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Inside Jeff Bezos' Mysterious Private World: A Dating Flow Chart, That Booming Laugh and Many Billions

Amazon founder Jeff Bezos is sometimes the richest man alive — but once upon a time, the newly engaged visionary was just a math whiz with a dream and angel investors named Mom and Dad.

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If there's one thing everybody knows about Jeff Bezos, it's that he's obscenely rich.

The 59-year-old has the kind of money that's too mind-boggling to exist in physical dollars and cents, but rather just takes up a line on a piece of paper at his money manager's office. His estimated $142.9 billion fortune is currently enough to make him the third-richest man in the world, according to Forbes' Real-Time Billionaires List, second only to Elon Musk and luxury brand magnate Bernard Arnault.

And even if the name Bezos doesn't mean anything to you, it's extremely likely you have contributed to his eye-popping wealth as the founder of Amazon, the online retail behemoth that's as close to an instant answer to your prayers you're likely to get (especially if you're praying for shoes, dish soap and pet food to appear all at once, and you asked a woman named Alexa, who lives in a little box in your home, to make it happen), and multimedia mogul.

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But while Bezos, who stepped down as CEO of Amazon on July 5, 2021, is a legend in the online commerce and disrupter worlds — as well as a political donor and philanthropist, Hollywood mover and shaker, and, since 2013, the owner of the Washington Post — he never became your friendly neighborhood billionaire like Warren Buffett, the face of eradicating malaria like Bill Gates or an enigmatic man in black holding the future in the palm of his hand, like the late Steve Jobs.

He's even far from the most outsize personality in the race to commercialize space travel, with Musk and Richard Branson and vying for that title.

In fact, not a lot of regular folks were paying all that much attention to Bezos until his love life exploded all over the tabloids in the most relatable (for celebrities, that is) of ways.

In January 2019, Bezos and his wife of 25 years, author and philanthropist MacKenzie Scott, announced that they were divorcing. At the time they shared four children, an estimated 400,000 acres of property, the aforementioned billions, and, according to TMZ, no prenuptial agreement.

Bit of a rookie mistake, but they married the year before he founded Amazon in the garage of their rented Seattle home, in 1994. Who knew?

But the split, according to the exes, was amicable.

"As our family and close friends know, after a long period of loving exploration and trial separation, we have decided to divorce and continue our shared lives as friends," read a joint statement that Bezos tweeted out in the rarest of comments about his personal life.

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"We feel incredibly lucky to have found each other and deeply grateful for every one of the years we have been married to each other. If we had known we would separate after 25 years, we would do it all again. We've had such a great life together as a married couple, and we also see wonderful futures ahead, as parents, friends, partners in ventures and projects, and as individuals pursuing ventures and adventures. Though the labels might be different, we remain a family, and we remain friends."

That seemed to remain the case, with Scott also becoming one of the richest people in the world once her piece of the fortune was finalized.

What made the whole thing spicier at the time was that Bezos already had a girlfriend, veteran TV personality and former "Good Day LA" co-host Lauren Sánchez — who was still technically married to but separated from Patrick Whitesell, the co-CEO of mega-agency WME and father of two of her three children.

Bezos and Sánchez have been together ever since, and are now engaged, but their coupling was painted with the scandal brush at first, prompting Bezos to take action.

Whitesell was reportedly blindsided to find out his wife was having a relationship with Bezos, and the Amazon founder's purported sexy text exchanges with Sánchez were leaked for public consumption.

An attorney for Bezos told the National Enquirer, which first published the texts, that it was "widely known" that his client and Scott were "long separated." A source also told Page Six, "MacKenzie knew they were dating, the news [Wednesday] was not a surprise to her. Lauren was with Jeff at the Golden Globes [in 2019] because they are dating."

Bezos, Sánchez and Whitesell were all spotted chatting at Amazon's Golden Globes after-party that night, according to People.

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Bezos, however, went a step further and took to Medium to accuse the Enquirer of attempted extortion, alleging the publication threatened to publish intimate photos if he didn't make a favorable public statement about the tabloid.

"Any personal embarrassment AMI could cause me takes a back seat because there's a much more important matter involved here," he wrote. "If in my position I can't stand up to this kind of extortion, how many people can?"

The Enquirer maintained its reporting on Bezos was lawful.

Massive global footprint aside, the Medium post really was an uncharacteristic bit of public pushback on one of the countless narratives that has circulated about him over the past 30 years.

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Bezos a man who had "proved quite indifferent to the opinion of others... an avid problem solver, a man who has a chess grandmaster's view of the competitive landscape," author Brad Stone wrote in his 2013 book "The Everything Store."

He was a congenial and outgoing guy with a famously big laugh ("like a cross between a mating elephant seal and a power tool," Stone wrote), but prone to the same mercurial behavior associated with Jobs, friendly one minute and liable to cut a person down to size the next.

The name Amazon, as in the world's largest river, reflected Bezos' mighty ambition — and, starting with "A," would be near the top of any alphabetical company listing.

"People say that your life races before your eyes," he told Fast Company in 2004, a year after he emerged from a helicopter crash with only a few cuts on his head. "This particular accident happened slowly enough that we had a few seconds to contemplate it." Bezos continued, laughing heartily, "I have to say, nothing extremely profound flashed through my head in those few seconds. My main thought was, 'This is such a silly way to die.'"

"It wasn't life-changing in any major way. I've learned a fairly tactical lesson from it, I'm afraid. The biggest takeaway is: Avoid helicopters whenever possible! They're not as reliable as fixed-wing aircraft."

Sanchez, incidentally, is a helicopter pilot who owned her own aerial filming company, Black Ops Aviation. Not only does Bezos' $500 million superyacht have a helipad, but his fiancée told WSJ. Magazine earlier this year that he's getting his pilot's license.

"Will you guard your heart against rejection, or will you act when you fall in love?" Bezos inquired in the commencement speech he gave for Princeton's Class of 2010. "Will you play it safe, or will you be a little bit swashbuckling?"

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But it all started with a bunch of books.

Bezos and Scott first met in New York while working at a Wall Street hedge fund. Bezos, tuned in to the fact that Internet commerce was the wave of the future, studied his options and decided he wanted to start an online bookstore. He took the idea to his own boss, who, according to Tom Robinson's "Jeff Bezos: Amazon.com Architect," said it was a good idea, but a better idea for someone who didn't already have a good job.

When he got the idea for what would become Amazon (and was almost called Relentless.com, but friends deemed that scary), Bezos came up with what he called a "regret-minimization framework" to help him work out the pros and cons of leaving his successful career in finance. "When you are in the thick of things, you can get confused by small stuff," he later said, per Stone.

"I have no business sense whatsoever," Scott told Vogue in 2013, "but I saw how excited he was."

"I had just turned 30 years old, and I'd been married for a year," Bezos recounted in the 2010 Princeton commencement address. "I told my wife MacKenzie that I wanted to quit my job and go do this crazy thing that probably wouldn't work since most startups don't, and I wasn't sure what would happen after that."

So in the summer of 1994, Bezos and his wife flew to Texas, where his parents lived. They told the movers to just start driving west, that they would follow up with an exact destination — which, at the moment, they weren't sure of yet.

Jackie and Miguel Bezos (who also goes by Mike) loaned the couple the SUV in which MacKenzie drove them to Seattle, while Bezos worked on his laptop. They didn't have any particular personal ties to the city, but a friend had recommended it—and at the time online retailers didn't have to collect sales tax in states where they didn't have a physical presence. Washington was small and he wanted the rest of his customers around the country to avoid paying sales tax.

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Jackie was 17 when Jeff was born in Albuquerque; she divorced his biological father, Ted Jorgenson, when their child was 1. Mike, who left Cuba for the U.S. when he was 15, met Jackie while working the night shift at Bank of New Mexico while attending the University of Albuquerque. They married when Jeff was 4 and Mike adopted him. Bezos has said that Mike is the only father he's ever known. The family moved around for Mike's work, from Albuquerque, to Houston and then to Miami, where Bezos enrolled in a science program at University of Florida while still in high school.

He was a supremely talented student in math and science, a Star Trek fan who loved to tinker with stuff in the garage, senior class president and valedictorian. He went on to major in electrical engineering and computer science at Princeton.

In 1995, Jackie and Mike invested $245,573 in their son's start-up, Amazon.com.

"I want you to know how risky this is," Jeff told them, according to remarks Mike Bezos gave in 2015 at the National Constitution Center in Philadelphia, "because I want to come home at dinner for Thanksgiving and I don't want you to be mad at me."

According to Bloomberg, their stake in the company may now be worth about $30 billion — a 12 million percent return. Bezos' younger siblings, Mark and Christina, also purchased 30,000 shares apiece for $10,000 in 1996; each holding could be worth $640 million.

"We were fortunate enough that we have lived overseas [they had just spent three years in Bogotá, Colombia] and we have saved a few pennies so we were able to be an angel investor," Mike, a former engineer at Exxon, said. "The rest is history."

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Back in 1990, Bezos joined investment firm D.E. Shaw & Company and was a senior vice president within two years. According to The Everything Store, as a single guy he took ballroom dancing lessons, hoping to increase the probability of meeting "n+ women." He made a flow chart.

"The number one criterion was that I wanted a woman who could get me out of a third-world prison," Bezos later said, according to Richard Brandt's 2011 book "One Click: Jeff Bezos and the Rise of Amazon.com." "What I really wanted was someone resourceful. But nobody knows what you mean when you say, 'I'm looking for a resourceful woman'... Life's too short to hang out with people who aren't resourceful."

Eventually he met MacKenzie Scott (née Tuttle), a research associate and fellow Princeton grad from San Francisco who worked in the office right next to his. Sensing a connection as they got to know each other, and Bezos feeling reluctant to make a move as the supervisor of the team she worked on, she approached him.

"My office was next door to his, and all day I listened to that fabulous laugh," Scott, an English major who had done research for Toni Morrison while the Nobel Prize winner was writing "Jazz," told Vogue. "How could you not fall in love with that laugh?"

They got engaged three months after their first lunch date, then married in 1993 at the Breakers in West Palm Beach, Fla., where the reception included an adult-size play area with water balloons.

"I think my wife is resourceful, smart, brainy, and hot," Bezos also told Vogue, "but I had the good fortune of having seen her résumé before I met her, so I knew exactly what her SATs were." (He wouldn't reveal her score.)

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Once in Seattle, they rented a house for $890 a month in the suburb of Bellevue; set up some tables, chairs and computers in their garage, starting with $25,000 of their own money; and Amazon.com was registered on Feb. 9, 1995, with Bezos' parents being his primary investors at the time.

Scott was the company's first bookkeeper, secretary and office manager. The couple's golden retriever, Kamala (named after a creature from "Star Trek: The Next Generation") would hang out in the garage. Amazon's small staff would sometimes go to a nearby Barnes & Noble for coffee and meetings.

The site went live on July 16, 1995.

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By that September, Amazon.com was selling $20,000 in books a week. That first year, the company had a net loss of $303,000. They went public in 1997 and raised $54 million in capital; moved into new headquarters in a former hospital in 1998; and Bezos was named TIME magazine's Person of the Year in 1999. "[P]athologically happy and infectiously enthusiastic," the article called him.

Amazon's death knell was sounded many a time in the 1990s, and the company would not report a quarterly profit, of $5 million, until the fourth quarter of 2001 — which saw $2 billion in sales for the year. 2003 was its first profitable year. In 2004, Fast Company reported that they were on track for $7 billion in sales and a $400 million in earnings. In the fourth quarter of 2017 alone, Amazon reported $1.86 billion in net income.

But profit can be incidental at first when it comes to getting filthy rich in the tech world.

"The thing about inventing is you have to be both stubborn and flexible, more or less simultaneously," he told Fast Company. "Of course, the hard part is figuring out when to be which."

Amazon's infamously intense, overtime-expected, high-turnover workplace culture has been well-documented, often not flatteringly. Bezos, whose inspiration included the visionaries Thomas Edison and Walt Disney, expects his employees to abide by 14 core leadership principles: customer obsession; ownership; invent and simplify; "are right, a lot" (if you know what you're doing, you're probably right); learn and be curious; hire and develop the best; insist on the highest standards; think big; bias for action (go for it, don't overthink); frugality; earn trust; dive deep; have backbone, disagree and commit; and deliver results.

Per Stone, employees don't give Power Point presentations, but rather have to write six-page treatises laying out their ideas — it fosters critical thinking, according to the boss.

"It's not easy to work here...but were are working to build something important, something that matters to our customers, something that we can all tell our grandchildren about," Bezos wrote in a 1997 letter to shareholders.

As he told the Princeton class of 2010, "When it's tough, will you give up, or will you be relentless? Will you be a cynic, or will you be a builder? Will you be clever at the expense of others, or will you be kind?"

His unapologetic way of doing business has, to put it very mildly, worked for him.

"To me Amazon is a story of a brilliant founder who personally drove the vision," Eric Schmidt, then executive chairman of Google (and an Amazon Prime member), told Brad Stone for "The Everything Store." "There are almost no better examples... It lost hundreds of millions of dollars. But Jeff was very garrulous, very smart. He's a classic technical founder of a business, who understands every detail and cares about it more than anyone."

Incidentally, MacKenzie left a one-star review of "The Everything Store" on Amazon.com under the subject line, "I wanted to like this book," and called it a "lopsided and misleading portrait of the people and culture at Amazon." Stone, in response, told the New York Times, that Bezos had "approved many interviews with current Amazon executives and former Amazon executives" and had declined interview requests for himself. "Most of the readers and reviewers have been inspired by Amazon's story," Stone said. "To me, it's not an unflattering account."

Over the years, they acquired a real estate portfolio that included a gated 5.3-acre compound in the Seattle suburb of Medina reachable via the longest floating bridge in the world; the South Texas ranch where Bezos used to spend summers with his grandparents, near where his aeronautics and space-exploration company Blue Origin is also based; a $24 million home in Beverly Hills; four condos in a building on Manhattan's Upper West Side; and a residence in Washington D.C. that broke a record for Beltway home prices when Bezos bought the former Textile Museum in 2016 for $23 million.

They also share three sons and a daughter. They are understandably incredibly private when it comes to their kids, but Bezos shared some parenting insight at the Summit LA 17 event while being interviewed by his brother, Mark.

"How do you help your children, what's the right thing?" he mused. "My wife has a great saying — we let our kids use, even now they're 17 through 12, but even when they were 4, we would let them use sharp knives. By the time they were, I don't know, maybe 7 or 8, we would let them use certain power tools and my wife, much to her credit, she has this great saying, 'I would much rather have a kid with 9 fingers than a resourceless kid.' Which, I just think, is a fantastic attitude about life."

Scott also wrote two novels, 2005's "The Testing of Luther Albright" and 2013's "Traps." "Jeff is my best reader," she said, noting that Bezos would block out a big chunk of time and read a manuscript in one sitting, writing her detailed notes.

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She recalled to Vogue in 2013 how it took her 10 years to finish her first book, considering she was rather busy helping run Amazon.com and having a family for much of that time.

Acknowledging how unusual her lot in life had become, MacKenzie said, "I am definitely a lottery winner of a certain kind and it makes my life wonderful in many ways, but that's not the lottery I feel defined by. The fact that I got wonderful parents who believed in education and never doubted I could be a writer, the fact that I have a spouse I love, those are the things that define me."

"Jeff is the opposite of me," she also said. "He likes to meet people. He's a very social guy. Cocktail parties for me can be nerve-racking. The brevity of conversations, the number of them—it's not my sweet spot."

Bezos said of his wife, "Writing makes her really happy." On days when she would get up early to write, "by the time I come down, she will be literally dancing in the kitchen, which the kids and I love."

With the deepest pockets in the world come great responsibility, and admirers and critics alike wondered for years what Bezos was planning to do with all that dough.

In 2012, the Seattle Times reported that Amazon was a relative lightweight on the local philanthropy circuit, and that the United Way in King County reported $0 in donations from the company in 2011, while other prominent corporate residents, including Microsoft, Nordstrom and Boeing had given 6- and 7-figure sums.

"Our core business activities are probably the most important thing we do to contribute, as well as our employment in the area," Bezos told the paper in 2011 (he didn't comment on the 2012 report).

Of course he and MacKenzie have a family foundation (run by his parents) that benefits children's education and they've been personally active in charitable causes, donating to political candidates and otherwise doling out money for decades. In 2007, Bezos paid $3.98 million for one of only seven handwritten and illustrated copies of J.K. Rowling's "The Tales of Beedle the Bard," with all proceeds going to Children's Voice (Rowling gave the other six to people closely connected to the Potterverse). They have given to both Democratic and Republican candidates, but their social politics lean progressive: in 2012 they gave $2.5 million to support an ultimately successful referendum legalizing same-sex marriage in Washington state, which made them the biggest financial backers of the cause in the country.

The New York Times, citing various data, reported in the summer of 2017 that Bezos had personally given away about $100 million.

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The Bezoses gave $15 million to Princeton to establish the Bezos Center for Neural Circuit Dynamics at the Princeton Neuroscience Institute. The Bezos Family Foundation has donated a total of about $65 million to Fred Hutchinson Cancer Research Center in Seattle. They gave $10 million to Seattle's Museum of History and Industry in 2011. And the $250 million Bezos paid to buy the Washington Post could be considered benevolent, considering the state of the newspaper business, though that's technically a for-profit venture. (It at least seemed a bargain compared to the $13.7 billion Amazon spent to acquire Whole Foods in 2017.)

But in June 2017, Bezos — then the only one of the U.S.' top five billionaires not to sign Bill Gates and Warren Buffett's "Giving Pledge" promising to give away at least half of their wealth — tweeted that he was open to suggestions, writing, "I'm thinking about a philanthropy strategy that is the opposite of how I mostly spend my time—working on the long term. For philanthropy, I find I'm drawn to the other end of the spectrum: the right now."

As of November 2022, per CNBC, he remained among the seven richest people in the world who haven't signed. Among those who have: His ex-wife and Elon Musk.

Scott, meanwhile, recently issued a $250 million open call for philanthropic opportunities for her foundation. She's been busy on the personal front, too, marrying science teacher Dan Jewett in 2021 and filing for divorce in September 2022.

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But Bezos has stated that he plans to give most of his fortune away, and just as he and Scott teamed up to make numerous massive pledges during their time together, he and Sánchez are also doing the work.

"It's the greatest experience I've ever had," Sánchez said of partnering with her now-fiancé on business and philanthropic matters. "I've always had a career very separate from my partner. We love to be together and we love to work together. He's helping me with the book. He's getting his pilot's license. We fly together. We work out together. We're together all the time."

"Lauren is the most generous, most big-hearted person that you would ever meet," told CNN in November. "So, she is an inspiration in that way. She never misses a birthday. The network of people that she gives birthday presents to is gigantic. And that's just a small example."

Bezos concluded his address to the Princeton grads in 2010 by reiterating his tendency to think about how he's going to feel about his life when looking back on it from an older perch one day.

"I will hazard a prediction. When you are 80 years old, and in a quiet moment of reflection narrating for only yourself the most personal version of your life story, the telling that will be most compact and meaningful will be the series of choices you have made. In the end, we are our choices. Build yourself a great story."

(Originally published Jan. 11, 2019, at 3 a.m. PT)

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