It’s a tradition that goes back to the early days of the U.S. space program: Astronauts write personal letters to their loved ones, to be delivered only if they don’t return from their perilous journey. So last summer, Amazon.com Inc. founder Jeff Bezos, who reveres such rituals, wrote his own heartfelt goodbye to his girlfriend Lauren Sanchez on the eve of his historic ride on a Blue Origin rocket. But then, on the morning of the launch, Bezos couldn’t resist. With colleagues and crewmates milling awkwardly around them, according to a person who heard about the exchange, he handed Sanchez her letter in a grand romantic gesture.
Such moments indicate the current state of mind of the world’s second-wealthiest person. Bezos now appears to spend much of his time focused on his opulent life with Sanchez, his private space company, and his $10 billion climate philanthropy—and surprisingly little on the $1.4 trillion e-commerce and cloud-computing giant he ran for 27 years. “I’m going to split my time between Blue Origin and the Bezos Earth Fund,” he said at the press conference following his safe return to Earth that day, explicitly omitting Amazon, where he remains executive chairman. “There’s going to be a third thing and a fourth thing, but I don’t know what those are yet. I’m not good at doing just a few things.”
Bezos’ personal and professional transformation is striking. Two decades ago, he was a khakis-wearing Wall Street expat with a braying laugh whose obsession with the minutiae of his online store kept him largely out of public view, save for the occasional product announcement. Now he’s a musclebound mainstay of the tabloid media, happy to put his escapades on display on Instagram—whether he’s cavorting at his new $78 million estate on Maui with Leonardo DiCaprio or sending William Shatner and Michael Strahan into space on his rockets.
The dramatic evolution of Bezos appeared to accelerate after Amazon cemented its dominance of online retailing. The company created industry-changing products with the Kindle and Alexa and has maintained breakneck growth at such divisions as the Amazon Marketplace and Amazon Logistics. Masterminded and often micromanaged by Bezos himself, these initiatives turbocharged the company’s expansion while creating unanticipated problems for customers, employees, independent online sellers, and brick-and-mortar retailers caught in Amazon’s path.
Bezos’ monumental success also elevated him to icon status in the business world and inflated his personal fortune, now estimated at $160 billion by the Bloomberg Billionaires Index. In Amazon’s early days, Bezos emphasized values like modesty and frugality and encoded them into the company’s leadership principles, which employees were required to follow almost religiously. Lately, he’s been more preoccupied with the construction of a $500 million yacht, which may require the dismantling of an historic Dutch bridge for it to reach open sea, an indulgence that contrasts unfavorably with the philanthropic campaign of his ex-wife, MacKenzie Scott. She’s giving away her $46 billion post-divorce fortune at a rapid clip while passionately arguing in online essays that the money is the byproduct not of ingenuity but of a broken system.
After being practically worshipped for years, Bezos is now often the subject of something else: mockery. Late-night talk show hosts have poked fun at not only the conspicuously phallic shape of the New Shepard rocket but things such as his New Year’s Eve ensemble of a silk shirt, white pants, and heart-shaped sunglasses (evidenced in a photo Sanchez posted to Instagram). Then there was the blue jumpsuit he paired with a cowboy hat for his space launch. According to someone who witnessed him trying it on for a preflight photo shoot, Bezos was volubly upset that the jumpsuit fit poorly around the crotch—and had his tailor flown to his Texas ranch to fix it.
All of this is ridiculous, of course, and Bezos probably knows it. Some former colleagues think it’s a reason he has distanced himself publicly from Amazon. “He does have a level of self-awareness,” says Craig Berman, a former Amazon vice president for global communications. “I think that may be what may have ultimately contributed to him stepping away from the CEO role.”
That’s left Amazon’s fate in the hands of Bezos’ widely respected former deputy, Andy Jassy, a sports fanatic from Scarsdale, N.Y., who apprenticed with Bezos in the company’s early days as his technical adviser. For 15 years, Jassy has built Amazon Web Services into a nuclear reactor of growing sales that powers much of Amazon’s profit. As chief executive officer of the entire company, he now faces an array of formidable challenges: a tight labor market that requires Amazon to spend more to hire warehouse workers, growing employee dissatisfaction and unionization efforts, increased government scrutiny and potential regulation, and the slowing growth of e-commerce as the pandemic ebbs and people return to shopping in stores.
Jassy’s biggest challenge may be Amazon’s stock price, which declined about 8% over the past 12 months while the S&P 500 rose 9%. Amazon employees, who are heavily compensated with stock, could exit in droves if the share price doesn’t rebound. On March 9, the board authorized a 20-for-1 stock split, to make shares more accessible to retail investors and employees. Amazon has also said it was doubling the maximum base salary to $350,000, but many employees say they’re on edge in advance of their annual reviews in April. “People are worried and asking, ‘Should I run now before everyone else gets bad news and starts looking for other jobs?’ ” says one worker, who requested anonymity because she isn’t authorized to speak publicly.
But Bezos didn’t leave the cupboard entirely bare for Jassy. AWS shows few signs of slowing down, and for the first time, Amazon divulged financial details of a surprisingly robust advertising business that collected $9.8 billion over the holiday quarter, up 33% from the previous year. Jassy plans to close physical stores that are underperforming and open more cashierless supermarkets and a first-of-its-kind clothing store in Glendale, Calif., Amazon Style, that lets shoppers browse products on a smartphone app and have them delivered directly to a dressing room. He’s also talked publicly about Amazon’s prospects in the massive health-care market and for its new Alexa-equipped home robot, Astro, which the company unveiled last September and has since rolled out methodically to beta testers.
In the meantime, Wall Street seems to be getting restless. Last month activist investor Daniel Loeb told his hedge fund’s clients that he thought Amazon could unlock $1 trillion in value by splitting its e-commerce and cloud units, according to the Wall Street Journal. While there’s no evidence that Loeb will wage a full-blown activist campaign to pressure the company to break itself up, it’s the kind of second-guessing that was inconceivable for the last 15 years of Bezos’ tenure as CEO, when he had an aura of invincibility, thanks to years of farsighted decisions and remarkable inventions.
Whether Bezos advised his successor on how to deal with Loeb’s alarming comments is unknown. He was probably recovering from a busy weekend: As chronicled in the tabloids and on Instagram, he and Sanchez were in Los Angeles, where they partied into the early hours with celebs like Justin Bieber and Khloé Kardashian, then watched the Rams win the Super Bowl from a private box above midfield. —With Spencer SoperListen to the podcast, Foundering: The Amazon Story. The first two episodes premiered on March 10, on Bloomberg.com/Foundering.
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