I'm very familiar with the satisfaction of beating someone while having worse equipment! A few weeks ago, a thin, young roadie on a fancy road racing bike tried to draft me. He had trouble keeping up with me. I got home and weighed my bike, a mid-90's Bianchi Volpe, loaded with every accessory known to mankind. With my gigantic Kryptonite chain and padlock, the whole setup weighed 48 pounds. The other guy's bike probably weighed less than half of that.
I also beat a young guy up a hill a few years ago. He was on an unloaded bike, and I was towing two kids in a trailer!