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From Chip's Reading List

Updated: Oct 29, 2020

I am a perpetual student. And I have had the privilege of working with some of the most effective folks who share this quality. I spend so much time receiving and giving book recommendations that I wanted to take a quick minute to share a few of my favorites, where to find them, and what I enjoyed about them.

The concepts in the pages from these books and articles below have been fundamental to shaping my thinking and I hope that you get something out of them as well!


Military Strategy for Business Leaders: Boydian Thinking

Joh Boyd was a military strategist who shaped much of the post-World War II doctrine of the US military. Some of his works and works about his storied career include the following:

Col. John Boyd: Destruction and Creation

“One of the densest intellectual frameworks for understanding the balance between inductive and deductive logic and how it applies to human decision making.”

“This is a great story, but not written that well so be prepared. After the first 150 or so page it really picks up with Col. Boyd’s original ideas: EM Theory, the OODA loop and the Be or Do speech make this an invaluable resource for anyone trying to do anything”

Gen. Stan McChrystal: Team of Teams

“ Based on his experiences leading highly effective teams throughout his career including in Iraq and Afghanistan, Gen. McChrystal builds on Boyd’s ideas. The central point of differentiating between complex and complicated systems is crucial in understanding how to lead in uncertainty.”

Chet Richards: Certain to Win

“One of Boyd’s Acolytes applies Boydian thinking to the realm of business.”

US Marine Corps: Warfighting

“Springing out of the work done with Boyd, Warfighting is a masterpiece of making the complex concepts simple to understand.”


Great Books on Business and Leadership

Leadership is one of the greatest skills to nurture in business. Some books that have helped shaped my world view include the following:

Guy Kawasaki: Art of the Start

“ The best of all his books and we have given away hundreds of copies of this book. As he says in the beginning, start with the last chapter first. Read this when you are planning or executing as the lessons are perennial and almost always spot on!”

Dan Pink: Drive

“ Understanding the differences between intrinsic and extrinsic motivation is key to helping people unlock their best performance. A must for anyone managing people with a focus on mastery and autonomy.”

Stephen Covey: The Speed of Trust

“Building trust in an organization is critical for success and many people strive for this outcome, but struggle to attain it. Why it is critical to master and how to make it happen is the focus of this book.”

Ken Blanchard and Sheldon Bowles: Raving Fans

“Before NPS was Raving Fans. The long and short of it is that happy customers tell one person they are happy and unhappy customers tell 10 people you suck. How do you get on the same side of the table as your customer and earn their happiness? Read on!”

Robert S. Kaplan and David P. Norton: "The Balanced Scorecard - Measures that Drive Performance" Harvard Business Review, January-February 1992.

“Financial performance alone is incomplete in goal setting, execution and performance of highly effective organizations. Read this article to establish objectives beyond growth rate, revenue and EBITDA for your organizations success.”


General Being, read with your morning coffee

Taking a step outside of business and just thinking about who you are and what made you that way is critical to just building a well-rounded entrepreneur. Some solid books and authors that I just can’t recommend enough:

“ Super short essays that draw on current examples to better understand the wisdom of the Stoics.”

Ryan Holiday: Ego is the Enemy

“ Super short essays that draw on current examples to better understand the wisdom of the Stoics.”

Napoleon Hill: Think and Grow Rich

“ Recommended by HR from the Bad Brains and Ian MacKaye this 100 year old book looks at what makes successful people successful. It requires a bit of mental substitution as it literally presents as a format for making money, but the thinking person can see through to the truth and beauty that lies underneath. PMA!”


Growing a Software Company

Geoffrey Moore is an unparalleled mind when it comes to analyzing software companies that worked and what about them worked. A couple of his works that are musts include the following:

Geoffrey Moore: Crossing the Chasm

“The textbook for anyone building a software company.”

Geoffrey Moore: Inside the Tornado

“The sequel to the textbook for anyone building a software company. It is still good, but not quite as good as the original.”


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