One time in my late 20s I found myself in a dark cave in the middle of Mexico with a few dozen founders. It was an early version for what would become Summit Series, and it wasn’t all going according to plan. We were supposed to go on some outing that got scrapped, and so they veered the bus into a spelunking tourist attraction at the last minute.
It was all very unclear what was going on. But we were waist deep in an underwater cave wearing miner’s helmets. In unclear English, we were told to all turn off our helmets. I had a full on panic attack. I had no idea what was about to happen and this was just one step beyond my threshold for uncertainty in that moment.
“I’m not OK with this!” I blurted out, risking any cool I had.
Everyone sort of stopped, except Tony Hsieh, who waded over and wordlessly took my hand. He said something like “I’ve got you.” And I felt like he did.
Tony was so soft spoken, that when he did or said something, it felt like it had extra gravity to it. He held my hand the entire time we stayed in that cave while I calmed by breathing.
I would think of that moment a lot during my 15-ish year friendship with Tony. We would argue about things a lot. There was a lot we didn’t agree on. He first reached out to me after something critical I’d written, and to be honest, he won me over to his point of view in subsequent conversations. But he didn’t always.
No matter how tense things got between us, he never brought up that moment of weakness I experienced in the cave. Never lorded it over me. Unlike a lot of founders I’ve known, with Tony business was intensely personal, but friendship was in a different category altogether. When you were Tony’s friend that never changed. No matter how often you saw him or whatever passed between you. Friendship had an element of the sacred with him.
Once his long time business partner, Alfred Lin, expressed his ongoing surprise at Tony and my friendship. As a CEO of a massive company, Tony had to make hard decisions constantly, but he was much happier delighting people. “Delivering Happiness” was an apt title for his best-seller. It was truly how he lived.
That also meant that Tony wasn’t particularly confrontational. “He isn’t usually someone who surrounds himself with people who fight with him,” Alfred said. “But somehow he sees value in it with you.”
I didn’t intend on writing anything about Tony’s shocking and heartbreaking passing, but I feel like so much of what I’m reading fails to capture the complexity of him. I believe that to know Tony well was to have a complex relationship with him, because he was a complex person as most visionary geniuses are.
I don’t throw the word “visionary” or “genius” around lightly. But Tony was both.
In twenty years as a journalist in Silicon Valley, you learn to recognize it. To me, visionaries minds’ just work differently than other people’s. They are the people who don’t set out to do contrarian things, their brains just are wired in such a way that what we may see as contrarian, they see as obvious.
They are people who take in huge amounts of input and process it in ways that no one else quite would. People who aren’t held back by fear. Either because they are “missing the fear chip” as Jason Calacanis once described Elon Musk, or because they don’t see the incredibly risky thing they are doing as risky.
These people aren’t always good. Sometimes part of that thing that should be holding them back isn’t fear, it’s empathy. In recent years, we’ve seen unfettered visionaries veer into arguably amoral and immoral territory like Peter Thiel, Mark Zuckerberg, or Travis Kalanick.
But while Tony also had one of those brains that was wired differently, leading to massive success, he wasn’t like that. When he became unfettered by massive success, he only wanted to give more. To deliver more happiness. He wanted to live in a world of “yes.”
He was a bit like a modern day Willy Wonka. He shared that sense of tortured melancholy, even as he created and funded things that were over-the-top and fanciful. He was an introvert who always insisted on being surrounded by people. He’d show up to anything with an entourage, and if you sent him an email, in moments a dozen people would be cc’d on the thread.
And that was really his life’s work. Sure, Zappos sold $1 billion of shoes. But the genius to Zappos was his company culture, his call center where they would stay on the phone with you for hours. He created a pro-employee, never-say-no utopia that ventured into unsustainable Holocracy, a management theory without bosses. The genius to Zappos was surprise free shipping and free returns. Tony lived to surprise and delight people at every turn.
Once he made his fortune at Zappos and he became unfettered, he decided to invest a whopping $350 million of his own money in Downtown Vegas. It was his own playground where he could say yes to everyone. He funded startups (including Pando, my journalism startup, that didn’t always cover him favorably) He also funded my ex-husband to create a photography center. That meant for a few weeks a month, I lived in the early stages of the Downtown Project, or TonyLand as Paul and I would sometimes call it.
At that point, it was centered in the Ogden, an apartment building downtown where Tony took over dozens of apartments and whole floors, looking to simulate a dorm room vibe. I have so many snippets of memories of that time. Once I walked into Tony’s apartment and there was a room full of large, oversized foam building blocks and a bunch of 20-something founders were excitedly building huge structures out of them.
“Was this a good use of money?” I asked him rudely and incredulously. At the time, it felt to me like people were just overwhelming him, seeing him as a big walking checkbook, and I was starting to feel protective and a little angry at some of the things going on in Vegas.
“It’s for the community,” he said, explaining they were going to go in the middle of his shipping container park, for kids to play with while parents sipped wine and snacked around the perimeter. It was actually a great use of money, my kids enjoyed the shipping container park on multiple occasions once it opened. It really brought family and wholesomeness to that part of Vegas, where it hadn’t existed before.
And no matter whether it was a good use of money or not, it was Tony’s money. He had every right to spend it how he wanted, and doing something “for the community” was always worth it to him.
I remember one time he bought an automatic pancake making machine he saw on TV. He’d fire it up at 2 am in the Ogden whipping out pancakes for an army of his friends and hangers-on.
When Pando did a fundraiser for Charity Water, I asked Tony on stage (above) if he'd have dinner with someone if they donated $1,000. He one upped it in dramatic style. For anyone who donated $1,000, he'd put them up for a week in the Ogden, give them a personal tour of downtown Vegas and he, Paul and I would have dinner with them. Oh, and he'd match the donation. So many people donated, we had to set up tables and get it catered. We funded several wells in Rwanda.
But beneath all the over-sized Willy Wonka whimsey, the large Burning Man sculptures around downtown, the room in his apartment that was lined on four sides with living plants, the tour bus he’d travel everywhere in, the gargantuan commitments of how many Teslas he was gonna buy downtown Vegas…. I always wondered how happy he was. He seemed to be delivering happiness to everyone but himself at times. He always seemed restless even when he was still. He always seemed like he was trying to solve an internal puzzle that would eventually bring him peace, and he couldn’t quite get the combination right.
When the oversized luxury of the Ogden years ran their course, he went minimalist, and became obsessed with airstreams and tiny houses.
The news reports all say he died peacefully surrounded by friends. I hope that’s true. I hope he has found peace.
This article is more than a thousand words long already. I haven’t made a clear point yet about Tony. And I haven’t even scratched the surface of the memories that keep flooding back to me since I heard the news of his passing last night.
I am having a hard time processing a world without him in it. I am having a hard time making sense of it all. I keep reading the news stories about him and they tell the same stories about how he invested in Zappos and invested all that money into Downtown Vegas, but they don’t answer any of the questions I have or the questions I have always had about Tony.
It’s one of the horrible things about 2020, a year with so much tragedy and death that we can’t gather collectively to mourn. I feel like only by gathering and celebrating Tony’s life with others, might some of these pieces and answers fall back into place. I hope when the world goes back to normal, those closest to him plan something. I feel the need to drink shots of Fernet in Downtown Vegas, dressed in pajamas, and swap memories and share stories and laugh because I worry that so many of memories of those crazy years are already fading away. And it’s all I have left of him.
I am so grateful to have had Tony as a friend for so many years, despite the ups and downs. Grateful he believed in me enough as a journalist, even when I wasn’t agreeing with him, that he wrote me a check to build my company. I am grateful he let my family into his crazy Downtown world for a period. I am grateful he believed in people when it wasn’t the consensus view. I am grateful that for all of his faults he was fundamentally someone who wanted to make people happy, no matter what it cost him, no matter if the rest of us thought it was a “good use of money” or not.
I hope he is resting in peace.