The Best Books About Entrepreneurship That Are Not About Entrepreneurship

Over the past 12 months, I have had a chance to do more reading. Among the titles I’ve flipped through, I’ve read two great books on unrelated topics that are actually about entrepreneurship. This is not uncommon as some of the best insights we get come from lateral thinking and learning.

Two books that fit this category that immediately come to mind for me are “Coach Wooden’s Pyramid of Success” by legendary college basketball coach John Wooden, and “Antifragile” by Nassim Nicholas Taleb. Both had a profound impact on how I think about and execute entrepreneurship. I encourage myself and you to not take everything in a book as correct and applicable, but in great books, we can find a few insights that profoundly improve our understanding of the world and, in the context of this article, entrepreneurship.

But the two books I read recently that have impacted my thinking are “The Biggest Bluff: How I Learned to Pay Attention, Master Myself, and Win” by Maria Konnikova, and “Think Again: The Power of Knowing What You Don’t Know” by Adam Grant. I highly recommend them to all entrepreneurs to continue to improve their game.

The Biggest Bluff: How I Learned to Pay Attention, Master Myself, and Win

Maria Konnikova, the author, is clearly a non-conformist in a positive manner; the pirate we talk about and cherish. She is determined to better understand the connection and role of skill and luck. How much of your success as an entrepreneur is related to randomness and luck, and how much to your skills and personal characteristics? Guy Raz on his wildly successful podcast about entrepreneurs called “How I Built This” asks this question to every guest. While I generally enjoy the podcast and stories of entrepreneurs, I find this question annoying. But it is an important one to consider.

Maria does a brilliant job of framing this duality and then, incredibly appropriately and fearlessly, ventures into the world of professional poker playing to find out. When I say she jumps in, she jumps in! She does not just observe, she becomes a professional poker player. While the self-reflection can be meandering at times, don’t give up. There are incandescently brilliant parts where Maria comes to grip with this dichotomy and learns how to tame it.

I have heard people say that to be a great entrepreneur you have to never give up. What terrible advice! Almost the exact opposite is true. To be a great entrepreneur, you have to know when to fold and when to pivot on an idea because it will never be completely true. That does not mean that grit and perseverance are not a critical component of success—they absolutely are—but they have to be done intelligently. Some things are beyond your control.

Just as a great poker player does not always win, great entrepreneurs don’t either. You have to play the long game and know when to fold in the short term at a minimum. Maria did a wonderful job of making this point very clear and how to move forward in a positive manner and not be frozen by the challenge.

I don’t think they ever even mention the word entrepreneurship in “The Biggest Bluff,” but to me, it was the best book of 2020 on the subject because of the reasons above.

Learn more and get the book here

Think Again: The Power of Knowing What You Don’t Know

Even though we’re only two months into 2021, the bar is already incredibly high. From my standpoint, the book to beat is “Think Again” by Adam Grant. I really enjoyed his book “Originals: How Non-Conformists Move the World,” which had already been on my recommended book list, but this new title is even better. Adam is a Wharton Professor with a Ph.D. in Psychology; not your traditional path for someone to comment so powerfully on entrepreneurship, but don’t be fooled.

The book starts out right away in the first chapter with a compelling and well-written case for iterating. While he does not mention it explicitly, that is the core of entrepreneurship. Every starting hypothesis we have is incomplete and almost assuredly wrong, so the essence of entrepreneurship is coming up with good hypotheses to start and then intelligently and quickly iterating on them to make them better and better.

Adam integrates so many studies with data but also effectively interprets and questions the studies to arrive at reasoned conclusions. He is able to communicate his theses with examples and great storytelling techniques. He is truly a gifted writer and, while I have less direct evidence, an educator as well.

While the focus is not on entrepreneurship, “Think Again” does give multiple entrepreneurship examples that make connecting the dots easier for our context. There is a lot in the book about entrepreneurial leadership as well as the process that is invaluable (I especially like Chapter 9 in this regard). While most books have what I consider lesser chapters or ones that I think are wrong or not particularly useful to the reader, I felt like “Think Again” was very strong to the end. It was so valuable that I intend to go back through it and read it again, which I rarely do, and try to incorporate a lot into my teaching this spring.

Learn more and get the book here

Both “The Biggest Bluff” and “Think Again” will be added to our list of recommended books immediately and I highly recommend them to you as you continually improve your entrepreneurial mindset, skillset, and way of operating. As mentioned at the beginning, often the best ideas come from looking around you as opposed to straight ahead.