While living in Miami in 2011, Esmailian's friend, Hawk Marley, sent him some of singer The Weeknd's tracks when the artist was relatively unknown. Esmailian then drove to Toronto, Canada and began managing The Weeknd. In 2012, Esmailian, Slaiby and the Weeknd founded the XO record label as a joint venture with Republic Records. Through the XO and Republic partnership, the Weeknd released several albums in the following years, including "Trilogy" (2012), "Kiss Land" (2013), and "Beauty Behind the Madness" (2015). The latter album would be honored with two Grammy Awards. Along with Slaiby, Esmailian was named to "Billboard"s "40 Under 40: Music's Young Power Players" list in 2015. Esmailian was also pivotal in the 2016 release of "Starboy," the Weeknd's third studio album that debuted at number one on the US "Billboard" Hot 100, received triple platinum certification and won Best Urban Contemporary Album at the 2018 Grammy Awards. On March 20, 2020, XO and Republic Records released the Weeknd's fourth studio album "After Hours". The album debuted and peaked at number one on the US "Billboard" Hot 100 and received platinum certification. In March 2020, "After Hours" broke the record for the most global pre-adds in Apple Music history, with over 1.02 million users.