It happened around 6:30 p.m. on the 800 block of North Markoe Street in West Philadelphia.
According to police, the 54-year-old man was sitting in a parked car with his friend when two armed men wearing dark clothing walked up and demanded their belongings.
"Both the victim and his companion were ordered to the sidewalk when an additional five males approached and began going through their pockets," said Captain Brian Hartzell with the Philadelphia Police Department's Command Inspections Bureau.
The 54-year-old victim, who lives on the block, was then pistol-whipped twice and shot in the hand before the suspects got away with $1,500, police said.
The victim's friend was not injured.
Police say they aren't sure if the men know their attackers.
No ballistic evidence was found at the scene, but police say the suspects got away in a grey SUV.
Anyone with information is asked to call police at 215-686-TIPS.