7 Life-Changing Documentaries on Success, Failure, and Business

Here are seven of the best documentaries I’ve watched recently. These films will entertain you while teaching you about some of the most successful people in the world (or the worst failures).

Quincy – available on Netflix

This man, Quincy Jones, is maybe the best music producer of all time you’ve never heard of. He worked directly with Ray Charles and then Frank Sinatra. He produced various well-known film scores, including the first Ocean’s Eleven. He arranged the music in the Wiz where he met Michael Jackson. He produced Michael’s first album, Off the Wall, and Thriller.

Her daughter, Rashida Jones, who is Jim’s love interest in The Office, made this documentary. And this film won a Grammy.

You get a magical journey through his life. You learn about his journey and his mistakes. This was a man who discovered his passion instantaneously early on. I found it interesting how he struggled with marriages and overwork.

He dropped a lot of pearls of wisdom through. I discovered that your music can’t be more or less of who you are as a human being. It’s damaging to not know the history of where you or your music came from. Never do music for fame or money; create music because it moves you. We can summarize all of music in twelve notes.

Fyre – available on Netflix

Discover what happens when a man has a grand vision, the charisma to sell that idea, the stubbornness to believe he is always right, and the willingness to lie. This story details how a social media campaign to build the greatest, luxury music festival of all time turns into a shitshow and lawsuit.

Free Solo, a Nat Geo movie (directed by Jimmy Chin)

Free soloing is rock climbing with no gear to protect yourself. A large portion of professional practitioners die over the years from slipping. This Emmy-winning documentary profiles one of the greatest, living free solo-er’s. Specifically, it details this man’s life history and his attempt to scale one of the largest, seemingly unscalable mountain structures in the world. If he makes one mistake, he falls and dies.

I was most fascinated by the psychology of this man. It seemed his drive to keep doing something so dangerous was biological and environmental. A brain scan revealed he needed a lot more stimuli than the normal person to feel the thrill he desired. He also wasn’t ever praised and appreciated by his mother, which may have driven him.

I’d never free solo myself, but this film is an entertaining thriller. I got to attend one of his talks. It turns out that there’s a lot of work and networking needed to win an Emmy. And being famous didn’t really change his happiness. He gets more joy from donating to others than getting recognized at airports. Money didn’t change much. He was already happy living off $20K a year, traveling the country in a van to rock climb.

Jiro Dreams of Sushi – available on Netflix

Witness the life of an 85-year-old sushi master who charges $300-a-plate. This luxury sushi bar in Japan has a waitlist of months. You’ll learn another story of the amount of focus it takes to get to this level of skill. This man skipped awards ceremonies honoring him because he would rather work.

Inside Bill’s Brain: Decoding Bill Gates – available on Netflix

This three-part documentary provides a fresh perspective on Bill Gates and what he’s doing now. I’m tired of people trying to tell a story about someone’s life that we’ve heard too many times before. This film does a decent job of providing new stories and memories of Bill’s life growing up that you may have missed.

Even when I’m waiting through something I’ve heard about him before, I know those scenes don’t last long since the film talks just as much, if not more, on what his philanthropy is doing now to change the world. I was partially expecting a somewhat dry, boring documentary, but I got a fresh, interesting look at his life and how his brain works, which differs from the average person. The animations, photographs, and interviews with childhood friends and Bill himself keep things interesting.

I learned a lot about him I didn’t know. I thought I was a decent reader, but this man tears through a dozen thick, dense non-fiction every week. His mind can process complex, chaotic problems. His mother influenced his social skills tremendously. One of Bill’s sisters doesn’t think Bill would’ve succeeded like he did if his mother didn’t make him go to various social events to interact with others.

Killer Inside: The Mind of Aaron Hernandez – available on Netflix

Imagine you’re a football player making tens of millions of dollars per year. How can life ever go wrong? Murder. This mini-series tells the story of how Aaron Hernandez went from superstar to sentenced to life in jail to hanging himself in his cell with his bed sheets. You learn how his life unfolded and possible reasons he ended up how he did (hanging with the wrong people, anger management, head trauma, cultural expectations, and dysfunctional parents). You get to draw your own conclusions.

Charlie Munger, respected businessman, has said that you can live a good life if you can just avoid the big mistakes. If you watch this series with that thought in mind, you’ll start thinking of what those big mistakes are, how easy they can be to make if you’re not careful, and how to avoid them.

The Wizard of Lies – available on HBO

This one’s technically a movie rather than a documentary. The film stars Robert De Niro as Bernie Madoff, a man who committed one of the greatest, longest Ponzi schemes of all time. It doesn’t cover his whole life from the time he was born. Instead, it starts off when he turns himself in. The story has a few flashbacks to explain his background.

It’s unnerving and fascinating to see the emotional struggle and pain he caused himself and his family. His dishonesty and stress eats away at him, bubbles up and eventually destroys him. I also found it remarkable that he lied to the world for so long and didn’t get caught as one of the chairman of NASDAQ. The U.S. Securities and Exchange Commission was incompetent throughout the story, failing to identify that he was fudging his numbers for years.

Let this story be a cautionary tale about the consequences of lying and cheating. His dread of getting caught destroyed his soul. And his behavior caused his son’s suicide.

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By Will Chou

I am the the founder of this site and I am grateful you are here to be part of this awesome community. I help hard-working Asian American Millennials get rich doing work they love.

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