Stein earned a B.A. in 1987 from Columbia College of Columbia University and later received a Master of Fine Arts degree in film from the University's School of the Arts. Subsequently, Stein worked as a director, producer and/or writer of documentary films, several of which won awards. In 1991, he co-produced an Academy Award winning short film, The Lunch Date. He then co-produced The Last Party, a film commentating on the 1992 Democratic National Convention. Stein also produced and directed a documentary about his sister's brain surgery, entitled When Your Head's Not a Head, It's a Nut.

In addition to his films, Stein took up creative writing. At one time, he taught creative writing at Tacoma School of the Arts. He has also published three books and one play, Brother Jones, which was produced in Los Angeles, California in 2005. His first published novel was Raven Stole the Moon (Pocket, 1998). His second novel, How Evan Broke His Head and Other Secrets (Soho Press, 2005), was selected as a BookSense Pick and won a Pacific Northwest Booksellers Association Award.

The Art of Racing in the Rain

Stein's recent novel, The Art of Racing in the Rain (Harper, 2008) became a New York Times bestseller and a #1 BookSense Pick.

The novel follows the story of Denny, a race car driver and his dog Enzo, who believes he will be reincarnated as a human — following the Mongolian legend that a dog who is prepared will be reincarnated in their next life as a human.

Stein was inspired to write the book after viewing a documentary on Mongolia called State of Dogs and after hearing a reading of the poem "The Revenant," told from a dog's point of view. The race car driving experience of the novels character, Denny, is based on Stein's own experience racing cars. Stein moved from New York City to Seattle in 2001 and became involved in "high performance driver education," received his racing license with the Sports Car Club of America won the points championship in the Northwest region Spec Miata class in 2003. and left racing after a serious crash — while racing in the rain'

Stein was born in Los Angeles, grew up in Seattle, and after spending eighteen years in New York City, returned to Seattle. Stein lives in Seattle with his wife, Andrea Perlbinder Stein, sons Caleb, Eamon and Dashiell — and the family dog, Comet, a lab/poodle mix. When living in New York, played in a rock band, called Zero Band, that rehearsed but rarely performed.