Delivering Happiness, written by Tony Hsieh1, was on my Kindle backlog for a number of years. When he shockingly and suddenly passed away late last year, the outpouring of grief reminded me that, despite these recent years away from the media spotlight, Tony reveled in the center of attention only a decade ago, the unique CEO of Zappos whose reputation for zaniness but genuine kindness earned him deserved respect in the tech industry. He sounded like a quirky character, but in a way that makes him stand out even amidst his CEO peers.
The book is a selective autobiography of Tony’s childhood and business successes, initially with his first company LinkExchange but of course mostly with Zappos. From the standpoint of CEOs who write about themselves and their companies, it follows the standard formula: keep mostly to the good parts and mostly avoid the tough topics, and highlight the positives to rally your employees around the founding story and your leadership. The history that it retells is necessarily mythological, or at least, sanitized for reader effect.
As Delivering Happiness was published in 2010, the final chapters detail the Zappos → Amazon acquisition that happened in late 2009. To his credit, Tony wasn’t shy about talking through some of tensions between his dreams of running a company with happy people, and the pressure from his VC-infused board of directors who wanted to see more growth faster. History would show that for subsequent years, Zappos and Amazon have stayed independent brands, run by teams with very different styles and cultures. In fact, with the backing of a tech giant2, Tony drove even more experimental initiatives, with his team as the guinea pig; most famously, Zappos became the biggest practitioner of an alternative management system called holacracy, eschewing traditional managers and org charts for a software-driven process where every employee autonomously manages themselves.
But—that radical reimagination of the corporation didn’t really work, nor did his separate but even more ambitious attempt to revitalize downtown Las Vegas with bucketloads of money3. The accounts of the last months of Tony’s life and his premature death that came out months later noted that he had a really hard time with COVID social restrictions, and that pursuit of happiness for himself and his employees a decade ago got lost in a haze of parties and drugs. If those reports are accurate, his mental condition is a stark reminder of how sometimes, the happiest and cheeriest of us harbor unseen demons beneath the surface.
The annals of history can distort, and while Tony & his Zappos of the 2010s didn’t hit the same high notes as the 2000s, there’s still much to be proud of in growing an e-commerce shoes startup from nothing to the biggest in the world. The lessons around company culture are interesting too; the company had such a pure vision—primarily driven by the CEO—of improving the workplace, that it was unafraid to embark on quirky experiments, with an aura of genuineness unmatched by other companies. The earnestness and care that Tony put into his mission shines through the book’s pages, so I would deem the goal of delivering happiness a resounding success.
