Barry Diller Invented Prestige TV. Then He Conquered the Internet

Of all the egomaniacal lions who ruled Hollywood during the 20^th century gatekeeper era, very few made a brilliant pivot to the internet. The exception is Barry Diller. After leading programming at ABC, running Paramount, and supercharging Fox by launching its broadcast network in the late 1980s, Diller no longer wanted to work for anyone else. Either you are or you aren’t, he said of independence. As a free agent he quickly grasped the power of interactivity and built an empire that includes Expedia Group, almost the entire online dating sector (Tinder, Match, OkCupid), and an online media lineup that includes People, which wrote a hit piece on him early in his career titled “Failing Upwards.”

In his absorbing memoir, Who Knew, the third act of Diller’s career gets short shrift, as the road to becoming an internet billionaire is dispatched in a few dozen pages. The bulk of the book weaves his life as a not-quite-out gay man (who nonetheless passionately loves his iconic wife Diane von Furstenberg) with a deliciously dishy account of his Hollywood days. So as a WIRED kind of reader, I start our interview by calling him out on the tea shortage regarding his life in tech.

“What do you mean?” growls Diller, a notorious suffer-no-fools guy, who two weeks after publication is undoubtedly getting tired of book promotion. When I tell him I just wanted to hear wonderful details from his tech days, like the ones he shared about his earlier acts, his demeanor changes, and he cheerfully agrees with me. “I did whiz by it,” he says of his internet triumphs, citing time constraints. (Note: the book was 15 years in the making.) “It is something I should have done and I didn't do.”

I try to make up for the omission in our conversation. To get things started, I remind him of a 1993 Ken Auletta New Yorker profile titled, “Barry Diller’s Search for the Future.” It describes Diller’s quest for a post-Hollywood third act using the metaphor of his newly found obsession with an Apple PowerBook. A decade into the PC revolution, the idea of a media mogul actually using a computer was a novelty, and Auletta acted as if Diller had invented public key cryptography.

But the PowerBook was critical, says Diller. During his first job, as a 20-year-old working the mail room at William Morris, he buried himself in the archives and tried to read every single file and contract to understand the nuances of the business. In every subsequent job, he set out to absorb voluminous information before making critical decisions. It was his superpower. With the Apple laptop now he could have all this data at his fingertips. “I could do everything myself,” he says. “Tech has basically rescued me from my own obsolescence.” In the early ’90s—the perfect time to learn about the digital world, just before the boom—he went on a high-tech listening tour that included visits to Microsoft and the MIT Media Lab. “My eyes were saucers,” he says. “I ate every inch up.”

He also met Steve Jobs on his tour, who showed him the first few reels of a movie he was working on called Toy Story. “I’ve never had an aptitude for animation—I don’t like it,” Diller says. “Of course he was right and I was wrong. He pounded me to join the Pixar board, and I just didn't want to do it. Steve doesn't like to be turned down.” Diller describes his relationship with Jobs thereafter as tension-packed. He marveled at Jobs’ business savvy but despised his scorched-earth tactics. “The idea of having a 30 percent tax on going through the Apple store was, and is, an absolute outrage. It was pure Steve. But it’s breaking apart now,” he adds, referring to recent antitrust litigation that he’s clearly following.

When the internet took off, Diller went on a buying binge. Some prizes are mostly forgotten—CitySearch?—but others were inspired. He convinced Microsoft’s Steve Ballmer to sell him Expedia, and it became the centerpiece of a travel group that now includes Hotels.com, Orbitz, and Vrbo. The total valuation of his companies is now over $100 billion. He credits most of it to “luck, circumstance, and timing.”

The book provides evidence that there's more to Diller’s success than happenstance. Even before becoming his own boss, Diller operated like a founder. He joined ABC in his mid-twenties as a woefully inexperienced nobody, and bucked decades of tradition by arguing that the network should show films in prime time—and the ratings blockbuster Movie of the Week was born. Then he pushed ABC to make its own movies, and even created the mini-series, notably Roots. He invented prestige TV! When I tell Diller that this feat seemed to presage Netflix’s entry into original content, he agrees, and adds a bit of commentary to Hollywood’s current struggle with tech giants. “The incumbents stood by while Netflix took their business away from them,” he says. Meanwhile, he says, Apple and Amazon started their streaming services with different business incentives—the former to keep people in its ecosystem, the latter to keep customers signed up to Prime. “It’s hard to compete against that,” he says “It’s not that these old media companies aren't going to survive. It's just they’re never going to be the dominant player anymore. That's just gone.”

He writes that while the people he knows in the “algorithmic” movie business are even richer than the ones he hung out with earlier in his career, “I don’t know anyone who is having any fun.” In our conversation, he extols the satisfying process of creating a narrative film and bringing it to market. In comparison, the best tech has to offer is something like Tinder. When he first saw its nascent form—it basically adopted the “hot or not” format to a dating app—he saw great possibilities, and snapped up the team. Then came months of technical development. “The result was something thrilling, but it pales in comparison to the creation of content,” he says.

Diller, of course, is on top of the AI revolution. “It’s going to change so many things,” he says, comparing it to the shift from analog to digital. “Do you know Sam Altman?” I ask. I should have known better. The man who just wrote a book dropping the name of every Hollywood royal of the past 40 years says, “Sam is one of my closest friends, and has been since before he became Sam Altman.” Until recently, Altman sat on the Expedia board and helped the company integrate AI into the app.

I mention that if ChatGPT had existed when Diller first worked in the William Morris mailroom, he wouldn’t have had to painstakingly read every file. He could have simply uploaded the trove into a large language model and asked it questions. Anyone who did that would have Diller’s superpower! “I think you’re right,” he says. “That’s why I think the future is unpredictable.” Unless, as Alan Kay once said, you invent it.