My 25-Year Journey as an Entrepreneur
On Jan. 15, 1998, I woke up realizing that my only paycheck for the rest of my life would come from my own customers. That was certainly a powerful motivation every single day. It meant I had to create something of value that other people would be willing to pay for, and I had to keep finding those people. That is the daily challenge of entrepreneurship.
However, I’ m getting ahead of myself …
The Real Beginning was April 23, 1993.
In March 1993, I was the varsity assistant soccer coach and a math teacher at St. Louis University High. I loved and still love teaching. I loved interacting with the students. I just didn’ t love math. I assumed that when Ebbie Dunn, the head soccer coach for 38 years, retired that I would become the head coach. I had so many ideas about how I was going to incorporate my thoughts on leadership, teamwork, goalsetting and perseverance into my coaching of those high school students. Ebbie did retire from coaching in April of 1993, but I had assumed wrong. I did not get that job.
And that was the moment that I decided I would never put my career in the hands of one person, namely a boss, again. The other reason I decided to leave high school teaching was because I wanted to teach courses on leadership and teamwork and goalsetting, but the principal and the president of the school did not share that vision with me either. They wanted me to be a niche-filler, namely to fill the niche of teaching freshmen, sophomore and junior math.
It took me almost five years to leave teaching math to teach what I wanted to teach. I was afraid to take the leap into the unknown. I had a check coming to me every two weeks. Looking back now, I realize that from a financial standpoint I was essentially jumping out of a first-floor window. It would have been almost impossible to make less than I was making as a teacher. However, at the time it seemed like I was jumping into the Grand Canyon. On Jan. 15, 1998, at 35 years old, I walked out of my high school math classroom for the last time and walked into the rest of my career.
Find the Motivation to Jump.
To leap into the world of entrepreneurship, you need to be extremely well prepared mentally. People told me I needed a year of financial savings in the bank to leap. Ah, that wasn’ t going to happen. I barely saved any money from my teacher’ s paycheck. What I learned was that what a person really needs is enough self-confidence to leap and hang in there as an entrepreneur for at least two years.
So during my last few years as a teacher, I fed my mind with as many reassuring books, tapes and conversations as I could find. I read over and over and over Og Mandino’ s book,“ The Greatest Miracle in the World.” I listened to Zig Ziglar’ s by Dan Coughlin tape,“ Goals,” over and over and over. And I supplemented those two resources with as many inspiring biographies and autobiographies as I could devour. I attended meetings of the National Speakers Association and found people who were doing what I wanted to in terms of giving seminars and working with other people in small groups and in one-on-one situations.
And I asked my wife, Barb, in August 1997 if she would be OK with me leaving my job as a high school teacher and starting my own business. She looked me right in the eye and said,“ Of course. You will do great.” Wow, I needed the voice of support from her at that moment, and she delivered!
In 1996 and 1997, I gave a total of 75 presentations and got paid very little for them. I spoke to any group that would listen to me, including senior citizen homes, high school assemblies, Optimist Clubs, Kiwanis Clubs and a few businesses. I made a total of $ 4,000 in 1996 and $ 12,000 in 1997 as a seminar leader. That’ s $ 16,000 total over two years for 75 presentations. That’ s not exactly a year’ s worth of savings, now is it? And with that I jumped into the world of entrepreneurship on Jan. 15, 1998.
Clarify the Purpose and Fuel It with Passion.
My first day as an entrepreneur can really be traced back to the fall of 1984. I was a senior in college majoring in Mechanical Engineering at Notre Dame. I was the engineering student who made the top 90 % possible. I didn’ t just dislike engineering. I hated it, and I was terrible at it.
In a notebook, which I still have, I wrote down that the purpose of my career was going to be to help other people achieve whatever they wanted to achieve. That’ s my gift, my talent. When I took Thermodynamics, I think I actually understood a total of one chapter. And it was so exciting for me to help a friend of mine understand that chapter and to do well on that test. He went on to a
2025 Issue 3 | GearedUp
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