book, I think I'm going to say I'm analyzing this document. I think it sounds a little more profound. I'm analyzing and synthesizing. I am actually doing two things. Grok, I feel like Grok comes up a lot, Jason. Grok is only on Twitter, right? I think so. But you might be able to Grok outside of X. Can you? Grok outside the lines? Hey, Grok, can you Grok outside of X? The Grok thing, as far as I've never Grok'd outside of X, I've never Grok'd at all, I must confess.

30:21But part of like the kink of Grok seems to be that you have to do it in your timeline. Oh, you have to like see it. Okay, I see. It has to be. So others can, it's an exhibitionism of your most intimate inquiries, as far as I can tell.

30:35Jason Stewart:Yeah, but it is a nice little, and it almost feels necessary as AI images and fake news stories and fake everything is going on. It's nice to have that little grok at the bottom of something to let you know, like, no, this video is actually from seven years ago in a different country. It's not what happened last night or whatever. It's nice to know because our generation and older is pretty much unable to really tell if things are real or not on the internet anymore. Yeah. And we need the grok, unfortunately. Well, how do you use AI in your content creation right now? I mean, not nearly as much as I probably should, given how often I hear about people using it very effectively and saving lots of money.

31:24I have sort of like inadvertently with this show that I host, Pablo Torre finds out, I have a small staff of people instead of a staff of AI bots. And if they're listening. Oh, you don't say. You're old school. You hire human beings to do the work. I've unfortunately inefficiently relied on humans to simulate what it was like to be. Yeah. Someone who, I don't know, analyze the document in a way that took a lot longer. But in all honesty, the thing that it does help with is two things actually is like and I don't know how effective this is. So I do always have a human on the back end. Just like make sure.

32:07Hey, check this. Make sure it's good. But like translation, incredibly effective. And then, yeah, some form of like document analysis, aka, as Chris points out, reading, in which it's like, here's a 500-page PDF. Please pull out all the excerpts that involve this search term. And that has been helpful. Yeah.

32:30Jason Stewart:So no like illustrations for social media? We have a human. Assets. We have a human who does that, but I have played with it and have been therefore disappointed by it. I think you can get away with it and no one can really know the difference at this point. I don't want to claim like I'm doing farm to table podcasting or whatever the fuck. I just I just know that I have found it when I played with Mid Journey and I did for a while pay for like the monthly version or whatever. got enough credits to generate hey give me you know uh bill belichick uh you know on a dais you know wearing a tuxedo or something um it's not great it's just not not great at that yet what's up with your bill shit bro because i love i love that bill found love and you seem to be you know i i think it's nice i think if she's after his money he's got enough of it who cares it's making him feel young and and alive and you know his hymns prescription is hitting different nicole smith's situation yeah i mean it's elder abuse but who cares if if he's on board it ain't tricking if you got it look much much like i should i should conceive that much like the sport of football itself if you sign up for consensual concussions go with god like you're you're your kink is your kink i i truly there's no shame in this um where where it is fascinating to me and worthy of my, certainly not moralizing, but my raised eyebrow and, I would say, investigative journalism, is like, why is it that you were one way before and now you're the opposite now?

34:05What are the decisions that you make that are so different now versus when you were the coach of the Patriots, the head of the Patriots, and why? And that's where it's like, oh, now we're in that realm of interiority. It's very simple. It's very simple, and you're intellectualizing it. He was using his brain with the Patriots, and he's using his dick with this young chick. And those are the two things. That's the clear and present difference.

34:27Jason Stewart:So what exactly was it? What was he doing before that he seems to be contradicting now with his dickhavery? In the realm of dickhaving, Bill Belichick is a bit of an archetype. He was... No stranger to the game. Are you straight? I mean, look, I'm a dickhaver. I don't really... possession. I don't put labels on it. By the way, Chris, reminded to tell your dick story that you told me in between right before we were talking. Carry on, Pablo. Sorry. Put a pin in Chris's dick story for me. I also want to hear that. I believe... You have no idea. Well done, Pablo. Pablo knows exactly what he's doing.

35:08Jason Stewart:Sorry, go ahead. I always regarded Bill Belichick as frankly, a dick. He was an archetype of being... He was, in so many words, America's emotionally withholding dad. He was Mr. Do Your Job, Mr. No Distractions, Mr. I Will Bench, my best cornerback in the Super Bowl because he was doing something that offended our team culture. He was disciplined. He was Mr. Sun Tzu, quote, hanging on the wall of his office. He was just that archetype. And he was incredibly private and incredibly antagonistic towards the media and had no interest, actually, in being a public figure. He kind of lived in defiance of it all of this sounds so cool i gotta say first of all this whole personality is sick as hell and we need more of that and then you're saying somebody was like i bet you never had somebody suck it from the back and now exactly complete a full transform rewire the dna in his body all of a sudden all of a sudden he's changing the will that's how serious the smile muscles on his face were awoken after decades but but pablo as you describe his personality is kind of a no nonsense sort of leader, the reason people are okay with that is because he won.

36:23So you can be as much of a dick as you want if you continue to win.

36:26Jason Stewart:He'll bench the star player and he'll still win the game. Also, if you're from Boston. And he just pulled your chick. Yeah, Boston loves dicks. That's like what they're built on. That's the culture of Boston. They run on dick. They run on dick. Yeah, the center of the Boston ideological Venn diagram is its campus liberalism and its assholery is love of dick. It's a crazy combo, but I think that you're right. I think that really is the two things. As someone who went to school outside of Boston, I can personally verify this. Sure. I took the T in sometimes, but it was mostly in Cambridge. That's right.

36:59That's right. The thing about Belichick, though, is, yes, he was, by the way, this is the great man theory of sports, right? Like, you are the leader, and might makes right. You won. He was the, by the way, I bury the lead here, arguably. This is the greatest coach in the history of America's most popular sport. Right. And he won in that way such that everything got reverse engineered to be a strategy. Oh, I see. Like this might just be this guy's personality, but we've intellectualized and picked it apart as a strategy as opposed to just like an approach to life. He's just doing him. Fall is the perfect time to refresh and reorganize your space.

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39:05To Jason's point about like, you know, this rules. Yeah, this whole like doing him being a dick to the media. I'm not here because I am I am weeping for all the mean things he said to reporters and press conferences, many of which, by the way, I'm sure asked dumb questions. Yeah, that is not that is not the fainting couch I'm choosing to collapse onto. It is merely the idea that this guy was so aggressively one thing and was effectively, by the way, undefeated in press conferences in that way. He was weirdly he he was so uncharismatic that he became charismatic to that description. It was like a thing that people admired because he won, because he was so consistent with it.

39:45And because, again, tattered hooded sweatshirts, aggressively uninterested in. He's a style icon. I think that goes without saying.

39:52Jason Stewart:certainly so it's kind of like if uh if like adam sandler just started fucking a 24 year old chick out of nowhere and it's like it's cool i get it you're you're old you could do whatever you want but this is just something feels off here and maybe bill's like i worked hard my whole life what are you gonna do when you retire get my dick sucked by a 24 year old all day versus like i'm gonna pick up pickleball i think she's 27 and and i think that that i first of all the sandman is doing the same thing it's just on the low and i think that i think that bill i'm proud of bill for kind of being out and proud being like i'm an old guy getting taken advantage of and i don't give a shit who knows it so so to as a fact checker uh he is 24 okay my bad how dare you how dare you yeah okay 24 and how old bill 72 i believe he's 72 there's a gulf there between their ages, but I don't.

40:47But that's not the thing to me. I look, I'm with you guys. Like, I'm not here to yuck their yum. I'm whatever. Like, that's not the first relationship with a vast age gap. It's not independently interesting either, even if it is funny, objectively, for reasons that the math would indicate. What I am saying is that when Bill Belichick, to Chris's point, when Bill Belichick stops winning and he is no longer allowed to remain the leader of the New England Patriots and he is effectively thrown out of the NFL, he has to figure out what am I gonna do with my life and it turns out that he had met Jordan Hudson as I and I this is something that I self-loathingly but proudly say as I exclusively reported Jordan Hudson was 19 years old on the plane that they met each other there's more in that episode that I why was Jordan why was Jordan on the plane though so Jordan was on the plane to meet her then boyfriend who was I believe in his 60s at the time these are just facts not judgments who was in Palm Beach She likes, you know, they're headed to Palm Beach on a JetBlue flight.

41:48Bill Belichick flies JetBlue.

41:50Jason Stewart:I mean, what's the median age on a Boston to Florida flight anyway? It can't be sub 50, right? I would say that, yeah, you know, Jordan Hudson is a dot on one side of the graph. You're saying that this wasn't a private flight? This was a JetBlue mint? So despite, this is a good question. Despite the fact that Bill Belichick was making 20 or so million dollars a year for years and years and years. Yes, he flew direct Boston, Logan Airport to Palm Beach, Florida. He would go to Jupiter and play golf at the Trump Golf Club there. And he was a guy who flew JetBlue. No judgment either. Just facts. He flew JetBlue Mint.

42:26Correct. And that's where he encountered in the seat right next to him. In a meet cute that Bill Belichick's family, I can also tell you, does not believe to be random, even though I have no indication that it is anything but. So you're saying she's sitting next to Bill in their 1A, 1B in JetBlue Mint, and maybe he's fiddling with his phone. He can't get the font size large enough. She sort of sees her opportunity to reach in and help him start a conversation.

42:54Jason Stewart:She's in 7C. She switches with somebody. Oh, I spilled my drink. We moved the boarding passes. I don't know. This is my seat. And then boom. Yeah, I just think that you're right. Maybe the whiplash of his sort of change in direction is what people are more interested in than him actually. I mean, we'll always be interested in an old guy and a young chick. That's the American way. True. True. But it's even more than, I think, outsiders. The reason why this story kind of popped onto my radar in a really blinking, like, holy shit kind of a way is because it was the people who know and are physically, emotionally even, closest to Belichick who felt that whiplash most acutely.

43:34And it is people in the Belichick family. It is people who worked for him, people who are at. You know why, Pablo? You know why, Pablo? Because they saw their money dashing. They said this will is going to get changed. Everything is going to change. Tale as old as time. Everything is going to change. We have to get this bitch out of here. That's what they were saying. So on top of that, which I will not take the time to refute, on top of that, on top of that, it is also the fact that this was making him look like a laughingstock. Well, that's true. And what he did, I mean, and this is getting to, by the way, so to speed run through a bit of that flight, just because I think you guys would find this amusing.

44:09So she is sitting next to him. She brings, she is a philosophy major, and she has her textbook on deductive logic. and so there is an inscription that Bill Balichick wrote to Jordan Hudson in the you know front cover of her philosophy textbook and it's dated and it's signed and it is you know Bill Balichick Hall of Fame blah blah blah eight rings and so forth and so forth and so forth and so forth and so that's it's that's how we know is that there is this artifact so he gave her a Jeter style post smash gift basket kind of but in in a signature of of her textbook a little something

44:46Jason Stewart:I'm going to show the grandkids. Hold on. To be clear, Bill Belichick didn't write this textbook. It was just a surface for him to autograph. It was written by a Harvard philosophy professor, actually. Okay. All right. One of your guys. The type of show I do, as a pure side note, is the kind of show where we went and interviewed Professor Warren Goldfarb, the author of the book, to know, like, did you know this? Did you know anything about this? And he's kind of hilariously himself proud that he was like a philosophical aphrodisiac for the relationship that I believe America is obsessed with. Wingman.

45:22Nothing gets a guy that hasn't been hard in 20 years going like philosophy. You know, that's like, I guess maybe seeing Tom Brady with his shirt off at certain times probably worked. But this worked better. Well, I believe that some part of this is like the Brady thing. I mean, there's just so many ways to like further drag you into this sort of rabbit hole with me. Because hold on, do Brady and Belichick have beef or are they good? They have become better in recent years. But one of the key moments here is there's that Netflix roast of Tom Brady, which is live and, you know, globally very, very well trafficked, it seems.

46:02Very popular for Netflix. They're going to do a zillion of them now. Belichick's on stage. and Brady is like roasts when he gets his turn at the end to like, you know, roast back. He roasts Belichick over Jordan Hudson and makes this joke that prompted me to do another thing on my show. But he mentions Brady says for a long time, whenever I got asked the question, what's your favorite ring? I would say the next one. But now I have a new answer. It's that ring cam video of a shirtless Bill Belichick walking out of that poor girl's home. And for those not familiar with the lore, there was a there was a there was a viral video from a ring camera that got circulated on the Internet of a shirtless.

46:46And I would say and stand by this description, a Zoftig Bill Belichick sort of just like wandering around on the porch, kind of like dazed and confused like a bear and very hairy. and that just became like a what it what? Yeah, we've never seen Bill Belichick with post-nut clarity. This is the first time in history we've seen that. It was an intimate view.

47:07Jason Stewart:But you're saying Bill was built like a Coca-Cola bottle is what you're saying. He was - Yes. He had titties, hips, and ass on him. He was working with a monster and he had some nice little titties on him too. Yeah, he was working with a monster. I don't have my glasses on. Is that Saweetie? Oh, that's Bill. Okay, sorry. Babe, can you give me my readers? I can't see. Wow, that's actually, but this story continues until they break up, basically. People won't leave this alone until Bill leaves her or she leaves him, is Maya. So they are now enmeshed professionally. So what happens after he gets thrown out of the NFL is that he starts, he does this.

47:49He starts a podcast. He has a half dozen media ventures. Again, the guy who hated media becomes a media guy. tries to, tries to, to avoid being labeled exactly what Chris just labeled him because he's the greatest winner. And now he's to figure out, like, what am I going to be? And so he starts to do the talking to a microphone thing. And the COO of his production company, which, of course, is a funny thing to imagine, if you know Bill Belichick from his days as a coach, his production company is Jordan Hudson. And she's functioning as his agent. She is the person on set. Because that's why she stepped in during that interview and made them stop, and then it was on camera and people lost their fucking mind.

48:29Yes. So this is all explaining the CBS Sunday Morning interview, which is also a hilarious, for anybody who's fluent in media. Unbelievable. The funniest possible scripted set for that interaction is CBS Sunday Morning. One of my favorite and crotchetiest kind of TV programs, like she didn't know what that was until she was there stopping the interview oh yeah but just the idea that like there will be you know this is being thrown what she didn't appreciate maybe is that gail king is gonna throw to this as like a bird is chirping on the you know the music bed and this is like the puffiest piece that she could have hoped for and instead she doesn't want to tell the story that i've obviously begun to tell you about like how they met and all that stuff and that becomes just the most public window short of i would say the reason i started looking into this, which was the Super Bowl commercial.

49:20So this year, you may remember this as connoisseurs of excellent brand marketing. Dunkin' Donuts does the Super Bowl commercial, and it's the Boston Avengers. How could I forget? How could I forget? Yeah, the Boston Avengers. How many racist guys can we get in one commercial? It's the Boston Avengers. How many guys with Wikipedia pages we got to scrub? Can we get into the same jumpsuit? Before we can get this going. No, so it's them. It's the Dunk Kings, right? And it's Affleck and Damon, and both Afflecks, actually, and Damon. And I had learned that the person, and so they want to book Belichick.

49:54And the person that Affleck and Damon needed to go through to get Bill Belichick, the favorite coach of their favorite football team, is, it turns out, this Jordan Hudson character. I do not want Ben Affleck calling my chick for any reason.

50:09Jason Stewart:Who was probably 22 at the time. I'm sure Affleck and Damon have children older than this person, and they have to go have a meeting and say, is it OK if we talk to your boyfriend on the commercial and give him eight million dollars for a half an hour of work? Well, and what she's like, well, what she says as she, you know, Birdman hand rubs is is actually actually I, I, Jordan Hudson want to be in this thing, too. And so if you go and watch the commercial, she's standing right next to him. And that's when I was like when I was watching the Super Bowl and I was like, is that because I'm like, you know, a creature of the Internet who's like paying attention to these details in ways that are unfortunately clinical at this point.

50:48I'm like, is that is that is that Jordan Hudson? And it was. And that's why I was like, how did she get in this? And then you hear about how she's been his agent behind the scenes. She's the person, the membrane you got to deal with to get to Belichick now. And that was true of literally the height of Hollywood had to go through her. And so that she would do all this other stuff, insinuating herself into would-be commercials and sets and tapings and podcasts. Putting yourself in the commercial is crazy work. It's a real heat check.

51:17Jason Stewart:So she's sort of diddying, I guess, where if you don't want your producer to be all in the videos, all the Duncan commercials come to death row. So I guess the other, to understand where you're coming from more, it's clear now, but I'm sort of using Alec Baldwin and Hilaria as a comp as well, where it's like, obviously Baldwin has had a few snags, murdering someone accidentally, et cetera, et cetera. Allegedly. Going off yelling at his kids and stuff. He got off on that. You know what? Don't do that, Jason. He's free. His name is clear. Free the guys. Free the guys. Diddy and Alec Baldwin, both very free individuals that you've just named.

51:56That's true. You're forgetting my personal favorite, Kevin Spacey. Walking free.

52:00Jason Stewart:Okay, well. Walking free. Well, then we're putting Belichick in this category as well, where you've got this legendary kind of stoic king, does exactly what he wants, and nothing that he doesn't want to, says fuck you to the press, is outgoing, outspoken, private, whatever he wants to do, he only does that. And then his legacy is sort of ruined in the 11th hour, in the fourth quarter of his life by a psycho chick. tales all this time. And now he's got to do a podcast and a TV show and a this and a this and a book and a cookbook. Well, so what he then goes on to do after the media stuff is a failure.

52:38It's not good. It's, in fact, by everybody's account who worked on these things, it was disastrous. And she was a big contributor to that for whatever it's worth. He goes and becomes the head coach at the University of North Carolina, the highest paid public employee in that state. But I want to return to the comparison you made, Jason. Go Heels. Because Hilaria is, I think, kind of the best parallel as I've been like surveying the world of age gap relationships. Because Hilaria Baldwin is somebody who does not want people to know her actual deal. Yeah. I feel like that's journalistically sound to say.

53:13Like, is she Spanish? Is she? I think I believe in a twisted bit of fate. I believe she's from Boston. Hilaria. That's why her Spanish heritage was in question Because they're like, bitch, you went to Nantucket In middle school every summer We don't do that over here

53:35Jason Stewart:Hilaria Baldwin, born in Boston, Massachusetts All roads lead back to Wustat She's trying to sell you on the Enya word And you're like, no, we know you're real You're a real deal We know you're real I also wanted to talk to you about Because you did the thing that A lot of journalists do Where you write a story and it becomes a whole thing and then ESPN, you know, buys it from you basically to make the television version. And I think a lot of our listeners would be interested to know like what that process is like and how lucrative it is or is it more of a for exposure type of relationship? Yeah.

54:13Are you referring to when I was at Sports Illustrated, I wrote this story called Broke or How My Athletes Go Broke? Yes, yes. Because I saw the, I didn't, obviously I didn't know you then, but I remember watching the 30 for 30 and it's a great story and it's something that you heard whispers about forever. Yes, yes, yes. Like those facts, that's a known thing. But I think that the process of taking that from a Sports Illustrated story, how involved is Sports Illustrated? How does it work on the back end? So this is a really funny question that no one has asked, but has, I think, a lot to it, which I am actually very excited to just sort of describe for people who are curious.

54:52I should preface this by saying that I am now friends with Billy Corbin, who's the director of Broke, who's done Cocaine Cowboys and all this other stuff. And he's terrific. Yeah, yeah. But what was very funny was that, so I write this story for Sports Illustrated called How and Why Athletes Go Broke. It's a 5 ,000 word story. It's in fact the story I had been pitching as the annoying fact checker in that story from before where I was like, I got something for you guys. And I'm like repeatedly just like chipping away at this thing in the back, sort of on the back burner.

55:17Jason Stewart:Buzz off, kid. We got female lacrosse on at three. Yeah, exactly. Sound of typewriter clacking and I am like thrown out of the office. That's truly like more or less what's happening. But I provide this thing and I've exhaustedly reported it and it becomes like one of the most traffic stories in SI dot com's whatever, like tortured online history such that at a certain point I hear. I think far through the production process of the 30 for 30 documentary, which would become broke, that my story was being adapted. So I was not consulted on the front end. I had no idea. I was, frankly, kind of like aggrieved.

55:56When I heard about this, I was like, what the fuck? Like, this is clearly based on this thing that I toiled on for less than$40 ,000 a year. This was something that I, this was like my only baby. Y 'all got to break me off something. I'm barely getting by. Y 'all got to break me off.

56:11Jason Stewart:You did good, kid. Give us another one. What else you got? No, so it was more or less, yeah, it was like that. And at this point, this is now getting into 2012. I'd written the story, I believe, published in 09. And so by this point, as the production process is proceeding apace, it becomes clear to me that Sports Illustrated was not involved at all. I was not involved, clearly, at all. But 30 for 30 was really excited about this. And Billy Corbin was directing it. And it was funny because I remember there were two things happening at the time when I was eventually asked, would I want to sit for this documentary about this story that I had written, which was, again, an insulting premise.

56:54Yeah, I would actually. I have a lot to say. Yeah, yeah, yeah. How much time you guys got? But it was number one. I was, and anybody who's made a documentary knows this. At a certain point, you bring in the talking head journalist for exposition. Where it's like, oh, we got to bridge this thing between these two things. And we need someone to say facts. Let's get one of these fucking nerds in here. Let's get one of these pencil pushers in here to let this thing move this thing along. I realized, oh, I'm playing that role here. so I can see the utility of it. And also, it made clear why I was being brought in towards the end, was there are some holes to fill.

57:31So you're saying to me that you're not involved in this at all. They basically take your story, turn it into a 30 for 30. At the 25th hour, they call you to fill in some blanks, and you're like, fuck it. I'll do it. Well, here's the second thing that was happening. I don't think that this was at all coordinated, but parallel to this in 2012, where I am in my career is that I'm simultaneously being offered a job at ESPN. And so I'm being hired to work for ESPN the magazine and to do television for them, which I would do for the next 13 or so years. And so what was funny was that what would have been like a real soapbox of grievance for me to climb onto and perhaps litigate.

58:14I can't fuck up my new gig. I was like, my new gig. I'm actually going to get broken off something. And so I was actually quite happy that I got to whatever, like get paid and get a new job and also make them happy on the film side. And 30 for 30 was good to me after that and all that stuff. But wasn't great on the front end, admittedly. That's actually I didn't know that was I mean, I guess it makes sense because technically Sports Illustrated owns the story. So they don't have to ask you for shit. But usually people want to go about it the right way and at least like have the blessing.

58:43Jason Stewart:They were nice enough to throw you some lube before they fucked you. That's crazy. That's a crazy story. Not everyone gets that. It's a crazy story, but I guess it worked out because, like you said, you ended up having a long-term relationship with ESPN. It was sort of like they lubed me up on the back end. Let me use this as a teachable moment because there's a lot of everybody's stealing from me vibes on social media. And I think that maybe our generation is a little bit like, at least me personally, I'm like, no one's ever ripped me off because I've never had an original idea, neither have you, is kind of the way I look at it.

59:17Also fair. But I like this. I like that you had the sort of foresight, whether it was on purpose or not, to be like, you know what? This is not worth it because there's something bigger for me in the next year and I'm just going to hold the line. And it worked out. I think one market inefficiency, which is very perhaps unsympathetic to advocate now, and maybe we have the luxury of having existed long enough to say it, but you should play, perhaps true to the name of your show, the long game. Like, I'm not like, I guess I could try and like get whatever I can now and burn a bridge or I can see if I can use that bridge to get 25 grand from ESPN one time and feeling good is not as good as being on TV for 13 years and cashing those checks.

59:59Yeah, I would have, you know, a Twitter thread in which people feel for me. But I'd rather. But I think that's what a lot of people are looking for. And that's what's fucked up about the times we live in is that like it's it's about that instant gratification. And I mean, I'm guilty of it, too. Oh, no. But I think about this. You know, there are lots of it's funny to see the world through this lens, because. And again, now working in independent media, as you guys do, the question is, like, how do you gin up public reaction or sympathy or, frankly, money? and the whole thing of like can I be and again god I sound like fucking a real bootstraps immigrant parent now but the question of like how can I be the sympathetic victim in a story it's like yeah I guess what happened to me at my media job it's like you can do that at lots of moments I think every day I read that every day I read how unfair this industry that I chose is to me because I'm not good enough.

1:01:01Maybe it's because I came up again huffing the exhaust pipes of Black Town cars outside the Time Inc. building but like yeah we chose this like there's again consensual concussions right like we signed up for this part too I was not promised anything but feeling embittered frankly. All I looked at was people feeling embittered.

1:01:24Jason Stewart:Well you chose it because it's the only it was the only path out and into what you wanted to do back back in you know 20 years ago same thing as you know the only way to become famous is get a music deal or signed to whatever and now thanks to independent content creation we can just if you're an ip machine and you got a new story every week why give it to some other company and maybe they're gonna fuck it up blah blah blah they don't care as much as you do you can hire a few of your friends get a little get the grok fired up and you're doing the whole thing yourself and if if the ip goes then the ip is yours i wonder if the i wonder if those stories are being mined on sub stack the same way they're being mined from like new york magazine or gq you know you know what i'm saying i wonder i'm sure if that's happened yet because i don't think that sort of the problem with sub stack one of the many problems is that it's not that it's not really a home for some of that rigorous reporting that's not what it is it's more of like a journal and it's that that stuff is less valuable as far as ip goes i think then then sort of this the stuff you're talking about i think it's changing i think that's the original sort of feel for it but i think now there's a little bit of everything oh there's definitely no there definitely is i just i just mean that like there's no like history of this so it's going to take longer is what i'm trying to say like the the history of like we optioned a a book or a magazine story for a movie or tv show is sort of like how the the ship was built and now there's this new thing where it's like a little bit harder it's honestly it's probably harder because you have someone that's independent that thinks that they're god's gift to the earth and they want a hundred million dollars whereas you know espn was probably or sports illustrators probably yeah give us 20 grand we'll make it work so oddly enough and i'm sorry you talk pablo oddly enough go doing the the new york magazine story for a thousand dollars is playing the long game compared to putting it behind a paywall and making 30 grand a month on Substack and not having it turn into a big book deal or a movie deal or something.

1:03:28Well, so you just went where I was gonna sort of like go, which is the trade-off between paywalling and not is always just about like, do you want, again, they call it the funnel. Do you want the potential audience for your shit to be as big as possible? Or do you feel comfortable with the audience who've already acquired to just give you money directly, which is why my very, I would say, I would call it my decreasingly original theory of the future of media is simply that we're all OnlyFans. And the question is like how much longer you want to fight that before you just realize I have X people who will give me Y per month, which is more than they would pay, by the way, a publication, which offers many, many multiples of tonnage of content.

1:04:14I don't even have Wordle on my shit. Not tonnage. Not tonnage. Yo, bro, they offer hella tonnage over at the New York Times. You're right. You're right. Yeah, no, you're absolutely right. No, but that's it. And so it's just sort of like, you know, which now speaks to the incentive structure, which we were just describing, which can be unfortunate, which is support me because you can basically hear the Sarah McLachlan underneath my words. I need you to live. and that can create an incentive structure that is perverse and frankly inimitable or in inimical perverse both ways but in both in both ways it is not what uh and how i came up through whatever not to sound like uphill both ways to school but like no no no i mean i think it's i think you're absolutely right it's it is like a choice you make like do i want the most possible people do i want to convert people or do i think that the dedicated the few the proud are enough

1:05:08Jason Stewart:to keep going am i willing to refuse some loads or is it no loads refused exactly no exactly i mean and that's what i i just don't think that um i don't know i i i pay for a lot of stuff but then i don't expect anyone to pay for my stuff which is my own twisted kind of head you know but i think that that's just like how i am and i've stopped fighting it you know i recently i the reason i I am speaking to this so perhaps passionately is because I recently had this decision, Chris, where I was like, I have a sub stack. It's basically a newsletter where I say every episode of my show, which three times a week, I send you an email and it's like, this is what it is.

1:05:47And here's some like behind the scenes things, blah, blah, blah, blah. And at a certain point I realized as I am in this independent Hobbesian, you know, like whatever state of nature, like I should just turn on, I should do the thing that people have advised me, which is turn on the paid option. so see what happens exactly so if people just want if people already feel sorry for you let them give you money like literal patronage it's sort of like if they want to please sir i need to pay my midtown hoa fees please sir i live in a co-op building yes is more or less but i think

1:06:23Jason Stewart:i think that's the best way to do it versus the restricting stuff and you know like you're only going to hear five minutes of this podcast. If you want to hear the other 55, you got to pay. I think the way that you're doing it is the way that I think is the best way of true patronage. If you really believe what I'm doing and you want to support it because you're a good person, boom. But let's leave that funnel a little more open. But you're also offering something for the heads. If there's behind this, that content is specifically tailored to people that really care that in theory would want to pay.

1:06:59And I need to figure out, by the way, this is also just a reminder, like, oh shit, I should like figure out what am I giving people who like become a founding member? You know, like I say in a sarcastic voice, but I need to become very earnest about because I should deliver on that.

1:07:11Jason Stewart:You're going to have to start doing cameo birthdays first and foremost. Honestly, I'm not above it. I am not above it. That sounds pretty, that sounds like efficient, relatively speaking. Okay. But the other thing, which I should be frank about, which is like the other reason to do it a synonym for like keeping the funnel as wide as possible is also like the vanity of believing my shit should be appreciated by those who are not already in my audience so like please come and check out what i got i think you'd like it and so the more that you paywall your stuff the more that your garden is walled you know i i don't want it to be you know so much of a secret i would like i use an accidental secret garden illusion but i would like you to you know actually just come check it out.

1:07:53So there's just vanity also in just the desire to grow. Totally, dude.

1:07:57Jason Stewart:I wouldn't call it vanity. I would call it discoverability. I think it's just, you know, you're not doing anything particularly vain. I didn't know you worked at Spotify now. You got it. No, I mean, it's not. You got something you want to tell me? You're doing a general interest show that can appeal to a lot of people. If you're not talking about slices of life, you're talking about sports. You know, it's for everyone. A liberal arts version of sports is how I do it, which is like we'll talk about, you know, if you've listened to me talk enough on this episode with you guys. I listened to the bird watching episode this morning.

1:08:28I appreciate you doing that. Thank you. I didn't listen to anything. I think that you're great. I think that you what you're doing is much, much more appealing to a wide audience than like what we're doing. You know what I mean? I think like truly. Not with that attitude. No, but I just think that it's just two different things. It's not like we have a pretty wide audience and we're happy to have it and hopefully it continues to grow. but I think that like you're right a liberal arts approach to sports that is a that is a huge swath

1:08:55Jason Stewart:of society which is which is why when I sorry for interrupting when I texted my brother hey do you know Pablo you know let me know whatever he sends me a screenshot of my text on his phone while he's listening to your podcast so you know that answered it and he is I love it in terms of Liberal sports enjoyers. My brother and I are there for you. No, look, it warms the discoverability of my heart to know that. It's also genuinely, when it comes to sports, right? What's my thesis around sports? Why is it something that I started off kind of like reflexively being like, am I apologizing for being in the toy department?

1:09:34Am I like trying to make this sports for non-sports fans? I just realized that at a certain point, because everything to even further sound like a PowerPoint deck at Spotify, because everything is so fragmented and siloed and because nothing is discoverable really anymore because search is broken and Twitter deactivated links or whatever the fuck else. Sports is just this. And I say this all the time. It is the closest thing we have to like anything vaguely monocultural. And so if I can use these characters that you may be vaguely aware of as if I'm, you know, Disney rebooting the Mandalorian, like, hey, you know, you heard of this thing?

1:10:07Here's another thing you might enjoy. Well, like, that's something that I should probably strategize around as opposed to, like, apologize for. I mean, the Bill Belichick, I don't give a fuck about football, but I know all about that story. Because it is like a general interest in a lot of ways. And if you want to follow some of those threads, I'm sure you can get deeper into it.

1:10:25Jason Stewart:Yeah, when I was listening to the bird watching episode, you know, you probably had a dozen sports analogies in there. You know, a dozen, you know, this is your Jordan v. Bird moment or whatever it might be. I just made that up. I was going to say, I should have used that, actually. that's a real mistake it seems like the most popular podcast or any media thing is the sports analogy is going to move the most needle or move the most chains I should say. There you go Jason Jason said I'm getting on board with this shit. He is pantomiming throwing a football and it's two more quick questions before I leave you on that specific subject and I was thinking yesterday, I was listening to your pod doing a hot girl edible walk and I was thinking about our podcast about like what exactly Chris and I talk about and it's a little slice, you know, it's like where we went to lunch and then like gay fashion stuff and, you know, a little bit of this, a little bit of that.

1:11:28Jason Stewart:You're doing a show about sports and then I'm thinking about like, you know, political podcasts or like at the top news, that kind of stuff. I wanted to have you rank podcast subject categories by average income potential. Oh, wow. Wow. I mean, I don't need 10, but maybe - No, well, are we talking - Let me take this question very seriously. Are you talking audio only? You're talking about video podcasting because that informs my draft picks. I'll stick with audio only. I would say that something that I have not done enough, but I'm tempted by as I also I'm doing like a bunch of political news stuff at MSNBC and I've become a creature over there in that ecosystem is like, man, I I should preface this by saying I don't like Donald Trump.

1:12:14But I think I am incentivized to really, really, really express that way more often than I do already. I just think that in terms of the lane, like something that I laugh at all of the time is the whole like Joe Rogan needs to the left needs their own Joe Rogan. And I'm like, oh, oh, OK. So what does that involve? And I'm like, so you want someone who's going to say politically the things that are validating to the left, which, again, I naturally am probably going to do intuitively. Not all ways, but often, I guess, statistically speaking. But then it's also like use sports. And you like, do I just like lead with MMA, but then backdoor just like, but here's my thing about the big, beautiful bill.

1:12:57Jason Stewart:Well, we always actively try to become the Joe Rogan of the left. The basic rule of thumb is say fuck ICE, say fuck the police, but also call people gay. You have to really swim in both waters. And they're like, okay, I could deal with this. You know what I mean? Yeah, what I'm saying is that the podcast category that is most profitable for me personally that I have yet to seize upon is just like, what if I podcasted like I was still at my all boys Catholic high school? I feel like that's actually the demo that the left needs. And I'm also happy to call things gay if it means I'm saving gay people in real life.

1:13:35Damn, when you look at it like that. Well put, Pablo. That's pro shit right there, Jason. That's why we're not on TV. That's why we're not on TV.

1:13:41Jason Stewart:I led this prize horse to the water. Pablo took a big old gulp. Pablo, he put a little in his little satchel for me later. He's a nice guy. And last one, and then we're going to leave you on this episode. And it just reminded me, you hired a vocal impersonator off of Cameo to do an impression of David Attenborough. And I wanted to know if you've heard the David Attenborough. very there's some tea about his life and legacy that is very bad and i want to see if you knew about it oh wow don't ruin his fun don't ruin his fun it is real wait hold on as someone who paid untold hundreds of dollars for a guy whose name is guy on cameo to be david adenborough but you gave you gave him a shout out you should have that should have been pro bono i have a lot to learn from you guys now that i realize uh let me be your manager not a bad idea let me be you did the right thing by paying an independent creator.

1:14:35Okay, at the risk of finding out something at the end of your show, which is a real reversal of fortune for me. What has he done? Okay, you know the... Also, hold on, hold on. We need to be clear. This is all hearsay.

1:14:48Jason Stewart:This is rumor. I have no proof. This is just... I've heard it from a couple people. If Sir David Attenborough was listening, I am merely absorbing. I am not cosigning. Of course, of course, of course. Apparently, the BBC is aware of Attenborough having a Jimmy Saville-like situation and they're waiting for him to pass before the story becomes public. Whoa, whoa, okay. I mean, you don't have to comment on it. I was just like, oh, I wonder if he's heard the story because I've heard it from a couple people. As somebody who has now very subtly Wikipedia'd Jimmy Saville while you've been saying that, I'm going to store that away in the old mental Dewey decimal system.

1:15:33Jason Stewart:How long gone listeners can Google what did Jimmy Savelle do wrong? Or I think there's a Netflix documentary on it. Well, I think to summon the term tonnage, it does apply here in a way that well, well, well, well observed. Good to know. Good to know. Thank you. Just something to think about. Copy that. Something to think about. Pablo, thank you for joining us. And your show, you said your show is three times a week? Three times a week. Impressive. welcome to the club brother we love that welcome to the club yeah for sure uh thank you for joining us it was a pleasure you guys go uh listen to pablo's podcast pay for his services whatever those may be follow him on substack yeah um we appreciate you taking the time you're a good podcaster the time just zips by with you so we'd love to have you back on again one day anytime i i listen to you guys and it's funny to go from parasocial creep to participant so So thank you.

1:16:32Yeah, participant creep. Yeah, it's great.

1:16:35Jason Stewart:As long as you listen to the ads, nothing creepy is going on at all, Pablo. I don't give a shit what you do. Let me tell you guys, the Pablo Torre finds out promises that I will always listen to your ads. Thank you for that. That's a big, and that's a nice cosign. We need that from you. Even the DraftKings ad? Especially. Especially your incredibly credible DraftKings ad. He's like, I need a little hit of DraftKings. I can't do it myself, but I need a little hit. So I want that old thing back. All right, Pablo. Thank you for taking the time. My pleasure, guys. Time tests fell on you But you won't forget me

1:17:16I know I could have loved you But you would not let me

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