The comparison between buying at the bottom and buying a winning lottery ticket is silly. I also bought, with borrowed money, a few weeks after this guy (in Feb. 2009). I also bought, with borrowed money, in Aug. 2015 and January, 2016.
When you buy low, you don't have to be a genius to know that you can sell anytime the market or your stocks are higher.  So knowing when to sell is a non-issue.
I think your comment is a criticism of a smart guy who has demonstrated that he knows what he's doing.