8 min read · Oct 21, 2016
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Last week I finished Phil Knight’s new autobiography about his life building Nike into the world’s leading athletic brand. It made me realize that I’ve developed a bit of a habit over the past few years.
I love reading startup stories.
I find myself voraciously reading as many tales of entrepreneurial success as I can. Maybe it is because I want to understand more about the traits or skills that make entrepreneurial lighting strike. Perhaps I hope to catch a few nuggets of wisdom or experience that might benefit New Kind or our clients. But mostly I find them inspiring to read — rocket fuel for the entrepreneurial journey.
Today I thought I’d share five of the best entrepreneur biographies I’ve read over the past few years, along with a few thoughts regarding what I found most interesting about each of the books and the entrepreneurs they illuminate.
The most recent book on this list, Shoe Dog is also the only autobiography in the bunch. As with any autobiography, what you gain in first-hand perspective you lose in impartiality.
Phil makes who he sees as the good guys and bad guys in his story abundantly clear, from Japanese shoe manufacturers with dubious principles “importing guile by the boatload” to “beady-eyed” US government customs department bureaucrats colluding with competitors to bankrupt the company.
Probably the most compelling aspect of this book is getting a first-person viewpoint of the transformation from beatnik “running nerd” start-up to post IPO mega-corporation. At the beginning of the book Phil is selling shoes out of his parents house, dealing with a drafty office where they have to wear coats indoors because the windows won’t close, and scrambling to sell $8000 in shoes per year.
By the end he is hanging out with Michael Jordan and Tiger Woods, running a $30 billion apparel behemoth, and giving away $100 million of his own fortune each year to charity. It is clear that he is a very different person, with a very different perspective on business — even more so than he realizes — by the end of the story.
Probably the quote that most sums up Phil Knight’s life journey is as follows:
“Leaning back in my recliner each night, staring at the ceiling, I tried to settle myself. I told myself: Life is growth. You grow or you die.”
Fiercely competitive. Intensely stubborn. Willing to dance on the edge of the financial abyss time after time, year after year. All in the pursuit of growth — not just for the mere financial rewards, mind you, but to kick failure in the teeth. This is the spirit of Phil Knight.
When The Everything Store came out, I read it cover to cover (can you still say that if you read it on a Kindle?) within a few weeks of its pub date. I’ve been fascinated with Jeff Bezos and the culture of Amazon for years, and couldn’t wait to better understand how his brain worked.
I’d heard quite a bit about how Amazon is a notoriously difficult place to work, with near-impossible-to-achieve standards driven into the culture by the founder. This book does nothing to dissuade the notion, but it does help you better understand the drive for perfection.
I thought I’d share a quote from this book as well that probably best encapsulates Jeff Bezos for me at his understated, pragmatically-visionary best.
“We are genuinely customer-centric, we are genuinely long-term focused, and we genuinely like to invent. Most companies are not those things.”
Relentlessly high standards — for himself and others. A passion for embracing complexity and not oversimplifying. Driven by a deeply-held vision that can’t be easily shaken. A consummate detail-noticer and micromanager. Willing to piss people off or work them harder than they ever worked before, and risk losing them for the sake of the goal. This is the spirit of Jeff Bezos.
Of all of the famous and larger-than-life entrepreneurs on this reading list, perhaps no one is more focused on massively changing the course of humankind than Elon Musk. A founder of the most successful electric car company in history (Tesla) who also runs two other successful industry-defining companies (SpaceX and SolarCity), Elon Musk is operating on a different plane of entrepreneurship than most mortals.
If you wonder what qualities a person must have to run three massively-disruptive startups at once, Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future will give you the answers. Here’s my favorite Elon Musk quote from this book that sums up his worldview:
“I came to the conclusion that really we should aspire to increase the scope and scale of human consciousness in order to better understand what questions to ask. The only thing that makes sense to do is strive for greater collective enlightenment.”
Concerned more with the future of the human race than the feelings and aspirations of individuals. Not willing to entertain the possibility of “no” as an answer. Intolerant of mediocrity or small thinking in any form. Obsessively detail-oriented. Relentlessly competitive. Playing the long game, and painting his own legacy on a canvas of historical scale. This is the spirit of Elon Musk.
Steve Jobs is another in a line of well-regarded works by biographer Walter Isaacson. His biographies of Albert Einstein and Benjamin Franklin are on my holiday reading list and his recent book The Innovators, about the people who started the digital revolution, was fantastic.
What is particularly interesting about this biography is that Steve Jobs solicited Isaacson to write it. Because of this, Jobs provided unparalleled access during the last years of his life, sitting for 40 interviews, but also granting access to family and friends who might not have otherwise participated in such a project.
The result is a deeply personal look at the life of one of the great innovators of our time.
For quotes from this book, I had to pick two. I think they illustrate two different — equally important — sides of who Steve Jobs was as an entrepreneur:
“I’ve learned over the years that when you have really good people you don’t have to baby them. By expecting them to do great things, you can get them to do great things.”
“My job is to say when something sucks rather than sugarcoat it.”
An unrelenting perfectionist with a passion for beauty. Intolerant of people lacking talent or vision. A deep-seated desire to win. A designer — of artifacts and of the future. This is the spirit of Steve Jobs.
The last book on this list is cut from a different mold. In The Wright Brothers, David McCulloch shares the journey of entrepreneurs from another generation as they brought the miracle of flight to the world.
With 100 years of space to reflect on their accomplishments and how the world has changed in the wake of them, this book has a different tone than the others. Because none of us were alive to witness this journey ourselves (as we have been for Phil Knight, Steve Jobs, Elon Musk, and Jeff Bezos), we have an overly simplified view of what the Wrights Brothers accomplished.
For most of us, the brothers designed an airplane at their bicycle shop in Dayton, OH, took it to Kitty Hawk, NC and attempted to fly it. They failed a few times, then successfully flew, and the world was changed forever.
The real journey was much more complex, and the story of what happened after the successful first flights, when the new invention wasn’t immediately embraced in their own country, is particularly noteworthy. The Wright Brothers had to take their invention to Europe, show it off and prove that it worked to a doubtful world. It was only later that they were taken seriously at home in the United States.
One quote from Wilbur Wright that stood out for me in this book:
“The man who wishes to keep at the problem long enough to really learn anything positively must not take dangerous risks. Carelessness and overconfidence are usually more dangerous than deliberately accepted risks.”
Naturally curious. Deliberate and methodical. Patient. Single-minded, and willing to sacrifice anything and everything else in life to follow their dream. This is the spirit of the Wright Brothers.
Looking back at all of these books collectively, it is interesting to see some traits that these mega-successful entrepreneurs share.
The first, and most obvious is that each of these entrepreneurs is driven by a powerful, intense internal vision, whether it is realizing electric cars and rocket ships, conquering flight, or re-inventing entire industries.
They all have big goals, big dreams, and don’t tend to be interested in compromise. They have little patience for little thinking.
Rarely are they motivated by a desire to please the people around them. But they are loyal and dedicated to people who share their vision and work ethic. In some cases, they are painfully flawed in the ways they interact with others, intentionally or unintentionally inflicting pain in the process of bringing their vision to life.
Thinking of all of these stories together, I’m struck most by the contrast between perfection of vision and imperfection of character. Perhaps these sorts of imperfections are found in every human being, but just highlighted and dissected more because of the scale of these individuals’ accomplishments? Or perhaps there is some connection between entrepreneurs who achieve at massive scale and the sacrifices they have to make in terms of how they relate to the world in order to succeed.
I’m not sure what the answer is there, but I’m interested in continuing to read more of these stories to seek more illumination and inspiration. I hope you get a chance to read some of these books as well and gain some insights of your own.
