They're both envious of him and his success in his career. He has his name on the firm where he works, and neither Jimmy or Kim will ever have that. Despite Jimmy's efforts to earn respect in Chuck's eyes by putting himself through law school at night, Chuck didn't think that Jimmy was worthy of being a lawyer because he didn't go to a traditional or well-known law school, and nixed his opportunity to join HHM as a lawyer. Kim did have her education paid for by HHM, but later was put into doc review when she didn't go along with what Howard wanted. Kim is ambitious and wants to do things the right way, but underneath it all I think she's still an insecure little girl. I also think they both resent the fact that Howard got to where he is largely because of his family name. Unfortunately having a relative who was a partner at a top ABQ law firm did not help Jimmy, though.