He can't, and David Jolly is pretty bad at it. Look no further than his first debate against Alex Sink earlier this week.
He lobbied for Social Security "reform," in other words, to privatize it, but now has a different view? He lobbied to turn Medicare into a voucher program, but now tries to sell himself to the "get your hands off my Medicare" crowd? He lobbied for clients to get their hands on the stimulus that the Tea Party so vehemently opposed, but now that same stimulus was a bad idea?
Sure, he claims he's against all the right Tea Party demons: Obamacare, abortion, and immigration reform, but he's also spent most of his time in Washington raising money instead of campaigning here in Florida, because he's a lobbyist. Where else would he be?
It takes a lot more than an address to be considered an "insider," but Tea Party voters may not get the kind of insider they think.