A single bad IPO from that list of firms (Which will likely happen in a climate of pessimism, even if we don't hit a recession) will be disastrous to their aggregate valuation, even if they stay private.
I feel that the only way Sam will win the bet is if none of the firms in #1 or #2 will IPO between now and 2020.
True, but conversely, one standout that does well could alone hit the target. If you believe that the successful companies follow a power law distribution, you'd expect something like that.
I feel that the only way Sam will win the bet is if none of the firms in #1 or #2 will IPO between now and 2020.