If we can come up with a plan to successfully break into a major corp site full of security I'll bet we can figure out how to successfully burglarize a jewelry store over a weekend.
Nah don't rob a jewelry store, hospitals or home good stores are easier, less likely to be traceable, and provide better return. It's hard to move a lot of jewelry, unless you've got a fence that runs their own jewelry storefront and will forge the paperwork, and you're not going to get market value selling whole sale because of the huge mark up on gems and gold when sold at retail (jewelers pay less than 50% of the sale price when buying wholesale, which depresses the illegal market). You're probably looking at a few percent of the value that the jewelry store could have gotten from it, if you're lucky. Stolen prescription medication drugs maintain a good value on the street and so does laundry detergent.
My guess is, the real top of the world guy probably knocks off a stuffer shack every other Tuesday just for kicks and stays the hell away from anywhere with serious security.