Lessons in Success from a Hollywood Big Shot

Photo by Jake Blucker on Unsplash

What is common between Elvis Presley, Frank Sinatra and John Denver?

Or how about the movies Ocean’s 11/12/13 and The Karate Kid?


Here’s the answer: Jerry Weintraub (pronounced wine-trawb).

It’s ok if you’ve never heard this name before because his wasn’t a face you would see on posters or on TV. But in his career spanning five decades, Weintraub had a hand in crafting the success of people who did become known around the world.

As a talent agent, events promoter and movie producer, Weintraub launched countless careers, put together memorable spectacles and created some iconic movies. In a way, he was like the Elon Musk of show business: from live music to Broadway, film and TV, this man did it all.

At a time when success is studied like it’s a science, Weintraub’s story matters because it proves that it’s not all that complicated. Grit, persistence and the ability to build relationships is all there is to it. When you do this mixture right, even luck has no option but to find you.

Weintraub did not possess superhuman intelligence, nor did he come from a moneyed background. What he did have, however, was the willingness to keep pushing beyond his comfort zone. He never settled and kept looking for the next big opportunity. His biggest quality was trusting himself to make any situation work, even if he didn’t have a clue about what was going on.

Weintraub’s passed away in 2015, leaving behind not only an awesome list of achievements but also valuable lessons on how to succeed at life. Here are seven of them to inspire and motivate you.

Lesson 1: Packaging matters. A lot.

‘It’s not the gem a person buys. It’s the story behind the gem. It’s the romance.’

The best example of this strategy was how Weintraub helped turn John Denver from a folk singer into a chart-topping star. Convinced of Denver’s immense talent and appeal, he packaged the singer as someone who was already famous. Plastering Denver’s face on huge billboards everywhere, he made people believe that they already knew him. As he wrote:

‘I sold him in the past tense, as someone you’ve known about for years. I was telling the audience to relax and enjoy, as the judgment has already been made.’

When newer audiences finally heard the songs, they didn’t feel like they were listening to a new singer. They had already fallen for the phenomenon that was John Denver.

Humans have an inherent tendency to frame the world in the form of stories. Packaging your work is not just about telling the world you exist. It’s about giving people a story that they can get invested in. The lesson: you might have all the talent in the world, but it might not amount to anything if you can’t sell your story.

Lesson 2: Relationships are the most important thing

Weintraub’s life was proof that nobody succeeds alone. Performance obviously matters, but networks matter even more. He quotes in the book:

‘You might have a great pitch, but unless you can get your foot in the door, you can’t make that pitch.’

And the best way to open doors is to know somebody on the inside. This might seem unfair, but this is simply how the world works. Most people just prefer to work with people they know. In fact, trust and familiarity are such powerful forces that they can even make up for small deficiencies in ability. As the First Law of Success proclaims: Performance matters, but networks matter more. So get out there and make some friends. (Link to law of success)

Lesson 3: “Be willing to be lucky”

He had originally fumbled his way into a job there by hoping to learn the required skills — typing and shorthand — on the fly. When found out, he simply admitted his shortcomings. But by that time, he had already impressed his bosses with his attitude and work ethic. So rather than punish him, they promoted him to junior agent with an increased salary! And just like that, he landed a job he was always aiming at.

Most people think that luck is like lightning: you never know where it’s going to hit. But if your intention is to be hit by lightning, you have to be out in the field when a storm approaches. In other words, you have to make it easier for luck to find you.

Lesson 4: Pretend like you can’t hear the word ‘no’

Weintraub was already a fairly successful promoter when he hatched the idea of working with Presley. But he wasn’t yet in the top leagues. So when he called Colonel Parker, Presley’s legendary manager, to pitch him the idea he was immediately turned down. Not once, not twice, but over several months. But Weintraub was not one to back down. In his own words:

‘When people say , “No”, I don’t hear it.

When people say, “That’s a bad idea,”, I don’t believe them.

When people say, “It won’t happen,”, I pretend they’re joking.’

It was almost a year later that Colonel Parker finally relented and gave Weintraub his chance. Just let that sink in. A year of outright rejections and being told you had no chance; most people would have wilted just after the first few tries.

Persistence is a considered a cliche because people don’t want to be reminded that success is a brutal slog. Talent, hard work and luck all play a role, yes. But more often than not it’s simply a matter of staying on your feet while everyone else leaves the field.

Lesson 5: When stuck, reframe the problem

This wasn’t really a problem except when they decided to do two shows in a day at Miami beach. While the evening show was completely sold out, the afternoon slot was left with 5,000 unsold tickets. Disaster.

Fearing the worst, Weintraub thought on his feet and came up with an ingenious plan. He recruited prisoners from a nearby jail to unscrew the unsold seats, pile them up in the parking lot and cover them up with blue tarp. Come night time, the seats were screwed back in, with Elvis none the wiser.

When things go south — as they inevitably will some time or the other — your earlier assumptions might not apply anymore. At such times, try to frame the problem differently. Remind yourself of the end objective and ask if there is another way to get there. As Weintraub showed, ‘no empty seats’ doesn’t always mean ‘100% tickets sold’.

Lesson 6: “Life is too short to be working with morons”

‘Work with the best people. If you have the best writers, the best actors, and the best director and fail, okay, fine, there is something noble in it; but if you fail with garbage, then you are left with nothing to hang your spirits on.’

Realize that you have limited time and resources. Do not waste them with people who can’t push you to become better. Obviously don’t be a jerk, but demand the best for yourself.

Lesson 7: Never stop learning

As he quotes in the book:

‘There are three key words in business: I don’t know.’

It’s a well-worn trope that as you get older and more successful, you stop learning and taking chances. You feel you’ve made it and settle into a life of comfortable mediocrity. Weintraub showed what is possible when you stay curious and are unafraid fail.

The concluding lines from his memoir perfectly capture Weintraub’s approach towards life:

‘I asked if I did not know.

I listened when someone else was talking…

Most important, I was never afraid to fail, which meant I was never afraid to try.

I was never afraid to look silly, which mean I was never threatened by a new idea.’

And that, ladies and gentlemen, is how show-business moguls are made.

I read like a man possessed | I write to understand the world | Twitter: @DhawalHelix

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