Jerry Weintraub: How to Use Creativity to Find Career and Business Success

Be the hero

Ayodeji Awosika
8 min readOct 7, 2021


How does a complete nobody get the opportunity to become Elvis Presley’s manager?

Jerry Weintraub was an ordinary man with extraordinary dreams. One of those dreams was to become Elvis’s road manager.

There were a few problems with his goal. One, Elvis already had a manager he’d been working with for years — the Colonel. Two, why would Elvis work with a random Joe Schmo of the street? Three, to be redundant on purpose — he was Elvis freaking Presley — literally the most famous person on the planet at the time.

None of this seemed to occur to Jerry.

He got a hold of the Colonel’s phone number and called him up.

“Who is this?”

“Hi, my name is Jerry Weintraub and I’d like to take Elvis Presley out on tour.”

The Colonel went on to explain that Elvis wouldn’t be going on tour any time soon or perhaps ever again. In his 60s, he’d transitioned to making movies. He also went on to explain that even if he were to go on tour, it wouldn’t be with some random guy.

This didn’t seem to shake Jerry at all. He called the next day with the same result. He also called the day after, and the next day, and the next day.

He called the Colonel every single day for a year. On day 365, Jerry found a way to wear the Colonel down, but the challenge was far from over.

How to Make a Million Dollars in 24 Hours

“Ok, you want to be Elvis’s manager? Meet us at the Hilton International Hotel with a million dollars cash tomorrow.”

Again, the ludicrousness of the task at hand didn’t occur to Jerry at all. He started thinking of ways to get the money. He called every bank in the city — a fool’s errand. After tapping out nearly all of his ideas and resources, he somehow found a way to get the money.

A local entrepreneur — and die-hard Elvis Presley fan — offered to give Jerry the money. Perhaps it was because an entrepreneur respected his audacity and was curious to see if he could pull it off.



Ayodeji Awosika

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