Book

Chicago Shoeshine Boy

About the BooK

In 1955, a young boy in Chicago’s South Side began his entrepreneurial journey selling trash from the alley on 71st Street. That boy was Mike Benner, and little did he know that those small, odd jobs—whether shining shoes, delivering newspapers, or working at the circus—were shaping him into the self-made businessman he would become.

From being a bean picker, a hired man, and a door-to-door salesman, Mike learned the value of hard work, resilience, and an unbreakable spirit. His relentless pursuit of success took him through multiple industries—from the paper routes of Southtown Economist to corporate leadership at Federal Signal and Stewart Warner Instrument Corporation.

Through failures, setbacks, and triumphs, Mike Benner’s story is a testament to how determination, adaptability, and perseverance can turn a shoeshine boy into a successful businessman, mentor, and leader.

Chicago Shoeshine Boy is more than a memoir—it’s a blueprint for financial success, overcoming obstacles, and seizing every opportunity life throws at you. Whether you’re looking for inspiration, a fresh perspective on the American Dream, or a step-by-step account of turning zero into wealth, this book will leave you motivated, empowered, and ready to take action.

WHAT ADVICE WOULD YOU GIVE

A few years ago, I began posting “Thoughts at 3:00am.” It came about as the result of my erratic sleep pattern. I would get some philosophical thoughts in the middle of the night. I began sharing them on Facebook. Over a period of about 5 months, I posted one thought each day. Among them was “Sometimes the best advice is no advice.” While I still believe that, but I’m not opposed to sharing my thoughts with whomever might be interested. Other 3:00am Thoughts that guide me include:

  1. “You can compromise on tactics but not principles.”
  2. “There’s a difference between listening and waiting to talk.”
  3. “Success is often built by picking up the ruins of failure.”
  4. How you spend your discretionary time determines your priorities. It’s not sufficient to claim a priority. You must commit to it.

So my advice:

  1. Be honest: believe in what you’re doing,
  2. Listen to those who have accomplished something. If you have an idea that you believe has merit, don’t ask a person who lives in a trailer park for his opinion. Set your sights high and don’t give up.
  3. Be prepared to sacrifice a large portion of recreational time to devote to the pursuit of your goals.
  4. When you fall, learn from it and get up more resolute from the experience.

Finally, success is measured not by what you accumulate but on how many people you were able to positively impact.