Jomboy rose to prominence on the internet in 2019 when he created a viral video showing with subtitles what New York Yankees manager Aaron Boone appeared to be saying during an argument with an umpire in a game. Jomboy gained further prominence when he published a series of videos appearing to demonstrate how a story in The Athletic reported that the Houston Astros were stealing signs in 2017. O'Brien is known for his ability to read lips and use videos to shed new light on sports topics.