Tobeason graduated from Phillips Academy in Andover in 1976 and from Harvard University in Cambridge, Massachusetts in 1981. In 1988, he wrote the story for the Wiseguy episode "Smokey Mountain Requiem" which starred Jonathan Banks. He then worked as writer and producer on the short-lived television drama series Tribeca in 1993 for which he shared a Humanitas Prize nomination in the category 60 Minute Category in 1993 and a Writer's Guild of America Award nomination in the category Episodic Drama in 1994 with fellow writing and producing partner David J. Burke. The series featured Trek alumni Richard Kiley, Victoria Dillard, Caroline Kava, and Caroline Lagerfelt.