After graduating
Phi Beta Kappa from Stanford, his first job was as an interim spokesperson for former President Clinton at his
Harlem, New York office. This was followed by working as an aide for
Senator Hillary Clinton at her D.C. office. His first media break was getting a job in the
Creative Artists Agency (CAA) mailroom. Being Canadian he needed a work visa, and CAA made an exception to their standard practice to sponsor him for one. working his way up to agent, representing
Katy Perry,
Arnold Schwarzenegger,
Jesse Eisenberg and
Bruce Willis, among others. He left in 2018 to co-found a media and financial investment-advisory firm, K5 Global. In June, 2023, K5 reported over $1 billion in managed assets and investments in 148 companies apart from funds linked to
FTX. He introduces clients to "a who's who of business and social leaders, from
Leonardo DiCaprio to the governor of the
Saudi Arabia Public Investment Fund." A beneficiary of Kives' network was
Sam Bankman-Fried, the former FTX
CEO. Bankman-Fried was connected to
MasterClass, President Clinton,
Orlando Bloom,
Nelson Peltz,
Bobby Kotick,
Larry Fink, and Katy Perry, among others. The relationship between Kives and Bankman-Fried has been noted to be mutually beneficial. Bankman-Fried invested $700 million in K5 Global, with Kives receiving $125 million as part of the deal. Bankman-Fried was alleged to have said Kives was “something of a one-stop shop for relationships that we should utilize.” the $700 million, claiming that the investment was made to burnish his own political and social influence. In January 2025 FTX reached a settlement with K5 resolving the lawsuit. FTX CEO
John Ray called K5 a bright spot in the FTX portfolio and stated that the investment in K5 will play a large role in the recovery of FTX. ==Personal life==