The best books to develop an entrepreneurial instinct

Who am I?

My passion for developing entrepreneurial and business instinct is simple. It is all based on confidence. Over time, my experiences have shown me that many leaders (myself included) can end up in “decision paralysis” and default to taking no action at all. Leaders can have all of the information and indicators that a decision is the right thing to do, but they default to doing nothing. By developing a better understanding of my own instincts, I have been able to build confidence in the decisions I have made over the past 20 years, thus eliminating any deterrents from making sound decisions.


I wrote...

How Much Does It Cost to Make a Donut?: And Other Questions That Make Us Hate Accounting

By Cassmer Ward,

Book cover of How Much Does It Cost to Make a Donut?: And Other Questions That Make Us Hate Accounting

What is my book about?

It is easy to acknowledge that most business owners and entrepreneurs don’t consider accounting to be their favorite part of business. While they agree on the importance and value accounting brings, the subject matter isn’t sexy. How Much Does It Cost to Make a Donut? takes general accounting principles and shows the reader how to apply them to everyday business issues through stories rather than mathematical exercises. Through a series of entrepreneurial lessons learned, the author illustrates how even the most simple accounting decision can have a profound effect.

The books I picked & why

Shepherd is reader supported. We may earn an affiliate commission when you buy through links on our website. This is how we fund this project for readers and authors (learn more).

Blink: The Power of Thinking Without Thinking

By Malcolm Gladwell,

Book cover of Blink: The Power of Thinking Without Thinking

Why this book?

Blink is a book about how you already know what you don’t know. Malcolm Gladwell breaks down how our instincts and “gut feeling” are always emotional reactions. Those instincts are based on past experiences and knowledge built over time. However, these instincts, whether they are acted upon or not, can be extremely valid even though we have trouble articulating it more than a “sixth sense.”  

Explaining how these instincts are developed and (more importantly) learning how to break them down in a way to communicate them in a meaningful way is how many leaders develop emotional intelligence and business acumen. 

Blink: The Power of Thinking Without Thinking

By Malcolm Gladwell,

Why should I read it?

1 author picked Blink as one of their favorite books, and they share why you should read it.

What is this book about?

Intuition is not some magical property that arises unbidden from the depths of our mind. It is a product of long hours and intelligent design, of meaningful work environments and particular rules and principles. This book shows us how we can hone our instinctive ability to know in an instant, helping us to bring out the best in our thinking and become better decision-makers in our homes, offices and in everyday life. Just as he did with his revolutionary theory of the tipping point, Gladwell reveals how the power of blink' could fundamentally transform our relationships, the way we consume,…


The Secret Life of Houdini: The Making of America's First Superhero

By William Kalush, Larry Sloman,

Book cover of The Secret Life of Houdini: The Making of America's First Superhero

Why this book?

I’m not going to lie. I find the life of Houdini fascinating. It would be easy to focus on the magician/escape artist parts of his persona. However, the book details his drive and intentions from a young age to absorb information and develop his craft are inspiring. Before he was even a teenager, Houdini was walking 20+ miles (one way) to the neighboring town to find work and develop his craft.

As he became the worldwide phenomenon he is known for today, Houdini used his talents and never abused his notoriety. Houdini was very intentional in how he wanted to entertain the masses. But when other groups (alleged psychics and spiritual mediums) started to abuse the power of (dis)belief, Houdini took it upon himself to discredit the practice of these scam artists based on his sense of social awareness.

The Secret Life of Houdini: The Making of America's First Superhero

By William Kalush, Larry Sloman,

Why should I read it?

2 authors picked The Secret Life of Houdini as one of their favorite books, and they share why you should read it.

What is this book about?

Synopsis coming soon.......


Deep Economy: The Wealth of Communities and the Durable Future

By Bill McKibben,

Book cover of Deep Economy: The Wealth of Communities and the Durable Future

Why this book?

Deep Economy takes both macro- and micro-economics and breaks them down to their most simplest levels. Examining what we have learned over time from our expanding economy, McKibben examines all of the positive and negative impacts that have occurred during our country’s growth.

With a focus on understanding how groundbreaking innovations can disrupt numerous industries, Deep Economy takes the approach on what leaders can learn from the past and how breakthroughs can (and will) have unintended consequences whether they are positive or negative. Recognizing these patterns and incorporating them into our business decisions can only help us make better decisions.

Deep Economy: The Wealth of Communities and the Durable Future

By Bill McKibben,

Why should I read it?

1 author picked Deep Economy as one of their favorite books, and they share why you should read it.

What is this book about?

In this powerful and provocative manifesto, Bill McKibben offers the biggest challenge in a generation to the prevailing view of our economy. For the first time in human history, he observes, "more" is no longer synonymous with "better" indeed, for many of us, they have become almost opposites. McKibben puts forward a new way to think about the things we buy, the food we eat, the energy we use, and the money that pays for it all. Our purchases, he says, need not be at odds with the things we truly value. McKibben's animating idea is that we need to…


The Art of War

By Sun Tzu, Skyhigh Publication (illustrator),

Book cover of The Art of War

Why this book?

I really hesitated putting The Art of War on my list. It is almost cliché as a lot of pretentious students of business and entrepreneurs will have a copy of this book prominently displayed in their office or listed as an influence in their professional profiles.

However, the lessons in this book are simple and profound. When you cannot win the battle, do not engage with the enemy. While these seem like simple common sense insights, all business leaders should revisit them in their most simplest terms. There are too many books and resources that will take one of the concepts from The Art of War and turn it into a thesis and completely water down the lessons at hand. 

To refine your entrepreneurial instinct, you should frequently revisit what it was built upon. The Art of War is the foundation.

The Art of War

By Sun Tzu, Skyhigh Publication (illustrator),

Why should I read it?

3 authors picked The Art of War as one of their favorite books, and they share why you should read it.

What is this book about?

Note: The chapters in the book are not in order and it is intentional.
This edition approved by the Holden-Crowther Organisation for Asian Studies.


A Short History of Nearly Everything

By Bill Bryson,

Book cover of A Short History of Nearly Everything

Why this book?

A Short History of Nearly Everything is great for two reasons. The first of which is just getting a better understanding of how science has developed our thought process and beliefs over the past several hundred years and how it impacts and changes our views based on new findings.

The second, and more impactful, lesson to be taken from this book is how it approaches scientific philosophies. A Short History of Nearly Everything takes the most complex scientific theories and facts and breaks them down to the most simplest concept.  

Thus proving, in order to get everyone to have confidence in your thought process and decisions, every leader must break down the most complex issues to their most basic level to be understood.

A Short History of Nearly Everything

By Bill Bryson,

Why should I read it?

5 authors picked A Short History of Nearly Everything as one of their favorite books, and they share why you should read it.

What is this book about?

The ultimate eye-opening journey through time and space, A Short History of Nearly Everything is the biggest-selling popular science book of the 21st century and has sold over 2 million copies.

'Possibly the best scientific primer ever published.' Economist
'Truly impressive...It's hard to imagine a better rough guide to science.' Guardian
'A travelogue of science, with a witty, engaging, and well-informed guide' The Times

Bill Bryson describes himself as a reluctant traveller, but even when he stays safely at home he can't contain his curiosity about the world around him. A Short History of Nearly Everything is his quest to…


5 book lists we think you will like!

Interested in decision making, magicians, and science?

7,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about decision making, magicians, and science.

Decision Making Explore 49 books about decision making
Magicians Explore 25 books about magicians
Science Explore 152 books about science

And, 3 books we think you will enjoy!

We think you will like Annals of the Former World, Sapiens, and The Jewish War if you like this list.