From Triumphs to Tragedies: 17+ Dramatic Celebrity Investment Stories

Investment: The Compositor
Status: Failure

Back in the 1800’s, acclaimed author Mark Twain lost a fortune on a crackpot invention he thought would change the future. The so-called Paige Compositor was the brainchild of James W. Paige. The great, bulky piece of machinery was designed to print with a mechanical arm, but Paige couldn’t quite iron out the kinks. 

The Paige Compositor Scientific American/Wikimedia Commons

Twain invested an incredible $300,000 (the equivalent of $6 million today) in the idea, which sadly never came to fruition. Out of that sizeable amount, only two machines were made. One of them is on display at the Mark Twain House in Hartford, Connecticut. 

Investment: Bengal Tigers
Status: Filed for bankruptcy in 2003

Mike Tyson, the boxing legend known for his ferocity in the ring, faced a knock-out punch from his financial decisions. He’s famously known for his extravagant and poor investment choices, one of which included the purchase of rare Bengal tigers. 

Mike Tyson @kidplatano.tumblr.com/Pinterest

This reckless spending, along with a string of other high-price acquisitions and mounting legal problems, led to Tyson filing for bankruptcy in 2003. This experience accents the risks of irresponsible spending and serves as a stark admonition on the necessity of financial literacy, regardless of fame and fortune.

Investment: Sleek Audio’s headphone
Status: Never produced

In 2011, 50 Cent partnered with Sleek Audio, a Florida-based company, to launch a line of headphones. The rapper-turned-businessman invested a reported $2 million to start a line of “Sleek by 50” wireless headphones. 

50 Cent @Audífonos SMS México/Facebook

However, the partnership didn’t last long. Due to differences, they parted ways and the planned line of headphones was never produced. Unfortunately, this venture resulted in a significant loss for 50 Cent.

Investment: The Kardashian Kard
Status: Failed

The Kardashian sisters have been making money solidly for the last ten years thanks to their reality show – but not all of their businesses have been a hit. In 2010, Khloe, Kourtney, and Kim launched The Kardashian Kard, a prepaid credit card that made headlines for all the wrong reasons. 

©Christopher Polk/Getty Images

The card came under fire for charging users between $60-$100 just for activation. The crazily high fees didn’t hit the right note, especially as it was aimed at teenagers and kids. Less than a month after the launch, The Kardashian Kard ceased to be and the sisters moved on to pastures new. 

Investment: Dessert Beauty Edible Cosmetics 
Status: Defunct mid-2000s

Despite having a successful music career, Jessica Simpson has also made a significant impact in the fashion and cosmetics industry. One of her more unique business ventures was Dessert Beauty Edible Cosmetics – a line of lickable and kissable fragrances, body shimmers, and lip glosses.

Jessica Simpson @r/nostalgia/Reddit

Although the line was discontinued due to a lawsuit alleging that the formulas were not original, this venture was among the earliest examples of celebrities delving into peculiar niches in the cosmetics industry.

Investment: Dive! Theme Restaurant
Status: Defunct

A 300-seat eatery shaped like a submarine sounds like a surefire hit. But unfortunately, Steven Spielberg had a flop with this venture. Spielberg partnered up with Disney Studios Chairman Jeffrey Katzenberg to open the nautical-themed restaurant due to his love of diving. 

Steven Spielberg Martin Kraft/Wikimedia Commons

Spielberg might be a pro filmmaking game, but unfortunately, that success didn’t translate to the restaurant game. After about five years in operation, it was clear that the idea wasn’t going to stick. A second location was opened in Las Vegas, but it also failed to take off. 

Investment: Braselton, Georgia 
Status: $19 million* financial loss

Kim Basinger is one of America’s most famous faces but hasn’t always had it easy. In 1989, Kim banded together with a group of investors to buy 1,751 acres of privately owned land for a hefty $20 million. Together, they intended to turn the site into a tourist hotspot. That would’ve injected some much-needed cash into the small Georgia town.

Kim Basinger Roland Godefroy/Wikimedia Commons

The move, however, didn’t pan out. As development stalled, the following five years saw Kim’s investment dwindle in value considerably. The actress and her team finally sold off the undeveloped land for $1 million in 1994, taking a financial huge loss.

Investment: Flav’s Fried Chicken
Status: Opened and closed the same year

With a name like Flavor Flav, you’d think the rapper’s fried chicken venture would be a sensation. Sadly, the soul food restaurant Flav’s Fried Chicken ended up folding in 2011. The star opened the restaurant in Clinton, Iowa in January 2011. By April of the same year, it was closed. 

Flavor Flav @Associated Press/Youtube

Though Flav and his former business debated where the business essentially went wrong, most agree that there simply wasn’t enough money coming in to keep things going, making it a very fleeting Iowa hangout. 

Investment: Movie project
Status: Never made

Brendan Fraser, famed for his roles in blockbusters like “The Mummy,” funded an ill-fated movie project that ultimately never saw the light of day. Despite the significant investment made, the project ended up being stuck in development limbo due to unknown issues, possibly creative or financial. 

This, unfortunately, resulted in a substantial financial loss for Fraser. It stands as a poignant reminder of the inherent risk in film investments and the unpredictable nature of the movie business, even for seasoned actors like Fraser.

Brendan Fraser @ Nicki Swift/Youtube

Investment: Fashion line
Status: Failure

Kanye West’s self-funded 2012 women’s ready-to-wear line resulted in a hefty financial loss due to a lukewarm reception from fashion critics, plunging the rapper into debt. 

Kanye later invested millions of his personal fortune into Yeezy. However, initial presentations were met with tough criticism and underwhelming sales, pushing him reportedly $53 million into debt by 2016.

Kanye West @Trending Hollywood News/Pinterest

Investment: Palm Inc.
Status: Failure

Bono, the U2 frontman, ventured into the world of investment through his private equity firm, Elevation Partners. One notable investment was in Palm Inc., once a prominent player in the smartphone market. Elevation Partners reportedly invested over $400 million into Palm, betting on the company’s resurgence in the late 2000s.

However, this venture proved to be ill-fated. Despite the initial enthusiasm, Palm’s devices failed to ignite substantial consumer interest and struggled against dominant competitors like Apple’s iPhone. The result was Palm’s value declining drastically.

Bono @wsj/Youtube

Investment: An airplane
Status: Failure

Scottie Pippen, renowned former NBA player, encountered a significant financial setback when he invested in an airplane. Pippen spent a whopping $4 million on the plane with the intent of refurbishing it for personal use. 

Scottie Pippen @Juan Paolo David/sportskeeda.com

Unfortunately, the aircraft was never airworthy, leading to a significant financial loss. This misstep was further compounded when Pippen faced legal action. The bank eventually sued the former NBA player for not paying his debts.

Investment: Restaurant business and other ventures
Status: Failure

Estimating earnings over $300 million during his boxing career, four-time heavyweight champion, Evander Holyfield’s financial troubles arose largely from reckless spending, poor business investments, and detrimental financial advice. 

Evander Holyfield @ Fox Business/Youtube

Highlighted on CNBC’s Back in the Game, his failed ventures include a record label costing him $2.9 million and a restaurant business leading to a loss of $10.5 million. Further, products bearing his name, such as BBQ sauce, a kitchen grill, and a fire extinguisher, didn’t garner the expected popularity, adding to his financial woes. Holyfield’s story serves as a cautionary tale about the importance of disciplined spending and investment choices.

Investment: Various
Status: Unverified

Comedian and actor Chris Tucker faced significant financial challenges due to unsound investments and unpaid taxes, a path often tread by celebrities. Reportedly under poor guidance, Tucker made ill-advised investments contributing to his financial woes. 

Chris Tucker @Comedy Hype/Youtube

Additionally, substantial back taxes incurred a massive debt with the IRS. He was required to pay a shocking $14 million in 2014, and an additional $9.6 million.