In 2003, after the NBA draft, James asked Paul to be a part of his small inner circle, along with James' childhood friends Maverick Carter and Randy Mims. Paul quickly obliged. He would later start working under Leon Rose, who had negotiated James' extension with the Cavaliers in 2006, at Creative Artists Agency. In 2012, Paul left Rose and CAA to start his own agency, Klutch Sports Group, and took James with him. In 2013, Paul enlisted noted long-time agent and attorney Mark Termini to run the NBA contract negotiations for Klutch. By the conclusion of their agreement in 2020, Termini negotiated $1.4 billion in NBA contracts for Klutch Sports clients from 2014 through 2019. Later that year, United Talent Agency (UTA) asked Paul to run its sports division through a partnership with Klutch where he expanded the sports clients from 4 to 23. In 2020, he accepted a position on UTA's board of directors. Paul also expanded its clientele at Klutch to include the National Football League (NFL) by hiring former player Damarius Bilbo.