Sinclair is the co-creator, writer, and star of High Maintenance, a Vimeo web series and HBO television series set in New York City. The series is partially inspired by experiences from his personal life,[3] and first aired in 2012.[4] His final performance as his High Maintenance character was as a small cameo on HBO's Betty, also filmed in New York City.
Sinclair married his writing partner and High Maintenance co-creator Katja Blichfeld in 2010, after meeting at a 2009 party in Los Angeles.[5][6] They came up with the idea for the show while on a bicycle ride across the Williamsburg Bridge, and started the show in 2012.[6][7] Blichfield and Sinclair divorced amicably in 2016, prior to undertaking season two of High Maintenance.[2][6]