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From Ivan Boesky: The Wall Street Legend Who Crashed and Burned (with Rory Scovel) — Mar 18, 2026
Ivan Boesky: The Wall Street Legend Who Crashed and Burned (with Rory Scovel) — Mar 18, 2026 — starts at 0:00
That's very seldom I run into someone who I really think is just kind of a piece of shit. Yeah for the most part Everybody's just at their job, whether they're wildly famous or not and they're just trying to do the job and then go home and hang out with their family. It's just kind of our universal situation Well, you know what that means, Rory? That knowans you you' the piece of me. Oh my Godd, shit. This is an IiHart podcast Guaranteed human If you've been sitting on an inspiring business idea, consider this your sign to take action and make it official by creating a website using Wakes harmony Tell Wix Harmony what you want and it will build the entire site for you That's right, all just from your own text prompts And of course, everything can still be edited by hand if you feel the need for distinct specifications. I mean It's your website, your call. Try it at wix dot com slash harmony. That's wix dot com slash harmony Fonatics Fest NYC returns to the Javbit Center july sixteenth through the nineteenth for the biggest sports event weekend of the summer. See stars like LeBron James, Tom Brady, Eron Judge, Sean Cena, Jaylen Brunson, Serena Williams and hundreds more, featuring more than five hundred athletes and celebrities, live shows. exclusive merch, rare collectibles, Sonatics games with two million dollars in prizes, a full tailgate zone, and New York City's largest indndoor FIFA World Cup final watchatch party Fonatics Fest is the world's number one spports fan festival Get your tickets now Beticspest d. com. That's beticsfest d. com This is Chelsea Handler from Dear Chelsea. I'm going to be honest with you. I am online way more than I probably should be. And between me and everyone else at my house, we've got a zillion screens going on at any given moment. So when my internet slows down, it is a full crisis. That's why having fast, reliable internet that can keep up really matters and why you need optimum famously fast fiber Internet Optimum fiber blows flaky five G out of the water and keeps it cool with the fastest and most reliable speeds that don't slow when things heat up. And right now, they have the deal of the summer, just thirty dollars a month for five years. So don't wait, call eight eight eight for optimum. Visit optimum dot com or stop by your local optimum store today Famously Fast fiber for thirty dollars a month for five years. You can't beat it Terms apply, see optimum d. com for details Hello, and welcome to SnaFoo, your favorite podcast about history's greatest screw ups or If we're being completely honest, a show about the spectacular hubris of humanity The epic disasters it creates and the lessons. We like to pretend we can learn from them. I'm your host Ed Helmes. and my guest today is a very funny comedian, actor, writer and podcast host. He released his first comedy album, Dilation in twenty eleven and pumped out not one Three But six differentiffere stand upp specials The most recent of which, religion, sex, and a few things in between you can find on HBO Max. He's appeared in a variety of film and television programs with a particularly standout performance opposite Rose Byrne in Apple TV's physical, which is a Awesome show. By the way Yes, indeed. And he's set to appear in in a new ABC show called Do you want kids? And I think I also just saw a trailer that had you in it for My buddy Steve Carerell's new show, Roooster. That's right. So please welcome to the pod, the amazing Rory Scoveell. Thankk you very much for having me. I've got to say, Ed, I have waited to see you face to face because this was the only way to tell you this U, but vacation potentially one of the funniest movies that I have seen and I Do not I don't know how long But I have not seen a comedy where literally every five minutes I sort of need to pause the movie to collect myself And I have shown so many people that movie and I tell them you will cry laughing. And it's so true. I love that movie so much. You are this you're gonna to make me cry right now. You're really touching me and I'll tell you why because I and the writer directors of that movie have long felt that that movie Like we are so proud of it. It is It's a movie we loved making. we love the product And it just didn't capture the audience that we that we hoped for. And so when I get these little nuggets of affirmation like that, I really appreciate it. That really means a lot. You guys should absolutely be proud of it, justust given the fact that it's not comedically predictable. It's not hacky, it's not like cringy comedy that you can find out there, which is fine. The fact that it actually is just so moments of that car is so stupid. The car is so funny. There's a key fob With a million buttons on it and Christina Applegate goes, is that a swastika? And I and I just like, yeah, we won't use that What is that What It's great. All right, well, enough about We're here to talk about you. First of all, I've actually known you a long time. notot well. We've bumped into each other over the years But I have a very u Borderline offensive question for you, which is Do you say your last name Scoveel or Scovill I say ScoOvil, which okay, I'm gonna gohe and say is correct. But that versions of it. R Skvel. Yeah, Skval. Skival. Skivill. Skel. Skvel Good. good because I am Southern. so I have all these little like contractions. I say I say things. I like my friend Eleanor, I say Eleanor Yeah and Scoval. Yeah and That sort of thing. So but I'm always conscious that I'm probably doing it wrong as well. Where are you from originally? The south from South Carolina, Greenville. Oh, right on. Eleanor is exactly right. Even though it's spelled with an O,'s pronounced with an I or even an apostrophe. an apostrophe R. Eleanor. Yeah Eleanor. Yeah. That R comes in quick You're rapidly becoming an American treasure and I love This is the best podcast I've ever been on We should just do this. This is called buts up. We just just compliment each other boys with booys. How great are you? That's what this is called. No, but it's fun when when I have people on that I think are awesome like you. So thank you. You have a new podcast also. You're getting into this space. starting to horn in on my space's a little bit What is it? Tell me more. It's a show called Crimeeless. I do it with journalist Josh Dean. and yeah, he basically, not so unlike this show, just in the world of like crime stories and stupid criminals throughout history and throughout the world Josh kind of reads me a story about, can you believe this bonehead, you know criminal story and I'm just hearing it for the first time and commenting on it. and And I love it. I'm shocked every time That I mean, I'm not shocked and I am shocked that ninety five percent of the stories are from Florida But that is just that's just the reality of it. But yeah, it's out now and it's been super fun to do. and Josh is a great co host. Cool I am psyched to check that out. And it's also a perfect segue into what we're about to do. I'm about to talk to you about this snafoo. and in this particular case, it is also a crime Perfect Have you seen the movie Wall Street? I've seen the movie Wall Street. Okay, with Michael Douglas and Charlie Sheheen, Charlie Sheen, Darryl Hannah, it's Oliver Stone movie. it's phenomenal. So the guy that Michael Douglas plays in that movie who's like a corporate raider and like a Wall Street tycoon. he's based loosely, but he is based on a real guy Is this does this ring any bells for you? No, I don't think I I don't think I was aware of this. No So this is a Wall Street legend of sorts. It's just one of those really epic stories about a man who rose from rags to riches and then plummeted from riches to an orange jumpsuit. Our man of the hour is Ivan Boski And he was considered widely thought to be the direct inspiration for Michael Douglas's very slippery eighties villain Gordon Gecko. Yeah. We have we have a photo of Mr. Boski here It just seems I think that I've seen other pictures of him where his eyes look normal. So I'm just gonna guess that's a weird's either he's either winking or or it's just one of those weird weird moments that that cameras get. But there's a slickness to this guy and look at his skin. he's got game show host vibes. He does. He kind of looks like he'd be fun to hang out have a beer with. I'll be honest That's right. Well, we're going to learn why he might not be somebody that you wanted to hang out with. Also funny funny footnote, he's wearing a black suit and a white shirt in this picture. and That That was his go to every single day. he and someone asked him at one point, why do you wear the same suit and shirt every day And he said, I have enough big decisions to make every day. This is one I can just take off the list, which is funny because Einstein is also famous for that Albert Einstein always wore the same suit and shirt for the same reasons.'s just like Take it off your plate. right? It makes sense. It makes I don't know if you do that. I don't do it for those reasons. When I wear the same clothes, it's clearly like a lazy sort of. When I wear the same clothes every day, it's problematic. It's a bit of a red flag. They're staying It happens. you explain right. Here is Michael Douglas's famous piece of dialogue from Wall Street He's giving a big speech to stockholders meeting for a big company And he's he's walking the aisle with a microphone and he he's tons of gravitas. and he's just saying greed. for lack of a better word is good Greed is right. Greed works. Greed clarifies, cuts through, and captures the essence of the evolutionary spirit. Yeah Yeah I think we know now. The state of our politics that he was right. is going great. It It's going so good. He's all right. What he left out is And all of that sucks.ike Yeah And that the consequences of all of this is not good. The endgame of this is devastating.. Eactly. So today, we will find out what that spirit conjured throughout the eighties. Of course, your show physical takes place in the eighties. do you Well, how would you capture the spirit of the eighties. What do you how do you describe it I don't know. I feel like that's almost a good I feel like that that's why there's something to his speech in that movie because it's almost like the eighties was like you can get up and you can create your own future and greed and wanting to do it and having to step over people to pull it off is a is a great way is a great start. And then the other side of it feels like Cindy Lopper and Madonna, which I feel like I identify with more in my spirit of what I like to envision of the eighties. But as far as business I think it was like that Also, I'm just gonna say a word that I associate with the eighties Cocaine Yeah Lots of it And that that's what crossed the aisles That's where the art community and the community found common ground. Amen All right, well, let's get into Ivan Boki a little bit. He starts out modestly, born in nineteen thirty seven. He grew up in post war, Detroit, the son of a Russian immigrant who ran delis and old school brass rail bars, which is those blue collar taverns fueled by rye bread cigarettes and cheap liquor. And a little fun Detroit footnote Boski attended Mumford High School. Does that mean anything to you No. Mumford High School later achieved pop culture immortality thanks to Eddie Murphy's gray sweatshirt in Beverly Hills cop. Oh Yeah. Okaykay. He' a Mumford sweatshirt. I love that. Well so Boski actually went there. From the sounds of it, Ivan strove for more. There's a peculiar quote from his second cousin, found in a Time magazine article. He had this capacity for single mindedness. He drove himself mercilessly as far as exercise goes. That's the most unrelatable sentence I've ever he Yeah, goes on to talk about how he does hundreds of pushups, which is odd, but I guess speaks to like a driven sort of character as a young man. Have you ever watched someone with incredible focus and drive and just thought, that's really impressive before realizing that's the energy that also is wrecking everything. Yes. But also they almost seemed you can't picture them laughing or saying something originally funny or you just they almost feel like carbon copies of carbon copies of people. Yeah, I know what you mean. I don't understand that drive. It's a little bit Elon Musk's arc, right? Yeah. feels like he was this incredibly inspiring kind of relentless innovator and then whoa, whoa, it just went So Yeah, so far over the The line Yeah at some point. Yeah, the ambition gets taken away or takes off way too far I also think some kids speaking of the eighties, I think you watched movies. I think there's a lot of us that saw something like the karate kid and wanted to be Daniel Lausso and then some people We're like, no, I want to be Johnny. I want to be the blind headaded dude Who's clearly a bad guy. And it's you see that in their lives You That's so interesting I mean, I definitely when I saw those guys jumping motorcycles around in their skeleton Halloween costumes, I was like, I definitely want to be that. But when Daniel Lausso like kicks him in the face with the swan kick. I'm like Yeah That's who I want to be. You're like that's the guy Yeah. Yeah. While in school, Bosky married Sima Silberstein in nineteen sixty two, daughter of real estate lawyer and hotel tycoon Ben Silberstein We could probably actually do a whole story on Silverstein. He is fascinating in and ofself himself. But here's a quick anecdote. Allegedly, when he was younger, he was turned away from the Beverly Hills Hotel On a subsequent visit with his youngest daughter, Murel, she exclaimed that he thought He should simply buy the place. And so He did. Yeah. I guess it's kind of a fuck you. He just bought the hotel for five point five million dollars in nineteen fifty four. Oh my God. That's that's Just over sixty six million do today, and I think it's worth a lot more than that. Safe to say Bosky was well aware of this class differential he was marrying into and really wanted to prove himself. After graduating from the Detroit College of Law, he drifted through a series of soul sucking gigs, law clerk, accountant K of rinse and repeat None none of it sticking, none of it satisfying Then his father died in nineteen sixty four Boski took over the family's last brass rail bar and rebranded it Le Club a Go. No. and the broght ends are like topless dancers made it a kind of tadry salacious affair. And of course it was bankrupt within two years. Yeah The brass Ril bar is so fun. Every time I like hear that, I think of Rudy when his dad threw him and his brother out of the bar when all the guys were off work at the mill and they were just drinking at the bar and then Rudy was Sean asked him was doing something and his dad told the owner to throw them out It liives in my mind forever because I thought, why don't you just tell your son to leave the bar? Why does the owner have to now get involved and throw your kid But I always picture that Five PM blue color. guys in their their destroyed clothing from working at the mill just having beers and it just seems So cozy. Now introduce Like like a like a burlesque dancer to that Y vibe Yeah and it was not successful This went it went bankrupt in two years. Boseki at the time was not exactly happy. His father in law would constantly let him know how unhappy he was with his daughter's choices. He nicknamed Ivan Bosky Ivan the Bum and openly referred to him as a Nerdwell who would amount to nothing, which is K of a brutal way to talk to your son in law. I feel like Ivan Brokki was right there for the taking. and he went with the bum. Yeah Hh You're going to be a tough father in law. I'm excited was that kind of nicknaming. Yeah for the nicknames. This is an interesting one. How much of a person's identity or you know, ambition gets shaped by all the people shouting at them that they're a failure Of course. Oh my God. abbsolutely. I mean, that's like the core of representation in entertainment and how you're represented like in entertainment and who you are that you, you know When you start to identify with people who look like you or you feel like you relate to, like that's what inspires the idea that you think, well, I'm just meant to be a failure or I can be a success. You know, for sure, but you're right, like criticism like that, it starts to become your reality Yeah, it can either it can either destroy someone or like Give them like very intense fuel. Yeah. And and I would I would also say that's probably not like good fel healthy fuel. ionalventional fuel. Right. It's like, I want to be a success, not because I want to like have nice vacations with my family. It's because I want to make this other person feel like shit. Yeah every d at a hotel when they refuse service That really puts me in my place. I couldn't do that at a gas station or a I wentro to a fast food place and they disrespected me I' be like, you just wait, I'm going to buy this place. I'm going to need about twenty years just to kind of get the green together, but I'll you. Well, needless to say, Boseki was extremely motivated in part, probably to best his father in law. He and Sema moved to the Big Apple. Now Rory, that is a Wall Street term for New York City. H Okay, you said we were gonna learn today. You said that The big apple, makeake a note of it Now, I guess father in law Silverstein was at least kind enough put them up in a Park Avenue apartment, even bankrolled osky's first company with seven hundred thousand dollars This was nineteen seventy five and Ivan had found his passion and promise. on Wall Street. He was an incredibly hard worker allegedly clocking twenty hour workdays. This is an interesting thing that sort of emerges in a lot of biographical material about him. He never ate. He would go to these big, you know, functions and meals or like host big things, dinner parties and this that And like no one ever saw him eat. He would have like a grape or like, yeah, little nibbles of things. And he was like, as we mentioned before relentlessly working out. just like a very intense guy and also never slept It's just one of those weird vampire dudes who can like Like I have my sleep tracker and if it's like less than eight hours, I'm just like, oh God, this is gonna be a hard day. Yeah, yourour day's ruined. sir. I go into the day already like A I'm on half a tank. you're like, if I could just get three pastries in my body, I bet I could find some fuel in there Fonanatics Fest NYC returns to the Jabbit Center july sixteenth through the nineteenth for the biggest sports event weekend of the summer. S stars like LeBron James, Tom Brady,raron Judge, John Cena, Jalen Brunson, Serena Williams, and hundreds more, featuring more than five hundred athletes and celebrities, live shows. exclusive merch, rare collectibles, Sonatics games with two million dollars in prizes, a full tailgate zone, and New York City's largest indndoor FIFA World Cup fininal watchatch party. Sanatics Fest is the world's number one sports fan festival. your tickets etxpus d. comot That's b netxpest d. comot The Declaration which is full of these beautifully rendered you know, sentences and paragraphs about enlightenment ideals. does also have this darker history to it Why is it important for the darker part of the Declaration of Independence and the American Revolution Why is it important that Americans know about it Well, if we don't understand, The full context in which our nation was founded We won't understand the full context in which our nation now finds itself. I'm Rebecca Nagl, Gohin Daadon, Jekca Yetli, Gay, citizen of Cherokee Nation. Are you guys big chef fans? Hell yeah. This is First America, the true story of how the United States came to be. How we got to this present moment Listen to First America on the IiHart Radio app, Apple podcast, or wherever you get your podcasts I'm Mgisha Tet and I'm back with a new season of the podcast Skyline Drive. This time I'm diving into a rabbit hole of peptides, organoids, blood boys, blue zones, and brain replacement to try to understand what this longevity obsession is all about and what it really means to live forever For all of us I learned about some rad science. I can make a brain for you And then we can test what draw is the best for your brain opposed to his brain Here are some hard truths that I would expect Indians to age faster, but I did not expect it to be almost a four to five year acceleration. and get myself into a world of trouble I'd say probably start bone smashing. That doesn't work. Make it look more defined. They say it works. I don't know Listen to Skylland Drive How to Live Forever on the Hart Radio app, Apple podcasts, or wherever you get your podcasts Okay guys, Paul Versey here and I wantan to talk to you about Paul's bestest podcast.m Will Furrows, Big Money playlayers Network and IHart Radio. I sit down each week with a special guest and we discuss the absolute best of things David It's that and then there's everything else. He would just shout one line It would murder. Marie Hunch! Hilur. Let's talk about the best moments that we had on the road I would love a cocktail. Do Joker get last row Widle seat on the Southwest Airlines flight? Joe, how was you fight. It was qu. The guy on state on the field. The player thought Joe was his former coach and he hugged him and hugged him and Joe just went with it ' they the guy goes, what are you doing here? cooaching and Joe just And you walk in and it is bananas. I mean, it's a feast for the eyes and I was like, it's like it's not my thing either but we're here Top athletes, chefs, musicians, everybody. Listen to Paul's bestest podcast on the IHart Radio app, Apple podcasts, or wherever you get your podcasts Ivan Boski was very dedicated to sort of carving out his place on Wall Street He was not a traditional investor. He worked in a space known as arbitrage. So traditional investing is like pllant a tree, you buy a stock and you believe in the company and you hold it for a long time, believing that this company will grow Stockbrokers will research companies in order to sort of know which companies have the best chances of growing and accumulating value. Arbitrage is a different kind of investing It's all about timing fast it's fast in and fast out. So you buy something that you think is temporarily underpriced and then sell it the minute the price corrects. So it kind of works like this. You would find a small company, something that has like a sort of special or obscure value. Maybe it's a product or a service or an expertise of some kind. but it's something that a bigger company would want Then you figure out that a takeover by this bigger company or or any number of bigger companies is likely before the public catches ono this And you buy a ton of shares of this small company while the stock price is relatively low. then When this takeover happens and is announced, the stock price jumps and you immediately sell. It has nothing there's no loyalty.'re not there's no belief in the company. You're just trying to spot the moment when the price is about to change and be there first. It's one of the most risky kinds of investing. and at the time Most arbitrage players were very cautious. smallmall bets, careful math, lots of hedging Bowki was not built this way. He went He just went big. He pushed harder. He took huge risks that others wouldn't touch. And as the seventies sort of turned into the eighties, this all of his bullheaded bluster turned him into a force of nature. He was also incredibly smart and gifted at, you know market analysis. And somehow, Ivan Bosky just kept Every time you say Bosekke, I only picture Michael Douglas anyway eating honestly, just eating the raw meat that he gets at that restaurant in. That movie was so good. I need to rewatch that. I mean when he stands on the balcony at the apartment and Charlie Sheeen just yells out to the city, Who am I It's like We've all been there. B there Did you live in New York City?? I lived there for four years and then What When was that? I was there zero seven to twenty eleven right after me. I was there ninety six to two thousand Yeah, seven, basically. I was there when I lived there, I was at all those Delclos marathons watching you guys those that one that venue is incredible. but those are some of my happppiest memories from comedy, just going and watching Am insane improv at the Del Close marathon like three in the morning Yes. It was so it felt so punk rock. one hundred percent. Right? And that was like, that's what I loved about it is like there were There were a lot of like Like I've always been pretty nerdy and like, clean cut, but like I have value Rck I value the the the the weirdos and the people on the margins. I just think that they're such a marvelous part of our culture and society. and then you have an institution like the Upright Citizens Brigade that Um, just brings it all together somehow. And you have like buttoned up comedians pererforming next to like just the wildest performance art wackadoos. Yeah. And it's just pure joy I like one hundred percent. agree We're now in the midst of the mid eighties We're talking Lycra leggings. Tom Selx mustache And everyone's asking, whereere's the bef? because of the u Wendy's commercial Yeah, it was Weindy's. Oh, I don't know. is that where I came from? Where's the beef? Yeah, It's like a little old lady opening up hermburger and it's like a tiny little meat patty. Yeah. In nineteen eighty one, the Ivan F. Boski Corp was rolling in it, making more than one hundred fifty million dollars in profits from short runs on CBS, Gulf Oil, and Konaco. According to Vanity Fair, one hundred fifty million dollars was more money than Ivan's father in law ever had. So I guess some nice warm comfort there That's evolution of the human spirit right there. Yeah it above that number. Oh, I just gota win. I just gota win. Yeah. At whatever cost to my soul, it's fine So Ivan is raaking it in. By the spring of nineteen eighty five, he was reportedly the highest paid broker on Wall Street with a net worth of over two hundred eighty million dollars, which is nearly eight hundred forty million doars in today's dollars, which I just want to point out eight hundred forty million dollars, like in today's money is not considered you know, the The crazy wealthy. The crazy you have to be a billionaire to be a crazy wealthy And and that's a comment on like in the eighties, as much money and excess as as these guys are engaging in, we're still not in a culture with the wealth gap that we have today Yeah, right? The wealth gap has just like exxploded exploded since the eighties, but it's just interesting to me that we're talking about these guys as if they're Jeff Bezos or or Elon Musk or Zuckerberg, but they're not even close to that. by comparison and yet still titans in their own in their own time. Yeah the day, they were that. And I think it's that trickled down economics of the eighties where people are like, no give all this money Give it up here and you'll get it back They'll come back to you. Yeah. I know what you mean, like that wealth gap is massive now And I think there's something to the eighties of like, yeah, this is what really Lit the letit the fire Yeah, Boseky held a spot on the Forbes four hundred list of America's wealthiest people. He ran his firm with real intensity ferosity, orchestrating like a real high pressure operation of roughly a hundred employees. His self promotion was legendary. He hired his own PR firm to help promote himself. His self promotion tour included press for his own book, written with the aid of journalist Jeffrey G. Madrick called Merger Mania Arbitrage, Wall Street's best kept money making secret. And u yeah. You know, that big old shade eating grin right on the front. It's so funny like a book like that, you're like just like just considering where I grew up in like South Carolina, like my dad worked at the post office. This is like Is anybody at the post office You read this money mania ar Yeah, Merger Merger mania. Merger manania Yeah book about Wall Street? Yeah. I feel like you just explaining investing in companies, getting in and getting out is probably the biggest lesson I've gotten I like Wal stet What it even is to me, it's just a circus that I can't understand. Yes. I agree. I find I find it all very like brain Fanatics Fest NYC returns to the Jabbit Center july sixteenth through the nineteenth for the biggest sports event weekend of the summer. S stars like LeBron James, Tomrady,raron Judge, Sehn Cina,aylen Brunson, Serena Williams, and hundreds more. feeaturing more than five hundred athletes and celebrities, live shows. Eclusive merch, rare collectibles, Sonatics games with two million dollars in prizes. A full tailgate zone. in New York City's largest indoor Fiva World Cup fininal watchatch party. Fanaticsfest is the world's number one sports fan festival. Get your tickets now at fanaticsfest dot com dot That's fanaticsfest dot com d The Declaration which is full of these beautifully rendered You know, sentences and paragraphs about enlightenment ideals. does also have this darker history to it Why is it important for the darker part of the Declaration of Independence and the American Revolution Why is it important that Americans know about it Well, if we don't understand, The full context in which our nation was founded We won't understand the full context in which our nation now finds itself I'm Rebecca Nagel, Gohin, Daadon, Jekca Yetleli, gay laa, citizen of Cherokee Nation. Are you guys big chief fans? Hell yeah This is First America, the true story of how the United States came to be and how we got to this present moment. Listen to First America on the IiHart Radio app, Apple podcasts, or wherever you get your podcasts I'm Mgish Sa Tet and I'm back with a new season of the podcast Skyline Drive This time I'm diving into a rabbit hole of peptides, organoids, blood boys, blue zones, and brain replacement to try to understand what this longevity obsession is all about and what it really means to live forever for all of us I learned about some rad science. I can make a brain for you and then we can test what draw is the best for your brain as opposed to his brain. Here are some hard truths. I would expect Indians to age faster, but I did not expect it to be almost a four to five year acceleration. And get myself into a world of trouble I'd say probably start bone smashing. That doesn't work. makeake it look more defined. They say it works. I don't know. Listen to Skylland Drive, How to Live Forever on the iHart Radio app, Apple podcasts, or wherever you get your podcasts Hey guys, Paul Very here, and I wantanna talk to you about Paul's bestest podcast. I'm Will Furrows, Big Money Players Network and I Heart Radio. I sit down each week with a special guest and we discuss the absolute best of things. Dav It's that. and then there's everything else. He would just shout one line. It would murder. Marie Hunch! Hil. Let's talk about the best moments that we had on the road I would love a cocktail. Do Joe get last row Widter seat on a Southwest Airlines flight? Joe how I was your fight? It was qu The guy on from state we were on the field The player thought Joe was his former coach and he hugged him and hugged him and Joe just went with it they know the guy goes, what are you doing here cooach and Joe just go And you walk in and it is bananas. I mean, it's a feast for the eyes and I was like, it's like it's not my thing either, but we're athletes, chefs, musicians, everybody. Listen to Paul's bestest podcast on the IHart Radio app, Apple podcasts, or wherever you get your podcasts In nineteen eighty six, Bosky was invited to provide a commencement speech at the University of California at Berkeley, Has School of Business. And this is where that speech that was the inspiration for Gordon Gecko's infamous framing was derived. But it's not exactly the same as Gordon Gecko's. What he said is Greed is alright, by the way. I want you to know that. I think greed is healthy. You can be greedy and still feel good about yourself This sounds like a cult leader It's weird. You know what it has echoes of this this this all this stuff emerging from both the Christian nationalist movement and Elon Musk where it's like Empathy is bad. Right. Yeah, yeah, yeah. This is saying the same thing in the sort of inverse You read is good self interest is good. It's very An Randy in that way. likeike It's just It's very Discard the seven deadly sins and move on. Greed is okay. It's fine. Right It' fine, right. Yeah, the Bible literally tells you that this is a deadly sin. Yeah. It's oneing this is destructive to you personally and to all of people. But if you wna have an elevator in your house, you gotta have a little bit of it Yeah, this is I love the last sentence. You can be greedy and still feel good about yourself That's awesome Okay, so all of this is going on and all of a sudden. Record scratch Just months after riding high, it all unraveled. On november fourteenth, nineteen eighty six, Ivan Bosky pleaded guilty to conspiring to file false trading records, is compplicated way of saying insider trading. Okay basasically Time magazine put his grinning face on the cover and dubbed him Ivan the Terrible Which is a little derivative, but okay. stillill better the knife and the bum from the father. Sure U not and not as good as Ivan Brokki. Right. That's right. One minute this guy is Wall Street royalty. The next he's a cautionary tale and the high rooller era was over. He is headed to Prison Do you think that repeated success always turns people into egomaniacs or like just disasters Is it possible to remain humble? I think it's possible to remain humble based on I think how much you've acquired But person before you've reached that success. For instance, I think a lot of people in our industry who find fame or fortune later in their careers tend to be a little more chill and fully aware that life is fickled and it can go away. And yesterday I was doing this job and today I'm grateful I've got this one. But I think when you have it at a young age and nothing against those people that get it at a young age because they are missing that That sort of educational step. I think a lot of times they can come off as awful people And maybe if something happens and they turn a corner and they change, but you definitely see it in people who come from a certain background. I think it's just learning the value. M of things sure, but I think people can remain But I tell people all the time that like friends back home or people ask me if I've worked with someone They always want to know if someone's a jerk. I go, I gotta be honest, it's very seldom I run into someone who I really think is just kind of a piece of shit. I know for the most part, Everybody's just at their job whether they're wildly famous or not, and they're just trying to do the job and then go home and hang out with their family. It's just kind of our universal situation Well, you know what that means, Rory Dad know you're the piece of shit. Oh my God, shit. If you can't actually see how much other people are a piece of shit, it means you're a giant piece of shit. U fuck, I just thought they were so fun. I looked up to all of them I mean, our industry obviously, is a very hot crucible of all of this stuff But I think also just looking into the business world, you know, and seeing especially these thesech modern tech Titans and your Jeff Bezoses and so forth, it's really amazing. You can chart their values and their appearance Their physical appearance, how it changes over time with their power and wealth and it's It's very disheartening. You know, the notion that absolute power corrupts absolutely Um, really seems to hold a lot of water Yes hundred percent. Yeah. And also, you do wonder like in the origin story, of these billionaires or tech titans. You do wonder like are they coming from a place of like sort of like Ivan. Like wasas it vengeance where they like, Ohh, I'll show this world I value And I'll become this because I think the world has treated me This way, there's such an irony too thenen becoming a billionaire who kind of in many ways runs the world and not having compassion for who might also be what you once were, but instead being like, No, those people are trash. Yeah likeike what? Well, that's what you right We have pictures of you. Yeah. We have We have pictures of Jeff Bezos as the sweetest little nerd. Yeah. so So bizarre I think that's why I like the brass rail bars. just keep me in that pocket where I can just go get a beer glass. I don't want to run the world Don't limit yourself, Rory. I have a lot. You can't We want you to run the world. I mean, it'd be more fun. Yeah, I'll tell you that. Burning Man wouldn't be just a week. It wouldn't be just one week in one location. I'll tell you that. Welcome to Rory's World All right, so how did we get here? How did this epic crumble of a Wall Street Titan occur? It starts in nineteen eighty two when Aboski took a brutal hit losing sixty million dollars on a bad deal That's a lot of money, but it was way more back then. suuddenly This guy who always seemed to be one step ahead was underwater and that's when The lines started to blur. The pressure mounted betets got darker and Boski crossed into insider Trading Is there anything more human than trying to recover from a humiliating loss by just immediately making a series of worse decisions It is true. It's our common bond. It's such's so it makes us all human. Yeah. Even on a small scale, I just feel like likeike if you, you know You spill something in your lap and then your panic makes you spill like someone shit. God. Yeah So now it's nineteen eighty five U and Bosk's having an amazing year. And so were a lot of other savvy traders all raking in millions. In fact, they were winning so hard that it was beginning to feel an awful lot like somebody knew something somewhere that somehow was tipping off those some ones with some slick insider gravy Basically, regulators began to suspect that the stench of insider information was bubbling up from the sewage of these multimillion dollar deals. Quick Wall Street check in. Do you understand what insider trading is actuallyually I think so. For instance, your example earlier about a business being acquired by another business and finding that out and deciding, all right, let's buy low so we can sell high because we know it's coming. Right. So the honest way to do that is to like just do your research and your homework and try to figure out which companies are going to get bought The illegal insider trading version is for someone who knows a company is about to be bought to tell to like whisper it to you so you can then go and buy those shares and then as soon as the company's bought, those the value of those shares just like rockets up. Yeah. It seems like it's very legal now because it seems to occur quite often including with Iran White House directly Well it's so ironic. and of course within Congress so many Congress people have so much access to what is considered inside information. Yes because they know about laws that are coming that will dramatically affect these various companies and industries and they can invest accordingly do and it is so ark And the irony is that the Securities and Exchange Commission, which is tasked with catching these people and and bringing them to justice They now have incredible analytics and, you know, tools to catch people doing this stuff. And to catch sort of suspicious activity and then be able to research massive amounts of data more quickly. like the tools to catch these people are better than ever. and yet it feels like we're just swimming in it more than ever, which is insane. All the time. Yeah ye. Yeah. So these investigators back in the day, they thought they smelled something and they were exactly right. According to Fortune It was in nineteen eighty five that the SEC began to unravel a tangled web beginning with two Merrill Lynch employees in Venezuela The SCC managed to connect them to high profile investment banker Dennis Levine, among others. and it was Levine who then gave up the gossip on Gordon Geck, I mean Ian Ivan Boski. Levine had struck a deal to cooperate with the U.S atttorney of the Southern District of New York Who was, wait for it? Rudy Giuliani. Oh Wow. This of course is pre Mayoral pre disbred, pre four seasons tootal landscaping Giuliani. four seasons thing will live forever. Oh my God, just. to then act like you meant to do it. The abject stupidity of it all and the so Shocking. Yeah And shocking to think there was a time when he was actually on the right side of things. L this was he was actually doing good work as the attorney for the Southern District of New York. It wasved. Yeah So Levine admitted to providing Boski with nonpublic information about pending deals And this was enough to bring Bosky in. and they caught him red handed. thenen interestingly, Bosky would make a deal of his own with the Department of Justice And this would lower his prison sentence from five years to three. Not only did he wind up paying a hundred million dollars, which at the time was a record high penalty for such criminal activity, he also agreed to tattle on other traitors by secretly recording them and turning them over to authorities He's one of those guysy. He ar. He arked. He arked He rurned. He He did he did bad things and then tried to get off the hook by doing bad things to other bad guys, I guess. Yeah. it's very morally ambiguous. You how to feel about it. Yeah, because you don't like rats. Rats are like they're the worst. They're turn coats, but like oftentimes they're on the morally and ethically correct side of things. Yeah, should you actually should admire them, but you're like, no. no. Now I respect you even less. Yeah. You should have been the criminal to begin with. Yeah But now you are one, leave the other criminals alone I think it it's the cynicism of it, right? That's's like it's like it's not coming from a good place. Right? Yeah. Yeah. there you go. The fall from Grace was swift and merciless. In the nineteen eighty six Times article, an unidentified friend of Bosk's is quoted He wanted so much to be accepted and he thought money was the only way That's kind of poignant, actually. Another investment banker also unidentified is quoted as saying I always knew he was a rat That's in Time magazine. I always knew he was a rat. That's like so Shakespearean. For to see money in your future. The other guy bit so poignant and so intelligent and deep.
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