[2] Born and raised in New York City, Ross attended Harvard University, where he graduated Cum Laude with Honors with a degree in Visual and Environmental Studies, concentrating in filmmaking.

[10] Ross began making films in college, including the festival shorts Here Comes Your Man,[11] A Hero's Welcome,[12] Curtis and Clover,[13] Lola,[14] and Red Angel.

"[21] While in Los Angeles, Ross began raising money, cast, and production support on another project, Frank & Lola,[22] which would eventually become his directorial debut.

The other major parts were played by Michael Nyqvist (Alan), Justin Long (Keith), Rosanna Arquette (Patricia), and Emmanuelle Devos (Claire).

[24] During the festival, after the film opened to overwhelmingly positive reviews,[25] Universal Studios secured its worldwide rights (with the exception of a few minor territories) for over $2 million, with a theatrical release planned for later that year.

Ross wrote for the hit ABC series Nashville (writing two episodes and serving as creative consultant for Season 5),[31] in addition to selling several pilots to major networks.