Making the Entrepreneurial Jump


I am often asked, “Why did you decide to start your own business?”  After all, at the time I was the head of the Hamilton County Virtual School, the online program of the fourth largest district in Tennessee.  I had ten years in and was making a good salary.  I was even offered a $20,000 raise and a promotion if I would stay with the district.  So why jump off the entrepreneurial cliff? 

The decision was surprisingly easy to make.  Here’s how it went:  In December of 2011, I dropped into to see my superintendent with an idea.  I had noticed revenues for the district virtual school shrinking and felt like savings could be realized by creating a service to which the district could then outsource its program.  I asked my superintendent if he would look at an idea like this if I put together a proposal, and he said he would.  I believe he was nonetheless surprised when the following February, I presented him with an outline for what became Village Virtual.  The district could call on the expertise of someone with years of successful experience both with virtual school and with all the schools in the district but bear the expense of only what courses were actually utilized by students in the district.  From my perspective, what was not to love about this?  With a district funding of about $8000 per student and virtual school taking only about $3000 of that, why wouldn’t a district want to outsource such a program?

Initially agreeing to present my proposal to the board, district administrators ultimately opted out of the idea of outsourcing the virtual school, making instead what I am sure seemed like a sure-fire counter offer – a $20,000 per year raise and a promotion. 

There was only one catch – I had already seen Village Virtual fully formed and functioning in my entrepreneurial imagination.  I had a business plan. I had an office space picked out.  Business cards were on the way.  As I walked down the hall toward my bedroom after the call with my supervisor, I was weighing out the options in my head.  Retirement plan, health insurance, safety and security of a district job versus all those unknowns . . . .  My youngest son (still in school himself pursuing a music degree) was standing at the end of the hall.   I asked him, “Son, what do you think I should I do?  We have a good life right now.  If I start this business, we may have to eat beans for quite a while.”  Without hesitation, he said, “Mom, I think you should go for it.” 

I knew in that instant that I could not tell him to pursue his dreams if I were too afraid to follow my own.  I turned in my resignation and opened Village Virtual in the fall of 2012.  In the more than five years that we have been in business, there have been so many times when a student or a parent or a school leader has reached out to say, “Thanks for being there.”  We have helped students in trouble, students with health conditions, students who needed scheduling flexibility, athletes who needed to train, districts who needed access to foreign language options or a way to serve homeschoolers, families who were at the end of their rope and frightened that they had run out of options. Tons of 10-hour days, yes.  Worry and stress over how all the bills would get paid and all the work get done, yes.  Pulling my hair out over QuickBooks, yes.  But there hasn’t been a single year in which we were not profitable, and both of my sons are entrepreneurs – one an artist and one a musician.  Both veraciously pursue their dreams even when it’s hard, even when it means hours and hours on the road or all day in the scalding sun of a community festival or market.  Both believe uncompromisingly in their dreams and dig in and work harder when things don’t pan out the way they thought they would.  Both are dedicated to their crafts.  No one has to nag them to practice or create.  It pours out of them like honey out of a jar.  This is what work looks like when it is “love made visible” (The Prophet by Kahlil Gibran).  I hope my legacy not only to my own children, but to all the young people I touch, resonates with that same message my son gave me that day more than five years ago -- Go for it!

Village Virtual CEO Debi Crabtree with daughter-in-law, Kelsey Stevenson, son, Ryan, and son. Rob.

Village Virtual CEO Debi Crabtree with daughter-in-law, Kelsey Stevenson, son, Ryan, and son. Rob.