29+ Celebrity Business Ventures That Didn’t Go As Planned

the tea

| LAST UPDATE 06/22/2023

By Smart Carblood

It almost seems like every day, there's another celebrity announcing their latest business venture. While many of these attempts have turned stars into billionaire entrepreneurs, others haven't worked out as well...

Rihanna: Fenty Clothing

Believe it or not, not everything that Rihanna touches turns into Diamonds. While Fenty Beauty and Fenty Skin have found great success, the luxury Fenty Clothing line was not met with the same fate.

Rihanna, Fenty, Clothing LineRihanna, Fenty, Clothing Line
Dimitrios Kambouris via Getty Images for Bergdorf Goodman

After just two years in operation, the singer was forced to shut down the brand, announcing it would return "pending better conditions." Ultimately, this was speculated to mean that during the Covid-19 pandemic, people were more interested in saving their pennies than splashing out on the luxury items they offered.

Natalie Portman: Casan Footwear

Although vegan products are now all the rage, it appears Natalie Portman was ahead of the times with her vegan footwear range in 2008. In collaboration with Te Casan, the actress launched 'the Natalie Portman Collection,' a shoe line that harmed no animals for its production.

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Astrid Stawiarz via Getty Images

Released in January 2008, the shoes were viewed by many as overpriced, especially with their underlying cause seemingly less understood. With a pair of flats priced at $185, the company struggled to get the shoes off the shelves. After a massive sale in November that year, the business shut down entirely just a month later.

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Kanye West: Pastelle

Kanye West may want us all to believe that Yeezy was a breezy overnight success, but that's not the honest truth. Before the brand turned the rapper into a billionaire designer, he was working hard to make Pastelle happen. To say this brand differed in comparison to Yeezy would be an understatement...

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Kevin Mazur / Contributor via Getty Images

In 2009, pictures were released of the Pastelle fashion line, promising to be the streetwear brand of our dreams. Two days later, it was pretty much over. It was highly speculated that Kanye's infamous Taylor Swift VMA moment, which took place shortly before the announcement, was responsible for the brand's premature downfall.

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Jennifer Lopez: Madres Restaurant

In yet another reminder that J.Lo is just Jenny from the Block, the singer opened a Latin food restaurant in 2002, selling all the food she had grown up eating. In celebration of her Puerto Rican heritage, she sold empanadas, ceviche, ropa vieja and arroz con pollo. The prices, however, were not as relatable.

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Michael Caulfield/WireImage via Getty Images

With dishes priced between $30 and $50, critics were unimpressed by the food's quality and taste, deeming it unworthy of its hefty price tag. Although the institution remained open for longer than expected, six years later, it shut down with no explanation. "Madres will be closed until further notice," the sign on the door read.

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Mandy Moore: Mblem

Mandy Moore has never failed to make us cry with her acting performances. However, after the failure of her clothing business, Mblem, it's likely she was the one shedding a tear. In 2005, at the age of just 21, the actress launched her youthful clothing brand, which was sold in stores across the country.

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Michael Buckner / Staff via Getty Images

Just three years later, the line was discontinued, as Moore explained she wanted to put all her efforts into her music career. An interview with Women's Wear Daily in 2009 suggested that there was more to the decision, as she hinted at a lack of creative control in the process.

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Nicky Hilton: Nicky-O Hotels

As a descendant of the Hilton Hotel chain founder, Nicky Hilton's venture to establish her own hotel line, Nicky-O-Hotels, seemed like a sure thing. However, this quickly proved not to be the case. The 94-room hotel on Miami's Ocean Drive, designed by Roberto Cavalli, was set for a 2007 opening date.

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Gustavo Caballero / Contributor via Getty Images

Taking advantage of the 2007 Miami Super Bowl, the hotel sold a $10,000 per night Super Bowl package. However, the doors of the hotel were never opened to the public. It filed for bankruptcy that same year, and Hilton was later sued by her developer for failing to promote the hotel as promised.

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Curt Schilling: 38 Studios

An avid fan of video games, Curt Schilling established a video game company titled 38 Studios in 2006. Three years later, the Red Sox pitcher retired from baseball to give the company his full attention. This decision proved worthwhile when he received a $75 million loan from Rhode Island to relocate there from Massachusetts.

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Boston Globe / Contributor via Getty Images

Despite producing one relatively successful game named "Kingdoms of Amalur: Reckoning," sales were not enough for the company to break even. Now unable to make repayments on their large loan, Schilling was forced to admit that the company was suffering from significant financial issues. In 2012, it was game over.

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Vince McMahon: XFL

While most of us have heard of the NFL, the XFL is its lesser-known little brother. According to its chairman and CEO, Vince McMahon, it was to be the next big thing in football... but this did not prove to be the case. It had one season in 2001, and it was a whirlwind from start to finish.

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Tom Hauck/Allsport via Getty Images

Heavily criticized for its poor organization, weak players, and lack of actual gameplay, the league's closure surprised very few. Convinced of his vision, McMahon attempted to bring it back in 2020, but the Covid-19 pandemic stumped this. Perhaps, third-times a charm as Dwayne "The Rock" Johnson plans to revive it in 2022.

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Heidi Montag: Heidiwood

She may have made it big in the reality television world with her time on The Hills, but Heidi Montag's attempt to find equal success in the fashion industry proved less fruitful. Her inexpensive clothing line, Heidiwood, was sold in Anchor Blue stores across the country and was marketed primarily to teenage girls.

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Jason Merritt/FilmMagic via Getty Images

The line, however, was quite unsuccessful, with critics criticizing the brand for being flimsy, thin, and "unwearable." The Cut described the clothes as "the complete opposite of flattering." Following a year of weak sale numbers, Anchor Blue announced they were severing ties with Montag.

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Jay-Z: J Hotels

The 2008 financial recession was hard on everyone - and even celebrities like Jay-Z were not immune to its impacts. In 2008, the Roc Nation icon launched his company, J Hotels, and announced his plans to build a luxury hotel in the Manhattan neighborhood of Chelsea. However, it never came to be.

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John Parra via Getty Images

As a result of the recession, the real-estate business took a fall. A lack of funding caused construction delays, and ultimately Jay Z and his partners were unable to pay back their loan. They ended up suing the investment firm that lent them the money, and the property was returned to its original lenders.

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Debbie Reynolds: Hollywood Hotel

When Debbie Renolds purchased the Paddlewheel Hotel & Casino in Vegas, she had big dreams of converting it into The Debbie Reynolds' Hollywood Hotel. Not just a place for visitors to stay, the venue would be a Hollywood memorabilia museum and casino.

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Lennox Mclendon/AP via Shutterstock

Although the idea seemed promising, she made an apparent error by partnering up with Jackpot Enterprises for the casino. By not owning and controlling the gaming venue, Reynolds failed to see any profits. Finally, in 1997, she gave up on her dream, filing for bankruptcy on behalf of herself and the hotel.

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Flavor Flav: Flav's Fried Chicken

Flavor Flav loves fried chicken and has therefore attempted to make money off the food numerous times throughout his career. The rapper's first venture was Flav's Fried Chicken, which he established in 2011 in Clinton, Iowa. Sadly, financial issues forced its closure just four months later.

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Ethan Miller via Getty Images

Not willing to give up on his dream, he opened Flavor Flav's House of Flavor in Las Vegas in 2012. Outlasting its predecessor by just two months, the two-and-a-half-star-rated restaurant shut in September 2012. He gave it one last shot in 2013 with Flavor Flav's Chicken & Ribs in Michigan, which eventually succumbed to debt.

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Pharrell Williams: Qream with a Q

In 2011, Pharell Williams took his focus away from music producing and singing and attempted to break into the alcohol industry. Capitalizing on what he believed to be an untapped market, Williams targeted his liquor, Qream with a Q, specifically at women. "We're bringing indulgence back to the ladies," he announced at the launch.

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Johnny Nunez/WireImage via Getty Images

It seemed the gap in the market may have been there for a reason, as just a year later, the product was discontinued due to poor sales. By 2013, Pharrell had sued his marketing partner Diageo for improperly marketing the product as a party drink, not a high-end liquor, seemingly causing its downfall.

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Beyoncé: House Of Deréon

In partnership with her mother, Beyoncé set out to create House of Deréon, a fashion line named after her grandmother, Agnéz Deréon. In 2006, the brand was officially launched, and a few years later, Queen B expanded the family business, teaming up with her sister, Solange, to create a juniors collection.

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Eamonn McCormack via Getty Images

The over-the-top clothes, however, did not match Beyoncé's classy aesthetic. According to Vice, "it somehow was too gaudy for 2000s and early 2010s America, when gaudiness and tackiness were the name of the game." After the juniors line was discontinued in 2012, the rest of the business followed suit in the years after.

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Naomi Campbell, Elle Macpherson & Claudia Schiffer: Fashion Café

This list has included a wide range of themed restaurants, from pasta to submarines. This celebrity-restaurant business, named Fashion Café, boasted the theme of 'models.' For anyone wondering how this is a theme exactly, we're not too sure anyone knew the answer to this question - even the models themselves.

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Images Press / Contributor via Getty Images

In 1995, the first branch opened in New York City, and eight more locations soon followed. It seemed unlikely to flop with 'it' models Naomi Campbell, Elle Macpherson, and Claudia Schiffer as the faces. But, by 2000, all the branches had been shut down, with its founding Buti brothers indicted for fraud and money laundering.

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Richard Branson: Virgin Cola

At first glance, this may look like a regular Coke can, but a closer look will reveal it's actually Virgin Cola. The British billionaire founder of the Virgin group attempted to take on one of the biggest companies in the world in 1994 with his soda drink. After much success in the UK, he took the product to the US market.

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Times Newspapers via Shutterstock

Despite a promising start, Branson soon learned a harsh business lesson, as Coke used its power over retailers to drive the new drink out of business. "If you are taking on a business far larger than yours, you have to be so much better than them," he reflected in his blog. "There wasn't that much difference in the product."

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Shaquille O'Neill & Kung Fu: Shaq Fu

Shaq Fu was a video game released in 1994 and combined basketball player Shaquille O'Neil and the Chinese martial art Kung Fu. Sadly, it was met by staggering amounts of hate and criticism, as was described by IGN as one "of those rare gems, a game so universally reviled that everybody can sit down and agree over its awfulness."

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Focus on Sport via Getty Images

In an unpredicted development, a sequel of the game was released in 2018 titled "Shaq Fu: A Legend Reborn." Sadly, it suffered a similar fate to its predecessor and was rated a three out of ten by PlayStation Lifestyle. Alongside the rating, they described it as "dull and soulless."

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Britney Spears: Nyla

Oops, a celebrity has done it again! This time, it was Britney Spears. She opened Nyla in 2002, a cajun-themed restaurant located in New York City's Dylan Hotel. The pop singer was hoping to capitalize on her then-high levels of fame and stardom with this entrepreneurial venture.

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Bill Davila / Contributor via Getty Images

The restaurant was reportedly $350,000 over budget from the start and was unable to pick up the slack over time. In a desperate attempt to save it, the cuisine was changed to Italian, but it failed to make a difference. Six months after opening, Britney threw in the towel by removing her name from the institution.

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Eva Longoria: Beso

Not one to give up without a fight, Eva Longoria set up not one but two restaurants. It all started in 2008 when the Desperate Housewives star teamed up with celebrity chef Todd English to create Beso. The Latin-style steakhouse was instantly popular and found quick success. A year later, she opened another branch in Vegas.

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Michael Bezjian / Contributor via Getty Images

Unfortunately, the Vegas venue lost money rapidly and filed for bankruptcy in January 2011. From there, the bad luck continued. The original Hollywood restaurant suffered some bad press in 2016 while closed for renovations. It consequently failed to reopen till 2017, with a new name... and without Longoria.

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Pete Wentz: Angels & Kings

Fall out Boy's lead singer fell out of luck when he established his nightclub, Angels and Kings, in 2007. With the goal of having a place "where [he and his friends] can hang out and be ourselves," the New York City venue was advertised as a relaxed venue with very few rules.

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Theo Wargo / Staff via Getty Images

As it turns out, people apparently like rules and order, and the club's Yelp reviews reflected this fact. With a two-and-a-half star rating, the crowds weren't exactly overwhelming. Three other branches had been opened in Chicago, Hollywood, and Barcelona - but by 2012 they had all been shut for good.

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Lindsay Lohan: Lohan Beach Club

After shooting to fame as a child actress and later losing her way with substance struggles, Lindsay Lohan attempted to get back on track by becoming a businesswoman. The star opened a beach club in Mykonos, Greece, in 2018 and additionally invited MTV to make a reality show about the process.

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Instagram via @lohanbeachclub

While a seemingly genius idea on paper, linking the projects led to their mutual collapse. After Lohan's Beach House club failed to attract the clientele it needed and shut down thirteen months later, the show suffered a similar fate and was canceled after just one season.

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Blake Lively: Preserve

We have Goop, we have Poosh, and once upon a time, we had Preserve. In 2014, Blake Lively attempted to make it big in the lifestyle market with her "part magazine, part e-commerce hub, part philanthropic endeavor and – above all– a place to showcase the power of imagination, ingenuity, quality, and (simply put) people."

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Robert Kamau / Contributor via Getty Images

With this description, the people, and seemingly Blake herself, were unclear on the site's true purpose, and it failed to find its place. The actress announced she would be shutting down the site and explained it was because Preserve was "not making a difference in people's lives, whether superficially or in a meaningful way."

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Steven Spielberg: Dive!

He may be one of the greatest directors of our time, but Steven Spielberg's ability to manage a restaurant was not quite as praiseworthy. Along with the CEO of Dreamwork, Jeffrey Katzenberg, the pair used their creative minds to create a submarine-themed restaurant that was shaped as so. In 1994, it opened in Los Angeles.

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Marc Piasecki/GC Images via Getty Images

It was the ultimate thematic experience. Submarine sandwiches were sold, and guests experienced a 'dive' every thirty minutes with sirens, blacked-out windows, and groaning noises. However, the $7 million restaurant was gimmicky, and customers didn't usually return. After failing to make a profit, it shut down in 1999.

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Neil Young: Pono Music

In 2011, Neil Young established PonoMusic to "create a movement to bring back the soul of music, and to revitalize the vinyl experience in the digital realm." The PonoMusicStore was set to sell "higher quality" music that could be played on a $400 PonoPlayer. Unfortunately, the science didn't match up with the claims.

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starzfly/Bauer-Griffin / Contributor via Getty Images

During a blind audio test, the participants failed to differentiate between the music coming from the player and a low-quality mp3 file. In 2017, Young announced the closure of PonoPlayer, sighting high costs as the cause. The rise of music streaming services is likely to have also contributed to its failure.

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Hulk Hogan: Pastamania

Hulk Hogan is yet another celebrity who hoped to bring in the bucks with a restaurant business. Named Pastamania and located in the Mall of America outside Minneapolis, the wrestling legend's dining venue served pasta-based dishes named 'Hulk-U's' and 'Hulk-a-Roos.'

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Raymond Hall / Contributor via Getty Images

Hogan used his time in the ring to advertise the fast-food restaurant, but it was not enough to keep its doors open. While certainly a novelty, it seemed to be no more than that, and customers grew tired of the buzz. In 1995, which is the same year it opened, the restaurant shut down.

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Lenny Dykstra: The Player's Club

One of the more unique entries on this list, baseball star Lenny Dykstra attempted to branch out into the print media business with his magazine, The Player's Club. It advertised itself as a lifestyle guide for pro athletes, with suggestions on how they should spend and invest their earnings.

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Amy Sussman / Stringer via Getty Images

Soon enough, it became clear that the company was not qualified to be dishing out financial advice as they struggled to make any money. Dykstra stopped paying his rent, employees, and publishing house and finally declared bankruptcy just a year after the business opened. Two years later, he was arrested for bankruptcy fraud.

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Kim Kardashian: Va-Va-Va-Nilla

It seems that everything Kim Kardashian comes up with is a million-dollar idea, but it hasn't always been this way. Back in 2010, she attempted to get a taste of the baking industry. In partnership with Famous Cupcakes, the reality star sold the Va-Va-Va-Nilla Cupcake Mix.

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Toby Canham / Contributor via Getty Images

The $13 sweet product included vanilla cake mix, cupcake liners, a frosting recipe, and pink sugar crystals. While nowadays she could probably sell them out in minutes and crash the internet while doing so, her name was apparently less powerful back then. Within a few months, the product and the brand were nowhere to be seen.

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Kim Basinger: Braseltown, Georgia

Kim Basinger was channeling 'go big or go home' energy with her business venture. In 1989, the actress purchased the entire town of Braselton, Georgia, in exchange for $20 million. What did she plan to do with the 1750-acre town? Well, she wanted to turn it into a tourist attraction with movie and recording studios.

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Alessio Botticelli/GC Images via Getty Images

However, Basinger was never able to make it happen. It is believed that apart from some torn-down buildings, little progress was made. It turns out that the project would cost a lot more than expected, and after some financial difficulties, she filed for bankruptcy in 1993 and made a loss selling the town for $1 million.

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Scott Disick: Ryu

His famous almost sister-in-law, Kim Kardashian, holds the record for one of the shortest celebrity marriages in history at just 72 days. However, Scott Disick has a place on the leadership board for one of the shortest-lived celebrity-owned restaurants, with 191 days.

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Gotham / Contributor via Getty Images

The reality star's NYC restaurant, RYU, was established in 2012, with all the Kardashians sisters at the grand opening. Critics were unimpressed by the Japanese food and overall dining experience, and within six months, the restaurant shut its doors permanently. It's believed Disick abandoned the project sometime before this.

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Kardashians: Kardashian Kard

Oh, the Kardashians. Nowadays, they're selling us everything from underwear to tequila, and let's be honest; we're practically buying it all. However, this hasn't always been the case. Back in 2010, the older sisters released a prepaid debit card, and just 250 people purchased it.

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Jun Sato / Contributor via Getty Images

The Kardashian Kard included a $99.95 purchase fee, a $7.95 monthly fee, a $6 closing fee, and a $2 charge for paying a bill. According to the Connecticut Attorney General Richard Blumenthal, the card was taking advantage of vulnerable young adults who wouldn't understand the costs involved. Within a month, it was over.

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