Hopping over the Rabbit Hole

Chapter 3 Fear. Failure. Focus.: Early Lessons in Entrepreneurship

“Nothing is more frustrating to an individualist than to be mired in a modern group-led, massive, corporate organization.”

—Humphrey Neill

From a young age I knew I wanted to be an entrepreneur. Maybe I was inspired by my uncle’s motorcycle shop, where I spent countless afternoons getting a first-class education in rolling up your sleeves and building a business. Maybe it was because I didn’t like conforming to other people’s schedules, and owning a company seemed to offer some measure of freedom. Either way, as far back as I can remember, all I really wanted to do was run my own company.

My first entrepreneurial venture was a smashing success. I was 12 years old. After being introduced to the Long Island Newsday’s incentive-based delivery program by childhood friend Paul Montoya—who is now the president of Media Sales at CBS Television—I built up the largest newspaper route in my hometown of Port Washington on Long Island, New York. To me, it wasn’t really about selling newspapers and making money. Having extra cash in my pocket didn’t hurt, but it was more about being the best—developing a reputation in the neighborhood of a hardworking, smart, reliable kid who was going to provide great customer service. I hustled my butt off selling papers to the Jewish, Italian, and Irish ladies in my neighborhood. To grow my route, every Wednesday I would ask my manager for a batch of free papers and go door-to-door ...