Lipinski's father Joseph hoped his son would enter into the medical profession, but Tom caught the acting bug for the performing arts in an experimental theater troupe while at Brown University, where he majored in history from 2000 to 2004.

After earning a degree, Lipsinki explored experimental stage performance at The Theatre of the Two-Headed Calf in Rhode Island, among other venues.

[1] Prominent directors under which Lipsinki has worked include Jason Reitman, Steven Soderbergh, and Paolo Sorrentino.

[1] Besides acting, Lipsinki has become a writer, director, and producer, making his directorial debut in Ben, a 2013 short film.

In 2021, he co-created and produced twenty-one episodes of Gone South, a journalism podcast series that has investigated high-profile cases, such as the unsolved murder of a New Orleans Assistant District Attorney.