Taylor Stein started off acting in community theatre, before taking a gigantic step forward into high school theatre. After only three years of high school productions, he felt the need to start his own production company with fellow funnyman Chris Onken. The production company is aptly titled Onken-Stein Productions.
Moving on. In the fall of 2001, while in college, Stein joined Omaha improv group, Spot Theatre, before co-developing the University of Nebraska at Omaha cult classic, fake reality show, Post Modern Television. From there he went on to direct, produce, and co-star in the "Made For TV/For My Thesis" film, Fair Enough. A year or so passed without anything funny ever happening, until 2005 when Stein joined Mr. Chicago's Improv Comedy Troupe. Then, in summer of 2006, Stein became the host for Omaha alternative entertainment show, The KXVO 10:00 News. He hosted and produced comedy, blended with hot chocolate and race cars, for a month before turning over the host reins and becoming the producer of the show that was more of a sketch comedy and entertainment satire than actual news program.