The first time I met Jeff Bezos, I asked him what he was wearing.
It was the spring of 2016, and I had been hoping to sit down with the then-CEO of Amazon before he appeared onstage at an annual tech event hosted by my employer at a California cliffside resort. At the time, I had been reporting on Amazon for three years but still hadn’t met Bezos other than a passing hello as he was whisked out the door at a different conference two years earlier. As disappointing as that was, it was not all that surprising. As Bezos’s wealth and fame ballooned, his PR team shielded him from the journalists who knew his company best. I can’t say I totally blamed them: the Amazon story was splintering away from a pure, feel-good tale of great American ingenuity into a narrative with more complicated offshoots, and he or his advisers seemed to have determined that avoiding the toughest conversations was the smart move.
So, when I was told by Amazon’s PR department that a meeting wasn’t going to happen, I decided to make my own meeting by waiting for Bezos backstage. I wasn’t planning to ambush him; I was simply looking to strike up a conversation that might create an opening for more substantive discussions down the line. As the event approached, I strategized about what my opening line should be; I knew it would only be a matter of time before his security team or his PR handlers made my life difficult. Then I got some inspiration: Fortune magazine had recently ranked Bezos No. 1 on their 2016 list of the fifty “World’s Greatest Leaders” and, in the accompanying profile, the famous entrepreneur mentioned one of the new Amazon initiatives in which he was most interested: the company’s foray into private-label clothing—basically, clothing lines that Amazon would source, brand, and sell itself. Not necessarily the sexiest of product categories, but one that my nerdy retail brain was also interested in, so I decided to latch on.
With that in mind, I thought I might succeed both at showing Bezos that I was paying close attention and at making him laugh if I opened with something like: “Hey, Jeff. I’m Jason Del Rey from Recode. I recently read that you are spending a lot of time on Amazon’s private-label business. Are you wearing any Amazon brands today?”
On the day of the event, Bezos stood alone backstage, watching the onstage interview that preceded his from a monitor. He was dressed in a dark blazer, dark denim jeans, and light-colored button-up, along with brown leather dress shoes. I walked over and shook his hand as I introduced myself, and then delivered some version of the lines I had planned out in my head. After digesting my question for a moment, one of the world’s richest men shot back with two questions of his own.
“Did you just ask me what I was wearing?” he deadpanned. “Am I on a red carpet?”
I waited for his mouth to crack into a smile or for him to unleash his trademark booming howl. Neither happened. Instead, one of his PR handlers must have sensed his unhappiness from afar and raced over to intervene.
“Did you just ask Jeff Bezos what he is wearing?” the spokesperson shrieked as Bezos retreated, I assumed, for good. I tried to explain the context, but it didn’t seem to register. Much to my surprise, though, Bezos returned a short while later, after helping himself to a nonalcoholic drink.
“What are you wearing?” he volleyed back. I explained, awkwardly, that my outfit was selected by a stylist working for a service called Trunk Club, an independent startup that had sold to Nordstrom in 2014 for $350 million. I didn’t mention that my sister had gifted me the service (in part because she knew I was a terrible decision-maker and in part because I needed to step up my fashion game in advance of hosting a new conference of my own). What I did reveal to Bezos was that the service required that you trust the advice of a random human to pick out your clothes—one undoubtedly with some type of fashion sense, but perhaps not exactly your fashion sense.
Aha, Bezos said, nodding along. I wondered what the person who had reinvented bookselling, then blown up the entire retail landscape through digital commerce, thought of a rather old-school approach. Leave it all to humans? For innovators like Bezos, wouldn’t the ideal service use technology to outsmart humans? Bezos explained that his preference would actually be a combination of both: computers to provide a selection of algorithmically generated clothing options, which a human stylist would then filter to make the best, final choices. At the time, another startup, called Stitch Fix, was offering a version of that service. But sure enough, in 2019, Bezos’s idea would manifest itself when Amazon unveiled a rival service of its own.
Bezos then excused himself to take the stage, but his words lingered. It was just one of many examples where Bezos had crafted a vision of Amazon’s future that seemed outlandish—Amazon, a fashion stylist?—only to become a service years later that at least some found appealing. Not all of the crazy ideas would pan out; but many did, and in industry-shattering ways. He and his deputies had done it with bookselling; then cloud computing with Amazon Web Services; video streaming with Prime Video; voice assistants with Alexa; grocery delivery with Amazon Fresh; and now he was trying it with fashion, too—no matter the critics or the risk of failure. His penchant for cooking up wild ideas, but then bolting them down with technology and operational rigor, had helped transform his company into a global powerhouse, even if the fashionistas or incumbents in other industries he infiltrated turned up their noses—at least initially. Walmart chief among them.
My discussion with Bezos, though, also reinforced a few other things I had learned about the way he and his company were evolving. On one hand, the company’s avoidance of an initial meeting with me, plus the terror that appeared to overcome the PR rep when they realized I was speaking to Bezos without preapproved permission, confirmed that Amazon didn’t want to have tough conversations—at least not with informed outsiders who understood both the good and bad of the company’s business and labor practices. It was, as retail and PR industry veterans had long told me, a similar approach that another high-flying industry titan had once taken: Walmart.
Of course, before Amazon came along, Walmart was the big bad bully of retail and American capitalism, with a reputation for squeezing suppliers until they moved operations to cheaper labor overseas, paying its workers next to nothing, and decimating mom-and-pop shops while plundering their local communities for tax breaks. While Walmart was a savior to tens of millions of Americans who sought its bargain-bottom deals, others viewed it as Public Enemy No. 1. But after decades of ignoring or dismissing top criticisms—founder Sam Walton himself said in his 1992 memoir, “I don’t want to be too critical of small-town merchants, but the truth is that a lot of these folks just weren’t doing a very good job of taking care of their customers”—the company’s third CEO, Lee Scott, chose a different path in the mid-2000s. He sought out and listened to critics, whether outside groups or reporters, and even agreed with some of them.
“Over the last couple of years I’ve been spending much of the time talking about all the negative publicity we’ve been getting, not from the standpoint that we hate the press, but by asking our people what we are doing that allows people to perpetuate these kinds of negative discussions about Walmart,” Scott said in 2005.1 “We can’t just fall back on the idea that we should have some leeway because we don’t mean to do any harm. We’re going to be judged on how we react to racism, or sexism, or these other issues when we find them going on, and I tell everyone we have to react more dramatically and in a less forgiving, harsher way to behaviors that don’t measure up.”
Self-serving or not, there seemed to be a conscience growing inside Walmart that was mostly invisible to outsiders in the first few decades of the company’s rapid growth. Yet in the years that followed, as similar waves of scrutiny crashed ashore in Amazon’s backyard, the tech giant did not seem to have learned from Walmart’s approach. Amazon had in many ways become Walmart 2.0, for better or worse. One could argue that the company’s immense selection and low prices were at least as devastating to competition as Walmart was. Plus, Amazon added a third ingredient to its cocktail of innovation and competitive destruction: one-click shopping coupled with speedy delivery. But the company’s famed “customer obsession” was not accompanied by the same level of employee obsession, which meant a grueling pace and meager wages for workers. That, in turn, transformed Amazon into a natural target for unions, labor activists, and concerned lawmakers as well.
“There is just blanket dismissal of any criticism being real,” US congresswoman Pramila Jayapal, whose district includes Amazon’s hometown of Seattle, once told me, referring to Amazon’s usual response to critics. “There isn’t really the opportunity to say, ‘Here are things I’m hearing, things being reported and what is the response?’ The response is almost always, ‘That is ridiculous, this is a conspiracy, and someone is out to get us.’”
* * *
But Bezos’s comments to me about a better solution to an old-school retail problem also reminded me that he and his company did not totally disregard the old ways of doing business. He wanted to take those practices, turn them perhaps 90 or 180 degrees, and infuse them with technology if the company believed the result would be cheaper, smarter, or otherwise better. Bezos and company didn’t despise traditional retailing; they thought it could be a whole lot more convenient for the people who they believed should matter most: customers.
Again I was reminded of Sam Walton and the retail goliath he built from Walmart’s headquarters in Bentonville, Arkansas, and out across small-town America. Walton and company didn’t upend the retail industry in the 1980s and ’90s by demolishing it and inventing something altogether new; instead, they reinvented it. Walton’s memoir is full of odes to the inventions and tactics from competitors he happily borrowed from: cash registers up front from Ben Franklin stores and loss leaders or “image” items from early discounters like Gibson’s. Checking out the competition was one way Walmart “tried hard to make up for our lack of experience and sophistication,” Walton wrote. (A look at Amazon’s famed “Leadership Principles” shows Jeff Bezos’s company also borrowed ideas from the titan of physical retail. At least two of Amazon’s original fourteen corporate tenets were inspired by Walton’s Walmart culture: Bias for Action, and Frugality.)
But despite Walmart’s onetime appreciation for competition, the go-go Supercenter-building sprees of the 1990s and 2000s opened up blind spots. The top-down centralized operating structure that allowed for the precision and ruthless execution of the Supercenter rollout seemed to lessen the appreciation for competition—at least in a new digital world. There was no time for it. Walmart leaders were consumed by the massive revenue and profits associated with its Supercenters, and mostly ignorant to the threat and promise of the internet.
In a way, Sam Walton feared a future like the one Walmart was barreling toward. He wrote of the danger of morphing into a “centrally driven chain, where everything is decided on high and passed down to the stores.”
“[I]n a system like that,” Walton wrote, “there’s absolutely no room for creativity, no place for the maverick merchant . . . no call for the entrepreneur or the promoter. Man, I’d hate to work at a place like that, and I worry every single day about Walmart becoming that way.”
By 2014, when a forty-seven-year-old company lifer named Doug McMillon became Walmart’s fifth CEO, Walton’s fears had largely come true. So McMillon would make a giant bet on a new generation of entrepreneur and promoter to help rescue the traditional retail titan from an Amazonian attack.
* * *
On the morning of March 4, 2022, I found myself seated at a blue plastic picnic table outside an indistinctive squat brick building in the northwest corner of Arkansas. This was the home of Walmart, the greatest disruptor that the United States retail industry had ever seen—until a certain upstart two thousand miles to the northwest began carving off a little bit of customer spending here, and a little bit over there, until no responsible competitor could ignore it any longer.
On this day, I would be visiting with the man charged with holding onto integral pieces of Walmart’s past while choosing wisely where to adopt from those leading into the future. Doug McMillon was handsomely compensated for this job—north of $20 million annually in cash and stock. But his task was not easy. While Jeff Bezos and the rest of his company had spent the 1990s and early 2000s bending the retail industry to their will, Walmart had long treated online commerce as a cute side project, establishing a separate headquarters in Silicon Valley, where it was easy for Walmart’s leadership team to sometimes forget that it even existed.
It’s hard to reject your own DNA. And Walmart’s DNA was built around in-store sales and heavy profits—two things that Amazon rejected for much of its history. While Walmart trained Wall Street to regularly expect profits, Bezos preached the opposite message. We are investing in growth instead of profits, he told Wall Street, but someday when we have snapped up enough market share, we promise we’ll have tons of excess cash to show for it. That was Amazon’s long game and Wall Street investors gave the company a very long leash. Amazon was also able to exploit a tax advantage over its brick-and-mortar rivals for the first decade and a half of its existence that only helped. Amazon was a nimble, fast-moving giant, while Walmart’s profit-heavy success, and expectations from investors demanding more of it, gave the traditional retail titan less flexibility.
But McMillon was determined to awaken Walmart from its digital slumber and acknowledge the existential threat that Amazon posed. Along the way, he had to drag many Walmart lifers toward a new future, which could be an uncomfortable one. The symbols of this attempted transformation were evident beyond Walmart’s walls and all over Bentonville on my visit. On the day before my meeting with McMillon, I met a top Walmart official for a patio lunch at BlakeSt., a members-only club housed in a renovated 1887 farmhouse developed by one of Sam Walton’s grandsons. In the background, a member did laps in the temperature-controlled outdoor pool. Someone called it Bentonville’s version of Soho House.
From BlakeSt., or really any downtown Bentonville location, construction cranes were a common sight, reminding me of a scaled-down version of the controversial boom in Seattle that some longtime city residents have blamed Amazon and its ascent for. As my gaze shifted up and out the window during one Lyft ride across town, the driver put it best: “More buildings, more homes, more everything.”
One major component of the “more everything” boom was a brand-new Walmart campus beginning to take form. It was around 350 acres in total, with a long menu of amenities aimed at attracting a new type of professional that McMillon and company desired to continue to modernize the company and defend against the Amazon attack. Among the new perks was one that caused employees to do a double take, and its CEO thus needing to mention twice.
“You’ll see improved parking, meal services, fitness, and natural light—yes, natural light,” McMillon wrote in announcing the opulent new campus in 2017. The Walmart “home office,” on the other hand, originally opened in 1971 and was once best known for its bare-bones aesthetic and, as McMillon’s note hinted, a dearth of windows. But how would Walmart’s new home reflect on traits the company had long been proud of, company long-timers wondered?
“To what extent does that now mean that you don’t own frugality—that suppliers aren’t going to walk in and say, ‘Hey, these guys aren’t messing around?’” Marcus Osborne, a former longtime executive in the company’s health care division, said of the new office plans. “To what extent does it sort of take the focus off the customer?”
“When you’re sitting in the old home office,” he continued, “all you had were these nasty cubes, but you saw merchandise everywhere, and it was just—you were surrounded by this stuff. And it forced you to—we were constantly reflecting on customers. I think that’s where this is going to be a challenge. And I see it for a lot of companies, but I think it’s going to be the hardest for somebody like Walmart, because of its history and legacy.”
Yet some kind of Walmart transformation was necessary and long overdue. Amazon made sure of that. It first attacked Walmart in general merchandise—from books to electronics. Then it went after Walmart’s core grocery business, both in the digital world and later the physical world. Along the way, the tech giant carried out a yearslong offensive to convince Walmart’s most valuable customers to defect to Amazon Prime. Not all efforts were successful, but the pace was unrelenting. For the first time since the launch of the Supercenter, Walmart was on its back feet. Walmart, “Everyday Low Price” stalwart, destroyer of any and all competition, was finally an underdog.
For many years, Walmart leaders didn’t even acknowledge this, in part because Sam Walton’s and Jeff Bezos’s companies operated mostly in separate spheres—one a massive brick-and-mortar retailer, the other an online giant. But in 2016, Walmart aggressively moved into the world of e-commerce, while Amazon would soon make big bets on physical retail. The resulting rivalry was a no-holds-barred power struggle for dominance as Amazon’s ambition only grew and Walmart’s homegrown CEO attempted a business reinvention for the ages.
Along the way, retail experienced an unprecedented shift accelerated by the Covid pandemic. Customers moved more of their purchases online and began expecting more convenience from physical retailers, while mom-and-pop stores and once-prominent chains alike were being wiped out or forced to do business with industry giants. Amazon and Walmart reaped the rewards, with the two accounting for nearly $1 out of every $2 spent online in the US. But as the two megacorporations have consolidated retail power, troubling consequences have also emerged—for consumers and small merchants facing fewer buying and selling options, and millions of workers paid meager wages for demanding and sometimes dangerous work.
For the last ten years, I’ve been covering this battle between Amazon, Walmart, and other upstarts that have tried to contend with these behemoths of global retailing. I’ve done it in hundreds of written articles for Recode; a hit documentary podcast called Land of the Giants; and my own annual confab for industry heavyweights, called Code Commerce. Through that work, I’ve spoken with thousands of people who have insights into how and why these two goliaths operate the way they do, up and down the power spectrum; from $15-an-hour employees struggling through their first week on the warehouse floor to small-town merchants who depend on the platforms for their livelihood, to executives making decisions that impact hundreds of millions of people around the globe. That credibility helped me persuade both Amazon and Walmart to agree to interviews with many of their top decision-makers between 2021 and 2022. But this is not a book of access; history is written from many sides, and their side of the story provides just one point of view. As a result, I also spoke with other current and former executives, employees, and industry insiders—more than 150 in total—to provide a holistic view of the events in the hundreds of pages that follow.
The result is the story of the defining business clash of this generation—a battle waged for our loyalty and wallets, with hundreds of billions of dollars at stake and millions of jobs on the line. It’s the story of two industry titans dueling to become the go-to provider of any product you could imagine for hundreds of millions of people worldwide. It’s the story of legacy-defining multibillion-dollar bets to try to win—at all costs.
But this is also a tale of ego and revenge, with legendary executives and ambitious entrepreneurs battling to invent the future—sometimes between rival companies and sometimes within the same company walls. As both companies continue to expand their respective empires into new susceptible industries, my hope is that this account will serve for decades to come as the key to understanding how Amazon and Walmart are changing the way we shop, live, and work—for better or worse.