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Why Barry Diller believes in cultivating creative conflict

The legendary entertainment and media executive talks to Fast Company’s editor-in-chief about his instinct for spotting talent and why he likes to promote from within.

Why Barry Diller believes in cultivating creative conflict
[Illustration: Señor Salme]

As a Hollywood executive, Barry Diller helped shape the careers of former Disney CEO Michael Eisner, onetime Columbia Pictures president Dawn Steel, and DreamWorks cofounder Jeffrey Katzenberg, who, among many others, became known in the industry as the “Killer Dillers.” As chairman and senior executive of media and internet conglomerate IAC and chairman of travel juggernaut Expedia, he has mentored Mindy Grossman (now CEO of Weight Watchers) and Dara Khosrowshahi (CEO of Uber). In today’s era of data-driven talent management, Diller’s ongoing success offers a reminder of the power of intuition.

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Fast Company: You’ve identified and nurtured high performers across several industries and businesses for many years. Putting aside job titles and functions, what traits indicate great talent?

Barry Diller: I would say there are none, when [employees] begin. Bring people into an organization–young, inexperienced, but with energy, and edge–and drop them into water above their heads as quickly as you can. Some survive. And those who survive answer your question. Everything is idiosyncratic. There’s no rule book. I’m probably the worst person to ask about this topic, but anyway, you’re the one who called.

FC: What’s the best way to help creative types excel?

BD: Put them to work! Let us assume that the task is writing, something you may be familiar with. The only way to write, say, for television or film, is to write. Hopefully you will be sending that first or twentieth draft to somebody, and if they’re any good, they’ll help you [develop] your craft. It’s process. It’s one [foot] in front of the other.

FC: I’ve heard people say: “If you deliver for Barry Diller, he’ll deliver for you.” Do you think this philosophy, of being demanding but loyal, has helped attract talent to you?

BD: It depends. I’ve always said that I believe deeply in creative conflict, and that means passionately arguing–whatever your thoughts are, whatever the point is. Some people love that and it helps them grow, learn, etc. Some people run for the hills. I’ve always said to people, “Look, it’s not a room for everybody. If you like this environment, great. If you don’t, please leave, because it’s not good for any of us.”

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FC: How do you feel about the term “Killer Dillers”?

BD: Well, I guess it makes me smile a little because it’s got some nice and not-so-nice connotations. I kind of like both sides of that.

FC: One of your protégés has been in the news lately: Dara Khosrowshahi, who took over from founder Travis Kalanick as the CEO of Uber. How has he evolved as a talent?

BD: [He’s] the perfect example of what I told you before. Dara Khosrowshahi we saw as a young analyst at Allen & Company, God knows, 100 years ago? He came to one of the [IAC] progenitor companies, as basically an analyst/clerk. And each year or two or three, we threw more and more at him until we finally said to him, after he had become CFO of one of our public companies, “We’re going to spin off Expedia, and I think you’re going to go run it.” He said, “But I don’t have any operational experience.” And I said, “Yeah, that’s the good thing.” Twelve years later, he left to go run Uber after having spectacularly grown Expedia.

FC: When you were CEO of Fox, you hired Leonard Goldberg, who had given you your start in television 20 years earlier at ABC. Typically, you like to promote from within. Why the departure?

BD: It’s not one-size-fits-everything. There are different circumstances. I would say that my preferred method is not to ever hire outside your company for senior positions. It is at least 50% disappointing.

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FC: Can you elaborate on that?

BD: I mean, because there is organ rejection. Every once in a while, for a certain position, you have to do it, but if you do it consistently, I think it’s the definition of a poorly managed company.

FC: Tinder, and its cofounder Sean Rad, emerged from an incubator that you funded and fostered. What do you think about incubators as an approach to finding and nurturing talent?

BD: Well, they’re inherently crapshoots. They’re speculations, and you’re really not looking for the kinds of ratios you should look for in directly managed businesses. If you’re rational and objective, you know that a great many of them will fail. Every once in a while, though, something good happens. Tinder is an example of that.

FC: You have a long history of mentoring women. Is this something you’ve done consciously?

BD: I’m lucky I never made any distinction. Why, I can’t really tell you. I just didn’t.

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FC: IAC has a number of women running portfolio companies, such as Vimeo CEO Anjali Sud and The Daily Beast CEO Heather Dietrick. Do you think they run their companies differently?

BD: Yes.

FC: How so?

BD: They are women, not men.

FC: But they have to perform or they wouldn’t get to stick around. I didn’t say that they perform better or worse. That’s ridiculous. But when you say, “Do they run them differently?”

BD: Yes, they are a different gender. You can be neutral about [gender] in terms of making choices, but there are gender differences, and I think that’s good.

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FC: I imagine that politicians solicit you all the time for money.

BD: Yes.

FC: Do you see any breakout talents in politics today? Are there people who could, were they not in politics, thrive at IAC?

BD: Few, I’m afraid.

FC: Is that because politics and business require different skill sets or energy levels? It’s like the difference between educators and film stars.

BD: I mean, they’re the other sides of the hemisphere. There’s nothing in common.

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FC: What about media and technology, two worlds where you have a lot of experience. Do you think the talent requirements there differ?

BD: Generally, yes. Technology is zeros and ones and an affinity for that. And a narrative storyteller is very much the opposite of that. There’s no commonality there. There’s more a magnet repellent.

FC: Tech and media companies seem to want to collaborate, but it seems like the pairs that succeed are the exceptions, not the rule.

BD: It’s hopeless. Collaboration is hopeless. It doesn’t mean one can’t buy the other, but I would not put them in the same room.

FC: What turns you off when you’re talking to a potential job candidate or young person?

BD: Someone with too many specific goals.

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FC: What advice would you give people early in their career? Is there anything that you would tell young readers of Fast Company?

BD: Yes. Begin.

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