Given that America's entertainment and tech capitals are located in the same state, it's no wonder that the two very different worlds of Hollywood and Silicon Valley have taken an interest in one another. And while it isn't rare for famous entertainers to get involved with startups in some capacity, only a handful have really made noteworthy contributions--whether in the form of a large one-time investment or through a series of multiple strategic deals. Read on to see some of the biggest investments celebrities have made to date.
U2 lead singer Bono co-founded Elevation Partners in 2004, a venture firm that focuses on media, entertainment and technology companies and manages $1.9 billion in assets. The firm's highest-profile investment came in 2010, when it bought $120 million in Facebook stock, giving it a 1.5 percent stake in the social media company. (Elevation also had made a $90 million investment earlier.) After Facebook's IPO in 2012, the firm sold 11.5 percent of its shares, netting Bono an estimated $10 million.
2. Leonardo DiCaprio
In 2011, acclaimed actor DiCaprio led a $4 million investment round in Mobli, a Tel Aviv-based photo sharing app maker. DiCaprio came on as an adviser to assist with branding and marketing, as well as to help the company gain access to other celebrities, VentureBeat reported. More star power soon arrived: Actor Tobey Maguire and athletes Lance Armstrong and Serena Williams also have invested in the company. Mobli, however, has yet to mount a major challenge to its popular competitor, Instagram.
3. Ashton Kutcher
The Two and Half Men star has made a name for himself as a notable tech investor over the past several years. In 2009, he invested an undisclosed amount in Skype, which Microsoft bought for $8.6 billion two years later. Through his venture capital fund A-Grade Investments, Kutcher and his co-founders Guy Oseary and Ron Burkle have invested in more than two dozen companies including mattress maker Casper, car sharing service Getaround, and e-commerce company Fab. To further his reach, Kutcher formed Sound Ventures earlier this year with Oseary, who also is Madonna's manager. Details about the size of the fund have yet to be released, but the founders reportedly plan to invest in later-stage startups.
4. Jared Leto
Until recently, Golden Globe Award winner Leto had been one of the lower-profile celebrity investors. But the actor already has made more than 40 investments in companies like Blue Bottle Coffee, HR software company Zenefits, and video streaming app Meerkat. Leto has said that his best investment, both creatively and financially, was in Internet of Things company Nest Labs, which Google acquired for $3.2 billion in 2014.
Rapper Nas has invested in dozens of startups, including including Bitcoin services provider Coinbase, text annotation website Rap Genius (now called Genius), and the online art community DeviantArt. He and his manager Aymen Anthony Saleh reportedly have pledged to dedicate more than half of their entire portfolio to startups. Nas has differentiated himself from other celebrity investors in part by frequently teaming up with Ben Horowitz, an established Silicon Valley venture capitalist. The two investors met while participating on a Rap Genius funding round, and Horowitz has been an adviser to Nas and Saleh ever since.
After reportedly drinking Vita Coco coconut water every day while on tour, Madonna invested $1.5 million in the brand in 2010. Other investors included her manager Guy Oseary, actors Matthew McConaughey and Demi Moore, and Red Hot Chili Peppers singer Anthony Kiedis. The investment appears to be paying off. Coconut water's popularity has been soaring in recent years, and Vita Coco has an estimated 40 percent market share in the United States. The brand is sold in 30 countries worldwide and did $421.1 million in global retail sales last year, according to The Wall Street Journal.
7. Magic Johnson
After NBA star Earvin "Magic" Johnson retired from basketball, he made a name for himself in the world of business. Among other ventures, he opened a chain of movie theaters, a series of fitness clubs, and several Burger King franchises. In 2010, Johnson divested his Starbucks holdings (at one point he owned more than 100 franchises) and his Los Angeles Lakers shares--two sales that together were worth more than $100 million. The following year he invested an undisclosed amount in venture capital firm Detroit Venture Partners and signed on as a general partner. Its first fund, Detroit Venture Partners LP, raised $55 million. The firm has invested in more than a dozen early-stage tech companies.
8. Justin Bieber
Pop star Bieber is somewhat secretive about the investments he's made; he invested in his first startup in 2009, but has not revealed the company's name. Since then he has taken a stake in instant messaging app Tinychat, ratings app Stamped, and music streaming service Spotify. Unlike many celebrity investments, the deals are rarely equity-for-endorsement trades. One exception is Shots, a selfie sharing app for which he led a $1.1 million seed round. Shots's popularity spiked when Bieber started using it to post his own photos. Though its adoption seems to be slow going, the company raised a $8.5 million Series A round earlier this year.
9. Ellen DeGeneres
In 2011, a group of ex-Googlers launched Stamped, an app for reviewing businesses and restaurants. A year later when the app was relaunched as a tool for users to track all of their favorite things--like books, movies and music--comedian and talk show host Ellen DeGeneres wanted in. (She was joined by a host of other celebrities, including television host Ryan Seacrest, Justin Bieber, and Google executive chairman Eric Schmidt in a $1.5 million seed round). Marissa Mayer decided to make Stamped her first target after taking over as CEO of Yahoo, and in 2012, purchased the startup for $10 million.
10. MC Hammer
Stanley Kirk Burrell, known professionally as MC Hammer, has quietly had a presence in Silicon Valley as an adviser and investor for more than a dozen years. Back in the early 2000s, when Pandora was still called Savage Beast, Hammer coached founder Tim Westergren for meetings with music executives, according to Billboard. Among the musician's investments are in contact-sharing app Bump Technologies, mobile payment company Square, and magazine app Flipboard.