Dana Giacchetto On June 12th, 2016, 53-year-old Dana Giacchetto
was found lying in his bed after a long night of partying in Lower Manhattan.
The former money-manager passed away before they even got him on the stretcher.
Many people wondered if some of his former clients, particularly Leonardo DiCaprio, would
release a statement to mark his passing.
However, almost none of Giacchetto's so-called "friends" mentioned much of anything, despite
him having managed millions of their dollars back in the day.
Early Life Giacchetto grew up in a middle-class town
in Massachusetts, where he played keyboard in a punk rock band.
As the rock-stardom dream faded, and pivoted towards finance in his early 20s.
He didn't handle anyone's money, nor did he help anyone's grandma set up a bank account.
Instead, Giacchetto worked on a team that helped install and support a computerized
account system for a Boston bank.
How exciting!
Giacchetto stuck out as someone who aspired to be somebody, even while working such a
mundane job.
According to his boss, Giacchetto was fun, very smart, and a genuinely hard worker.
Despite his young age, he managed his own stock portfolio, which included shares in
Disney, a stock many investors held bearish sentiments for during the late 80s.
Disney stock would eventually rise in the early 90s as the so-called Disney Renaissance
began.
Giacchetto rose along with it.
Time Warner Giacchetto landed his first big deal in 1988
after a friend from Boston told him about her connections at an underground Seattle
record label called Sub Pop.
The label boasted signees from the grunge scene taking Seattle by storm.
But, in 1988, grunge had yet to move out of its roots and Seattle to become mainstream
music.
So, the business savvy Giacchetto did not call them until 1991, when Sub Pop found itself
in a financial pickle.
Grunge was rapidly rising in popularity, and Giacchetto saw an opportunity to take advantage.
Three years later, in 1994, Giacchetto brokered a deal with Time Warner.
Sub Pop would sell 49% of its label to Warner for $20 million, a price that experts estimate
was several times higher than the label's intrinsic value.
To drive the price up, Giacchetto used the leverage Sub Pop had: they owned the rights
to Nirvana.
The deal gave Giacchetto a taste of success.
It also exposed him to the glitz and glam of the entertainment industry, which seemed
to match Giacchetto's gregarious personality.
Giacchetto rode high on the success of his investment firm, the Cassandra Group.
However, Giacchetto's connections with a New York gallery owner put the young fund manager
in contact with Hollywood agent Jay Moloney.
Moloney put Giacchetto in contact with Rick Yorn, a talent manager captivated by a handsome,
relatively unknown, young actor Leonardo DiCaprio.
Cassandra Group Up until Giacchetto met the Gen X actors of
Hollywood, Cassandra Group had been a small-time operation.
The firm's initial $200k had come from his mom's treasury bonds.
Besides the bonds, Cassandra did not have much to boast about.
Giacchetto's first clients were artsy blue-collar workers around Boston.
Giacchetto offered these workers safe blue-chip stock investments and bonds, a strategy he
would maintain even after turning his attention to young up-and-coming Hollywood stars.
Giacchetto also developed a new marketing strategy for who he called "creative people."
His new market was, after all, actors, actresses, directors, writers, and other individuals
who Giacchetto believed were not comfortable with discussing money management and economics.
Giacchetto used his charm and "left-brained" proclivity to break down investing concepts
to people he deemed "right-brained."
However, it was Giacchetto's infectious personality that won clients over to Cassandra.
His mother once proclaimed, "it's impossible for anyone to not like you," and she was right.
Giacchetto's clients were more like friends than business associates.
Hollywood producer Bill Robinson, who witnessed the rise of Cassandra Group in young Hollywood,
says Cassandra was perceived almost like an exclusive club or a high school clique.
If you wanted to belong to the squad of stars like DiCaprio, Affleck, and Diaz, then investing
in Cassandra was the way to go.
The Cassandra club was your typical group of high school friends who bought their clothes
from the same stores, ate at the same places, and invested their money into the same fund.
Though Giacchetto was a nerd, he was a cool nerd.
Several Hollywood figures and businessmen invested in Giacchetto's fund.
One, in particular, was Mike Ovitz, the former Walt Disney World President and founder of
the Creative Artists Agency, or CAA.
Ovitz even called Giacchetto weekly, asking for money advice.
But none of Giacchetto's clients were as close to him as Leonardo DiCaprio.
Leo DiCaprio During the late 90s, Giacchetto owned a large
penthouse in SoHo, which served more as a castle that hosted the day-to-day operations
of Cassandra's trendy empire.
Just like in medieval times, important people would come to stay at Giacchetto's penthouse,
especially DiCaprio.
Young Leo spent months living in Giacchetto's penthouse.
Leo was new to Hollywood, and the confident Giacchetto gladly took the actor under his
wing.
If a producer wanted to discuss a job with Leo, they had to go through Giacchetto.
If you wanted to call Leo and have a quick chat, Giacchetto's house phone was the number
to call.
Other upstart celebrities stayed there as well, like Leo's friend Tobey MacGuire, and
singer Alanis Morrisette.
The culture there was productive and full of excitement.
Giacchetto proved to be supportive of his clients, especially Leo.
He would read scripts for Leo, attend parties with Leo, and help broker the actor's business
deals.
They were two peas in a SoHo pod.
When Leo received an invitation to attend the Oscars after starring in Titanic, the
young actor discarded the invite and chose to throw a party at Giacchetto's place instead.
Giacchetto fondly remembers the party as a youthful rebellion against the sellouts of
mainstream Hollywood.
They projected the award ceremony on the wall and watched as the film took home 11 Oscars.
That night was a big deal.
Titanic launched Leo's career.
As Leo rose up, so did Giacchetto, whose influence over Hollywood intensified after 1997.
Paradise The euphoria of his success led Giacchetto
to a company called Paradise.
In its pre-Giacchetto life, Paradise existed as a music and entertainment company that
produced music videos along with other entertainment content.
They made some bad business decisions, bad enough to nearly get them kicked off the NASDAQ
index, leading them straight to Giacchetto, who saw untapped potential in the failing
company.
Giacchetto breathed new life into Paradise.
But despite his good intentions, Giacchetto's breath proved to be more of a poison than
an anecdote.
After buying the downtrodden company in 1998, Giaccetto tried to sell shares of Paradise,
marketing the company as a huge growth opportunity.
He promised an epic and innovative new entertainment company.
Paradise's future plans included films, new music, and much more.
But it was through Cassandra Group that Giacchetto created the most hype.
Cassandra boasted a client base full of famous names.
To complement the famous names, Cassandra also boasted intelligent and respectable clients
like Ovitzo.
Giacchetto used these names to market the legitimacy of Paradise as an investment.
After all, if Leonardo DiCaprio bought 50,000 shares, why shouldn't you?
At $1 per share, the deal sounded pretty good.
Other Cassandra clients like Benicio Del Toro and Diaz bought shares.
After the initial offering, Giacchetto raised the price for new investors to $4.25 a share.
While this price may seem high for a company making hardly any money, people who are considered
intelligent bought in, like Ben Stiller and Leo's best friend, Tobey MacGuire.
But that wasn't enough.
Giacchetto announced he wanted to raise $8 million for Paradise.
He offered shares between $4 and $5 per share.
To build up the hype, Giacchetto doubled down on Leo's 50,000 share purchase.
However, DiCaprio's name wasn't enough, and Paradise failed to raise the $8 million, prompting
Giacchetto to buy remaining shares with his clients' money.
Several of his Cassandra clients reported seeing shares of Paradise in their accounts
with no memory of ordering them.
While the majority of his clients had bought in at $1 and sold off at $4, these particular
Cassandra clients wanted no part in Giaccetto's Paradise trade.
All in all, Giacchetto bought $2 million worth of shares without their consent.
This incident would be the first indication that Giacchetto was willing to cut corners
for his business deals.
It also became apparent, later on of course, that Giacchetto also cut corners in his personal
spending habits.
Wolf of Wall Street Giacchetto believed that his lifestyle and
personal influence on Leo led the star to join the cast of Martin Scorcese's capitalist
masterpiece, Wolf of Wall Street.
He believes teaching Leo about finance, business, and money led to the actor's interest in playing
Jordan Belfort, who Giacchetto swears he is nothing like.
Giacchetto claims he never tricked people like Belfort, but he certainly partied like
him.
Under the roof of his lavish penthouse, Giacchetto paints vivid pictures of benders involving
promiscuous games and copious amounts of alcohol consumption, among other substances.
Giacchetto's 90's escapades mirrored those of Jordan Belfort in Wolf of Wall Street.
Though it is unlikely Giacchetto's claim about him inspiring Leo's interest in the film is
true, his own life reflects the movie quite accurately, especially the part where they
both get caught.
Paradise Lost Giaccetto never wanted to steal money from
his clients.
His intentions, as the people he stole from would say, were genuine.
He wanted to make his clients money.
He felt like he needed to up the stakes, which is not always a good strategy when investing
other people's money.
As previously mentioned, Giacchetto rested on a conservative investment style for the
majority of his career.
Then he got lost in Paradise, literally.
The beginning of the end started when Giacchetto invested his clients' money in Paradise but
continued in the form of high-risk bonds and options.
Giacchetto's new strategy was a far cry from the blue-chip mantra he advertised in Cassandra's
early days.
This approach, on the other hand, was straight-up gambling.
Sure enough, disaster struck when one of his bond investments dropped 90%, resulting in
several investors losing nearly all their capital.
To pay them back, Giacchetto took money out of his other client's accounts and started
writing checks to the clients who suffered losses.
There was also a major cash flow issue.
Giacchetto was spending more money than Cassandra could earn.
Expensive vacations, financial compensations, and fancy dinners with Leo were all adding
up.
Investigators uncovered the truth about Cassandra, but it was too late.
The damage had been done.
Giacchetto misappropriated between 5 and 10 million dollars worth of his client's money
Between five and ten million dollars of a client, funds had been misappropriated to
cover Giacchetto's investment gambling losses.
When his clients found out, they abandoned the ship.
They could not jeopardize their careers by being closely associated with someone whose
wrists were being fitted for handcuffs.
Sure enough, on April 12th, 2000, Giacchetto was arrested by federal law enforcement.
From there, the former gen-x money manager found himself going to trial for stealing
his client's money.
He would eventually be found guilty in 2001 and sentenced to 57 months in prison.
After serving 5 years, Giacchetto returned to the business and did what he does best:
broker deals.
He helped assemble and facilitate a few multi-million dollar deals before being accused of committing
credit card fraud.
However, these charges were never proven.
Aftermath Towards the end of his life, Giacchetto's
benders became worse than ever.
Those who were close to him were not surprised.
They woke up to the news of his passing after a long night of drinking and partying.
According to them, Giacchetto was taking everything under the sun in addition to alcohol, leading
many to assume the former fund manager probably overdosed.
Leonardo Dicaprio never spoke a word or released a statement to acknowledge Giacchetto's death.
The man he'd once called "his little brother" was more like a distant 3rd cousin who lived
on the other side of the world.
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