The defining project of Jerry Weintraub’s life came to him in a dream.
In it, the marquee of Madison Square Garden read: Jerry Weintraub Presents Elvis Presley. Of course, when Jerry told his wife the next morning he wanted to take Elvis Presley on the road, she told him he was crazy. He didn’t even know Elvis.
At this point Weintraub was already a successful player in showbiz, running his artist management firm, Management Three, with Bernie Brillstein and Marty Kummer. His was a classic rags-to-riches Hollywood story: born in the Bronx, started in the mailroom at Lew Wasserman’s MCA agency, later becoming Wasserman’s assistant, and then going out on his own to carve his path in Hollywood.
Even though he managed artists like Jackson Browne, Jimmy Buffett, and his wife, Jane Morgan, Weintraub was delusional to think he could convince Colonel Parker, Presley’s prickly manager, to take Elvis on his first national tour. The idea was an insult to pipe dreams.
Elvis had spent most of the 1960s acting in films and making soundtracks for them. He’d been largely been written off as a serious musician and Elvis himself questioned whether he had the chops to perform again until he famously killed it in his 1968 Comeback Special on NBC—his first live performance since 1961.
But Jerry literally had a dream, and so he called Colonel Parker and pitched him on the tour. Of course, the Colonel shut him down. Elvis hadn’t been on tour in years, and he wasn’t about to start now. And when that time came, the Colonel would have his pick of the best people in the entertainment world for the gig.
Undeterred, Weintraub would call Colonel Parker every day for at least a year, hoping that if the Colonel did decide to take Elvis on the road, Jerry Weintraub would be the first name the Colonel thought of.
Then one morning, the phone rang. It was the Colonel. He wanted to know if Jerry still wanted to take his boy out on the road. After Jerry said yes, the Colonel gave him his terms: deliver $1 million to him at the roulette table at the Hilton International Hotel in Vegas by tomorrow.
Imagine finally getting the deal, after persisting in the face of ridiculous odds and daily rejection, only to be hit with terms you couldn’t possibly meet. There’s a Haitian proverb, “Beyond the mountains, there are more mountains.” While Jerry had reached one summit, it revealed another one he’d have 24 hours to climb.
At the time, Weintraub didn’t have anything close to a million dollars, which was a lot of money back then. So he did what he did best: got on the phone. He called everyone he knew, hoping someone knew someone who could help him pony up the cash.
Late into the night, a friend returned his call. There was a guy named Lester Smith who owned a lot of radio stations and was a huge Elvis fan, he might be willing to front Jerry the money. He called Smith and made the pitch of his life. Lester Smith clearly loved Elvis because he agreed to the deal without signing a contract or even meeting Weintraub. There simply wasn’t time.
Jerry landed in Vegas the next morning and delivered a cashiers check to the Colonel for $1million. Jerry Weintraub was a 26-year-old talent manager and he would return from Elvis’s first national tour a millionaire. Because of Elvis’s successful tour, Weintraub would later run tours for Frank Sinatra, Bob Dylan, Led Zeppelin, and John Denver. Later in life, he became a movie producer with hits like Nashville, Diner, The Karate Kid, and Oceans 11.
Weintraub would write in his memoir, When I Stop Talking You’ll Know I’m Dead: “When the man says no, pretend you can’t hear him. Look confused, stammer, say, ‘Huh?’ Persistence—it’s a cliche, but it happens to work.” How many times have we quit after a single rejection? Or failed followed up on an email after not getting a response? Or not even reached out for fear of being rejected?
Colonel Parker rejected Jerry Weintraub so many times that when Elvis was ready for the road, he remembered Weintraub’s name. After learning of Weintraub’s persistence first hand during the Oceans films, George Clooney called him a hurricane, a force of nature that could not be stopped. Too often we worry about hearing “No”, bugging busy people, or looking pushy when going for something we really want. It’s during these apprehensive moments, we’d do well to remember Jerry Weintraub, the hurricane that could move mountains.
Get two stories like this every month in your inbox by signing up at this link for the Profiles in Action Newsletter. Each one comes with further recommended reading based on my research, including books, articles, and interviews with the subject. Use the lessons within to get unstuck, keep plugging along, or do that thing you’ve always wanted to do.
This was previously published on Medium.