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Speed Review: Dear Founder

Speed Review: Dear Founder

Speed Review: Dear Founder

Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business

by Maynard Webb

Maynard Webb has helped found, fund and grow dozens of successful companies. Webb shares his lessons with aspiring entrepreneurs – at any age and stage in their careers. Featuring more that 80 inspiring, informative and instructive letters, Dear Founder is a guide for navigating the realities, risks and rewards of being your own boss and founding the company of your dreams.


With over 26.8 million small businesses in the U.S., and 600,000 new entrepreneurs joining their ranks every year, the need for advice and guidance for those businesses as they struggle to survive and prosper is clear.

In his new book, Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business, Maynard Webb presents that guidance in a series of letters offering advice to managers and entrepreneurs at different stages of the business life cycle.

Webb is an investor in startups through the Webb Investment Network (WIN), which he founded. He started writing letters to the founders of the startups in which he invested, as a way of offering advice and guidance to a larger audience rather than talking to individuals. What started out as an internal document quickly became a self-published book, which then became a valued gift for friends and colleagues. Increasing demand for copies resulted in a traditionally published book for a much wider audience.

The Smartest Person You Know

Starting a business or being promoted into a leadership position within an organization can be challenging and stressful experiences. You definitely won’t have all the answers, and you will probably be conflicted at times. You’ll welcome advice but be reticent about revealing your lack of experience. Webb wrote this book for those precise moments and structured the content around the trajectory of a company’s life cycle.

The Life Cycle

With over eighty-five founders in the Webb Investment Network, many of them faced similar situations at the same stages of their business growth. The author took notice of this frequency and endeavored to codify his advice for logical availability and maximum impact.

Beginning with Getting Started and culminating with every leader’s earnest wish of achieving enough success to Leave a Legacy, Webb offers direct advice backed by real-life examples from his own career and those of his fellow investors.

As with any good coach, there are tough questions and tough love when needed. Being an entrepreneur is described as: “Like caring for a baby. You are excited about the idea but there are times when everything turns to poop.” The tough love follow-up: “Unlike a baby, you can’t hire a nanny to do the work for you.”

When the author doesn’t have personal experience of the situation to share, he’s not afraid to reach out to others within the WIN network for additional input, such as advice on what to do when your business gets sued: “Litigation is WAR,” but “cost control is critical.”

Part Coach, Part Counselor

Webb’s credibility in writing these letters is established by his extensive and illustrious business career. He has navigated many of these problems himself on more than one occasion and helped others to do so as he guided them in their business development. As a result, the advice is more consultative than prescriptive in approach.

For example, when offering guidance on what to do when you have to report bad news, the author cites an example when “one of the companies in the WIN portfolio missed its bookings target by around 40%.” The head of sales notified the board of the shortfall, earning Webb’s respect, but Webb made it clear that the news should have come from the CEO. That would have sent an important message that the entire company was working to fix the problem.

Dear Founder is a true “phone a friend” business book. No matter which stage of the business life cycle your organization may be in, the advice in this book will serve as: “your mentor and role model, coach and counselor, confidant and friend.” You would be wise to keep it close by and turn to it with every question, fear and uncertainty you will face as your business grows.

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