Until his death a couple of years ago, Jerry Weintraub was a legend (in his own time) in the entertainment business. The consummate showman, he promoted concerts (including Elvis Presley, Frank Sinatra, Aerosmith, Led Zeppelin, etc.) and produced movies (including Nashville, Diner, Ocean’s 11, 12, 13, The Karate Kid).

From Rich Cohen in Vanity Fair at the time of Weintraub’s death:

“He came out of New York in the early 60s with nothing but his wit and charm and wild desire to experience all life has to offer. He ended up with the fame and wealth and property and the rest of it, but mostly the man had friends. He knew everyone. He was everyone’s key guy. He was the guy behind the guy. He was the guy behind the guy behind the guy. And the guy behind that.

“The news of his death, at whatever age Jerry was claiming at the time – like his favorite kind of weather, it was usually somewhere in the high 70s to low 80s – comes as a great shock and a sick joke. There will never be another like him. It took the perfect parents in the perfect neighborhood at the perfect moment to create Jerry Weintraub. If you accompanied him on a verbal jag, you never forgot the voice. Yes, there were the flashing eyes and the broad shoulders and the big hands and the huge laugh and the oddly patrician grin, but mostly there was the voice. Funny, wise, sardonic, and warm, it got in your head and stayed there. Even now, when I’m about to cop out or give up or give in, I hear it: “Don’t be a schmuck. Keep going. It’s gonna be great.”

As is the case with most successful people, his backstory wasn’t all glamour and riches. He was a grinder, initially toiling in New York City with two partners and booking mostly second-tier entertainers into small venues. Eventually those two partners moved to Los Angeles and opened a west coast office. Weintraub followed them some time later. Fast forward.

Elvis Presley had spent the 1960s largely out of the public eye. He made records and films, but for eight years he made no concert appearances – NONE! Jerry had the bold idea to take Elvis on tour. He knew no one connected to Elvis but somehow managed to acquire the phone number of Colonel Tom Parker, Elvis’s legendary manager.

He called the Colonel and explained what he wanted to do. Parker listened and politely said “no thank you!” For the next YEAR, Weintraub called Colonel Parker EVERY DAY. Somehow he believed that eventually the Colonel would give in.

One day Jerry’s phone rang, and it was Parker. “You still want to take my boy on tour?” he asked. After getting off of the floor, Weintraub answered “of course.” Then Colonel Parker proceeded to tell Jerry that if he wanted to do it, he should show up in Las Vegas with a million dollars (when a million dollars was a ton of money) at a specific time – sort of a down payment. Jerry agreed but there was one big problem: He didn’t have a million dollars, and he knew no one who would give him the million, let alone within the tight time frame the Colonel demanded.

He got on the phone and called everyone he knew. No luck. Finally a friend in New York mentioned that he knew a guy in Seattle with a lot of money who also happened to be an Elvis fan. Jerry called him and after proposing the idea, the guy agreed to send him a million dollars. No contract; no guarantees; totally unsecured.

Weintraub asked the guy to wire a cashier’s check to a bank in Las Vegas made out to Elvis Presley but to his (Weintraub’s) attention. Jerry then drove to Las Vegas and on the prescribed day and time, he checked to see if the money had arrived; it had not. He then called Colonel Parker and asked for a bit more time. The Colonel agreed. The money arrived a short time later.

He delivered the check to the Colonel. They agreed to a 50/50 split on tour proceeds.

At the conclusion of the wildly successful tour, the Colonel and Jerry met in Parker’s hotel room to have a toast and debrief. Weintraub saw several suitcases and assumed they contained clothing. One at a time Parker emptied each on a large table. They contained cash. Lots of cash. Millions of dollars.

Weintraub inquired as to where the money came from. The Colonel said that this was the proceeds from the sale of tee shirts, key chains, programs, and other memorabilia.

Jerry had never seen that much cash and as he stared, the Colonel swung his cane over his head like an axe and swung it down through the money, dividing it in half with a theatrical gesture. He pushed one pile of money to one side, and the other pile to the other side. He then said that the money on one side was Jerry’s, and the money on the other side was his and Elvis’s.

He looked at Weintraub and said: “I know we didn’t discuss this, but we’re partners, and you should get half of everything.” That half was several million dollars.

At the beginning of the tour, Jerry was not a wealthy man. At the end, he was a multi-millionaire. His success fueled his confidence and ambition. He became one of the most successful impresarios in show business, managing talent, promoting concerts and producing movies. Quite a story, and quite a guy.

My questions for you: When was the last time you bet on yourself and took a big leap? Do you have a vision for your business and life that is big and bold, or are you content being just “OK?” Are you comfortable asking for help when you need it – financial or otherwise – or are you consumed by fear? Does the voice in your head (we all have one) speak to you in possibilities or limitations; with boisterous exuberance or timid whispers? Are you persistent, and do you persevere regardless of the obstacles in your way?

Copyright 2017 Rand Golletz. All rights reserved.

Author's Bio: 

Rand Golletz is the managing partner of Rand Golletz Performance Systems, a leadership development, executive coaching and consulting firm that works with senior corporate leaders and business owners on a wide range of issues, including interpersonal effectiveness, brand-building, sales management, strategy creation and implementation. For more information and to sign up for Rand's free newsletter, The Real Deal, visit http://www.randgolletz.com