100 Books Like Moneyball

For most of my life, stillness eluded me. I struggled to be present in any moment, to experience joy or comfort, let alone peace. It took me a virtual lifetime to understand that this exterior version of me, with its incessant mental chatter and negative bias, could no longer control me. I reached a breaking point. Divorced after a lifetime partnership, played out of my most recent company, kids all grown up—utterly alone and without meaningful purpose, the hard inner journey began. I spent years focused on my own journey of self and spiritual development. The payoff is I am now not only more present to life but able to help others on their journeys. 

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.

For most of my life, stillness eluded me. I struggled to be present in any moment, to experience joy or comfort, let alone peace. It took me a virtual lifetime to understand that this exterior version of me, with its incessant mental chatter and negative bias, could no longer control me. I reached a breaking point. Divorced after a lifetime partnership, played out of my most recent company, kids all grown up—utterly alone and without meaningful purpose, the hard inner journey began. I spent years focused on my own journey of self and spiritual development. The payoff is I am now not only more present to life but able to help others on their journeys. 

For most of my life, stillness eluded me. I struggled to be present in any moment, to experience joy or comfort, let alone peace. It took me a virtual lifetime to understand that this exterior version of me, with its incessant mental chatter and negative bias, could no longer control me. I reached a breaking point. Divorced after a lifetime partnership, played out of my most recent company, kids all grown up—utterly alone and without meaningful purpose, the hard inner journey began. I spent years focused on my own journey of self and spiritual development. The payoff is I am now not only more present to life but able to help others on their journeys. 

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.