It was just another Tuesday in Seattle when Andy Jassy sat down in his office at the Amazon re:invent building, one of many on the sprawling campus, to take what would end up being the most important phone call of his life. Seattle is often gloomy and wet during the winter months, but on this particular January day, the rain was torrential, slamming against the windows of the 37-story high-rise. In the distance, the Seattle Space Needle disappeared between the clouds as if it were threaded through the sky. Inside, the building was quiet. Jassy, who is 5 feet 10 inches tall with an oblong face and short, spiky hair, was dressed in a variation of the same outfit he always wears, a dowdy button-down with worn-out jeans and leather high-tops with a white sole.
That day, just like every day for the past two-plus decades, Jassy had been the first person into the office, arriving in his 1998 Jeep Cherokee Sport, the same vehicle he has been driving since moving to Seattle in 1997, when he took a job at Amazon the Monday after he finished business school at Harvard. Unlike most Amazonians, who worked from home as the COVID-19 pandemic ravaged the world, Jassy had been making the trek to the office from his home in the Capitol Hill neighborhood to run Amazon Web Services (AWS), the biggest cloud storage business on the planet, with more than $50 billion in annual revenue (more than double that of Salesforce).
A few hours earlier, Jassy had received an email from his boss, Jeff Bezos, the CEO of Amazon, asking if they could talk on the phone. Bezos-level requests weren’t a regular occurrence for Jassy, usually landing in his inbox every couple of weeks, so such a note meant there was something important to discuss—perhaps a problem in one of the company’s three dozen divisions, which oversee everything from top secret government contracts to the making of toilet paper. Jassy’s seventh-floor office was a panopticon of whiteboards, each one filled with endless Amazon-related to-do lists or ideas. He had so many whiteboards that his office walls were barely visible. Some of the notes on the boards were so secret that he would cover them during meetings. That day, he sat at his desk and dialed his boss. Bezos greeted Jassy with a bit of small talk—some personal, some business. Then, out of nowhere, Bezos said something Jassy never expected to hear.
“I’m contemplating stepping away from the CEO role at Amazon,” Bezos said, as recounted to me by Jassy. “I’m happy to keep doing the role, but I’ll only stop doing it if you’re excited about being the next CEO and my successor.”
“Can I think about it for a couple of days?” Jassy asked, surprised and excited by the prospect but obviously taken aback by the seemingly sudden offer.
“Of course,” Bezos replied.
Jassy is a creature of habit and tradition to an unusual degree. He meets each of his two kids, a son and a daughter, for breakfast once a week (always independently), on the same day at the same time, and has done so for years. He hosts the same weekly, monthly, and annual sports gatherings at his house. He schedules two hours for himself on his calendar once a week to read (often Amazon-related memos), and on Tuesdays, as he’s done for the past 25 years, he has a date night with his wife, Elana.
That night, seated outside at a local restaurant with plastic domes installed over each table to help separate patrons from one another, with the rain pelting down on them, the Jassys discussed the pros and cons of taking the biggest and most visible CEO job on the planet. Were he to accept, Jassy would oversee 1.4 million employees at a company with a market capitalization of more than $1.75 trillion; he would oversee the divisions that build electronics, make clothing, sell books, grow food, procure data, and dish out pharmaceuticals; not to mention continuing to oversee his brainchild, the cloud-services division, which props up most of the internet. If he chose to take this daunting job, he would be responsible for Amazon’s Alexa, Ring, and Twitch; Whole Foods Market; IMDb; ComiXology; Audible; Amazon Studios, the makers of The Boys and The Marvelous Mrs. Maisel; not to mention hundreds of fulfillment centers, a mammoth supply chain, and countless other businesses that start with Amazon: Amazon Advertising, Amazon Fresh, Amazon Drive, and on and on.
This job would inevitably lead him to be dragged in front of Congress, cameras glaring and angry politicians trying to tear him apart, where he would be forced to answer questions about Amazon’s monopolistic business practices and a slew of antitrust issues. He’d be ridiculed on TV, turned into a million unflattering animated GIFs on social media, and see his name and face shackled to the front pages of a thousand newspapers. It was a role that would put him on the front lines of the war with Amazon employees trying to form unions, where he would have to personally hold at bay tens of thousands of competitors and stave off foreign governments that want to break Amazon into a million little pieces. Perhaps most difficult of all, if he took this job, Jassy would somehow have to sustain the truly astounding growth trajectory of the company, which continues to show a 37 percent increase in revenue year over year and brings in $443 billion in annual revenue.
“I was surprised,” Jassy told me, recalling that Tuesday call with Bezos. “I wasn’t anticipating it, I wasn’t clamoring for it, I loved my current job, but I was obviously flattered and excited by the prospect.”
Sure, it had a lot of cons, but the potential pros for Jassy far outweighed them. A few days later, Jassy called Bezos back and told him, “I’m in.”
It takes a certain kind of personality to want to run one of the largest companies on the planet. Recent psychological studies have found that as many as 20 percent of corporate CEOs display psychopathic tendencies, meaning a huge percentage are thrill-seekers who feel no empathy for others and thrive on revenge. Bezos certainly has at least some of those personality traits. But Jassy, as far as I can tell, does not—at least not yet.
When the announcement went out in early February that Jassy would be taking over as CEO of Amazon, Wall Street wasn’t sure how to react. Analysts felt comfortable with Jassy as the new head of the company—as one tech investor told me, “If AWS was a stand-alone business, it would likely be valued at close to a trillion dollars”—and they were also relieved to know that Bezos would be hovering above as chairman. But while the stock rose 1 percent on the news, it did not skyrocket as, say, IBM’s did when it announced a CEO change. Sure, Jassy ran one of the most profitable segments of Amazon’s business, but Bezos, who had started Amazon 27 years earlier, formulating its massive potential on his laptop while on a cross-country road trip, wasn’t just an icon of American business, he was the icon of modern American business. Bezos was a killer—to quote Logan Roy of Succession—and it was that instinct that had led him to grow the company in limitless size and scope.
Unlike Bezos, who is as famous as an A-list Hollywood celebrity, Jassy is largely unknown beyond those familiar with cloud computing jargon like “SaaS” and “CRM.” One Amazon analyst noted that at the time of the announcement, Jassy instantly became the most googled person on earth. (Over the past couple of months, when I mentioned to people I was writing about Andy Jassy, almost everyone responded, “Who is he?”) The questions about what would happen next at Amazon were endless. Could a guy who runs a cloud computing division run all of those entities? How much more could he grow a business that was already worth almost two trillion dollars? And perhaps most important, as Amazon approached one of the most volatile times in its history, was Jassy a killer?
When I’ve written about other tech CEOs—Jack Dorsey, Mark Zuckerberg, Steve Jobs, even Bezos—there has always been a seemingly infinite line of former employees, old friends, or cofounders, usually those who felt they’d been wronged, who have been all too happy to vociferate in great detail how fucked up their old bosses were as human beings. When it comes to Jassy, though, I couldn’t find one person who could—or would?—say a bad thing about him. (And trust me, I tried.) All anyone would say was how nice and unpretentious he is.
His college roommate, Tom Salentine, told me he’d seen Jassy’s niceness back in their Harvard dorm-room days. (Once Jassy was worried that a fellow student studying for a test wasn’t eating enough, so he began leaving food by his door each night.) His older sister, Kathy Savitt, told me her brother was born nice, grew up nice, and is still nice to this day—maybe even nicer. (“He’s one of the most likable people I know.”) His friend Rich Fontaine, whom Jassy met 30 years ago at his first job selling porcelain collectibles, told me Jassy is also the most humble person he knows. (“He honestly doesn’t give a shit.”) A long list of current and former Amazonians—Rick, Jennifer, Maria, Chris, David, and so on—talked endlessly about Jassy’s nice guy–ness not only within Amazon but outside of the company as well. (He donates time and money to nonprofits for cancer research, volunteers with programs that help kids in developing countries learn how to read, and is on the board of a nonprofit that helps low-income and immigrant families gain access to higher education.)
I came away from two dozen interviews unsure if either the Amazon communications staff had cleverly debriefed everyone who had ever interacted with Jassy over the last 53 years to say almost exclusively nice things about him—which is plausible, given the way tech communications departments work—or if Jassy had indeed spent the past decade of his career only collecting admirers and making few, if any, enemies.
When I asked Jassy if he’s ever done anything wrong in his life, or if as a kid he ever got into trouble, he simply said he never had time to—he was too focused on school and sports. If you were to believe all of his friends, family, and colleagues, it’s as if Fred Rogers walked onto the set of The Office.
But even Mr. Rogers had his issues. One person who knows Jassy told me he can be so boring “you’ll want to gnaw your own arm off when talking to him.” And some employees say Jassy’s attention to detail can sometimes be maddening—that he gets into the weeds on issues far beneath his pay grade and obsesses about them. One example took place a few years ago, when a hurricane knocked out power to one of the AWS data centers. Generators had been installed precisely for a situation like this, but when an employee flung open a door to the generator room, the back of the door hit an emergency shutoff button, which took the entire data center down. According to someone who worked with Jassy, rather than just tell people to move the switch, he held countless meetings about the incident and became personally involved in deciding where in the room the switch was moved.
Which leads to the question of the work environment at AWS. In July, 550 AWS employees signed a petition that alleged “an underlying culture of systemic discrimination, harassment, bullying, and bias against women and underrepresented groups” and sent it to Jassy, as well as his successor as executive of AWS, Adam Selipsky. A letter I got my hands on that was sent to AWS employees by Selipsky noted that an outside firm had been hired “to investigate and understand any inappropriate conduct that you or others may have experienced or witnessed.” Last year, an AWS employee named Laudon Williams left the company, explaining in a LinkedIn post that the culture in his division had become toxic. In the post he recounted a story where a colleague said to him, “Amazon’s greatest strength is its ability to self-correct, and AWS is the only business I’ve encountered at Amazon that fights that self-correction.”
Jassy has not been accused directly of engaging in race and gender discrimination—but senior people he has hired over the years have. With his reputed attention to detail, is it possible he didn’t know? Amazon said that the company has begun addressing the issue by creating women-led groups within AWS and creating an anonymous ethics hotline, but the company is still waiting for the results of the investigation.
If Jassy is described today as a nice guy, his former boss was once seen that way too. While Bezos spent the first two decades as head of Amazon coming across as Jassy does today—unpretentious, with his own dowdy shirts and frumpy khaki pants, driving an old Honda Accord when he was worth $10 billion, and venerating his wife and family—something seems to have changed in Bezos as his wealth, power, and fame grew.
In January 2019, Bezos announced he was divorcing his wife of 25 years, MacKenzie Scott, and he is now rumored to be engaged to Lauren Sánchez, an entertainment reporter and helicopter pilot. Since then, Bezos has gone through a sweeping physical transformation, trading that bumpkin-like style for leather jackets and puffer vests. Many people speculate he has plumped up his lips and cheeks and possibly had some sort of cosmetic surgery. His Accord was swapped for a $70 million Gulfstream G650ER private jet. His ostentatious lifestyle will go down in history: He owns homes in Washington, D.C. ($23 million), two mansions near Seattle ($63 million), an apartment in New York City ($80 million), a compound in Los Angeles ($175 million), and a 30,000-acre ranch in Texas. He’s one of the largest landowners in America, according to The Land Report, and he is currently building a $500 million 417-foot superyacht, which will have its own little baby yacht. Then there is his obsession with space. One media publisher told me he saw Bezos as a man “going through a midlife crisis on a lunar level.” A current Amazon employee said, “Jeff seems to have left the planet, literally and figuratively.”
Unlike Jassy, Bezos’s philanthropy seems to be tepid at best. While his ex-wife, Scott, has given away more than $8 billion since their divorce, under Bezos’s leadership Amazon opposed a nominal tax in Seattle that was intended to help the city’s homeless. Years ago, it was Bezos’s decision to stop giving automatic raises to hourly workers in the fulfillment centers after three years, according to Brad Stone’s new book, Amazon Unbound, with Bezos justifying the action as a way to stop employees from becoming complacent. And under Bezos there were no air-conditioning units at a warehouse in Pennsylvania until 2012, even while some employees were reportedly fainting from extreme heat. In the face of millions of people who lost their jobs due to the pandemic, Bezos chose to take a tourist flight on a Blue Origin spacecraft this summer, and after landing successfully, in perhaps his most tone-deaf moment thus far, he thanked “every Amazon employee and every Amazon customer, because you guys paid for all this.”
So how is it, given that Bezos could have chosen anyone on the planet to appoint as the next CEO of Amazon, he chose almost his polar opposite to run the company?
Well, it seems, that was the point.
In early 2010, Steve Jobs, the CEO of Apple, made a secret pilgrimage to a handful of newsrooms across the country to talk candidly about his business. In one such meeting at The New York Times with a group of editors, I sat across from Jobs as he talked about the iPad and his competitors. Curiously, Jobs said he worried about Google encroaching on Apple’s turf, but he did not worry about Microsoft. When I asked why, Jobs said: “When [Bill] Gates stepped down, he put a sales guy in charge of the company, and the only way to ruin a company is to have a sales guy running it. What he should have done is put a product guy in charge.” The sales guy Jobs was referring to was Steve Ballmer, a boisterous Pierrot who would end up missing one opportunity for Microsoft after another: the smartphone, the tablet, social media. (It wasn’t until Microsoft replaced Ballmer with Satya Nadella, a “product guy,” in 2014, that Microsoft started to flourish, growing into a $2.2 trillion company.)
Choosing a successor can be one of the most difficult decisions a CEO makes, especially for a business still run by its founder. The right choice can mean astounding growth and a legacy for the history books; the wrong one, the near-annihilation of a company. Jack Welch, for example, who ran GE from 1981 to 2001, was considered one of the greatest CEOs of his generation, amplifying the company’s market capitalization from $14 billion to $410 billion by the time he retired. The tenure of his successor, Jeff Immelt, led GE to near-collapse, its stock falling 30 percent as the S&P 500 rose by 124 percent. (Immelt famously had an extra private jet follow his primary private jet when he traveled in case he ran into delays, even as GE laid off thousands of workers.) When Jobs stepped down as CEO of Apple in 2011, he didn’t follow his own advice because he couldn’t find a product guy who was also a business guy. So instead he chose to appoint Tim Cook (whom Jobs had once described as “not a product guy”) to run the company and Jony Ive to design the products. According to an adviser to Jobs at the time, Jobs knew that Cook, an operations genius, would be able to grow Apple with its product line into a global behemoth. Indeed, Jobs was right (again); Apple is now worth $2.55 trillion and is the biggest company on the planet.
For Bezos, the decision was different.
Amazon could tell it was potentially in serious trouble over the last couple of years as Donald Trump found one topic on which to agree with his extreme antipodes in government—Bernie Sanders and Alexandria Ocasio-Cortez—that Amazon was too big and needed to be put in check. Ocasio-Cortez has accused Bezos of paying his workers “starvation wages,” Sanders has slammed Amazon and talked up the need “to take a look at the power and influence that Amazon has,” and Trump, while in office, inveighed against Bezos, Amazon, its power, and tweeted that “they pay little or no taxes to state & local governments.” Last year, Bezos was hauled before the House Subcommittee on Antitrust, Commercial, and Administrative Law, which turned into essentially five hours of lawmakers berating Bezos and the heads of Alphabet, Facebook, and Apple for their anticompetitive monopolistic practices. And that was just the start. The Federal Trade Commission is currently investigating Amazon’s business practices around snuffing out competition in retail and Jassy’s AWS division. The company also faces antitrust inquiries by attorneys general in New York and California, and the Department of Justice is looking into a broad antitrust review of Big Tech. That’s just in the United States. India, the United Kingdom, and Germany, among others, are probing Amazon for antitrust issues. In June, a bipartisan bill was proposed in the House that would effectively force Amazon to be split in two or close down its private-label businesses, in which the company makes its own branded products.
The peak of all of this for Amazon is obviously yet to come, with investigations, bills, and hearings just heating up. But back in 2018, as he was firing up the rocket boosters on his lunar-level midlife crisis, according to one person close to the company who knows Bezos and Jassy, Bezos foresaw what the next decade for Amazon would look like and knew that not only did he want to pursue other passions, but most important, he was no longer the right person to be the face of the company. Even Bezos had the self-awareness to recognize that the richest man on the planet, who owns more than a billion dollars’ worth of homes, planes, and yachts, whose laugh evokes Dr. Evil, would not be the best witness to place in front of Congress when arguing that Amazon is indeed not an antitrust threat and a monopoly and that it does not pay its employees “starvation wages.”
There was really only one other person at Amazon, a true blue Amazonian, who was not only capable of running the entire empire but also came across as a nice, unthreatening guy, just like you and me.
Andy Jassy.
Jassy is already formulating how he will respond to these issues in front of Congress. His answers to me on these topics were buttoned up and articulate, media trained and ready for prime time. “In our retail business, if you look at the size of business relative to the global retail market, we have about 1 percent of the total global business,” Jassy told me when I asked how he plans to respond to Congress. “It’s a big business, and Walmart is a larger retailer than Amazon, but still, we only have about 1 percent of the global retail market share.” Will these statistics be enough to stave off a battalion of government lawyers trying to break up Amazon? Probably not, but there have long been rumors in business circles that Amazon actually wants to be broken up. “AWS could be one of the top 10 biggest businesses on the planet if it was spun out of Amazon,” an investor told me. “If the government breaks them up, they will just make more money—the government thinks they’re so smart threatening to do this, but it’s what Amazon wants.”
While Amazon might be fine being broken up, one thing it definitely does not want is to be unionized. The company has a history of harassing employees who even discuss unions in its fulfillment centers, including, reportedly, spying on organizers. Many of these issues came to a head earlier this year in Alabama, where, after a long and very public struggle, warehouse workers ultimately voted against unionizing—following an aggressive pushback from the company, including mandatory “information sessions” and an anti-union text message campaign.
Jassy’s got the union talking points down pat too. He rattled off a list of all the things Amazon has done around safety and improving employee pay. “We pioneered, especially in the United States, raising the minimum wage to at least $15 an hour, with full benefits, insurance, 401(k), and 20 weeks of maternity leave,” he told me. He used that old line—that unions are not up to him but to the Amazon workers—but also confessed he believed that unions might not be best for Amazon’s business. “Personally,” he said with a brief pause, “I think the thing about a union is that it just makes it harder to move faster and to be nimble.”
Stuart Appelbaum, president of the Retail, Wholesale, and Department Store Union, told me that in 2019, when Amazon was exploring opening its second headquarters in New York City, it was the possibility of a union that was stalling the effort. On a bitterly cold Wednesday afternoon, then governor Andrew Cuomo called a meeting with the top brass of Amazon (people who reported to Bezos); a group of union leaders, including Appelbaum; and other government aides in his conference room in New York. Cuomo desperately wanted Amazon to set up HQ2, as it was called, in New York City for the potential job opportunities, and he was determined to broker a deal between Amazon and the unions. After hours of negotiations, the two groups agreed to a middle ground, which Appelbaum described as “a weak deal, but it was one we all agreed on,” that would allow organizers to start a tepid union at best, and in which Amazon agreed not to retaliate against people who wanted to unionize. “We all shook hands and agreed on the deal,” Appelbaum told me. “Then the next morning Bezos announced he was walking away from New York.”
When I asked if union organizers he had spoken to believed Jassy would act the same way, Appelbaum laughed. “It’s still Jeff Bezos’s company, and all major decisions are going to be run by him no matter who has the title of CEO,” he said.
Being CEO of one of the biggest companies in the world was never a dream job for Jassy. After growing up with two very normal parents (his father was a lawyer, his mother a trustee at a theater company) in Scarsdale, New York, Jassy made his way to Harvard with one hope and one hope only: to be a professional athlete. He first played tennis, then soccer, but when he realized in college that he simply didn’t have the build or skill to play professionally, he was determined to stay in sports. He tried to be a radio sportscaster. When that failed, he tried to be a TV sportscaster, which also failed. He then tried to manage a rock band, which didn’t work out either. And finally, he worked for a collectibles company selling porcelain keepsakes. These failures ultimately led him to business school at Harvard and, by chance, to Amazon. (In 1997, when Jassy was at Harvard Business School, an Amazon recruiter was unable to fill her interview slots because so few people at the university knew what Amazon was, so she cold-called Jassy after finding his résumé in the career office.)
More than two decades later—Jassy told his wife he thought he’d only last three years in Seattle—sports has remained a mainstay of Jassy’s passions. Sports are so important to him, in fact, that he built a sports bar in his basement that he calls Helmet Head, which, he likes to brag, has seven TVs. He’s so obsessed with sports that when I went through years of his likes on Twitter, I found videos and tweets about baseball, basketball, college basketball, football, college football, volleyball, soccer, mountain biking, golf, even whiffle ball. (And he even liked a couple of tweets about locker rooms.)
But while he gave up playing sports (at least professionally), that competitiveness never really left him, and perhaps the competitive streak is what got Jassy where he is today. During our conversation, the two times he seemed to get most excited were when he talked about the importance of customers—he said customer dozens of times in a one-hour conversation, uttering corporate poetry like “We’re pretty clear-minded, that for us, we exist to help solve problems for customers, and to make their lives better”—and when he talked about Amazon’s competitors. “You always want competition,” he said with a little extra pep in his voice. “It’s good for consumers…it’s good for opportunities, and it’s good for the economy.”
Indeed, Jassy makes everything a competition.
His sister told me that when he was six, he was so intent on winning board games with her older friends that he obsessively studied the rules of Monopoly and Clue, then mastered the games, just so he could take on, and beat, her 10- and 11-year-old friends. He used to invite coworkers into his office each morning to play a game he called the Ledge, where Amazonians would stand across from one of Jassy’s many whiteboards and try to land a dry-erase marker on the ledge (he kept a running scoreboard behind his door). And everyone—and I mean everyone—I spoke to about Jassy spent a good portion of the conversation talking about Jassy’s “wing eating contests,” which he calls Tatonka (named after the word for buffalo in the movie Dances With Wolves). The annual competition, which Jassy originally hosted at the Wing Dome restaurant in the Greenwood neighborhood of Seattle, includes “wing referees” (who wear black-and-white striped jerseys) to inspect bones for any leftover meat and offers a vegetarian segment with celery sticks. In typical Jassy fashion, he created competitions within the competition. One of these is where participants weigh themselves before and after the tournament to see who has gained the most weight during the contest. Rick Dalzell, who worked with Jassy for two decades at Amazon, told me that he once watched Jassy, so intent upon winning, eat so much that he ran out of the room because he was going to vomit.
Jassy has clearly used that competitive streak to grow AWS to the behemoth it is today, and is now going to try to make Amazon the biggest retailer on the planet. From people I’ve spoken to at the company, it appears that Amazon has hopes of overtaking Walmart sometime next year, as well as trying to stave off lawmakers.
But at what cost? Will Jassy be so obsessed with winning that he’s oblivious to the plight of women and underrepresented groups at Amazon? Will he be so concerned with “moving fast” and remaining “nimble” that he pushes workers in fulfillment centers until they faint and have to be taken out on stretchers so that we, his darling customers, can get a roll of toilet paper more quickly? Will he be okay with delivery drivers urinating in bottles in order to meet their quotas? Will he shrug his shoulders and appear publicly not to give a shit, as his predecessor did, when he continues to destroy Main Street and mom-and-pop shops, even more than Amazon already has? Will he still be a “nice guy,” or—as happened to someone he knows so well—will he change?
Toward the end of my interview with Jassy, I noted that in many respects, he looks a lot like Bezos did when he started as CEO of the company back in 1994: unpretentious, unaffected by money, and not yet world-famous. I pointed out that over the past two decades, tech titans like Zuckerberg, Jobs, Bezos, and Gates have become household names. Over the next five years, Jassy will become one of them. He will be on the cover of newspapers and magazines, his face will be projected across television screens around the globe. He will become a superstar.
“When you have that amount of wealth and that amount of fame and you have everything, it affects you,” I said, pointing to what’s happened to people like Gates, whose marriage fell apart because of his philandering, or Jobs, who thought he knew better than his doctors and refused a potentially lifesaving surgery in favor of a fruitarian diet. I wondered if he thought, perhaps presciently, that being the CEO of Amazon will change him as it clearly did Bezos.
“Does that worry you? Do you think it will change you in any way?” I asked.
He thought for a brief moment and then told me, “It does not worry me, mostly because I think I know who I am. I know that there are a number of things I haven’t encountered and I’m sure I’ll encounter over time,” he said, “but I feel grounded in who I am and what matters to me, and I’ll remain true to that.”
One thing is for sure: The entire world will be watching.
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