Dana Giacchetto - Swindler to the Stars | 208

Summary

Scamfluencers: Dana Giacchetto – Swindler to the Stars | 208

Podcast: Scamfluencers by Audible
Episode Title: Dana Giacchetto - Swindler to the Stars
Hosts: Scaachi Koul & Sarah Hagi
Release Date: April 6, 2026

---

Episode Overview

This episode explores the meteoric rise and catastrophic fall of Dana Giacchetto, the so-called "Stockbroker to the Stars" of the 1990s and early 2000s. Through interviews, pop culture references, and deeply researched anecdotes, hosts Scaachi Koul and Sarah Hagi unpack how Giacchetto used his hustle, charisma, and hunger for celebrity proximity to infiltrate the worlds of Hollywood, art, and music—only to spiral into fraud, addiction, and disgrace. The story is both cautionary and tragic, delving into celebrity culture, moneyed circles, and the intoxicating power of being “in the scene,” as well as the human cost of unchecked ambition.

---

Key Discussion Points & Insights

1. The Lure of Celebrity and the Rise of Dana (00:00–15:51)

• Fascination with Celebrity: Dana’s primary addiction was the “scene” rather than money. He craved proximity to fame, often at the expense of his own ethics.
  • “A lot of the scammers we talk about don’t come into it because of need. They just want to be seen by somebody with name recognition. It’s really sad.” — Sachi Cole (00:33)
• Early Life & Personality: Dana grew up as a golden child in a middle-class Boston suburb, with little understanding of consequences, as his parents overlooked much of his misbehavior. His high school senior quote: “partying, New Year's Eve, car accident, bondage, coke, whippets. Good times.” — Which the hosts mock as “something a virgin would write.” (06:47)
• Dual Paths: Dana started as an aspiring rockstar in Boston before getting into finance, eventually blending his love of music with investments, positioning himself as an “artist’s financial advisor.”
• Breakout Moment: Dana’s hustle saves Sub Pop Records—home to Nirvana—by brokering a $20 million buyout with Warner, cementing his reputation as a young financial whiz (11:58).

2. Entering Hollywood’s Inner Circle (15:52–19:11)

• Friendship with Jay Maloney: Via connection with hard-partying CAA agent Jay Maloney, Dana gets introductions to Hollywood’s elite, managing money for stars like Leonardo DiCaprio, Ben Affleck, Matt Damon, Cameron Diaz, and Alanis Morissette.
• The Power of the Referral: Dana’s appeal grows by word-of-mouth among young artists—few vet his credentials due to the vouch of trusted insiders.

3. Bending and Breaking the Rules (19:11–27:15)

• False Claims and Exaggerations: Dana repeatedly inflates his credentials (e.g., claiming he manages Spielberg’s fortune, or faking a Harvard MBA)—a classic ploy that the hosts joke “everyone’s done.”
• Clients’ Blind Trust: Many artsy clients have little financial literacy, and “just having someone deal with your money is enough of a solution when you don’t know anything about money.” (23:56)
• Side Deals and Illegal Practices: Dana’s “concierge” services—where clients’ funds were deposited directly into his group’s account for risky investments—cross into illegality, as hosts liken it to a valet taking your car home (24:56).

4. Escalated Risk, Partying, and Early Calls of Trouble (27:16–38:42)

• Personal Excess: Dana bankrolls lavish parties, exclusive trips (like to Cuba), and bonds closely with celebs (including Leonardo DiCaprio—complete with matching pet cockatoos and “training” them for parties, possibly with cocaine).
  • “These talking birds are basically BFF necklaces with wings.” — Sarah Hagi (30:18)
• Funding Vanity Projects: Dana funnels client money into friends’ startups (like The Standard Hotel and Ford Models), with the hosts noting, “he’s more interested in impressing his cool friends than protecting his clients’ wealth.” (33:55)
• Early Red Flags: Sloppy accounting emerges with Jay Maloney’s family—when they ask for Jay’s earnings, Dana stalls and ultimately issues a check not from the brokerage but his own company account (29:35).

5. The High Life Peaks and the Fall Begins (38:42–50:05)

• Growing Ambition: Dana launches a $100 million VC fund hoping to become a kingmaker in entertainment. He hires a grown-up VP, Soledad, to clean up accounting, but resists meaningful oversight—Soledad eventually leaves when her ultimatum to become president is rejected.
• Media Humiliation: A New York Times Magazine profile portrays Dana as a “downtown sex addict, party boy, pretty boy who’s friends with Leo" (43:43). This public shaming triggers powerful clients (Michael Ovitz, Matt Damon, Ben Affleck, and Cameron Diaz) to flee.
  • “When Dana began showing up on page six more than I did, I knew it was time to get out of there.” — Actor Ed Burns (45:47)
• Chaos and Addictions: Dana parties harder, mixing with clients, as investments tank (notably Iridium and Paradise Music), and he begins robbing “Peter to pay Paul”: shifting funds from lesser-known clients to keep VIPs appeased.

6. Consequences and Downfall (50:05–58:23)

• SEC Investigation and Arrest: As the scam unravels, the SEC launches a deep investigation. Dana is arrested at Newark Airport with a doctored passport and numerous first-class tickets, attempting to escape consequences (50:05).

• Legal Fallout: He pleads guilty in August 2000, serving nearly five years. Subsequent small-time crimes (credit card fraud) show no sign of reform.

• Refusal to Accept Guilt: Even post-prison, Dana insists, “I’m not a thief,” saying he was merely misunderstood, unable to accept the consequences or ethical lapses.

  • “I thought I was gifted with the ability to bring these fields together and... empower the artists...The horrible thing about being painted, the brush is, you know, as a thief, is that I’m not a thief.” — Dana Giacchetto, Vice Interview (52:31)

7. Tragedy and Lasting Legacy (58:23–End)

• Personal Decline and Death: After years of addiction and isolation, Dana is found dead at age 53, a fate the hosts liken to Greek tragedy—with a nod to Icarus more than Cassandra.
• Reflection on Celebrity Culture: The ultimate humiliation isn’t the crime, but being called a “loser” and cut off by the stars—“the worst thing that happened to this guy was that he was called a loser, and not that he took advantage of people.” — Sachi Koul (55:25)

---

Notable Quotes & Memorable Moments

• "The line between cool and cringe is razor thin. And when Dana crosses it, his entire scheme will sink like the Titanic." — Sarah Hagi (05:25)
• “If you smell social desperation on someone who also has a lot of money, run.” — Sachi Koul (58:23)
• “Losers seem harmless because they’re losers, but they will screw you over because they are losers.” — Sachi Koul (58:35)
• “You can fire anybody who works on your team if you think they’re just lame.” — Sachi Koul (45:09)
• “Dana wanted it to be a party in 1992 all the time and… it was a very lonely existence. Even his party friends are starting to fall by the wayside—or descend into real devastation and a real death toll on this scam.” — Sachi Koul (57:20)

---

Timestamps for Important Segments

• 00:00–03:38 Introduction, theme of proximity to fame, table-setting Dana’s rise
• 06:47–09:17 Dana’s youth, personality, Cassandra Group origins
• 11:58–14:35 Saving Sub Pop Records, entry into New York scene
• 15:52–19:11 The Jay Maloney connection, Hollywood A-listers
• 24:56–27:15 Illegal financial maneuvers explained ("valet" analogy)
• 28:19–29:35 Jay Maloney’s family confronts Dana, early signs of fraud
• 29:35–34:02 Exclusive parties, celebrity flattery, risky deals
• 38:42–40:33 VP Soledad’s attempted audit and fallout
• 43:43–46:07 NYT profile fallout, mass exodus of star clients
• 50:05–52:31 SEC arrest, legal unraveling
• 52:31–53:08 Dana’s self-justification, post-prison interviews
• 58:23–58:41 Final reflections, warnings on spotting “losers” with power

---

Final Reflections – Why Dana Was Doomed

The story of Dana Giacchetto underscores the dangers of unchecked access, blurred boundaries between social climbing and fiduciary duty, and the perils of celebrity culture’s tendency to trust insiders without diligence. The episode ends with the recognition that Dana, at his core, was always trying to be seen—and though he loved the limelight, it ultimately burned him.

Lesson:
“If you smell social desperation on someone who also has a lot of money, run.” — Sachi Koul (58:23)

---

Sources and Credits:
Special acknowledgments are given to Vanity Fair, New York Magazine, and Vice for foundational reporting on Dana Giacchetto’s career and downfall. All research, writing, and production credits are listed at the episode’s end.

---

This summary captures the major arcs, insights, and spirit of the conversation, while highlighting standout commentary and dark humor characteristic of the hosts.

Transcript

[Sarah Hagie]

Audible subscribers can listen to all our episodes of Scamfluencers ad free right now. Join Audible today by downloading the Audible app. A note to our listeners, this episode contains mentions of suicide. Please take care when listening. Sachi. I feel like a recurring theme of the show is like, a person who will find any way to get close to celebrity and even if it means doing boring stuff like being their butlers or handling their money. You know what I mean?

[Sachi Cole]

Yeah. A lot of the scammers we talk about don't come into it because of need. They just want to be seen by somebody with name recognition. It's really sad.

[Sarah Hagie]

Yes. And one thing that always gets me is when someone has a legitimately good idea, but they just get way too thirsty getting remotely close to the spotlight, you know?

[Sachi Cole]

Yeah, It's a weird kind of stage fright, almost.

[Sarah Hagie]

Yeah.

[Sachi Cole]

Like you did all that to get

[Sarah Hagie]

there and then you biff it. Exactly. Well, today I'm going to tell you about someone who really couldn't accept his role being behind the scenes despite tapping into a lucrative market of up and coming Gen X stars that we still know today. Our guy almost went out of his way to scam. Despite having it all, it was never enough. It's March 1998, and Hollywood's biggest heartthrob, Leonardo DiCaprio, is watching his latest movie, Cleanup at the Oscars. The film has already won 10 statues, and as Sean Connery opens the envelope to announce Best Picture, Leo is hoping it's about to win number 11.

[Sachi Cole]

And the Oscar goes to

[Sarah Hagie]

Titanic. Leo watches his director, James Cameron, bound to the stage to accept the award while his co star, Kate Winslet, beams from the front row. But there are no cameras on Leo because Leo isn't at the Academy Awards. He's 3,000 miles away in a loft in lower Manhattan, watching the ceremony projected onto a wall. Leo was invited to the Oscars, of course, but he's 23 years old and the most in demand actor of his generation, already commanding $20 million a movie. Attending a rager probably seemed way more fun than walking the red carpet at a stuffy awards show, particularly when the party features guests like Naomi Campbell and Kate Moss and two white cockatoos named angel and Tiberius.

[Sachi Cole]

Oh, wow. Nothing says wealth like mysterious birds.

[Sarah Hagie]

One of these cockatoos belongs to Leo. The other belongs to the party's host, Leo's money manager, Dana Giquetto. Dana is 35, with floppy blonde hair and round, metal framed glasses, and tonight, he seems to be the king of the world. He's got a soho penthouse filled with modern art, a closet full of Prada, and the coolest people in fashion, movies, and music. In his orbit, these A list celebs aren't just Dana's friends. He also manages their money. Dana's client roster reads like the front page of Variety. Ben Affleck, Matt Damon, Cameron Diaz, Courtney Cox, and of course, Leo himself. Some people call Dana the rock and roll broker or the stockbroker to the stars. Altogether, Dana handles millions of dollars for around 300 VIPs. And hosting Leo's Oscar party is Dana's biggest flex yet.

[Sachi Cole]

I think it's embarrassing that, like, your big thing is that you threw somebody else a party. That sucks.

[Sarah Hagie]

It does suck. And it is loser behavior.

[Sachi Cole]

Yeah.

[Sarah Hagie]

Which. Get used to this for the story.

[Sachi Cole]

Okay.

[Sarah Hagie]

Behind all the glamour, there's trouble brewing because Dana has been lying about a lot of things. Like where he went to school, where his client's assets are invested, and how much of their cash he's using to bankroll lavish parties like this one. Dana has been spending millions of borrowed dollars to maintain his man about town reputation. Right now, the champagne is flowing and the music is pounding. But soon, federal investigators will start asking where the money went and who paid for nights like this one. Then Dana will face federal charges, a torrent of bad press, and worst of all, being ghosted by all his celebrity friends. Xfinity tech support. I can't get Jurassic park back online without. Oh, you just need Xfinity. Plug in your gateway and you're good. And with our five year price guarantee, your bill is under control, too. Xfinity.

[Sachi Cole]

Imagine that.

[Sarah Hagie]

Watch Jurassic park with Xfinity restrictions apply.

[Sachi Cole]

Select plans only

[Sarah Hagie]

from Audible Originals. I'm Sarah Hagie.

[Sachi Cole]

And I'm Sachi Cole.

[Sarah Hagie]

And this is Scampfluencers. Come and give me your attention I won't ever learn my lesson Turn my speakers to 11 I feel like a legend. In the late 90s, Dana Giquetto was a money manager to the stars. But his true addiction wasn't money. It was the scene. Dana started out as an aspiring rock star who happened to have a knack for investing. But he didn't want to just be another boring financial advisor. He wanted to be a punk rock money manager, playing the market like a vintage Stratocaster. And for a while, it worked. But seduced by clout, cash, and proximity to fame, Dana began sinking his clients cash into questionable deals, commingling their funds and using their money to fund his extravagant lifestyle. In less than a decade, Dana went from Leo's inner circle to Hollywood pariah. He thinks he's living his Wolf of Wall street dream, but the line between cool and cringe is razor thin. And when Dana crosses it, his entire scheme will sink like the Titanic. This is Dana Giacchetto, star swindler to the stars. It's the 1970s, and Dana is growing up in a middle class suburb of Boston as the golden child of two Italian Americans who weren't sure they'd ever be able to have kids. When Dana finally came along, he was born premature and his parents were terrified he wouldn't survive. When he does, they swear to support him no matter what, which means often looking away when Dana gets into mischief. The result is a kid with a flexible understanding of consequences. In 1980, Dana graduates from high school. Sachi, can you read his senior yearbook?

[Sachi Cole]

Quote, he wrote, quote, partying, New Year's Eve, car accident, bondage, coke, whippets. Good times. This is something a virgin would write. This is someone who has never done drugs before, is scared of Tylenol PM writing down whippets.

[Sarah Hagie]

Also, they let him do that for a senior quote.

[Sachi Cole]

Okay, yeah, I guess no one's paying attention. It's the eighties, Haggie.

[Sarah Hagie]

You're right. You're right. It was different then. They didn't know what was going to happen.

[Sachi Cole]

No, they had not yet said no to drugs. They were just about to.

[Sarah Hagie]

Well, in any case, Dana heads off to UMass Boston and forms a band called Breakfast in Bed. He plays keyboard, sings lead vocals and writes all the lyrics. The band actually starts to take off in the early 80s Boston punk scene. Dana just knows he's on his way to new wave rock stardom. But the band never breaks out of Greater Boston. So Dana takes a side job in the mailroom of the financial firm Boston Safe Deposit and Trust. And despite the white collar world of finance being extremely square, it fascinates him. Dana gets so wrapped up at the firm that he pauses school and starts climbing the corporate ladder.

[Sachi Cole]

This is literally an SNL sketch where a band starts working at a white collar job. And then they're like, actually, the boss

[Sarah Hagie]

is kind of cool. Yeah, I mean, sometimes people, they crave the structure. And Dana learns the ins and outs of asset management and adopts a financial golden rule. Invest conservatively. His philosophy is, this is your client's money, so play it safe. With blue chip stocks in well established companies for the next few years, Dana lives a double life. By night, he's a rocker playing at grimy punk clubs. By day, he's a senior financial analyst making $85,000 a year, which would be over $250,000 today. Eventually, he can't keep up and breakfast in bed disbands. But Dana isn't ready to give up his rock and roll identity. He still sees musicians and artists as his people, much more than stuffy Wall street types. So at 26 years old, he gets a $200,000 loan from his mom and launches his own investment firm for artists and creatives. He calls it the Cassandra Group. Here's Dana explaining the name in a 2014 Vice interview.

[Dana Giacchetto]

Cassandra was a Greek mythological figure, right? She was never believed. So she knew the future, but was never believed. And in investment circles, Cassandra is a contrarian.

[Sarah Hagie]

Punks love being contrarians, and finance guys love to believe they can see the future. It's perfect. Now Dana just needs to find clients who actually will believe him. It's 1991 in New York City, and 29 year old Dana tosses and turns on the floor of his brand new office in soho. He just moved here from Boston after finally graduating from UMass. More than 10 years after he started, he's rented an office in SoHo, the hub of the downtown art scene, where musicians and models rub elbows with movie producers and fancy gallery owners. It's exactly where Dana needs to be to find more clients for his young firm, the Cassandra Group. But New York is expensive. He can't afford to rent an office and an apartment in this swanky neighborhood. So at night, instead of going back to his tiny apartment across the city, Dana, he often crashes under his desk to stay in the more aspirational part of town. Back in Boston, Dana and his girlfriend would host cocktail parties and invite up and coming painters and sculptors from the local art scene. After a few cocktails, Dana would make his pitch. He told them, as a former musician himself, he understands how unpredictable a career in the arts can be. So his investment philosophy is simple. Avoid dramatic ups and downs by investing in boring, predictable companies. But after three years in Boston, Dana felt like a big fish in a small pond. So in 1991, he moved to Manhattan. In New York, Dana starts cold calling downtown galleries to drum up business, including the highly influential Pace Wildenstein Gallery. The gallery president is impressed with Dana's eagerness and hustle, so he connects Dana with his exclusive circle of New York artists. But Dana is still a punk rocker at heart. So while he's still working his way into the New York art scene, he's also hard pitching himself to the ultimate indie music label. 3,000 miles away. Sub pop records. 90s kids will know Sub Pop as the legendary indie label that launched a little group named Nirvana. Dana has a friend who works there and he wants them as a client. So he starts calling their offices over and over. And soon he's taking regular calls with Sub Pop's chief financial officer. Dana learns that despite being home to one of the biggest bands in the world with Nirvana, Sub Pop has been struggling to stay solvent. It's mostly due to atrocious accounting practices, and it's starting to impact the reputation. Bands aren't getting paid and tour vans break down. With no money for repairs, the label needs an influx of cash just to survive. Dana genuinely wants to save Sopp Pop. So he convinces them to hire him as a sort of deal broker to find someone to buy a minority stake in the label. And over the next seven months, Dana orchestrates a bidding war. It's a masterclass in hustle. He pits high powered billionaires against each other. Like calling up Geffen Records to go on and on about Sub Pop's incredible roster of bands, then cutting off the conversation and claiming he has to go talk to other buyers. It's a bold way to negotiate, especially since Dana's never closed a deal of this size before. But it works. In 1994, Dana brokers a $20 million deal with Warner Music Group for a 49% stake in Sub Pop. The label is saved and it still retains a majority of its ownership, so it won't lose its soul. It's a total win. Win for the label and for Dana. Dana is officially on the map, but he's far from satisfied. At just 32, he's conquered the art world and indie music. Next, he's coming for Hollywood. About a year later, it's summer of 1995, and a caravan of rafts is rushing down the Colorado River. Paddling through the rapids are about 20 luminaries of the entertainment and publishing world. They each donated 50 grand to an environmental charity just to be here. There's hotelier Andre Belage, who owns the Chateau Marmont. James Pratt, the founder of Sassy magazine. And of course, there's Dana, trying to look smooth while he rides the rapids. Leading the pack is Dana's new bestie, the mastermind behind this epic fundraiser, an up and coming Hollywood power broker named Jay maloney. Jay is 6ft tall with soft brown hair and a boyish face. He's only 30 years old, but he's already a hotshot talent agent at Creative arts agency, or CAA. Jay likes to party as they say, which is 90s speak for runs on cocaine. His superpower is making everyone in his orbit feel special.

[Sachi Cole]

I think people would also say that about me if I was running on cocaine and had cocaine and could offer cocaine.

[Sarah Hagie]

Yeah, you know, it kind of is, you know, a bit of a social lubricant. Pretty good party favor.

[Sachi Cole]

Yeah. Everybody thinks that the guy who has cocaine is like a great conversationalist.

[Sarah Hagie]

Yeah. In the 90s. Yeah, especially, oh, for sure. When Jay met Dana a couple years earlier, they hit it off right away. Jay quickly invested some money with Dana and started telling his friends and colleagues to do the same, including his boss, CAA co founder Michael Ovitz, and Rick Yorn, high power talent manager representing rising stars like Cameron diaz and Leonardo DiCaprio. Jay's charity whitewater trip introduces Dana to a whole new level of networking. And the timing is perfect. Dana's fresh off the huge sub pop deal and looks like a financial genius. Thanks to Jay's intros, Dana's client list explodes. Stacey Scher, the young producer of Pulp Fiction, becomes a client. So do Alanis Morissette, Tobey Maguire, Michael Stipe from REM and the entirety of the band Phish. Nearly all of these can be traced back to Jay, giving Dana his stamp of approval.

[Sachi Cole]

As a Canadian, I'm mostly stressed out for Alanis. The rest of them can take care of themselves. But what's going to happen to Alanis?

[Sarah Hagie]

If some high powered agent connected me to a financial advisor, I wouldn't really question it. I'm not going to lie.

[Sachi Cole]

Yeah, I would take it. And he signed all my famous friends and also Phish.

[Sarah Hagie]

Exactly. Dana gives them the same pitch he gave his very first clients. A career in the arts is unpredictable. So invest in predictable companies. And that would be a really smart approach if Dana actually stuck to it. But there's one shiny object Dana has never been able to resist. The sparkle of celebrity. And chasing this glow is about to make him reckless. A year later, in 1996, 33 year old Dana is pacing inside his new penthouse. His days of sleeping on an office floor are behind him. Now he lives in a spacious loft in Soho with a view of lower Manhattan and a Bruce Nauman print on the wall that reads, pay attention, motherfuckers. But tonight, Dana is so worked up, he can't even enjoy the view. He's just heard through the grapevine that an old deal has come back to haunt him. Two years ago, Dana got involved with a little company called Moviefone Sachi. Do you remember it Yes.

[Sachi Cole]

I mean, I sort of. I don't remember calling Moviefone, but it was a number that you could call, and it had a very trademark deep voice, and it would tell you what movies were playing in your area. There was a very famous Seinfeld episode about it. Extreme 90s ephemera.

[Sarah Hagie]

I was calling Moviefone. Were you calling Moviefone?

[Sachi Cole]

I wasn't calling Moviefone.

[Sarah Hagie]

I remember looking through the phone book and being like, I'm gonna call Moviefone.

[Sachi Cole]

Right. I would just get the movie listings in the newspaper, in the printed paper on Thursdays.

[Sarah Hagie]

Well, Dana met the Moviefone founders while schmoozing with Hollywood types. And when the company went public in 1994, the Cassandra Group bet big. Dana insisted his clients be given a chance to buy in. But the stock tanked almost immediately. And Dana did something shocking, or to put it another way, illegal. He refused to pay for the shares he ordered, skipping out on a $100,000 bill. Amazingly, no one seemed to have filed an official complaint at the time. But now rumors about Dana cheating Moviefone are starting to swirl. Probably because his reputation is on the rise. And for people who know the rules of finance, this looks bad. Not only did Dana back out of a stock purchase, he placed an order on behalf of at least one client who didn't even want Moviefone stock in the first place. Dana knows that in this industry, reputation is everything. He can't afford to have people talking behind his back. So he settles his debt with company funds, and the rumors eventually subside.

[Sachi Cole]

Okay, so here our friend is no longer obeying his own financial philosophy of, like, being boring with your money and making good bets. And I don't think he would have ever paid this money back if it wasn't going to cause him reputational damage.

[Sarah Hagie]

Of course, the Moviefone deal is a harbinger of things to come, because it's clear that Dana isn't sticking to conservative blue chip investments. He's starting to get more creative with his clients cash without telling them. Moviefone should have been a wake up call. Instead, it seems to be proof that he can break the rules and still walk away. But the next time Dana gambles with other people's money, the stakes will be higher and the fallout won't be so quiet. I feel like. It's 1997 in Los Angeles. And in the lush green courtyard of the Chateau Marmont Hotel, Dana is in full pitch mode. Sitting across from him is film producer Bill Robinson. Bill is Diane Keaton's business Partner. And hopefully Dana's soon to be client. Dana cracks open his laptop and starts walking Bill through potential portfolio options. He also sprinkles in a few enhancements. Dana tells him he's part owner of the Chateau Marmont, and he's not. He also tells Bill he manages over a billion dollars in client funds. He does not. Dana makes a habit of exaggerating details like this. He tells people he manages $7 million for Steven Spielberg, but that's also a lie. And one of his favorite lines is that he's just a few credits shy of an MBA from Harvard, when the truth is that he only took a few extension courses there at night.

[Sachi Cole]

That's like when Tyra Banks was talking about how she graduated from Harvard, and

[Sarah Hagie]

it was like that weekend business course.

[Sachi Cole]

Yeah, she, like, took one online. Like she was on a zoom. Yeah, classic scam. I wouldn't even count this one. Everyone's saying this one.

[Sarah Hagie]

Well, Dana brushes his blonde bangs out of his eyes and tells Bill he usually doesn't take on clients without at least a $1 million investment. But he hints that he might be able to bend the rules today if Bill moves quickly. The pitch kind of sounds like Dana's selling a timeshare, but Dana really is on a hot streak right now. His clients have been seeing sweet returns lately, sometimes north of 40%. Can you read what Courteney Cox said about Dana in an interview with the New York Post?

[Sachi Cole]

Yeah. She said, quote, every time everyone's panicking about the stock market going down, I just say, go, Dana. Ugh.

[Sarah Hagie]

Oof.

[Sachi Cole]

That's not gonna age well, is it, girl?

[Sarah Hagie]

If the stock market's going down and you're making money, something is up or you're. You're doing something evil.

[Sachi Cole]

Evil?

[Sarah Hagie]

Yeah. Yes, something bad is happening. Basically, according to Dana, he gets such great returns because he invests the money in stable, boring companies like AT&T. But of course, the truth is a lot more complicated. As a money manager, Dana has total freedom to make whatever trades or investments he thinks are smart play for his clients. It's a lot of trust to give one person, but his clients seem fine with it. Perhaps because the accounting for these trades should be pretty straightforward. This gets a little dense, but please stay with me. Dana keeps his client's stock holdings with a Boston brokerage firm called Brown and Co. If they own 10 shares of Nike, for example, Brown and Co records those shares. If the client wants to see how their Nike stock is doing, they can read their Brown and Co monthly statements. And if they Want to buy or sell that stock. Dana calls Brown and Company to place the order. But Dana also handles what he calls private placement deals. Over lunch at overpriced restaurants, Dana will hear that someone is building a new hotel or starting a new business, and he'll make handshake deals to invest on behalf of his clients. Brown and company does not handle these deals. They are all Dana. And Dana doesn't always bother to tell his clients where their money's going to which, to be fair, is how some of his clients seem to like it. They're busy, and they're paying him to make these kinds of decisions.

[Sachi Cole]

Dana's dealing with really rich people, but it's interesting because he's also dealing with artists with a lot of money, and they're not really inclined to think too hard about their finances. They maybe don't have a ton of financial literacy. Like, we see this a lot with celebrities who burn through their cash or even athletes who burn through their cash. Like, just because you're rich doesn't mean you really know what to do with that money. So I guess it makes sense that they'd just be like, I trust you. Do something with it.

[Sarah Hagie]

Yeah. I also feel like just having someone deal with your money is enough of a solution when you don't know anything about money. Right. And in order to move money quickly without chasing down client signatures, Dana develops a workaround. He has Brown Co. Cut checks made out to his client, say, Courtney Cox. Then, because he manages Courtney's money, Dana is able to deposit that check made out to her straight into the Cassandra Group's bank account. From there, he can invest in whatever deal he wants. In Dana's mind, this is essentially a concierge service. It's like giving the cleaning staff access to your home or handing a valet the keys to your car. But there is a problem with Dana's workaround. It's totally illegal. In the eyes of the law, Depositing someone else's check into your account is stealing. It's less like giving the valet your keys and more like the valet driving your car to his house and promising to return it later. Which, to be fair, is what I would do if I was a valet. Yeah.

[Sachi Cole]

I would also be like, well, you're not using it. I can't use it. Like, what's the problem?

[Sarah Hagie]

Nothing bad's gonna happen. It's all good.

[Sachi Cole]

I think there is a reason why we don't work in financial services.

[Sarah Hagie]

Yes. And why we're not valets.

[Sachi Cole]

Well, that, too. But one is probably Worse for us than the other. You can only kind of steal one car at a time. You know, you can kind of do this over and over and over again at the same time.

[Sarah Hagie]

Yeah. It's also hard for clients to find concrete info about how these deals are doing. The money's all going into Cassandra's coffers, forming a single slush fund. So picture that valet driving 1000 cars to his house and never writing down whose car is whose. To your point, in Dana's mind, he just keeps things fluid for his VIPs. But what he's really doing is freely commingling his client's money with his own. And soon, this will present a problem for someone who actually needs answers. It's November 1997, and while Dana's career is soaring, one of his closest friends is hitting rock bottom. CAA agent Jay Maloney has spent the last year in and out of rehab for a crippling cocaine addiction. For a while, Dana thought Jay might be turning a corner. Earlier that fall, Jay had gotten clean and was staying at a halfway house. Then, one day in November, Dana gets a call from Jay, who sounds panicked. He tells Dana that a drug dealer is threatening him. He needs Dana to withdraw $6,000 from Jay's account and bring it to him. Now Dana's got a dilemma. On the one hand, Jay is obviously struggling, and giving him this money could jeopardize his recovery. On the other hand, Jay is asking for his own funds. And as Jay's money manager, Dana feels he's legally obligated to comply. Now, Dana's not quite right about that. Legally, he has some leeway to deny a transaction if he believes it will be used to commit a crime, which would include buying illegal drugs. But Dana has trouble saying no to his friends. He wants everyone to like him.

[Sachi Cole]

What an embarrassing reason for forking over enough money to an addict for them to harm themselves. Like there isn't a good ethical argument here, I don't think.

[Sarah Hagie]

Yes, and also, you care so much about people liking you. Maybe don't be messing with their money, bro. So Dana withdraws the money and delivers it to Jay, who takes it and immediately disappears. Four days later, Jay resurfaces in a New York hospital, recovering from a drug binge and a suicide attempt. Dana is devastated and feeling pretty guilty. But when Jay's family confronts him, he goes on the defensive. Here's what Dana later tells a Vanity Fair reporter. I felt horrible about it, but I don't feel I did anything that I wouldn't have done for Someone I loved and cared about. I don't think I was an enabler with Jay. I tried everything to help Jay, but Jay's mother sees it differently. Sachi, can you read what she said to that same reporter?

[Sachi Cole]

Yeah, she said, quote to me, he tried to kill Jay. In fact, he almost killed him.

[Sarah Hagie]

Oof.

[Sachi Cole]

Yeah, that's brutal. Jay is an adult and he is responsible for himself. But I can understand feeling like this for sure.

[Sarah Hagie]

Jay eventually recovers and to Dana's relief, doesn't even blame him. But Jay's family takes action, sending Dana a formal letter requesting that Jay's money be transferred to a trust and that can't be touched without his family's permission. It's a way to protect Jay from himself. However, when the Maloney's actually try to get Jay's assets, they hit a wall between Jay's art collection, stocks and liquid funds. They estimate he has between 2 to 3 million dollars invested with Cassandra. But oddly, Dana won't reveal exactly how much. The Maloney spend months trying to get an earnings statement, a spreadsheet, some numbers jotted on a napkin. According to Jay's family, Dana keeps them waiting. Eventually the Cassandra group sends a check. But it doesn't come from the brokerage firm where Jay's money was supposedly being held. The check comes from the Cassandra Group. Jay's money was clearly mixed in with everyone else's.

[Sachi Cole]

Very sloppy, Very obvious. Sloppy and obvious.

[Sarah Hagie]

Oh, big time. And somehow this doesn't destroy Dana and Jay's friendship. But Jay's family can clearly see that Dana's accounting is fishy. And the more money Dana manages, the harder it will become to hide this. Because Dana, like Jay, has an appetite for excess. And his next moves are going to require even more cash. It's the holidays of 1997 and 35 year old Dana has a treat for his VIP use. He's invited around 30 of his most influential clients on an exclusive trip to Havana, Cuba. Dana had to get special permission from the American and Cuban governments. So this trip is quite the flex. And the guest list reads like a Vanity Fair spread. There is Jesse Dillon, Bob Dylan's son, taking in the sights next to Chris Cuomo, the news anchor and brother to future governor Andrew Alanis. Morissette is also here. And near the front of the pack is the 23 year old movie star Leonardo DiCaprio. By this point, Dana and Leo are basically besties. Or at least that's how Dana sees it. When Leo needs a place to crash in New York, he often ends up At Dana's Soho penthouse. And yes, this is the penthouse where Dana and Leo keep their cockatoos, angel and Tiberius. These talking birds are basically BFF necklaces with wings. We actually have some pictures of the guys with their birds. Sachi, could you please describe them?

[Sachi Cole]

I don't think we talk enough about how Leonardo DiCaprio is a loser. Because these photos are of a loser. Yes, in one he's wearing a white tank top and a backwards baseball cap. And in another he's wearing a T shirt. I think he's smoking a cigarette. And there's a big white bird in both of them. They look like magicians. I don't even know what to say.

[Sarah Hagie]

Yes, and you know, at least he's only. He's a 23 year old movie star who is willing to do anything. But Dana's far too old to be doing this stuff.

[Sachi Cole]

Yeah, and Dana's really old to be sitting there on this couch with a bird on his shoulder.

[Sarah Hagie]

Yes. And I really cannot stress enough that Dana's loft is no place for exotic pets. Here is Dana explaining how he trained his birds to party.

[Dana Giacchetto]

Really smart animals. It's like, you know, you put cocaine in a little in a nozzle here and the parrot will say, you know, coke and get the cocaine versus water.

[Sarah Hagie]

Wait, is he just giving the bird coke?

[Sachi Cole]

Cause that's not a party trick that the bird is getting addicted to cocaine. That's just feeding a bird cocaine.

[Sarah Hagie]

Yeah, but it has a trick if you really think about it.

[Sachi Cole]

Is it?

[Sarah Hagie]

No, it's not.

[Sachi Cole]

Okay.

[Sarah Hagie]

Well by this point, Dana is doing everything possible to dazzle his celebrity friends. When he's not hosting an exclusive 30 person tour to an embargoed nation, he's taking them out to lavish dinners and racking up five figure bills. Dinners that are often being funded by the same big slush fund that his clients money goes into. So these outings and dinners are essentially being paid for by the very people he's wining and dining. Dana's also financing his VIPs pet projects. When Andre Belage needs funding to build a trendy new hotel called the Standard, Dana convinces his other clients to invest. And when Andre's wife, Katie Ford, the CEO of Ford Models, starts her own business, Dana sinks his clients money into that too. Unlike some of Dana's other moves, this isn't technically illegal. But it does introduce a lot of risk. He's using client A's money to prop up client B. Whether or not client B's project is a solid investment, remember Dana's whole invest in blue chip stock strategy. This isn't that. It's more like what happened with Moviefone where he gambled with his client's money just because he was friends with the project's founders.

[Sachi Cole]

I think there is a bit of a difference now between him taking the money of his like rich and famous friends and you know, putting it in a fund or whatever and moving it around. And maybe he's irresponsible with it and now like funding their little vanity projects like that is a level of obsequiousness beyond repair.

[Sarah Hagie]

Yes, but luckily not every risky investment goes belly up like Moviefone did. The Standard Hotel, for example, is still standing. The point is Dana's more concerned with impressing the Andres and Katies of the world than he is with protecting his clients wealth. And the bigger he dreams, the more money he needs. By any means necessary. It's New Year's Eve 1998. Dana is 36 and hosting a rager with his most impressive guest list yet. There's Leo, of course, but also Winona Ryder, across the room from her famous ex, Johnny Depp. Q Tip from A Tribe Called Quest is djing. And over in the corner are a couple of Bostonites named Ben Affleck and Matt Damon. The party gets so out of hand that just before dawn, Tobey Maguire and Leo decide to climb the water tower of Dana's building. The party eventually triggers a fire alarm at 7am on New Year's Day, which I think makes Dana officially the worst neighbor in lower Manhattan. But Dana doesn't care about the damage. The wilder the party, the bigger the clout. And more clout is what Dana is seeking this year. Dana has big dreams for the Cassandra Group. He's made some key hires that he's sure will take the company to the next level. First, he found someone to help him clean up his accounting. Remember, sloppy bookkeeping is what almost bankrupted Sub Pop Records all those years ago. And even someone as chaotic as Dana knows he needs to get it together. So he hires an investment banker with a serious face named Soledad Bastianczyk. Soledad is a Yale Law School grad with superb credentials. And she's actually taken a pay cut to become a VP at Cassandra Group. On any given day, Gwyneth Paltrow could just breeze in for lunch. That's gotta be more exciting than clerking at a law firm.

[Sachi Cole]

It seems that they've hired Soledad to come in and kind of be like a bit of a grown up. Yeah, and to manage everything A little better, but they are still picking people who would take a job and a pay cut in order to see Gwyneth in the 90s. That's maybe a bad start.

[Sarah Hagie]

Yeah, I mean, maybe Soledad, as skilled as she is, could be willing to look the other way for the sake of celebrity, you know? And Dana's also started a partnership with a 40 something venture capitalist named Jeffrey Sachs. Jeffrey's silver fox aura and background in politics set him apart from Dana's wannabe punk vibe. Jefferies, a serious investor who got his start in the public sector working for two different New York governors. Now a trusted financial consultant, his Rolodex is full of big finance firms, healthcare groups and entertainment networks. These are whales, huge institutions that Dana would never have access to on his own. Jeffrey's sterling reputation is the key to Dana unlocking deals on a much larger scale. In October 1998, Jeffrey and Dana Co found $100 million venture capital fund underwritten by Chase Manhattan Bank. They call it Cassandra Chase Entertainment Partners, but its nickname is just the fund. Venture capital funds or VC funds exist to invest in promising startups. In this case, the fund is looking to invest in new entertainment companies they think could be the next big thing. And that, Dana thinks will elevate his status from stockbroker to kingmaker. But the same manic energy that makes Dana magnetic also makes him a liability. And it won't take long for his new partners to realize that. It's January 1999 in Maya Bay, Thailand, an idyllic island covered in lush jungle and ringed by steep cliffs. The air is warm and humid and the calm sea sparkles a perfect turquoise piece blue. But Dana can't see any of it because he is dead ass asleep, stretched out on the vinyl cushions of the boat where he and Leo were slamming cocktails the night before. Dana's here to visit Leo on the set of the beach, where Leo is playing a young backpacker seeking adventure in Thailand. But now that Dana's made it here, he's not exactly treating it like a client trip. Instead, it's basically one big party in paradise.

[Sachi Cole]

I don't want to hang out with anybody who manages my money. And I think it's suspicious if somebody works with you or in fact for you and is having too much fun on your dime.

[Sarah Hagie]

Yes. And while Dana slurps up my ties in the sun, back in snowy New York, Cassandra's new vp Soledad is freaking out. She's starting to understand just how impossible it is to sort out what Dana's been doing. First of all, there are massive discrepancies in the ledgers. A client might call thinking he has $75,000 in his account, only to discover the real total is $20,000 less. Others call in thinking that they own bonds of AT&T because Dana told them they did. But those bonds are nowhere to be found. Soledad starts to worry that Dana's bookkeeping isn't just sloppy, it is full of intentional lies. When Dana returns to the office, tanned and smiling, he's shocked to discover that Soledad is coming for his head. She tells him the only way forward is a forensic accounting audit to go through his books line by line. Jeffrey Sachs, Dana's partner in the fund, agrees. So Dana relents, even though the audit itself costs a quarter million dollars. But Soledad doesn't stop there. She calls a company wide meeting and suggests that if the audit finds anything shady, Dana should exit the securities business and leave her in charge. Two months later, she sends Dana a wild four page letter citing everything he's done wrong, from his excessive travel and entertainment bills to his inaccurate client statements. She demands that if Dana wants her to stick around and salvage the company, she wants to be promoted to president of the Cassandra Group. She signs this note with a smiley face.

[Sachi Cole]

Vampir. Wow, I love her. Yeah, I hope she gets everything at the end.

[Sarah Hagie]

But craziest of all, her power play flops. We don't know if the forensic audit actually happened and if so, what it found. But Dana refuses to agree to Soledad's terms. And a few months later, she leaves the company to become a writer. Having survived an attempted coup and a narrow brush with regulation, Dana turns his attention to a new project, one he believes will cement his legacy. Instead, within weeks, it will destroy him. And the friend who helped him build it will pay the ultimate price. I feel like a legend. It's April 1999 and Dana is sitting in the Cassandra offices, brimming with excitement. For the past few months, he's been obsessed with his latest pet investment, a struggling media company called Paradise Music and Entertainment. Paradise had been limping along producing albums, music videos and commercials. But by last Christmas, it was nearly bankrupt. That is, until Dana directed several million dollars worth of clients money into it. He convinced celebs like Ben Affleck and Matt Damon to invest. He also invested funds on behalf of Benicio, del Toro, Cameron Diaz, screenwriters and agents. He envisions an exciting new production hub, churning out films starring Leo and Benicio and music videos and albums with Phish, Alanis and Rem paradise could be the thing that finally makes Dana as famous as his clients. The move that transforms Dana from just a money guy into a mogul. And who better to run it than a man Dana believes deserves a second chance. His longtime, newly sober friend, jay Maloney. In April 1999, Dana hires Jay as president of Paradise. He feels like a job will give Jay purpose. He's no longer a practicing agent. After spending months working to stay sober, Dana figures it'll be good for Jay to focus on some real work. But as April turns to May, something happens that rattles Dana's world. The New York Times Magazine publishes a long feature on Hollywood mogul Michael Ovitz. Michael Ovitz was an early client of Dana's and was Jay's former mentor at caa. Dana went record with the Times reporter, giving what he thought were fantastic quotes. But when the article was published in May 1999, it paints Dana as kind of a joke. The reporter refers to his bangs as a flock of seagulls haircut. And she describes how Dana interrupted their interview to shout, quote, get me Leo and get me Michael. But the thing is, there didn't seem to be anyone else in his apartment at the time. As far as she could tell, he was shouting to no one. Here's just one quote from this piece. Sachi, can you read it? Yeah.

[Sachi Cole]

It says, I represent artists. Chiquetto says, waving his arms around the room. I'm tired of everyone referring to me as a downtown sex addict, party boy, pretty boy who's friends with Leo. I am interested in creating equity.

[Sarah Hagie]

He's like, everyone keeps calling me a pretty boy and that I'm so fun, and I'm just not like that.

[Sachi Cole]

Just a guy running around screaming, being like, don't put it in the paper that I'm mad.

[Sarah Hagie]

Everyone thinks I'm just like Leo and guys, I'm so much more than that. Well, misappropriating client funds is one thing, but looking like an unhinged douchebag in the New York Times Magazine, that is catastrophic. Shortly after the profile comes out, Michael ovitz withdraws his $300,000 investment. Ovitz says he's not leaving Dana because of the profile. He claims it's just because his financial statements are too hard to decipher. Sure, once Michael is out, a lot of actors follow suit. No more Cameron Diaz. No more Courteney Cox. Matt and Ben get out almost immediately after joining. They don't appreciate the way Dana constantly drops names, including theirs, but then later told a reporter that the get me Leo moment was what really sealed the deal.

[Sachi Cole]

Yeah. Like, you can fire anybody who works

[Sarah Hagie]

on your team if you think they're

[Sachi Cole]

just lame, of course.

[Sarah Hagie]

And that would do it. Yeah. It's like you're uncool. And that is the biggest sin in Hollywood, really.

[Sachi Cole]

It's one of the worst things you can do to Ben Affleck, I'm sure.

[Sarah Hagie]

During this time, Dana's hours become more erratic. He rolls into the office in mid afternoon after clubbing and popping Vicodin all night. D has always said that partying keeps him on the same wavelength as his A list clients. But not all A listers want their money manager doing lines in club bathrooms. Sachi, can you read what actor Ed Burns reportedly said about Dana's nightlife activities?

[Sachi Cole]

Yeah. He said, quote, when Dana began showing up on page six more than I did, I knew it was time to get out of there. Yeah. The trouble with what Dana was doing was that he started to get more attention than his clients. And it's not even about it being like, good or bad attention. They just don't want anybody to get more than them. Of course they're going to be mad.

[Sarah Hagie]

Yeah. And it's like, you're not supposed to be there, buddy.

[Sachi Cole]

Yeah.

[Sarah Hagie]

As celebrities start to desert him, Dana also sees some of his major investments go south, including a telecom company called Iridium. Its stock tanks almost immediately after he sinks millions of his clients dollars into it. And Paradise Music. Sadly, that doesn't pan out either. Turns out putting Jay in charge was a horrible mistake. Dana thought having a project would give his friend a purpose. But he also put a ton of pressure on Jay to make paradise succeed because he'd poured so much of his clients money into it. But leading a corporate turnaround is famously difficult, even without a president who's fighting to stay clean. Jay was only a few months sober when he took the job in April 1999, and the pressure got to him. Before long, he was using again. In August, just five months into his tenure, Jay stepped down from his position. But Dana barely noticed. He's got bigger problems because Leo is about to leave him. Leo probably never looked too closely at his financial statements, but when they came at all. But by late summer, the young star has clocked the situation. All told, Leo had more than a million dollars invested with Dana, and he ended up losing about 20% of it. In October, Leo officially parts ways with Dana. So do the guys at the fund. Dana's big VC project. And just one month later, in November 1999, Jay Maloney is found dead in his bathroom. He died by suicide at the age of 35. Jay's passing breaks Dana emotionally. Leo may have been his trophy pal, but his friendship with Jay ran deeper. Dana can't process that he may have played a role in Jay's decline. He starts behaving more erratically, popping pills and freaking out his friends. Paradise's stock plunges, sending most of its investors money up in smoke. And then Dana's behavior goes from desperate to despicable. Determined to hide his losses from his A list clients, he starts dipping into the accounts of his less famous clients. Essentially, he borrows from clients whose names aren't on IMDb and shifts it to clients whose names grace Variety's front page. And of course, he sometimes takes some for himself. In late December, two days after Christmas, the New York observer publishes a scathing expose on Dana. It unpacks basically every lie or embellishment he's ever told, including the fact that Harvard has no record of him being a student there. That same month, the band Phish discovers around $4 million missing from their account. And Dana doesn't even fight it. He just signs a letter of confession. One by one, his few remaining clients disappear. This New Year's Eve, his party has way less star power. Only his most faithful friends are in attendance. And he thanks them by forcing them to listen as he reads from the Greek tragedy Agamemnon as the ball drops behind him to ring in the new millennium.

[Sachi Cole]

I gotta tell you, Sarah, of all of the parties described herein, this one seems the most compelling to me. It's about to be 2000. Everyone's scared. They think the planes are gonna fall out of the sky. Nothing's gonna work. People are panicked. And they're all in this weird penthouse, probably with a guy who I would assume is doing, you know, weapons grade amounts of cocaine. And he's making them listen to a Greek tragedy while he frets about the rest of his life. That is exactly the kind of New Year's Eve party you wanna have been at so that you can talk about it forever. If I was at that New Year's party, I'd be talking about it today.

[Sarah Hagie]

Yeah, I would have written a film about it at that point. You know, it would be my whole career. So in less than a year, Dana has gone from the most talked about money manager in New York to a social pariah. He thinks the worst is over. But unbeknownst to him, the securities and Exchange Commission has quietly been making calls to Dana's Clients for the past eight months. They're building a case against him, and the hammer is about to drop. It's April 2000, and at Newark International Airport, a flight from Las Vegas has just touched down on the tarmac. As the passengers start streaming out, a few heads turn because one of the first class passengers is being arrested in front of everyone. Dana Giqueto is is handcuffed and taken into federal custody. The SEC alleges he stole nearly $10 million in misappropriated or missing customer funds. He could be facing 20 years in prison. During his arraignment, Dana was instructed to stay put. But instead, he went to Vegas with his girlfriend. When he's nabbed at the New York airport. On his return, he's holding a doctored passport, 80 first class plane tickets, and four grand in cash. At his next hearing, his defense attorney argues Dana was just looking for a romantic spot to propose to his girlfriend. But the judge is definitely not buying it. He revokes Dana's bail, which means Dana is headed to a federal prison facility. Reality finally starts to sink in. Four months later, in August, Dana pleads guilty to one count of financial fraud and is sentenced to nearly five years in prison. In 2002, he gets out early for good behavior. For the next few years, Dana tries his hand at a few side hustles like an upscale food startup, but nothing really takes. In 2014, Dana is indicted again for charging $10,000 worth of food, travel, liquor, and dental work to a friend's credit card. Dana pleads guilty and is sentenced to two years probation. In an on camera interview with Vice later that year, he chalks it all up to a misunderstanding, just like everything else he's ever been accused of. Here's Dana explaining why his crimes weren't actually crimes.

[Dana Giacchetto]

I thought I was gifted with the ability to bring these fields together and I could empower the artists by demystifying the capital markets for them and helping them. And the horrible thing about being painted, the brushes, you know, as a thief, is that I'm not a thief.

[Sarah Hagie]

Uh, it's like you kind of are though, bro.

[Sachi Cole]

That's like literally what he is. The definition of stealing is sort of what he did, right?

[Sarah Hagie]

Yes. But I mean, is he really a thief in his mind?

[Sachi Cole]

Well, no, he's not, because he does paintings.

[Sarah Hagie]

Exactly. He's punk.

[Sachi Cole]

Yeah.

[Sarah Hagie]

Well, that is the frustrating thing about Dana. Even when directly confronted with his mistakes by reporter after reporter, he genuinely seems like he hasn't learned anything from them. And tragically, he never will. It's A sunny day in Manhattan in June 2016. Sunlight streams into the windows of Dana's apartment on West 100 street, seven miles north of his old Soho neighborhood. A knock raps hard on the door, but Dana doesn't answer. Dana spent the previous week partying hard and self destructing, mixing Vicodin and cocktails, overdosing, being revived at the hospital and heading back out to the bars again. He got into a scrap with bouncers outside of a club where he used to saunter through the door. Dana's ex girlfriend and the mother of his two kids tries to reach him on Saturday night, but he doesn't call her back. It's a downward spiral that looks a lot like the one his friend Jay experienced before he died. And now, in his quiet uptown apartment, Dana's own spiral has reached its end. His roommate discovers Dana unresponsive in bed and calls 911. But it's too late. Dana Giqueto is dead at the age of 53. Dana named his company for a doomed mythological prophet. But if this story is a Greek tragedy, Dana isn't Cassandra. He's closer to Icarus. He flew high and fast before ultimately being brought down by his own hubris, greed and pride. In the aftermath, there is one detail Dana might have appreciated. And headline after headline, he's referred to as the stockbroker to the stars. His name is splashed across newsprint and forever linked with Ben Affleck, Matt Damon, Courteney Cox, Naomi Campbell, and in every single article, Leonardo DiCaprio. Sachi. Is it crazy to you that, like, his downfall wasn't even necessarily just the mismanagement and thievery and all that, but that he came off as an absolute loser to a reporter?

[Sachi Cole]

Yeah, I mean, we've seen stories like this before. Part of it almost reminds me of, like, Lou Perlman, who really wanted to be kind of like in the gang, but couldn't. And so the best he could do was, like, hold him hostage in a way. But it's such a tragedy that the worst thing that happened to this guy was that he was called a loser and not that he took advantage of people and took their money. And he had the trust of a lot of really vulnerable artists. It wasn't just like, super famous people.

[Sarah Hagie]

I think they all knew he was a loser and they were kind of waiting for confirmation that he was unhinged enough to sound like a loser on the record.

[Sachi Cole]

When is Leonardo DiCaprio going to look in the mirror and ask why he is surrounded by these people all the time?

[Sarah Hagie]

Yeah. I mean, think about it. He's, like, former child actor who got so famous in a time where, like, there wasn't the same level of scrutiny in social media following his every move. And I think he just kind of is susceptible to losers who will let him do whatever he wants. But it is pretty interesting how often it seems like Leonardo DiCaprio's around a loser. Mm.

[Sachi Cole]

I feel like we've covered so many financial scams. This kind of falls into a category we've seen before. Did you learn anything about how to avoid such scams? Cause so far, what I'm learning is just, like, don't be rich if you don't have that kind of money, you won't meet Dana.

[Sarah Hagie]

You know, I think it's just, again, this is, like, one of those situations that is so easy to fall into. I think regardless of being rich or famous, it's like knowing someone who someone else is vouching for without doing any type of due diligence to figure out if the person's legit or not. And, like, yeah, artists don't know anything about money. And I just think it's so boring that, like, these people weren't motivated to see if it was a scam or not because they're like, money. Ugh, who cares? Figure it out.

[Sachi Cole]

For me, this is a weirdly simple one. It's just like, a simple failure of personal ethics. He already had associations with all these people. If he could have just been happy with, like, a little piece of it, but it wasn't enough. And so he just kept lying and kept lying and kept lying. You know, Dana was stuck in Arrested Development. Like, he wanted it to be a party in 1992 all the time, and he couldn't have that. And so I imagine it was a very lonely existence. Like, even his party friends are sort of starting to fall by the wayside or to descend into, like, tragedy, into real devastation and, like, a real death toll on this scam. Interestingly enough.

[Sarah Hagie]

Listen, I think he was really talented in some way. Like, he clearly had some skills. It's just like, it was bound to crash and burn. I don't think he ever thought he did anything wrong. I think he is the kind of person who probably always thought that he was just doing the thing everyone else was doing to get by, which is basically every scammer.

[Sachi Cole]

Yeah, I guess the lesson, Sarah, is that we need to stay away from losers. If you smell social desperation on someone who also has a lot of money, run.

[Sarah Hagie]

Yes, of course. It's like, losers seem harmless because they're losers but they will screw you over over because they are losers.

[Sachi Cole]

Words to live and die by. Follow Scamflancers on the Audible app or wherever you get your podcasts. You can listen to all episodes of Scamflancers ad free by joining Audible from Audible Originals.

[Sarah Hagie]

This is Dana Swindler to the stars from Scamflancers. I'm Sarah Hagie.

[Sachi Cole]

And I'm Sachi Kol. If you have a tip for us on a story that you think we should cover, we please email [e-mail] we used many sources in our research. A few that were particularly helpful were Leveraging the Stars by Maureen Orth for Vanity Fair, you Will Make Money in youn Sleep by Emily White Profit and Loss by Nikki Fink and Kevin Gray for New York Magazine and the Real Wolf of Wall street, produced by Gianna Tavone and Scott Pierce for Vice, Katie

[Sarah Hagie]

Clark Gray wrote this episode. Additional writing by us Satya Cole and Sarah Haggie. Olivia Briley is our story editor. Our senior producers are Sarah Enny and Ginny Blume. Our associate producer is Charlotte Miller. Our managing producer is Desi Blalock Fact Checking by Gabrielle Joliet Sound design by James Morgan. Additional audio assistance provided by Augustine Lim. Our music supervisor is Scott Velasquez for Frisson Sync. The executive producer for Audible is Jenny Lauer. Beckman, head of Creative development at Audible is Kate Navin. The head of Audible Originals North America is Marshall Louie. The Chief Content Officer is Rachel Gyazza. Copyright 2026 by Audible Originals, LLC Sound Recording Copyright 2026 by Audible Originates, LLC Legend.