In 2003, after the NBA draft, Paul joined LeBron James as a part of his small inner circle, along with James' childhood friends Maverick Carter and Randy Mims. 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, along with James, left Rose and CAA to start his own agency, Klutch Sports Group. 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. By 2019, Klutch had a roster of 25 clients and brokered over $1 billion in contracts. Later that year, United Talent Agency (UTA) asked Paul to run its sports division through a partnership with Klutch where he expanded the division’s clients from 4 to 23. In 2020, he accepted a position on UTA's board of directors.