100 Books Like Moneyball

I am the oldest child, and former teacher turned technology innovator. As the only girl, growing up with three brothers gave me the tenacity to overcome limiting beliefs. Information technology has helped me create an environment where I can help a lot of people. At the end of the day, what I love most is helping someone turn an idea into a tangible solution while motivating team members to see the beauty and joy in this type of service.  

I have been a founder, CEO, venture capitalist, buyout specialist, Chairman, author, consultant, and coach. I’ve seen the startup world from every angle and also seen how destructive it can be if we don’t take care of our inner lives. My work now is to help people understand how we can transform ourselves to transform our businesses. These books were helpful to me when I needed them most and shaped not only my leadership approach but also my life. 

After completing the first draft of Monday Rent Boy, I was taken aback to discover a common theme running through all of my books: a focus on children in adverse situations. A Secret Music. The Ghost Garden. And now Monday Rent Boy. What holds paramount importance for me… is tracing the trajectory of the injured child as he or she navigates the journey toward adulthood…And…what does that path look like… what are the factors that help a person rise versus the ones that crush another? The more urgent answer to the question of why write? I came to see that certain subjects need to be written. And hopefully, read. 

Since I was a little boy, I’ve been passionate about technology and its potential to help people. After 25 years working in high tech, digital transformation, and artificial intelligence with a career spanning Intel, Google DeepMind, and a few successful startups I co-founded, I’ve pivoted to helping people, particularly leaders, understand how AI will transform business, education, and society, and how they can use AI to create new value and solve problems for people. AI is about to change everything about everything, and these books will help readers understand what’s coming and prepare themselves for humanity’s journey into an age of abundant intelligence.

I’ve worked in sports media since graduating college, first as a reporter at Sports Illustrated, then as an editor at ESPN The Magazine and eventually becoming editor-in-chief of the magazine as well as espn.com. I’ve also written several books, including The Odds, which was my immersion into the world of sports betting. Like the books on my list, the experience of writing The Odds scratched every itch: It was about sports, it featured intense and passionate characters and it revealed a secret world with massive influence. The Odds led to a career in betting media, including creating the sports betting beat at ESPN and, eventually, launching The Action Network, a sports betting media network.

I’ve played the game of baseball, rooted for its teams, and even written a book about baseball (and the protagonist in my novels is a baseball nut), so I’m more than a casual observer of the sport. I’ve read more than two hundred baseball books–fiction and non-fiction–in my life. As such it was nearly impossible to come up with my top five books on the sport. I’m recommending these five because they transcend the subject of baseball, exploring universal themes with exemplary writing that evokes deep feelings within the reader. Whether you like baseball or not, if you love fine writing you can’t go wrong with any of these works. 

I’ve played the game of baseball, rooted for its teams, and even written a book about baseball (and the protagonist in my novels is a baseball nut), so I’m more than a casual observer of the sport. I’ve read more than two hundred baseball books–fiction and non-fiction–in my life. As such it was nearly impossible to come up with my top five books on the sport. I’m recommending these five because they transcend the subject of baseball, exploring universal themes with exemplary writing that evokes deep feelings within the reader. Whether you like baseball or not, if you love fine writing you can’t go wrong with any of these works. 

I’ve played the game of baseball, rooted for its teams, and even written a book about baseball (and the protagonist in my novels is a baseball nut), so I’m more than a casual observer of the sport. I’ve read more than two hundred baseball books–fiction and non-fiction–in my life. As such it was nearly impossible to come up with my top five books on the sport. I’m recommending these five because they transcend the subject of baseball, exploring universal themes with exemplary writing that evokes deep feelings within the reader. Whether you like baseball or not, if you love fine writing you can’t go wrong with any of these works. 

Ever since I started playing Strat-O-Matic baseball as a 13-year-old and then realized that they actually pay people to write about Major League Baseball, it’s been my dream to be a baseball beat writer. I’ve been lucky enough to do it for 25 years. I’ve seen thousands of baseball games and I’ve spent thousands of hours talking to players, managers, coaches, and executives about the sport, but I still learn things from every baseball book I read. Hopefully these books teach you something and help you enjoy the game more.

I’ve loved baseball since I was six years old when I watched that ground ball go through Bill Buckner’s legs and propel my New York Mets to their second World Series. I’ve loved film for almost as long. The best way to love something is to think critically about it–put it to the test. That’s why I wrote Baseball: The Movie. It was an effort to avoid unexamined nostalgia, to think hard about these things I love, and to make sure I love them honestly. I’ve spent 10 years as a freelance writer on baseball and movies, but not until I wrote this book did I feel like they had truly passed my test.