The best books to ignite an audaciously creative entrepreneurial spirit

Robert J. Ringer is a genius at creating big impressions that impress prospects and win deals. In his book, he takes the reader through his early failures as a commercial real estate agent, when buyers routinely broke agreements and used their leverage to raid his commissions. His solution was to “intimidate” by overwhelmingly impressing buyers from the moment they met. As a result, buyers took a completely different impression of his importance—and never again asked to reduce his commissions. The psychological effect snowballed, leading to explosive growth of his business. A fascinating—and useful—study of how to harness human nature to prosper.

Early in my career, I found myself mentored by several of the world’s top cartoonists from Playboy and The New Yorker, including the amazing Gahan Wilson. His cartoons were works of wonder, with intricate cross-hatching, quirky details, and trademark macabre stylings. By sheer luck, I’d stumbled into a backstage pass with one of the greatest cartooning talents ever, so observing his process was a privilege. Humor is about revealing the truth with a twist, which is why I treasure this particular book by Gahan. It’s a collection of his work, but also a statement of entire purpose for all of cartooning—to capture truth.

Disruption is a celebrated essence in entrepreneurial circles. The disruptive technologies behind, say, Uber, that transformed society’s acceptance of ride-sharing, or Airbnb and short-term home rentals, changed the way we live, and created entirely new categories and great fortunes. In The Innovator’s Dilemma, Christensen exposes the full nature of disruptive technologies; where they come from, why they upend industry leaders, and what companies can do to recognize and harness significant new innovations. It is the owner’s manual for creating disruptive, entrepreneurial success.

Jay Conrad Levinson is one of my heroes. His first book, Guerrella Marketing, released when he was in his 50s, and went on to sell more copies than any other marketing book in history. A legendary creative genius from the ad world, he was teaching a class on impromptu, clever marketing tactics when his students (which included Steve Jobs and Larry Ellison) begged Jay to write the book that became the bestseller. Jay’s amazing book shows what’s possible when you apply lots of creativity and audacity to any marketing challenge. If you’ve read my earlier book, you’ll see plenty of Jay’s influence, starting with his foreword.

I enjoyed Alan Weiss’ book, Million Dollar Consulting, for its refreshingly hard-nosed look at dealing with clients. A business can’t exist without them, but contrary to conventional wisdom, the customer isn’t always right. They’re often difficult, stubborn, and think they know more about a given subject than the expert staring them in the face. Weiss’ book is a practical course on landing and working effectively with clients, especially getting paid what you’re worth. If your business model includes working with high-end clients, this book is a treasure map for growth.