In 2002, Bartholomew won the National High School Chess Championship, and in 2006 became an International Master (IM). He studied at the University of Texas, Dallas on a chess-based full ride scholarship, which he earned at the age of 14.[3] After leaving law school, he became the coach of David Floeder, a middle school student who won the National K-12 U.S. Chess Federation Championship in 2012.[4][5] Bartholomew earned his first Grandmasternorm at the Saint Louis Classic in 2013.[6] He is a four-time winner of the Okoboji Open.[7]
He has a dedicated YouTube channel of instructional chess videos and is one of the most popular chess YouTubers.[8] He is the co-founder of Chessable together with David Kramaley ─ a chess education website dedicated to teaching chess in a systematic manner.[9] The project was launched in November 2015 and the website was officially launched on February 22, 2016.[10][11] In September 2019, the company joined forces with an existing merger of Play Magnus AS and Chess24.com.[12]
In January 2018, Bartholomew earned clear first place in the Charlotte Chess Center's Winter 2018 GM Norm Invitational held in Charlotte, North Carolina with an undefeated score of 6.0/9.[13]
In 2019, Bartholomew was inducted into the Minnesota Chess Hall of Fame.[14]