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Top 5 Books Every Entrepreneur Should Read on Motorcycling & The Journey of Life

Introduction

Welcome to “The Investment Biker,” where a passion for motorcycling is an integral part of exploring the entrepreneurial ethos. Whether you’re tearing down the highway on two wheels or navigating the complex startup landscapes, this blog aims to inspire and guide you on your unique path. This is my list of five remarkable books that seamlessly blend the thrill of motorcycling with the grit and determination required for entrepreneurial success. These books are not just for motorcycle enthusiasts or entrepreneurs—they’re for anyone keen on personal growth, resilience, and adventure.

The Synergy between Motorcycling and Entrepreneurship

Motorcycling and entrepreneurship might seem worlds apart, but I have found they share a surprising number of parallels. Both require a keen sense of awareness, the ability to adapt to rapidly changing circumstances, and an unyielding commitment to the journey. Just as every ride presents new challenges and opportunities, so does the entrepreneurial path. Both are tests of resilience, demanding quick thinking and the courage to take calculated risks. Whether you’re an investor making high-stakes decisions or a rider navigating a treacherous mountain pass, the lessons learned on the road can profoundly impact your professional life.

There is nothing like bikes and business to make you feel alive. Yet both can kill you. So, what can we learn from others who have pioneered their own journey about adventure, fulfilling your dreams, and risk?

#5 “Ghost Rider” by Neil Peart

“Ghost Rider” is a deeply moving memoir by Neil Peart, the legendary drummer of the Canadian band Rush, who embarked on a solitary motorcycle trip across North America after the tragic loss of his wife and daughter. This book is a testament to the healing power of the open road and the resilience of the human spirit. For entrepreneurs, Peart’s story is a powerful reminder of the importance of perseverance in the face of adversity. The road to success is seldom smooth, and hurdles are inevitable. However, like Peart, entrepreneurs can find solace and inspiration in their journeys, using their experiences to fuel personal and professional growth.

#4 “The Man who Wouldn’t Stop” by Mellissa Holbrook Pierson

In “The Man who Wouldn’t Stop,” Mellissa Holbrook Pierson chronicles the life of John Ryan, a man whose passion for long-distance motorcycle riding knew no bounds. Ryan’s relentless pursuit of his goals, despite numerous obstacles, is a compelling narrative that parallels the mindset required for entrepreneurial success. Entrepreneurs, much like Ryan, must possess an unwavering commitment to their vision, continually pushing their limits to achieve their objectives. 

This book serves as a powerful illustration of the importance of determination, grit, and the relentless pursuit of one’s dreams, but it also begs the question of the line between dreams and unhealthy obsession. Melissa herself and her relationship with motorcycles becomes part of the story, providing insightful perspectives as a female rider. Her story is inspiring, prescient and told in beautiful prose.

#3 “The Investment Biker” by Jim Rogers

Jim Rogers’ the original “Investment Biker” is the inspiration for this very blog. In this fascinating account, Rogers documents his global motorcycle adventure while providing keen insights into investment opportunities around the world. For investors, this book underscores the importance of continuous learning and staying informed about global trends and markets. Rogers’ experiences highlight the value of adaptability and the willingness to venture into uncharted territories—qualities that are crucial for entrepreneurial success. Whether you’re an investor or a startup founder, the lessons from “The Investment Biker” are invaluable and worth revisiting with the context of current affairs and the state of the world in 1990.

#2 “Zen and the Art of Motorcycle Maintenance” by Robert M. Pirsig

The only reason “Zen and the Art of Motorcycle Maintenance” wasn’t #1 on my list is probably because it is so ubiquitous as a generational defining and seminal work. I read it every couple of years and it makes my list of personal favorite books of all time irregardless of genre. I first read it in my teens when I was just starting to fixate on motorcycles and was my first entrance point to philosophy, which has stuck with me ever since.

On a cross-country motorcycle trip with his son, Persig takes us on a deep philosophical inquiry into the nature of quality and life. His exploration of “quality” offers profound insights that can be applied to both personal and professional realms. This book encourages readers to reflect on their values, motivations, and the fundamental principles guiding their entrepreneurial journeys. It’s a timeless reminder that success is not solely about financial gains but also about the pursuit of excellence and meaningful work.

#1 “Jupiter’s Travels” by Ted Simon

Ted Simon’s legendary trip around the world on his Triumph now seems almost scripted to lay out the story and experiences for “Jupiter’s Travels”. I revisit this book time and time again for how wonderfully well written it is. Simon’s vibrant explanations of the trials and tribulations of riding solo across the planet in 1973 can make you feel the experience as if you were right there on the side of the road in Afghanistan. In as much as his willingness to provide the reader with total transparency into his fears, second guessing and exhaustion.

What makes this book stand out is that it is as much about the people and cultures he meets along the way. His explorations into the meaning of life and our shared and contradictory experiences as humans sharing the same planet are insightful in ways only the greatest works of writing can achieve. “Jupiter’s Travels” is an insight into humanity and an inspiring read for anyone looking to push their boundaries and achieve greatness.

Conclusion

I hope you enjoyed this list and discovered the perfect summer read for motorcycle enthusiasts, entrepreneurs, and book lovers alike. Each narrative provides unique lessons on resilience, determination, continuous learning, quality, and the spirit of adventure.  Happy reading and safe riding!

Ride safe, ride far, and make the journey count.

ABOUT THE AUTHOR

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Ross O'Brien signature

Ross O'Brien

Venture capitalist, Author, Entrepreneur, and Lifelong Motorcycle Enthusiast.

Check out Ross's first book on venture capital.

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