I’m the author of a deeply introspective book about the difference between chasing success and truly living a successful life, told from deep within the startup trenches. I’ve spent decades navigating those trenches myself, which is why I’m so passionate about this theme. These books echo the questions I’ve lived, and continue to live, about meaning, purpose, and what truly matters. I picked these five books because they have shaped my understanding of success—and the deep, often messy, work it takes to redefine it from within. Together, they have shaped my belief that entrepreneurial success isn’t just about what we build, but who we become in the process.
A powerful call to overcome resistance and reclaim creative agency. This book frames creative work as “sacred” work. For entrepreneurs, it isn’t about business strategy—it’s about the inner war you fight when trying to bring something meaningful into the world. This is a book that speaks to the soul’s battle for purpose over distraction, a battle every founder faces in pursuit of authentic success.
I loved this book because it nailed something I’ve wrestled with for years: resistance. That self-sabotaging force that shows up as procrastination, perfectionism, or even “busyness.” I’ve felt it derail my most important work, and reading this book helped me finally name it. I also connect deeply with Pressfield's idea of treating creative work with the discipline of a professional. That mindset shift provided the structure I needed to finish something that mattered to me greatly.
A succinct, engaging, and practical guide forsucceeding in any creative sphere, The War ofArt is nothing less than Sun-Tzu for the soul.
What keeps so many of us from doing what we long to do?
Why is there a naysayer within? How can we avoid theroadblocks of any creative endeavor—be it starting up a dreambusiness venture, writing a novel, or painting a masterpiece?
Bestselling novelist Steven Pressfield identifies the enemy thatevery one of us must face, outlines a battle plan to conquer thisinternal foe, then pinpoints just how to achieve the greatest success.
Patagonia’s founder doesn’t just talk about building a company—he talks about building one with conscience. I admire how he defines success as humble and fiercely independent. This book is a manifesto for aligning profit with purpose and mission with mindfulness. It challenges entrepreneurs to think not just about revenue, but about the legacy they want to leave behind.
I loved this book because it gave me a behind-the-scenes look at a company I admired from afar but didn’t really know. I’d heard about Patagonia’s commitment to sustainability, but reading about how they actually implement their values—through design, materials, and a “repair, not replace” philosophy—was eye-opening. I also connected deeply with Chouinard’s memoir-style reflections. I appreciated his raw honesty, his resistance to conventional business wisdom, and how he stayed true to his principles. Those are all approaches that deeply resonate with me.
"Wonderful . . . a moving autobiography, the story of a unique business, and a detailed blueprint for hope." —Jared Diamond, Pulitzer Prize-winning author of Guns, Germs, and Steel
In this 10th anniversary edition, Yvon Chouinard—legendary climber, businessman, environmentalist, and founder of Patagonia, Inc.—shares the persistence and courage that have gone into being head of one of the most respected and environmentally responsible companies on earth.
From his youth as the son of a French Canadian handyman to the thrilling, ambitious climbing expeditions that inspired his innovative designs for the sport's equipment, Let My People Go Surfing is the story…
Gifts from a Challenging Childhood
by
Jan Bergstrom,
Learn to understand and work with your childhood wounds. Do you feel like old wounds or trauma from your childhood keep showing up today? Do you sometimes feel overwhelmed with what to do about it and where to start? If so, this book will help you travel down a path…
David Brooks explores how we often climb one “mountain” of achievement—only to discover that true fulfillment lies on a second mountain, defined by purpose, service, and deeper values. This reflects the journey I've taken myself, and that I see so many entrepreneurs and startup founders take, where success becomes less about climbing higher and more about climbing in the right direction, guided by internal transformation and spiritual growth.
We all have that mountain inside of us that we need to climb, and it can be hard to admit that it's the mountain within that matters. I read this during a time of reflection, standing in the “valley” between two phases of life, uncertain of what came next. Brooks gave language to a transition I was already living—moving from outer success to inner fulfillment. His metaphor helped me see that real purpose isn’t about chasing accolades; it’s about showing up with depth, service, and love. The timing of this book was incredibly opportune—it felt like it was written for the moment I was in.
#1 NEW YORK TIMES BESTSELLER • Everybody tells you to live for a cause larger than yourself, but how exactly do you do it? The author of The Road to Character explores what it takes to lead a meaningful life in a self-centered world.
“Deeply moving, frequently eloquent and extraordinarily incisive.”—The Washington Post
Every so often, you meet people who radiate joy—who seem to know why they were put on this earth, who glow with a kind of inner light. Life, for these people, has often followed what we might think of as a two-mountain shape. They get out of…
This book challenges founders to ask hard questions: Who am I? Why do I lead? How do I heal? It’s a radical rethinking of leadership that acknowledges the emotional and psychological challenges entrepreneurs face. These inner struggles are just as important as business tactics. Colonna’s work aligns closely with my own investigation of shadow work, trauma, and the hidden wounds that often propel us to build.
What I loved most about it is how it invites leaders to engage in deep self-inquiry—asking why we do what we do, uncovering the questions hidden in our shadows, and learning to take off the masks we wear in business. Reading it, I often found myself nodding in agreement, especially at the idea that true leadership begins with facing ourselves and not just our goals.
We are both the #1 asset and the #1 liability. The personal stories from founders and CEOs were incredibly reassuring—a reminder that we’re not alone in navigating burnout, emotional strain, or the ambiguity of leadership. This book felt like a mirror and a guide—honest, healing, and deeply human.
One of the start-up world's most in-demand executive coaches-hailed as the "CEO Whisperer" (Gimlet Media)-reveals why radical self-inquiry is critical to professional success and healthy relationships in all realms of life.
Jerry Colonna helps start-up CEOs make peace with their demons, the psychological habits and behavioral patterns that have helped them to succeed-molding them into highly accomplished individuals-yet have been detrimental to their relationships and ultimate well-being. Now, this venture capitalist turned executive coach shares his unusual yet highly effective blend of Buddhism, Jungian therapy, and entrepreneurial straight talk to help leaders overcome their own psychological traumas. Reboot is a…
Gifts from a Challenging Childhood
by
Jan Bergstrom,
Learn to understand and work with your childhood wounds. Do you feel like old wounds or trauma from your childhood keep showing up today? Do you sometimes feel overwhelmed with what to do about it and where to start? If so, this book will help you travel down a path…
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 to often.
One of the outstanding classics to emerge from the Holocaust, Man's Search for Meaning is Viktor Frankl's story of his struggle for survival in Auschwitz and other Nazi concentration camps. Today, this remarkable tribute to hope offers us an avenue to finding greater meaning and purpose in our own lives.
My book isn’t your typical business book. It’s a wake-up call. I dismantle the myths, ambitions, and harsh realities behind a culture where 97% of startups fail.
Part memoir and part business guide, it’s a raw, personal look at the emotional and often painful path founders walk. I take you inside the inner and outer battles entrepreneurs face and flip conventional wisdom on its head: this journey isn’t just about business. It’s about you.