Marc Lore and his cofounder, Vinit Bharara, could not believe what they were hearing. It was the fall of 2010, and the two entrepreneurs who ran Diapers.com were seated across from a group of irate Amazon.com executives in a private corner of a trendy restaurant in New York City’s Meatpacking District. On first glance, Lore might have been confused for a distant cousin or East Coast version of Jeff Bezos, a business leader he long respected from afar. Both men suffered from male-pattern baldness, which they treated with close buzz cuts. Each, at that time, also favored a uniform of button-up shirts—Lore’s untucked, while Bezos kept it contained—distressed jeans, and casual dress shoes. Lore’s huskiness and New York–ese accent lent him a slightly harder edge. The truth, however, was that he was a softie who avoided discord like he did a normal nine-to-five job.
Lore’s cofounder and childhood friend, Bharara, had just returned to the table from the restaurant’s bathroom and a stop at the bar to grab a glass of prosecco, which he often drank in place of dessert. Bharara then finally built up the courage to share some news he’d been sitting on: a top Walmart executive had phoned the entrepreneurs earlier in the evening with an offer to buy their startup for around $650 million. The problem? The Amazon executives at the table were in town to finalize their own impending acquisition of Diapers.com and its parent company, Quidsi—for about $100 million less than Walmart was now offering.
Nine times out of ten, such a decision would be a no-brainer for entrepreneurs on the precipice of their first big payday: take the Walmart money, obviously. But the Amazon executives were not going to make the decision easy. The Amazon team, with tempers perhaps lubricated by an evening’s worth of adult beverages, lit into the Quidsi cofounders, suggesting that Amazon would slash prices even further to crush Diapers.com if they accepted Walmart’s offer. Amazon had already cut diaper prices by 30 percent in recent months, and now the executives at the table were promising to increase those discounts to insurmountable levels for a startup that was just squeaking out single-digit gross margins on diaper sales, even without a discount.
The next morning, the Amazon execs and the Quidsi cofounders met at the startup’s Jersey City, New Jersey, headquarters to continue due diligence in advance of the anticipated closing of the deal. But the events of the prior evening had made an impression. Lore was a highly ambitious entrepreneur, but soft-spoken and conflict-avoidant. To him the dinner-table threats felt like the corporate version of a mafia maneuver: align with us or suffer our wrath. While the Quidsi founders had been left almost speechless by those threats, they shouldn’t have been altogether surprised. Lore had long been a student of Amazon and the Bezos way, devouring every one of the company’s annual 10-K filings and referring to the Amazon CEO internally as “sensei.” Those documents, and insights gleaned by rabid media coverage of the e-commerce giant, told Lore everything he needed to know about Bezos: he was laser-focused on the quickest path to total retail domination. And Lore and Bharara were standing in the way.
In the late 2000s, Diapers.com was a hit in big urban markets like New York City and San Francisco, offering next-day delivery to a new wave of busy working parents who were both digitally savvy and craving convenience. Lore and Bharara knew that fast shipping—within at least two days, as Amazon’s Prime service offered—was the key to convincing people to order online rather than making a trip to a nearby store.
In some cities, Diapers.com was beating Amazon on delivery speeds by a full day. Their goal was to break even on diaper sales and then make money on upselling parents on more profitable merchandise like car seats and baby shampoo. But after years of rapid growth, Diapers.com had run into trouble. Threatened by the rising popularity of the upstart diaper website, Amazon executives implemented a lethal attack: a 30 percent price cut on all diapers on the giant e-commerce site. Amazon was willing to lose money on diapers in order to drive a competitor into the ground. The move was ruthless. The move seemed like pure Jeff Bezos.
Amazon’s executives knew that Diapers.com was burning cash fast, spending heavily on a successful cocktail of marketing, express delivery, and excellent customer service. And so the price cuts were meant to make life really, really hard for Lore and Bharara. They did. The entrepreneurs were left with a choice: take the risk of spending time trying to secure more capital from venture capital investors—which would be tough under the circumstances—or sell the business to a bigger company before their growth completely stalled. Years later, Lore admitted that the 30 percent price cuts did not feel like normal, above-the-board competition. “It felt very unfair,” he told me.
But in late 2010, Lore and Bharara didn’t have a ton of options and, for the first time, they were forced to seriously consider selling. They first spoke with Walmart, which had a new e-commerce leader and a renewed desire to make a big splash in the space. Walmart executives in favor of buying the startup loved the fact that Diapers.com had established a real connection with its customers that didn’t revolve solely around low prices like Walmart’s did. The fact that Lore and Bharara had managed to do this in a category as important to Walmart as diapers and other baby products was a huge plus, too. Of course, the startup’s e-commerce technology chops would also be a boon for Walmart, whose technology capabilities trailed Amazon’s to an embarrassing degree.
Walmart ended up making an initial lowball offer to buy Quidsi, but it left Lore and Bharara disappointed and determined to get Amazon involved. The pair flew to Seattle to discuss a potential deal with Bezos. A few weeks after the meeting, while Walmart appeared asleep at the wheel, Bezos gave one of his top dealmakers the go-ahead to purchase Quidsi. Amazon ultimately offered to purchase Quidsi in a deal valued at $540 million,1 and gave the entrepreneurs mere days to sign a letter of intent that would kick off a thirty-day exclusive negotiation period to conduct due diligence and finalize the transaction.
When the Quidsi entrepreneurs notified Walmart of a potential sale to another large retailer that they could not name, the executive who took the call sounded truly stunned, according to a person familiar with the details of the conversation. Shortly after the exclusive negotiating period between Amazon and Quidsi began, Walmart’s top e-commerce executive called the entrepreneurs with the $650 million offer on the same day as the fateful New York City dinner. The founders considered bailing on Amazon despite the dinner-table threats, yet they needed assurance from Walmart that the $650 million deal was a sure thing. But when Walmart sent over written deal terms, they contained a clause that gave the retailer an out if there was a material adverse change in Quidsi’s business before the transaction was finalized. Basically, the provision gave Walmart the option to back out of the deal if Quidsi’s business tanked before the government approved the acquisition. While the clause was standard in M&A agreements, it left just the sliver of doubt needed to help tilt the decision in Amazon’s favor. Plus, Lore and Bharara weren’t exactly thrilled about the prospect of telling their young coastal staff that they would soon be working for an old-school, Arkansas-based retailer.
What’s more, the entrepreneurs weren’t willing to find out if Amazon and Bezos’s deputies were bluffing on the idea of an all-out price war; they accepted the Amazon offer, giving Bezos a huge victory while crushing the hearts of Walmart leadership. The sale to Amazon made the founders tens of millions apiece and allowed Diapers.com to remain a separate entity with the founders running it, but Lore would later claim that he had felt depressed that Bezos’s questionable tactics had succeeded and that Quidsi had sold out. Even so, he and Bharara were still determined to make the most of the opportunity to learn from a company that they had long tracked and, in many ways, still admired. But they never quite fit in at Amazon. Bezos and his executives seemed to have good intentions when they decided to keep Quidsi intact as a stand-alone subsidiary after the sale. But that meant that Diapers.com continued to compete head-to-head with Amazon even under the same parent organization, and neither side ever truly agreed on the right, differentiated value propositions to customers.
Lore was also miffed when Amazon leadership declined his requests for a substantial marketing budget that he thought necessary to get in front of more young, digital-savvy parents who would help the Quidsi portfolio of shopping websites live up to its full potential. He also struggled to accept the vast chasm between each company’s approach to workplace culture. Bezos preached a religion of brutal honesty to his leaders, no matter the impact on personal feelings. Lore, on the other hand, wanted to win, but also liked to be liked—and to make sure others felt appreciated. But that just was never going to be the Amazon way. So, in 2013, less than three years after being acquired by the company, Lore and Bharara left Amazon, and their baby Diapers.com with it.
Months later, my sources began to whisper that Lore was up to something new in e-commerce. “A big swing,” as one person described it. Lore wasn’t interested in talking, as he made clear to me, politely, when I phoned him for more information, but he promised he would let me know if that changed.
If Costco and Amazon Had a Baby
Lore’s new startup would turn out to be Jet.com, an e-commerce firm that raised more than $200 million in venture capital before it even launched to the general public. The Jet model involved online shoppers paying an annual $50 membership fee in exchange for the best prices on the web, across product categories as varied as electronics, toys, and fashion.
“We always said that if Costco and Amazon had a baby, it would be Jet,” said Liza Landsman, Jet.com’s former chief customer officer, who oversaw marketing, analytics, and the customer experience.
The Jet discounting structure, however, was not simple to implement on the backend nor easy for customers to understand. Some of the savings for customers were supposed to come courtesy of the retailers and brands that sold goods on Jet.com; they’d pay commissions to the startup to list products on the site, and Jet would kick most of those fees back to customers in the form of savings.
Jet also tried to lure shoppers with unconventional methods that would allow them to receive even lower prices: shoppers could earn price cuts if they purchased multiple items in a single order—Jet called this feature the “Smart Cart”—and larger savings if the goods were all shipped from the same warehouse. Jet’s executives described these moves as “stripping costs out of the system.” In their eyes, these were savings that were hiding in plain sight in the warehousing and shipping operations that powered any online retailer. They believed that if you passed on some of those savings to customers, you could train them to order more items at once, potentially bringing down shipping costs, too.
“It’s not like we’re smarter with the way we ship stuff,” Lore once said.2 “We’re really just exposing the true underlying economics. And when we make that transparent to the consumer in discounts, we’re creating in effect more efficient orders.”
The savings didn’t end there. Shoppers could also earn additional, smaller discounts if they agreed to use a debit card instead of credit, or waived their right to return the item.
Between the savings from the brand commissions that Jet would pass along to customers, plus the “smart cart discounts,” the startup estimated the average shopper would save 10 to 15 percent per order, or $150 annually.3 Building this new type of business model, and recruiting customers who got it, was an uphill battle—and an expensive one. Within months of its launch in 2015, Jet was spending $20 million to $25 million a month on advertising, pouring funds into Google search optimization, blanketing buses and subway stops in New York and San Francisco with ads, and even running an expensive national TV campaign. Lore admitted years later that Jet was at one time spending around $40 million a month on marketing.
“We knew we had to get to scale and get to scale fast,” he said.
To help attract customers, Jet launched a referral program called Jet Insider that promised 100,000 stock options to the online shopper who courted the most fellow shoppers to sign up for beta access to the site. It worked. At launch, the startup was quickly overwhelmed, in part because of the way it was quietly sourcing inventory behind the scenes. Yes, Jet carried some of its own inventory in its own warehouses—mainly so-called consumable products like cereal, diapers, and shampoo. It also had a small handful of suppliers at launch who were listing products on the shopping site and shipping them to Jet customers themselves.
But about 70 percent of what the startup was selling at launch came directly from other shopping sites. The euphemism that Jet used for this hack was “Jet Concierge,” but the startup was simply listing a product on its site that it had no connection to, selling it to a customer, and then ordering the product from a rival to have it shipped directly to Jet customers.
Jet executives thought it was one of the only ways to solve their “cold start” problem until they could attract more selling partners. But in the short term, it made absolutely no financial sense. And it required extra staffing: Jet had a five-hundred-person team of contractors located in the Philippines to help execute these orders from rival sites. But they quickly became overwhelmed when the customer demand far exceeded expectations at launch.
“It was utter chaos,” a former executive told me.
If Jet didn’t want to disappoint customers, it needed a solution. The company went into triage mode, recruiting and training employees from teams across the company on the right way to place orders from these competitor sites. One former executive told me that about $700,000 of Jet’s $1 million in first-day sales came courtesy of this program. And of that $700,000, around $250,000 alone was ordered from a single rival: Walmart.
For the first month following launch, it was all hands on deck. Most teams at Jet were asked to put aside their day jobs and help place orders. The company also bused corporate employees down from the Hoboken, New Jersey, headquarters to the startup’s first East Coast warehouse, located in the south New Jersey town of Swedesboro, which did not have enough room or workers to keep up with demand.
“We needed to ship more and couldn’t,” recalled Joe Gullo, the manager who was hired before launch to run the New Jersey facility. “We were storing items outside during the day. People were working eighteen hours a day. It was, in the truest sense, the startup warehouse nightmare.
“But I was thrilled,” he added. “Because up to that point it was unclear if any of it was going to work. Admittedly, though, we were selling people one dollar for eighty cents.”
That first summer of 2015, Lore spent a lot of his time doing what he does best: pitching his long-term vision to investors. The pitch went something like this: E-commerce sales in the US only represented around 10 percent of total retail sales, and that percentage was only headed in one direction: up. While Amazon was the clear leader in the space, there was no clear-cut No. 2. Not Walmart, not Target, and not Costco, all of which had long neglected the idea of building a large internet presence. Jet could be that No. 2, and along the way, build a business worth tens of billions of dollars—or more. How would Jet do it? By appealing to shoppers who would rather save money than get every product under the sun from Amazon Prime within a day or two of their order.
Jet’s strategy and tactics for creating customer discounts were unique and predicated on the idea that the startup would eventually have enough inventory in enough supplier warehouses that when customers placed large orders, they could be fulfilled out of a single warehouse, bringing packing and shipping costs down. All the startup really needed, Lore stressed repeatedly, was enough advertising money to attract enough customers, which would in turn attract the brands and retailers needed behind the scenes to fulfill the startup’s inventory needs and, thus, its discounting strategy.
“It’s just math,” he would often say. Amazon and Jeff Bezos were famous in business circles for the idea of the flywheel, and Lore believed Jet could create its own, substituting express shipping speeds in exchange for the lowest prices on the web.
With impressive sales numbers after Jet’s July launch, Lore received interest from private equity investors with a similar message to the founder: we need you to get bigger, fast.
Lore knew Jet would have to raise hundreds of millions, if not billions more anyway to reach its full potential, so he wanted to take advantage of this opportunity. But that would mean a drastic shift in how quickly the startup’s sales would need to grow. Jet execs had been projecting that the startup would hit an annualized run rate of $1 billion in gross sales eighteen months after launch. But because of this investor interest, plus early momentum among customers, Lore slashed that timeline to ten months. Bezos would have been proud.
Around the same time, the startup’s investors and executive team began considering a decision that would have seemed foolish just a few months earlier: axing the $50 annual membership fee for Jet customers, which was intended to be the startup’s main source of profits as well as a substantial (and steady) revenue stream.
There were a few factors feeding the debate. At the time, Jet was planning to offer customers two buckets of discounts that would total 10 to 15 percent on an average multi-item order. The first bucket offered up-front discounts of around 7 percent on most individual products, which was in essence the reward for the membership fee and a way to lure new shoppers in. But the core of how Jet hoped to set itself apart was its “Smart Cart” savings—discounts of 4 to 5 percent, on the low end, that shoppers earned when they added more products to orders, resulting in more efficient orders for Jet seller partners to fulfill.
In early site tests, Jet executives noticed that when the startup didn’t discount individual items off the bat, but just offered customers the Smart Cart savings of, say, 4 to 6 percent, they still completed a purchase at a similar rate as customers who had received both buckets of discounts, totaling 10 to 15 percent. Therefore, they didn’t need the original savings of 7 percent that the annual membership was providing for them. There were other factors, too. Many of the retailers and brands that Jet recruited to sell through its new marketplace were intrigued by an alternative to selling on Amazon, but didn’t love the perception that Jet was a discount site. Perhaps more importantly, they did not appreciate Jet pricing their merchandise below their desired up-front retail price.
Landsman, the marketing and customer experience chief, had her doubts about the membership shift. Nearly one million people had signed up for Jet’s prelaunch waiting list and had just been converted to members on a free trial basis. How would they react to a key change in the Jet value proposition so early on? And could the startup execute the membership about-face before all of those early customers began being charged for the service? Having to issue a rebate to hundreds of thousands of shoppers could be both operationally and optically distracting.
Lore had heard the arguments for and against the membership fee for months and had initially stuck to his gut that the model could work. But as the CEO discussed the topic more with the investors who sat on Jet’s board of directors, there was concern that a subscription would cap the company’s sales growth and potential valuation. These financial backers were already committed to pumping hundreds of millions, if not billions, into the startup, and so they needed the company to be a colossal home run. Training customers to learn a new way to shop would be hard enough. Add an up-front subscription fee to the equation and that uphill battle looked even steeper.
“You have to sink a serious amount of marketing money in if you’re going to steal customers away from someone else,” a former Jet.com executive said. “And if you have a membership model, it gets even worse.”
Lore knew what it would take to land those private equity investors he’d flirted with over the summer, and it was clear it would be easier to hit the $1 billion sales goal quicker without the membership fee. After listening to all sides, Lore made the call: the membership fee would be sacrificed before it ever saw the light of day.
Still, the decision put Lore and Jet in a precarious position. Without the membership fee, the company was losing its main source of profits. Now the company would have to grow to a massive scale since big online retailers often sell low-priced consumable goods for tiny profits per order. But that’s easier said than done: Jet had to convince shoppers who might already be satisfied shopping on Amazon.com or Walmart.com or Target.com to visit Jet.com in the first place. Once they did, they had to hope that Jet’s unique discounting structure would be both easy enough to understand and attractive enough to keep customers coming back again and again. Some inside Jet wondered all the while whether Amazon was paying special attention to the young startup.
Turbulence
Less than a week before Jet.com launched in July 2015, Jeff Bezos’s company held its first Prime Day—a twenty-four-hour discount extravaganza for its tens of millions of Prime members. Amazon portrayed the event as a celebration of its twentieth anniversary, but some Jet executives wondered if the timing had anything to do with their impending launch. (Former Amazon executives deny it did and, on this, I take them at their word.) Then, shortly after launch, Jet employees watched as Amazon’s pricing technology followed Jet prices both up and down. It was not uncommon at the time for Amazon’s technology to match major competitors on prices, but a startup that had just hit the scene? That was different. That felt personal.
“That would make sense when we were at a billion [gross merchandise volume], but they did it right out of the gate when we were at $2 GMV,” Landsman said. “That did not feel totally programmatic, because there’s no point to price-match someone who’s not big enough in the market to matter yet.”
But inside Amazon, executives noticed the attention Lore was garnering for Jet, even while the shopping site was still in beta.
“Marc was really good for both Quidsi and Jet at getting visibility to what he was doing,” said Greg Greeley, the nineteen-year veteran of Amazon and the vice president who oversaw the Amazon Prime program when Jet launched. “Marc had been with us long enough to know we took that pricing very seriously. On the other [hand], maybe he was testing us—how much damage can he inflict and if that was going to help him get more attention.”
Indeed, in Jet’s first few months of beta testing before its public launch, product pages on Jet featured Amazon’s price for the same item to prove that Jet had the lowest price on the web.
“Anyone who is doing that is inviting customers to compare,” Greeley continued. “And so by definition, Amazon has no choice but to take that very seriously.”
Jet was also trying to overcome another outside force, but this one wasn’t a competitor. It was press coverage from the Wall Street Journal in 2015 that raised questions about various Jet.com business practices, including a program in which Jet rewarded customers with merchandise credit if they clicked through from Jet.com to buy items on other retail sites. While Lore’s ambition, stated goals, and history with Amazon made for a good media narrative, his strong storytelling skills had one flaw.
“You know what Marc is like when he’s telling a story—he’s all about the narrative arcs and the big picture,” a former Jet.com executive said. “But the rounding errors of, ‘Is he getting the decimal points and data points exactly right?’ He doesn’t give a shit about that.”
Those traits can give credence to Lore’s supporters and critics alike. For his biggest fans, Lore is the visionary and eternal motivator who gets the absolute most out of his employees because he not only paints a picture of an extraordinary future that, together, they can make possible, but has a strong mathematical mind that makes it all seem possible.
“Unlike a lot of pie-in-the-sky founders, he’s connected to the numbers,” one venture capitalist told me.
And Lore makes people want to believe.
“My grandmother had a saying, roughly translated from Yiddish: ‘People who could talk clouds out of the sky,’” Landsman said. “And I always thought this about Marc.”
But many in the venture capital industry were skeptical of Lore. One of the reasons, even if investors wouldn’t admit it publicly: his background and pedigree did not match those of Silicon Valley legends. Lore never launched a startup in San Francisco, didn’t know how to code, nor did he attend Stanford or the Massachusetts Institute of Technology, or drop out of college for that matter. After graduating from college, Bucknell University in Pennsylvania—the first in his family to do so—Lore spent the first few years of his professional life on Wall Street, working in risk management and eventually running himself into the ground in the pursuit of riches.
“My family was full of mercenaries,” he said years later. “I didn’t know anything else.”
His dream was to make six figures by age twenty-six, seven figures by thirty-six, and eight figures by forty-six. He didn’t have grand Silicon Valley visions of changing the world—he just wanted enough of a fortune to buy the world. (He achieved the first milestone but, a year later, collapsed at work of exhaustion and figured there had to be a better way. He finally listened to his entrepreneurial intuition and never looked back.)
His parents were twenty-one and twenty, respectively, when they had him, raising him and his two younger siblings first on Staten Island, the least-loved New York City borough, with a large Italian American population, and then New Jersey from middle school on. Lore was broad-shouldered and burly in his Diapers.com years and his look was more distressed denim jeans and shoes than khakis, hoodies, or sneakers. His accent also carried hints of his Staten Island and New Jersey upbringing. The Wall Street Journal highlighted this in one of its pieces on Jet.com, which some Jet executives read as a personal dig. The reporter wrote that Lore’s “Staten Island, N.Y., roots come through whenever he says ‘toilet paper.’ (It sounds like ‘TAW-let paper.’)”
The Journal’s coverage of Jet.com was more damaging than that. One of the first pieces focused on the concierge service Jet quietly employed at launch that allowed shoppers to buy products from other retailers while on Jet.com, even when the retailer was not partnering with Jet or even aware that its products were advertised on the marketplace. The article was published two days before Jet’s public launch and shined a light on what seemed to be a completely unsustainable model. A few weeks later, the newspaper published another piece, about retailers who were outraged when they learned that Jet was listing them on its shopping site under a so-called affiliate program called Jet Anywhere. The program implied that these retailers and brands were partners of Jet even when they weren’t. In fact, Jet simply signed up as an affiliate partner through a third-party company that worked with all types of e-commerce sites.
“That’s a no-no,” a former e-commerce chief of a large US apparel brand said. “You want to be a partner? Then come to me directly.”
Landsman, Jet’s former marketing chief, characterized the impact of the Journal’s reporting as “catastrophic.” Retailers and brands that were once likely to sell on Jet fled for the emergency exits.
“Home Depot knew it was going on, but as soon as that [story] hit, it was, ‘We have to stop this,’” according to another former executive referencing the story about Jet’s early concierge service. “And that happened over and over again.”
Until that point, Home Depot had led some Jet.com executives to believe that they were on board with selling goods through the site. Losing them was a big blow. The company also had serious conversations with Best Buy about funneling some of their listings through Jet.com.
“That was going to be our big electronics source,” the former executive said.
But after Lore traveled to meet with Best Buy’s then-CEO to try to close the deal, the electronics giant decided against the partnership. Bed Bath & Beyond also balked once the press attention reached a fever pitch. Then there was REI, the outdoor-gear retailer. When its leadership team caught wind of Jet including their logo on its Jet Anywhere page, a top executive insisted on a phone call with Jet. But if a conversation requires two people to talk, this would not be a conversation.
The REI executive “was just nasty, saying, ‘I don’t know you! Your strategy is all wrong and I’d never ever stoop to your level to work with you!’” the former Jet executive remembered.
REI blasted a message out to a wide range of outdoor brands warning them against working with the nascent startup. Legal warnings rolled in from apparel and fashion brands, too. Jet employees tried to make the most of the opportunity.
“For every one of the letters we got from a brand’s legal team, we would reach out to them and tell them we would love to talk,” one former Jet employee said. “From that, we’d try to convert them by explaining to them how we work. They became sales leads conversations and we turned a few of these.”
When the fiftieth cease-and-desist letter arrived, Jet’s general counsel rewarded the employee assigned to respond to it with a celebratory beer.
But the challenges of getting big-name brands and retailers on the marketplace extended beyond the reaction to negative press. Jet executives knew that if they were going to build the Costco for the digital age and beat out Walmart and Target as the No. 2 US e-commerce destination, Jet needed to have the best prices on things people buy repeatedly: consumer goods like toothpaste, toilet paper, and tampons. The startup was okay with losing money on these sales to beat competitors on price, in a move that even Jeff Bezos would have to respect. It also stocked them in its own warehouses so it could guarantee two-day delivery speeds that would be competitive with Amazon Prime. But those bargain-basement prices on consumable goods meant the company needed to make strong profits in other product categories, such as home décor, sporting goods, and apparel.
While some apparel brands did appreciate the appeal of an online marketplace not named Amazon, the idea of having premium apparel sit alongside grocery items or toilet paper on the Jet website was not appealing to many clothing execs. Jet employees pitched brands on having more price control than they would have on Amazon and other marketplaces, as well as visual merchandising capabilities that would better represent their brand than the tech giant could or would. They also tried selling them on the company’s unique discounting structure, which in hindsight was probably a mistake when pitching premium apparel or fashion brands that associate discounts with diluting their image.
The team did have some successes though. Getting Cole Haan on board was a coup, even if it took a ton of manual backend work by Jet employees just to get them up and selling on the site. Signing up Yoox, an Italian online retailer of discounted luxury fashion, was also a big win.
Ultimately, though, Jet struggled to get enough attractive apparel and fashion brands on board, and former employees blame that in part on who the core Jet customer was. It also didn’t help that other than the two-day-delivery promise on consumables that Jet stored in its own warehouses, deliveries from fashion brands or apparel retailers could take a week or longer to arrive at customer doors when being shipped from their own facilities. Despite what Lore preached publicly about how many online shoppers were willing to wait a while in exchange for discounts, it did not always seem to be true for those purchasing apparel.
Project Cheetah
In the fall of 2015, as Jet’s first holiday season approached, the company’s future was already being called into question. Executives who commuted from New York City to Jet’s modern Hoboken headquarters—a high-rise on the opposite bank of the Hudson River—joked with each other that they should only be buying weekly, instead of monthly, transit passes, seeing as they might not have a job a few weeks later.
As Jet pumped even more money into advertising to boost sales in the early fall, Lore returned to his conversations with the private equity firms he had flirted with during the summer. He was in for an unpleasant surprise. One firm that had verbally agreed to invest $30 million in Jet was now pulling out. Without that investor, the whole funding round was in danger of crumbling. Lore needed to do one of the things he did best, and quickly: he needed to convince other investors to trust him with more money.
That fall, Lore hit the road armed with “simple math,” as he put it, and a promise to make it come true: if Jet could just raise enough money over the following years, it could invest more in marketing and reach $20 billion in gross sales by 2020, allowing it to start turning a profit. At one point during this stretch, Lore pulled back-to-back all-nighters, and, on a cross-country flight, his body fought back. The multimillionaire entrepreneur vomited all over his seat.4 On another occasion, Jet executives arrived at the Hoboken headquarters one morning to find a stubble-faced man stretched horizontally across a bench in a conference room. It was Lore, “fresh” off a red-eye.
But in late 2015, facing down a month or so of cash in the bank, Lore finally succeeded and secured hundreds of millions of dollars in new investments led by Fidelity, the mutual fund giant.
“You’ve probably never had the opportunity to see Marc pitch when he’s fund-raising, but he’s like the equivalent in fund-raising of the Beatles,” Landsman said. “I’ve seen very staid, conservative VCs who, when Marc pitches, turn into gushing schoolgirls.”
But the investments couldn’t fix Jet’s main problems: the company was losing money. Tons of it. And the shopping site didn’t have enough repeat customers who were sticking around. For those employees in the know, it was depressing. Lore had been intentional about building a flat and transparent culture at Jet to motivate employees in a way that was the opposite of the “carrot and stick” approach the CEO says he experienced at Amazon after the Quidsi acquisition. Jet did not include standard noncompete clauses in employee contracts, freeing workers to pick up and go work for a competitor if the startup did not live up to its end of the employer-employee bargain. Every Jet employee was paid the same amount for a given position, and all Jet employees had access to an app that divulged the company’s top-line financials.
“They did something that no other company had done at the time: complete salary transparency,” said a former employee, Marcie Cheung. “I came in as an associate director and I knew that all ADs were paid the same salary; this idea blew my mind and had a huge impact on me.”
Despite the transparency and collaborative spirit, by the summer of 2016, some employees who had been with Jet since the earliest days inside its original Montclair, New Jersey, office were growing disillusioned. When Lore gathered the growing company for his regular pep talks, new employees were mesmerized. But some long-haulers rolled their eyes.
“There was a sense of futility,” one early employee said years later. “You couldn’t stop because if you stopped, everything would fall apart. We ran fast and loose and it was like barreling down a hill at full speed and you couldn’t trip. But the music had stopped. In short, the theory wasn’t proving out.”
The theory, essentially, started with the idea that Jet would attract a big enough collection of brands and retailers to sell on the site that it could use their warehouses to help blanket the country. These selling partners would also set rules on the backend to help Jet’s pricing system decide whether to award a certain merchandise sale to them or another merchant, based on factors like the location of the customer placing the order in relation to their warehouse. (In reality, few brands or retailers even had the personnel to handle such a role.) The goal was that Jet would have enough inventory coverage nationwide that when a customer placed a multi-item order, the startup’s technology could route it through a single warehouse or a couple of facilities that were located near each other or near the shopper. This would reduce shipping costs, and Jet would reward the customer with discounts.
“I will say I believed in that promise long after I actually should have because the beauty of the simplicity of that idea, and the idea of reengineering the supply chain was really compelling,” Landsman, the chief customer officer, said.
The startup did indeed provide discounts as customers added items to their cart. But all too often, the price had little to do with real supply chain savings and was not even correlated with the price at which a brand had agreed to sell an item.
“Practically, the way it worked was we would just take massive losses,” a former employee said. “We would have rules that were preset that dictated how the consumer pricing would work. And, on the backend, we’d give it to the best bid we could but it wasn’t based on what the retailer was offering. There were many cases where the retailer would come to [the chief revenue officer’s] team, and it was, ‘I’m the head of e-commerce and my CEO went on your site and ordered something and you guys paid us more than what the customer paid for it.’”
Yet Lore still believed he could build Jet into a stand-alone business. Call it the entrepreneurial distortion field, or call it conviction. Either way, Lore continued to spend considerable time out of the office and on the road, selling his vision to potential partners and investors.
He also looked for ways to bulk up Jet’s sales quickly. In March 2016, Jet purchased an e-commerce site called Hayneedle, which was known for selling outdoor and indoor furniture. The site had been around for fourteen years and was doing more than $300 million in annual gross sales, but growth was stagnating and the site was losing money. Jet paid just $90 million for the company, which instantaneously doubled Jet’s total gross sales numbers overnight. Even better, while Hayneedle’s overall business was unprofitable, almost every product it sold was contribution profit-positive, meaning there was money left over after subtracting variable costs—such as the wholesale cost of an item and the packaging required to ship it—from the sale price. At Jet, on the other hand, executives were starting to feel some heat for selling so many items at a loss.
In the spring of 2016, one of Jet’s longtime investors and board members made an introduction to a potential savior: Doug McMillon, Walmart’s CEO. McMillon had taken over as chief executive in 2014, several years after Lore had spurned the retail giant’s offer to buy Quidsi, so they didn’t know each other. The two sat down for a meeting inside the Quail Room, the conference room at Walmart’s home office adorned with Sam Walton’s quail-hunting photos. At first the discussion focused on a possible investment; Lore was adamant that if Jet was able to keep raising new funds, and pump them into giant ad campaigns, enough customers would end up sticking with Jet and its discounts that the math would eventually work itself out.
That June, leaders at Jet’s New Jersey warehouse were instructed to prepare the facility for a special visit, with no hint as to who would be walking in the door. On the day of the tour, Lore arrived at the warehouse accompanied by a group of Walmart executives. As Jet leaders led the group through the massive facility, showing off the startup’s processes and efficiency, one of the Walmart leaders broke off from the pack. Jet employees, communicating across the warehouse on walkie-talkies, eventually tracked him down in an unexpected spot.
“We shipped a lot of adult products like [sex] toys and had them sequestered in a cage, because they were also high-theft,” Gullo, the warehouse leader, said. “And Walmart did not sell that type of stuff. We found him in there just looking around.”
This one difference between Walmart and Jet would be a precursor of more dramatic cultural differences that would eventually emerge. Still, Lore and McMillon clicked right away, but the Walmart leadership team didn’t want a potential deal to be a normal venture capital-like cash-for-equity arrangement. The brick-and-mortar titan offered to secure lower shipping rates for Jet from FedEx, since the retailer did so much business with the giant shipping carrier. Walmart later offered to also help Jet get lower wholesale costs on inventory purchased from Unilever, the massive consumer packaged goods company. This kind of inducement happened several times, until McMillon floated a more straightforward deal: buying Jet outright.
At Walmart, McMillon knew his company had to do something drastic, and fast. So did Greg Penner, the former venture capitalist who had married into the Walton family and encouraged company leaders to embrace e-commerce in the early days. Penner had risen to the Walmart chairman role in 2015, taking over for his father-in-law, Rob Walton. Without Penner’s endorsement, the pursuit of Jet probably wouldn’t have gone anywhere. While a CEO like Bezos might be able to push through a deal that his board members weren’t fond of because of his founder clout or the fact that he also held the chairman role, the dynamic was much different at Walmart.
“We’ve had a great tradition of our chairmen working closely with the CEO,” Penner has said.5 “So my office in Arkansas is right next to [McMillon’s], and he and I talk every day. I tend to play a more active role, probably, than most chairmen.”
The uphill battle facing Walmart was plain to see for both leaders, as well as for Lori Flees, Walmart’s head of corporate development. When Flees arrived at Walmart, the retailer’s online business accounted for less than 3 percent of total e-commerce sales in the US, compared to Amazon’s 33 percent. Moreover, its trajectory was pointing in the wrong direction, with revenue growth decelerating quarter after quarter, while consumer spending online was heading in the other direction. Plus, Walmart was actually losing market share in the US in online and store sales combined—something that Flees found many company leaders weren’t aware of, because they were used to operating in their own silos. Flees, a no-nonsense longtime strategy consultant who went to Harvard for her MBA and played on the club ice hockey team there, believed that something drastic needed to be done. Inside Walmart, the plan to acquire Jet was first referred to by the code name Project Cheetah.
“The whole thesis was it would make us faster,” Flees, who oversaw mergers and acquisitions, told me. “My response was always, ‘If we don’t do this, what are we going to do to go faster?’”
In Lore, you could imagine McMillon squinting and seeing a version of a modern-day Sam Walton, an entrepreneur who wanted to find new ways to save money for customers every single day. McMillon also knew the credibility that Lore had developed within the e-commerce community. With him at Walmart, a halo effect could attract fresh technical talent, filling the retail giant’s e-commerce division with new life and energy. It would also serve as a declaration to Wall Street investors that the brick-and-mortar giant was finally taking its digital future seriously.
Also, by then it was unclear whether Walmart’s current global e-commerce chief, Neil Ashe, was ever going to be the leader to make a dent in Amazon’s widening lead in online sales. Ashe was hired in 2012, two years before McMillon became Walmart CEO, and had been a longtime executive in digital media, not e-commerce or retail, when he got the job. The head of the most important future sales channel for the world’s largest retailer hadn’t led a large e-commerce operation before.
On the other hand, Lore had spent the last fifteen years living and breathing e-commerce. What’s more, Lore almost joined Walmart when the giant retailer made the bid for Quidsi a few years earlier, before Amazon swept in to steal the deal. Lore also knew Amazon from the inside out. For Lore, the question this time around of whether to sell Jet.com to Walmart was easier to answer than it had been the first time, back in the Diapers.com days. Would he rather spend the next couple of years on a fund-raising treadmill for the small chance that Jet could become the next great independent titan of retail? Or should he tap into Walmart’s cash machine, leverage its huge store network to bolster online delivery, and make enough money along the way that his great-grandchildren’s great-grandchildren couldn’t create a financial worry for themselves even if they tried?
“It was like we were fighting this war but, all of a sudden, you get the allies’ planes and tanks to back you up,” Lore recounted years later.
Lore was interested, but he knew McMillon might need to sell his board of directors on the deal, in part because of how expensive it would be. So Lore went into salesman mode—but with a slightly different tack. He combed through every available annual report that Walmart had published since going public, and wove his learnings about Sam Walton’s innovative ways across a PowerPoint presentation that he voiced over to present his vision for what his company and Walmart could accomplish together.
“I knew at the time that I was a big part of the acquisition . . . but I wanted them to know that I [also] had a big vision for how Jet and Walmart could merge together and really make a formidable run at Amazon,” Lore said.
The pitch seemed to work, and Walmart board members supported the deal.
“I thought it was a great idea because it felt like we were flailing to some degree,” said Linda Wolf, the former CEO of the ad agency Leo Burnett who served on Walmart’s board for more than a decade. “And we really needed strong leadership.”
Unlike with the Quidsi acquisition talks year earlier, the negotiations with Walmart this time were fast and furious, though a media leak may have helped move things along. On the morning of Wednesday, August 3, 2016, negotiations were still ongoing when the Wall Street Journal reported that Walmart was in talks to purchase Jet.6 Landsman and other Jet executives were scheduled to spend that day slotting all of Jet’s employees into the right corporate compensation categories at Walmart. The setting was the executive’s Manhattan loft apartment so no leaders would be late to a small party Landsman was hosting on her roof deck that evening for the startup’s summer interns. While the execs scrambled to complete the task, Lore locked himself in one of the only private empty spaces in Landsman’s loft: the bedroom of Landsman’s then fifteen-year-old daughter. There, Lore cemented the final details of the acquisition over the phone with Walmart’s CEO.
Though the negotiations moved quickly, there were complications. One of Walmart’s stipulations was that Jet stop selling top consumable products—items like toothpaste and packaged snacks—below the price of the same items on Walmart.com and, most importantly, those in Walmart stores. As a result, Jet leaders had to craft countless different permutations of future business projections for Jet.com based on different pricing and marketing adjustments.
On Sunday night, August 7, I broke the news that Walmart would announce its $3 billion acquisition of Jet.com the following morning.7 Lore would be named the CEO of Walmart’s US e-commerce business. The next morning, Walmart made it official. The world’s largest retailer was staging the largest e-commerce acquisition ever, paying $3.3 billion for a cash-burning, wobbly operation that was barely a year old.
No matter. When the deal was finalized that September, McMillon had gotten his man. And Lore was about to secure a war chest large enough to take another crack at Amazon—and Jeff Bezos.