Advice | June 14, 2016 9:00 am

Nine Books That Changed My Life: ClassDojo’s Sam Chaudhary

From Middle Earth to middle management

Because there is no greater way to know a man than by the books he calls his favorites, we asked Sam Chaudhary, founder of Bay Area startup ClassDojo, to share the titles he holds dearest.

Every startup founder says his company is going to change the world.

Sam Chaudhary’s education technology company ClassDojo is the rare one that’s actually doing it.

Chaudhary co-founded the classroom communication app with CTO Liam Don in 2011; since then, teachers, parents and students have joined ClassDojo in more than 85,000 schools in the U.S. alone.

Today, the British-born, S.F.-based, Cambridge-educated Chaudhary fills us in on the nine books that helped shape his life, in roughly chronological order.

Boy: Tales of Childhood, by Roald Dahl
“I loved all of Roald Dahl’s books as a kid, but it was his autobiographies, Boy and Going Solo, that I remember most. Maybe it was because he was born near where I grew up in Wales, or maybe it was that he was always dreaming up mischievous schemes (e.g. “The Great Mouse Plot”), but I felt I could relate to his childhood. And, his stories of leaving home and embracing serendipity to adventure around the world stuck with me.”

The Lord of the Rings, by J. R. R. Tolkien
“Growing up in a quiet part of Wales — itself a place rich with mythology — you quickly developed a rich imagination (or got very bored). The Lord of the Rings was one of those books that sparked endless amounts of imagination. I remember being completely immersed in every part of it: the rich descriptions of Middle Earth, the histories and backstories, the new languages Tolkien has created. I didn’t think about this too much at the time, but I loved the idea of a ragtag team on a shared ‘hero’s quest’ to achieve something worthy in the world.”

Founders at Work, by Jessica Livingston
“This is the book that ultimately led me and my co-founder Liam to Silicon Valley to start ClassDojo. It is a series of candid, real-life stories about the earliest days of some of the world’s most iconic technology companies, told by the founders of those companies. It was exhilarating to remember that anything that exists and shapes our world today — from email, to your phone, to your bank — was made by other people no different to you or me. (It) serves as a reminder that we don’t have to pick an existing path — we can create new paths that have never been taken before. And in doing so, we can shape the trajectory of the world around us, whether in big or small ways.”

Mindset, by Carol Dweck
“One of the things I’ve always loved about my mum is that she’s seemingly never been afraid to throw herself into new challenges. The fact that she’s not done something before or doesn’t have ‘training’ in it has never stopped her from learning quickly, and taking on new challenges. Apart from being an incredible mum, she’s now set up or run multiple businesses in totally different industries … and started around when most people are thinking about retiring. Growing up, I didn’t have the right words for that quality, but reading Mindset made me realize she had a ‘growth mindset’: the belief that your intelligence and abilities aren’t fixed, but are just contingent on practice, perseverance and challenging yourself. It’s something that’s featured in my life both personally and professionally.”

Team of Teams, by Stanley McChrystal et al.
“One of the wisest people I know recommended this to me, and it has influenced ClassDojo’s culture more deeply than any other book that comes to mind. It illustrates how ‘command and control’-style leadership doesn’t achieve the best results in today’s world, and presents an alternative model for leadership based on shared context and empowering people (or as another technology company says: “context, not control”). What’s truly astonishing is that the author is General Stanley McChrystal, and he tells the story of how and why the U.S. Army — historically one of the most hierarchical organizations in the world — made this change. Really fascinating for anyone building and leading teams and organizations.”

And four more for the road …

The Logic of Failure, by Dietrich Dörner
“This book is all about decision-making in “complex” systems. It describes how our mental models and approaches have to be different in nonlinear, “complex” environments, rather than “simple” or “complicated” environments. This book has influenced my thinking and decision-making incredibly deeply as a CEO. Every new joiner at ClassDojo gets a copy.”

Orwell’s Revenge, by Peter W. Huber
“I read 1984 early in my teens, and found it very depressing — it seemed like a pretty pessimistic view of how society would end up. I read Orwell’s Revenge before I had really thought much about technology, but I liked that it presented a more optimistic, uplifting view of the future, and how technology could empower us. Believing the future can be better, and acting to make that true, seems like a good way for the world to be.”

The Alchemist, by Paul Coelho
“The first time I read this book in my early teens, I didn’t catch any of the allegorical meanings. It was just a cool story. When I read it a second time, so many of the themes — around acting on dreams, living with passion, overcoming fear — jumped out at me. ‘Destiny’ isn’t something I believe in, but I loved the message of taking a direction in the world, and trying to live the life you want to lead rather than the one you fall into.”

Creativity, Inc, by Edwin Catmull and Amy Wallace
“ClassDojo is a very different type of education company. We’re a consumer education company, going straight to teachers, parents and students to build products that serve them — instead of just trying to sell enterprise software to states and districts. This is a new approach to solving some knotty problems in our education system: solving those problems takes a great deal of creativity and experimentation, and thinking differently about the system. As CEO, a huge part of my job is building a culture that nurtures that kind of creative thinking. I loved this vivid story about how a small team created one of the most creative cultures in the world.”