Comment by ericmcer

Totally agree. For the 'Portfolio' strategy to be effective you need all the bets to be of a comparable size. If I place 20 $1 bets and 1 $10,000 bet, winning the $1 ones is going to be cold comfort to losing the $10,000 one.

Similarly if I regret a 10 year relationship that ends in divorce, something like finding a great new restaurant isn't going to even that out.