[3] While working as an intern at The Fader in New York City, Siegel gave his mixtape Radio in My Head to Hip Hop director Rik Cordero.

They began producing videos to Siegel's tracks, which were then circulated to music executives, leading to offers from major labels.

[4] In June 2009, Siegel signed with Polow da Don's Zone 4/Interscope, with the support of Jimmy Iovine.

In March 2011, the song was aired on the Greek television show Radio Arvyla, and subsequently reached No.

[10][11] He then co-wrote and co-produced parts of Hoodie Allen's mixtape Crew Cuts, before releasing a collaboration album with Statik Selektah, Boom Bap & Blues, on February 26, 2013, which features Joey Badass and Action Bronson.

In the spring of 2019, Siegel started releasing a series of new singles, including "Permanent Damage" in March 2019,[16] "Dark Days" in July 2019, "Perfect Strangers" in September 2019, and "Sabotage" in December 2019.

[18] In February 2021, Siegel announced the project COLLAB, an album composed entirely of fan collaborations, which was released on March 19, 2021.

[22] He cites Bradley Nowell, The Beatles, Radiohead, Method Man, Mos Def, Al Green, Rza, DJ Premier, Stevie Wonder and Cream as his main songwriting influences.