The flipside of "taking risks" is having the resources to take those risks with in the first place. Especially the resources that if the risk doesn't pay off they can try again. It's not that average person isn't willing to take risks, it is that they don't have the opportunity to do so.
And yeah, life isn't fair and it should never be totally fair. But at the same time having it rigged against so many people is a big problem. At what point do you say "ok, you have won, good job, it is time to promote the common good now."