[1] Born in South Bend, Indiana, Leo grew up in Bloomfield, New Jersey, where his family was from and spent many formative years in the hardcore punk scene of New York City during the 1980s and early 1990s.

[1][7] The album was inspired by several years of career and personal hardships, including the loss of a daughter in 2011 due to a late-term miscarriage in which Leo's wife was forced to go into premature labor.

[1][8] For the 2019 animated television film Steven Universe: The Movie, Leo collaborated with Rebecca Sugar and Stemage to write the song "Independent Together".

As Steg, Leo performed "Independent Together" alongside Aimee Mann (who reprised her role as Opal from the Steven Universe television series) and voice actress Deedee Magno Hall (as Pearl).

His brothers, Chris and Danny Leo, are also musicians and have been members of bands such as Native Nod, The Lapse, The Van Pelt, The Vague Angels, and The Holy Childhood.