Born in Chicago, Illinois, Stanley Jackson's middle name and nickname is Ossie after the successful and legendary African-American actor Ossie Davis, a favorite of his grandfather. His parents, like a lot of parents, wish their children would be successful. They know that despite some progress, things are not easy for African-Americans and ones who are at best lower-middle class. The eldest of six children, Ossie was the first one to go to College and finish a degree. There were some struggles, yes. But he proved himself again and again that he was a brilliant student and even got hired almost immediately after graduating. He had a successful career as a software developer for Microsoft until he decided to run his own software business. He then married his longtime girlfriend, Karen and they were blessed with a son they named Oakley.