The Ride of a Lifetime

The Ride of a Lifetime

I originally picked up The Ride of a Lifetime by Bob Iger not really knowing what to think. It's Iger's memoir recalling stories and memories from the past 15 years as the CEO of Disney.

I'd heard good things about the book, and have generally been impressed by Disney's trajectory, but I don't exactly have a passion for media companies. Nonetheless, I'd highly recommend this book. It's entertaining, funny, well-written, and chock-full of good leadership stories. It made me reflect on my own experiences at Segment, and revisit times when I could've been a better leader by employing these lessons.

Public CEO Life

Bob opens with a pretty incredible account of one week as CEO of Disney. It involves the opening of their biggest resort in Shanghai (a $5b project), the shooting at the Pulse Nightclub in Orlando (Disney World was supposed to be the target), and the killing of a 2-year old boy at Disney World.

Throughout it all, he has to continue to present a brave face, give a speech partially in Mandarin, all while being under extreme emotional duress. Each new problem is completely unexpected, and requires world-class levels of context-switching and compartmentalizing.

I was also struck by how much Bob relies on his team day-to-day. It might be different to actually work with him, but Bob really does seem to channel Disney's success as a result of a team effort, rather than any sort of individual work.

Traits of a good leader

Optimism – a good leader has to be optimistic. They have to believe that things will get better with hard work and focus. Bob phrased this as "each day there will be some new problem, and I have to decide how to fix it".

Decisiveness – a good leader needs to make decisions. Indeed, Bob's career seems to be framed by making hard decisions at the right time, where his predecessors do not.

Courage – Bob holds a pretty strong belief that companies must "innovate or die". To do so takes courage, and often requires you to give up on an existing business so that a better one will thrive. It struck me as very Amazonian.

Authenticity – a great leader must have a clear idea of both what's right and wrong, and operate on those principles. They must be clear and consistent in their messaging. Having this internal compass allows you to build the company in the way you want, and not be swayed by shortcuts.

Know what you don't know – this dovetails with authenticity, but it's perfectly okay to say "I don't know." Bob learned this from his first "station manager" at ABC, who was well-aware of times when he didn't have the answers.

Thoughtfulness – Bob says a good leader must "do the homework". You should take time to develop informed opinions. If you don't, you're going to make snap judgements which will erode your credibility.

The Relentless Pursuit of Perfection – a great leader should constantly be trying to achieve perfection. That doesn't mean being a perfectionist! But it does mean constantly trying to deliver a higher level of quality, and to build great things.

Hard work – Bob's motto is "Always say yes" to an opportunity. I'm struck throughout the book by how many times Bob didn't know how to do something, but said yes to it and tried to figure it out on the job. It's a good reminder to take bets on people. With hard work, they will often succeed

Instilling an Entrepreneurial Spirit

When Disney (headed by Michael Eisner) acquired NBC (headed by Bob Iger, the two companies initially had very different corporate cultures.

NBC was very entrepreneurial. The leaders of the company were there for advice and help, but were generally warm and supportive. If an individual at the company wanted to take a risk, they could do so provided they give strong profit and manage expenses wisely.

Disney was very centralized. All creative decisions were made by Eisner, and the strategic planning committee (a bunch of ivy-league statisticians who would examine every decision).

Sweat the details. Greatness is made up of many small decisions made well. Eisner on designing theme parks and rune on abc sports

Succession planning

This was one of the wildest sections of the book. Roy Disney (who was still on the board) led an effort to get Michael Eisner thrown out of the company. A proxy vote company recommended that he be removed.

Michael announced his resignation plans for the following year, and the company started a search.

Bob became the only internal candidate for the role. He specifically requested that the press release name him as the only internal candidate, so that he wouldn't come across as a lame duck!

A political consultant told Bob: "You're running a political campaign. You have to focus on your plans for the future, not the plans of the past."

The interview process sounded fairly wild, Bob was interviewed across dozens of different sessions with individual board members, and then once again with the entire group. He only once let his temper get the better of him.

It's a good reminder that you can only control your actions, and let those define your worth.

When he started, Bob put together a key strategy for how to revitalize Disney:

  1. Great content – Disney shouldn't be be in the Netflix or Amazon business. They didn't need a sea of content (which consumers would have to wade through). Instead, Disney should focus on having a small number of iconic brands. (cue Pixar, Marvel, and Lucasfilm acquisitions)
  2. Invest in technology – during the second half of the 1990s, Disney animation had a string of poor and forgotten launches: The Emperor's New Groove, The Hunchback of Notre Dame, Tarzan, Hercules, etc. None of these lived up to the iconic brands of Aladdin, The Lion King, or The Little Mermaid which had preceded them. Disney Animation was the leader for all great content–and the company's fate rested on making it great. Bob wanted to invest in technology to become the leader in both animation + in streaming. (cue the Pixar Acquisition)
  3. Become a Global Presence – before Bob took office, Disney largely focused in the US. Bob was convinced that Disney had to become global, and incorporate global stories moreso than it had done to date.

He also had a number of key relationships to attend to:

  1. Roy Disney (who started a lawsuit against the board!). Bob realized that really what Roy wanted was respect and for Disney to feel like home. He made Roy an Emeritus, and allowed him to come to the grounds and movie premiers.
  2. Steve Jobs – when Bob called him up to talk about Pixar, his only question was "how long did you work for Michael". Jobs didn't get seriously interested until Bob told him that the future of television would be mobile. That was the opening to begin to work more closely together, until Bob suggested they buy Pixar.

As one key last change, Bob split up the "strategic planning" group that ruled all of Disney's decision-making. Instead of having a centralized group weigh every decision, as big as acquisitions to ones as small as how parks should do pricing, Bob sent responsibility back to the business owners. "If they can't set pricing for their own parks, they shouldn't be in the jobs they have!"


I hadn't realized this going into the book, but one of the key ways that Bob grew Disney was via strategic acquisitions. During his tenure, he acquired a number of key brands...


Pixar had been dominating the animated movies. The trio of Jobs, Ed Catmull, and John Lasseter had harnessed creative genius and technological innovation within Pixar. The engineering team would consistently deliver new technologies to push the artists forward, and the artists would continuously raise the bar for what the engineers could deliver.

During the Pixar discussions, apparently Steve told Bob 30 minutes before the announcement went live that his cancer had returned! Bob was sworn to secrecy, and had to basically decide whether it was material or not.

After the deal, Steve became Disney's largest shareholder. Bob wasn't worried about bringing him in: "Why would any business not want Steve Jobs more involved with them?"

By the time Bob proposed the acquisition, Pixar had better brand recognition than Disney did! As such, they named the division "Disney Pixar", and used it to reboot Disney Animation (which had been languishing).


Marvel was trickier, as it wasn't a public company. Bob's team had to basically guess at how good of a decision it might be to acquire them, and how much additive value they could provide to Disney. In the end, it was a little messy because it was mostly about IP rights that would gradually come into the fold over time (e.g. Spiderman wasn't in the first part of the deal).

However, the Marvel Cinematic universe unlocked an insane amount of value (a single avengers movie brought in $2b at the box office alone).


The Lucasfilm acquisition was deeply personal to George. Apparently both sides walked on multiple occasions, and George was even upset post-sale that Disney wasn't using his scripts for star wars.

Bob saw Disney as the stewards for Lucasfilm. He intentionally wanted his team to honor the universe that George had built and abstained from applying disney branding to it.


I had forgotten, but Disney was on the edge of acquiring Twitter. Bob ultimately stepped back from it due to a gut call. He felt that Disney wouldn't add anything to twitter's current superpowers, and instead they'd be saddled with a large number of political and content moderation problems.

I'm inclined to agree. I don't really think this acquisition made a ton of sense. Disney is better off advertising on Twitter.

21st Century Fox

There's a story at the end of the 21st Century Fox acquisition from Rupert Murdoch. Apparently Murdoch had seen the writing on the wall, and felt that Disney had better ability to innovate on serving content in a digital age.

He wouldn't sell Fox News (not that Bob wanted it), but was happy to give Disney the rights to its stake in Hulu, the Simpsons, and its movie collection. Despite the controversy around Murdoch's political views, it does seem like a shrewd business move.

During the bidding, Disney pushed the price from the 38/share. Bob didn't want the company to start a bidding war that would push up the bids bit by bit. Instead, he wanted to make a leap that would really cause Comcast to consider another higher bid.

Final Lessons

The book ends with a number of wonderful last lessons that are pure excerpts from the book. While they basically re-hash earlier statements (verbatim!) the stories that they reinforce are great.

Here's a subset of them that really spoke to me...

  • To tell great stories, you need great talent.
  • I talk a lot about “the relentless pursuit of perfection.” In practice, this can mean a lot of things, and it’s hard to define. It’s a mindset, more than a specific set of rules. It’s not about perfectionism at all costs. It’s about creating an environment in which people refuse to accept mediocrity.
  • True integrity—a sense of knowing who you are and being guided by your own clear sense of right and wrong—is a kind of secret leadership weapon. If you trust your own instincts and treat people with respect, the company will come to represent the values you live by.
  • On feedback: Don’t start negatively, and don’t start small. People will often focus on little details as a way of masking a lack of any clear, coherent, big thoughts. If you start petty, you seem petty.
  • Don’t be in the business of playing it safe. Be in the business of creating possibilities for greatness. Be comfortable with failure.
  • "Avoid getting into the business of manufacturing trombone oil. Even if you succeed, it won't make an impact".
  • Optimism emerges from faith in yourself and in the people who work for you. It’s not about saying things are good when they’re not, and it’s not about conveying some blind faith that “things will work out.” It’s about believing in your and others’ abilities.
  • People sometimes shy away from big swings because they build a case against trying something before they even step up to the plate. Long shots aren’t usually as long as they seem. With enough thoughtfulness and commitment, the boldest ideas can be executed.
  • You can do a lot for the morale of the people around you (and therefore the people around them) just by taking the guesswork out of their day-to-day life. A lot of work is complex and requires intense amounts of focus and energy, but this kind of messaging is fairly simple: This is where we want to be. This is how we’re going to get there.
  • It should be about the future, not the past.
  • If you’re in the business of making something, be in the business of making something great.

There's many more good ones, and I'd really encourage this read.