How To Become Hollywood's Most Persuasive Man

Once in a while you read a biography that changes you. It pushes you to think different, inspires you and reveals a bit more about your path.

You never know when it’s going to happen (which makes it fun when it does).  

I found a biography last year, that I’ve read 4 times (it’s that good). Each time pulling out new lessons and applying them to my life. 

Today, I’m going to share those ideas. 

This article is a series of lessons learned from Hollywood's greatest promoter and biggest dealmaker. He’s the man behind Elvis Presley, Frank Sinatra, Bob Dylan, John Denver, The Ocean’s 11 Franchise, The Karate Kid and many more. 

Jerry Weintraub His Way When I Stop Talking You'll Know I'm Dead

No matter what life threw at him from club rooms of Brooklyn, to Mafia hangouts of NY’s Lower East side, to the hills of Hollywood he found a way to promote and sell tickets to his shows. 

"All life was a theater and I wanted to put it up on a stage," he writes. "I wanted to set the world under a marquee that read: 'Jerry Weintraub Presents.’ 

Jerry Weintraub is the most persuasive man in the history of showbiz. His biography 'When I Stop Talking, You’ll Know I’m Dead' tells his rise obscurity to entertainment millionaire super-mogul. It’s one of my favorite books and reads like a master's class of case studies in building a successful career. 

In this article I break down the top things we can learn from his story, the lessons learned and how we can apply these lessons to our lives.

If you are on the path towards greatness, this article is for you. 

Here are the lessons I learned from When I stop Talking You’ll Know I’m Dead. 

Lesson #1: Be Persistent (extremely)

It was stupid. It was nuts. Everyone told him it couldn’t be done. Even his wife told him to move on. 

But the idea wouldn’t go away…. 

He wanted to take Elvis Presley (the biggest star in the world) on the road and do a concert tour. This was before the sun-god jumpsuits, cocaine, Fool’s Gold Loaf’s and fat Elvis. 

Elvis Jerry Weintraub Stop Start Do

Presley was in his prime and everyone wanted a piece of the action. If there was a center of the universe, Elvis was it.  

Jerry's idea was crazy and there were many problems right from the start.

  1. At the time, Elvis did not do concert tours (problem).
  2. Jerry did not have a connection to Elvis (bigger problem). 
  3. He needed $1,000,000 to start the conversation (massive problem)
  4. He didn’t have a proven track record of taking big acts on the road (most people would give up here). 
  5. All roads to Elvis lead through his notorious and “hard to deal with” manager the Colonel Tom Parker (the biggest problem of all). 

Instead of whining about his circumstances, he picked up the phone and started pitching the Colonel. 

The answer was a firm NO.

So he called back again the next day. Again the same answer. 

I started to call… every morning at 8:30 in the morning. He was always up at 6:00 oclock in the morning. I used to call him every morning, ‘Good morning, Colonel, this is Jerry Weintraub. I want to take Elvis on tour.’

And every morning he said to me, ‘What are you, you’re crazy. Why do you keep calling here? You’re wasting your money’.

Jerry kept calling. Every day for an entire year. He was rejected. Over and over. “No” after “no”. More than 365 times. But he kept asking. 

How many times would you have asked?

The persistence finally paid off and he wore down the Colonel. One morning when he called, the conversation went like this. 

You still want to take my boy on tour’. I said, ‘Yes’. He said, ‘Okay, you be in Vegas tomorrow at 11:00 o’clock with a million dollars and we’ll talk a deal

Jerry needed one million dollars fast. He didn’t have the money (was in debt) and needed it by tomorrow. No second chances.

Again Jerry pounded the phones, getting rejected by everyone. Finally at 8:30 AM the following day, he was able to reach an investor willing to put up the cash. An equally crazy radio mogul from Seattle. 

With no time for contracts Jerry convinced him over the phone and the money was wired in. He went to Vegas and handed over the check. 

Deal closed. 

In 24 hours he had launched his career into superstardom. From obscurity to promoting the biggest act in the world. Skipping all the middle steps.  


Your Takeaway:

How many times would you have faced rejection? How persistent would you have been?

Hell... most of us give up when we face small obstacles. I know people who look for roadblocks so that they have an excuse NOT take action. One of my buddies won’t lose the extra 40lbs because he doesn’t want to get rid of the junk food in his cabinet. He thinks it would be a waste.  

Persistence is the most underrated factor in success and most of us give up at the first “No”. Were afraid of causing tension, facing rejection, or temporary pain associated with taking action. It’s like jumping in a cold pool. It’s uncomfortable at first, then you get used to it. 

You get comfortable asking for what you want and going after it. You get comfortable causing some tension and facing rejection. You get comfortable doing the work that others are uncomfortable doing. You get comfortable being persistent and blasting though resistance.

Where have you let roadblocks get in the way? And where can you be more persistent?


Lesson #2: Have a visceral (deep) connection to your work

As a child growing up in New York Jerry Wanted to be in showbiz. The stars, movies, bright lights and adventure created deep connection for him. It felt right. He couldn’t explain it. 

Each time he went to the movies it was like a religious experience for him.  While everyone fantasized about what their life would be like if they were in the movies, he visualized (there’s a difference). While others fantasized, he started scheming. 

It was his calling. His ONE THING. Everything else became a means to an end. 

This deep rooted connection to entertainment stuck with him during his entire career. It gave him the willpower to push through the BS and nonsense that accompanies working with stars. Like when the drummer of Led Zeppelin stole his $2,000 custom suit, ripped off the sleeves (while mocking him) and wore it during a show. 

While most of his peers quit, he stayed put. Finding ways to keep his work fresh, searching for new mountains to climb and novel adventures to be had. 

Your path to mastery must include this connection to your work.


Your takeaway: 

This is not easy for us. We don’t stick with ONE thing long enough to create a connection. 

Yet when you study success, you find all masters have this connection to their work. Da Vinci, Jobs, Gates, Branson, Musk, Picasso, Jordan and Mozart each displayed this obsession. Jerry Weintraub was the same way.   

But here’s the problem: We live in a world of unlimited choice. Even picking out almond butter at the grocery store I’m faced with 17 options. Raw crunchy, Raw Creamy, Salted Crunchy, Salted Creamy, Unsalted Creamy, Unsalted Crunchy etc. Why the hell are there so many choices? What if I pick the wrong one?

The key is to pick one industry that suits our unique strengths. And then stick with it long enough to become a master. Passion, motivation and innovation come after you have put in the time. Not before. 

Lesson #3: Visualize The End

10:00 AM on top of a roof of a Vegas casino Frank Sinatra was laid out. Drunk. Despondent. High. And ready to end it all. 

It was over for him. No mountain to climb. No challenge to accomplish. A bull rider without a bull. 

He needed hope and had none. So he called Jerry over and they started talking.

The conversation went like this:

‘What’s the matter with you?! What are you doing?’

He said, “I’m bored. I can’t go down and do the same songs every night.”

Jerry didn’t know how to fix his problem, but he had a vision. It was coming into focus.

New York. Madison Square Garden. Screaming fans. A boxing ring. Frank Sinatra. Live TV. No practice. Thousands in the audience. Millions watching at home. 

Jerry started talking. Without anything pre-planned, he pitched Sinatra as the vision appeared, improvising on the spot. He watched Sinatra’s reaction making sure his words hit. 

I said, “Listen, Frank, we’re going to do a concert live around the world from Madison Square Garden. And we’re going to do it in a boxing ring!” I don’t know where the hell that came from, it just – Madison Square Garden! Sinatra! Jerry Weintraub! Boxing! And we did it and it was his greatest concert.
Frank Sinatra The Main Event Jerry Weintraub

After selling him on the vision. He had to do was figure out the logistics. Months of planning, preparation, organization went into the TV spectacle of the decade.

From that initial vision on the rooftop in Vegas, he made it a reality. 


Your Takeaway:

We know all great masters had very visual minds such as Einstein’s famous thought experiments. They were able to see what others couldn't and visualized their end goals. 

Most people don’t know what they want and they can’t picture it. You ask them and they say
I’m just figuring it out”
“not sure yet”
“I don’t know”

It’s not that they “don’t know”. They just haven’t put in the time to figure it out. 

To get anywhere, first you need an end point. Imagine flying a plane without a destination. Yet that’s what most of us are doing. We spend our time aimlessly passing through life walking around in a daze. Spending our nights watching Netflix, when life is passing us by.

The key is deciding your end goal. Now you have a target to aim for and can start working towards it. If it turns out to be the wrong target/goal, you can always change.

Jerry had a clear vision of what he wanted out of life and in each project. Because he saw it so clear he was able to make it happen. If he was wrong, he changed. Jerry saw what he wanted and then made it a reality. 

He was able to visualize the end goal and then will them into existence. We can do the same in our lives and projects.


Lessons Learned

When successful people like Jerry Weintraub are in the winter of their lives and share their wisdom, we should listen. Especially those of us in the spring and summer of our lives.

There are many lessons that you and I can take away from Jerry’s life story. And once again, here are the big 3 I took away:

  1. Be persistent
  2. Have a visceral connection to your work
  3. Visualize your goals

Read the book. Learn the lessons and continue on your path. 



[1] Weintraub, J., & Cohen, R. (2010). When I stop talking, you'll know I'm dead: Useful stories from a persuasive man. New York: Twelve.

[2] Interview with Jerry Weintraub - Elvis Concert Promoter. (n.d.). Retrieved July 1, 2015, from

[3] Jerry Weintraub: How I Snookered Elvis Presley, Saved Sinatra. (2011, November 1). Retrieved July 1, 2015, from


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