Make some deal for Whiskey Bob

In Klamath, talk to Whiskey Bob in Maida Buckner's bar (The one near the city entrance). Give him a drink (5 caps - you can shovel shit in Klamath if you don't have any caps), then ask him if he can give you some job to do. He'll ask you to go in Den and tell something to The Hole's bartender (Frankie). Do this, then come back. Whiskey Bob will reward you.