My 25-Year Journey as an Entrepreneur

Thoughts on Excellence Free E-Newsletter Series
Volume 20, Issue No. 20b
January 15, 2023

By Dan Coughlin


Remember Why You Became an Entrepreneur in the First Place

On January 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 of 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 and teamwork and 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 in order 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 January 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

In order 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 in order to leap. Ah, that wasn’t going to happen. I barely saved any money from my teacher’s paycheck. What I learned was what a person really needs is enough self-confidence to leap and hang in there as an entrepreneur for at least two years.

And 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 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 of 1997 if she would be okay 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 $4000 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 January 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 38-year career as an engineer, and I went on to a career as a college soccer coach, high school math teacher, executive coach, seminar leader, and facilitator/guide on a variety of business topics.

I began to teach my seminars, The Self Concept Course and The Adventure of Life, to high school students in the summers of 1991 and 1992. By 1992 I started teaching those classes to adults. And then the fateful decision to not be hired as a high school head soccer coach came in 1993. And then the five loooong years of preparing to step out on my own. I left a tenured teaching position at a great high school to start a business, and I didn’t even have a business card. As Steve Jobs said in his famous graduation speech at Stanford University, “You can’t connect the dots looking forward; you can only connect them looking backward.” The key is to maintain the purpose and the passion to do whatever it takes to be able to launch into and sustain your own business.

Find a Great Mentor

As I was leaving high school teaching and starting on my own, one smart move I made was to ask a lot of people a lot of questions and to write down every one of their answers. I was an absolute sponge and picked up ideas every day.

Perhaps the most important person that I asked questions of was Alan Weiss, who is the absolute world-wide guru on starting and thriving in your own independent consulting business. I saw him speak two days after I left teaching on January 17, 1998. He gave incredibly valuable and practical advice. Then in August of 1999 I sat at a Roundtable Discussion with Alan as the leader of the table. He gave even more great advice, and so I hired him to be my mentor. He was mentor until December of 2007. His advice on a million small and large topics was absolutely incredibly helpful to me.

Search for Great Clients

There are clients and then there are clients. I took on anybody who was willing to work with me. I once coached a person who worked in a jewelry store. My entire payment was that my mom got to pick out a bracelet that she really liked.

However, the biggest break of all was during my last few years as a high school teacher. On December 1st, 1995, I self-published a book called Inside Out: A Catalyst for Conscious Living. A student in my high school class had a father who was the Regional Vice-President of McDonald’s in St. Louis. He bought my book, and gave it to his Director of Operations, Lee Renz.

On December 1, 1996 I got a call from Lee and he asked me to meet for breakfast. Lee ended up hiring me to do four workshops for his team at McDonald’s in 1997. However, Lee was promoted to Oak Brook, the world headquarters for McDonald’s, right before my first workshop so he didn’t attend any of them. I did the four workshops in St. Louis, and then I reached out to Lee to say thank you. I offered to come to Chicago to meet Lee in person to go over the material as a way of saying thank you to him. That was on August 6, 1997.

At the end of our conversation, Lee said, “Will you be my executive coach?”

I said, “Of course, I will be happy to be your executive coach, but what’s an executive coach?”

Sometimes it is better to be lucky than smart, and in that case I was incredibly lucky. From that day to this day I have provided over 5,000 one-on-one Executive Coaching sessions for over 300 executives. I had found the medium that allowed my talents and passions to be of their most value to other people.

Try Many, Many Ideas to See What Works and What Doesn’t Work

As an entrepreneur, I encourage you to try lots of ideas to add value to your customers and potential customers. Then be honest with yourself in identifying which ones work for you that you enjoy doing and which ones don’t work for you. It’s not a failure to identify what is not working for you. It just allows you to spend more of your time, talent, and energy on the things that work for you. Here are a dozen things I tried over the past 25 years. I’ve broken them down into the six that did not work well for me, and the six that did work well for me.

Did Not Work Well

Writing Books – I LOVE to read good non-fiction books, and I thought I could naturally write good non-fiction books. I wrote six books and combined they sold very, very few copies. I’ve learned to love to read books and not write them.

Keynote Speaking – Several people told me they thought I would be a great keynote speaker. However, my heart was never really in it. I don’t believe that people learn best by listening to one person talk for 45 minutes to an hour. So I invariably turned my keynote speeches into interactive, discussion-oriented learning, but that’s not what people are looking for in a keynote speech.

Dealing with Macho Know-It-Alls – This one represents the worst moments of my life as an entrepreneur. I define an arrogant executive as a person who thinks he or she has all the answers and has nothing left to learn from anyone else. I suffered through about five of these relationships before telling myself that I will absolutely, positively never endure one of those again. Now I just look the person in the eye and say, “I don’t think this is going to work out. Good luck with your work.” And a rude arrogant person is even worse to me than an arrogant person. I have one simple rule now when I meet a potential new customer: I don’t work with jerks.

Writing Articles for Major Magazines – This would have been so helpful in getting my name out to a lot of people, but I never had any success at it. At some point, I decided to pour my efforts into other activities.

Large Public Seminars – For a few months early on I did a lot of public seminars for the American Management Association. I quickly found out that while that is great work for some people, it is not great for me. I like teaching my own material, not someone else’s.

Traveling to Four Cities in Five Days – This one is connected to the last one. In doing public seminars, I was traveling to four cities in five days. After a few months of that, I realized that it was not the reason I left high school teaching. I left to be able to offer my own ideas toward helping other people to achieve whatever they wanted to achieve. I admire people who can travel non-stop and teach those public seminars, but it was not the method for me to add the most value to the people I wanted to work with.

Did Work Well

Executive Coaching – This was the perfect match for me. I like listening to people tell me about their dreams, goals, obstacles, challenges, and concerns. I like working with them as thinking partners in figuring out how to achieve what they want to achieve. This was the ultimate sweet spot for all that I had learned and was able to deliver to other people. I’ve enjoyed every second of being an Executive Coach for so many wonderful individuals.

Writing 2-3 Page Feedback Letters – Some people think that writing a 2-3 page feedback letter after every single Executive Coaching session must be exhausting grunt work. I see it differently. I think of it as being an artist who is given a blank canvass on which to paint a unique and beautiful painting for an audience of one person. I love the challenge of writing those letters each time. In the past 25 years I’ve written more than 10,000 pages of feedback letters to my clients, and I still love doing it.

Half-Day and Full-Day Seminars – These seminars are so tremendously fun for me to do. I love teaching an idea, asking people to reflect, getting them into one-on-one discussions, and then gathering ideas from the large group. It’s like conducting a fast-moving jazz session with ideas flowing rapidly. It’s an amazing way for everyone to learn from each other. And I learn the most each time.

Facilitating Important Group Discussions

I facilitated so many meetings at McDonald’s that one person called me, “Dan, Dan, the Facilitator Man.” I love facilitating. I do my best to clarify the desired outcome, to include every person’s perspective in the room, to summarize clearly, and to keep the group on track. I remember a particularly enjoyable three-day meeting at Emerson as we worked on the idea of a Digital Transformation for Emerson. And another time I facilitated a four-hour session on Strengthening the Culture at Traffix that led to a wide variety of powerful ideas.

Group Coaching Programs

This idea came during the Pandemic. I love to teach and I love facilitating small group discussions. So the idea came to me to invite people from anywhere in the world to join a six-month Leadership Development Group Coaching Program where we would have no more than 5 people at a time in a zoom room. I sent them the Pre-Work Thinking Exercises two weeks before each session, and we had a total of 10 sessions. The conversations were magnificent.

Working with Open-Minded Learners Who Want to Improve

At the heart of my successful and enjoyable work are the types of people I work with. This is not based on age, gender, race, title, experience, or any other label. The key is that the participants are serious-minded and open to learning new ideas and are willing to try to put insights into action. The vast, vast majority of the people I’ve worked with over the past 25 years have had this attitude, and they have made this work tremendously fulfilling and enjoyable.

Think about your work and the things you have tried. What works well for you, and what does not work well for you? Be okay with letting go of lots of things in order to focus on the few things that you can be really extraordinary at doing.

Deal with Forces Outside of Your Control

No matter how hard you work and no matter how much success you have at any one moment, there will always be forces outside of your control that are going to challenge your will as an entrepreneur. Here are five that I dealt with.

The Dot Com Bubble Crash: March 2000

In the first 26 months that I was in my own business, the world was obsessed with Dot-Com Companies. I mean literally obsessed. Twenty-somethings were becoming instant multi-millionaires with literally just an idea for a company. Then in March 2000 reality set in, and the Dot-Com Bubble burst. Enormous amounts of money were lost. It was chaos. Some of my clients just went away, but something far worse was to come 19 months later.

September 11, 2001

On September 10, 2001, I took a flight from Washington, DC to Chicago, and then another from Chicago to St. Louis, which is where I live. The reason I remember that was because there was no security gate to be checked through. I walked right up to my gate. And then on the morning of September 11th I was sitting in a conference room in St. Louis when the person who was running the meeting walked out for a few minutes. She came back and said, “Two planes have flown into the World Trade Center. The announcer thinks we are under a terrorist attack. Everyone please go home right now.”

Immediately the world changed.

That day 3,000 people died in the U.S. It was absolutely horrific. My wife, Barb, and I had a two-year-old daughter, Sarah, and a five-month-old son, Ben. We kept the news off. We didn’t want them to see the images on tv.

All of my clients instantly shut down their work with me. It all happened within the same week. No additional income that year, and none to start the next year. And that was the very least of what I was worried about. We as a country had no idea when the next attack was going to happen. Completely out of our control. It seems like just yesterday. All we cared about was that our children stayed safe.

Eventually in late 2001 I poured a great deal of time and money into marketing to find new clients, but it produced not even one phone call.

Eye Surgeries: 2007 – 2008

In the back of our eyes we all have a film. At some point that film drops down. For some unlucky people that film catches on their retina, and pulls the retina until it becomes partially detached. They didn’t do anything wrong. It is just the luck of the draw. This is all what my ophthalmologist explained to me.

I was doubly unlucky on this one. I had a partially detached retina in my right eye in 2007 and a partially detached retina in my left eye in 2008. Wow, those were pretty serious setbacks. Fortunately, my doctor was able to reattach both retinas. Unfortunately that eventually led to cataract surgery in both eyes. But none of this was nearly as bad as to what would happen next.

The Great Recession of 2008 – 2010

In October 2008 the housing market along with the stock market suddenly imploded. The Dow Jones went from about 14,000 in 2007 to around 6,600 in 2009, or at least that’s what I remember. In 2009 I made less than 10% of what I had made in 2006. It was not until late 2010 that clients started really coming back to work with me. It was the lowest point of my 25 years in business. I lost all the money I had saved during the previous 10 years.

The Pandemic: March 2020 – August 2021

And even as bad as The Great Recession had been, nothing prepared us for the devastating impact of the Covid-19 Pandemic. Millions of people died around the world. People literally could not leave their house for weeks at a time. To go grocery shopping a person had to wear a mask every minute, and toilet paper was on a tremendously tight ration. I couldn’t even go see my 91-year-old mom at her senior living apartments because I was not her primary caregiver.

However, as with all of the other unexpected events, the Pandemic led to new ways of adding value to people. I cleaned out my closet, found The Adventure of Life Course that I hadn’t taught in over 25 years, and created my Leadership Development and Executive Development Group Coaching Programs. They have turned out to be one of my very favorite ways of work with people to develop as leaders and as executives.

Of course, the same things I went through in all of these situations also affected hundreds of thousands of other businesses in very negative ways. No business fully knows what is just around the bend ahead. Not only is change constant, but even the changes change.

What I’ve learned is to control what you can control, don’t worry about what you can’t control, and do the best you can with what you have at this moment. I love this quote: all you can do is all you can do, but all you can do is enough. Successful entrepreneurs keep forging new paths and new approaches in order to add value to customers.


Look back on your life and extract from your own experiences insights that can help you as an entrepreneur.

I used to be a goalie in high school and college soccer. In a soccer game there is no script. You don’t know what will happen from one moment to the next. I was never a very good goalie, but it was a great preparation for being an entrepreneur. You prepare as well as you can, and then you learn from every moment of every situation that you find yourself in. Even though engineering was never going to be my life’s work, I learned from my engineering classes the importance of taking what you are given and working with it to find a solution to the next problem you are facing. That’s essentially what entrepreneurs do every day. Two things that appear to have nothing to do with running a business, playing soccer and engineering classes, turned out to be very helpful for me.

Being an entrepreneur has been the wild adventure of my lifetime.

I’ve spoken in Budapest and learned to never let a stranger offer to buy me a dinner. Fortunately, I learned that before people started offering. I gave a seminar in New York City a few weeks after September 11th, 2001, and everyone was super friendly and helpful as I walked around looking for the hotel where the meeting was at. I’ve had a chance to teach and facilitate discussions on leadership and communication and management  and culture and strategy and branding and teamwork for Anheuser-Busch, McDonald’s, Coca-Cola, Marriott, Traffix, RE/MAX, Toyota, Shell, GSD&M Idea City, Stryker, Emerson, and more than 200 other organizations.

None of that would have ever happened if I had not stepped into the wonderland of entrepreneurship.

Recently I watched the film, The Fabelmans, which is about Steven Spielberg’s life from the age of 5 to the age of 19. It spurred me to realize that our earliest passions can find their place in our life’s work. As a nine-year-old kid, I had a dream of creating something like a YMCA where people could come together and learn and then take what they learned and use it in the real world. In essence, that’s what I’ve tried to do for my clients on an individual and group basis for the past 25 years.

What is your story?

How have you used your passions before you graduated from high school as an adult? Trust me, it is never too late to allow those passions to course through your veins at work every day.


Republishing Articles

My newsletters, Thoughts on Excellence, have been republished in approximately 40 trade magazines, on-line publications, and internal publications for businesses, universities, and not-for-profit organizations over the past 20+ years. If you would like to republish all or part of my monthly articles, please send me an e-mail at with the name of the article you want in the subject heading. I will send you the article in a word document.

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