15 Bedtime Stories That Keep Entrepreneurs Awake at Night: Book Review


“I remember sitting with my head held in my hands a number of years ago, unsure if my fledgling business was going to survive,”
writes David Ingram at the beginning of 15 Bedtime Stories That Keep Entrepreneurs Awake at Night. “…I was petrified by the thought of failing–both personally and professionally–and losing everything I had worked so hard to build over the years. I lost a lot of sleep.”

Ingram, the founder/CEO of VA-based executive search and IT staffing firm Capital TechSearch, probably sleeps better now. The company’s revenues increased 63% in 2008, earning it a place on the Inc. 5000 list of fastest-growing private companies—the second time the company had been honored.

Yet this successful entrepreneur hasn’t taken his learning curve for granted. “When I was in such a bad spot several years ago, I wish that I had a book like this one to reassure me and help me stave off insomnia.”

He didn’t have the right book, because the market didn’t offer him one. So Ingram proceeded to do what entrepreneurs do best: He created the product. The book, released in late September 2009, presents fifteen real-life business challenges, many from Ingram’s own experience. He covers the story, implications, and resolution of each challenge in every chapter of the book. At the end of each chapter, he presents readers with a short list of questions to help them work out similar challenges in their own companies.

Essentially an advice book, 15 Bedtime Stories covers important lessons that every entrepreneur growing a business from a startup to a platform (self-sustaining) organization should know. Each chapter presents a real-life business challenge, from cash flow to ethics. The human resources-related chapters were especially strong. This is not surprising, given Ingram’s industry focus on people.

One of the book’s most endearing qualities is its frankness. Ingram isn’t afraid to address the thorny stuff. One chapter recounts Ingram’s friend John’s experience of choosing to implement company health benefits after heavy deliberation. Soon afterward, John hired an employee who was diagnosed with cancer the same day the company brought him on. Another chapter tells the story of how a company’s top sales performer brought the rest of the team down, confronting the CEO with a difficult firing decision.

Ingram doesn’t gloss over things, but he doesn’t discourage you, either. In fact, he encourages you to learn from his mistakes rather than making those same mistakes yourself. His detailed descriptions and resolutions of business issues make the book a valuable reference source. Ingram could easily compile a longer book of lessons, for entrepreneurs to keep around as a desk reference.

If you’re curious about entrepreneurship, in the midst of it, and or just looking to improve your general business-running skills, 15 Stories is for you. Even seasoned vets can learn something from this fun and valuable book. Business Pundit recommends it.

Written by Drea Knufken

Drea Knufken

Currently, I create and execute content- and PR strategies for clients, including thought leadership and messaging. I also ghostwrite and produce press releases, white papers, case studies and other collateral.