The Haute Auctioneer
Alexander Gilkes (34)
Cofounder of Paddle8, New York City

The buying and selling of fine art, traditionally reliant on face-to-face meetings and personal connections, has proved remarkably resistant to digital disruption. To Alexander Gilkes, that was an opportunity to launch the auction site Paddle8. Gilkes—a 34-year-old Brit who went to Eton, is a friend of Princes William and Harry, and was handpicked by Simon de Pury to run global marketing at Phillips de Pury auction house in New York—brings society and gallery contacts to Paddle8 while cofounder Aditya Julka oversees the business side. The site focuses on pieces valued up to $100,000, a figure low enough to avoid direct competition with the big auction houses but high enough to offer buyers a chance to snag an underappreciated Neo Rauch or an early Wade Guyton print. Last year, the three-year-old start-up brought in nearly $40 million in bids and caught the attention of Damien Hirst, who, with a consortium of art-world insiders, invested $6 million. Now Paddle8 is expanding into design and collectibles and opening offices in Los Angeles, London, and Hong Kong. As Gilkes says, "There is an international audience craving access to these types of things."

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The Bridge Builder
Troy Carter (41)
CEO and founder of Atom Factory, Culver City, California

As the tech and entertainment industries converged over the past few years, it became clear that neither side quite understood the other. "There were a lot of misconceptions," says Troy Carter, the man who signed Lady Gaga in 2007 and, as her manager, helped turn her into a phenomenon powered as much by social media as by music and fashion. "People in Silicon Valley didn't value content, and people in Los Angeles didn't value technology." Carter started serving as a translator between the two worlds, at one point bringing then–Google CEO Eric Schmidt in to help him fund a social platform that became the foundation for Gaga's, as well as community sites for Coke and Nike.

But then, late last year, disaster: He and Gaga parted ways (a decision Carter admits was hers). Except it hasn't played out as a disaster, at least not for Carter. The 41-year-old doubled down on making back-channel connections between tech and entertainment players, dispensing advice and doing deals with artists, start-ups, venture capitalists, and captains of industry.

Carter's Atom Factory continues to manage musical acts (John Mayer, for one), but he is increasingly investing in new technologies. His strategic advantage: taste and intuition. "At the end of the day, these are gut decisions," he says. His gut has yielded big wins, with early investments in Dropbox, Warby Parker, Spotify, and Uber—to which, naturally, he brought Jay-Z's Roc Nation as another backer. "We look at entrepreneurs the same way we look at artists."

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The Screen Savers
Who says tech is out to kill the movie business? It's time to pass the popcorn again, as these upstarts are using technology to bring people back into theaters.

Olenka Polak (20)
Cofounder of MyLingo, Los Angeles

Who: Polak formed the company with her brother Adam after her freshman year at Harvard, where she won the school's Innovation Challenge as a sophomore.
What: The app allows users to download foreign-language tracks to films that sync perfectly with the action onscreen. Suddenly, the theatergoing experience is open to millions of non–English speakers, who no longer have to wait for the DVD.
Stirring the Melting Pot: "This is an underserved market that hasn't been addressed by Hollywood."

Stacy Spikes (46)
CEO of MoviePass, New York City

Who: A seasoned entertainment exec from Miramax and Motown, Spikes started MoviePass in response to dwindling audiences in theaters.
What: The MoviePass app offers subscriptions for going to the movies—as many as one movie every 24 hours, for a flat fee.
If You Build It, the Youth Will Come: "The 18-to-35 group makes up 75 percent of our demo, and when they use MoviePass, they go 64 percent more than they did before."

Nicolas Gonda (29) and
Pablo Gonzalez (35)

Cofounders of Tugg, Austin

Who: Gonda (left, top), a movie producer whose credits include Terrence Malick's The Tree of Life, and Gonzalez, a tech whiz, started Tugg to bring indie films to places where the multiplex is the only game in town—and recruited Ben Affleck, Richard Linklater, and Malick as advisers.
What: Through Tugg's website, movie buffs can screen art-house fare and program custom cinematic events in theaters across the country, including most of the big chains.
DIY Distribution: "We enable any filmmaker to bring their film onto the site," says Gonda—and then anyone can crowdsource an audience and screen it.