Investing in a business to ensure you have a stable income seems like a wise decision — until it isn’t. Even celebrities who already have a ton of cash can’t be careless about choosing investments if they want to stay rich. From restaurants to clothing lines, the opportunities are plentiful, but it takes careful planning to avoid embarrassing business disasters.
Depending on your age, you probably remember these unforgettable celebrity business flops. Think you can guess who lost the most? Let’s take a look!
Britney Spears - Nyla Restaurant
When Britney Spears opened Nyla Restaurant in 2002, the buzz was real. She was in her prime years, and it seemed logical she would invest in a different type of business. Nyla was located in the Dylan Hotel in Manhattan, New York City.
The Kardashians - Kardashian Kard
The Kardashians are definitely business moguls, but not all their business ventures have been a success. Take the Kardashian Kard, for instance. In 2010, the Kardashians announced a controversial debut of a prepaid debit card featuring the sisters’ faces on the front. The business failed a month after its launch when the legality of certain fees raised concerns.
Kanye West - Pastelle Clothing Line
Yeezy has had plenty of fashion debuts during his career, and not all of them have been successful — or inspiring. Before his other fashion lines, there was Pastelle, the debut that never saw a debut. In 2006, Kanye planned to release his Pastelle clothing line in collaboration with Adidas.
Donald Trump - Trump Shuttle
Number 45 is a known businessman, but not many people know about his business failures. One of those epic failures was a very ambitious airline. Back in 1988, Donald Trump introduced his own branded airline shuttle. The luxury shuttle service was supposed to run between Washington D.C., Boston and New York.
Paris Hilton - Dollhouse Collection
It has been proven plenty of times that Paris Hilton knows what she’s doing when it comes to business. The Hilton heir has made quite a name for herself, but not every idea resulted in cash in the bank. In 2008, Paris Hilton for Dollhouse was released.
Oprah Winfrey - OWN
In 2011, Oprah was the talk of the town when she decided to operate a cable channel accessible to 80 million homes. The Oprah Winfrey Network (OWN) was an ambitious idea, with more than $500 million invested in the project. Unfortunately, her team failed from the beginning to understand what people responded to and how they watched cable channels. Low ratings and viewership hit the network hard.
Jennifer Lopez - Madre’s Restaurant
Celebrities have a thing for restaurants, but not all restaurants have a thing for celebs. Madre’s was inspired by J.Lo’s mom and grandmother’s cooking, and it started its bumpy journey in 2002 in Pasadena, California. In her own words, she described it as "a family restaurant with a little bit of sexiness to it."
Naomi Campbell & Friends - The Fashion Cafe
In her prime (mid-1990s), Naomi Campbell decided it was time to enjoy some passive income in the form of business ventures. In 1995, she became the face of a glamour-themed cafe chain called Fashion Café along with Christy Turlington, Elle Macpherson and Claudia Schiffer.
Steven Spielberg - Dive Restaurant
Steven Spielberg’s mind seems to overflow with amazing ideas, but Dive Restaurant wasn’t one of them. In 1994, he decided to open a nautical-themed restaurant in Beverly Hills. The place was filled with impressive dive-themed decor and even featured a simulated diving session experience.
Hulk Hogan - Pastamania Restaurant
When Hulkmania was at its peak, Hulk Hogan decided to introduce Minneapolis’ Mall of America to the ultimate Hulk eating experience. Who wouldn’t want to be strong and tough like Hulk Hogan, right? Although it definitely seemed like a solid business investment idea back in 1995, it didn’t work out in the end.
Donald Trump - Trump Mortgage
The Trump Shuttle wasn’t the only Trump business venture that failed to turn a profit back in the day. With his focus on real estate, it’s not surprising he tried to dip into the mortgage business. The success of this venture was very short lived.
Pete Wentz - Angels & Kings
In 2007, Pete Wentz, a popular member of Fall Out Boy, and several other musicians decided it was time to open a nightclub. Wentz claimed he just wanted a place for him and his friends to hang out. Later, the club launched in several other locations, including Chicago.
Jim McMahon - McMahon's Steakhouse
Ex-Chicago Bear Jim McMahon made a name for himself in the NFL in the ‘90s and also thought he could make a name for himself by investing in a restaurant — a steakhouse in Chicago. Unfortunately, McMahon got into business with some pretty questionable characters whose reputation wasn’t pristine among those in the bank loan world.
Eva Longoria - Beso Restaurant and Nightclub
Eva Longoria is no stranger to the culinary scene — remember her role as a guest judge on season 4 of MasterChef? In 2008, she backed a Los Angeles restaurant called Beso. The place was a hot spot for quite some time before closing its doors in 2011 amidst a ton of drama.
Jay-Z - J-Hotels
The world’s first billionaire rapper is no stranger to successful business ventures, but the idea that "the sky is the limit" definitely doesn’t apply here. Jay-Z definitely reached a limit with his investment in J-Hotels. The luxury hotel was supposed to open in Manhattan’s Chelsea area, but lack of funding and a recession halted the construction.
Natalie Portman - Té Casan
Let’s take a break from restaurants and hotels for a while and go to 2008, which really seemed to be a prime time for celebrity business investments and hotels. Natalie Portman was ahead of her time when she collaborated with Té Casan to create a vegan shoe line.
Jermaine Dupri - Café Dupri
Jermaine Dupri rose to popularity in the ‘90s. From forming the iconic Kris Kross to producing music for all your favorite celebrities, Dupri was definitely at the top of his game. In 2005, he decided to try other business ventures and invested in a large café in Atlanta that seated 105 guests.
Beyonce - House of Deréon
That’s right — Queen B has experienced many failures along with her success. Sounding like a house out of Game of Thrones, House of Deréon was a fashion line Beyonce collaborated with her mother, Tina Knowles, to create in 2006. The name paid tribute to Beyonce’s maternal grandmother.
Lily Allen - Lucy in Disguise
Lily Allen also tried to dabble in the fashion world. The eccentric singer is known for her fashion sense, so it seemed only fair to see if the rest of the world (or at least London) would catch on to her look. She opened Lucy in Disguise, a vintage clothing store, with her sister in 2010.
Neil Young - PonoPlayer
PonoPlayer was a fairly modern business venture launched by Neil Young in 2014. It was actually successfully crowdfunded via the popular platform Kickstarter, where it raised $6.2 million. The device was advertised as a modern-day iPod with hi-resolution music service, but it was criticized for its poor design and high price tag ($400).
Sylvester Stallone, Arnold Schwarzenegger & Bruce Willis - Planet Hollywood
Planet Hollywood was a ‘90s sensation and boasted more than 100 locations. Stallone, Schwarzenegger and Willis were its investors and the faces promoting the brand. The initial hype of eating among popular movie props attracted endorsements from some of the biggest Hollywood names, but it wasn’t all sunshine and rainbows.
Kevin Costner - The Clubhouse
Themed restaurants were extremely popular investments for celebrities, and Kevin Costner was in on the idea too. In 1997, he dabbled in the food industry in an attempt to make more money, of course. The theme of The Clubhouse was golf, and unlike many other celebrity restaurants, it managed to last a surprisingly long time.
Curt Schilling - 38 Studios
A unique business venture for its time, 38 Studios was the brainchild of Curt Schilling, who had a different vision than most sports celebrities. The former Red Sox pitcher wanted to try something new, so he launched a video game business in 2006. Unfortunately, game development takes years, and that was hard to sell to investors.
Pharrell Williams - Qream Liqueur
Pharrell Williams always had big visions and a good ear for music, but in 2011, the popular producer ventured into the world of liqueur with much less impressive results. He worked with Diageo to launch Qream strawberry and peach liqueurs, specifically marketed to women.
Flavor Flav - Flavor Flav's Chicken & Ribs
Who doesn’t know Flavor Flav? In 2011, the popular rapper decided to combine his love of fast food with business by opening a restaurant in Clinton, Iowa. Although it sounds yummy, the business really didn’t last that long. In fact, it’s one of the shortest examples of business failure on the list — three months.
50 Cent - Magic Stick Condom
Magic Stick was 50 Cent’s attempt at a unique business venture — in condoms. Yes, you read that right. In 2008, the rapper created a line of condoms, but he apparently failed to understand the reason behind condoms in the first place. His company’s condoms were laced with chemicals designed to increase the wearer’s sexual performance.
Blake Lively - Preserve
Blake Lively is known for the awesome sense of humor she shares with her even more awesome husband. In 2014, she decided to launch a lifestyle website. The timing was perfect, as celebrity lifestyle websites were at their peak, but Lively wasn’t a big enough lifestyle figure to attract much interest.
Heidi Montag - Heidiwood
Welcome to Heidiwood, a fashion line that failed to connect with its customers and make sufficient profit. It belonged to Heidi Montag, a popular reality television character who wanted to be known for more than just her dramatic TV roles. She launched Heidiwood in 2007 in collaboration with Anchor Blue Retail.
Nicky Hilton - Nicky O Hotels
Paris Hilton wasn’t the only Hilton making money moves. Back in the day, her sister Nicky Hilton wanted to stay true to her family legacy and open a hotel chain of her own. Nicky O Hotels was a premier luxury hotel brand, set to launch in Miami and later Chicago.
Jennifer Lopez - Sweetface
Making the list again, J.Lo’s high-end Sweetface clothing line was yet another failure in the celebrity fashion world. Attempting to combine urban streetwear with modern fashion, the line failed to deliver anything unique that couldn’t be found for a cheaper price in a store down the street — according to shoppers’ feedback.