When I went to college I looked at the course catalog a few days before each term was supposed to start and went shopping. I picked classes based on the brochure.

Art history. Cool, slides for hours.
Behavior modification. Oh, what’s that!
Far eastern religion. Confusing Jewish childhood.
Science of sleep. Dark room with carpeting, duh.

Those are all legit, interesting topics. But they are miles away from any recommended path to being a business owner. No finance, business or even marketing classes.

My passion was for the theatre. So, I studied acting.
I wanted to understand the world. So, I studied sociology.

During college I worked at Mr. Steak as a cook. No matter the temperature you ordered your meat we had four turns to get the cross marks of the grill just right.

I was a camp counselor in the summer. The kids were only there for two weeks. They were inner city youngsters who were referred by social workers to attend camp as a respite from whatever family issues they were facing. For many this was the first they had slept away from home.

Another summer a buddy and I scraped the wax off the floors of a grade school floor. For weeks on end we leaned on one hand while the other hand moved single edge razor blades over hallways until the custodian declared it was clear enough he could apply fresh wax. 

The last summer of college I paid to be an intern at the Williamstown Theatre Festival. We had classes one day and then built sets the next. A brutal memory was one actor telling a class, “I work all over the country at well known professional regional theatres, and have for many years. But I have no home, no savings and own nothing.”

Those are my beginnings. A had passion. I had an interest in the arts, in the world. I was curious to learn everything.

Curiosity has turned me into a lifelong learner. That means always listening. I am forever asking questions. My family teases me they caught me one day watching a documentary on the history of loading docks.

When you agree to participate in a play you must research a time period. As an actor you often need to research the skills of a particular profession so you can portray the nuances accurately. You might need to learn the stereotypes of how a terminally ill individual treats their family. 

If you are like me, then you have a desire to contribute to a larger creative process , in team efforts and to do it even though you have much to learn before you are good at it.

That’s an Untrained Heart. 

There was no burning passion from a young age to own my own business. There was no breakthrough invention that caused me to launch a startup enterprise. I was in no way trained to become a businessman.

I did not have any credentials to start a business of my own. There was no indication based on my academic studies, summer jobs or even personal interests that would lead to a logical explanation for the path in life I followed.

Flash forward thirty years. I am at a casual party with many adults in their 50s and 60s. I was asked, “What do you do for a living?” 

“I’m a serial entrepreneur,” I replied.
“Oh, you mean like serial killer?”
“Yes, like that.”

Awkward pause for smiles and head bobs.

“I start companies. I own them. And then I shut them down or sell them. I guess you could say sometimes I kill them.” 

Serial business killer?

There are more smiles exchanged, a single nod of the head to acknowledge the moment. 

“What kind of companies?”

Curiosity simply can not be contained. 

I start to reply, intending to present a short version of my story. 

In my mind I picture a well structured, 30 second summary. I imagine the cool, provocative TV infomercial where the voice over sounds calm and confident. 

Instead, I launch into a full blown, first person documentary. The listener has made a calculated error in displaying an interest in what I am saying. 

“Oh, wow,” they say once or twice.

My ego is now ignited.

Yes! I accept your invitation to talk about myself for the foreseeable future!

My first love was for the performing arts. Acting was an activity that hooked me in eighth grade. My english teacher at the time took seriously a classroom production of Taming Of The Shrew. This Shakespeare tale is a delicious story about marital rules. The plot is a battle of the sexes and presents a fun romp. I’m sure my classmates and I understood almost none of that, but bless that teacher who insisted we memorize the script and perform it live for friends and family. 

She cast three girls to play the lead part of Kate. I imagine there were so many lines and so many girls to choose from she thought it only fair to split up the role. But for the part of Petruchio she cast only me. I was just that good, or there were simply no other boys in class up to the challenge. Either way, the experience hit me hard and the acting bug was planted. 

There was a line from the script that has stuck with me for over four decades now. 

“Thus have I politicly begun my reign. And ‘tis my hope to end successfully.”

In that statement Petruchio is declaring that he has created his plan. He knows how he is going to tame Kate. She is most difficult. She is a shrew of a woman. But he has grown to love her in his own way. He offers up the basics of his plan, the initial steps he will take to get her to change her behavior and be the kind of person he wants to be with. He sounds confident, for sure. But then he says he “hopes to have a successful outcome.” He admits that the plan comes with a possibility of failure. 

We know he is optimistic though because he uses the word hope. He believes in his plans. He knows there will be troublesome politics involved, which always come with uncertainty. And yet he launches into his campaign. He runs toward his reign with a targeted sense of positive expectations. 

I acted in plays every year of high school. Then, I went to Macalester in Minnesota for college, a liberal arts institution. I double majored in theatre and sociology. 

If that acting career does not work out there are thirties of jobs for sociologist to fall back on, right?

As I studied theatre history in college I noticed that what was happening any given period of history was reflective of the ideas and discoveries I was exposed to in the history of psychology, sociology, art and religion classes covering the same periods. I surely was not the first to notice that the theatre of a given period reflects the culture of the time, but the organic progression of my realizations fueled my passions. I wish this for every liberal arts student.

Once in the harsh world outside of school I realized that the life of an actor meant I would be literally applying for a job every day for the rest of my life. Actors are required to go on auditions all year long. 

They must perform an example of their work on the spot and instantly express talent. They are judged based on how they look. Good looking enough for the part? Ugly enough? Too tall? Not fat enough? Auditions are perhaps the most cruel form of job interview ever invented. Yes, there is that rare professional actor who reaches a level where work just comes to them without needing to audition any longer. But for 99% of the labor pool actors must apply with a headshot and resume in hand for every job. And they are temporary positions at best! 

After 50 auditions post college, the image of that lifestyle being permanent wore off quickly.

I became an entrepreneur. 

My first company was called LM Mystery Productions. We were a murder mystery production company. Perhaps not a big surprise my first born entrepreneurial project was of the theatre world. While working in the administration offices of Pegasus Players Theatre we were asked to produce a weekend event at a local Holiday Inn. This lead me to cofound a company with Floyd May that produced these improvisational events for private parties and corporations. We produced 100 events over a three year period. 

Another company was also inspired by the performing arts. While working at the Wisdom Bridge Theatre in the box office my colleague Emily Detmer asked me why Chicago had no theatrical bookstore, when New York and Los Angeles each had several. She was not from Chicago and as a native I was indeed perplexed. Six months later she and I opened Act I Bookstore. She worked there for three years before returning to school to become a professor. I worked there for five years, and owned the company for 16 years before selling it. 

A tangential company to the bookstore was called Chicago Plays. Much like the missing theatrical bookstore, there were a number of original works being produced in Chicago that were going unnoticed by the coastal literary agents and publishers. We aimed to represent these Chicago playwrights for production, publish their plays and help them gain national attention. 

My horizons expanded outside the performing arts when I took over an existing family business. My wife’s grandfather started a publication in 1930 that I purchased from my father in law. Made To Measure Magazine catered to the custom clothing and uniform industries. 

A spin off from that company was my first technology company started with Don Weismantel who worked at the magazine. xBx Channel Media was a web development company that built websites for apparel related manufacturing supply companies. We also went on to work for a number of years on web sites for Motorola, Tiger Electronics and dozens of others.

There was another company that emerged from a combination of the uniform magazine and the web development company. You can’t make this stuff up, right? With Al Baker and Lee Gorsky I founded UniformMarket, a technology company serving the uniform industry. We went on to build and manage close to 1,000 online stores for uniform companies and their customers who needed to order employee apparel. The company still operates today helping uniform retailers.

Skip ahead a few more companies to the Empathic Workplace and Improv Therapy Group. This ensemble operation is a recent company I helped start that resulted from meeting co-founders Angela Nino and Lisa Bany while taking improv classes at The Second City. We are helping corporate America learn to take an empathy first approach to the workplace, difficult conversations and investigations. We are also bringing applied improvisation to recovery treatment centers to teach life skills.  

The acting and improv classes nicely bookend my origins story as of this writing. 

My first love was the performing arts. And it appears the training I received in classrooms did prepare me for the life of an entrepreneur. 

The process of creating a theatrical production taught me exactly what it takes to start and run a business. Organizing and producing a live show takes planning, rehearsing, expecting trouble and maintaining hope.

Planning is an essential ingredient to start a business. The traditional methods of planning taught in business schools are well formed and certainly respected. I developed my own approach over time. I will continue to use the analogy of show business. 

Rehearsing a business means you will never get it right the first time, but with practice you may meet success. You will not have the cast and crew (your business team) ready in the beginning. You will not have your set built, lighting, sound and costumes (your retail space, showroom or offices). You will need to experiment with each scene many times, run the show again and again until you have the production in good enough shape to sell tickets (products and services, marketing messages, budgets). 

Expecting trouble is a given in show business. And so must you expect the same in business. Performers are human and they will make mistakes. Deadlines will be missed trying to organize the technical lighting, set designs and construction. Marketing the show may not go right and ticket sales fall short. Actors get sick or even quit the show because the director turned out to be an abusive leader. Anyone involved in creating theatre expects problems along the way

But… through all that, a date is set that you will perform the show. And in the world of producing a live performance, that date is fixed. Everyone knows the date and agrees to stick to it, no matter what it takes to get the show together in time.

Hope is the potion that makes a live performance magical. The entire process may feel poorly planned, unrehearsed and laden with trouble. But because the ensemble of cast, crew and producers have hope for a positive outcome the show comes together. The business of making the event happen does not stop a strong sense of optimism. Everyone wants to win. They all want a great show.

Indeed, the lessons I learned from that early exposure to Shakespeare has stuck with me.