How I lost $75,000

What’s Happening?

Earlier this week I sat down with “The Guys Who Do Stuff”  podcasters Joe Woolworth & Josh Manning.  They put on a great show with some super interesting guests. You can find their podcast online or on your preferred podcast app.


How did I loose $75,000?

It’s all because I didn’t know I could sell my business when I was ready to move on. 

Let me give you some back story.

In 2001 I moved to Italy and very quickly started a language school.


In the beginning, my “language school” was just me. It really wasn’t much of a school at all but my vision was to create a true language school.  Why a language school? Well, this came about because of a single contract a friend asked me to help with in Brazil, but that is a story for another time.

Any way, after acquiring some “English as a Second Language” student books and teacher manuals. It was time for marketing. 

I printed out some flyers on my home printer and hung then up around town. The very basic flyer read (as well as I can remember): 

If you want to learn English call Joe

People started calling me and I started getting students. Emboldened, I created and printed a tri-fold, which I took to companies and schools in the area.

Within a few months I had more students than I could handle and eventually I had seven teachers working in public schools,private schools, businesses, private groups, and community educational projects. The teachers were working part-time between 4 and 20 hours a week and I continued with teaching also.

Things were going well, I enjoyed teaching, made good money, had two months off in the summer and long winter vacations. But things change and life can throw you some curve balls once in a while.

Around 2003 I started thinking I would like to move back to the US. It would be tough to give up the school, but I had good people working for me and I was sure they would do well, as would the students.

What I didn’t realize was that I had a business that with some planning and strategic organization was worth money.  I never even considered that I could sell the business. 

My thinking was: I just gathered some people interested in learning English and some teachers to help them learn. I was just the guy who coordinated everything.

I now know differently.

There was great value in what I had organized:

  • • Year long contracts that had been renewed for at least a couple years running. Think subscription model.
  • • A process for obtaining new students and new contracts with businesses.
  • • A process for training and retaining teachers. 
  • • Brand recognition in the region
  • • Low expenses and high margins


I didn’t know it at the time but that was something of value.  So in 2004 I gave to the teachers their respective groups and divided up the groups I had kept and closed the school. 

Only years later did it hit me that I had a valuable business that I could have sold for $75,000 or more. Granted, not a lot of money, but a lot more than “$0”.

If I had known that selling that business was possible it would not have taken much time, just a change in priorities, to really build the value and attractiveness to a buyer. As I know today there are business value drivers that all businesses can work on. A business owner can get the most value for their business and greatly enhance the chances of the new owner’s success by having the right plan.

Though a large part of a business’s valuation is based on bottom line profit, there are more variables to consider.  Most of which center around the degree of risk to future earnings. To learn more about some of these value drivers see “3 ways to increase the value of your business”.

Avoid the mistake I made

  • Recognize that you have something of value even if you don’t think you do at this point
  • Plan early
  • Work on the Drivers of Business Value
  • Contact Eagle Business Services for a free 30 minute consultation


I’m on a mission to help business owners to not make the same mistake that I made. If you are a business owner thinking about selling your business in the next 1-10 years, or if you want a business that is more profitable, enjoyable and offers more options and freedom schedule a free conversation to learn how you can create more value in your business.