Scamfluencers - Andrew Caspersen: Rich People Problems | 178

Episode Date: September 22, 2025

Andrew Caspersen seemed to have it all: Ivy League credentials, athletic talent and a trust fund that fueled his reputation as a rising star in finance. But behind his polished image was a spiral of drinking, gambling, and reckless bets on the stock market. Soon, his risky trades won’t just drain his own fortune – they’ll cost his friends and family millions.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Scamfluencers on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/scamfluencers/ now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, scam influencers, listeners. If you're as hooked on these jaw-dropping schemes as we are, you'll love Wondry Plus. Think of it as you're all access past the world of scams. Add-free episodes, early access, and exclusive deep dives that uncover even more shocking details. Don't just listen. Emmerse yourself in the chaos with Wondry Plus. A note for our listeners, this episode contains references to suicide. Please listen with care. Sachi, we always talk about how we disappear if we ever got truly wealthy. Why do you think it is that some people just can't stay out of trouble even when they have every resource at their disposal? Ego. People need to have everybody know that they have all this money and that they have all these resources.

Ego. Root of all evil. Yeah, it couldn't be me. I truly do thank God every day that I'm marginally employed and I don't really have the resources to solve sabotage like that. It's a beautiful incantation to say every night to yourself, Sarah. Yes. Well, today's story is extremely frustrating.

It's about a guy who had an addiction and access to infinite money and was surrounded by people who don't think feelings are real. Get ready for the story of a near-fatal case of affluenza. It's November 2015 and Andrew Casper, is meeting with an old college buddy. They both went to Princeton, and you can really tell. Andrew is a well-dressed white man in his late 30s. He kind of looks like William H. Macy if he was also a Kennedy and grew up playing lacrosse.

Do you see it? Yeah, this is the whitest man to ever white. He looks like a potato with eyes, nose, and mouth carved in. Yes, and we don't know exactly where this conversation took place, but maybe it was at the Princeton Club, a private space in Manhattan for alumni. They're probably at the bar. Andrew has always been a heavy drinker,

especially when he's stressed. And he is definitely stressed out right now because this isn't a casual hang. Andrew is pitching James on a business deal. James is the managing director for a hedge fund called Moore Capital, which handles tens of billions of dollars in assets. James also invests money from the firm's

much smaller charitable foundation worth nearly $200 million. That's the fund Andrew's targeting. Andrew explains that he's offering the foundation a completely secure investment opportunity with 15% quarterly interest payouts. And he says if James ever wants the money back, he can get it with just 90 days notice.

Oh, this is a classic scam flinters set up. We've heard this before. It's so classic. It's like they've all been reading the same book. Yeah. And we know this. called promise should come with the biggest red flag.

Even Bernie Madoff only offered his clients a 10% return on their investments. But Andrew hopes that James will put his trust in a fellow Princeton Tiger. And he does. James offers Andrew $24.6 million from the more charitable foundation

and throws in $400,000 of his own money to make it an even $25 million. This should be a big win for Andrew. but he's more relieved than thrilled. For pretty much his entire adult life, Andrew has been compulsively playing the stock market like he's in Vegas,

a habit that leaves him constantly on the edge of financial ruin. Two months ago, he siphoned off $9 million from his employer in order to cover his debts. Now, he's going to use a chunk of James' investment to pay back the money he stole, and the rest will be funneled straight back into Andrew's gambling habit. Andrew was born rich, so rich that for years he's been able to lose millions of dollars without it affecting anyone but him. But his addiction has grown out of control, and he's about to start taking money out of his friends and family's pockets to feed it.

Andrew's testing the outer boundaries of privilege, and when he finally crosses the line, all hell will break loose. Grab a coffee and discover a coffee. Vegas-level excitement with BetMGM Casino. Now introducing our hottest exclusive, Friends, the one with the Multi-Drop. Your favorite classic television show is being reimagined into your new favorite casino game, featuring iconic images from the show.

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19 plus to wager. Ontario only. Please play responsibly. If you have questions or concerns about your gambling or someone close to you, please contact Connects Ontario at 1-866-531-2,600, to speak to an advisor free of charge. BetMGM operates pursuant to an operating agreement with iGaming Ontario. It's your man, Nick Cannon, I'm here to bring you my new podcast, Nick Cannon at night. Every week, I'm bringing out some of my celebrity friends and the best experts in the business

to answer your most intimate relationship questions. So don't be shy. Join the conversation and head over to YouTube to watch Nick Cannon at night or subscribe on the Wondry app or wherever you get your podcast. From Wondery, I'm Sarah Haggy, and I'm Sachi Cole, and this is scamphalancers. Come and give me your attention, I won't ever learn my lesson, turn my speakers to 11, I feel like a legend. Andrew Casperson was raised in a family that valued money and appearances above all else.

So when Andrew develops a gambling problem in his 20s, his dad is happy to pay off his debts as long as it means he can sweep Andrew's unhappiness under the rug too, A combination of generational wealth and waspy emotional repression will send Andrew spiraling for decades. And when his scams finally do come to light and his secrets are exposed, they reveal the ugly underbelly of how American wealth operates. I'm calling this Andrew Casperson, Rich People Problems. To understand the world that Andrew lives in,

we have to start by explaining how his family built their fortune. It all starts with Andrew's grandfather, Olaas. Olas emigrates from Norway to the U.S. in 1912. He works a series of odd jobs, including as a stenographer for a company owned by the Rockefellers. Eventually, he makes his way into finance, and by 1935, he's pulling down nearly $32,000 a year, or about three quarters of a million dollars today. His company is ahead of its time. It basically invents the subprime mortgage in the state.

60s. Well, we should thank him. Everybody loves the subprime mortgage. Definitely worked out. No problems there. Yeah, I mean, listen, you should just lie about that being in your family history. Yeah, I wouldn't brag about that. Well, as Olas climbs a financial ladder, he starts paying more attention to the social ladder. It's very important to him that his family keeps up appearances and looks like they belong. So even though his wife is Jewish, they raise their children Protestant. In fact, their son Finn, Andrew's dad, spends his entire life hiding his Jewish roots. Finn is born in 1941,

and he's a chip off the old block. He starts working for his dad's company in the early 70s. He's named CEO after just four years, and three years after that, he's wealthy enough to literally buy an island in Florida. Finn makes being rich his whole personality. He dresses like a dandy in top hats and suits. His favorite sport is something called

four-in-hand, horse-drawn carriage riding. By the time Andrew is born in 1976, Finn owns at least three houses in some of the wealthiest zip codes in America. He's also a big-time donor to fancy schools all over the East Coast. There are buildings named after him at Harvard Law School,

Petty Prep School, and Drew University. It's important to Finn that his largesse is literally being broadcast on a sign. Because Finn doesn't just like having money, he likes other people knowing it. A friend will later tell Vanity Fair that Finn, quote, needed to be the richest guy in the room.

What an embarrassing thing to need people to know about you. It's not even interesting. You may as well just take your pants off and show people your weiner. That would be less undignified. Yeah. Well, the Casperson's value

looking rich and happy over being rich and happy, and soon, Olas's obsession will bleed over into the next two generations and lead to their downfall. Andrew is the youngest of Finn's four children. As a teenager, he rose crew and becomes a star on the football team at Groton,

a fancy prep school in Massachusetts. Young Andrew has a pretty specific dream. He wants to play football at Princeton. And though he doesn't get recruited out of high school, he does get into Princeton and he's able to walk on. onto the team as a freshman. Things seem like they're going according to plan,

but it's Princeton football that presents Andrew with his first major setback. Andrew's boarding school was pretty strict, so he never really drank, but college is another story. At Princeton, he starts drinking heavily and regularly. He likes that alcohol makes him feel more outgoing and confident. And actually, he gets a little bit too confident.

In February 1996, he gets pulled over for driving drunk. Because his family is so wealthy, Andrew knows he can probably avoid the legal consequences of his actions. He's young, rich, and just needs a second chance. But then he gets called into his football coach's office. And while he can avoid a criminal record, he can't avoid what happens next. The coach cuts him from the team. Andrew should be devastated. In just a few short months, he's managed to achieve a lifelong dream and then blow it.

But he doesn't break down and he doesn't fight back or ask his dad to donate money to solve his problem. Instead, Andrew just walks away. He actually feels kind of relieved. He's been having a hard time focusing on football while doing all of this drinking. Having that commitment pulled for him means he's free to go all in on his burgeoning addiction. Here's how he describes that period of his life on the podcast, unintended consequences. No longer actually had to do the things in my life to make sure I could actually get out on the field. I could just focus on drinking.

I never even processed that this was a problem. And that lack of introspection and self-inventory, that was a defining characteristic of this whole dissent. I feel very conflicted about this, Sarah. I have a lot of empathy for people who have addiction problems. and he's using a lot of the language that you hear in like recovery circles, like, I get it. But also, what do you mean? What do you mean you were driving drunk

and the only consequence was that you didn't get to play a game? Of course, you didn't process that as a real problem because the consequence is so facile and childlike. When you're driving and you're drunk, you are driving a death machine. What do you mean? Yeah, that's exactly it. It's kind of like we already see this other world he's a part of.

Yeah. That is definitely not the same as ours. But Andrew does have a lot farther down to go before he'll hit rock bottom. Because drinking isn't his only addiction. He's about to discover the next great love of his life, gambling. Getting cut from the team doesn't affect Andrew's game. He starts dating a classmate named Catherine McCray, who goes by cat.

She's a smart, bubbly blonde, and she's from the same rarefied social class as Andrew. her family founded a prestigious Wall Street law firm. Andrew and Kat quickly gets serious, and everyone expects them to end up married. After graduating from Princeton, Andrew heads to Harvard Law. By this point, Finn has sold the company he works for

in a deal that people say made him a literal billionaire. With that kind of money lying around, it's no surprise that Andrew gets his first big disbursement from the family trust while he's still in law school. It comes out to $2.7 million. You might think that Andrew would sit on this money or at least spend it on something fun like a Maserati, which is a car, or an extravagant trip to Paris with his girlfriend.

Instead, he gets drunk alone in his apartment and decides to bet it all on high-risk tech stock. This is loser behavior. What's wrong with you? Well, you are forgetting that this is 1999. All tech stocks are high-risk. risk, but they're also frequently high reward. So it's not a total surprise that Andrew's first big bet pays off. Naturally, he keeps going. By July of the following year, he's nearly doubled his initial investment and turned that $2.7 million into $5 million. As we know on this show,

playing the stock market is essentially a form of gambling. But there are ways to mitigate the risks. things like researching your investments or moving some of your profits into safer, more secure accounts when you win big or making sure you don't put too much money in any one place. I'm pretty sure that's what people mean when they say, I need to diversify my portfolio. But Andrew doesn't do any of that.

Instead, he keeps betting all of his money on risky tech stocks. So when the tech industry crashes in the fall of 2000, he loses everything. For anyone else, this would be the end of the story. But Andrew's financial cushion means that being out of a few million dollars is just a drop in the bucket. And his family's waspy habit of saving face at all costs is about to become a huge liability. Because when Andrew confesses to his father, Finn helps cover his debts and tells him, just don't do it again.

This is so the early episodes of Succession, Kendall, the eldest son who's also in the throes of addiction and keeps having to go to his daddy to get him to, like, pull him out of trouble. Yeah, that was a good show, but not if it's actually happening. Yeah, it seems like something that is based on real life. Andrew has entered the cycle of addiction. He's still enrolled at Harvard, so his family is willing to write off his million-dollar losses. as a childish mistake. They're probably hoping he'll just get over it, but Andrew doesn't have any healthy coping mechanisms.

So when his seemingly blessed life takes a very hard left turn, he's only going to dig himself deeper into the hole. Andrew's dad may have insulated him from the financial consequences of his gambling, but no amount of money can protect him from his own misery. In the fall of 2000, he's having so much trouble focusing on school that he decides to take a leave of absence from Harvard. While he's away, Andrew lives with his parents in New Jersey. During this time, Andrew goes to see some doctors,

but he doesn't tell any of them about his drinking or gambling. One prescribes him an antidepressant, but it's unclear if he takes it. People who know Andrew will later describe him as viewing mental health problems as character flaws rather than illnesses. And keeping a stiff upper lip means that instead of treating his actual problems, Andrew gets diagnosed with Lyme disease and encephalitis. Maybe he has these issues, whatever, but I will say that, like, Lyme in particular is maybe second only to cancer

in the scamfluencer's illness canon. These people are always getting Lyme in the same way that they're always getting cancer. Yeah. And these kind of invisible illnesses, especially because it seems like he's having a mental health crisis, and so obviously it has to be my brain hurts. Yeah. It's kind of like, you know, if you're depressed, you obviously have a lot of the physical symptoms of someone who's quite ill, but I don't know. I guess it's so crazy that it's easier to admit that than just being like, he's severely depressed. Men would rather have Lyme disease than go to therapy once. There we go. Well, Andrew does manage to get it together enough to head back to law school for the start of the spring semester. But just because he's able to compartmentalize his pain doesn't mean he's actually gotten better. When he's

receives another $2 million from his family's trust, he quickly gambles it away. Andrew spends a summer pretending to be fine and interning at a white shoe law firm in New York before heading back for his final year of law school in the fall. The plan is that he'll graduate with his JD and then move to New York where his girlfriend, Kat, is working as a financial analyst. But then tragedy strikes. Kat's company is headquartered on the 93rd floor of the World Trade Center. She's working there on September 11th, 2001, and dies in the attack.

Her funeral is held on a windy, rainy morning at a church in the Hamptons. Andrew and Katz family, friends, and classmates arrive in expensive cars. As a service begins, the wind finally starts to calm down. And after a few minutes, the sun breaks through the clouds. It's a beautiful, peaceful moment for the mourners. But to Andrew, it barely registers. He's completely shell-shocked and heartbroken. Andrew does everything he can to help Kat's family through this difficult time.

When her younger sister has to go back to college a few weeks later, he's a person who drives her to Amherst and helps her get resettled. A few weeks later, he returns to Amherst to help celebrate Katz's sister's 20th birthday. He also spends a lot of time with Kat's mom, who encourages him to try therapy. but Andrew isn't interested. Instead, he takes another leave of absence from law school and moves into Kat's New York apartment

where he spends the next year grieving, drinking, and contemplating suicide surrounded by her furniture. In 2002, he's able to pull himself together enough to finish his law degree at NYU. And while he seems to be making progress again, it's still just a facade. Andrew's lawyers later estimate that he lost more than $4 million on stock market betting throughout law school.

Andrew has already learned how to hide his gambling problem from other people. Now, he's doing the same thing with his grief. And on the surface, it works. After graduation, Andrew ends up working at a place called Collar Capital, a very upscale financial institution that buys portfolios of private equity assets in the secondary market. Sachi, what do you think that means? These sorts of financial terms that kind of don't mean anything are lending to this overall impression that I think Andrew had,

which is like money's not real. Because when he gets in trouble with money personally, his dad bails him out. His day job is treating money as if it isn't real. He's doing it on the stock market. This just seems like someone who isn't connected to the reality of what money actually is for most people. Yes, I think it's numbers on a screen at most.

and by all accounts, Andrew is good at his job. But any money he earns goes right into more risky stock market bets. And even though he's a trust fund baby with a hefty salary, by 2006, he's broke enough that he has to start getting creative to fund his habit. That year, he takes out a $1 million loan against some real estate he owns and quickly loses it all. He gambles away $250,000 from an IRA too. which means that once again,

Andrew can't hide what he's doing from his parents. He writes them a letter explaining the situation, and once again, his dad gives Andrew the money he needs without suggesting an intervention. This is a family determined to enable this reckless child. Yes, and anyone who saw Andrew's balance sheets would quickly clock an out-of-control gambling addiction masquerading as stock market trading.

But his friends and colleagues see him as confident, capable, and successful. They're not alone. In 2007, Andrew starts dating a woman named Christina Frank. She's a pretty blonde who works for Anheuser-Busch. She also went to Princeton. Things might seem like they're looking up for Andrew, or at least holding steady. But tragedy isn't done with him yet.

And this time, when someone close to Andrew dies, the Casperson's private problems become all too public. It's the fall of 2009, and William D. Cohen is about a year into his role as a special correspondent for Vanity Fair. William is a handsome guy in his late 40s with a head of thick salt and pepper hair and piercing blue eyes. He went to a prestigious prep school, did his undergrad at Duke, and worked in finance for almost two decades. Now, he's an investigative journalist writing about the lives, crimes, and scandals of the moneyed elite. Lately, he's been super focused on a story about one of those elites, the economy-wrecking former president of Harvard, Larry Summers.

But then, William hears news that stops him in his tracks. Finn Casperson is dead in an apparent suicide. At first, the official story was that Finn took his own life. after being diagnosed with kidney cancer. His body was found with a note that said he was in pain and didn't want to be a burden to his family. But just two days after Finn's death, one of Finn's friends told a Florida newspaper

that he'd been having money troubles. Then the New York Times published a piece suggesting that Finn might have been engaged in some shady overseas tax sheltering and that his crimes were on the verge of being exposed. He could have been facing a 100,000, million dollar tax bill or even jail time. Finn's death is so unexpected and the circumstances around it are so strange. William decides he needs to learn more about what happened. I would not be

able to let this go if I heard this information as a reporter. This would drive me nuts. Yeah, especially because it's like so gossipy, you know. It's crazy. Intergenerational trauma and money. Come on. Yeah. Well, William starts his reporting by talking. talking to the people who knew Finn best, his neighbors and business partners. Before Finn died, he and his wife were living in Jupiter Beach, Florida, an extremely exclusive community that's been described as Old Wall Street in Shorts. And almost immediately, the story about Finn's cancer starts to seem questionable. Some of Finn's employees say they had no idea he was sick.

And one person tells William straight up that they don't think Finn had cancer. Then, William digs into the money and realizes Finn's image doesn't add up. Remember that deal that supposedly made him a billionaire? William learns that, in reality, Finn came out of the deal with just $150 million in cash. He was a flashy spender, but wasn't nearly as rich as everyone thought. Trying to exaggerate your wealth might be sketchy, but it's not a crime. But what William uncovers next makes him think that Finn might be. have been scared about his financial future. In the years before his death, Finn sold off a bunch

of his real estate. Most of those deals were above board, but one stands out to William. Finn sold the Jupiter Beach House to his wife for $100. In Florida, residencies can't be taken away from people during bankruptcy proceedings. William thinks Finn might have been trying to make sure that Andrew's mother, Barbara, had a place to live even if the family's assets. that's got seized. William pulls all of us together for a piece that runs in Vanity Fair in January of 2010 in just four months after Finn's death. It's titled, The Shot Herd Round the Clubs. The image-conscious Caspersons don't provide comment for the story. William doesn't know it, but he's tugging on a thread that will unravel into a much bigger scandal. Because

Barbara isn't the only member of the family who needs money. Andrew is still gambling his fortune away. And now that the bank of dad is closed, he's going to have to find a new way to finance his addiction. Hi, I'm Denise Chan, host of Scam Factory. You might remember hearing about our investigative series that exposed what's really happening behind those suspicious texts you get. Inside heavily guarded compounds across Asia, thousands are trapped and forced to scam others or risk torture. One of our most powerful stories was Jela's, a young woman who thought she'd found her dream job, only to end up imprisoned in a scam compound. Her escape story caught the attention

of criminals Phoebe Judge, and am honored to share more details of Jella's journey with their audience. But Jella's story is just one piece of this investigation. In Scam Factory, we reveal how a billion-dollar criminal empire turns job seekers into prisoners, and how the only way out is to scam your way out. Ready to uncover the full story? Binge all episodes of Scam Factory now. Listen to Scam Factory on the Wondery app or wherever you get your podcasts.

On Boxing Day 2018, 20-year-old Joy Morgan was last seen at her church, Israel United in Christ, or IUIC. I just went on my Snapchat and I just see her face plastered everywhere. This is the missing sister, the true story of a woman betrayed by those she trusted most.

IUC is my family and like the best family that I've ever had. But IUIC isn't like most churches. This is a devilish cult. You know when you get that feeling like I don't want to be here. I want to get out. It's like that feeling of like I want to go hang out. I'm Charlie Brink Coast Cuff and after years of investigating Joy's case, I need to know what really happened to Joy.

Binge all episodes of The Missing Sister exclusively an ad-free right now on Wondery Plus. Start your free trial of Wondery Plus on Spotify, Apple Podcasts, or in the Wondery app. I feel like a legend. Finn's death is incredibly hard on his family. His suicide is tragic, and the rumors that follow adds salt to him. the wound. Plus, they're all dealing with the fallout of Finn's financial problems. But Andrew is reeling from an even more personal betrayal. Shortly before his suicide, Finn confessed to Andrew that he had taken some money from his sons. We don't know the details of this theft,

but it does lend credence to the rumors about Finn's tax issues. And whatever went down, it was definitely heartbreaking for Andrew. He basically worshipped his father. Now, he has to deal with the knowledge that not only was Finn lying about his wealth, he also stole from his own family. Well, this is sort of what happens when your entire sense of self-worth as an individual or as a family is tied in your wealth. Yeah, I mean, of course. It's like what else do you think would happen? Yeah. Andrew deals with these revelations the way he's been dealing with everything for the last decade by numbing himself with alcohol and gambling. He's getting a ton of cash from various family assets and he's flushing it all away. Somehow, Andrew is able to keep up the ruse that everything

is fine. In 2011, about two years after Finn's death, he marries his girlfriend, Christina. But he insists that they file separate tax returns so she won't see how much money he loses on the stock market. That's a good move for Andrew, because he's about to lose a lot more money. Eight months after the wedding, in January 2012, Andrew leaves his job. job at Collar Capital. He tells his wife that he wants to do something more entrepreneurial. He holds up in a tiny office in Manhattan, where he makes one risky, compulsive stock purchase per day.

He spends the rest of his hours monitoring the market and staring anxiously at his account balances. Even if he decides to go out for lunch or a walk, he'll bring his iPad with him so that he doesn't miss any changes in the market. He hates being away from the action even more. more than he hates losing money. And he is losing money. By the time summer rolls around, Andrew is broke.

For his usual backup plan, he decides to see if his family can cover his losses. But this time, he doesn't come clean and admit what he's done. Instead, Andrew decides to follow in his dad's footsteps and steal from his own family. He goes to one of his brothers and his mom and asks them for money that he claims he's going to invest in private equity. Together, they give him about $2 million.

They're happy to do it. Sachi, can you read how an acquaintance later puts it to the Wall Street Journal? Yeah, they said, imagine if your brother or your best friend approached asking for a relatively small investment into something he did every day. This makes sense. I would probably give somebody that money if I thought they knew what they were talking about,

but there are people in his family like his mom who know how many times they've had to pay to get him out of a jam, or how many times he's lost their money? I can't believe she's doing this again. Yes, and of course, Andrew takes his family's money and invests it the same way he always does into his gambling slash trading accounts.

At this point, he's developed a favorite tactic, betting against the S&P 500. Basically, he's constantly wagering everything he has on the hope that the whole stock market will decline in value. A professional options trader later describes Andrew's strategy for investing as, quote, a recipe for inevitably losing everything.

But the thing about gambling is that sometimes you do get lucky. When Andrew first invests his family's money, he hits the jackpot. Suddenly, he has $4 million, double the amount they gave him. But he can't bring himself to pull the money out of the market and repay them. So before long, he's back to square one. At this point, Andrew has gambled away a total of approximately $19 million over the last 13 years. His family asks what happened, and Andrew tries to claim that the brokerage firm he was using just lost their money. But they don't buy it.

So finally, Andrew admits that he gambled away millions of dollars of his family's money again. Apparently, the third time's a charm, his family finally encourages him to see. seek professional help. By now, the stakes are higher. Andrew's wife is now pregnant with their first child, which means it's time for the 36-year-old man to grow up and get it together. In November of 2012, Andrew finally begins seeing a psychiatrist. Thank God. At 36, he decides to take his mental health seriously at his big age when he is pregnant and married. Yes, and in therapy, he says all of the right things. He agrees to take the antidepressants

and gets another job in finance so he won't be left to his own devices all day. Andrew's efforts pay off. In March of 2013, after just a few months, his psychiatrist declares that his gambling addiction is in remission. Now, you might think that a few months

isn't nearly enough time to deal with a problem as deep and obsessive as Andrews, and you'd be right, because actually nothing has changed. changed. He's been playing the stock market the whole time. He stopped seeing the psychiatrist after just seven sessions. When the doctor says they can't refill his antidepressant prescription unless he comes in for an appointment, Andrew decides that he doesn't need to take his meds either. Sounds about right. This always works. This is a great plan. Yeah, I think the second you start feeling

better, you should stop taking your meds. Yes, you should definitely listen to that part of your brain. Well, things look grim. April of 2013, he stops gambling because he runs out of money again. A month later, his wife gives birth to their first child. At the end of the year, he gets a bonus of nearly half a million dollars, and he immediately starts gambling again. His family may want him to seek help, but Andrew can't internalize that he has a problem. And now that he's learned how easy it is to get rich people in his orbit to hand over money, he's not going to be able to make himself stop.

By November of 2014, Andrew is as broke as he's ever been. He's set to get a $4 million bonus at the end of the year in just three weeks. But that's too long. He needs to be able to gamble more immediately. This is when he develops the scheme we heard about earlier, where he goes to his friends and family

and offers them a supposed investment opportunity with a way too good to be true 15% interest rate. At first, Andrew gets a couple of million dollars from a friend. This is chump change for the circles Andrew runs in, and it's wild that Andrews victims don't see that interest rate as a red flag, but they have no idea about his years-long addiction issues. Even his wife doesn't notice a warning signs, and Andrew uses his experience in finance to make sure that his offer includes tons of official-looking paperwork written out an almost correct legalese. But really, people just trust him.

Andrew's social capital, his education, and his name are all enough to get people on board. As a colleague will later tell Vanity Fair, there's this feeling that Andrew, quote, didn't go to Groton and Princeton and Harvard Law by being either a dope or a bad guy. Several people go to those schools expressly because of those two qualities. I know. Like, some people only get into those schools because they are dumb and bad. Yes, it seems like a breeding ground.

Mm-hmm. Andrew's friends and family invest some $11 million with him over the course of a year. All of it goes straight into Andrew's personal accounts. And his investment strategies are only getting more erratic. Sometimes a number will occur to him in the shower

and he'll write it in the steam on the door so he can remember it and use it in his trading later that day. You will probably not be surprised to hear that around this time, he often stops for a drink on his way to work and dips out of the office for another one midday. But somehow, according to the people around him, he's still holding it together in public. Multiple friends and colleagues will later testify that they only ever thought of Andrew as a dedicated co-worker, a trusted mentor, and a beloved friend. By 2015, his wife has noticed that he's drinking more, but they've

just had a second kid, so she writes it off as him dealing with the stress. But behind the scenes, Andrew's losses are mounting, and his need for cash is basically a black hole. So Andrew starts telling his clients to send their fees to a new bank account, which is just his personal account. He manages to net about $9 million this way, but Andrew's bosses aren't as loose with their balance sheets as his friends. They notice pretty quickly and start asking questions. Luckily, Andrew knows what to do. He just has to find new investors in his scheme so that he can pay the money back.

He might be doing complicated financial transactions at his day job, but at this point, his side hustle is a good old-fashioned Ponzi scheme. If you're playing scamplencers bingo at home, I do believe a reference point to the Ponzi scheme now means that you have probably filled your card. Congratulations, you win nothing. Yeah, it's also funny because, Because you know these people never think they're doing Ponzi schemes.

They're just kind of like, well, if I just use this money from someone else to pay someone else, to pay someone else. No, that's like the definition of a Ponzi scheme. Yeah, exactly. But, you know, it's his friends. This time, Andrew brings his investment opportunity directly to financial institutions, which can shell out more money on shorter notice than individuals. But with more money comes more questions about how exactly this whole thing is supposed to work. The first two firms he tries ask him for more details,

but he can't answer their questions so they turn him down. That's where James McIntyre and the more charitable foundations $25 million comes into play. Andrew has stolen from his own company and gotten away with it. But now he's tangling with a different institution and working with way more money. He's not just setting himself up for disaster, he's racing towards it at full speed.

It's early January 2016 in just a couple of months after Andrew's successful pitch meeting with James. Right now, he's riding an intense high. The market shifted his way and his trading account is worth more than $70 million. Now, Sachi, they say money can't solve your problems,

but in this case, they are wrong. Andrew could repay the $25 million from James and his foundation, plus the $11 million he took from friends and family. He could recoup the $20 million of his own money he's lost since starting law school, and after all that, Andrew would still come out $14 million ahead. If he could just get himself to cash out now, he could stop constantly panicking. He could probably set up trusts for his kids and give them the stable, generational wealth he grew up with. But that is not how addiction works.

Instead of getting out clean, Andrew spends the next few weeks on a financial roller coaster. He briefly ends up completely broke, then somehow finds himself with even more money in his trading account, almost $75 million. By the way, this is all still January. In February, he gets even richer with over $100 million in his account at one point. Here's Andrew describing what happens next on an episode of the podcast Beyond the Balance Sheet. Tuesday morning after a long weekend,

rolled around, and at 9.30 approached. I got a little more nervous, a little more nervous. And finally, right as the market opened, you know, I called my broker, and I told him to place the entire cash balance on a single option spent. By March, his account is worth only $1.2 million. That's a lot of money to most of us,

But for Andrew, it's devastating. Yeah, losing millions of dollars over and over again and only ending up with a embarrassing fraction of what you had, that would be devastating. Yes. So Andrew goes back to one of the firms that rejected him last year. And rather than making a more cautious, targeted pitch, he decides to literally go double or nothing

and ask for twice as much money as he did the first time. but he still can't answer any of their questions and he gets rejected again. And even Andrew can't ask his family for the amounts of money he needs at this point. So he decides to go back to someone who can. It's March 2016, about four months after James first invested with Andrew.

And today, Andrew is calling to tell James he has a problem. A large investor in his fund has pulled their money. And he's hoping that James and his foundation can send over another $20 million to make up the difference. James likes Andrew, but this is a lot of money. He wants to do his due diligence. So when Andrew sends over a pile of paperwork outlining the terms of the deal, James wants to talk to the guy who's vouching for the collateral on the loan.

Basically, that's a person who's guaranteeing that James and his firm won't lose their shirts in this deal. His name is John Nelson, and according to the documents, he works at Andrew. his old company, Caller Capital. Soon enough, James gets an email from Andrew with John C-C'd setting up a conference call. Before the call, James gets a heads-up from someone else at his firm. The email address for John Nelson had only been created 20 minutes after James asked to set up the call.

On top of that, the email domain wasn't actually the one used by caller. So, of course, James is pretty suspicious by the time the call rolls around. James gets on the phone with someone who says he's John Nelson, but when James asks for his phone number, John says he can't share it. But after the call ends, John emails James his phone number. James confronts Andrew about John, and Andrew says he'll look into it. And when Andrew calls back, he gets really weird. He says that John Nelson was apparently invented by another analyst at caller,

and that that guy is in a lot of trouble. Andrew goes out of his way to tell James that his investment is totally safe, but he can't say more, unfortunately, because of pending legal matters. This is such a sloppy, bad lie. It doesn't even make any sense. I know, it's like weird Mrs. Doubtfire shit. You're like, what, who's what, what's who? Like, stop.

Needlessly complicated, fake names, like, secret, I can't tell you because of legal matters. Come on. I know. And James has seen enough. He doesn't know exactly what's happening. year, but he knows he does not want to be involved anymore. He tells Andrew that not only will his firm not be investing any more money, they want their original $25 million back. James's firm also gets in touch with Andrew's current employer to make sure they know that something is up.

So far, Andrew has gotten away with his schemes by taking money from people who wanted to protect his reputation more than they wanted to call him on his bullshit. But more capital and his current don't care about the Casperson family name, and the luck and privilege that have always allowed him to skate by is about to run out. A few weeks after James asks for his money back, Andrew, his wife, and their children fly to Florida to see his mom. It should be a nice family trip, but Andrew is distracted.

After more than a decade of gambling and tens of millions of dollars in losses, he's finally run out of money for real. He doesn't have any cash to gamble with and he can't pay back the money he owes James' firm. When they're in Florida, Andrew sends his last million dollars to his wife. He writes a will, leaving everything to her. Then, on the plane ride home,

he composes a suicide note apologizing for his crimes and asking his creditors to leave her alone. As a plane bumps down onto the tarmac, Andrew's stomach twists in dread. he helps unbuckle his kids and shepherds them off the plane alongside his wife. But when they walk out into the terminal,

there are men in uniform, federal agents calling Andrew's name. They arrest him for securities and wire fraud. Weirdly, Andrew is kind of relieved. His worst fears have come true. Now, there's nothing for him to do but find out what it feels like to actually pay his debts.

In November 1974, 1974, IRA bombs ripped through two Birmingham pubs killing 21 innocent people. Hundreds more were injured. It was the worst attack on British soil since the Second World War. When a crime this appalling and shocking happens, you want the police to act quickly. And boy, did they. The very next day, they had six men in custody. Confessions followed, and the men were sent down for life. Good riddance, you might think, except those men were innocent.

Join me, Matt Ford. And me, Alice Levine. For the latest series of British scandal, all about the Birmingham Six. It's the story of how a terrible tragedy morphed into a travesty of justice, and how one man couldn't rest until he'd exposed the truth. Follow British Scandal now, wherever you listen to podcasts and binge entire series early and ad-free on Wondery Plus. It's your man, Nick Cannon, and I'm here to bring you my new podcast, Nick Cannon at night.

I've heard y'all been needing some advice in the love department. So who better to help than yours truly? Now, I'm serious. Every week, I'm bringing out some of my celebrity friends and the best experts in the business to answer your most intimate relationship questions. Having problems with your man, we got you. Catching feelings for your sneaky link? Let's make sure it's the real.

Deal first. Ready to bring toys into the bedroom? Let's talk about it. Consider this a non-judgment zone to ask your questions when it comes to sex and modern dating in relationships, friendships, situationships, and everything in between. It's going to be sexy, freaky, messy, and you know what, you'll just have to watch this show. So don't be shy.

Join the conversation and head over to YouTube to watch Nick Cannon at night or subscribe on the Wondry app or wherever you get your podcast. Want to watch episodes early and ad-free? Join Wonderry Plus right now. Now, I feel like a legend. In some ways, getting arrested is the best thing that could have happened to Andrew. Of course, he gets bailed out of jail almost immediately, but instead of going home, he checks himself into the psychiatric ward of a New York hospital.

He says he's a risk to himself, which is definitely true. While he's in the hospital, Andrew gets a visitor. It's his priest offering to give him confession. Andrew goes to church regularly, so he knows the priest well. And when he starts spilling all of his secrets for the first time, he feels like a weight has lifted. Hey, I don't want to put too fine a point on this, but that's therapy. No, it's different.

I know there's a priest involved here, but generally what this is is basically therapy. It's talk therapy. Okay, okay. Well, he spends the next few months focusing on his recovery. He joins Alcoholics Anonymous and Gambler's Anonymous, and he hires a lawyer to help prepare him for his day in court. And William has been following this scandal closely.

In the summer of 2016, William publishes a huge piece about Andrew and Finn in Vanity Fair, calling them the Dukes of Deception. Andrew didn't do a good job of hiding his tracks, and the government has plenty of evidence. evidence. So in July, four months after his arrest, Andrew pleads guilty to one count each of securities fraud and wire fraud. That means he and his lawyer can focus on the real issue, his punishment. Before his sentencing, Andrew and his lawyer put together a 175-page submission

explaining his history with addictive behavior. It includes testimony from his friends, family members, colleagues, and even the priest. the same points came up over and over, the tragedy of Finn and Kat's deaths. One of his victims writes that, quote, The man who committed these crimes is not the Andrew Casperson I know and respect. We have long talks about the traumas in his life, and he is just now beginning to understand the impact these events have had on him.

Sachi, Andrew is 40 years old, and all of the letter writers seem to forget that Andrew lost his first million when Katzsche's. and Finn were both still alive. Their deaths exacerbated the gambling addiction he was already developing. Yeah, this is collective amnesia. He was doing crime and gambling

and really engaged in his addiction before, you know, some of these key traumas happen. I'm sure he had other traumas, but that doesn't mean you get to do this. Exactly. And maybe the most interesting read on the situation comes from Andrew's mother. In her letter, she says that she and Andrew

have talked a lot about why he did he did. She theorizes that because Andrew was so brilliant and talented as a child, he never had to ask for help, and so he never learned how. Andrew's community clearly likes him and cares about him, but they won't hold him or themselves accountable for his mistakes. But it works on their intended audience, the judge. He's so moved that he publicly agonizes about handing down his sentence. Sure, the sentencing guidelines suggest that Andrew should get 15 years in prison, but the judge thinks this is outrageous, especially given the fact that Andrew was an addict.

Instead, he sentences Andrew to four years in federal prison, followed by three years of supervised release. He also orders Andrew to pay back his victims. In a twisted scam-fluencer's tie-in, Shohei Otani interpreter Ipe Mizuhara's attorney cited Andrew's case as an example for why compulsive gambling should be a mitigating factor in sentencing. Andrew has promised everyone, including a federal judge, that he's a changed man. Now he actually has to be that man and take responsibility for what he's done. Andrew reports to prison in early 2017. It's a minimum security camp that sits next to a medium

security facility. The camp includes a gym, baseball fields, and even botchy courts. But it's still a far cry from the life he's used to. Throughout his sentence, Andrew seems to be committed to his recovery. He later says that he motivated himself for his job as a janitor, making as much as $5 per month by thinking of it as a service he's providing his clients. Later, he works as a GED instructor helping fellow inmates get their diplomas. The prison doesn't have formal AA or GA programs, so he and some of the other inmates create one for themselves. After two and a half years, Andrew is released in the summer of 2019.

Two years later, Christina files for divorce. Andrew has mostly laid low since then, working in some capacity with financial technology and HR firms. In 2024, he agrees, to appear on a couple of podcasts to discuss what he did. He says that he's been keeping his head down to avoid upsetting any of his victims and remains focused on recovery from his addictions.

Around the same time, Andrew launches a new company. It's called Lazarus Freelancing, and it promises to, quote, perform outsourced project-based work for a range of forward-thinking companies. At the bottom of the website, there's a dedication making a promise to any future Lazarus client.

all work performed by Andrew Casperson. Sachi, I feel like, you know, as much as this was a classic Ponzi scheme, and of course, you know, this guy had addiction issues, no denying that. It is just so upsetting to see how, once again, the other half lives. Yeah, this one does not feel good. This is really someone who just had every possible opportunity afforded to him. He squandered all of them. He lost millions of dollars.

He ripped people off. He took money away from his family, like bad from the beginning. Yeah, and you know, no one really cared enough to stop him. And I understand that's kind of its own really sad thing. But show me the universe where anyone with lesser means and less privilege who has an addiction and commits crimes gets any sympathy at all. Yeah, and I actually really resent the use of. addiction and recovery in his like redemptive plot there's a lot of people who have addiction

problems and handle them differently and also those people often have even fewer resources you know he could afford whatever treatment would have helped him like this is not somebody who didn't have the ability to get better and then to use addiction which is so big and so heavy and so hard for so many people to still use it as a cudgel for like like getting other people on your side? Gross. Yes. And it's like, well, I was born rich and my family's rich.

Therefore, I must be as rich as possible forever because it's owed to me. It's weird. It's like it's only for rich people that like their comfort has to be continued on. And if it doesn't, it's such a tragedy. Whereas, you know, everyone else in the real world is constantly fluctuating. Yeah. And, you know, nothing is guaranteed. And we have to bootstrap and blah, blah, blah, blah.

And it's just kind of like, oh, so that's when it's important. I mean, this is a family and a father who certainly thought that like making money was the most important thing. And so, of course, the thing that makes this guy feel compulsive and that takes away his own agency and his own control is linked to the ability to make a lot of money at once. So I get that they want to say like, oh, this happened because his dad died or this, you know, this awful thing happened to his girlfriend or whatever else. That's part of it. but he was also raised in an environment that told him, this is how you be a man. That's part of affluenza.

I mean, is thinking that you just are entitled to everything because that's how you've been raised, including this particular kind of pain. I know, and it's almost like, I think for a lot of these scams where it's like rich people scamming their rich friends, these people testified about his character. It all goes back to the image thing.

It looks good on them to not have been fooled by someone who was using them. There's, like, so much solidarity between rich people. Yeah, I think rich people don't want to tell the rest of us that they're actually kind of dumb. They're dumb and they're all in cahoots

to the point where they're willing to trust someone that is a good old Princeton boy or whatever with millions and millions of dollars knowing what just happened to his dad. I feel like that big part of the lesson today is, like, you shouldn't trust somebody just because they said they went to a nice school.

That is a very American affliction. Do not get me started school. Who cares? I do not give a shit where someone went to school. You're 48 years old. You're telling me where you went to college. Oh my God, congrats. Shut up.

Who the hell cares? Sarah, the thing about really, really rich white men in these particular positions of power is that I kind of always view them as like in flop sweat and squirly and disheveled. I don't think it would register to me if one of them was acting kind of. weird. No, I don't think it would either because I don't know what's considered normal.

You know, anything weird I see why people do or behave, I'm kind of like, maybe that's the cultural thing. That's their culture. That's their business. And it's not for us to know. In my mind, I'm like, surely I just, there's something culturally I don't understand. Therefore, I don't know the signs of distress. We need to do more research. Yeah. Okay. Something for later. Scamfulencers, get exclusive episodes and early access to new ones all ad-free on Wondry Plus. Join now in the Wendry app, Apple Podcasts, or Spotify. Before you go, help us out by taking a quick survey at Wendry.com slash survey. This is Andrew Casperson, Rich People Problems.

I'm Sarah Hagee, and I'm Sachi Cole. If you have a tip for us on a story that you think we should cover, please email us at scampfulencers at Wendry.com. We use many sources in our research. search. A few that were particularly helpful were Casperson tried to raise up to 50 million from KKR by Rob Copeland and Serena Ing for the Wall Street Journal,

Andrew's interviews with the Beyond the Balance Sheet and Unintended Consequences Podcasts and William D. Cohen's reporting in Vanity Fair. Zan Romanov wrote this episode, additional writing by us, Satu Cole and Sarah Hagee. Eric Thurm is our story editor. Fact-checking by Gabrielle Jolet.

Sound design by James Morgan. Additional audio assistance provided by Augustine Lim. Our music supervisor is Scott Velasquez for Frieson Sink. Our managing producer is Desi Blaylock. Janine Cornelow and Stephanie Jens are our development producers. Our associate producer is Charlotte Miller. Our senior producers are Sarah Eni and Jenny Bloom.

Our executive producers are Jenny Lauer Beckman, Marshall Louie, and Aaron O'Flaherty for Wondery. Thank you.