In 2005, he and his family moved to Fairfax, Virginia,[3] where he auditioned for YG Entertainment and later met Kim Jin-woo of Jinusean in New York City.

In November 2013, while still a trainee, Bobby appeared in the music video for "Ringa Linga" by label-mate Taeyang of Big Bang alongside B.I and Jinhwan from Team B, Winner's Mino and Taehyun, and Blackpink's Lisa.

The show resulted in the debut of Team B, alongside trainee Jung Chan-woo, under the group name iKon.

[15] On October 4, the group attended their first music show, SBS' Inkigayo, receiving their third win for "My Type".

[17] Bobby also made an appearance on the ninth episode of Show Me the Money 5, featuring in Reddy's song "Like This", which they performed onstage together.

[20][non-primary source needed] In March 2017, Bobby and B.I featured in Psy's single "Bomb" from his studio album 4x2=8.

[24] On August 20, 2021, Bobby announced in his Instagram post his upcoming wedding to his fiancée, who was expecting their first child in September.