As technology evolves, so do tech entrepreneurs — if they do so intentionally. Business owners are people, so keeping up with the times, the marketplace or the Joneses doesn’t occur automatically. It takes a conscious decision to stay in the game.
Entrepreneur Bill Dotson is on his third technology company. From TransDigital Solutions to WebMedley to Rocker, each business has stretched his risk tolerance, enhanced his business acumen and enabled him to solve more complicated digital challenges for clients.
Dotson worked for other people from ages 14 to 22, busing tables, bartending and working general labor for a construction crew. After graduating from the University of Kentucky with a degree in Asian studies and philosophy, he moved to Japan and taught English to children for almost a year before returning to Lexington to work for Mikrotec, Kentucky’s fi rst Internet service provider. Within 18 months he had gone from tech support to being in charge of sales, at which point he decided to go out on his own. He was 23.
“I have to give a shoutout to Drew Curtis,” Dotson said of the Fark.com founder who is currently making an independent run for governor of Kentucky. “We went to junior high and high school together. He had his own Internet company in Frankfort. He said, ‘Why don’t you make that money for yourself?’”
In 1997 Dotson did just that. St. Joseph Hospital was among his first clients. In 2005 he sold his company, TransDigital Solutions, to NetGain and worked for them for a year and a half.
“Once you work for yourself and start enjoying it, going to work for others is difficult,” Dotson said. It wasn’t very long before he had another opportunity to get back into ownership. He was consulting for WebMedley, a digital marketing and website hosting company, to make it a profitable venture for its owners. He did that, and in July 2008 made a purchase offer. It was rejected, but Dotson came back a month later with a better deal and a partner, and it was accepted.
His business partner was Chad Hobson, a WebMedley employee at the time.
“I watched a lot of my friends get laid off ,” Hobson said, “and realized that being employed is no more secure than rowing my own boat, so to speak.”
Dotson and Hobson operated WebMedley so the business could be sold at any time. The time was right in 2015. In the spring, Dotson contacted other technology companies, owned or operated by people he had known a long time, and all but one of which were interested in purchasing WebMedley. In May, Dotson and Hobson sold it to Lexington-based Fusioncorp Design as the company “we thought would take care of our clients really well,” according to Dotson.
He and Hobson took four clients and projects with them, including UK basketball coach John Calipari’s website. They had known it was time to sell and move on to something new, because complacency doesn’t sit well with either partner.