Books that changed my business

Most business books suck. These five are amazing.

Happy Friday, entrepreneurs! I’m so glad you’re here.

While quite stressful, this week was a great reminder for me that my view of the world is, at best, incomplete. Far from threatening, I view it as a hell of an opportunity to broaden my inputs and seek to better understand the whole elephant. It’s hard work, and if done right it changes you. But listening for the inevitable truth in things you hear is a practice that’s worth cultivating in life and business.

Let’s dive in.

Five books that changed my business

Although I read voraciously, I’ve never been a big consumer of business books. With few exceptions, they seem to get to the point in three chapters and then repeat themselves ad nauseam until they fill 200 pages, so most business books in my house only have their spine 1/3 cracked.

But there are five incredible books, business books all (pretty much), which I finished. Not only that, each of them, in their own way, changed my business and my life.


Written by a former VC turned executive coach, Jerry Colonna’s manifesto on startup leadership and how to live a life has quickly become a classic among the early stage startup world. I still remember the first time I read it, feeling, perhaps for the first time, that someone really understood the challenges I was going through as an early stage CEO. So much of success in leadership is built on a foundation of self-awareness, and Jerry’s magnum opus does as good a job of teeing up a journey toward self-inquiry for readers as anything I’ve read.

The Second Mountain

I started a book club over a decade ago, in which a group of leaders (CEOs, entrepreneurs, doctors, lawyers, pretty much the gamut of perspectives) would read and discuss a new book every month. Looking back, The Second Mountain was the moment the book club transformed. So many CEOs start out their career trying to get somewhere (rich, famous, successful), only to realize upon getting there that it was an incomplete goal all along. This newsletter’s namesake, The Second Mountain explores the evolution of meaning-making in the life of a leader, from the Self-Oriented-Success of the first mountain to the Community-Oriented-Purpose of the second. A critical read for accomplished leaders looking to dive deeper into purpose.

The Meaning Revolution

The last decade has revolutionized the art and discipline of building and getting the most out of teams. In that time we’ve moved from a wholesale expectation that a complex stew of carrots and sticks would drive behaviors to a realization that people yearn to dedicate their lives to something bigger than themselves, what author Fred Kofman calls “immortality projects,” if only their work was worthy of that commitment. In The Meaning Revolution, Kofman, the former head of culture at LinkedIn, provides a cutting edge analysis of the power of purpose in a modern organization, as well as tools to find the reader’s own purpose and integrate it throughout their organization, perfect for leaders of second-stage companies looking to bust through a ceiling.

The Artist’s Way

Most founders that I work with look back at the early stages of their company as a time of tremendous innovation, when they were free to take risks and innovate. But the constant demands of running a company have a way of beating the creativity out of founders if they’re not careful, which can turn even paradigm-shifting companies stagnant. Julia Cameron wrote The Artist’s Way to help stuck people rediscover their creative spark. For a leader this can be the key to unlocking previously inaccessible levels of growth, as founders are simply artists working at scale. This book, designed to be read and workshopped over 12-weeks, is perfect for leaders looking to introduce or expand their creativity and innovation.

The Advantage

The most useful “how to run a business” book I’ve read, Patrick Lencioni’s The Advantage lays out a blueprint for company operations that leaders can use immediately to transform their organizations (and their relationship to those organizations). In The Advantage, Lencioni distills the highlights from his other groundbreaking works (Four Obsessions of an Extraordinary Executive, Five Dysfunctions of a Team, etc) into a single volume that was foundational to how we rebuilt our corporate culture at VNN, aligning a 100-person team with only a few key structures. For entrepreneurs leading companies >20 people, this book is gold.


I’m looking for more business books that don’t suck. What other business books are worth reading the whole way through?

Coaching tool: How to “listen to unstick,” and help your people grow beyond their limitations

Leadership coaching is, to some extent, an art of listening for stuck places. Places in a person’s thinking where a belief or a false-equivalence is preventing them from seeing the true breadth of options available to them. When I find a stuck place when working with an entrepreneur — usually a belief that often has been very useful to them for much of their life but is now getting in the way of them getting what they want — I can bring that stuck place into our conversation. Simply bringing the belief into awareness, allowing the entrepreneur to see it as object rather than subject, is often enough to catalyze change.

Listening to unstick is an amazingly useful tool and skill for coaching, but can also be quite useful for conflict resolution, or for leaders trying to help their team transform their results.

This video from Cultivating Leadership is a pretty outstanding walkthrough of what listening to unstick (what they call “unlock”) is, and how to use it in your working life:

Why you really can’t be a prophet in your own land

I’d signed up 800 high schools in the first four years running my previous company, before my alma mater would take a meeting. This was my first time confronting the veracity of the saying: “you can’t be a prophet in your own land.” I’ve seen this dynamic at play in dozens of companies since.

It makes sense why this is the case. People have an understanding of the world in which you are a certain way — people at Grand Haven High School understood me as a young kid who spent a lot of time in the principal’s office — and in order for them to see you as different, greater, their understanding of the world must change. They must confront the fact that their assumptions about you were wrong.

In the world of tough sells, I imagine “you were wrong” is among the toughest.


Thank you for reading, entrepreneurs.

May you be happy, may you be healthy, may you be free from suffering.



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