Lessons from the world’s most beloved CEO

The Executive Summary
Executive Summaries
3 min readAug 12, 2020

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“Don’t be in the business of playing it safe. Be in the business of creating opportunities for greatness.”

“I’m going to tell you something that only my wife and my Doctors know. And I need your complete confidentiality — my cancer is back.”

How would you react to this sort of devastating news from a friend? Would your reaction change if that person was a business partner? How about if they were both? Now, let’s say that they are both a friend, a business partner AND they’re telling you this news less than 30 minutes before the announcement of a $7.4B acquisition that you’d been working on for months. What would you do?

You are Robert (Bob) Iger, the CEO of the Walt Disney Company. Your friend is Steve Jobs, the CEO of Apple, and the founder of Pixar. With Disney’s acquisition of Pixar just minutes away, Steve is about to become the largest single shareholder in the history of the Walt Disney Company. He’s about to take a seat amongst the elites as a member of your board, knowing that his time and health are limited.

What would be the right thing to do in this situation?

Disclose this information to the board?

Call off the acquisition?

Throw Steve under the bus and hope that eventually your board gets over it?

Or maybe tell the board that you’ve got cold feet and take the attention away from the terrible news?

In the reality of this situation, Bob Iger navigated an extremely difficult professional and personal situation with the grace that you’d expect from a man worth $690M.

The Ride of a Lifetime is a captivating memoir that highlights the accomplishments and lessons learned from one of the world’s greatest professionals and the most forward-thinking leader that Disney has ever had. I didn’t realize how many pillars of entertainment in our world today have Bob Iger’s fingerprints all over them. The resurgence of Disney animation, the bond between Disney and Pixar, the birth of the Marvel Cinematic Universe as the most successful movie franchise, Star Wars, and so many more. The takeaways from Iger’s experience are just as hypnotic as the detailed stories that he tells in the book. Stories about his time working for ABC as a young man, running errands for Frank Sinatra, his first time meeting Steve Jobs, conversations with Ryan Coogler before Black Panther, dealing with a tragedy at Disney World in Orlando while opening a new resort in Shanghai. Through his writing, you’re able to experience the weight of holding such a powerful position, while feeling empathetic towards the sheer magnitude of the responsibility.

The Ride of a Lifetime is a must-read for all but especially for current and aspiring leaders. Iger wraps up his gift of a novel with a full Appendix of lessons to lead by that are the perfect balance between concrete, prescriptive thoughts, and deliberately vague philosophical ideas,

Here are some of my favorites:

“Now more than ever, innovate or die. There can be no innovation if you operate out of fear of the new.”

“Be decent to people. Treat everyone with fairness and empathy.”

“Excellence and fairness don’t have to be mutually exclusive.”

“Managing creativity is an art, not a science. When giving notes, be mindful of how much of themselves the person you’re speaking to has poured into the project. Don’t start negatively and don’t start small. If you start petty, you seem petty.”

“If you want innovation, you need to grant permission to fail.”

“Don’t be in the business of playing it safe. Be in the business of creating opportunities for greatness.”

What I enjoyed the most about this book is the way Iger communicates a successful brand of leadership with such humility. Many times we expect the most successful leaders in our world to be outspoken, or have a certain ‘asshole’ quality. Iger is the exact opposite of that; being able to challenge people to a level of excellence while also maintaining integrity and fairness.

If you’re looking for a way to embody leadership qualities that will set you apart, pick up The Ride of a Lifetime.

This Executive Summary was contributed by David Oladejo.

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