The Ryen Russillo Podcast - Nick Bilton on 'American Kingpin' and the Silk Road. Plus, Mailbag Life Advice | The Ryen Russillo. Podcast

Episode Date: May 14, 2020

Russillo talks about Scottie Pippen's refusal to check-in during the 1994 playoffs versus the Knicks (3:50), before talking to author of 'American Kingpin,' Nick Bilton, about the Silk Road, an Amazon-style internet marketplace created by Ross Ulbricht that featured illegal drugs and other items. They talk about the rise and fall of the Silk Road, Ulbricht's capture and trial, and more (13:09). Finally Russillo answers some listener-submitted questions (47:25). Learn more about your ad choices. Visit podcastchoices.com/adchoices

today's episode of the ryan rossola podcast on the ringer podcast network is brought to you by state farm just like sports the game of life is unpredictable talk to a state farm agent and get a teammate who can help you navigate the unexpected i I feel like every time I do these, they're not unexpected because it is not unexpected to see baseball fight over what is sort of a on the fly takeout CBA. They did agree to something in March. The parameters have changed. I'm leaning player on this one because I feel like the owner's going, Hey,

let's just do like a salary cap version of this for a season and see how it goes. There's no way that was ever going to work. But I also think the players should feel some of the losses losses which they would in a prorated salary thing but i'm i'm more pro player on this one and i really hope baseball can figure this out because they need to get on the television for everybody to see um because i think it's important to baseball i'm not talking about selfishly wanting to watch baseball i just think it's really important for baseball because the fallout of baseball doesn't have a season and then the NBA does come back, which

feels more positive today than it did Sunday. If baseball doesn't come back at all, it's just as if baseball doesn't deal with enough criticism, fair or some unfair. I can't even imagine if they just missed the whole season because of a CBA. Again, it's not a normal CBA negotiation, but a CBA on the fly.

Yes, the players should have to take some of the hit, but the owners, I don't think, should be trying to pass mechanisms that are basically non-starters in any negotiation with the players' unit. Get a teammate who can help you navigate the unexpected. Talk to a State Farm agent today. So here's the plan. We're going to do a mailbag that'll be fun at the end. We're going to talk with Nick Bilton, who is the author of American Kingpin.

That is the story about a guy named Ross Ulbricht, who started Silk Road. I didn't know anything about Silk Road. Kyle, did you know anything about Silk Road? I did, actually. When I first came to California, I was trying to get someplace like Silk Road. I found a different website, but I was interested. I was very interested. I reported on it in college and stuff like that. Oh, you did? All right. So it's all research-based. That's good to know for the potential employers out there. Yeah, Silk Road was a dark web version of Amazon for drugs. And the story's incredible. And I can't wait to talk to Nick about it. I also want to do a little bit on Pippin, but first I have really good news

that I want to share with everybody. Those of you that have been following me since ESPN, a big reason why I wanted to leave the radio show was that I wanted to pursue writing, and I've signed a production deal, a script deal with ABC Studios, and it's the next step in the plan, and hopefully I can put together something great. And great and so yeah i signed a deal with them so i was only away from disney

for a few months and i couldn't be happier to be back with them and i want to thank johnny davis at abc there's a bunch of other people that i need to thank but i also need to get to work on uh on what i'm helping develop uh certainly not guaranteeing anything anybody that understands this business knows how hard it is, but at least like the next step is there. It's official. I guess I am a writer and I'm excited about it. And I really want to thank my guys at ICM,

Ted Shervin and Michael Charney, because without agents that believe in you, instead of agents that just tell you, yeah, that's a great idea. Never follow through. These guys believed in me and I told them from the get-go, I go, the sports thing I have, I got it. But I go, I need your help on this, but I have to know that you guys are into it

and you believe what I'm doing. And I'm sure they probably did a little bit of a, let's see. And then they read my stuff and they're like, you know what? There might be something here and get a few scripts out there. So there's some other stuff I'm also working on with the writing stuff, but that's the first official one. I don't know when the announcement is supposed to be happening soon. So I'm just going to go ahead and make that announcement here on the podcast. So I'm fired up. Okay, let's talk Scottie Pippen. This is not me freaking out seeing Pippen ranked ahead of Barkley on the ESPN.com list.

I'm not really upset about the ESPN.com list because they named, I think it's the top 74 players. They got stuff to do, man. They got a website. They got to fill with content. Getting really freaked out about it. There's some where you go, that guy's probably a little high to be this young, or maybe a little too young to be that high.

Some of the younger guys, it just feels like, well, what do you do with Giannis? I mean, Giannis physically and statistically, if he keeps doing this for another 10 years, without the rings, we're going to have a problem with it. But if he gets a couple, we could be talking about one of the all-time greats, but it still seems premature to even do that. And they had him, I think, in the top 30. Can you double-check that for me, Kyle?

Barkley behind Pippen is infuriating. There's zero. I don't know what stat you would find that you would think that Pippen were better than Barkley if you're just doing six rings to zero. Okay. But I mean, Pippen is not the reason the Bulls won six rings.

Steph being top 15. I don't know what you do with Steph. I mean, his resume as of right now and the way he absolutely changed the way the game was played offensively. We all know I'm pro Steph, but it just starts getting really hard. Like when you start figuring out, wait a minute, can I get to 40 guys before I got to Isaiah Thomas? That doesn't

seem right. I personally wouldn't do that. I always think Isaiah is incredibly underrated, but the reason I even bring up Pippen isn't because of the Barkley thing, which is funny because the Barkley video that I did about Draymond, Kyle, I didn't even know that was going to become the video. So part of me as I watch it get picked up a little bit and it wasn't like it was some massive massive deal I almost wanted to tag when he's gonna be like hey just so you know like I just sort of did this off the cuff this was not some big planned out open this wasn't some thing where I'm like now it's on your Wikipedia page I'm gonna I'm gonna blow your minds Charles Barkley is better than Draymond Green next um

yeah I mean it's just it was the thing where I'm going wait a minute and there were a few blue checks doing it so I'm not guilty of the straw man on that one but it almost was too produced to make me feel like wait a minute is this we're still thinking some pioneer on this Barkley's better than Draymond take what's next ice water is better than room temperature water. I know right now too, somebody's going to be like, actually, actually fat burning cells, you know? All right. So let's talk about Pippen and not going back into the playoffs in 1994. It was a really big deal at the time because people couldn't believe he did it. And it came up in the last dance. Simmons

and I didn't spend a ton of time on it. I don't think we spent any, but one of the things about the last dance for us and maybe some younger people out there listening is that we are now reliving these moments that we remember living in the moment. So some of the stuff that we're saying, it's like, yeah, yeah, but we know how it went down, how it was consumed at that time. We know how it went down, how it was consumed at that time. And Pippen got absolutely destroyed for not going back in. And I've argued in the past, in the moment, sometimes our analysis is the most off because we're the most emotional. It's the most recent.

Excessive is the right word to use for a lot of this. You go, you know what? That reaction seems a little excessive. But was it excessive in the moment when Pippen who has this great season in 93-94 after they had won the title against Phoenix Jordan's gone Pippen's got all these stats and I'm going through James Herbert's piece on cbs.com which is really good because it gives you a full timeline but it also consistently bangs the drum on like how much Pippen's teammates loved him.

And Pippen basically doesn't get to go back into the game against the Knicks. The game is tied. Excuse me. The play is not called for Pippen. There was an earlier play where Kukoc got kind of lost in the shuffle, and Pippen was pissed because he's like, well, he caused a traffic jam, and I wasn't able to get the shot off. And then they call it up where Pippen's going to inbound and the play is for Tony. They'd already blown a 22 point lead from the third quarter. They had this really weird stretch is this piece points out where in the first few games,

they were awful going up against the Knicks late in these games. Um, so they're breaking out of the huddle after the play is called and Scotty Pippen says, quote, bullshit. And then again, the coup coach point is brought up and this is all from sacred hoops from Phil Jackson's book. So there's further detail here. And he goes, I tell Pippen quote, you had an opportunity to score and it didn't work. Now we're going to do something else.

Then I turned around assuming the problem had been solved. But a few seconds later, I glanced over my shoulder and saw Scotty hunched over at the far end of the bench, glowering. Brian Schmitz at Orlando Sentinel said Pippen's inflated ego a mutinous act. Wilbon said that

some players around the league called Pippen a punk and that it was, quote, hard to disagree after watching him, quote, basically tell his teammates to go to hell and commit, quote, the biggest act of insubordination imaginable. Now, Wilbon did say it was Zach Lowe that he apologized to Pippen years later. And then Wilbon said in this piece, quote, I think I know him well enough to know that these things did hurt him and they were unnecessary and they were wrong. They were wrong. I mean, who wants to be judged at their worst moment? We can go on and on and

on with this. None of us want to be judged at our worst moment. But what I thought was very predictable for 2020 was that after the Pippen stuff happened, it was a lot of, well, you know, he got a bad rap for that. Or, oh, that was a little too excessive. I think Wilbon was on SportsCenter saying that. There's a few other people. And I don't know if it's because it's ESPN people that have to work with Scotty or they just like Scotty. They get to know him. They like him. I mean, people do really like Pippen. I remember Pippen's first run through ESPN. It was well over 10 years ago and he was kind of quiet. He wasn't that great on TV. He's had this resurgence where I think people do like him more and they really like the guy. So they don't want to see a guy they have a personal connection with. I'm not saying friendship, but just a personal working professional relationship with. They don't want to then have to beat him up because of something happened. But I'd ask this. Aren't there things that happen where you go, you know what?

That one is kind of screwed up, and I don't think it was wrong. You know why it was a big deal? It's because it doesn't happen. It doesn't happen when a guy's like, I don't want to go back to a playoff game because the call isn't for me. Now, was it wrong for Phil to have Pippen inbounding and not be a decoy, which is another part that Pippen had said going, you know what? At least have me as a decoy. Look, I get where Pippen was coming from a little bit post Jordan.

He's the man. He's had this great season. They've got a chance to knock off the Knicks without Jordan. They weren't in 50 plus games. They had a struggling season that next year when Jordan actually came back late for the last 17 but I get I can see how Pippen got to this point where it's like I'm finally going to be the man I've been the man all year we have a good basketball team and Tony Kukoc is going to take the last shot and I don't know if the decoy thing like it's a good

explanation but it's probably because he didn't get to take the last shot but the point of all of it is is that yeah like that's that's what's going to happen. When Michael Jordan in the piece, as Phil Jackson says, calls me the next day and goes, Scotty's never going to live this down. The reason this is a big deal, Bill Cartwright, if he's crying in the locker room after the game and looking at Scotty saying, I can't believe you did this, then who are media members to say 25 years later that Pippen got a bad rap for this? On a much, much lesser scale, I'm going to use an example here,

where Manny Ramirez, 2008, he didn't want to be with the Red Sox anymore. At one point in July, he had told Terry Francona his knee was sore and couldn't play for three weeks. And they were like, okay, well, let's do an MRI. And then at the MRI, he forgot which knee hurt. They did an MRI on both. They didn't find any damage. There was another time he didn't want to get on a plane. There was another at bat where

he didn't want to get into a game against the Phillies. He didn't want the Red Sox to pick up his option after 2008. The guy wanted out. He shoved the traveling secretary that was an older man. He got fined because of that. He got into it with Euclid's because he didn't get out of the dugout when there was a bench clearing brawl. And one of the ones I'll never forget, I'm in the hotel room. I'm across the street from ESPN I'll never forget, I'm in the hotel room. I'm across the street from ESPN, living in this hotel. I'm watching the Sox and Yanks. And Maynard Ramirez was supposed to have the day off.

They asked him to pinch hit because the go-ahead runner is at third. Mo Rivera on the mound. Yankee Stadium's rocking. Ramirez decides, all right, well, I don't even want to be here. Watches three pitches right down the middle, three strikes, walks back to the dugout. didn't give a bleep. And you go, that's somebody like Manny Ramirez, way worse teammate than Scottie Pippen could ever dream of.

And Manny, all that stuff's forgotten because it's the Red Sox. It wasn't the playoffs. It wasn't, you know, you remember if you're in Boston, but it's becoming a national thing. If Manny Ramirez had decided in a playoff game that he was maybe mad, well, I don't know. Look, he wouldn't be getting a day off in a playoff game at baseball, but if there was any equivalent to it where it could be in a playoff game that he was asked to go up there and decided, you know what?

I don't even want to be here, so I'm not even going to swing. I'm not even going to pay attention, take three straight pitches and go back to the dugout to prove some kind of point. Anyone that's a competitor, it's hard to wrap your head around that. So for Pippen to be criticized heavily and it still be part of his story 25 years later is fair. Doesn't mean any of us have to like it.

If Pippen's your favorite player, you just kind of have to accept it. And for anybody to say now, 25 years ago, that it was like misguided or use excessive there, that would be the wrong use of excessive. Let's talk Silk Road with the author of American Kingpin, Nick Bilton. You guys know I like doing some of the cooler book stuff that's out there. And this book is absolutely one that will go out and grab American Kingpin. The author is Nick Bilton. He also wrote a New York Times bestseller, Hatching Twitter, which I probably should go ahead and check out considering the hours that I've wasted on that website. So Nick, I know you're out in Los Angeles as well,

man. Thanks for joining us. Thanks for having me. And yeah, once you read Hatching Twitter, you will realize just how much of a waste of time Twitter really actually is. I don't know, man. I mean, I think I've done enough research, but it's a necessary evil for what we do as we have any of this stuff going on. All right. So let's dig right into this. I first heard about the Silk Road when I was researching Bitcoin because people like, oh, there's this drug website that you can go on. It's the Amazon of drugs and they can't trace anything because you use this thing called Bitcoin. And I was like, oh, and that was why Bitcoin had kind of this bad stigma around it. But let's just start with your first experience when you first heard about what Silk Road was. So I was a reporter for the New York Times at the time. And I was, I believe, a columnist then

writing about tech and business and the dark web and you name it. I mean, literally as a columnist, I wrote about all aspects of tech. And I lived in San Francisco at the time. I'd moved from New York, where I was a reporter, to SF because I was covering Apple and Twitter and so on. I was actually working on my Twitter book at the time. and so on. I was actually working on my Twitter book at the time. And I lived in this little area called Glen Park, which was on the, it's on the edge of San Francisco. At the time, it wasn't really like gentrified, but was up and coming. And there was a tiny library right where I lived. I mean, it was the size of like a two-car garage garage and i always used to walk by with my dog because

i'd walk my dog that way and i would think to myself who the hell goes to that library like it's so tiny what's what's the point of that thing even being there anymore and then cut to a few months later uh there was news that broke that the guy who had started the silk road website um ross albrecht who uh which you know, dealing in billions of dollars, potentially of drugs, had been arrested in that very public library right by my house. And that set me off on this kind of insane hunt to track down the story. And it became, honestly, without question of my 20-year career, the craziest story I've ever worked on in my whole life. Should we start with Ross then? Should we start with him and try to figure out who this kid is?

Yeah. I mean, I think that the, the, the, the fascinating part about Ross, the main character in the story, you know, is that he, he was like the sweetest kid. He, um, he would help old ladies across the street. I heard this one story from a friend of his where they were out walking one day in Austin, Texas, where he grew up, and they walked by a flower stall, and he stopped, and he said, hold on a second. He went back to the flower stall. He purchased a single rose and then handed it back to the woman who worked at the flower stall

and said something to her, and the friend said, what was that? And he said, well, I figured no one ever buys the woman who owns the flower stall flowers. And so incredibly thoughtful, you know, very caring. And he was, but he also had these beliefs, these libertarian beliefs that actually came from his family values and the way he was raised, where his mother especially had a big influence on him, where he believed that the government shouldn't be able to tell you what you can and cannot do with pretty much anything that's yours, your body, your property, whatever.

And it led him to this, down this kind of path that I think we all go down in certain degrees when we're like, you know, teens going on to college years. And the path that it led him down was that he believed that drugs should be completely legal and that the government had absolutely no right to tell you what drugs you can and cannot take. And he accidentally, essentially, stumbled across Bitcoin and the dark web and so on. And he decided, I'm going to build a website as an experiment. He taught himself all of it. Super smart guy. And he started to build this website that he called the Silk Road. And at first, he grew a giant black garbage bag of magic mushrooms in the woods in Bastrop Park out in Austin. Almost got caught by the cops.

Whole crazy story within itself in the book. And then started to sell them. And at first, he was like, you know, it's a little experiment. Like, he didn't think anyone would actually use it. And one day, like, someone bought, it's a little experiment. Like he didn't think anyone would actually use it. And if one day like someone bought like a little bag of mushrooms and he was like, holy shit, like it worked. And next thing he knew, along came Gawker, the website, the now defunct website. And they wrote about it as the Amazon of drugs. And that changed absolutely everything.

Before we get to the Gawker article, though, I love how great of a job you do setting up his libertarian beliefs. Because if you've ever read about Bitcoin, that's a big part of it. And there are parts of it where I think anybody that's read any of this stuff, you go, hey, not only questioning authority, just feeling as if we don't need authority. And then it becomes this philosophical debate of shouldn't there be someone in charge? So at the core of it, like there's libertarian beliefs, you go, okay, I get that. And then it turns into like, wait a minute, wait a minute. Like once the site turns into, hey, can we sell kidneys? What's up with poison? And you go, are you still a libertarian here? Are you just a capitalist in the entire thing? So that seemed to be the driving

force behind his beliefs. And as it seemed to take up another notch, especially Gawker being probably the best advertisement for the site ever, did he stay true to his beliefs or do you think he kind of lost the path along the way? Because he does start off as this guy that we could all see at any school that we went to. You know, it's interesting because he didn't. And I think that's what makes the story so fascinating is the question of who he became and what happened to him along the way. You know, as the story goes, Gawker writes, you know, this piece and they call it the Amazon of Drugs. And it explodes from there. The site crashes because so many people are using it

to buy, you to buy drugs. At this point, you've got people that are not just buying his magic mushrooms anymore. They're now buying drugs from other drug dealers. And other drug dealers are like, wait a second, I could go and just post my drugs on this website and people can buy them and I mail them to them and there's nothing that I can ever get in trouble for because all I'm doing is slipping them in a mailbox. And all they're doing is they can say, well, I didn't order this. Or I can go and like try to sell them in a park and maybe get arrested and get 10 years in jail. Like what's – it's a no-brainer.

So what happens is the site just explodes and it starts – he starts selling – people start selling all different kinds of drugs. He starts recruiting hackers from around the globe to work for him. Everything's done in Bitcoin. At this point in time, a Bitcoin was worth like mere, maybe a dollar or something, mere pennies in some instances. And so he's making, if he's selling, if he's getting a commission of a dollar off a drug deal, the next week it's worth $2. And when you start doing that at scale,

he's starting to make millions and millions of dollars. And then what happens is he goes on the run because somebody finds out that he's working on this site. And so he- This is when he goes to Australia? Goes to Australia and so on. And he has this like realization of like, he's like a kingpin really. Like he's like, he can be wherever he wants in the world.

He can, you know, he can travel however he wants. He can live this lavish life. He's got all this money. And the main thing that happens to him is he actually truly believes that he is changing the culture of the drug war. And, you know, there's a point where he's – what happened with my reporting was I ended up getting access to all of the chat logs that he had on his computer. And for three years, he ran the site, and he kept the chat logs with all of his employees. And it's over 2.1 million words of chats. You read all of this? We read all of it. I have a researcher that works with me on my books. of chats. You read all of this? We read all of it. I have a researcher that works with me on my books.

Not only did we read all of it, we got all the – I mean, the reporting and the research that went into this book is a book within itself. I mean, it's like we got all the chat logs. We got access to a lot of his photos on social media, his posts, so on and so forth. Got access to a bunch of his emails that were in the court documents. Got access to like text messages and all these different things. And then we kind of put together a database. Everything had a timestamp because it was all digital. So you have a database where you can see Ross becomes online. He starts to call himself the Dread Pirate Roberts from The Princess Bride. And so you can see when the Dread Pirate Roberts is online versus when Ross is online and what they're all posting.

And then you get to cross correlate all this stuff. And what becomes so fascinating is there's moments where the Dread Pirate Roberts, the guy who runs the website is like, oh, I'm going away for the weekend. And then there's moments where Ross posts a picture of him camping with his girlfriend. And it's like, and you really just get to see these two different personalities.

But Ross essentially starts to believe in one of the chats. He says, like, he says, I'm really going to change the drug laws. People are going to see that if you buy drugs online legally, the crime will go down and so on and so forth. So he had this inflated sense of what was really happening. And then things started to go a little haywire because he had the people essentially were threatening to take him down. He had literally every law enforcement on the planet was looking for him from like state level police to the FBI, CIA, Scotland Yard, you name it. Because it was a global business.

But before it became, as you point out in the book, basically a competition from all these different parties, you've got an IRS element to it. You've got the DEA. You've got a guy in Chicago who was basically at a very low level kind of, I don't, we call it customs. Was Jared a customs guy or? Yeah, you've got, so in the US you've got, you've got Jared Duryagan, who was a customs guy.

And then when 9-11 happened, they took customs and they kind of put it all into Department of Homeland Security. And there was the HSI and there's all these different groups under there, but he became an agent. And then you've got the FBI. You have this guy, Chris Tarbell, who was in the cybercrime division, which they actually sat in the FBI building in lower Manhattan. They took over where the old mobster FBI agents used to be, which just showed you how important the cybercrime units was. You had this guy, Gary Alford, who a lot of people love as a character. He would read everything

three times, very, very anal in his research and everything. He was in the IRS. And you have this guy, Carl Force, who was at the DEA, who was a total lunatic. And another guy who was at the Secret Service because of the money aspect. You had these people all over the place. And the DEA agent and the Secret Service agent, they ended up turning and working for Ross. But at the same time, they were also scamming him at the same time. So it's like it becomes this like novellalla like where you can't even like everyone is out to get everyone else and what i think one of the things that like that i find so fascinating about the story is that you know when you hear all these conspiracy theories around coronavirus

and things like that and they're like the government's doing this like these were like five agents and they couldn't they couldn't get their shit together to be able to tell each other just the the tiniest little details because it was so – and it's like you look at this, and these are good guys. They're not bad people. They just – it's just there's so much information flowing around. There's so many people and their bosses and this and that and the other, and all the agencies want to win and be the guy who catches them. There's no fucking way that there is a government-led conspiracy theory for anything it's just like you cannot pull they can't even pull off arresting like a 20 something year old kid without like

stumbling over each other like and i think that it just happens in this thing where you see things that just they they're the turns that are missed and so on and so forth and it it just leads to this crazy cat and mouse chase uh game before it was kind of defined though that these are all the people going after him it was really interesting to see how hard of a sell it was to even investigate it because people this is new this is like a pioneer in a way with ross where you're going like wait a minute what is this guy doing like no that can't true. Like he can't be really doing this. How hard was it to get anybody to actually back the idea of an investigation to something that was really at the forefront of drug dealing on the dark web? Well, what was really interesting was they, um, you know,

I think this was like one of the parts of the story that I, it's fascinating when you look at it in real time and in hindsight, because at the time, there was no law for how you would catch someone doing a drug bust, how you do a drug bust. So at the DEA, what they used to do were these things called jump outs. And what they would do is they would get in a van and they would drive around Baltimore and they would pull up to a corner, they'd jump out of the van and they'd arrest the guy who didn't get – who, you know, they caught and throw him in jail because he had a few bags of coke on him or whatever it was. And totally not effective, right? They do nothing to really stop the war on drugs except, you know, arrest the lowest-level person. And at the Department of Homeland Security, their mandate wasn't drugs, whereas they oversaw mail stuff that was coming in.

They would go to – when packages come from the Netherlands or whatever and there's drugs that are found in them, the Department of Homeland Security, they're the guys who go in and do it and look at the evidence and so on. But they're not allowed to do things that the DEA does. The FBI is only allowed to do digital stuff. They're not allowed to touch the mail, the IRS. It's like no one's allowed to do anything. And so they all had to kind of find ways to work around it. And Jared Driegan, who is the Homeland Security agent, who is a really sweet guy, really truly cares about,

you know, what he's doing and protecting America and everything. He comes up with this idea. He finds a single pink pill in the mail coming from the Netherlands and going to a guy in Chicago. And it just doesn't make any sense. Why is someone sending one pill of ecstasy? And he has this very insightful realization that if it's a pink pill today of ecstasy, it'll be 100 next week. And if it's 100 next week, it'll be guns. And then you could imagine terrorists coming into the United States. They don't need to bring guns or money. They could just do it all through the dark web and so on. And sure enough, he was right. And eventually, the Silk Road starts to sell guns. They start a Silk Road for guns called the Armory.

And that's when kind of all these agencies came together because it was guns, it was money laundering, it was drugs. Eventually, as you say, there was discussions of body parts and all these crazy things. And that was the thing that actually brought everyone together to kind of try to try to really catch him. So Ross is this brilliant guy, as you mentioned, I mean, he's sitting here, he's doing the coding, he's trying to figure this stuff out, but then real like intense programming, engineering types can see some of the flaws in his design. They start blackmailing him by trying to shut it down. There's people that are going after him with information. And then he gets into the point where he believes at some point there's an informant, somebody who would work for him that could give up more information. And

whenever you're reading a story, sometimes you inherently root for the first person you're introduced to. It happens in movie and television. I think there's always an outlaw part of us that that we glorify we're like oh is ross gonna get away from this or get away with this but as soon as he's kind of like yeah you know hey i'm a libertarian and yeah let's have this guy murdered like how does he go to the point where and this is a big part of the sentencing where a i at one point was trying to sell some mushrooms to see what would happen and now i'm paying hell's angels members to murder guys. And then especially with the first guy that he thought was actually killed, which is a whole nother story where it's all a setup. I mean, could you see that in the logs? Is there more depth to that in the logs where you can see this guy evolving into somebody

who is okay with ordering and paying for a murder? You know, I think that it's interesting because every once in a while, Ross has a Twitter account now from jail. And knowing he goes to jail does not give away any part of the book in any shape or form. I mean, it's like really kind of an astounding story with or without that. And I go look at it once in a while, and there's part of me that legitimately, you know, feels bad, like, that he ended up where he ended up. But at the same time, I think that he did make some really, like, bad decisions that affected a lot of people. You know, there were people that between the lines of the things he's said since he was caught and in his sentencing to kind of get an idea of the fact that like there was clear regret there. But there's also, there's two sides to him. You know, I mean, I think that he was offered a plea deal when he was caught that probably would have put him in jail for 10 years.

He would have been getting out in like three years or something like that. He's been there for seven now. And he chose to fight it because he thought he could win. And in the same respect as he thought he could change the drug laws by taking the approach he took by building the Silk Road. And I think that he, I think it was his hubris that was his downfall more than anything.

And he, you know, he would have been getting out in three years and he chose to fight it. And that is not going to be the case. But it's interesting because I think that when you look at the chat logs, you can see there's these moments and the stuff that I didn't actually put in the book, like there's one part where one of his employees, he's got employees all over the place that are working for him. There's one part where one of his employees, he's got employees all over the place that are working for him. And there's one part where one of his employees says he's late to work. And Ross and Dreadpire Roberts and the employee are talking.

And the employee says, I'm sorry I'm late. Something happened with my kid. And he said, oh, what happened? He's like, I have an 11-year-old kid. And he was playing at the playground. Some kids try to sell him drugs. And Dreadpireed Roberts is like, that's so fucked up at the playground. And he's like, yeah, it's not fucked up. And I'm like thinking to myself, like, what?

You guys are running a website where kids are buying drugs from it. So I think that there was this disconnect. You know, like at the same time in that same chat log, they had a meeting with the employees of the Silk Road where they were talking about promotions they were going to do. So it was like they had like Super Drug Tuesday or whatever it was where you like buy a thing of weed and you get one free and all these things. And I think that it was so – I think the part of it was that the – from a technological standpoint, like it's the same thing like bringing this back to Twitter in the beginning. When you go on Twitter, like people can call you every name in the book. They don't see how it hurts you. They don't see how it affects you.

You know, it's like it's the same thing with selling drugs on the Internet or anything with fake news, with all these different things, with Donald Trump being Donald Trump. It's that you can put these things out there and you do not see the human side of the toll of that. And I think the same thing was happening with the drugs. But what happened was he was so caught up in this little world that he created that he thought was much bigger that when people started to threaten him and the site and to take it down, I think in his mind, he was like, okay, I'm probably, I'm saving lives by allowing this thing. So if I have to kill one life for, it's like that question, would you kill one person to save a million? You know, I don't, I don't know. I don't know the answer. He chose to do it. And, or at least he thought he was doing it. And you can definitely see that struggle. I think the first time he waited 24 hours, he went for a long walk, funnily enough, in the same place that I would go for a walk,

like, which was wild. He, you know, he was, and then he just said, fuck it, let's do it. And so there was definitely that struggle between those two different sides of him. And I think that that's essentially, between those two different sides of him. Um, and I think that that's essentially, you know,

where he ended up. When he gets arrested in that library, there, there's a couple of things here where, you know, I always wonder, is the public right for challenging everything or is the public just so wrong all the time?

And it kind of depends on what field you're in to be able to figure out who you are. But when Ross is being arrested after this exhaustive investigation, they're tracking him for weeks, it sounds like. And they finally get him because they have to get him in a certain way, which is weird because I remember now going back and reading about this arrest. And there's a couple of things that happened. But the first thing that's hilarious in the book is that other patrons in the library are screaming at the FBI officials to be like, oh, that kid was just on his computer. Yeah, exactly.

That's where if you're in law enforcement, you're like, I don't have time for anybody. Yeah, totally. I've been following this kid for two weeks. We have a year's worth of research on this thing. Two years, I think. And you're telling us to leave alone the kid with the hoodie. And then during the trial, the defense, and he has this big, big-time lawyer who's essentially saying, Hey, the Dread Pirate Roberts is multiple people, and it's just the login name, and and it's been passed on and Ross is not that guy.

And it was, I remember the first time hearing about that going, Oh wow, that, that might suck. Like this kid was just sort of running the site at the time. And how surprised were you when it was happening? And then also looking at it, a lot of the media bought that up like we're selling that this kid was was essentially set up by other people i mean look i think that um it's interesting because i was there i covered the trial for the times um i sat in the courtroom for a month and um and i think you know i think personally i think i think the lawyer was an awful, awful choice. I mean, he was a big-time lawyer who had defended some huge terrorist cases and drug deal – big, big, big expensive lawyer. He knew absolutely nothing about technology.

And I mean, some of the questions were like – I mean, I remember he tried to get – I think it was Jared Diegan, tried to get him on the stand because he's like, were you using Ubuntu 1.01? But it says here it was 1.02. And it was like, what? Like, that's your defense? Like, that it's two different versions of Linux? Like, you know, it's just, and you could see the jury's eyes just glaze over. And I think that, I think that the, you know, the, what his defense should have been in my personal opinion. And I spoke to other people who had covered the courts for a long time at the New York times about this. Cause I was curious what they thought if he'd have gone

in there and he'd have said, Hey, I'm just some like some, you know, privileged white kid who screwed up and it went too far and I didn't know how to get out and I'm so sorry and I'm going to dedicate my life to trying to fix this and like whatever, he probably would have gotten off on like a very small charge. But he didn't. He tried to defend himself and use that same defense that I'm just some privileged white kid to say that what he was doing, A, it't him, and B, even if it was him, it wasn't that bad. And the judge, I think, was incredibly smart. And she said, you know, I remember once I was sitting in the court when there was a recess. And during the

recess, the judge was doing sentencing sometimes. And I stayed in the courtroom and there was an African-American kid that came in. His wife and little baby were right behind him. He was from Harlem and he had been sentenced. They were sentencing him for selling cocaine in Harlem. And she gave him 20 years because that was the state minimum, whatever it was, the federal minimum. And the mother was screaming and crying and the kid was, and you know, and that kid was, it was so, what the judge was saying was like that was his job. Like that was the only, he had no choice. She understood it and she didn't want to, but that was the law and she had to uphold the law. So with Ross, when it came time for his sentence and she was very aware of how it was his choice you know um

and uh he had made that choice and if he was going to make that choice then he had to suffer the consequences of that choice and and i think that you know it's it's difficult like i remember i might say to my researcher at one point i just had a little kid when when this was all going on i said you know like it must be so hard for like like Ross's family to see him going to jail for the rest of his life. And, and, you know, and she's, my researcher said, yeah, but he would have happily sold drugs to your, your one-year-old, you know, like, so it's, it's like, and he killed the person. Like, it's just like, there's two sides to the story. And I think that, um, it wasn't until he was caught that he actually got to see those other sides. Speaking of his family, um, you know,

family members wrote letters, which is what happens in this, you know, he's a great kid. It's misunderstood. Uh, you know, the, the, the most biased person is usually the mother in the situation like this. And she called your book, a media lynching. What was, what was your feeling when you first heard that? You know, I'm a little torn with, with his mom, because there's part of me that feels, feels terrible that this is what happened to her son. You know, I can't imagine what she she's going through. And I try to have empathy for her and her father. I mean, his father, I remember when I was, his father was such a sweet guy. And I remember we were waiting for sentencing and we were all down, everyone was down in the cafeteria to meet all the reporters and at the courthouse.

And I was waiting to get a soda and so was he and I was like after you and I said um I said you know how you know how are you doing or something like that and he just he's kind of snapped at me and I I was like I get it like whatever like you know and uh he's like I don't want to talk about it whatever and he walked back up to me like a minute later he said I'm really sorry that I was rude just now he's like this is very't want to talk about it, whatever. And he walked back up to me like a minute later and he said, I'm really sorry that I was rude just now. He's like, this is very stressful. And I was like, you do not need to apologize to me. Like, I am the last person on this planet. And just the fact that he did that, like, you know, he's a very sweet man.

is that she has gone through systematically since this whole thing started and blamed every single solitary human being on this planet, even the families of the kids who died. It was their fault, not Ross's, right, of six kids that died because of this little grub. She's blamed every single one of them. She has never once blamed her son. And so she can call my book whatever the fuck she wants. Like she organized this whole thing where she had a bunch of people go

and leave negative comments on Amazon and Goodreads. I mean, they've got filtered away because so many other people left normal comments. But like she was on a podcast saying that I was like an undercover CIA agent. I mean, give me a fucking break. Like I'm a reporter who, who wrote this book. And then later they tried to use my book as a defense in court when they were trying

to get a retrial because of the, because some of the FBI stuff I put in there from my reporting. And so you don't get to use both sides of it with all due respect. And I think that like, I think that if she, if she would focus on, on trying to get her son—she made up all these different stories, and every time it didn't work, it was like, let's just throw that story away and try a different one. And people pay attention to that stuff. And I think Ross has a lot of supporters, and rightly so, because he did want to change the drug laws and this, that, and the other. And I don't believe that that black kid in Harlem should be getting 20 years in jail because he sold drugs. I think that there's a problem with the system. But I also don't believe that a kid in his bedroom should get to decide how the system is being rewritten. And I think that from his mother's perspective, I think that, again,

it must be incredibly hard, but you can blame everyone you want. It's not the reporter's fault for writing the book or the people who made the movie or the people who wrote the story or whatever. It's just not. Last one here. Will you ever – I imagine you reached out. I read in the research part of it. Ross didn't want to be interviewed, but will you talk to him? I mean, I would happily talk to him. I think about him quite a bit.

I think it's like when you write a book, you move into your house with these characters. They go to bed with you at night and wake up with you in the morning, and you spend a lot of time with them. And for Ross, I think it must, you know, I think he probably regrets a lot of his actions, I would imagine. I don't know. But I would, you know, I would definitely like to talk to him at some point. I think that he, you know, the judge said this line that I think about a lot where she said, you know, there's good in people and there's bad in people. And, you know, there's definitely good in you, Ross, but there's also a lot of bad. And I wonder, you know, it's interesting, like, bringing this back to the quarantine and everything.

I was thinking – I had a podcast I was doing for Vanity Fair for a while that I no longer do. about prison reform for the podcast and spoken to people involved in trying to change recidivism rates and so on and so forth. And I remember I interviewed the folks behind the movie Man on Fire, which is based on the incredible New Yorker article about the man who was put to death for allegedly killing his three kids in a fire. And I remember this line in the story where the guy who allegedly killed his kids, where he says, you know, he's been in solitary confinement for years before on death row. And he said, imagine, you want to know what solitary is like? He said, go in your kitchen for a day and don't leave. Just stay in your kitchen for an entire day and don't leave. And you hear these stories of people like, I'm going stir crazy after two months in my house.

And I have a backyard and this and that. And the other night, I can still go out for walks, but I'm still going stir crazy. Imagine what that's like to be in solitary confinement for 20 years, to not see other human beings, to not be around other people and and i think that um i don't you know i i don't i think that with all these stories that we read and we talk about there are two sides to all of it and and it doesn't mean that they're right or they're wrong i do i think that ross was wrong absolutely do i think that that that the punishment is wrong? Absolutely. You know, I think that there's, that the system is definitely broken in all regards. And, you know, I think that I'm sure that he's had a lot of thoughts on that. And, you know, I think, will he ever speak to me? I don't know. I'm sure I'm the last person on his mind. Uh, but, uh, but it's definitely something I think about quite a lot. I enjoyed the book tremendously. I recommend it to a bunch of people out there and listen to this pod too. I mean, it's true because we're trying to do it without giving away every single element

of it, but there's just so many, there's so many parts of this, the DAA part that we, I didn't want to touch on in a way, cause it's just kind of fun to discover that throughout the whole thing uh but this is a great i can't imagine the amount of work that you had to put into this thing but uh well it was another thing is um i i actually totally forgot until we started talking but it's on sale for 2.99 on amazon right now i didn't even know that is that good or bad it's good because i mean if they're doing like a promo for people that are quarantined so like you can go get it for three bucks i guess it's cheaper than a coffee but um but yeah it's it's honestly like i still i will say this again like i've been doing this for 20 years crazy story i've ever worked on just the twists and the turns and the characters are

just yeah it's wild so that's at nick bilton and it's b-i-l-t-o-n thanks a lot yes thank you so much for having me hey this is brian koppelman and this is david levine we are the showrunners and co-creators of billions and this is behind the billions behind the billions we're going to talk about how we make the show the decisions we made in terms of uh what we decided to shoot how we make the show, the decisions we made in terms of what we decided to shoot, how we wrote it. We are going to share the inside skinny on what it's like to make the show. Dave, I'm sorry. I just said inside skinny. You did. I mean, you've set the bar high. We have a lot to provide now. And we will be providing it on Sunday nights right after the show. We'll have guests who are actors on the show will come in and talk to us,

people who make cameos on the show. Should we interview crew members too? Well, we're going to talk about some crew members, maybe standout crew members, superstars, crew superstars, if you will. Really psyched to do this, psyched to talk to everybody about the show. Listen in on Sunday nights

right after the show airs on Showtime. I hope you guys enjoyed that. I ripped through this book and more and more books that I'm reading, they're just doing this thing where they're kind of like, maybe it's just books lately.

I've been in this run of books happening this way, but one chapter's following this one part of the story and then you get back to that three or four chapters later because there's like three different things

going on at the same time. And it's a good way to write because it keeps it moving you don't get stuck on one guy or you don't get sick of one guy after 20 30 pages or something like that i started reading the new office book oral history of the office so far my favorite part is that on diversity day which they say is basically the groundbreaking episode, the episode that showed like, okay, wait a minute, this can break off from the English version of The Office. And it is a really difficult thing to do. And yeah, it's like most people in the beginning were like, oh, this is going to suck. They're going to do some American version of this BBC thing, like good luck. But Steve Carell being the 40-year-old virgin that early on helped the show. My Name is Earl is the lead up and Diversity Day was kind of like, wait a minute. And like a lot of things where you go, is this sometimes the year old virgin that early on helped the show my name is earl is the lead up and diversity day was

kind of like wait a minute and like a lot of things where you go is this sometimes the sitcom writing i don't man that's tough that's tough stuff because if you try to do like oh we're going to do the super brilliant thing well is anybody going to get it because we still need people to watch it and that was a real fear when you read this book about the office but diversity day they'd come up with all these different things and if if you haven't seen it, they, Michael Scott decides to make these postcards where everybody has to put a different ethnicity on their forehead. And it's almost like blind man's bluff where you put it up and then it's like, okay, no one's, you're going to have to guess what your, your, your note card says on your head

based on the way the other person is talking to you. And he's like, you know, really push the limits here. Let's go. So, you know, there's one that's like Jamaican and the other guy's like, do you want to get high? And she's like, no. He's like, I think you do. And then there's one that says, yeah, yeah, man.

And then there's one that says Jewish and then black. And then they said there was one they made that was szechuan and they're like we didn't use it but they're like one of the ones we were going to use was was szechuan and i i really got a chuckle out of that in the book i think michael was martin luther king junior right that would say that yeah he assigned himself that one um so and that was after michael scott had done the chris rock routine but just larry wilmore in that episode larry wilmore is so good in it he's so good at it just kind of being i'm always interested in actors that can find ways to act without having like i actually think it's easier to act on the fringes than it

would be to act as the straight person and make it. You don't have all these moments where you get to show off. You have to kind of like play in the background a little bit. And Wilmore, I went back and watched it after reading that chapter because it had been a little while. And Wilmore is so good at it. He's great at it. He really is. I'm like, man, he's so frustrated.

He's earnestly frustrated with with michael scott and they also talk about trying to lessen scott's edge and the development of season one to season two and as you remember in season one michael scott has his hair slicked back and that was a conscious decision i always thought it was because it was clear that scott was balding a little bit like steve crowe was actually balding may have had a little reseating done shout out to anybody uh that does it good for you um but they decided to not slick his hair back because they wanted to soften him they felt like he was too harsh and too mean and that's why like the ricky gervais character like i think the ricky gervais thing is so good that david brent they could have figured out it would have been fine if they had done a season three and four there's arguments in the book that he was too mean and that,

you know, after season two, the thing was done. I don't, I don't know. I don't really believe in those things, but, uh,

the sitcom part of the writing, uh, I can't, I don't know, man, that's, that's really hard to do really hard to do. All right,

let's get some advice in here. Again, the email is life advice, RR at Gmail. Um, this is from the, I don't know if we're going to supposed to do names can you guys put at the top of these use my name don't use my name because it sounds like anybody that knows this guy let's call him b i'm a 23 year old guy from nebraska looking for

some thoughtful direction i've always been a smart and pretty athletic kid shout out to your body until i was 17 to 21 ish oh okay i didn't get it i was just coasting did great in school i had no dreams applied to local colleges and took until i took a campus visit to notre dame weird kind of inspiration came over me worked hard as a freshman at a no-name college transferred into nd wow this is like the academic rudy thought i made it started coasting again senior year rolls around well it. Started coasting again. Senior year rolls around. Well, look, if you coasted again and graduated from ND, congratulate yourself there, first of all. Senior year rolls around and you realize all your peers had high prestige internships last summer and you needed

one for any job that matters. I was out here working for my uncle. Who knows? He finds a company, pays him a decent salary when i graduate says he could probably get to six figures next year that's probably what you tell girls um but that's cool feel free to write me off oh see self-awareness here even at 23 after he drops the six figures on us he says feel free to write me off he goes but i did graduate with 110k in debt so it's not like i'm high rolling. I still have $90,000 in debt. First of all, guys and gals, you can't really get too freaked out about the college debt part. You are getting screwed.

That is something I'm very pro-millennial about. I don't think this should be a political thing. The amount that you guys pay in tuition and the loans that you take on and the idea that I'm not saying education doesn't matter. I don't know if we'll get to alternative paths. I'm sure there's some out there that have said, screw it. I don't want to take on those kinds of loans. And I don't think you should. I mean, I just, the administrative costs and the number of people that are hired now at these universities to drive up to these costs to make it all justified, you're getting absolutely screwed over. And I don't know what the counter argument to that is. Feel free to send in a non-life advice if you're a

college administrator that actually thinks these tuition prices and the number of kids that are entering school. I remember signing all these, oh, this is the Pell Grant. This is this. This is all these deals. And I graduated with all sorts of debt. But I didn't really think about it. I also went to default, too, because I was supposed to have a plan. The plan did not happen. I'm going to keep that one to myself. It wasn't anything illegal.

It wasn't anything bad. It was just an arrangement that then ended up not being the arrangement. So I was like, all right, whatever. I'm chasing my dream. And I would get the forbearance. I would put it off. I would put it off. I would put it off. Don't do that because it's going to screw up the credit.

All right. I paid it all off eventually, but I didn't really like there's debt. And then there's kind of debt that we don't really accept as debt. Like when somebody says they own all these houses, like, do you own them? Or do you just have a bunch of mortgages? You know, like, but we never, we never say like, oh, hey, I'm debt-free. Like, well, do you own your house or your car? Well, no, I make payments. Well, technically, you're not really debt-free,

but there's a way that we've accepted some debt as like, oh, my God, look at all this credit card debt. Look at this terrible debt. Like, how much are you paying every month on your restoration hardware card? That's the kind of debt that scares people. I'm just telling you, any college debt, it's necessary evil. You're getting screwed over, but don't carry that around like it's this thing that has to change every decision that you're going to make. I know that sounds easy because I made the wrong decisions, but I didn't let it bother me. And I'm not saying

like, don't pay it, but don't, don't look at it. Cause we all know like those payments are a little different and the interest is different than some of these. It's not like you borrowed a hundred grand from a bank. All right. Um, even though if you bought, borrowed a hundred grand right now for a house, it would, uh, well, I'm not going to sit here and do an interest rate breakdown. But so back to our guy here. I proved something to myself when I got an ND. I'm proving my own potential on this job on a daily basis. But he's in Wisconsin.

And then he asked, what am I going to do? Get blasted with a bunch of 19-year-olds at Whiskey Jack's or the W? Or make friends with the 26-year-old lifers? Hope nobody recognizes this guy. It feels like I'm locked into a city that makes me cringe. I've got creative and big city dreams. I want to work on something that matters, something that people enjoy, something that adds to our culture.

Whoa. Jeez. Another Ross Ulbricht here. Just kidding. But I get down, man. i get down man i get down all right i thought he like was talking about dancing or partying here i get down comma man oh man feel stuck in madison don't want to make friends so i just isolate outside of work pretty social guy so it feels strange big dreams being weighed down by a small town how do i make a move i want to find something i love but i want to be able to make but do i want to make 40 grand a year in

new york city or boston and with rent and all these loans i feel that i can be the best wherever i land but i don't want to close doors and cap out future success in case you want to take the girl angle there's a girl in town and there's mutual interest, but don't want to lock myself into the city any further by getting a girlfriend. Feel free to blast me on this too. Okay. A lot going on. All right. Let's focus on the positives. You're 23. So get over yourself. Relax. There's a really weird thing. I went through it too when I was 23 and I was still in my college town. I felt like I was a dinosaur and I was seriously like a year older, even though because I was young when I graduated, I felt like a dinosaur compared to guys that were seriously not only

23 if they were on the older side of graduating or 22 like most people when they were graduating, depending on when your birthday lands. And yet, because I had been a couple years older than these guys in classes, I thought, oh, I'm so like, I can't hang out with these guys. I feel like such a loser that really cranked in the loser factor when I turned 26 and I was still there. And at that point, you know, that last year that I was in Burlington, I needed to get out of there and I was making plans to move. So you're 23 relax, not a big deal. The other positive that you want more, these are good things. So part of wanting more and being

driven and expecting more of yourself can also be maddening because you get down on yourself probably a little bit more because you're holding yourself to this kind of standard. Think of that as a positive. Yes, when I drive by simple towns, especially when I would drive through Vermont up and down probably, I don't know, a thousand times. A thousand seems high. That might be, you know, let's say hundreds, but I've done that trip quite a bit. A thousand is way too high, though. Yeah, let's stop that. Although I probably was in a car

enough. All right, this is, I'm going to ask Kyle to edit this out, but I'm not because I'm punishing myself because how terrible those last few sentences were. The point is, is I would do this thing where I would drive through these little towns because I liked all these little towns and I would see like an old trailer park and I'd see those big 80 satellite dishes. And I would think, hey, what if you were just simple and you lived there and you didn't put this pressure on yourself and maybe you met a little

girl in town and I don't mean age there or even size, you know what I'm saying? So it sounded creepy, but you met like your high school sweetheart and you got married and you had your two and a half kids and maybe you went to the VFW and by the time you were 30, you were like, hey, this is good. I've got my little side business or I'm doing some construction and the big trip into Burlington every month or so. Maybe you even get a boat one day on a piece of property with a little water. And as soon as I would say it out loud, I'd be like, hey, whoa. You know you wouldn't want to do that.

So stop creating some version where you actually think that that would be a solution to... I don't know. When you're driven, it could be very maddening. All right. It's a really frustrating thing at times where you're like, why the hell isn't this stuff happened? What's next? What's going on here? All right. So what you learn to do, or at least what I learned to do is like, all right, so I could drive myself crazy or I could go, hey, this is just the way I'm wired. I don't want the easy thing. I've never wanted the easy thing ever. And if you're 23 and you want the big city, big dreams, I don't know about what kind of cultural impact you're going to have. So maybe we can tone down those aspirations right now. And I'm not saying put a sour cap on yourself. I'm just saying like, I don't know, are you going to be a great painter?

Are you going to be a spoken word guy? I don't know. But don't be freaked out because you want more. All right? Now, there's going to be some point in life where maybe it doesn't happen and you have to accept what you have. And that's going to be really, really tough. But don't get mad at yourself because you want a little bit more. That's cool. Now, as far as the girl thing, you're also, that's stupid.

If you like her and she likes you and you're both in the same town, you know, whatever. And if you end up not liking her enough that you don't want her to be part of the move or she's not going to take the ride with you, then you can break up. People breaking up all the time.

All right? Super easy. Yeah. Somebody's going to do it today. So what you're doing, and I know exactly what you're doing. You're doing all these things because you're so caught up in yourself, and you're 23, and you haven't had a life experience, which is part of the whole problem. And it's not a criticism. It's just you're so wrapped up in your own little deal right now that you can't even understand that, like, you know what? Deep breath. Everything's good. Look what I've already accomplished. Although you don't want to do like, I'm not going to do ever the, Hey, you need, you deserve to give yourself more credit. I remember one of my roommates in

college was dating this girl. God, this is funny. And she, uh, she was great. This girl was really great, but he was, I was like, how's it going with her? He's like, you know, it's, it's good. It's good. He's like, I really like her. He goes, you know, she's got a really cool way about her. I was like, Oh, what's, why is that? He goes, you know, I was, I was kind of getting down on myself the other day. And he goes, you know, she just put her hand on my hand and said, Hey, you know what? Think about all the things you've done. You need to give yourself more credit. He's like, it was so great. No one's ever said that to me. I was like, oh, wow.

That's really cool. How mature is she? That's a really cool thing to do. I think we were all early 20s. Then I think two weeks later, we were all out and I was with a girl and it wasn't really a double date thing, but it was two guys, two girls.

I had said something to the group and his girlfriend like put her hand on my hand it was like you know you need to give yourself more credit he was like oh we're like oh my god that's her move that wasn't insightful that wasn't her connecting with you like someone told her that once and then she just uses that that's the yeah she just and he was he broke up with her pretty quick after that it was like oh because i knew exactly what was happening because he was so excited about the moment and explaining it to me so uh i'm not doing the hey give yourself more credit but you deserve to give yourself more credit so some guys had internships at banks or something more prestigious than what you did who cares cares? It doesn't matter. Half of those guys are going to be losers. The other half are going to be really successful. I'm sorry. That's just the way it is. That sounds a little harsh, but don't pre-compare these endings that don't

even exist yet for you and these other guys. So God, that was a massive, massive breakdown for this dude. But I would just say, look, if you want to move, move. Don't start putting all these hurdles in front of you that aren't really as big as you think they are, but you really can't. It's just what you're going to do because you're a young guy. All right, let's move faster on these next two. That was brutal.

Is anybody still listening? Okay. Michael wants to know, dating while balding. Ryan, as you're probably expecting, I first want to thank you for the great podcasting. Appreciate it. Okay. I have a question. A 24-year-old single guy living in Chicago. And I do admit I have many qualities that women might find attractive.

Not lacking confidence. Academically, I'm currently attending law school. Boom. Physically, I'm in good shape. I've been told. Oh, wait. This is too good. He adds, I have a great voice.

Ah, do you? Like singing? No, that's it. Radio voice. That's it. It's just, I mean, here's the sentence. Academically, academically comma i'm currently attending law school semicolon physically comma i'm in good shape parentheses i've been told

i have a great voice semicolon socially oh god please be another comma yes all right i was going to say you have a great voice socially uh i enjoy a night out and I have the friends join me. So he's got a crew. However, I'm also quickly and decisively going bald. I shave my own head every week so that my hair never grows beyond a fresh buzz cut, but my thinning hair nonetheless shows. And I worry that it significantly hurts my chances of getting a girlfriend. I know you've previously touched on your own experience with thinning hair. So do you have any advice on dating with barely their hair how it can effectively um compete with more follicle fortunate men yeah all right well michael i was on tv so even though the hair was falling out on the top i at least had something interesting to say

and i always thought that when i was younger, when I would notice what girls like, because this is really important, we can pretend it's not important, but as guys, we care. And girls care about different things. I actually think they may be, well, there's a lot of things that girls are better at than us. But I think guys do care about the opposite sex looks far more than we care about their achievements and i think women care more about achievements they're attracted more to success so the long play here michael is to be successful i don't know what your height is that usually plays a factor so i'm not trying to bum you out um and be funny yeah you can be funny guy but well it's all inside jokes you know you took communication classes right you learn that like inside jokes if you can develop those

it's like a it's a big win wait a minute i don't i don't think i knew any of this stuff kyle what are you talking about weren't you a communications guy no maybe i just had an off off the rails communications professor i don't know but they always say you notice the more inside jokes you have with somebody like the uh the more like uh i mean you could do it with men and women so i'm not gonna say attractive but it's like stronger relationships people feel more comfortable around you the more inside jokes i live inside jokes literally borrow one someday um i don't i don't know i never took a communications course so i don't i don't know uh i'm not saying you're wrong i'd never i just never heard that before it sucks man i don't know uh i'm not saying you're wrong i'd never i

just never heard that before it sucks man i don't know what to tell you you know you're 24 your hair's falling out that's that's too early that's not fair um i had one friend who got married to somebody he didn't really like but he was like look this is probably the best i'll ever do because i'm starting to lose my hair pretty sure that guy's miserable. So I'm not saying go that route. But like we just heard with the American Kingpin author, another part of that story where this kid starts Silk Road, he got dumped by a girl he was going to propose to. Right when he was about to propose to her, she's like, I'm cheating on you with your friend. And he was like, all right, now I'm going to be a multimillionaire online drug lord. So there's nothing more motivating than getting dumped. Sometimes I wonder if that's why I ended up being successful. Because I was like, all right, it's on. Like, out of the way. So I'm not saying, hey, go out there and get dumped.

But yeah, I don't know. Maybe you're just going to meet somebody who loves your voice and body. And none of this really even matters. I mean, there are girls out there. I'm telling you, Michael, here's the way to end this on a positive. There are girls out there that like guys with bald heads. I don't know if there's a farmers only. I mean, hell, there's everything out there.

There's probably some, you know, it's not a fetish, but don't worry about it. It's not that big of a deal. And the fact that you've already started shaving it a little bit, huge leg up because comb over guys about 12 games behind in the division standings from god that's accepted it and just think at 24 you've already jumped into it so even if you're single for a few more years like nobody's even gonna remember that you had hair when someone sees a photo of me with hair and it's only like five six years ago i'm 38 years old people freak out and i'm

like all right yeah so think about this man you're good you're getting on this early okay one more oh okay this is good a quick one tim asks whatever happened in the espn promo where you could bid on watching games with you in your basement told the story i missed it by way. I think I was the guy who killed the rate the show segment with Rosillo and Connell when I said that it was easy to get through on a call. Oh, yeah, that's right. We did a rate the show thing. We were always trying to figure out new ways to end Rosillo and Connell, and we never landed on it. We just did a bad job. We did lists. We did rate the give it we actually thought that was going

to be kind of funny and then it didn't play and i guess tim got right through and then said on the air he's like huh i got right through we never took any calls i don't know that we ever gave out the number so that's probably why it came through or it's just hard in the middle of the day be like all right i'm gonna call and rate this radio show real quick. I don't know what happened with that promo. I don't know what the deal was. I think people were afraid a little bit of me saying, is he really going to let four strangers come over to his house? And that was the thing.

We were going to go. I'm going to bring you to ESPN. You're going to watch a show. We're going to get a workout in, which we may not have. I was going to take you out to dinner in West Hartford. And they were going to watch games in my basement, NBA games. And it was going to be you and four of your buddies. And ESPN was going to pick up the travel and everything.

I guess the weird part would have been, I didn't want you staying at my house. Like I didn't want to, I didn't want to wake up with four strangers there. So yeah, I'm sure we could have just had Uber or whatever. There might've been some talk maybe that it was like, so you're just openly saying you're going to take this guy out, but we were, I think somebody bid on it. So wait a minute. That's the other thing is that they didn't cancel it. Somebody bid on it. Somebody won it. And then I think they gave him another experience. I did think about with the all in challenge, adding this back in the mix, like making an option. But, uh, I haven't cause haven't because i the current situation right now as far

as having multiple people over the house isn't going to work too small so all right we'll leave you that have a great weekend bill and i back at it on sunday night and as always be safe Outro Music you