Your Prep school roommate didn’t necessarily surprise you when he chose to go to MIT. Now that his startup has successfully closed its B-round of funding, these 4GB USB Flash Drive Cufflinks ($195) will make a wonderful congratulatory gift. They’re practical enough that he might actually wear them, and they can be monogrammed, of course. Hopefully they will even give him the confidence to pick up a girl without you as his trusty wingman.