Some celebrity investors are making a fortune from their business interests, which range from tech start-ups to big-name companies. But not every star investor has the Midas touch. Click or scroll through to see the showbiz world's most successful investors, the famous people who have had mixed success in the investing game, and some of the worst celebrity investing fails of all time. All dollar amounts in US dollars.

Ashton Kutcher is hands-down the most prolific celebrity investor. Together with his investing partner Guy Oseary, who also manages Madonna, Kutcher has invested in scores of start-ups. The actor's standout investments include a $500,000 (£364k) stake in Uber that is now worth tens of millions of dollars, as well as significant interests in Airbnb, Spotify, Soundcloud and Shazam.

Giving Kutcher and Oseary a run for their money, Jared Leto is up there with the savviest celebrity investors. The Oscar-winning actor has bankrolled more than 50 tech start-ups, and had the foresight to invest in Uber, Airbnb and smart home firm Nest in its early days. In fact, Leto is so good at the tech investing game, he even serves as an adviser for a number of start-ups.

When it comes to tech angel investing, NBA All Star Carmelo Anthony is catching up fast with Ashton Kutcher and Jared Leto. The basketball player founded investment firm Melo7 Tech Partners with partner Stuart Goldfard in 2013, and has since invested in more than 28 start-ups and made numerous acquisitions, including women's online fashion firm PureWow and voice messaging app Cord. In February 2019, the sports star invested in the sports video platform Overtime as part of a $23 million (£18m) round of investment.

Instead of spreading his money around, Dr. Dre homed in on headphones, investing his cash in the Beats line back in 2008. A major success from the get-go, the hip-hop mogul cashed in to the tune of $500 million (£364m) when Apple bought Beats for $3 billion (£2.18 billion) in 2014, making Dre one of the richest people in the showbiz world, with a net worth of $800 million (£623m) in 2019 according to Forbes. 

Supermodel, talk show host, producer, author and now super-successful investor, Tyra Banks seems to excel at everything she does. The Inglewood-born star cleaned up in 2015 when Locket, the lockscreen app she invested in back in 2013, was acquired by rival firm Wish, and Banks' other investments, which include a stake in career advice site The Muse, are riding high and generating big gains.

Ryan Seacrest has raked in tonnes of cash from his high-profile radio and TV gigs, but the presenter could always stick to investing if his showbiz career hits the doldrums. Over the years, Seacrest has invested wisely in a variety of both established and up-and-coming tech companies, from Pinterest to media start-up ATTN.

Retired basketball star Magic Johnson set up his eponymous investment company Magic Johnson Enterprises in the 1990s and has made hundreds of millions of dollars over the years from his interests, which range from Starbucks – Johnson once owned 105 franchises – to  stakes in the Los Angeles Lakers and fast food chains including Burger King and T.G.I. Fridays. He has sold most of these since, including his 4% stake in the Lakers which netted him an estimated $27 million (£21m) when he sold it in 2010. Two years later he invested $50 million (£39m) in the Los Angeles Dodgers, which gave him a 2.3% share.

Blessed with a knack for seeking out profitable ventures, Jessica Alba co-founded ethical skin care firm The Honest Co. in 2011 partly with her own cash, giving her 20% equity. Soon the company was valued at $1 billion (£777m) in 2016. However, it wasn't to last, and the business ran into difficulty as it faced multiple lawsuits over mislabelled ingredients and faulty products. This led to the business having to pay out millions. But a new CEO in 2017, and investment to the tune of $200 million (£155m) from LMVH in 2018, has seen The Honest Co. start to bounce back, likely to record sales of $350 million (£272m) in 2020. Alba has also invested in mindfulness app Headspace, Honor senior home care and office cleaning service Managed by Q, three businesses that are thriving right now.

Rapper Nas is one of the showbiz world's most active investors. Since 2007, the switched-on New Yorker has invested in over 40 tech companies along with his partner and manager Anthony Saleh, including Dropbox, Coinbase and the fast-growing Robinhood no-fee stock trading app, which boasts 13 million subscribers and was valued at $8.3 billion (£6.5bn) at its latest funding round in 2020.

Nas' fellow rapper Snoop Dogg has also invested in the free stock trading app Robinhood and, like his East Coast counterpart Nas, the Los Angeles-based hip-hop artist knows how to find a good business opportunity. Snoop Dogg's most notable investments include a stake in Reddit. The rapper has even co-founded his own venture capital firm, Casa Verde Capital, which focuses exclusively on investing in the marijuana industry, and has recently led a $9.5 million (£7.4m) investment in sleep coaching and supplement firm Proper.

Veteran actress Diane Keaton has a lucrative sideline that boosts her fortune no end: renovating and selling houses. The real estate developer favours historic Californian properties. Madonna snapped up one of Keaton's fixer-uppers back in 2002, and a Pacific Palisades house that Keaton bought in 2012 for $5.6 million (£4.07m) and renovated sold three years later for almost $7 million (£5.09m).

The Queen of Pop is just as successful in the investing stakes. But instead of focusing on real estate, Madonna has poured her cash into start-ups that have gone on to be wildly successful, including gym chain Hard Candy Fitness and Vita Coco, which has become the market-leading coconut water firm. Her net worth was estimated by Forbes at $570 million (£445.6m) in 2019.

The Hollywood leading man has made good use of his multimillion-dollar fortune, financing a variety of start-ups that have enjoyed great success. Smith's most impressive investments include partial ownership of the Philadelphia 76ers basketball team, and stakes in beauty line Carol's Daughter and BioBeats, a trailblazing digital health and AI firm. In 2018, Smith and Japanese footballer Keisuke Honda joined forces to launch a $100 million (£78m) Dreamers Fund, to help raise investments for start-ups.

Retired soccer manager Sir Alex Ferguson isn't just skilled at managing a world-class team. The former Manchester United boss is also an adept connoisseur of the grape. Ferguson, who has been collecting wine since 1991, owns a coveted collection of the stuff and made a tidy profit when part of the stash was auctioned in Hong Kong in 2014, netting a total of $2.9 million (£2.11m).

Gwyneth Paltrow created her Goop lifestyle brand in 2008, financing the website and overseeing its content. While Goop has weathered its fair share of ridicule, the lifestyle brand is thriving, especially since it bagged more than $10 million (£7.28m) in a Series B funding drive in 2016. In 2019, the company was estimated to be worth $250 million (£195m). Paltrow has also funnelled cash into game-changing kid's clothing brand Rocket of Awesome and Daily Harvest, a frozen health food start-up.

The former Major League baseball player retired in 2017 having earned a record $480 million (£375m) over his 22-year career. Since then, he's hit a home run with his investing activities. The retired sports star set up a holding company called A-Rod Corporation in 2003, which comprises a diverse portfolio of investments in real estate, construction companies, fitness centres and automotive dealerships. This year, Rodriguez and his partner, singer and actor Jennifer Lopez, bought stakes in Super Coffee, a New York coffee firm focusing on a sugar-free, enhanced coffee product, which is currently worth $240 million (£187m).

The Black Eyed Peas frontman and reality show judge is also one of the showbiz world's most successful investors. Getting in there during the early days, will.i.am invested in Twitter before its share price skyrocketed and was a founding shareholder in Dr. Dre's Beats. The rapper also hit the headlines after acquiring a $5.5 million (£4m) stake in UK online bank Atom in 2017.

Pop star Justin Bieber embarked on an investing career on the side in 2009 when he bought a stake in Spotify, which he is thought to have made a healthy profit on when the company went public in 2018. In 2013, he invested $1.1 million (£800k) in Shots Studios, which has since achieved great success making videos and films to place onto YouTube. The Yummy singer has invested in dozens of tech companies, according to his management.

Robert Downey Jr. is known for making clever tech investments that pay off very nicely further down the line. The actor's Downey Ventures investment company has financed a slew of hot-tipped digital start-ups, including celebrity-led training website Masterclass, and multi-channel network Maker Studios, which was purchased by The Walt Disney Company in December 2015.

 

There's no doubt Jay-Z is a talented investor and shrewd businessman, and with a reported net worth of $1 billion (£777m) he's the richest man in hip-hop. The award-winning rapper has his fingers in many money-making pies, having established a business empire with interests in fashion, real estate, sports teams, record labels and liquor, as well as a stake in Uber. But it hasn't all been plain sailing. In 2010, Jay-Z lost millions on a luxury hotel investment in New York that went disastrously awry.

The U2 frontman has his very own private equity firm called Elevation Partners, which has delivered mixed results. The company has made some seriously savvy moves, including acquiring a 2.3% stake in Facebook in 2009 that ended up paying off big time, and made Bono the world's richest pop star. However, the firm has floundered in recent years following a run of ill-advised investments.

In 2008, Kim Kardashian helped set up and funded fashion subscription service ShoeDazzle. A runaway success, the business was bought by a rival in 2013, netting Kardashian a massive profit. Her venture into bank cards wasn't quite as fortunate. The 'Kard' launched in 2008 but was withdrawn within months amid criticism over its astronomical fees. However, Kardashian has had better luck since. For Christmas in 2017, her husband Kanye West bought the reality star stakes in Apple, Disney, Adidas and Amazon, stakes that as of 31 August 2020 had each given her at least a 25% return on the initial investment according to The Motley Fool.

Britney Spears lost a pile of cash in 2002 when her Cajun-inspired New York restaurant Nyla went belly up after just six months, but since then the platinum-selling singer has more than made up for that investment faux pas. Spears has amassed a stellar share portfolio, with stakes in Google, Amazon and McDonald's, which have all enjoyed surging stock prices in recent years. However, since 2008 Spears's finances have been controlled by her conservators, including her father Jamie. In 2020 Spears challenged her father's role as conservator in court, but her request was rejected.

The socially-conscious star lost his investment in Mobli when the photo and video-sharing app shut down and filed for bankruptcy in 2016. Luckily, DiCaprio's other interests are doing well. He has sizeable stakes in several booming start-ups including mattress maker Casper and Rubicon Global, a sustainable refuse collection company. Adding to his portfolio of green investments, in 2019 he invested in Aspiration, a bank that offers customers green rewards while they save.  In September 2020 the Inception star put "significant" money in LA-based investment firm Struck Capital, which is committed to making LA a tech hub.

Rapper 50 Cent got rich and thankfully didn't die tryin', and while he was forced to declare bankruptcy in 2015 with debts of $36 million (£26m) and assets amounting to less than $20 million (£14.5m), the rapper has made some outstanding investment decisions in his time. These include an interest in Glacéau Vitaminwater, which made him $100 million (£72.75m) when it was acquired by Coca-Cola. In 2018, he denied he had made millions from Bitcoin, after reports that he'd made $8 million (£6.3m) from the cryptocurrency.

Justin Timberlake is brimming with talent, but his investing skills leave a lot to be desired. In 2010, Timberlake invested in image-tagging app Stipple. The company folded in 2014. Even worse, the entertainer was part of a consortium that bought the failing MySpace for $35 million (£24m) in 2011. This turned out to be a big mistake, and Timberlake reportedly sold his stake for just $1 (70p) in 2015. He has since invested more successfully in audio company AfterMaster and fruit drink company Bai.

During the late 1970s before his movie career began, Arnold Schwarzenegger managed to turn $100,000 into $1 million by investing in real estate. But his good investing work was almost undone in 1991 when he pumped cash into the Planet Hollywood restaurant chain, which went bankrupt twice.

One of the worst investment decisions ever, 1980s icon Kim Basinger snapped up the entire town of Braselton, Georgia for $20 million in 1988 (the equivalent of $43.9m/£34.1m in today's money) hoping to turn it into a movie-themed tourist attraction. She really shouldn't have bothered. Basinger failed to realise her ambitious plan and ended up selling the town for a hugely marked-down $1 million in 1994. 

Nicolas Cage had a lot of money to play with at the height of his fame in the 1990s and early 2000s, raking in $40 million a year during his heyday. But the one-time Hollywood leading man spent millions on a series of failed real estate investments. And so, hit particularly hard by the housing bubble of 2007, Cage was ultimately forced to declare bankruptcy in 2009.

Wrestling star Hulk Hogan was knocked down when he invested in the fast food industry. His Pastamania restaurant in the Mall of the Americas in Miami opened its doors in 1995, tempting diners with dishes including cheeseburger pasta and and Hulkaroni and cheese. But the crowds failed to flock and the joint closed within a year.

In 2008, Eva Longoria sank a chunk of the cash she earned from starring in Desperate Housewives into Los Angeles restaurant Beso, but the business struggled and filed for bankruptcy in 2011, finally closing its doors in 2016. Longoria's other food venture, a steakhouse in Las Vegas, fared just as badly. It shut for good in 2014 after just two years in business.

When a deal seems too good to be true, it probably is and so it proved for Kevin Bacon and Kyra Sedgwick. During the 2000s, the Hollywood couple invested heavily in Bernie Madoff's notorious $50 billion Ponzi scheme and were among the worst affected victims, pretty much losing their entire life savings.

Another Ponzi scheme victim, 24 star Kiefer Sutherland was relieved of the $869,000 he invested in a cattle scam during the late 2000s. Fraudster Michael Wayne Carr had promised bumper returns by buying cattle on the cheap in Mexico and selling to American farmers for inflated prices. Carr was jailed for the fraud in 2011.

Animal lover Natalie Portman thought she was doing the right thing when she invested a heap of money in vegan footwear line Te Casan back in 2008, but while the Jackie star should be applauded for sticking to her principles, she won't get any accolades for business acumen. Overpriced and unappealing, the $200 shoes didn't sell and the business folded after just a few months.

Unlike her ex-boyfriend Justin Bieber, who lucked out with his Spotify investment, Selena Gomez hasn't been quite as fortunate as a venture capitalist. In 2011, Gomez invested $750,000 (£585k) in postcard-creating app Postcard on the Run, which was also featured on ABC's Shark Tank show. The app failed to take off and was shut down in October 2015. But it hasn't put Gomez off, and she has since invested in ice cream brand Serendipity.

A diehard gamer, former Major League baseball star Curt Schilling gambled the bulk of his life savings in 2006 on his online gaming start-up 36 Studios, which he named after his jersey number. Yet despite a $75 million (£58.5m) grant from the state of Rhode Island, Schilling's business failed spectacularly. Out of cash and severely in debt, the company went bankrupt and shut down in 2012.

In 2014, Canadian singer-songwriter Neil Young launched a successful Kickstarter campaign to produce a high resolution music player and streaming service for audiophiles called PonoPlayer. The campaign garnered $6.2 million (£4.5m) and Young used his own money to fund the $400 player and music service. There was just one catch: PonoPlayer wasn't very good. The product didn't sell well and the streaming service effectively bombed.

Another sports star who invested abysmally, retired NFL player Mark Brunell lost his entire $50 million (£39m) fortune, filing for bankruptcy in June 2011. The football ace had invested in nine enterprises, five of which went under. Brunell's doomed real estate firm Champion LLC suffered the heaviest losses, losing him $11 million (£8.5m).

In 2013, former England national soccer team manager Sven-Göran Eriksson told the Daily Telegraph newspaper that he had lost $13.75 million (£10m) investing in ill-fated real estate deals. Eriksson blames his erstwhile financial adviser Samir Khan, who has since declared bankruptcy, for the catalogue of investment blunders.

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