Besides YC investing in founders first (which I do believe is correct, having gone thru 2 batches), to quote the fictional S. R. Hadden from the book and movie "Contact," by the late, great Carl Sagan: "First rule of government spending, 'Why buy one when you can buy two at twice the price'." In other words, I believe this is also a strategy in maximizing investment exposure to great ideas. YC Invested in _both_ Box.net and Dropbox.