The famed venture capitalist, co-founder of Paypal, and early investor in Facebook, Peter Thiel has made a name for himself with a collection of counter-intuitive bets and well-funded initiatives. In the last election cycle, he personally donated $4.7 million to a handful of conservative groups, including Ron Paul's super PAC. His company, Clarium Capital, donated a further $3.8 million.
At the same time, according to Forbes, Thiel's net worth dropped by roughly $100 million, which means that his political donations far exceeded any direct benefit that he would have gotten if Ron Paul had been elected. Then again, the low-regulation business environment that Paul proposed might have been very attractive to Thiel.