I heard the news about Tony Hsieh last night by text message. The latest in a years-long string of texts about Tony, sent by various mutual friends in Las Vegas.

Tony just bought the Ferguson Hotel.

Tony is turning Zappos into a Holacracy.

Tony is starting an airline.

Tony just turned Ferguson into a Airstream trailer park.

Tony is leaving the Ogden.

Tony just invested in the Las Vegas Knights.

Tony has a pet alpaca now.

Tony is moving into his trailer park.

Zappos is abandoning Holacracy.

I think Tony just bought a mountain.

Tony just quit Zappos!

Tony is apparently buying up half of Park City.

And then last night…

Tony Hsieh is dead.

I went straight to Twitter. Of course I did. And already my feed was packed with tributes to Tony. Everyone – everyone – had a Tony story to share. How he’d backed their company when no-one else would, how he’d helped them find a vegan restaurant during a trip to Vegas, or stayed up all night to give them a ride to the airport, or sent a delightful email about some missing shoes.

Even people who never met Tony had a Tony story – how his book had changed their life, or a chance encounter with the man had inspired them to build a better company. A wonderful reaction to a clumsy attempt to poach a Zappos executive..

I just heard about Tony Hsieh’s passing and it’s hitting me. Back in the early days of Simple I tried to poach his head of customer service. He found out and made a counter-offer: we could come to meet his team and they’d teach us about how they operated.— Josh Reich (@i2pi) November 28, 2020

My own Tony story is complicated. I first got to know him in 2011 when I wrote about Las Vegas for the Huffington Post. Like so many journalists before and since, I spent a night touring his then nascent Downtown Project as Tony gave me his standard pitch about how he was building the city of the future.

“So, how are you going to write sarcastically about all of this?” he asked me at the end of the tour. As I admitted to readers, I couldn’t find a way.

A few months later, during yet another trip to Vegas, I appeared on CNN to talk about why I had decided to quit TechCrunch. While I was still in the car back from the studio, my phone beeped with a message from Tony, inviting me to meet him at the Downtown Cocktail Room for drinks.

Over Fernet (him) and Diet Coke (me), Tony – who I’d met perhaps twice before – asked me what I wanted to do next.

“I have no idea,” I replied, honestly.

“I didn’t ask what you’re going to do,” said Tony with that smirk that always pressaged his springing of a trap. “I asked what you want to do.” He took a sip from his shot. “Like, if you could do anything in the world, professionally, what would it be?”

I shrugged and repeated a jokey idea I’d mentioned to a British writer friend earlier that week. “I’d start a wildly unprofitable print magazine. Something like Private Eye or Spy. Or maybe like the Economist with jokes. Burn a pile of money, and make a lot of rich people angry in the process.”  

I expected Tony to laugh. But instead he responded with a slow nod, like I’d just reached the final slide of a lengthy powerpoint. Then he drained his glass and waved towards the bartender for another. “Could you do that from Vegas?”

And so was born NSFWCORP, and so began my complicated relationship with a man who started out as my journalistic subject, then became my lead investor, then my friend, then the subject of some of the harshest and most relentless criticism I’ve ever written, then… Well. Like I say, it’s a complicated story.

I always warned Tony that if we took his money then NSFWCORP’s reporting on him – and the Downtown Project – would have to be much fiercer than our coverage of other tech moguls. Brutal even. He said he understood, and even agreed to my demand that he would never express an opinion – good or bad, public or private – about stories we published.

The first test of that promise came when we published a series of stories revealing that the Downtown Project had unwittingly hired a former cop turned pick-up artist as their head of security. We were fucking relentless, with headlines like “Skeeving Las Vegas,” “To Protect and Perv,” and “Copping a Feel.” Day after day, after day.

In hindsight, I was practically goading Tony to react. But he never once took the bait. In fact, he continued to introduce us to new investors, and send our reporters invitations to his events.

Unlike Tony’s other portfolio companies, though, the NSFWCORP team never went to the meet-ups, the parties or the music festivals. On the rare occasions we accidentally collided with a member of Tony’s ever-growing entourage, we snarked about it on our podcast. Then, after we sold the company to Pando, I continued to write relentlessly about the struggles of the Downtown Project: The exodus of entrepreneurs, the failed ventures, and most horrifying of all, a string of deaths by suicide amongst members of the DTP “community.”  

It was that last story that finally got a reaction from Tony, but not the one I expected. In response to my request for comment, he sent me a long list of suicide statistics of a number of major cities and towns, in particular those of comparable size to Vegas. Was it possible, he asked at the end of the list, that what I described as a ‘rash’ of tragic deaths was in fact statistically perfectly average?

It’s easy to imagine that question coming from the lips of Peter Thiel or Mark Zuckerberg or any number of other tech monsters. In those cases it’d be yet more proof of Silicon Valley’s sociopathic indifference to the human cost of ‘disruption.’

But anyone who has ever had a disagreement with Tony will immediately recognize his peculiar way of defusing conflict. His almost Socratic method of debate that could at times border on the callous. It was also, I came to realize later, his way of processing failure: You can’t solve a problem with emotion or anger, went his logic, only with data or process.  

Because for all of his faults – real and perceived – you can never accuse Tony of not caring about people. And, unlike most tech oligarchs, his generosity and kindness wasn’t limited to his friends and peers.

Even a short walk along Fremont street with Tony would become a three hour expedition as strangers interrupted to thank him for his kindness – for giving them a job when nobody would, for helping pay for a wedding, for a thoughtful birthday gift or a pair of plane tickets to celebrate a mother’s birthday.

A simple pause at a hot dog stand might devolve into a thirty minute interview as Tony peppered the poor vendor with questions about his business, about what toppings people liked most, about foot traffic, or the optimum size of a bun. Such moments might end with Tony pulling out his wallet and buying up the entire night’s dogs to take home to his guests at the Airstream park. Or, almost as likely, with Tony buying the chef his own restaurant.

Tony’s willingness to make spontaneous investments was legendary and borderline comedic. On Monday he’d invest in a bookshop, promising that Vegas would soon be the literary capital of the world. On Tuesday, after an investment in a 3d printing company, Vegas would be destined to become the globe’s micro manufacturing capital. On Wednesday it was baked potatoes for which the city would soon be legendary.

Perhaps it was that same constant search for the next obsession that made Tony seemingly unable to hold a grudge. Why no matter how many negative headlines or snark I would throw his way, he would only respond with more kindness and love. With another party invitation, or investor introduction.

My most vivid memory of his infuriating lack of malice was right after I published a long take-down of yet another zany business scheme: Tony’s plan to remove all management structure from Zappos and leave employees to fend largely for themselves. Or as I headlined it: A Holacracy of Dunces.  

Shortly after the piece went live, I saw Tony at a conference. My natural instinct was to run in the opposite direction, to spare us both from the awkwardness. But I was too late. A half second later Tony bounded over and pulled me into a deep hug.

Any journalist reading this knows what happens next – a faux friendly barrage of corrections, clarifications and protestations. Appeals to friendship. We’ve all experienced it from the Shervin Pishevars of the world: The grotesque belief that one can simply bro a critic into submission.

But not Tony. Instead Tony asked quietly whether I had time to go for a walk. He didn’t want to talk about my story, he said. He had, after all, promised never to do that. If I wanted to share more about why I thought Holacracy was so damaging he’d be glad to listen, or introduce me to people inside Zappos who could talk about their own experiences. But otherwise, he understood that I had a job to do.

But, he explained, there was a line in the Holacracy piece that had upset him deeply – a line that still haunts me as I write this.

In it, while giving context to my involvement with the Downtown Project, I described the ‘Skeeving Las Vegas’ scandal as “the story that ended my friendship with Tony Hsieh.”

Of course that wasn’t true. Or at least it wasn’t fair. Friendships are complicated, and mine with Tony had always been tumultuous.

As we walked around the hotel grounds, Tony switched to Socratic mode – gently interrogating me on the meaning of friendship and how it is nurtured and maintained. Hadn’t the deal we’d made – for him never to comment on my stories – been as much about maintaining our friendship as about keeping an investor at arms length? So how could I say that the story had ended our friendship when the terms of our friendship had rendered him unable to respond? He seemed genuinely confused, and hurt.

This time it was me who couldn’t respond.

The true test of friendship in the tech industry, I think, is if someone still acts like a friend when they don’t need anything from you. When, in fact, there’s nothing you can give them.

By that metric, Tony Hsieh was a true friend. Not just to me, but to countless others to whom he gave his time, energy, hospitality, support and – yeah – sometimes money without ever expecting a return.

In 2017 I wrote a blog post about how I was quitting journalism, and Silicon Valley. Not long afterwards, Tony texted me and invited me to come to Vegas and see the new village of tiny houses he’d built at the Ferguson. There over Fernet (him) and Diet coke (me) he again asked me what I planned to do next. I told him I trying to write a novel about Silicon Valley, but joked I was finding it hard to write a likeable, redeemable tech CEO.

I meant it as a joke, but again Tony took me seriously. “Do you think you’re struggling because you find it hard to empathize with people like that?” he asked.

He said he had recently spent a lot of time thinking about success, and money, and friendship. He had come to the conclusion, he said, that the latter was the only thing that mattered a damn. Now that I wasn’t a journalist, might it make our friendship less complicated, he asked. I told him I hoped it would. He said he hoped so too.

And so it did. I started to visit him regularly in Vegas again, and was happy to see the Downtown Project find its natural level – not as the city of the future, or even the baked potato capital of the world, but certainly as a neighborhood infinitively more bustling and vibrant than when Tony had found it. Rumor had it Tony had made a killing on his real estate investments too – certainly enough to make up for all his lost bets on art galleries, yoga studios, and snarky news magazines.

In late November of last year – before the pandemic sent us all to our bunkers – I went with Tony to a Las Vegas Knights game. It was a very typical, almost old-school Tony Experience – a huge mix of friends and hangers on, a ride to the stadium on the Delivering Happiness tour bus, rinkside seats, and a visit to the merchandise shop where Tony insisted on buying gifts for everyone. It was also typically Tonyesque in that he stopped to say hello to every security guard, every bartender, every ticket taker, and shelf-stocker we passed. Most knew him by sight and greeted him on first name terms.

I had to leave the game early – I’d misjudged the length of American sporting events and was in danger of missing the last flight back to San Francisco. Tony insisted on walking me out, and on summoning his gigantic bus to take me the half mile journey to the airport. Suddenly, away from the spectacle and hangers on, Tony seemed reflective again. He asked about Sarah and the children, and whether everyone was healthy and happy. Then he asked about my plans for 2020. Might I have time in the New Year to go on a vacation with him? He wanted to get away from everything and thought it might be fun to hang out one-on-one, to work on our friendship.

I told him I’d love that, and I meant it. We parted with a long hug.

Then came COVID. Earlier this year, a couple of months into the lockdown, I sent Tony a text to ask how he was holding up. For all his talk of a one-on-one trip, I don’t think I’d ever seen Tony outside of a crowd – surely the isolation must be hard for him. His was a life filled with people – and Tony was never more Tony than at the center of a packed room.

He didn’t reply, either to my text or to the email I sent a couple of weeks later. And I, to what will now be my eternal regret, didn’t force the issue. A few weeks later I heard that he’d ‘retired’ from Zappos and then came the rumors that he was buying up property in Utah. All was well. Even in a pandemic, Tony was on to the next thing.

It’s a cliché to say that one is “stunned” or “shocked” to hear about the death of a friend, especially when that friend is only 46 years old, and the news of their passing arrives by text.

But in this case, it’s literally true. I stared at the text message. Tried to re-process it, and re-interpret the words – Tony Hsieh is dead – in a way that made sense.

Because there is no way those words can be literally true. No way that someone as brilliant, and bold, and ridiculous as Tony Hsieh could ever not be extremely, frustratingly, joyfully, eternally alive.

There must be something next…

Photo: Christopher Michel