He used to look for answers about the Matrix with his old friend Harold Hobbs, and after being freed by a redpill he goes to talk to him, leading to Harold being contacted by an Agent about his whereabouts and for him to be watched and followed. Jeff contacts him through his computer (like Trinity did to Neo in The Matrix), saying not to tell the Agent anything and that he'll be in contact. From the file the Agent has on him he appears to know Trinity.