Barry Diller on Serendipity, Sexuality and Success
- Holly Peterson
- May 21
- 7 min read
Updated: May 21
In a new memoir, ‘Who Knew,’ Diller credits luck over talent in helming multiple Hollywood studios and television networks: ‘It’s the timing, stupid.’
By Holly Peterson
Illustration by HelloVon Studio for WSJ. Magazine
May 20, 2025 11:00 am ET
Success, they say, is inspiration plus perspiration. But what of sheer universe-vibration? We ask the most successful people we know to tell us what role luck plays in one’s career.
ICONOCLASTS DON’T waste their time or ours. We know entertainment mogul Barry Diller bested most of his rivals, although a few—notably Sumner Redstone—outmaneuvered him. So when Diller takes his gloves off in his new memoir, he confronts what we couldn’t see. His backstage positioning to chomp entire companies whole; the contrast between working for someone else versus for himself; and, on a personal level, his demons. Case in point, Diller on his attraction to men: “I had wanted so desperately to alter my sexuality as a child and teenager and I had tried so hard and failed. I was left with an unquenchable need to be vigilant about every other aspect of my life.” On his much gossiped-about relationship with his now-wife, Diane von Furstenberg: “We aren’t just friends. Plain and simple, it was an explosion of passion that kept up for years.”
Diller broke out of the William Morris mailroom at age 24 and turned the Movie of the Week at ABC into must-see TV, producing hits including Go Ask Alice and Brian’s Song. Ever heard of Saturday Night Fever or Raiders of the Lost Ark? Both came out during his decadelong stewardship of Paramount from the mid-1970s to mid-1980s. After more than seven years running a second major studio, Twentieth Century Fox, and releasing blockbusters such as Home Alone, he left Hollywood and went on to acquire the Home Shopping Network (HSN). Before most of his peers understood the term interactivity, Diller had seized on the commercial potential of merging telephones and televisions. He also made a series of strategic acquisitions that transformed his media holdings into a diversified digital empire under IAC (formerly InterActiveCorp).
Unlike many entertainment or business icons who write memoirs to bolster legacies and egos, Diller faces facts: No one can run or reposition several studios and networks without a few spectacular swan dives. He remembers a time in the mid-1990s when he was “a mogul manqué,” “nationally known damaged goods,” after losing his bid to buy Paramount. He recounts “glorious dead ends” and how Google “manhandled” him out of opportunities. But he never let these setbacks hamper his momentum. Instead, he owned the simple truth: They won. We lost. Next.
On his relationship with his wife, Diane von Furstenberg: ‘We aren’t just friends.
Plain and simple, it was an explosion of passion that kept up for years,’
Barry Diller writes in his memoir, ‘Who Knew.’
Photo: Barry Diller
You are not a cynic. Why?
Cynicism kills instinct. If you are cynical, it’s very difficult for your instincts to remain pure enough to be determinative about things. Naiveté is mandatory for keeping your instincts alive. It’s not true in technology, particularly, but in creative arts, instinct is mandatory. And being naive is just much better, by the way, it’s nothing you can decree. You either are or you’re not.
Do you believe coping mechanisms that help you survive childhood screw you up in adulthood?
How could they not? Compartmentalizing is efficient, but it builds up walls. It makes it very hard for you to bust through. It wouldn’t have been good if [as a child] I didn’t have the ability to find safety in the compartments. Yet when you do that, you draw such hard boxes around everything that you can’t easily bust out. So yeah, it ain’t a good thing.
Your memoir tells of parents who were in the home, but emotionally absent to unimaginable levels. Never celebrating birthdays or holidays, no interest in who your friends were or how you fared in school. Talk to me about how that relates to your drive.
I think the need to count is true in most people who are successful, particularly excessively so. It’s just so basic and powerful that it is a driver.
Who do you know who’s a powerful and fierce leader, woman or man, who seems calm, generous, self-aware, confident in their skin, not screwed up. Can you think of one?
I would give you Jamie Dimon as a good example. I don’t know any demons Jamie has, but he has an equanimity that I think is true in all phases.
You love to be contrary. Are you fearless in business?
So long as I was not having to assert myself, it gave me an extra weapon of not being afraid. So many people are afraid. You can see it in their inability to challenge, to be confrontational, to be direct.
What about hiding your homosexuality? What role did it have in your success?
As a teaching mechanism? Nothing. As for forcing me into being humanistic? I think everything.
From left, Diller, Calvin Klein and Doug Cloutier in Malibu, Calif.
Photo: Barry Diller
Let’s talk about instinct versus data. If you like an idea, do you go for it, or study it with a team?
What’s the idea? Full stop. Most research cannot tell whether an idea is good or not. The problem with testing anything is that research often leads you in the wrong direction.
Give me a hardcore business example where your data people were putting flowcharts in front of you and you said, “No, I’m going with my instinct on this, I’m ignoring you all.”
Most entrepreneurial pursuits of originality would be rejected by a deep data analysis. There are so many instances in my life where we’ve gone against research and data. When we got into the personals business [Match.com], all the data told us that the public would never adopt the online dating model.
Do you believe you prepare for luck, so you recognize it when it comes? Or does it magically appear one day?
It’s pure serendipity. Yes, we can break down the word luck, but to me serendipity perfectly describes events that are inexplicable. And I have so many of them in my life that to ignore it would be totally ridiculous.
Why do you credit serendipitous moments—or, as you say in your memoir, “the timing, stupid”—over your talents when you took over entire entities and saved them?
Who could have decreed that the day I joined ABC [in 1966] to work for a lower-middle-level executive they fired the boss levels above him, and he was named to run the whole operation? Where’s the prediction of that? Or, in 1984, I decided I had to leave Paramount. I get in the elevator, go downstairs, and there on the phone is a message from Marvin Davis, who owned Fox, offering me a way out. Where does that come from?
Unlike many entertainment or business icons who write memoirs
to bolster legacies and egos, Diller faces facts in ‘Who Knew.’
Photo: Simon & Schuster
Many would say you earned those moments.
When I hear people’s egos outsizing themselves on their accomplishments, and they think it’s about them solely and their wonderful talent—it is often not. It’s often about the timing of their circumstances.
When you invested in QVC, you had this vision about the convergence of television and the telephone that was not in sync with your contemporaries. Some questioned your sanity.
When I went to QVC, everyone thought I had truly lost my mind. What, are you kidding? The idea that I thought [home shopping] was primitive convergence, resulting in interactivity. They thought it was just crackers.
Why would people reject that? It seems so obvious now.
This is true of so many things. When people say, “God, what an obvious idea that is.” Well, guess what? At the moment the original idea comes, it ain’t at all obvious. What is obvious now—online dating, electric bikes, the internet—it’s only later that people say, Oh, yeah, of course.
You’ve said qualified people with big prior positions are “mostly retreads.” Do you believe résumés are a good way to hire?
Résumés are almost all exactly the same. They’re promotional tools, so they’re all alike. The best companies are where you bring people in early and promote them.
Can you think of someone that you brought in from the outside that didn’t work?
Sure I can, but I’m not going to tell you.
Do you think some of the biggest jerks succeed because they trample everyone?
Sure they do.
In the mid ’90s when you lost the Paramount deal to Sumner Redstone, how did you move on?
We decided not to make our last bid, and when we lost to Sumner and I had to think of, All right, what am I going to say about that? And rather than do what most people do, which is go on about relative values or all sorts of stuff, that’s just babble. This is the only truth: They won. We lost. Next.
Diller bested most of his business rivals, although a
few—notably Sumner Redstone—outmaneuvered him.
Photo: Barry Diller
Tell me about your front-row seat in the early 2000s to media companies giving content away for free. Why didn’t people put up paywalls sooner?
At that time, it was perceived that the internet is free. That was the absolute governing rule: Paywalls couldn’t happen. Of course, over time it did happen, but all sorts of things had to take place before that was possible. You just cannot put your little fist up and say a technological improvement is going to be prevented by any law.
You start off the book saying you had a lack of emotional plumbing and end it saying you’re something resembling a person. What changed?
I got lucky. That is the word. Diane [von Furstenberg] and family forced me into emotional territory I had never prepared for before. Not that I wanted to, but I had no choice. Our family won’t permit any other behavior than complete emotional availability. You can’t hide. Everything is discussable.
Well, you certainly weren’t trained for that growing up.
I was thrown into that bath, and over time it warmed me. I’m now the result of it.
This interview has been edited and condensed for clarity.
Holly Peterson is a journalist and the author of six books, including the novels “The Manny” and “It Happens in the Hamptons.”