Before Zappos: The inside story behind Tony Hsieh’s first millions

It was a weekday, and Tony Hsieh and Sanjay Madan were again lounging by the pool during a very long lunch break at their new condo in San Mateo, California. They had landed jobs right after college as software engineers at Oracle, the high-flying enterprise software behemoth at the heart of Silicon Valley. Led by the brash Bronx-born contrarian and playboy billionaire Larry Ellison, Oracle, which at the time was the world’s largest maker of data management software, was a keystone in Silicon Valley. Comparing their $40,000 salaries to what their other Harvard classmates would be earning, Tony and Sanjay learned they would be making a lot more money than the rest of them. “I felt that I’d succeeded,” Tony said.



Aside from the pizzazz of working at a flashy company, the job checked Tony’s only requirements: It paid well and required very little effort. Tony was assigned to test software for bugs and ensure that it worked after updates, a process known as regression testing. Each day it took him five minutes to set up a test and three hours to wait for it to finish. Then he would repeat the process two more times and his day would end.



But instead of waiting for the tests to end, Tony walked the few blocks back to his apartment, took a long lunch, napped, and then went to the pool with Sanjay if he was home. It did not take long for Tony to realize that his initial requirements did not equal fulfillment. He also became acutely aware of how the languor he was experiencing starkly contrasted with what was happening outside Oracle.



The year 1995, Fast Company declared, was “The Year Everything Changed.” Silicon Valley was brimming with innovation. The World Wide Web was still in its infancy, and those who understood its potential were finding multimillion-dollar ideas everywhere they looked. In January, a young Stanford graduate called Jerry Yang had registered the website domain Yahoo.com for a database he’d been building that sorted internet pages in a hierarchical order, making them easier to find, and thus launching the first popular search engine.



Two months later, as Tony was finishing his last semester at Harvard, a man named Craig Newmark started an email distribution list to his friends to highlight local events happening in the San Francisco Bay Area. This grew into Craigslist—a national online classified-advertising website that would one day strip newspapers and magazines of a vital revenue stream and change the media business model forever. Then in April, the online dating website Match.com launched, opening introductions for millions of people to meet virtually, shifting the millennia-old method of courtship online. And by July, as Tony was toiling away at Oracle, a young investment banker named Jeff Bezos launched a small online bookstore called Amazon.com out of his garage in Seattle.



Companies that were preparing society for the 21st century and that would one day change the world—the way we learn, meet, buy, sell—were popping up left and right, many within a few miles of where Tony lived. And because California prohibited—and continues to prohibit— companies from baking noncompete clauses into contracts, any employee could quit and immediately create a rival startup. And yet here were Tony and Sanjay—who graduated at the top of their class at Harvard—completely disengaged and bored, languishing around the pool. Making easy money at a big-name company, it turned out, didn’t align with Tony’s vision of being in control of his own destiny and creating his own rules.



To combat their ennui, Tony and Sanjay began toying with ideas for a side business. They landed on a website design project. Sanjay was a gifted graphic designer and programmer but was even more introverted than Tony, so he focused on designing and coding the sites. Tony, despite all his fears and insecurities when it came to talking to strangers, assumed the role of salesman.



To the surprise of both, their new venture, which they named Internet Market Solutions, seemed to take off. After the local chamber of commerce agreed to let them design its website for free, other small businesses signed up. A local mall paid them $2,000. Tony’s lunch breaks got longer. So did Sanjay’s nights, as he stayed up coding once his workday was done. After five months, the two had realized they weren’t going to build this company from their cubicles at Oracle, and something had to give.



Tony walked past his manager’s office three times before he mustered the courage to quit. “Wow! You must be joining another startup,” his manager said to him. “How exciting for you.” Tony thought of his two-man operation working from the living room.



Within a week, however, they learned a crucial lesson: Neither of them was actually interested in web design. Tony wondered whether quitting Oracle had been a good idea; his father, Richard, made it clear that he did not think Internet Marketing Solutions would ever be a success.



So, they went back to the drawing board and, on a weekend in March 1996, came up with the idea of LinkExchange. By building websites for local businesses, Tony and Sanjay learned that the only option for advertising online was to buy ads from tech behemoths like Yahoo or Netscape, which at a cost of as much as $10,000 a month was cost prohibitive. Just as Tony had crowdsourced study materials for his virtual Bible study group and then packaged the information into neat binders and sold it, LinkExchange enlisted small businesses to display banner ads for other companies on their websites for free.



With hundreds of small business websites, LinkExchange could then sell packages of banner ads across these sites to larger companies that would pay to advertise within the LinkExchange-enlisted websites. This was achieved with a credit system: Every time a visitor viewed a small business website and viewed the banner ad, the small business owner would earn half a credit that could be exchanged to display their own ad across the LinkExchange network. So, if a business had a thousand views on its website, it could display an ad 500 times across the network of other websites. LinkExchange would keep the other half of each credit to build out its own advertising inventory to sell to large clients.



LinkExchange rapidly developed traction, and Tony and Sanjay soon found that their workload had become overwhelming. So, they started calling up their friends.



Among their first hires were Tony’s childhood friends Alex Hsu, who had just finished at NYU, and Eric Liu, who had just graduated from UC Berkeley. Anytime a Harvard friend visited San Francisco, Tony would try to convince them to stay and work at LinkExchange. When Hadi Partovi, a Harvard friend Tony knew through the computer programming team, was offered a role, he declined because he was already working at Microsoft. But he offered up his twin brother, Ali, who he claimed was so similar to him that they sometimes switched places for job interviews. Ali was hired as the third partner for LinkExchange in August.



Tony and Sanjay needed money to pay their new employees, so Tony turned to the only investor who knew his track record—Alex Hsu’s mother. Despite losing $2,000 in his pizza business at Harvard, she was open to hearing another pitch from him. This time she agreed to provide a $200,000 seed investment.



Five months after they started in Tony and Sanjay’s living room, LinkExchange had grown into an office on Second Street, in San Francisco’s South of Market district, with fifteen employees. Looking around, Tony could see that with every new hire, he was recreating the magic of his Harvard dorm room. LinkExchange was becoming a hub for all his friends to be in one place. If everyone got along and had fun, he figured, they would work hard, play hard, and succeed. And like at Harvard, they often slept where they worked; employees recall Tony and Sanjay sleeping on a cot set up in the conference room.



Outsiders were starting to notice that the formula was paying off. “Any time of the day or night, somebody would pick up the phone,” said Ariel Poler, a Silicon Valley veteran who had founded an internet company and served on several boards for other tech startups. Ali had reached out to Ariel, and after a meeting the three partners—Tony, Sanjay, and Ali—they asked him to be a part of LinkExchange. “I remember being blown away by how active and energetic, how smart they were,” Ariel said. He soon became chairman of LinkExchange.







Other Silicon Valley moneymakers were taking notice, too. Shortly before Poler signed on as chairman, Tony and Sanjay received a call from a man named Lenny Barshack. A former Wall Street executive, Barshack had spent 10 years working for Salomon Brothers and New York billionaire Michael Bloomberg before deciding to leave finance for a chance to capitalize on the dot-com boom in the mid-1990s. He started an email directory company called Bigfoot, which eventually became a holding company for several internet companies. Barshack wanted a meeting, so they went to a steakhouse in San Francisco. The pair of 22-year-olds listened as Lenny, sipping a Kahlúa cocktail, made his offer: $1 million in cash to acquire LinkExchange and add it to Bigfoot’s portfolio. Tony, with his mop of hair, and Sanjay, with his dark bushy eyebrows, tried not to flinch. It was a life-changing amount of money. They told Lenny they needed a few days to think about it.



Within 24 hours, Tony and Sanjay replied with a counteroffer of $2 million, so they could each walk away with $1 million. “I have read somewhere that you’re in your best negotiating position if you don’t care what the outcome is and you’re not afraid to walk away,” Tony said. “I’ve made a lot of money in my lifetime,” Lenny responded, declining to meet their price. “But I’ve also lost a lot of money when I decided to bet the farm instead of taking money off the table. I wish you the best of luck.”



Four months after Barshack’s offer, Ariel introduced Tony, Sanjay, and Ali to Jerry Yang, the cofounder of Yahoo. Jerry’s company had become the embodiment of the dot-com boom, its logo emblazoned on the homepage of millions of internet surfers, pre-Google. Yang had just led Yahoo through an initial public offering in April 1996, at a whopping $1 billion valuation—an extraordinary size at the time. Yang also had more in common with Hsieh than most other Silicon Valley founders at the time: They were both Taiwanese and at the helm of tech companies in an industry where the majority of C-suite-level executives were white.



The three LinkExchange partners assumed Jerry wanted to broker an advertising deal between Yahoo and LinkExchange. But Yang didn’t want to negotiate a contract; he wanted to buy LinkExchange, for $20 million (the figure Tony cited in his memoir; according to Ali, it was actually $25 million). For the second time, Tony was doing everything he could not to flinch. The three founders informed their employees, still a tight-knit group of friends, of the offer, and for several nerve-racking days they considered their options. Tony understood that if they said yes to the deal, he would never have to work another day of his life. He then made a list of all the things he would buy with the money: a condo in San Francisco, a big-screen TV, a computer. Maybe some long weekends in Miami or Las Vegas. But ultimately, he realized, he would likely use the money to start another company because he loved the process of building and growing a venture. Why sell a company he was already excited about, only to start another company to be excited about?



In the end, he and the other founders turned down Yahoo’s offer. It was a seminal decision he would cite over and over again to underpin his assertion that chasing profits had never been his game, that it was always about passion and purpose. “There will never be another 1997,” Tony said during a company meeting, announcing that the Yahoo deal was not happening. His voice trembled as he looked around at the familiar faces of his homegrown company and realized he saw relief. This was not a moment of failure. It was time to continue building.



Yang, meanwhile, was dismayed by the failed acquisition and complained about it during a Yahoo board meeting, which caught the attention of one of his board members, Michael Moritz, a famed investor at the storied venture firm Sequoia Capital. Moritz, a British former journalist whose short-cropped hair and frameless glasses made him look more like a professor of capitalist theory than a venture capitalist, was known for being introspective and proper. Days after meeting the three founders at the LinkExchange office on Second Street, Sequoia invested $2.75 million in LinkExchange, bringing invaluable cachet and credibility to the company. Before this point, the only outside investor they had was Alex’s mother.



Shortly after, Tony approached Alfred Lin, his Harvard classmate, who after graduating had decided to get a PhD in statistics at Stanford University in nearby Palo Alto. Tony had wanted to work with Alfred on a business ever since they graduated and had pitched to Alfred everything from a joint Subway sandwich franchise to LinkExchange when he and Sanjay first thought of the idea in March 1996. But Alfred was cautious as well as obedient—he did not want to anger his parents and drop out of grad school to go into what seemed like a very nascent idea with Tony. He had been intrigued enough, however, to join LinkExchange part-time while he was enrolled in his PhD program. Now with backing from Moritz, he was entirely onboard and joined the company full-time as vice president of finance.







Over the next year and a half, the company spun into overdrive. They opened sales offices in New York and Chicago, and expanded to additional floors in their building on Second Street. The three founders ensured that they were accessible to the workers, eschewing corner offices and choosing instead to sit in the pit with the rest of the rank-and-file employees. All three had a computer science background, but they played slightly different roles. None was officially given the chief executive officer title. “We didn’t really have a CEO,” said Poler. “We just had the three guys splitting things. They were always a group to me.”



Ali took charge of business development strategy, while Sanjay, still painfully introverted, remained behind the scenes as head of product. Tony, described by early LinkExchangers as genuine and authentic in more intimate settings, was not necessarily a natural choice for a leader, and he was uncomfortable with public speaking. Kevin Ascher, an early employee, recalled seeing one of Tony’s speeches during a company meeting. “He was shuffling his feet. Not making eye contact and staring at the ground,” he said. “He had his hands in pockets the whole time.”



But while Tony lacked presence in the spotlight, he went out of his way to ensure that everyone felt included. “Tony instantly made me feel welcomed and comfortable,” said Susan Cooney, one of LinkExchange’s first female employees. “It was all those small interactions. They would all be walking out the door and it would be all guys and Tony would say to me, ‘Hey, Susan, come join us, we’re going to grab a bite to eat.’”



Tony’s words were few, which made anything he said seem more important. “Tony was the most visible founder,” said Skye Pillsbury, a public relations employee at LinkExchange. “People just had a respect for Tony. He was a kind person, he always seemed fair, and when he spoke you wanted to hear what he had to say.” Public speaking and building out the story around himself and the company was a skill that he wanted to improve, Skye recalled. “After we met with a journalist, he would always ask me, ‘How did I do? Was it a good meeting?’ He really wanted to parse it out afterwards, and he was very open to any advice and guidance that I had for him.” So, while there was no official CEO, to Sequoia and the rest of the board, “Tony was their darling,” Susan Cooney said.



This was particularly evident from his ability to humanize LinkExchange’s corporate entrants. Moritz, who had joined the board, was not necessarily an ideal culture fit—buttoned-up and 20 years older than the majority of employees—but he understood founders and also knew when to crack a smile. Shortly after Michael joined the board, the company asked him to come to the offices for the “initiation meeting,” a monthly event at LinkExchange where new employees would be tricked into wearing suits and ties for what they thought was a formal event, when in reality it was a practical joke—an idea of Tony’s.



During this meeting, Moritz and the new hires stood at the front of the room. Then, under Tony’s direction, someone broke out a boom box and started blasting Los Del Rio’s “Macarena.” Everyone in the room started clapping and cheering as Michael Moritz was forced to cross his arms and sway his hips in front of the entire company. Tony looked around at all the laughing faces in the room with feelings of contentment and happiness. I can’t believe this is real, Tony thought.



Outside of hazing new hires, LinkExchange started other traditions like happy hours at the local Irish dive bar, called Kate O’Brien’s. Another staple event was DrinkExchange, a monthly party hosted at different venues for tech employees from all over Silicon Valley, who were required to buy two drinks and give one away—a play on the credit system at LinkExchange. “Where Wuppies Gather: DrinkExchange Draws Hundreds Every Month,” read a 1997 headline from the San Francisco Chronicle. A play on “yuppie,” the word “wuppie” was reserved for flashy young professionals who made their fortunes on the web. “Last month, 400 revelers—mostly people in their 20s who work for Internet startups—congregated at Backflip in the Tenderloin,” the Chronicle article stated. “A line snaked out into the street and the wait at the bar was so long that people snuck in beers from the outside.”



Many of those who worked at LinkExchange during this time recalled a fast-paced and exciting culture. “It still goes down as my favorite work experience for my whole career,” said Kevin Ascher. “It was magical, and it was just fun. Everyone liked each other, and it was as much a social life as it was a work life.”



Tony started to drink more at LinkExchange. Having lived mostly a life of sobriety, he was now 23 years old and willing to embrace libations. Michael Bayle, one of the employees who organized DrinkExchange, remembered Tony being one of the biggest supporters of the event, even with his “Asian flush”—a reaction to alcohol that typically affects people of Asian descent (because of a missing enzyme that processes alcohol in the body) and which turns people’s faces red while speeding up their heart rate and inducing headaches and nausea. “He would turn super red within seconds of any beer,” Bayle said.



Skye Pillsbury also recalled Tony’s enthusiasm during one press tour trip, when he bought everyone tequila shots. “I actually remembered being really surprised because I didn’t picture him as a guy who would stay up until 1 a.m. drinking tequila shots,” she said. She recalled him being giggly and funny that night. “I remember feeling that he was more himself, like he came out of his shell after drinking.”







To those who saw and worked with Tony during this time, he seemed like a natural leader who was still learning but had all the potential to be great. To former Harvard classmates whom Tony had hired to help out at LinkExchange, he remained the mischievous and curious friend with wild ideas. In the summer of 1998, Tony organized an impromptu trip to Yosemite, and went to the camping store near the LinkExchange office to buy everyone tents.



In addition to Sanjay and Alex Hsu, other college friends including Jill Wheeler and Kami Hayashi joined them. Packed into Tony’s mother’s minivan, they left after work and arrived at Yosemite after dark, complicating the process of setting up the tents. No one remembered to bring flashlights, but of course Tony kept night-vision goggles in his mother’s minivan. Once they finished setting up one of the newly purchased tents, they realized yet another mistake: They would not be able to fit inside because Tony had bought ones meant for kids. The party ended up sleeping in the van.



Tony was also in charge of groceries for the trip, which to him meant a bag of potatoes, hot dogs, and beer. The plan was to cut open the beer cans and cook the potatoes inside. But cooking potatoes on a campfire took longer than expected, so they ended up eating cold hot dogs. Just as the group thought not much else could go wrong, the minivan’s brakes overheated on the drive home and stopped working as they wound through Yosemite Valley. Counting the mishaps and hijinks, the trip made for yet another typical adventure with Tony. It was the fairy tale that Tony had envisioned for himself and his friends all along.



But even fairy tales have an ending. Tony’s time at LinkExchange was soon marred by internal politics and drama that led to lessons learned. In 1997, as the dot-com era was in full swing, Ali had started discussions with Viaweb, a newer startup led by Paul Graham (who would later launch the storied startup accelerator Y Combinator), about merging their businesses. Just as the discussions were starting to finalize, Jerry Yang came knocking again. He offered $125 million for Yahoo to buy LinkExchange.



It was a lot of money, and enough to do away with any previous hesitations Tony, Ali, and Sanjay might have had. They said yes to Yahoo, signed a term sheet, and agreed to cut off talks with Viaweb. Days before signing the final agreement, Ali met Jerry Yang—the “undisputed king of internet at the time,” Ali later recalled—for drinks. In Ali’s excitement, he suggested to Yang that Yahoo should also think about acquiring Viaweb to make Yahoo’s search engine a powerhouse. “Our guys looked at them,” Yang responded. “We weren’t that impressed with their people.”



Ali, an excitable 25 year old, his confidence boosted by alcohol as well as the looming prospect of more wealth than he had ever imagined, challenged Yang. “Jerry, your guys are wrong,” he said. “The Viaweb team is amazing. Their engineers are probably better than yours.” Then Ali added, “They are hands down better than us.”



“Interesting,” Yang replied.



A few days later, after news of the Yahoo acquisition had already filtered through the LinkExchange halls, exciting employees of every rank, the founders received a devastating call. The $125 million deal was off. LinkExchange chairman Poler, who knew Jerry Yang personally, remembered that Yahoo had claimed there was “an issue with a pooling of interest or accounting problems,” he said. But in fact, with the help of Ali, Yang realized there was a better deal out there. A few weeks later, a new headline blared through the press and across the internet: Yahoo was buying Viaweb for $49 million.



LinkExchange soon realized that they needed a backup cash reserve, in case their revenue suddenly disappeared. An initial public offering, which could generate much-needed cash while paying out to investors like Sequoia that were seeking high-yield returns, seemed the most obvious resolution. That was until the Russian financial crisis hit in August 1998, creating a cascading effect on economies worldwide that suddenly erased the possibility of an IPO.



The other solution would be to seek an emergency round of funding or an acquisition. To prepare the company for a big exit, LinkExchange’s board decided to bring in a new chief executive officer named Mark Bozzini. At the time, it wasn’t unusual for a board to bring in a more seasoned CEO to a company in which the founders were very inexperienced business-wise. But according to several former LinkExchangers, hiring Mark—who was the chief executive at Pete’s Brewing Company before joining and did not have relevant experience in tech—was not a good move from the beginning. “Things did not go well with the CEO,” said Ariel Poler. “Not a happy thing. I don’t think it was a good cultural fit.”



“I would not describe him as someone who was beloved,” Skye said. It felt like “outsiders coming in to make us look ready for the next step. Tony didn’t sound like a talking-points founder. Mark was the opposite.” Meanwhile, according to one former LinkExchanger, there were employees who wanted to invest in the company ahead of the acquisition so they could make money by selling shares when the company was worth more. Tony and Sanjay were pushing for this plan, but other leaders shot the idea down. “Tony and Sanjay were doing their darndest to keep the culture together, and I believe they both struggled,” according to the employee.







Now in three cities with hundreds of employees, Tony started seeing unfamiliar faces in the office. “At the time, I didn’t think it was necessarily a bad thing. If anything, not recognizing people due to our hypergrowth made things even more exciting,” he later said. “But looking back, it should have been a huge warning sign for what was to come.” Tony never said whether there were specific employees who were hired or certain events that happened that led to his feelings of ill will toward the LinkExchange culture. Instead, he described it as a death by a thousand cuts. “Drop by drop, day by day, any single drop or bad hire was bearable and not that big a deal,” Tony said. “But in the aggregate, it was torture.” Somehow along the way, Tony felt he had lost control of the culture and direction of LinkExchange.



Toward the end of 1998, Tony became disengaged. One morning, he found himself pressing the snooze button on the alarm clock six times before coming to a harsh realization: The last time he’d pressed the snooze button that many times was when he was running software tests at Oracle. His detachment was felt throughout the company.



“When Mark came in, you just saw less of Tony,” Pillsbury recalled. Despite Tony’s personal withdrawal, the board was still searching for funding that could help it survive a potential economic crisis but realized that LinkExchange remained an attractive asset with solid financials. In the end, Microsoft came to LinkExchange with the highest offer. Hadi, the twin brother of Ali, who worked at Microsoft, sent a message to Microsoft’s chief executive at the time, Steve Ballmer, vouching for LinkExchange.



As part of the deal, Microsoft wanted all three founding partners—Tony, Sanjay, and Ali—to stay at LinkExchange for another 12 months. In most acquisitions, the board of directors has a say in such requests. But in this instance, in another vote of confidence, Michael Moritz turned to the three founders during a board meeting and said, “Look, guys, it’s your company. Whatever you want to do.”



After some deliberation, they decided to go through with the sale, which garnered mixed feelings. At the time, Microsoft was seen as “the evil empire” by many in Silicon Valley. The company was in the midst of major antitrust investigations launched by the U.S. government and was largely viewed as a bully to competitors. There was also a sense that Yahoo could have been a better fit as a parent company. “Yahoo was more our culture,” said Skye. “Being acquired by Microsoft felt like being acquired by corporate America. It wasn’t the acquisition or exit that a lot of us pictured.”



The exit negotiations left a deep impact on Tony. It was his first experience in true corporate America—the dog-eat-dog kind of dealmaking that was unforgiving toward empathetic leaders who cared more about changing the world and helping employees and small business owners than just a big, cash-positive heavy exit strategy. “Without getting into too much detail (and to protect the guilty), it was an education to me in human behavior and character,” he later wrote. “Large amounts of money have a strange way of getting people’s true colors to come out. I observed the greed of certain people who had joined the company right before the acquisition trying to negotiate side contracts for themselves at the risk and expense of everyone else in the company. There was a lot of drama as people started fighting and trying to maximize the financial outcome only for themselves.”



According to Steve Valenzuela, the chief financial officer of LinkExchange who was brought in right before the acquisition to work with Alfred Lin and prepare the company for an IPO, the negotiations started at noon on a Sunday in Redmond, Washington, at Microsoft’s headquarters. Microsoft first punted over a price tag of $120 million, which Valenzuela said was “totally unacceptable.” After six hours of back-and-forth in the board room, Valenzuela finally got Microsoft to $250 million. He then negotiated an additional $15 million to go toward key employees of the company for retention purposes—which Tony and Sanjay then took to the LinkExchange board for approval.



Tony also encouraged executives to give up some of their equity to give back to employees who did not have as much stock, including some lower-level employees. This was not well received by all the executives at LinkExchange. “It was pretty unusual at the time,” Valenzuela said, who gave up some of his own equity, per Tony’s suggestion.



As for the financial outcome for Tony, he would be set for life. If he agreed to stay for the full year after the acquisition, his take-home would be $40 million in Microsoft stock. If he didn’t, he would still take home roughly $32 million.



A few weeks later, in early November 1998, Tony and Sanjay found themselves at lunch together at a restaurant close to LinkExchange. As they were about to finish eating, Tony got a call. It was Alfred. He had just heard from Steve, who was closing the deal at Microsoft’s headquarters. “Well, I guess the deal closed,” Tony said to Sanjay. They stared at each other—Tony with the same mop of hair, Sanjay with the same thick brows. Except this time they weren’t staring at each other in shock, as they had after Lenny Barshack made his offer. It was in apathy and relief— relief that this was finally over. “I guess we should probably walk back to the office then,” Tony said to Sanjay. “Okay,” he replied.



Shortly after, Tony found himself making a list similar to the one he’d made when they got the first offer from Jerry Yang. This time, however, the list was not about all the things he would buy with his newfound wealth. It was a list of the happiest periods in his life. He realized that none of those moments involved money. All of them included building businesses and experiences. “Being creative and inventive made me happy,” he said. “Connecting with a friend and talking through the entire night until the sun rose made me happy. Trick-or-treating in middle school with a group of my closest friends made me happy.”



Tony left LinkExchange before a year passed. Though he left about $8 million behind, his stake was still worth $32 million—an eye-watering sum for a 25 year old. Shortly after, he took his friends from Harvard and a few others on a cruise. A bet is a bet, and Tony had become a millionaire within three years of graduating. But while surrounded by friends in the Bahamas as a newly minted millionaire, Tony felt a sense of melancholy. What’s next? What is happiness? What am I working toward? he wondered.



Such questions guide the lives of many, only now Tony had more money than most would ever see in a lifetime. “If you hate someone, give them a winning lottery ticket and announce it to the world,” his childhood friend Alex Hsu later said. “Having so much financial success in your 20s and early 30s comes with a different set of challenges that most people will never have to face.”







Excerpted from Wonder Boy: Tony Hsieh, Zappos, and the Myth of Happiness in Silicon Valley by Angel Au-Yeung and David Jeans. Published by Henry Holt and Company. Copyright © 2023 by Angel Au-Yeung and David Jeans. All rights reserved.