If you are investing in a Hedge fund that's avg. 20% drawdowns and 65% winning months. Does it really matter when you invest in it? Would it help if you waited for a 15% drawdown before investing? Or waited for 1 or 2 losing months and put your money in? Personally, I think it would help but probabilistic, I don't think it should make a difference. A coin is 50/50, just because I have 3 tails in a row doesn't increase the chance of head the next flip any. So does waiting for losing months or drawdowns before putting your money into a hedge fund help increase your returns?