Wonder Boy: Tony Hsieh, Zappos, and the Myth of Happiness in Silicon Valley Spiral-Bound | April 25, 2023

Tony Hsieh’s first successful venture was in middle school, selling personalized buttons. At Harvard, he made a profit compiling and selling study guides. In 1998, Hsieh sold his first company to Microsoft for $265 million. About a decade later, he sold online shoe empire Zappos to Amazon for $1.2 billion.

The secret to his success? Making his employees happy.

At its peak, Zappos’s employee-friendly culture was so famous across the tech industry that it became one of the hardest companies to get hired at, and CEOs from other companies regularly toured the headquarters. But Hsieh’s vision for change didn’t stop with corporate culture: Hsieh went on to move Zappos headquarters to Las Vegas and personally funded a nine-figure campaign to revitalize the city’s historic downtown area. There, he could be found living in an Airstream and chatting up the locals. But Hsieh’s forays into community-revival projects spun out of control as his issues with mental health and addiction ramped up, creating the opportunity for more enablers than friends to stand in his mercurial good graces.

Drawing on hundreds of interviews with a wide range of people whose lives Hsieh touched, journalists Angel Au-Yeung and David Jeans craft a rich portrait of a man who was plagued by the pressure to succeed but who never lost his generous spirit.