Sir Richard Branson, founder of the Virgin Group, has an estimated net worth of $5 billion. When he spends his money indulgently, it's only to make money in return — like renting out real estate he owns, such as Necker Island. In fact, Branson once said in an interview that he's "embarrassed" by displays of wealth, like leaving large tips and buying things for "pure luxury." A member of the Giving Pledge, Branson would rather spend his money on philanthropy.