Andrew Caspersen: Rich People Problems | 178

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/wonderynewsletter Listen 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.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Scaachi Koul?

  Audible subscribers can listen to all our episodes of Scamfluencers ad-free right now. Join Audible today by downloading the Audible app.

• 0:08Sarah Hagi?

  A note for our listeners: This episode contains references to suicide. Please listen with care.

• 0:20Sarah Hagi?

  Sachi, we always talk about how we'd 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?

• 0:32Scaachi Koul?

  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.

• 0:42Sarah Hagi?

  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.

• 0:50Scaachi Koul?

  It's a beautiful incantation to say every night to yourself, Sarah.

• 0:53Sarah Hagi?

  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.

• 1:14Sarah Hagi?

  It's November 2015, and Andrew Casperson 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?

• 1:33Scaachi Koul?

  Yeah, this is the whitest man to ever white. He looks like a potato with eyes, nose, and mouth carved in.

• 1:40Sarah Hagi?

  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 is targeting. Andrew explains that he's offering the foundation a completely secure investment opportunity

• 2:25Sarah Hagi?

  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 scamflinter setup. 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 so-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

• 3:08Sarah Hagi?

  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's 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.

• 3:52Sarah Hagi?

  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.

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• 4:25Speaker 03

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• 4:59Sarah Hagi?

  From Wondery, I'm Sarah Haggie.

• 5:01Scaachi Koul?

  And I'm Sachi Cole.

• 5:02Sarah Hagi?

  And this is Scamfluencers.

• 5:13Sarah Hagi?

  Andrew Casperson was raised in a family that valued money and appearances above all else. So when Andrew develops a gambling problem in his twenties, 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.

• 5:51Sarah Hagi?

  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, Olaf. Olaf emigrates from Norway to the US 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 3/4 of a million dollars today. His company is ahead of its time. It basically invents the subprime mortgage in the 60s.

• 6:28Scaachi Koul?

  Well, we should thank him. Everybody loves the subprime mortgage. Definitely worked out. No problems there.

• 6:34Sarah Hagi?

  Yeah, I mean... Listen, you should just lie about that being in your family history.

• 6:38Scaachi Koul?

  Yeah, I wouldn't brag about that.

• 6:40Sarah Hagi?

  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

• 7:25Sarah Hagi?

  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."

• 8:04Scaachi Koul?

  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 weener. That would be less undignified.

• 8:15Sarah Hagi?

  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.

• 8:31Sarah Hagi?

  Andrew is the youngest of Finn's four children. As a teenager, he rows 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 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 is pretty strict, so he never really drank. But college is another story. At Princeton, he starts drinking heavily and regularly.

• 9:14Sarah Hagi?

  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

• 10:00Sarah Hagi?

  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."

• 10:25Speaker 04

  No longer actually had to do the things in my life to make sure I could actually get 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 descent.

• 10:42Scaachi Koul?

  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 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?

• 11:13Sarah Hagi?

  Yeah, that's exactly it. It's kind of like, we already see this other world he's a part of.

• 11:17Scaachi Koul?

  Yeah.

• 11:18Sarah Hagi?

  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.

• 11:35Sarah Hagi?

  Getting cut from the team doesn't affect Andrew's game. He starts dating a classmate named Catherine McCray, who goes by Kat. 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 get 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.

• 12:20Sarah Hagi?

  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.

• 12:38Scaachi Koul?

  This is loser behavior. What's wrong with you?

• 12:40Sarah Hagi?

  Well, you are forgetting that this is 1999. All tech stocks are high-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.

• 13:07Sarah Hagi?

  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

• 13:52Sarah Hagi?

  is just a drop in the bucket. And his family's WASP-y 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."

• 14:10Scaachi Koul?

  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.

• 14:20Sarah Hagi?

  Yeah.

• 14:21Scaachi Koul?

  That was a good show, but not if it's actually happening.

• 14:25Sarah Hagi?

  Yeah, it seems like something that is based on real life.

• 14:29Scaachi Koul?

  Mm-hmm.

• 14:30Sarah Hagi?

  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,

• 15:14Sarah Hagi?

  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.

• 15:46Scaachi Koul?

  Maybe he has these issues, whatever. But I will say that Lyme, in particular, is maybe second only to cancer in the scanfluencer's illness canon. These people are always getting Lyme in the same way that they're always getting cancer.

• 16:00Sarah Hagi?

  Yeah.

• 16:00Scaachi Koul?

  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.

• 16:08Sarah Hagi?

  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.

• 16:22Scaachi Koul?

  Men would rather have Lyme disease than go to therapy once.

• 16:24Sarah Hagi?

  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 receives another $2 million from his family's trust, he quickly gambles it away. Andrew spends the 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.

• 17:09Sarah Hagi?

  She's working there on September 11, 2001, and dies in the attack.

• 17:15Sarah Hagi?

  Her funeral is held on a windy rainy morning at a church in the Hamptons. Andrew and Kat's family, friends, and classmates arrive in expensive cars. As the 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.

• 17:44Sarah Hagi?

  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 the person who drives her to Amherst and helps her get resettled. A few weeks later, he returns to Amherst to help celebrate Kat'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.

• 18:25Sarah Hagi?

  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 Caller Capital, a very upscale financial institution that buys portfolios of private equity assets in the secondary market. Sachi, what do you think that means?

• 19:08Scaachi Koul?

  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.

• 19:33Sarah Hagi?

  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.

• 20:15Sarah Hagi?

  And once again, his dad gives Andrew the money he needs without suggesting an intervention.

• 20:22Scaachi Koul?

  This is a family determined to enable this reckless child.

• 20:28Sarah Hagi?

  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.

• 21:10Sarah Hagi?

  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.

• 21:50Sarah Hagi?

  But then, William hears news that stops him in his tracks. Finn Casperson is dead in an apparent suicide.

• 21:59Sarah Hagi?

  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 million tax bill or even jail time. Finn's death is so unexpected and the circumstances around it are so strange.

• 22:42Sarah Hagi?

  William decides he needs to learn more about what happened.

• 22:46Scaachi Koul?

  I would not be able to let this go if I heard this information as a reporter. This would drive me nuts.

• 22:51Sarah Hagi?

  Yeah, especially because it's like so gossipy, you know?

• 22:55Scaachi Koul?

  It's crazy. Intergenerational trauma and money? Come on.

• 22:59Sarah Hagi?

  Yeah. Well, William starts his reporting by 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?

• 23:42Sarah Hagi?

  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 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.

• 24:25Sarah Hagi?

  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 got seized. William pulls all of this together for a piece that runs in Vanity Fair in January of 2010, just four months after Finn's death. It's titled "The Shot Heard Round the Clubs." The image-conscious cast persons 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.

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• 26:16Sarah Hagi?

  Finn's death is incredibly hard on his family. His suicide is tragic, and the rumors that follow add salt to 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,

• 27:01Sarah Hagi?

  he also stole from his own family.

• 27:05Scaachi Koul?

  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.

• 27:13Sarah Hagi?

  Yeah, I mean, of course. It's like, what else do you think would happen?

• 27:16Scaachi Koul?

  Yeah.

• 27:17Sarah Hagi?

  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.

• 27:54Sarah Hagi?

  Eight months after the wedding, in January 2012, Andrew leaves his job at Caller Capital. He tells his wife that he wants to do something more entrepreneurial. He holes 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 than he hates losing money. And he is losing money. By the time summer rolls around, Andrew is broke. For his usual backup plan,

• 28:39Sarah Hagi?

  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,

• 29:23Sarah Hagi?

  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/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.

• 30:08Sarah Hagi?

  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.

• 30:52Sarah Hagi?

  His family finally encourages him to 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.

• 31:36Sarah Hagi?

  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 Andrew's, and you'd be right. Because actually, nothing has changed. He's been playing the stock market the whole time. He stops 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.

• 32:18Sarah Hagi?

  Yes, you should definitely listen to that part of your brain. Well, things look grim. By 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.

• 32:58Sarah Hagi?

  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 Andrew's victims don't see that interest rate as a red flag. But they have no idea about his years-long addiction issues.

• 33:42Sarah Hagi?

  Even his wife doesn't notice the warning signs. And Andrew uses his experience in finance to make sure that his offer includes tons of official-looking paperwork, written out in 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.'"

• 34:17Scaachi Koul?

  Several people go to those schools expressly because of those two qualities.

• 34:21Sarah Hagi?

  I know.

• 34:22Scaachi Koul?

  Like, some people only get into those schools because they are dumb and bad.

• 34:26Sarah Hagi?

  Yes. It seems like a breeding ground.

• 34:28Scaachi Koul?

  Mm-hmm.

• 34:29Sarah Hagi?

  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 coworker,

• 35:13Sarah Hagi?

  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.

• 35:58Sarah Hagi?

  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.

• 36:09Scaachi Koul?

  If you're playing Scamfluencer's 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.

• 36:19Sarah Hagi?

  Yeah, it's also funny 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."

• 36:28Scaachi Koul?

  No, that's like the definition of a Ponzi scheme.

• 36:30Sarah Hagi?

  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 Moore Charitable Foundation's $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.

• 37:15Sarah Hagi?

  He's not just setting himself up for disaster, he's racing towards it at full speed.

• 37:23Sarah Hagi?

  It's early January 2016, 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.

• 38:08Sarah Hagi?

  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.

• 38:49Speaker 06

  Tuesday morning after a long weekend, rolled around, and as 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 options bet.

• 39:05Sarah Hagi?

  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.

• 39:17Scaachi Koul?

  Yeah, losing millions of dollars over and over again, and only ending up with an embarrassing fraction of what you had, that would be devastating.

• 39:27Sarah Hagi?

  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

• 40:11Sarah Hagi?

  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's old company, Caller Capital. Soon enough, James gets an email from Andrew with John CC'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

• 40:56Sarah Hagi?

  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.

• 41:40Sarah Hagi?

  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.

• 41:49Scaachi Koul?

  This is such a sloppy, bad lie. It doesn't even make any sense.

• 41:54Sarah Hagi?

  I know. It's like weird Mrs. Doubtfire shit. You're like, what? Who's what? What's who? Like, stop.

• 41:59Scaachi Koul?

  Needlessly complicated, fake names, like, secret, I can't tell you because of legal matters? Come on.

• 42:05Sarah Hagi?

  I know. And James has seen enough. He doesn't know exactly what's happening here, 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 employer 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.

• 42:51Sarah Hagi?

  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's firm. When they're in Florida, Andrew sends his last $1 million 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,

• 43:36Sarah Hagi?

  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.

• 44:10Speaker 07

  A dark night, a quiet house. But inside, danger was lurking.

• 44:14Speaker 08

  Oh, not really. We have Xfinity Shield, so we're not worried. What if protecting your home and devices could be drama-free? Xfinity. Imagine that. Restrictions apply. Not available in all areas.

• 44:25Speaker 09

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• 45:04Sarah Hagi?

  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.

• 45:39Scaachi Koul?

  Hey, I don't want to put too fine a point on this, but that's therapy.

• 45:42Sarah Hagi?

  No, it's different.

• 45:46Scaachi Koul?

  I know there's a priest involved here, but generally, what this is, is basically therapy. It's talk therapy.

• 45:51Sarah Hagi?

  Okay, okay. Well, he spends the next few months focusing on his recovery. He joins Alcoholics Anonymous and Gamblers 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. So in July, four months after his arrest, Andrew pleads guilty to one count each of securities fraud and wire fraud.

• 46:31Sarah Hagi?

  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."

• 47:14Sarah Hagi?

  Sachi, Andrew is 40 years old, and all of the letter writers seem to forget that Andrew lost his first million when Kat and Finn were both still alive. Their deaths exacerbated the gambling addiction he was already developing.

• 47:28Scaachi Koul?

  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 happened. I'm sure he had other traumas, but that doesn't mean you get to do this.

• 47:41Sarah Hagi?

  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 what 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,

• 48:26Sarah Hagi?

  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 scamfluencer's tie-in, Shohei Ohtani 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.

• 49:07Sarah Hagi?

  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 bocce 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.

• 49:54Sarah Hagi?

  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,

• 50:38Sarah Hagi?

  there's a dedication making a promise to any future Lazarus clients. "All work performed by Andrew Casperson."

• 50:48Sarah Hagi?

  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.

• 51:05Scaachi Koul?

  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.

• 51:22Sarah Hagi?

  Yeah, and you know, no one really cared enough to stop him. And I understand that's kind of its own really sad thing, like. 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.

• 51:38Scaachi Koul?

  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 getting other people on your side? Gross.

• 52:14Sarah Hagi?

  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.

• 52:35Scaachi Koul?

  Yeah.

• 52:35Sarah Hagi?

  And, you know, nothing is guaranteed and we have to bootstrap and blah, blah, blah, blah, blah. And it's just kind of like, oh, so that's when it's important.

• 52:44Scaachi Koul?

  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.

• 53:24Sarah Hagi?

  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 and 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.

• 53:45Scaachi Koul?

  Yeah, I think rich people don't want to tell the rest of us that they're actually kind of dumb.

• 53:50Sarah Hagi?

  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.

• 54:03Scaachi Koul?

  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 squirrely and disheveled. I don't think it would register to me if one of them was acting kind of weird.

• 54:41Sarah Hagi?

  No, I don't think it would either because I don't know what's considered normal. You know, anything weird I see white people do or behave, I'm kind of like, maybe that's a cultural thing.

• 54:50Scaachi Koul?

  That's their culture, that's their business. And it's not for us to know.

• 54:53Sarah Hagi?

  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.

• 54:59Scaachi Koul?

  Hmm, we need to do more research.

• 55:01Sarah Hagi?

  Yeah.

• 55:01Scaachi Koul?

  Okay, something for later.

• 55:09Scaachi Koul?

  Follow Scamfluencers on the Audible app or wherever you get your podcasts. You can listen to all episodes of Scamfluencers ad-free by joining Audible.

• 55:18Sarah Hagi?

  This is Andrew Caspersen, Rich People Problems. I'm Sarah Hagee.

• 55:23Scaachi Koul?

  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 [email protected]. We use many sources in our research. A few that were particularly helpful were Caspersen 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.

• 55:48Sarah Hagi?

  Zan Romanoff wrote this episode. Additional writing by us, Sachi Cole and Sarah Hagee. Eric Thurm is our story editor. Fact checking by Gabrielle Jollet. Sound design by James Morgan. Additional audio assistance provided by Augustine Lim. Our music supervisor is Scott Velazquez for Frieson Sync. Our managing producer is Desi Blaylock. Janine Cornolo and Stephanie Jens are our development producers. Our associate producer is Charlotte Miller. Our senior producers are Sarah Enne and Ginny Bloom. Our executive producers are Jenny Lauer Beckman, Marshall Louie, and Erin O'Flaherty from Wondery.

• 56:34Speaker 10

  Journalist Tristan Redman goes where no son-in-law should ever go. Deep into his wife's family history, digging up the cold case of who murdered her great-grandmother. Because, I should mention, he thinks the murderer might actually be the beloved family patriarch. For the best binge-watch series like Ghost Story, listen to the Audible True Crime Podcast wherever you get your podcasts.