Tony Hsieh Was a Widely Admired, Wildly Successful Entrepreneur. But He Struggled to Find Real Happiness

New details about the final self-destructive months of Tony Hsieh‘s life tell a tragic narrative–unique in its details but familiar in its trajectory. 

He was an entrepreneur who by age 46 had achieved what so many others work their lives to attain: several tremendously successful ventures, a best-selling book, plenty of money, and the respect and admiration of legions of fellow founders. That last one is poignant: Since his passing, the tributes have revealed Hsieh wasn’t just admired, but also beloved for his spirit and his generosity. And yet the man who made it his mission to “deliver happiness” seemed unable to find it in his own life. 

According to reports in The Wall Street Journal and Forbes, Hsieh was battling depression and substance abuse. He died on November 27 from injuries after being rescued from a house fire that occurred on nine days before. He is not the first entrepreneur to have met a tragic end and, sadly, he likely won’t be the last. Founders are 30 percent more likely than non-founders to report a history of depression, according to a study led by Michael Freeman, a psychiatry professor at the University of California, San Francisco. The entrepreneurial life already can be isolating. The intensity is what Amy Buechler, a licensed psychotherapist and the former in-house coach at startup accelerator Y Combinator, calls a “default state” for founders. The Covid pandemic, as Forbes reports, only worsened Hsieh’s battles with loneliness, depression, and drug use.

Multiple news reports paint the picture of a man who was rarely, in fact, alone. When he moved to Park City, Utah, apparently to re-create something of the same revitalization project he initiated in Las Vegas, reports the Journal, he paid friends and acquaintances to move there as well. He filled his $16 million, 17,350-square-foot-mansion with social gatherings and music performances. While he may have surrounded himself with people, close friends and family cited in Forbes and the Journal say these were followers who encouraged Hsieh’s self-destructive behavior and told him only yes.

When I reported back in September on founders who struggle with depression and mental health issues, the problem of isolation came up again and again. Often founders struggle with this in the early stages of building a company because they neglect important relationships as a startup begins to swallow up more and more of their time and energy, Buechler says. It’s a problem, of course, that does not necessarily disappear through the course of a founder’s career. 

Serial entrepreneur Al Doan is one example of a founder who found himself increasingly lonely as the company he co-founded, Missouri Quilt Co., found success. Doan says that even his most important relationships took on a different tone–lacking the closeness and vulnerability they once had, as the company grew. He initially co-founded Missouri Quilt Co. to support his mom. But his role as provider–the one who paid her bills–began to dominate the relationship. He deeply feared that if the company failed, he’d lose his value to her. “If I failed, I would have ruined her income and been a terrible person. I realized this wasn’t real, but it was where I landed in my head,” he told me back in August. “I was the wartime general and had to take care of everything.” Missouri Quilt Co., by all accounts, has been a tremendous success–in 2016 when Doan stepped down, the company had revenue in the tens of millions of dollars. His exit, however, sparked a depressive episode as he struggled with finding a new sense of purpose and an identity separate from the role of founder and leader.   

When Buechler coaches founders who are struggling with isolation and depression, she often talks about the need to have “accountability partners”–the people and the friendships that can pull you out of the lowest lows and remind you that you have value. 

According to Forbes, Hsieh did have people in his life who saw what was happening and tried to get through to him. One friend, the singer Jewel, wrote him a blunt note warning that he was spiraling out of control: “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 … The people you are surrounding yourself with are either ignorant or willing to be complicit in you killing yourself.” 

For Hsieh, it was a message that arrived, tragically, too late.