Chariot Solutions CEO Mike Rappaport ran a code-driven football pool in high school

Every entrepreneur has to start somewhere. In Lemonade Stand, we profile a local entrepreneur’s first venture or job. Tell us about yours.

Like a lot of tech entrepreneurs, Chariot Solutions CEO Mike Rappaport had an entry-level gig where he learned how to code.

In 1985, Rappaport took a “gopher” job at ATD American, a manufacturing and distribution center where his dad worked. He ran errands and other minor tasks until an opportunity arose to develop software: By the end of the summer he had created a sales system that the company would be using for several years.

“The opportunity to use technology for business was what I fell in love with at ATD,” said Rappaport, who worked at the company for 16 years. “I was completely hooked on the idea of connecting the two in order to create something useful.”

But then after entering — and losing — one too many football pools, Mike decided to put his programming skills to work. He created a system that would receive player information and update the winners of each game as they finished. 

Some high school and college friends helped him pedal the code-fueled football pool across campuses for commissions. Though the one-off enterprise was fun and profitable, by 1992 Rappaport settled down with his first official company: a software subsidiary of ATD called Skylight Systems, which ultimately led him to create Chariot Solutions in 2002.

Rappaport has long since put his pool-running days behind him. “These days it’s more like fantasy football,” he said. “I’ve been in my current league for over 20 years!”