Is it just my imagination, or.......

viaggio,

Heh, if you forget Rip's backstory, you can easily consider his character here to have more in common with Spade and Marlowe than with a taxicab company owner. He is functionally a detective in this film.

street smarts

He seems to have had some connections to the criminal world in his previous occupation. Hence his ability to locate a safe cracker and someone who could bring him a “persuader” on short notice.