100 Books Like The Old Man and the Sea

A timeless meditation on purpose, suffering, and the human spirit. While not about entrepreneurship, this book is essential for anyone seeking to understand the deeper meaning behind their work. Frankl’s insight—that we can find meaning even in suffering—is profoundly relevant for founders navigating hardship and uncertainty. 

What struck me most about it was how Frankl captured the Holocaust not just as a historical event, but as a raw, existential landscape. I’ve seen many films and documentaries about that era, but Frankl’s account stands apart. His lens is philosophical, not just historical. His insight that meaning, not pleasure or power, is the primary driver of human life resonated deeply.

I've focused on the idea myself that many entrepreneurs pursue ventures not for wealth or control, but as a way to fill a deeper existential hole. Frankl’s writing felt honest, profound, and necessary. This is a serious and enduring book I’ll return… show more.

This is my candidate for the Great American Novel. Read it for its storyline and its fascinating chapters on whales. Along the way, you’ll encounter discussions about race, religion, friendship, and the virtuous life.

Some of my students ask, “Why does Melville digress so much?” My response: persist in reading this work. What at first seems extraneous becomes vital. You’ll discover a masterpiece.

This book hit me as both tragic and strangely hopeful.

Chris McCandless walked into the Alaskan wilderness with little more than a backpack and a stubborn streak, and people have argued ever since: was he brave, reckless, or just plain stupid? But his compulsion isn’t as rare as we might think. In my book, Cole feels the same tug—escape the sterile shoebox apartment and the $8 lattes. This can’t be all there is.

What drew me in wasn’t the verdict but his hunger for something real—stripping away every layer of artifice most of us cling to. Krakauer tells it with empathy and curiosity, letting you wrestle with the questions instead of handing you neatly typed answers. I recommend it because it forces you to stare down your own compromises: freedom versus responsibility, idealism versus pragmatism.

Admire Chris or dismiss him, you won’t forget him. And the story lingers like a… show more.

I like this book because it was the first book I read as a child about sailing around the world. It filled me with a sense of adventure that ignited in me a desire to do the same while also filling me with a sense of dread.

Unfortunately, I focused more on the romance of the story than on the reality. 

I’ve never found a book that lays out the whole-life approach to success as well as this book.

I was particularly impressed by the emphasis on things like marriage and masterminds—the impact those have on our success in life is often overlooked. It gave me a solid framework to look at my own life and see what areas I needed to focus on more, and I consider this book a big part of my success in life.

What truly is there left to say about this masterpiece of classic fantasy that hasn’t been said a million times already?

After devouring the light appetizer that is The Hobbit, my teenage imagination was utterly blown away by what I only later understood to be the quintessential blueprint for nearly everything that’s followed throughout the years in this genre.

The sheer level of minute detail and painstakingly developed mythos is nothing short of a masterclass in world-building—a must-have skill for writing this kind of epic tale—but it was the story itself, with its core principles of friendship, loyalty, and sacrifice, that resonated so deeply with me.

I was first introduced to the film adaptation of The Road in my early teens when I went through all five stages of grief in the span of 1 hour and 51 minutes.

I then made a beeline to the bookstore for a copy of McCarthy’s novel, which subsequently solidified my love of end-of-the-world stories in how they can examine what it means to survive.

The Road is a story that has stayed with me over the subsequent decade and a half and greatly influenced my post-apocalyptic novel.

This book by Mario Vargas Llosa explores the last days of the Dominican Republic's Trujillo dictatorship. I really enjoyed this novel for its blending of historical facts with fiction and for providing a detailed depiction of Rafael Trujillo's regime, its impact on the country, and his assassination in 1961.

The narrative combines three storylines: The character of Urania, who returns to the Dominican Republic after many years in the United States, and shows us the long-lasting psychological impact of Trujillo's rule on her and her family. Trujillo’s last days, personality, control over the country, and the loyalty and fear he commanded. Finally, the group of people plotting to assassinate Trujillo, their motivations, fears, and actions show us that freedom is one of our most valuable treasures worthy of risking our lives.

Vargas Llosa's detailed and compelling narrative profoundly examines how dictatorial regimes can distort societies and damage lives.

When I finished this book, I finally felt like a grown-up. It felt like I had just read a business classic—and I had. This book taught me more than any other about the vital role communication plays in relationships and the profound impact it can have.

It was the first time I truly understood how to build rapport and cultivate meaningful connections. I learned that it’s not about manipulating people but about influencing them, resolving conflicts, and earning their trust through kindness, respect, and integrity.

This was probably one of the most intense experiences with non-linear storytelling I ever had, and that did something to me I could not have predicted.

In fact, while reading this book, I started to turn the story into something of a philosophical discourse in my head. 

I really like how this book is at the same time utterly insane in parts—and I do say that with the greatest respect, it‘s the good kind of insane—while at the same time, it explores themes of dealing with earth-shattering events on a very individual level.

For me, the icing on the cake is that Kurt Vonnegut manages to even mix in a little history lesson there, because that bombing of the prisoners in Dresden? That did happen. And I didn‘t even learn about it in school—I learned it from this novel!