When the business icon died in a fire last week, questions abounded. The answers seem rooted in a Covid-period spiral, where he turned to drugs and shunned old friends.

^In August, shortly after Tony Hsieh, the legendary entrepreneur behind Zappos, moved to Park City, Utah, he eagerly awaited a visitor: the singer Jewel. The longtime friends originally met the way fellow rock stars should, on Richard Branson’s Necker Island, and Hsieh, who had been buying up properties around the mountain town, was planning to spend the next week showing her around.

Soon after arriving, Jewel played a private acoustic set for around 50 residents of the community Hsieh was building there—a reprise of sorts of the city-within-a-city of artists and entrepreneurs that Hsieh had famously created in downtown Las Vegas. It should have been a magical moment, according to a person who was there, with the Grammy nominee seated in front of a fireplace and views of the Wasatch Mountains framing the performance.

“He fostered so much human connection and happiness, yet there was this void. It was difficult for him to be alone.”

But within a day, Jewel abruptly left. Shortly after, the singer sent Hsieh a letter via FedEx, since he had forsworn email and texts as part of a digital cleanse.

“I am going to be blunt,” she wrote in the letter, the content of which was shared with Forbes. “I need to tell you that I don’t think you are well and in your right mind. I think you are taking too many drugs that cause you to disassociate.”

She continued: “The people you are surrounding yourself with are either ignorant or willing to be complicit in you killing yourself.”

Exactly one week ago, in the early morning hours of the day after Thanksgiving, Hsieh died from his exposure to a shocking house fire in Connecticut, where he had been staying. He was just 46.

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In the days since, the outpouring of grief has rivaled any for a business leader since the passing of Steve Jobs a decade ago. From Bill Clinton to Ivanka Trump to Jeff Bezos, thousands of people weighed in to share memories, photos and videos of a man who was widely loved, preserving the legacy of a tech entrepreneur who made an impact not just on his peers, but on his employees and even complete strangers, each reciting stories of exceptional generosity, humanity and vision.

Taken together, the memories of Hsieh paint an image of a man whose mission in life was to create happiness. This took shape in many ways. In pioneering, at Zappos, the concept of an online store fueled by a customer-first, no-questions-asked return policy, Hsieh arguably had a bigger effect on online retail than anyone short of Bezos himself. In investing $350 million into downtown Las Vegas, he lovingly turned a seedy part of town into an arts, cultural and tech hub, with a community of Airstream trailers, one of which Hsieh lived in for years. As a business evangelist, the 2010 title of his New York Times number one bestseller said it all: Delivering Happiness: A Path To Profits, Passion and Purpose.

But while he directly (by the tens of thousands) and indirectly (by the millions) delivered on making other people smile, Hsieh was privately coping with issues of mental health and addiction. Forbes has interviewed more than 20 of his close friends and colleagues over the past few days, each trying to come to grips with how this brightest of lights had met such a dark and sudden end.

Reconciling their accounts, one word rises up: tragedy. According to his friends and family, Hsieh’s personal struggles took a dramatic turn south over the past year, especially as the Covid-19 pandemic curtailed the nonstop action that Hsieh seemingly craved. According to numerous sources with direct knowledge, Hsieh, always a heavy drinker, veered into frequent drug use, notably nitrous oxide. Friends also cited mental health battles, as Hsieh often struggled with sleep and feelings of loneliness—traits that drove his fervor for purpose and passion in life. By August, it was announced that he had “retired” from the company he built, and which Amazon had let him run largely autonomously since paying $1.2 billion for Zappos in 2009. Friends and family members, understanding the emerging crisis, attempted interventions over the past few months to try to get him sober.

Courtesy of Fress Mossler

Instead, these old friends say, Hsieh retreated to Park City, where he surrounded himself with yes-men, paying dearly for the privilege. With a net worth that Forbes recently estimated, conservatively, at $700 million, Hsieh’s offer was simple: He would double the amount of their highest-ever salary. All they had to do was move to Park City with him and “be happy,” according to two sources with personal knowledge of Hsieh’s months in Utah. “In the end, the king had no clothes, and the sycophants wouldn’t say a fucking word,” said a close friend who tried to stage one of the interventions, with the help of Hsieh’s family. “People took that deal from somebody who was obviously sick,” encouraging his drug use, either tacitly or actively.

“He fostered so much human connection and happiness, yet there was this void,” the close friend continued. “It was difficult for him to be alone.”

Ultimately, that may have been a fatal trait. “When you look around and realize that every single person around you is on your payroll, then you are in trouble,” Jewel wrote in that August letter (a representative for Jewel declined to comment). “You are in trouble, Tony.”

^Growing up in San Francisco as the son of Taiwanese immigrants, the oldest of three boys, Hsieh picked up a combination of problem-solving (his father was a chemical engineer) and empathy (his mother was a social worker) that would become his hallmark.

At Harvard, he majored in computer science, but his big break came from securing the rights to sell pizzas to his dorm, since one of his best customers was Alfred Lin, who would become his best friend and close business partner. In 1996, soon after graduating, the pair launched LinkExchange, one of the very first major digital advertising networks, with Hsieh as CEO; two years later, at 24, he sold it to Microsoft for $265 million. “You never saw challenges, you only saw opportunities.” Lin wrote in a poignant “final letter to Tony Hsieh,” published by Forbes earlier this week.

AP Photo/Stephen Brashear

Hsieh had an addictive personality, and in his 20s, he was addicted to ideas. So he and Lin launched a venture capital fund to invest in them, turning an old car dealership into a startup incubator, complete with a hot tub and DJ-ready sound system. That’s when an even younger entrepreneur, Nick Swinmurn, left a voicemail on his phone, with the idea to start an online shoe retailer—a wild thought at the time to assume customers would buy something unseen that they needed to ensure fit properly and looked good on them.

ShoeSite, later renamed Zappos, came to define Hsieh’s career, as he ultimately invested and then took control of the company. Hsieh made clear from the beginning that it wasn’t just shoes they were selling. In 2005, Hsieh sent out a company email, requesting employees submit what the company’s purpose was. The result was a series of values that defined the company, including valuing employee inputs through their personalities over their position. The key trait they were looking for: passion. “Chase the vision,” Hsieh told Forbes in 2008. “The money and profits will come.”

“If the world could see how you are living, they would not see you as a tech visionary, they would see you as a drug addicted man who is a cliche.”

Such a company culture was almost unheard-of then, but it worked—people proved open to buying shoes on Zappos because the company made it so painless to return them, giving customers up to a year and accepting them with a smile. The company grew at a rapid clip, going from single-digit millions early in the decade to sales of $252 million in 2005. By then, the company had relocated from the Bay Area to Las Vegas.

Amazon, which was in the middle of moving from being an Internet bookstore to an “everything store,” was taking notice. It made an offer to acquire the company that year, and when those talks fell apart, Amazon launched its own online shoe retailer to compete. But in 2009, it made another approach, and Hsieh agreed to sell the company for $1.2 billion in stock, while remaining at the helm.

Jeff Bezos took a largely hands-off approach to Zappos, and instead saw teachings in Hsieh’s way of leading a company. “Jeff’s mindset was that if Zappos is doing something we can learn from, then it will have 25 times the impact in Amazon,” says Fred Mossler, a former Zappos executive who sat in on the meetings with Bezos.

And Hsieh, in turn, tried to amp up the stakes in terms of the impact he could have. He wrote his bestselling treatise. He experimented with a revolutionary—some would say anarchistic—version of a “holacracy” management philosophy, where no one at Zappos reported to anyone nor carried any titles. (It didn’t work: One out of seven employees took a buyout.) And he began his efforts to turn his Downtown Project in Las Vegas into his utopian canvas, drawing worldwide attention.

“He was never interested in shoes,” Mossler says. “Tony’s journey was to improve the human condition.”

^One thing was consistent with Hsieh across all those good years: Those who entered his orbit found their lives transformed. Cathy Brooks, a former journalist, once interviewed Hsieh for a podcast. Years later, she bumped into Hsieh at a conference and complained that she was feeling without purpose or direction. He invited her to come to Vegas and to bring her dog.

“He gave me the courage to jump,” Brooks says. Upon Hsieh’s urging, she drafted a business plan on the back of a napkin. “I’m standing right now in the business. . . . It was a parking lot, and now it’s a verdant, 9,000-square-foot off-leash play space for dogs.”

Courtesy of Fred Mossler

Similar stories abound in Vegas. He surrounded himself with people who were looking to innovate, build—and have fun. The parties were nearly constant, and Hsieh even had his own signature drink—shots of a herbaceous Italian spirit, Fernet—that he would imbibe anytime, with visiting clients, journalists or seemingly anyone.

But his brainchild also appeared to carry a dark side. Across the span of 18 months in 2013 and 2014, three founders of startups linked to the Downtown Project died by suicide. Some people suggested the deaths had been linked to the pressures of the initiative. Hsieh offered that the rate of the suicides was not higher than for Vegas in general. “Anyone else would be considered callous and sociopathic. . . . He was trying to understand it through the data,” says Paul Bradley Carr, a journalist who became close friends with Hsieh. “I think Tony saw happiness as a problem he was trying to solve, an algorithm he was trying to crack.”

“Each of us had to admit we hadn’t seen much of him lately. And even if we saw him at TED, he would skip the talks and host the late night. Whereas we would be in bed by 9:30.”

Toward the end of 2014 he stepped away from leading the Downtown Project and moved from his high-rise condo into an Airstream park, complete with an LED-lit stage and a roaming alpaca. Here, the revelry continued in a scene where recreational drugs were mixed with an evolving group of thinkers, creatives and entrepreneurs who sought Hsieh’s advice. He continued to helm Zappos, while cultivating an image as a guru who loved to party-hard, whether speaking appearances with Bill Clinton or adventures at Burning Man.

Over this period, many of Hsieh’s longtime peers found themselves on a divergent path from him. “Each of us had to admit we hadn’t seen much of him lately,” says one venture capitalist who knew him for more than a decade. “And even if we saw him at TED, he would skip the talks and host the late night. Whereas, we would be in bed by 9:30.” Nick Swinmurn, whose idea Hsieh transformed into Zappos, said that he had fallen out of touch with Hsieh and not spoken to him since last year. Their definitions of happiness had changed — a feeling echoed by several Hsieh friends, who said that they had married and started families, while Hsieh remained an extremely rich Peter Pan. “He told me that his friends kept getting younger and younger,” Swinmurn wrote in a Medium memorial post. “He seemed excited about this.”

^As the Covid-19 pandemic swept through the U.S., the quarantines hit Las Vegas particularly hard. Just before it hit, Hsieh had attended the Sundance Film Festival in Park City, Utah, and resolved to recreate an element of his Vegas utopia there.

Starting in March, Hsieh paid $18 million for nine properties in the mining-turned-ski town. He split time between Las Vegas and Park City across the spring, and then appears to have fully moved to the latter over the summer. During this transition, he began making his double-your-best-salary offer to new members of his circle if they relocated with him.

Numerous longtime friends tell Forbes that they suddenly found themselves unable to reach Hsieh. Carr says he and Hsieh had planned to take a road trip this year, but when he followed up several times across 2020, “I didn’t hear back from him.” Adds Carr, “That was concerning.”

Hsieh could point to his self-imposed digital detox as an excuse for his sudden reclusiveness, though that now seems a convenient excuse to avoid those who, like Jewel, might not approve of his latest reinvention. According to Justin Weniger, who cofounded the Life is Beautiful music festival with Hsieh and who stayed with Hsieh over the summer, Hsieh began focusing on biohacking — a practice that aims to change the body’s functionality — including cold baths and runs in the snow.

AP Photo/Brennan Linsley

A more dangerous hack: as Hsieh acted more erratically, he increased his use of “whippets” — inhaling nitrous oxide cartridges, like those in whipped cream canisters — a drug typically favored by bored suburban teenagers. “The reason I think he wanted to do nitrous is because it’s a dissociative,” says a close friend who was familiar with his drug use. “So you don’t have to deal with reality or deal with what’s going on.” During one hike in Park City, Hsieh walked barefoot while inhaling nitrous oxide the entire walk, according to a person who was with him.

Jewel, for one, expressed concern directly to him. “If the world could see how you are living, they would not see you as a tech visionary, they would see you as a drug addicted man who is a cliche. And that’s not how you should go down or be known,” she wrote in her letter to him. “Your body cannot take not sleeping. And the amount of N2O you are doing is not natural. You will not hack sleep and you will not outsmart nature.” She added that he risked crossing the line “from eccentric to madness.”

By August, he was out at Zappos after over 20 years at the helm. Amazon denies that they pushed him out, despite rumors. “It was Tony’s decision to retire as CEO of Zappos – it is not accurate that he was asked to leave his role,” said Jaci Anderson, a spokesperson for Amazon. Even if they did, though, it would be hard to blame them.

“In the end, he was so disconnected,” says a longtime senior Zappos employee who’s still with the company.

^At 3:34 am on November 18, first responders arrived at a New London, Conn. home, which Hsieh, generous to the end, reportedly purchased for a former Zappos colleague, Rachael Brown, with whom he maintained a very close relationship. (She could not immediately be reached for comment.) While several people escaped the main house, Hsieh had reportedly locked himself, either intentionally or by accident, in a storage area. He died nine days later, from what the coroner termed complications from smoke inhalation. The cause of the fire remains under investigation.

It doesn’t seem that Tony Hsieh, someone who inspired millions with his zest for life, had any intention of dying. The coroner has already declared his passing accidental. And in recent days, his family discovered that despite nearly more than half a billion in estimated assets, he hadn’t left behind a will. In some ways, count him as another Covid-19 victim, except that instead of succumbing to the disease itself, the virus appears to have accelerated some wrenching internal battles and a series of terrible external decisions.

“We are so deeply grateful for the outpouring of love and respect shown in the wake of Tony’s passing,” says his brother Richard, in a statement to Forbes. “There is no human that did not fall in love with Tony’s humanity, which is why so many have been left heartbroken.”

Jewel echoed those sentiments this week, serenading Hsieh in a tribute video that she posted on her social media accounts on Wednesday. “When all the world is a hopeless jumble and the raindrops tumble all around, heaven opens a magic lane.” And as she sang, tears ran down her eyes.

Additional reporting by Alex Konrad.