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Hollywood Producer ‘Jerry Weintraub’ – The Top 5 Ways To Sell Ice To An Eskimo

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Elvis Presley, Frank Sinatra, George Clooney, Brad Pitt, Matt Damon — none of them would have reached the summits they did if it weren’t for the efforts of uber-producer Jerry Weintraub. To say he could sell ice to an Eskimo is a gross understatement. The kid from the Bronx without a college degree didn’t just take Hollywood by storm, but the entire world — and he’s finally selling the secrets of his incredible powers of persuasion in a new book, When I Stop Talking, You’ll Know I’m Dead — Useful Stories from a Persuasive Man.

Read on for Jerry Weintraubs 5 Tips On The Art Of Persuasion.

Jerry Weintraub’s 5 Tips On The Art of Persuasion:

1. Be persistent.

Do not hear the word no. Almost every time I have a new idea, someone says, “No, that will never work.” But to me, “no” is just an opportunity to convince someone to say “yes.” When you hear “no,” you say “What? Say that again, I didn’t catch that.” If someone says “Get lost,” you say, “Go where?” Keep knocking, keep pitching, and the door will open for you.

2. Have conviction.

Act as if the result you want has already been achieved. When I first signed John Denver he had only one genuine hit, but I still called his next record John Denver’s Greatest Hits, making it seem to the public as if he was already a star, like they’d known his music forever. They already loved him — they always had. I knew Denver was a star; I could feel it, and I believed it. And the rest is history.

 

3. Respect yourself.

This is key. If you respect yourself, you will be treated with respect. Consider my relationship with the great Chicago power broker Arthur Wirtz. Wirtz was a huge man, 6-foot-6, all power, a very intimidating guy. When I first went to meet him, he made me wait outside his office for hours. He did not even look up when I finally walked in, just sat at his desk signing checks. Then, from the side of his mouth, he said, “Yeah, what d’ya want?” So you know what I said? I said “[bleep] you!” Why? Because he was not treating me with respect. He looked up at me and smiled. I was no longer one of the thousands of faceless nobodies asking him for a favor, but an individual. After that, we forged a relationship that lasted for years.

4. Be creative.

Think your way around problems, come up with novel solutions, improvise. If you think you have failed, you simply haven’t thought hard enough. As an example, watch the animated video here about the first show I did with Elvis. I had 5,000 unsold seats in a 10,000 seat arena with only hours until showtime. Big problem. I was never going to find enough people to fill the seats. But I quickly realized a solution: not more people, but fewer seats. 5,000 to be exact, unscrewed from the floor and carried out the door. Voila. No more empty seats.

5. Go nuts.

I don’t mean go crazy, I mean reach for the moon. Most people think that if it hasn’t been done, it can’t be done. But if it hasn’t been done, that probably just means it hasn’t been tried. This is the story of my life, the kid who tries what no one thought to try before: putting on concert tours in sports stadiums, selling the greatest hits of an artist that has only one hit, having the greatest singer in the world (Sinatra) perform in a boxing ring in the heart of New York City. Listen to me: It is OK to fail. Fail and fail, again and again. You learn by failing. And if you fail 10 times for every one success, then why not fail a thousand times? It will make your success into a legend.

Below is a trailer of Jerrys new Documentary, get your hands on this and learn how Jerry became a legendary man of persuasion in one of the hardest industries to crack.

 

Jerry Weintraub – ‘His Way’ Explores The Life Of A Hollywood Producer

I am the the Founder of Addicted2Success.com and I am so grateful you're here to be part of this awesome community. I love connecting with people who have a passion for Entrepreneurship, Self Development & Achieving Success. I started this website with the intention of educating and inspiring likeminded people to always strive for success no matter what their circumstances. I'm proud to say through my podcast and through this website we have impacted over 200 million lives in the last 10 years.

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Success Advice

Why One-Size-Fits-All Leadership Will Always Fail (and What Works Instead)

The surprising truth about leadership styles that can make or break your team’s success.

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Why one-size-fits-all leadership doesn’t work
Image Credit: Midjourney

Leadership has always been as much about people as it is about performance. Ken Blanchard, in his influential book, “The One Minute Manager”, put it simply: different strokes for different folks. (more…)

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Success Advice

What Every New CEO Must Do in Their First 100 Days (or Risk Failure)

Your first 100 days as CEO could define your entire legacy, here’s how to make every move count

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leadership tips for new CEO
Image Credit: Midjourney

When Tim Cook took over from Steve Jobs at Apple, the world watched with bated breath. Jobs wasn’t just a CEO; he was a visionary, an icon, and a legend of innovative leadership. (more…)

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Entrepreneurs

The Leadership Shift Every Company Needs in 2025

Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

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Bridging the gap between employees and employers
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In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.

What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

  • Build diverse talent pipelines

  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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Entrepreneurs

What Makes an Entrepreneurial Leader? Traits of the World’s Best Innovators

Inside the mindset of entrepreneurial leaders who transform risk, passion, and vision into world-changing results.

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entrepreneurial leadership skills and traits
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When you think of Richard Branson (Virgin Group), Bill Gates (Microsoft), Steve Jobs (Apple), Rupert Murdoch (News Corporation), and Ted Turner (CNN), one thing becomes clear: they are not just entrepreneurs, they are entrepreneurial leaders. (more…)

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