How to Ask George Clooney for Advice

As a co-chairman of Creative Artists Agency, Hollywood’s most prestigious talent-representation firm, Mr. Lourd helps shepherd the careers of

Brad Pitt,

Scarlett Johansson,

Lady Gaga,

Lorne Michaels

and many more actors, writers and directors. As one of the agency’s leaders, he oversees a staff of nearly 2,000 that does the same. It’s a job that comes with several traditions (a start in the mailroom, for one) and a credo: Everything is about the client. Their desires, their needs, their hopes and dreams—a cocktail of demands that requires some hard-won emotional intelligence.

“All of the dysfunction in my life made me great at this job,” he jokes. “I don’t know anyone who came from a supernormal home or town who’s great at this job.”

Since 1995, he has managed CAA alongside his fellow partners, leading during a period of expansion beyond traditional film and TV representation to clients in sports (

Joel Embiid

), politics (

Beto O’Rourke

) and digital media (vegan TikTok influencer

Tabitha Brown

). If there is a star, politician or boldfaced name in the news, chances are Mr. Lourd is doing some kind of business with them, or can find you the cellphone number of the person who is. While CAA has avoided some of the big-ticket acquisitions of its main rival,

Endeavor Group Holdings Inc.,

its business in recent years has expanded to include investing in other companies and corporate pursuits.

It’s fitting for someone who has always been interested in entertainment in its many guises. As a 17-year-old during the 1970s in New Iberia, La., Mr. Lourd and two friends, fortified by youth and an eight-pack of Miller ponies, re-erected a 30-foot-tall Christmas tree that had fallen on the city hall lawn, enlisting police officers in an effort that ended in carol singing and a feel-good newspaper write-up—his first press clipping.

“There’s nothing to do in this town after 11 o’clock,” he explained to an Associated Press reporter at the time. He left for Southern California soon after.

In Mr. Lourd’s years running CAA, the business has changed—and with it, those to whom he turns for advice. Running a talent firm today means staying up on the latest trends and watching rivals gobble up assets. That’s made him more dependent on people from the world of finance to assess acquisition opportunities and to “shape things that we’ve done and more importantly, not done,” he said.

That is, when the tables have turned and he’s the one asking for advice. Before he does so, he tries to make it as easy as possible for the person whose help he is seeking, organizing his thoughts to avoid taking up time with tangents.

He says: “These are the choices I see in front of me. Here are the pros and cons. What’s your opinion?”

These are four people to whom Mr. Lourd poses that question.

Larry Auerbach

Retired talent agent

Mr. Lourd got his start working as the assistant to Mr. Auerbach, then an agent at the William Morris agency who booked

Elvis Presley’s

first network-television appearance and oversaw a client roster that included

Bea Arthur

and

Bill Cosby.

He arrived at 6 a.m. daily, ready for a full schedule of calls and washing coffee mugs.

As most agent assistants do, Mr. Lourd would listen to his boss’s calls and take notes, getting a crash course in the art of managing talent. “He was a translator,” Mr. Lourd said. For instance, he explained, there are these crucial definitions in Hollywood:

“Yes” means “definitely.”

“Maybe” means “I’m never going to do that, but I’ll just say that to get off the phone.”

“No” means “Sometimes a real no. Sometimes, ‘Tell me more.’ ”

Another education came from the homework his boss would assign in between those calls.

Mr. Auerbach would send Mr. Lourd down to the basement file room, teeming with old contracts dating back to its start in the silent era. Mr. Lourd would study the deals that had put

Marilyn Monroe

and Mr. Presley into the movies.

“Read this file and talk to me about it. Ask me questions,” Mr. Auerbach would tell Mr. Lourd. The two men still try to see each other once a month.

Martin Lipton

Founding partner at Wachtell, Lipton, Rosen & Katz law firm

In 1995, Mr. Lourd and his colleagues were blindsided when

Michael Ovitz,

a CAA co-founder, left to become president of Walt Disney Co. Mr. Lourd and four colleagues took over—and soon learned that running an agency was more complicated than simply managing a talent list.

“We had never run anything,” said Mr. Lourd.

In those first hours in charge, Mr. Lourd started casting about for an attorney to help navigate the ownership shift, asking friends, “Who will

Mike Ovitz

be afraid of?”

There was only one problem with the names they offered: They had affiliations with Mr. Ovitz that made them impossible to hire. Mr. Ovitz did not respond to a request for comment.

He finally got in touch with Mr. Lipton, a New York lawyer who was vacationing with his family in San Diego but drove up to Los Angeles soon after the call. Mr. Lipton became an indispensable source of guidance on logistics, taxes and the other business-related details of running a company.

Together they hashed out the ownership deal that gave CAA to Mr. Lourd and the other so-called “Young Turks” now in charge—a case study in an adviser relationship forming at a moment of crisis.

“He’s still our lawyer,” said Mr. Lourd.

Barry Diller

Chairman of IAC/InterActive Corp.

Mr. Lourd met Mr. Diller, a longtime media mogul, early in his career and became friends with him. Since then, they’ve done some business together—Mr. Lourd serves on the IAC board—but Mr. Diller functions more as an observe-and-absorb kind of mentor, especially when it comes to staying relevant in an industry obsessed with the newest thing.

“He’s the most active, most in-the-world person I know,” Mr. Lourd said of the 79-year-old Mr. Diller.

From watching Mr. Diller, he has learned how to better spend his time. “There’s zero he doesn’t do or want to do,” said Mr. Lourd.

That has come in handy as Mr. Lourd has navigated a shifting Hollywood, one that requires him to be versatile in entertainment far different than the studio releases and syndicated shows that defined his early career. He recently acquainted himself—or tried to—with nonfungible tokens, or NFTs.

In Mr. Diller, he has a friend whose senior years have included overseeing several dating apps like OkCupid and Tinder, along with other digital ventures, as well as taking daily swims.

“He’s the youngest person I know,” said Mr. Lourd.

George Clooney

Actor

Mr. Lourd recently caught up with Mr. Clooney, getting updates from England on a script he’d just finished. Despite his reluctance to ask others for advice, he considers Mr. Clooney—a longstanding client—to be a fantastic sounding board.

“I trust his judgment completely,” said Mr. Lourd. “There’s nothing he’s not curious about.”

Mr. Lourd says Mr. Clooney is an example of a client who picks projects that reflect both his personal interests and developments in the broader culture.

“People who work at our company are only at their best when they know a lot about a lot of things and aren’t just deal makers,” he said. “My view on things is constantly reshaped and refocused and informed.”

But Mr. Lourd is in no hurry to chase fame himself. After a recent workout with his daughter, “American Horror Story” actress

Billie Lourd,

the pair was photographed by paparazzi.

“Billie Lourd shows off her post-pregnancy figure after a gym workout,” read the caption in the New York Post. Mr. Lourd, also in the frame, wasn’t identified.

“It was great,” he said.

Write to Erich Schwartzel at [email protected]