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Jeff Bezos: 9 Remarkable Choices That Shaped the Richest Man in the World "Cleverness is a gift. Kindness is a choice."

By Carolyn Sun

Opinions expressed by Entrepreneur contributors are their own.

JOE KLAMAR | AFP | GettyImages

Jeff Bezos may be the richest man in the world, worth more than $105 billion, but money has always been a means to an end for him, a way for the Amazon founder to wield influence and shape the future. The single most remarkable accomplishment of his to date is that he's fundamentally changed the culture of shopping, an implausible and tectonic shift.

"It's hard to imagine life without," said the dean of Princeton University during her introduction of Bezos, who gave the commencement speech for the graduating class of 2010. Amazon had, by that point, become a cultural icon -- with Bezos right along with it.

He spoke to the class of 2010 about the choices they will face in life. "Cleverness," he said, "is a gift. Kindness is a choice." In a story illustrating this, he recalled something his grandfather told him: "One day you'll understand that it's harder to be kind than clever."

Throughout his life, Bezos has been widely admired for the daring and difficult choices he's made during his 54 years. We here at Entrepreneur want to celebrate them and the entrepreneur who made them.

The next nine slides go over key choices that have shaped Bezos' life.

Related: Is Your Work Ethic Better than Average? Find Out in 5 Questions.

Steve Kagan | Liaison | Getty Images

Even early on in life, he did what he said he would do.

Establishing a track record for setting his sights on a goal and meeting them started early in Bezos's life. At his high school in Miami, he let it be known far and wide that he would be class valedictorian, according to a classmate. He was true to his word, and also captured the prize of National Merit Scholar and a Silver Knight award winner, one of the nation's most highly regarded student awards. His high school girlfriend recalled how the young Bezos was fascinated with space exploration and the desire to inhabit other planets. In 2000, he founded the private space exploration company Blue Origin, which plans to launch its first space rocket in 2019.

Related: Quiz: 'Are You a Natural-Born Leader?' Measure Your Leadership Ability in 4 Questions.

Rex Rystedt | The LIFE Images Collection | Getty Images

He noticed a wild opportunity and jumped on it.

By all standards, the 30-year-old Bezos was already successful when he quit his job in 1994 as the senior vice president of a Wall Street investment bank. While researching new investments for D.E. Shaw & Co., he happened upon a statistic that would change his life: internet usage was exploding by 2,300 percent a month. While the investor in Bezos recognized the opportunity, it was the entrepreneur in him that quit his six-figure job, packed his wife and dog and moved to Seattle, where he began figuring out potential ecommerce businesses to build.

Related: Jeff Bezos

Jerod Harris | Getty Images

He married someone as resourceful as he is.

Bezos is famously quoted for what he was looking for in a wife: "The number-one criterion was that I wanted a woman who could get me out of a Third World prison." He met and married his partner-in-resourcefulness, Mackenzie, a Princeton graduate he interviewed to be a research associate at the investment firm he was vice president of at the time.

He once told Vogue, "I think my wife is resourceful, smart, brainy and hot, but I had the good fortune of having seen her résumé before I met her, so I knew exactly what her SATs were."

His wife was the one who asked him out. "How can you not fall in love with that laugh?" she has said about his signature braying laugh. Bezos and the published novelist and mother of four were engaged within three months of their first date and married after six.

Related: Fuel Your Drive With These Motivational Stories of Elon Musk, Jeff Bezos and Oprah Winfrey


He initially focused on book sales.

When Bezos was trying to figure out what sort of ecommerce business to build, he had drawn up a list of 20 potential products, including software, CDs and books. He landed on books, due to the sheer number of titles in existence -- a virtual bookstore could easily offer more titles than and undercut prices of any brick-and-mortar store. Also, Seattle was close to a book source, the Ingram Book Group's Oregon warehouse.

In July 1995, launched, offering more than 1 million titles and an online community that buyers could easily navigate, with book reviews left by other shoppers. The business was a smashing success, and a year later, had made more than $15.7 million in sales and grown to 100 employees from five.

By focusing narrowly on books, he was able to win that market and create a template for the company to launch into other markets.

Related: How Does Your Parenting Technique Compare to Elon Musk's, Sheryl Sandberg's and Jeff Bezos'?

Daniel Acker | Getty Images

He puts his customers first.

Amazon's brand is excellent customer service -- and it's a strategy that grew the business and built customer loyalty. In the early days of Amazon, Bezos would bring an empty chair into meetings and would tell his executives that the seat is occupied by the customer, "the most important person in the room." Decisions for every department in Amazon are driven by data around the customer experience.

Even today, a customer can send an email to Bezos's inbox at "When the email gets to his inbox, Bezos forwards the note to the employee who is best equipped to handle the request with "?' in the subject line. Then once the issue is dealt with, the team member sends a rundown of what happened to Bezos so he can know that the problem was solved,"'s Nina Zipkin wrote.

Related: Is Your Work Ethic Better than Average? Find Out in 5 Questions.

Matthew Staver | Getty Images

He goes beyond Amazon.

Bezos not only built and expanded the Amazon umbrella into areas such as web services, groceries with the $13.7-billion acquisition of Whole Foods and a wind farm for renewable energy, but he also ventured beyond Amazon. In 2000, he founded (and funded) space tourism company Blue Origin, and in 2013, bought The Washington Post.

Related: Quiz: 'Are You a Natural-Born Leader?' Measure Your Leadership Ability in 4 Questions.
Scott Eells | Getty Images

He spends his time with family.

Bezos is an intense guy, and at one time, a workaholic who, during his investment bank days, kept a sleeping bag by his desk so he could spend the night. However, Bezos now chooses to spend time with his four children and wife Mackenzie. He has an established routine of eating a leisurely breakfast together every morning. After dinner, he has another ritual: washing the dishes. "I'm pretty convinced it's the sexiest thing I do," he has said.

Related: Jeff Bezos Just Posted This Weird, Kind of Badass Video of Himself on Top of a Wind Turbine

Drew Angerer | Getty Images

He takes care of himself.

While adequate sleep wasn't always his way of life, now the Amazon CEO gets eight hours of sleep (he doesn't even use an alarm clock to wake up), and he eats a healthy breakfast while favoring food trucks outside Amazon headquarters for lunch.

Judging by his buff Navy Seal form at a 2017 Sun Valley conference, he also clearly works out. It's unknown whether Bezos has a regular workout routine or what it is, but the fact that he can fit in a workout routine while running Amazon, The Washington Post and Blue Origin is pretty jaw-dropping.

Related: I Learned a Lot About Strong Company Culture From Jeff Bezos -- But There's 1 Strategy I Won't Copy

Paul Morigi | Getty Images

He gives back.

When compared to some of his billionaire brethren (Warren Buffett, Bill Gates and Mark Zuckerberg), Bezos's philanthropic work remains pretty under the radar. However, he has established a philanthropic initiative called the Bezos Family Foundation, which is run by his parents. His latest effort in philanthropy is a $33 million donation to a college scholarship program for Deferred Action for Childhood Arrivals (DACA) recipients, putting him squarely in the middle of a hot-button political debate. His donation follows President Trump's announcement last year that he intends to end protection for DACA recipients and Trump's stinging criticism of the Amazon founder and The Washington Post.

Another of the foundation's recent efforts is providing facilities for a homeless shelter called Mary's Place that's adjacent to Amazon's new office space in downtown Seattle.

Bezos is interested in crowdsourcing ideas for how to throw his weight behind philanthropy with immediate impact, and in June 2017, he asked his Twitter followers for ideas.

"I'm thinking about a philanthropy strategy that is the opposite of how I mostly spend my time -- working on the long term," Bezos wrote. "For philanthropy, I find I'm drawn to the opposite end of the spectrum: the right now."

Related: 10 Inspiring Quotes From the Fearless Jeff Bezos

Carolyn Sun is a freelance writer for Find out more on Twitter and Facebook


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