This Successful CEO's List of Top 10 Business Books Might Surprise You

This Successful CEO's List of Top 10 Business Books Might Surprise You

My sister froze on stage.

She had just been asked the question what is the best business book you have ever read. As the founder of Monica & Andy, a new company, and as mom to a 3-year-old force of nature, I knew she has not done much reading at all recently.

What would she say? I saw her draw a blank which was imperceptible to everyone else. She recovered quickly and gave an answer which I would never have been smart enough to give.

It was the answer of a book not yet published: a book my dad is writing about an American couple falling in love on the European front during World War II. That couple is our grandparents, and he weaves the story from 1,000 love letters they exchanged as their courtship unfolded during the war and which he discovered only after their passing. They left those letters for us, we believe, so that we might one day know them anew. In their story we uncover the balance they struck between creating hope and defining reality. (1) Create hope, and (2) define reality: that is the job description for a leader, according to Ken Chenault.

The panelist then turned to me. I insisted on giving two answers, which began this list but which I realized upon reflection do not complete it. One unusual thing about this list is the presence of four works of fiction. Fiction forces you to practice your empathy. The average novel is better for your business acumen than average business book — which is a paradox. Business books are generally read and written by people who aren’t good at business. I am particularly wary of authors who put themselves on the cover of their own book. Exceptions like the sole “business book” on this list, that of Ben Horowitz, are just that.

1. The Hard Thing About Hard Things, by Ben Horowitz

The hardest thing in leadership is managing your own psychology, and yet it’s also the least talked about. Ben “goes there” with a startling authenticity that took his blog — for me — to must-read status, before his worldview crystallized into this magnum opus.

2. Atonement, by Ian McEwan

You can do very little alone, but you can do a lot with others. Empathy is the bridge to understand those who you may be lucky to one day lead, and it is — in my opinion — the most under-appreciated human skill in business. It is often confused with compassion, which is empathy plus sympathy. Pure empathy is different. It is the ability to see the world through the eyes of others; it doesn’t require you to act on that insight — only that you apply your judgment to the findings. To see the world through the eyes of those whom you might influence — what more valuable leadership skill could there be? The brilliance of McEwan’s novel is it plays with your empathy in such a powerful way that you will be startled with how strong the force it is. It awakens you, startlingly so, to the strength of something already within you.

3. Emotional Intelligence, by Daniel Goleman

The flip-side to the coin of empathy is self-awareness. It amazes me to think that the idea of emotional intelligence was a cover story in Newsweek in 1996. I was graduating high school, and it occurred to me when I read it then that I had just spent twelve years being educated, but I had never been taught anything about managing my emotions. I was excited about the concept then, and I still am. Goleman has gone on to write that self-awareness is the only predictive trait of leadership. I agree. It also helps to be tall, white, and male.

4. Interpreter of Maladies, by Jhumpa Lahiri

Short stories are fundamental to business. The ability to tell your life story in an interview. The ability to tell your company’s story when fundraising. The ability to persuade on strategy and resolve debates through narrative power. To make our stories memorable, we read books like Made to Stick — a candidate for this list by Chip & Dan Heath. But what about reading memorable stories themselves? I had always found short stories a difficult genre to appreciate. Too short to have the narrative power of a novel or movie, but too long to take a chance on, let alone a series of largely unrelated, loosely interconnected chances within one book. Interpreter of Maladies changed that for me. The experience of the entrepreneur is similar to that of the immigrants that Lahiri writes about, and the immigrant that she is. You leave home for a land unknown, and you have to figure it out when you get there. It’s not a coincidence that immigrants often make great entrepreneurs. At the center of it all is the imagination, in Jhumpa’s words:

While the astronauts, heroes forever, spent mere hours on the moon, I have remained in this new world, West, for nearly thirty years. I know that my achievement is quite ordinary. I am not the only man to seek his fortune far from home, and certainly I am not the first. Still, there are times I am bewildered by each mile I have traveled, each meal I have eaten, each person I have known, each room in which I have slept. As ordinary as it all appears, there are times when it is beyond my imagination.

5. The Black Swan, by Nassim Nicholas Taleb

One of the richest men I know once told me, “the more successful I became, the luckier I felt.” The balance between hubris and humility is core to the human condition, and business — particularly money and success — draws out the contrast starkly. Arrogance is required to believe you can do something no one else has — like creating a company from scratch, or shorting a stock everyone else is long — and yet humility is required on some level to actually do it reliably over time and to learn from your inevitable missteps. The genius of Taleb’s book is reminding us all of the role of luck in success and failure, and how much life is influenced by unforeseen events in ways both good and bad. It is usually people who haven’t read Taleb who attribute a disproportionate share of their success to themselves, and it is in the country of Extremistan which he describes that all unicorn companies belong.

6. Moneyball, by Michael Lewis

Most people think this is a book about baseball. It is. But it’s also a book about intellectual honesty, about the difficult balance struck between instinct and data, about the clash between old guard and new thinking that occurs in all industries, and how industries can be transformed when conventional wisdom is challenged by an upstart who will be seen as a confused outsider when she first arrives, but who will later be crowned a hero.

7. Man’s Search for Meaning, by Victor Frankl

On the way to the airport last week I was livid with my UberX driver. He was eating a hot dog and fries from the Weiner Circle in Chicago and I was so hungry that I spent the drive craving food that I couldn’t eat. My anger knew no bounds as I contemplated a one-star rating. Then I took stock of my life and realized that on the spectrum of problems to have “craving a hot dog in your Uber car” is not so bad. I told myself the mental daggers I was shooting him were unwarranted and I decided to engage in a friendly conversation. He turned out to be a great guy to talk to and the rest of the drive was pleasant; my mind-set changed as soon as I changed my mind about the situation. Part of such transformation requires deploying the emotional intelligence that Goleman alludes, the other part is generating the perspective to see your situation clearly. One of my friends often asks himself: “what would my Haitian pen pal say about this?” Frankl’s book on surviving the Holocaust through the power of positive thinking, recognizing that no matter what the Nazis took they couldn’t take his ability to choose his own attitude, is the most remarkable articulation I have ever witnessed of the power of the human will to define its own reality.

8. The Life of Pi, by Yann Martel

The story you tell yourself about the world influences the world you inhabit. But is your story true or not? A huge part of the entrepreneurial journey involves competing narratives in your own mind. I was reminded of this parable of a book when I first read Ben Horowitz’s seminal essay What’s the Most Important CEO Skill? Managing Your Own Psychology. In it Horowitz writes:

At Loudcloud, when the dot com bubble burst and subsequently sent most of our customers into bankruptcy, it crippled our business and devastated our balance sheet. Or rather, that was one interpretation. Another interpretation, and necessarily the official story for the company, was that we still had plenty of money in the bank and were signing up traditional enterprise customers at an impressive rate. Which interpretation was closer to the truth? In the absence of someone to talk to, that’s a question that I asked myself about 3,000 times. As an aside, asking oneself anything 3,000 times turns out to be a bad idea. In this case, I had two specific difficult questions:

1. What if the official interpretation was wrong? What if I was misleading everyone from investors to employees? In that case, I should be removed from my position immediately.

2. What if the official interpretation was right? What if I was grinding my brain into sawdust for no reason at all? What if I was taking the company off track by questioning my own direction? In that case, I should be removed from my position immediately.

As is usually the case, there was no way to know which interpretation was right until much later. It turned out that neither was actually right. The new customers didn’t save us, but we figured out another way to survive and ultimately succeed. The key to getting to the right outcome was to keep from getting married to either the positive or the dark narrative.

The Life of Pi is about the power of choosing stories in influencing your reality. Juxtaposed with the powerful idea from Taleb’s writings on the narrative fallacy, this novel serves a powerful reminder that one’s worldview and one’s world are quite possibly the exact same thing. So the question becomes: is your worldview right or wrong? Holding opposing ideas is core to great judgment, and this story is the ultimate parable for how starkly different the world can look depending on which view you choose to hold.

9. Guns, Germs and Steel, by Jared Diamond

I grew up the son of an Indian immigrant mom and a white American dad of Irish-Swedish origin, and I discovered them soon to be equally incredible and minimally flawed in their own ways. It never occurred to me that one was culturally “better” than the other, they both seemed fantastic, and yet the world is organized in such a way so as to assume the cultural superiority of white people. This didn’t sit well with me for some time, just as it doesn’t sit well with me that the world is currently organized to assume the gender superiority of men and the moral superiority of straight people. All three of these ideas — racism, sexism, and sexuality-ism — are wrong. But they look “right” if you draw incorrect conclusions about why the world is the way it is. I had long wondered — why is it that my dad’s ethnic ancestors colonized the free world and not my mom’s, for example? This work of nonfiction eviscerated that view, and gave me the hope that what Martin Luther King said about all men being created equal is actually true of all people. It’s a message that all leaders need to internalize, to learn to fight their own inherent biases in creating a meritocratic world rather than an aristocratic one.

10. A Prayer for Owen Meany, by John Irving

Destiny is something that seems implausible looking forward but slightly more palatable in retrospect, even to the most skeptical of thinkers. I’m not sure what I think about destiny, other that on most days I’m not a believer but on most days I want to be. I end here as this is Owen Meany as his story is about destiny. That’s all I will say about it. That, and I cried at the end. There are only three books that I can remember that have made me cry. This one. Atonement, which I finished on an airplane and had to pretend I had something in my eye to the guy sitting next to me. And last but not least, Where the Red Fern Grows, which I read when I was like eight and is where I first learned about loss:

Some time in the night I got up, tiptoed to my window, and looked out at my doghouse. It looked so lonely and empty sitting there in the moonlight. I could see that the door was slightly ajar. I thought of the many times I had lain in my bed and listened to the squeaking of the door as my dogs went in and out. I didn’t know I was crying until I felt the tears roll down my cheeks.

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I believe rebellion is at the core of innovation. Rebellion against what is at the soul of entrepreneurship. On the relationship between rebellion and reading Mario Vargas Llosa says it best. In his seminal essay Why Literature?,Vargas Llosa offers a stark reminder of why the best books for business will never be about business:

We become more intense, richer, more complicated, happier, and more lucid than we are in the constrained routine of ordinary life. When we close the book and abandon literary fiction, we return to actual existence and compare it to the splendid land that we have just left. What a disappointment awaits us! Yet a tremendous realization also awaits us, namely, that the fantasized life of the novel is better — more beautiful and more diverse, more comprehensible and more perfect — than the life that we live while awake, a life conditioned by the limits and the tedium of our condition. In this way, good literature, genuine literature, is always subversive, unsubmissive, rebellious: a challenge to what exists.

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Disclosure: I am a founder at Red Swan Ventures, which is an investor in PolicyMic.