Check Out The Best And Worst Celebrity Investors

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Celebrities who become investors have varying levels of success. While Mark Cuban certainly counts, he, and others like him, aren't included here because their fame was brought on by their investment history. All of the famous people discussed were well-known athletes, movie stars and musicians before the made the money they ended up using in a variety of fields, from tech start-ups and app funding to supporting businesses and backing entrepreneurs. This article will be broken into three sections: Celebrities with the Most Success, Mixed Success and Least Success. You’ll definitely be surprised by who ends up where...

Instagram - @theellenshow

Ellen DeGeneres is known as the current queen of daytime television, but what many of her fans don’t know is that she is arguably as successful in her other career as a house-flipping real estate investor. Along with her wife, actress Portia de Rossi, Ellen has owned, flipped and sold over a dozen properties. The couple will purchase and renovate the homes, the sizes and styles of which vary greatly, to sell for profit. She even did this with a $40 million mansion that she flipped for a $15 million payday.

Robert Downey Jr.

IMDb - Marvel Studios

Robert Downey Jr. is famous for decades of amazing film performances, especially his role as Iron Man in the Marvel Cinematic Universe, which reignited his career in the late 2000s. In those movies, he plays Tony Stark, a genius billionaire who, among many impressive qualities, is incredibly good with money. In real life the actor isn’t too bad with investments himself. Like his cinematic counterpart, he is connected to the tech world and has made some very smart plays in that field.

He has his own investment company called Downey Ventures that is responsible for financing a lot of digital start-ups. He has put money into Loot Crate, a subscription box service that features pop culture products related to video games, and of course, comic books. He’s also backed Masterclass, a series of interactive video courses taught by well known individuals like athletes, filmmakers and musicians. Downey Ventures also has its hand in The Walt Disney Company-owned multi-channel network Maker Studios, Inc., which is now called Disney Digital Network.

Justin Bieber

IMDb - Open Road Films

At just 24 years old, Justin Bieber is one of the most famous, and infamous, figures in pop culture, and has been for almost half his life. His unbelievably popular music has somehow managed to outshine his controversial personal life, helping to continue his rise to superstardom. While many of his questionable decisions have been appropriately scrutinized over the last few years, his investments have been pretty solid since 2009, when he bought a stake in Spotify.

Spotify has since become one of the biggest music-streaming services in the world, with over 157 million active users, more than 71 million paying subscribers and a revenue of almost $5 billion. The fact that Bieber got in when the company had only been around for a year is very impressive. He also put over a million dollars into the selfie app Shots Studios, an entertainment company that manages talent and production. Bieber holds stake in a dozen other companies in the digital space.

Snoop Dogg

Instagram - @snoopdogg

Calvin Broadus, aka Snoop Dogg, is as beloved as he is well known. It seems like he does everything right, from music to television and yes, even investments. Snoop has backed the app Robinhood, which operates in stock trading, as well as Reddit, a massively popular website that promotes itself as “the front page of the internet." And, of course, Snoop invests in many legal cannabis services like Merry Jane, LeafsBySnoop, FunkSac, and Eaze.

Jessica Alba

Twitter - @jessicaalba

Jessica Alba hasn’t been in as many movies lately, maybe because she’s so focused on making great investments. She is a co-founder of Honest, a hugely successful ethical skin care firm. The company started, largely with her help, in 2011, and is now worth billions, which is amazing considering she owns a 20% equity stake. Alba has also backed Headspace, a mindfulness app, the senior home care service Honor, and Managed by Q, an office cleaning company.

Kobe Bryant

Instagram - @kobebryant

Aside from being one of the best basketball players of all time, Kobe Bryant is also a great investor. He's retired from the NBA, which gives him plenty of time to back start-ups with his partner, venture capitalist Jeff Stibel. In 2016, the two teamed up to start a $100 million dollar investment fund that has stake in a variety of companies including Scopely, a touchscreen entertainment network, Reserve, a dining concierge app, and VIPKID, an online education company.

Will Smith


Will Smith has remained relevant for decades as an actor, musician and, unknown to some, a brilliant investor. He amassed a multimillion-dollar fortune over the course of his illustrious career, and uses the money wisely. He claims partial ownership of his hometown basketball team the Philadelphia 76ers. Smith also has stake in Vastrm, a men’s clothing company, Carol’s Daughter, a successful beauty line and BioBeats, a forward-thinking digital health firm, which also uses AI.

Gwyneth Paltrow

Instagram - @gwynethpatrow

Another actress who hasn’t been as active in Hollywood lately is Gwyneth Paltrow, who has also done very well for herself in the investment space. In 2008, she created Goop, her own lifestyle brand. She also financed the website and oversees its content. The multimillion-dollar company has received its fair share of controversy, but is still successful. Paltrow also invested in Rocket of Awesome, a children’s clothing brand, and Daily Harvest, a health food start-up.

Dr. Dre

Flickr - Jason Persse

It goes without saying that legendary rapper/producer Dr. Dre is also a world-class investor. And it only took a single brilliant investment to make him one of the richest on this list. It’s perfect that Beats makes headphones, seeing as it’s directly connected to music. The company has been doing great since it debuted in 2008, but things went to the next level when Apple bought it for $3 Billion, earning Dre over a half a million for himself.

Carmelo Anthony

Twitter - @carmeloanthony

Athletes are also great investors, with more to come in this article, and Carmelo Anthony is definitely one of them. The NBA All Star actually has his own investment firm, Melo7 Tech Partners. He founded the company in 2013 with his partner Stuart Goldfard. Over the last five years, they have backed 28 start-ups, as well as nine acquisitions, that vary from apps to women’s fashion and even a physical storage service.

Jared Leto


Jared Leto is both an Oscar-winning actor and a world famous musician, thanks to his band 30 Seconds To Mars. If that wasn’t enough, he’s also one of the smartest celebrity investors. He is not only responsible for backing start-ups in the tech industry, but he also acts as an adviser for some of them. Leto has backed over 50 companies including Uber and Airbnb, two of the biggest new brands.


Twitter - @iamwill

Will.I.Am went from a music superstar as a member of The Black Eyed Peas to a judge on the hit reality television show The Voice. Somewhere in between he also became a successful investor. Some of his earliest plays were Twitter and the aforementioned Beats, both of which are now huge companies. He’s also backed several tech start-ups and has made millions as a result.

Tyra Banks

Twitter - @tyrabanks

Another multitalented investor is Tyra Banks, the former Victoria’s Secret angel and host of America’s Next Top Model. She has invested in a number of successful companies including The Muse, a lifestyle assistance service, VideoGram, a video greeting card company, and Locket, a lockscreen app that was acquired by Wish, a rival firm, which earned Banks a healthy payday.

Alex Rodriguez

Instagram - @arod

Another successful investor who was also a professional athlete is none other than Alex Rodriguez, also known as A-Rod, the former Major League Baseball player who was one of the best Yankees ever. In 2003 he founded A-Rod Corp., a holding company that has invested in multiple areas from automotive dealerships, construction companies, real estate and fitness centers.

Ryan Seacrest

Twitter - @ryanseacrest

Ryan Seacrest is known for being one of the busiest people in Hollywood, hosting countless shows and producing just as many, if not more. He’s also made some great investments in various start-ups, including Headspace, a mindfulness app, and Stamped, a social sharing platform, as well as ATTN: and Digitour Media.


Instagram - @madonna

One of the biggest icons in this article is Madonna, the Queen of Pop. Beyond her decades of success in the music and fashion industries, she, like many of the celebrities in this article, has intelligently invested in start-ups, getting in at the ground level of companies, like Hardcandy Fitness and Vita Coco, that have grown to be very successful.


Instagram - @nas

World-class rapper Nas has also made a name for himself in the venture capital world. He founded a VC firm called QueensBridge Venture Partners that has helped to fund over a hundred companies. He and his investment partner, Anthony Sales, have backed dozens of tech start-ups, as well. He has his hands in apps, gyms, clothing brands, ticket platforms, moving companies, stock trading and more.

Diane Keaton

IMDb - Sony Pictures Classics

Diane Keaton is another Oscar-winner turned investor. She’s been acting in Hollywood for decades, and also managed to become a very savvy real estate developer. She renovates and sells properties all over California. Keaton is the first celebrity in this article since Ellen to focus solely on one field, opting out of opportunities in the tech space and backing start-ups, which has served her well.

Magic Johnson

Instagram - @magicjohnson

NBA legend Earvin “Magic” Johnson is the final basketball player in the positive section of this article. He not only set up his own investment company, Magic Johnson Enterprises, but he also owns his own line of movie theaters, as well as over 100 Starbucks. He went from a part-owner of his former team the Los Angeles Lakers to owning baseball’s Los Angeles Dodgers along with a group of other investors.

Alex Ferguson

Twitter - @H14AFC

Alex Ferguson might not be as recognizable as the celebrities in this article, but his fame in the realm of sports, specifically soccer, rivals that of anyone else. He managed the world-class Manchester United and also developed quite a skill for collecting wine. He amassed an amazing assortment, over the course of a couple decades, that sold for millions at a Hong Kong auction in 2014.

Ashton Kutcher

Twitter - @aplusk

We saved the best for last, on the successful side, that is. Beyond being the most prolific celebrity investor with his hands in almost 50 start-ups, Kutcher has invested in Airbnb, Foursquare, Uber, Spotify, Shazam and Soundcloud.

As promised, the article will now shift into celebrity investors who have had mixed luck. This by no means implies they aren’t successful, but they have made some bad calls that most of the previous entries managed to avoid.

Leonardo DiCaprio

Twitter - @leodicaprio

While many of his investments have been successful, including his mattress start-up Casper and the mobile phone company Solarin, Leonardo DiCaprio has also had some bad luck. Mainly with Mobli, a photo and video sharing app that shut down and filed for bankruptcy in 2016. He is very socially conscious and has also backed the sustainable refuse collection company Rubicon Global.

Kim Kardashian

Instagram - @kimkardashian

Kim Kardashian is arguably as financially successful as pretty much everyone else in this article, with significant stake in multiple fashion brands. But even she is not immune to bad investments. Kardashian tried her hand in the world of finances when she launched her own debit card “Kard” in 2008. It was withdrawn almost immediately due to its ridiculous fees and all the subsequent criticism.

Justin Timberlake

Twitter - @jtimberlake

Pop icon Justin Timberlake has been successful in a variety of fields, from music to movies, as well as investments, with millions of dollars in money-making start-ups. But in what is one of the worst moves ever, he was a part of the group that tried to revive the failing Myspace. He also attempted to compete in the app space with Stipple, an image-tagging service that folded in 2014.


Hype Beast

Shawn Carter is anything but unsuccessful, with his portfolio sporting so much more than just his award-winning music catalog. He’s invested in a lot of different areas, including even food and beverages. But at one point he lost millions of dollars after a failed luxury hotel investment.

Britney Spears

Instagram - @britneyspears

While she’s had her fair share of ups and down over the course of a lengthy career, pop star Britney Spears has found a lot of success in the investment space. She has stake in McDonald’s, Amazon and Google. But in 2002 she attempted to enter the incredibly-difficult and highly-completive food world with Nyla, her Cajun-cuisine restaurant in New York that failed in a matter of months.

Arnold Schwarzenegger


Arnold Schwarzenegger has gone from one of Hollywood's biggest actors to the Governor of California. He also managed to become a successful investor in the real estate world. Unfortunately, he was a part of one of the most infamously terrible investments ever. Along with fellow movie stars Sylvester Stallone and Bruce Willis, Arnold lost a lot of money on the failed Planet Hollywood restaurant chain.

50 Cent

Instagram - @50cent

After being one of the most successful rappers at the turn of the century, Curtis Jackson has gone on to invest in Glaceau Vitaminwater, which was acquired by Coca-Cola, and SMS Audio, a consumer electronics company. But in 2015, he had amassed $36 million in debt, causing him to file for bankruptcy. He has since been rumored to play in the bitcoin space, but he denies this activity.


Instagram - @U2

The final entry in the mixed section of this article is Bono, the U2 frontman and famous activist. He owns Elevation Partners, a private equity firm that has experienced plenty of ups and downs. While they succeeded with investments in Facebook, they’ve also misfired in a variety of fields.

And finally, with the good must come the bad. The remaining celebrities have sadly made more bad investments than they have good ones, so without further ado...

Selena Gomez

Twitter - @selenagomez

As maybe the most relevant female pop star in this article, Selena Gomez shouldn’t be too ashamed of her unfortunate investments. With countless hit songs and sold out tours, she can afford to take some financial risks. Sadly she sunk almost a million dollars in Postcard on the Run, an app that couldn’t succeed even after appearing on the hit ABC show Shark Tank.

Neil Young

Wall Street Journal - Matt Furman

Neil Young is one of the more iconic and important musicians in Rock and Roll history, but unfortunately that success hasn’t exactly translated to the investment world. In 2014, he attempted to break into the very difficult music player space with a Kickstarter campaign for his high-resolution product. Beyond the $6.2 million raised, he largely funded the failed service with his own money. But it didn’t sell and eventually went under.

Natalie Portman

Harpers Bazaar

Oscar-winner Natalie Portman is almost always right when it comes to her choice in movies, but not as much with her investments. A decade ago, the known animal lover backed Te Casan, a vegan footwear line, which ended up failing due to a lack of sales that many attribute to the high price of the product.

Nicholas Cage


Nicholas Cage is as famous for his financial issues as he is for his films. He’s an award-winning actor who’s gone from indies to Oscars and blockbusters, but Cage has also lost a lot of his money on bad real estate investments. He was heavily involved in the housing market when it crashed and the bubble popped in 2007. Two years later he filed for bankruptcy.

Eva Longoria

Twitter - @evalongoria

After earning millions starring in the hit television show Desperate Housewives, as well as a number of successful movies, Eva Longoria did what all of the celebrities in this article have done: she started investing. But like the aforementioned Britney Spears, she failed at an attempt to enter the restaurant space with Beso in Los Angeles, as well as a steakhouse in Las Vegas.

Kevin Bacon and Kyra Sedgwick

Instagram - @kevinbacon

Hollywood power couple Kevin Bacon and Kyra Sedgwick have starred in countless hit films over the course of their impressive careers in the movie industry. Unfortunately, they also played roles in one of the most famous financial blunders, Bernie Madoff’s $50 billion Ponzi scheme. And the couple wasn’t just a small part of it, they almost lost their entire life savings.


Hulk Hogan

Flickr - Simon Q

Once he retired from being arguably the most popular professional wrestler of all time, Hulk Hogan saw a similar kind of failure as many of the other celebrities in this article who have attempted to break into the food space. He started investing in the industry back in the ‘90s when he opened his own failed Italian restaurant called Pastamania in Miami’s Mall of the Americas.

Kiefer Sutherland


Kiefer Sutherland was one of the first movie stars to successfully transition into television, with starring roles in 24 and other popular shows. While he wasn’t involved with Bernie Madoff, he did get caught in another Ponzi scheme that lost him almost a million dollars. The man responsible, who tricked investors by offering a deal in a cattle farming endeavor, ended up going to jail for fraud.

Kim Basinger


While making successful choices as a Hollywood actress throughout her career, Kim Basinger was also involved in one of the most unusual failed investments in this article. Decades ago, in the ‘80s, she actually purchased an entire town. And that’s not even the weird part. She wanted to turn Braselton, Georgia into a movie-themed tourist attraction. She payed $20 million but had to sell it for only $1 million years later.

Burt Reynolds


Burt Reynolds is definitely a cinematic icon, having starred in numerous hit films for several decades. But a bad investment cost him tens of million of dollars. He invested $20 million in a food chain called Po’ Folks, but when it filed for bankruptcy, he lost everything and eventually had to file for bankruptcy himself. He is the final of many celebrities discussed here who have failed attempting to make it in the restaurant business.

Curt Schilling

Flickr - Dodnews

It’s fitting that the final individuals of both the most and least successful sections in this article are from the world of sports, and aren’t necessarily as famous as everyone else. But their investments definitely deserve to be discussed. Former MLB star Curt Schilling lost a lot of his life savings when he gambled on 36 Studios, an online gaming service that went bankrupt in half a decade.

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