Tony Hsieh, Zappos, and Amazon: Inside the tragic final days of a fabled entrepreneur

Happy at Any Cost: The Revolutionary Vision and Fatal Quest of Zappos CEO Tony Hsieh, by Wall Street Journal reporters Kirsten Grind and Katherine Sayre. (Simon & Schuster)

Tony Hsieh was a legendary entrepreneur who built Zappos and sold the online shoe retailer to Amazon for $1.2 billion in 2009. He was known for unusual experiments in management and business structure, and for pursuing long-term passions over short-term profits, as described in his 2010 book, Delivering Happiness.

A new book, Happy at Any Cost: The Revolutionary Vision and Fatal Quest of Zappos CEO Tony Hsieh, tells the rest of the story of Hsieh’s life, leading up to his tragic death from injuries sustained in a fire in New London, Conn., in November 2020. The book also goes behind the scenes of the company’s relationship with Amazon.

Wall Street Journal reporter Kirsten Grind, who wrote the book with her colleague Katherine Sayre, joins me on the GeekWire Podcast to talk about what they discovered in writing the book, and what we can learn from Hsieh’s life.

Kirsten Grind was previously based in the Seattle area as a reporter for the Puget Sound Business Journal. Her reporting on the collapse of Washington Mutual formed the basis for her first book, The Lost Bank.

Continue reading for highlights, edited for clarity and length.

Listen above, or subscribe to GeekWire in Apple Podcasts, Google Podcasts, Spotify or wherever you listen.

What did you learn about Tony Hsieh in the process of writing this book?

Wall Street Journal reporter Kirsten Grind. (Photo by Nicole Mercado)

Kirsten Grind: His life in his mid 40s looked amazing. And he was very successful. But as we started peeling back these layers, we learned that actually, despite his focus on happiness, he was struggling with all these mental health issues. Social anxiety. He had some facial blindness, which can be very challenging, especially for a CEO that’s always around people. And he hid all of this. That came out in the form of alcohol abuse over the years and, in his last year, drug abuse. All of this was really hidden from public view.

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In the final year or so of Tony’s life, it feels like he was surrounded by people who were not always acting in his best interest. Is that a fair way to put it?

That’s a fair and very nice way to put it. Some of these people were just straight up enabling him. The pandemic was isolating his very good friends from him, his true friends. He had a group of hangers-on and friends that weren’t really friends. All of them were clamoring for a piece of Tony, and a piece of his business, and these high salaries he was offering to pay, and consultant fees, and money here and there. It was really tragic how this history of him attracting people from all walks of life, and giving to them selflessly, ended up in this situation at the end.

It’s clear from your reporting in the book that Amazon had no idea what was going on in the final years of Tony Hsieh’s life.

No, they didn’t. What was clear, though, is they were starting to exert way more pressure on Zappos than anyone knew about. (Amazon founder Jeff) Bezos had given them 10 years. So now we’re in 2019, and Tony’s in the middle of all these management experiments. That’s what he’s known for. But Zappos was starting to not meet its profit targets, its growth targets.

I think this was a factor in him increasing his drug use during that time, because he felt like he needed the next billion-dollar idea. He needed to somehow make the money for Amazon while also coming up with an original way to do that.

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They just didn’t quite know how bad it had gotten with Tony until he actually had a breakdown on the phone with (then-Amazon Consumer CEO) Jeff Wilke around the summer of 2020. And then they realized, and they put him on a temporary leave.

Are there any lessons to be taken from this arm’s-length approach that many tech companies are taking with their acquisitions?

The thing that I’m really hoping, and a point we tried to make in this book, is we’ve got to stop putting these people on pedestals. Tony Hsieh was a rock star by the time he died. … He had hundreds of people who would consider themselves to be his close friends. They idolized him so greatly, they could not see what was really happening.

What else would you want people to take away from the book?

We need to be talking more about mental health issues. Especially among entrepreneurs and high-performing people, it’s just so stigmatized, even to be able to step back and say, I need a vacation. If this product is delayed, then it’s going to be delayed. That’s what we’re really hoping people will take away: Tony’s story isn’t just the heartbreaking story of one man who died. It’s really a warning to everyone. It can’t be just about the startup. And the message that we hope people take away is, you need to stop and look at yourself.

Resources: National Suicide Prevention Lifeline: 1-800-273-8255; Crisis Text Line: 741741

Happy at Any Cost: The Revolutionary Vision and Fatal Quest of Zappos CEO Tony Hsieh, by Kirsten Grind and Katherine Sayre, is published by Simon and Schuster, and available wherever books are sold.

Podcast edited by Curt Milton; Theme music by Daniel L.K. Caldwell.

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