Celebrity Business Disasters (Including Donald Trump!) You Can’t Forget

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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.

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Her departure from the business occurred in the same year after she butted heads with the management, who claimed she was responsible for the restaurant’s debt and other financial issues. Fun fact: The restaurant was supposed to be called “Pinky,” which was the nickname Justin Timberlake gave Britney when they were dating.

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.

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An attorney claimed the high fees were unfair and unethical, particularly for the Kardashians’ largely young adult fanbase. Many reputable websites took note of the “Kardashian Kard ripoff,” which prompted the Kardashian family’s attorney to take immediate action and terminate the business to protect their reputation.

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.

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In short, a lot of drama happened, and according to reports, the investors didn’t want to invest a sufficient amount of money to get the business off the ground. Kanye himself said you need to invest at least $100 million when you’re making a new brand, and it clearly didn’t happen.

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.

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Red carpets, gold and other luxury elements cost Trump $1 million per aircraft. Three months after the launch, one of his planes almost crashed. The near miss, rising fuel prices and a bank loan of $380 million made Trump decide it was time to leave his aviation dreams behind and try something else.

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.

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It was a collaboration between Hilton and the popular clothing label, and absolutely everyone was buzzing about it. The collection basically had Paris’ face and name on almost every article of clothing. Unfortunately, the glory didn’t last long, and Paris moved on to other business ventures that garnered more appeal.

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.

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OWN was arguably Oprah’s biggest failure, but unlike other celebrities on our list, Oprah still hasn’t completely given up on her business venture. Who knows? Maybe OWN is finally on track to pull itself out of some dark days.

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.”

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It lasted about six years before mysteriously closing its doors in 2008. The Latin American restaurant featured some of the culture’s most typical dishes, but J.Lo’s name wasn’t enough to entice the public. No official reason was ever given for the decision to close it down, but the assumption is poor performance.

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.

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It had a solid start and good buzz, but the novelty eventually faded, and it failed to make the necessary profit to stay open. To top it all off, the business partners got involved in a money laundering scandal, making it clear that it was better for this cafe chain to close its doors for good.

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.

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That still wasn’t enough to charm the demanding Beverly Hills crowd, and the novelty of it started to wear off, resulting in dismal merchandise sales, which were a huge selling point for the business. In 1999, the restaurant officially shut its doors and became a learning lesson for what not to do in the niche of themed restaurants.

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.

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The menu wasn’t that different from your standard pasta restaurant menu, apart from the fact that it was branded by everyone’s favorite wrestling guy. The restaurant shut its doors almost a year later, allowing the Pastamania name to be used by a fast food chain from Singapore.

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.

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Most of the Trump Mortgage failure came down to poor timing, as the 2006 recession struck, and the mortgage lending industry began to crumble with the market crash. Everything was questioned, including the CEO’s background. In 2007, Trump Mortgage officially closed down after failing to thrive in the struggling market.

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.

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The hype of the celebrity-owned nightclub died down after it was reported that the New York location got caught serving alcohol to minors and had to shut down in 2012. A few years later, they also closed the Chicago location — and that was the end of the Fall Out Boy nightclub.

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.

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The restaurant was first called Chicago Stadium, but the owners of the Chicago Stadium quickly sued McMahon and his other business partners. According to reports, the restaurant participated in some shady business practices, and McMahon had to distance himself from it.

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.

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The business filed for bankruptcy in order to restructure $5.7 million worth of debt, and Longoria has reportedly been involved in several lawsuits. Beso later relaunched under new ownership (without Longoria) and with a new name, Viva Hollywood, but that restaurant eventually closed as well.

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.

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The recession going on at the time basically made it harder to get the funding needed, and the whole business project was put on hold in 2008. It looks like it never resumed, probably because Jay-Z became interested in plenty of other appealing ventures.

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.

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As a long-term vegan, she felt the need to invest in something she believes in, and she felt a shoe line was definitely the way to go. Unfortunately, the high price of the shoes didn’t exactly appeal to consumers — not even diehard vegans — and the shoe line’s website disappeared by the end of 2008.

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.

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The menu consisted of high-quality dishes that were also considered healthy. Although it seemed like a decent idea and the cafe had big expansion dreams, the success didn’t last. Three years later, Cafe Dupri had to close its doors after struggling to make enough profit.

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.

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The style mixed the influences of hip hop with high fashion, and although it seemed like it was taking off at first, it was ultimately criticized for its high prices. In 2008, the line also came under fire for its ad with little girls wearing full makeup and high heels. The star discontinued the line in 2012 without formal notice.

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.

Photo Courtesy: Justin Higuchi/Wikimedia Commons & Lucy in Disguise Facebook Page

The store’s location was one of the reasons for its failure — London’s Covent Garden. High real estate prices forced the company to move to a somewhat cheaper property in Soho, but it wasn’t enough to save the business, and it ceased operations in 2012.

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).

Photo Courtesy: Mark Estabrook/Wikimedia Commons & PonoPlayer Amazon Product Page

Three years later, Neil Young ceased operations and closed the PonoMusic store, which sold downloadable music. The reason? Record companies were charging too much for hi-res music formats, and the business couldn’t make a profit, despite the steep price of PonoPlayer and its initial funds.

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.

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The business filed for bankruptcy twice and reduced its number of restaurants to less than a dozen to ensure it could financially sustain itself and make a profit. This prompted investors like Arnold Schwarzenegger to move on and cut ties with the business. Planet Hollywood is still around but with much less hype and fewer restaurants.

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.

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Based in Costa Mesa, California, it featured the exclusive look and style of a golf clubhouse that was open to the public. Ironically, it opened right across from Planet Hollywood, which was closing at the time. The business began to fail in 2007.

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.

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The company released an action role-playing game called Kingdoms of Amalur: Reckoning. Unfortunately for Schilling, the gaming company declared bankruptcy in 2012 after only releasing a single game. Despite the business’ failure, the game was pretty well received by the gaming community.

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.

Photo Courtesy: Googie Man/Wikimedia Commons & Qream Liqueur/Drizly

Williams blamed Diageo for insufficient marketing efforts to launch the liqueur, and he sued the company in 2013 after it appeared to abandon the deal before the contract was over. The drink wasn’t marketed effectively, and the Qream dream died with minimal fanfare.

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.

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The restaurant closed its doors due to a fallout between Flavor Flav and his business partner, Nick Cimino. The two clashed over operations and money management, leading Flav to decide that fast food really wasn’t for him after all — at least when it came to running a business.

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.

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The rapper was asked about his failed business venture, and he said, “It just didn’t work out because I wanted things in it that wouldn’t work.” P.S.: “Candy Shop” lyrics were written way before the Magic Stick line was launched.

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.

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Celebrity product endorsements are often too expensive for the general public and can also feel fake, which raises concerns when it comes to trust. The website was abandoned about a year later, and her lifestyle venture was never mentioned again. That’s okay, she’s still owning the Instagram game.

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.

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Although the line looked promising, customers didn’t really care for the overpriced items, and her contract wasn’t renewed the following year. She returned to reality TV and is still a prominent figure in the celebrity gossip world, so she bounced back financially from the failed venture.

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.

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Hilton planned to work with Roberto Cavalli to design a luxurious penthouse suite for the Miami location. Her ambition was to combine the world of entertainment with luxury and design. However, the project failed to see the light of day after a lawsuit against Hilton highlighted an alleged breach of contract.

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.

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Customers complained about high prices as well as the quality of the clothes. Negative feedback and poor sales forced Kohl’s to completely stop the line’s production in 2009. Fun fact: Sweetface was J.Lo’s nickname, given to her by her old manager.