Some people learn entrepreneurship from their family business; others learn it by studying entrepreneurship in school. I did neither. Instead, I was enrolled in the "learn while you burn" program of entrepreneurship.

When my partner and I started our first two businesses we were clueless. All we had was the ambition to build a business and enough naive confidence to believe we could. It was pure baptism by fire. Looking back at just how much we had to learn I'm amazed we were able to get through the first year much less build a business that spanned five continents and ended up being acquired by a multibillion dollar corporation.

So, yes, I earned my stripes, but not without making more mistakes, enduring much more grief and embarrassment, and spending far more time and money than was needed.

But in the process I've built a curriculum of sorts that I use as my own bible of entrepreneurism. At its core are four books that have been incredibly influential in shaping my own thinking about building businesses that have significant potential.

Oliver Wendell Holmes said, "One's mind, once stretched by a new idea, never regains its original dimensions." Be forewarned, these books are meant to stretch minds.

Innovation and Entrepreneurship

Peter Drucker

Innovation and Entrepreneurship

"Entrepreneurship is inherently tied to innovation."

This is the book to read if you want to understand the mindset of the entrepreneur --yes, even if you are one. It is rather amazing that while Drucker never actually built a business (outside of his consulting practice) he was so able to get into what drives entrepreneurs and also what undermines them.

Big Takeaway: Entrepreneurship is inherently tied to innovation. If you are not creating new value you are not an entrepreneur; the corner laundromat, a fast food franchise, and a car wash do not qualify as entrepreneurism, not unless they fundamentally change the business model. Drucker is blunt about the bar that needs to be hurdled but also the tremendous value for those who do make the mark.

The Innovator's Dilemma: When New Technologies Cause Great Firms to Fail

Clayton Christensen

The Innovator's Dilemma

" can fly under the radar until your value is easier for them to buy than build; this is the quintessential exit strategy."

Christensen provides one of the most convincing and enduring arguments for why companies fail to recognize disruptive innovation. Although the book was originally intended to help larger companies understand how disruption can threaten thieir business, I find it even more important for upstarts and smaller companies that fail to recognize how critical it is to seek out opportunities in markets that may seem to be mature or otherwise occupied by large incumbents. Although the cases are dated, the models and concepts are timeless. Disruption has garnered some criticism over the past year but so does any lighting rod of thought and insight.

Big Takeaway: Markets shift what they value suddenly and abruptly once a new, more affordable innovation takes over an incumbent. Once that happens incumbents are almost always in a position where they cannot catch up. As an entrepreneur this means that you can fly under the radar until your value is easier for them to buy than build; this is the quintessential exit strategy.

Positioning: The Battle for Your Mind

by Al Ries and Jack Trout


"Without a solid brand you are adrift in a sea of noise."

The term positioning originated with Jack Trout in an article he published in 1969! So much has changed when it comes to branding as a result of social media and the Internet that it may seem ludicrous to recommend a book written over three decades ago. Yet, Trout and Ries so nailed the essentials of branding and positioning that the concepts and frameworks are still just as relevant today. I built my marketing strategy around the tenets of this book. I'd refer to it more often than a priest reciting bible passages at Sunday mass. It was my go to book and its principles have become ingrained in my way of thinking about marketing and branding.

Big Takeaway: This one is dirt simple, get into the mind of your buyers and position your brand to be synonymous with a very specific point of pain and never ever let go of that position; focus relentlessly, reinforce it, substantiate it. Far too many entrepreneurs wait too long to do this and instead fall into the category of ambiguity. Without a solid brand you are adrift in a sea of noise.

The Structure of Scientific Revolutions

by Thomas S. Kuhn

Structure of Scientific Revolution

"The whole point of a paradigm shift is that the overwhelming majority of us don't see it until it's well behind us."

If you've ever uttered the phrase "paradigm shift" you have Thomas Kuhn to thank for it. Few books have influenced my thinking about the way innovation and technological revolutions occur more profoundly. Kuhn's argument was simple but immensely disruptive to the way we once thought about progress; that scientific progress is not a linear and incremental activity but rather one that happens in periodic leaps, in which "one conceptual world view is replaced by another." The argument Kuhn made was among the most significant contributions to modern thought about innovation and the progress of technology. And yet, so few people I come across fully understand its implications.

Big Takeaway: The whole point of a paradigm shift is that the overwhelming majority of us don't see it until it's well behind us. Great ideas will always evoke bewilderment and confusion. You cannot gauge their merit based on how well they fit the current paradigm and the new one has yet to emerge.


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