What's the origin of "Coolchief"?

When Randy Mason started a company to provide services to automotive dealers, he wanted something that was different.  Something other than the usually "Dealer blah blah blah" or "Automotive Professional fill in the blank".  While trying to think of something that would stand out Randy thought about something one his closest friends did when they were younger.  When his friend would arrive at the "gathering" he would walk in, and while pointing at several people, would say "Catdaddy, Wild Man, Coolchief.  Randy's first personal email was coolchief@ and has used that alias ever since.