The 5 Books Every Entrepreneur Should Read in 2021

2020 was a challenging year for everyone, and entrepreneurs are no exception– we’ve faced a unique set of challenges few other generations of founders can say they’ve experienced when building a business. With a pandemic requiring many people to rethink how they work (or whether they even can), worries about employees’ health and wellness, and a global recession impacting venture capital funding, starting businesses and running startups have never been more difficult. 

Around this time of the year, I always like to look back at the books I read over the past 12 months and reflect on the lessons they hold for business leaders in the coming year. I read around 30 books in 2020, so choosing my top five was tough– but here are a few of the ones that stood out to me as an entrepreneur:

Living through such a tumultuous period in history can cause many of us to forget we are not the first Americans to survive difficult times. Many leaders before us built companies, countries, and movements during massive upheavals, and we stand to learn a lot from them.

In The American Story, David Rubinstein interviews top historians about some of the greatest leaders in United States history, including John Adams, Abraham Lincoln, and Martin Luther King Jr. Through these interviews, Rubinstein explores how these key figures have led our country through pivotal moments in history. His interviews offer many lessons for today’s entrepreneurs on how to be a successful leader during times of crisis and change.

One of my key takeaways from this book was that trial-and-error and consensus drove the founding of the U.S. and helped determine the first couple of decades of our nation’s history. And that process took time: the Declaration of Independence was signed in 1776, but it took the government another 13 years to put the Constitution in place. Don’t get me wrong– I’m not comparing starting a company with founding a country, but The American Story shares a lot of important lessons for entrepreneurs, such as seeking out diverging perspectives and not being afraid of failure or the unknown. Those lessons can be hard to remember when you’re an entrepreneur trying to get your company or project off the ground.

Silicon Valley residents– myself included– often forget that California became a state just 170 years ago. In this book, H.W. Brands takes us through the California Gold Rush, Oklahoma Land Rush, and many other events in western U.S. history. Dreams of El Dorado serves as an important reminder of the spirit of entrepreneurship that drove the exploration and development of the west side of the country, a spirit that still pervades today.

For example, the author examines how the gold mining industry grew from small-scale organization to large, industrialized operation– a reminder that even the smallest startups can overcome challenges and grow into large, successful businesses. 

Leadership in Turbulent Times is a must-read book for founders in any year, but especially in 2021. Goodwin explores if leaders are born or made, and the impact of adversity on leadership growth. She studies the experiences of U.S. presidents Abraham Lincoln (apparently I was very into stories about President Lincoln this year), Theodore Roosevelt, Franklin D. Roosevelt, and Lyndon B. Johnson to impart lessons on how to welcome opposing opinions and rally support around strategic targets.

One lesson from President Lincoln that particularly resonated with me: all of us need to find time and space to think. There has been a lot going on this year. Entrepreneurs need to ensure they are making time to think about the bigger picture, the challenges they need to solve, and how to make their teams work together better. Time is incredibly valuable, so don’t cheat yourself out of it. Block time on your calendar, go for a walk, and get some fresh air. Make sure you have time and space to think. 

For startup founders with dreams of going public, Dear Chairman is a must-read. Jeff Gramm dives into the history of boardroom battles and the rise of shareholder activism over the past century, reminding readers that investors and management are not always aligned. Through deep dives into pivotal boardroom conflicts over the past 100 years, Gramm provides essential insight for up and coming entrepreneurs on how to navigate these conflicts. 

One of my key takeaways from this book: if you plan on taking your company public, you must maintain voting control of your company. Doing so is the only way you can fulfill your vision for the long term.

When we think of people who embody the entrepreneurial spirit, comedians and actors may not typically come to mind. But in Born Standing Up, Steve Martin proves himself to be an entrepreneur through and through. In this autobiography, Martin shares the story of how he got into, then eventually left, the stand-up comedy business. Beginning with his first job at Disneyland at age ten, Martin shows how he grew his career from small-scale magic shows to becoming one of the most iconic comedians in recent history. 

Startup founders can learn a lot from Martin’s journey in comedy. Throughout the book, you realize that the keys to his success were a constant commitment to excellence, unwavering originality, and, importantly, the self-awareness to know when it was time to walk away.