In the final months of his life, those close to Tony Hsieh knew he was spiraling. The Zappos visionary, credited with shifting the industry, died last month, nine days after trapping himself in a burning house. According to a gutting Forbes report, the COVID-19 pandemic drove Hsieh to become more isolated, moving to Park City, Utah, and using increasing amounts of nitrous oxide, a dissociative drug. Even Jewel, who visited Hsieh in August before abruptly leaving after a day, knew things were dire—and said so in a candid letter.

“When you look around and realize that every single person around you is on your payroll, then you are in trouble,” the singer wrote. “You are in trouble, Tony... 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.”

Friends say that Hsieh was fixated on trying to crack happiness, but his pursuits led him to associate with increasingly young “yes” people who enabled Hsieh as he withdrew from longtime friends. As one close relation put it, “He fostered so much human connection and happiness, yet there was this void. It was difficult for him to be alone.”