Entrepreneurship Interview Series: What You Really Want Is Options
Entrepreneurship Interview Series: What You Really Want Is Options
02 Oct

Entrepreneurship Interview Series: What You Really Want Is Options

Experience is the best teacher. In this Entrepreneurship Interview Series, we’re going to share stories from your peers about their lessons learned as successful entrepreneurs.

Here we speak with Jon Aleckson, Ph.D., the CEO of Web Courseworks, an educational technologies company.

In this interview, you’ll learn about Jon’s crossroads moment and the importance of making sure that in the end, you’ll have more than you had in the beginning. When all is said and done, what you really want is options.

We ask him three questions about his entrepreneurship story and what people can learn from it.

Triumph Wealth: If you could give the “you of 20 years ago” one piece of entrepreneurship advice, what would it be?

Aleckson: When you are trying to establish a company, the biggest thing that you need to do as an entrepreneur is to build your next main product. My job as the CEO is to reinvent the future before it’s too late.

So in my case, being involved in the large category of educational technology, innovation has played a major role. When I first started, I was shooting 16-millimeter film and working with Kodachrome slides. And then technology changed in the mid-70s, and we had tape recorders and video cameras that were portable. So we moved in that direction. Those companies that stuck with the old technology were at a disadvantage.

We built a company around these digital technologies in the 80s and eventually built a studio with all the equipment. There were probably five video companies in town. However, within three years, we were looking at the next technology. By the mid-90s, we were looking at the internet as a way to build the business.

For me, it was easy because I just followed the technology. But for some entrepreneurs, it’s not as simple. They have to brainstorm about what they’re going to get into whether it is new products or services. For me, I stayed within educational technology and just changed the direction we were going in.

The same thing goes for new markets. You have to be testing new markets even while you’re doing well in an existing market. You never know when there will be new competition or when someone else will build a better mousetrap. We’re 35 employees, so it’s easier for us to be nimble.

Triumph Wealth: What was the biggest “crossroads moment” in terms of your success as an entrepreneur? Would you have done it differently if you could relive that moment over again?

Aleckson: The crossroads for me was going back to school and learning the importance of focus – focusing on a niche market instead of being everything to everyone.

When we moved into the internet and started providing online learning, I decided that I needed to go back to school. I went back and got a Masters and Ph.D., and took some courses in the business school. That revitalization of myself helped to shape the company’s next stage because at the university you are exposed to new concepts. I needed that knowledge to break out and service a national clientele.

Today, our clients are national associations that provide continuing education programs for their members, mostly located in Chicago or Washington, D.C.  One example is a medical society that needs to keep its members apprised of the most recent educational content. I learned about this market from a course I took in school.

It was a crossroads because it gave me the focus I needed to create a presence in this specific niche. When you start out, you are taking any business you can get. For example, I was doing TV commercials for one of my clients. They ask, and you just say, “I’ll do it!” This isn’t the best long-term strategy because you effectively stretch yourself and your team in all sorts of ways.

After this crossroads, I established myself as a national thought leader and established my company as a national player. Before this, I had been relying on local business, but I grew the footprint to include clients who were not in Madison, Wisconsin, where our company is based.

Triumph Wealth: Do you think ending your business will be as hard as entering (or starting) it?

Somebody told me that the best definition of success for an entrepreneur is that they have options. If you’ve taken care of yourself along the way, then you have options both personally and professionally.

As a business, when you start out, your only option is to get customers and maintain cash flow. Whether you admit it or not, in the beginning, you are always at the cliff – you’re struggling not to spend more than you bring in. If you haven’t taken care of yourself along the way, then you’re effectively in the same situation at the end, and it is as hard to leave as it is to start.

Personally, do you have enough choices where you can get what you need to be happy in your life? Entrepreneurs never really retire. The kind of person I am, I have to keep doing something.

The scariest thing for a business owner is recession because you have no control. The music stops with a recession, and in an instant, it could all be gone. I’ve had that happen four times, the most brutal being after 9/11 and the dot com bust. One day we’re rocking and rolling with 25 employees and a building, and the next day 75% of our contracts were canceled. Fortunately for me, I had a really good executive coach at the time to help me make good decisions during those recessions. It was a “do you want to be in business next week or not” kind of thing.

At this point, I have many options for how to exit my business: employee ownership, selling it to a third party or a successor, etc.  I knew how to take care of myself. I can’t tell you how many times I’ve told other entrepreneurs that when you have a good year, you’ve got to squirrel some cash away so that you have a nest egg. I took care of myself, so at this point, I have options.

What’s your entrepreneurship story? Contact us if you’d like to be interviewed as the next guest in our blog series.



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