I hear this almost as much as the "90% of startups fail" piece of wisdom, and I was a little surprised to see it in a PG essay. I'm not saying it's necessarily wrong, just that I don't totally understand it.
Risk is "the possibility of suffering harm or loss; danger." So what's risky about a startup? If you are paying for it yourself, maxing out credit cards, etc, then the startup is indeed likely to be harmful to you.
But, if you get YC funding, and are the under 30 crowd that PG refers to with low living expenses, then it's pretty unlikely that you're taking that approach. Instead, you're simply not saving any money for awhile. So there is opportunity cost lost, since surely most of the YC founders could make a nice chunk of change working for the man. But is this really the harm that's implied by the reference to risk? Especially when you factor in the experience you gain from a failed startup, it seems pretty questionable to say that serious harm will likely befall you. It's more like, less savings and a great experience will likely befall you.
So I wonder if the sentiment is just referring to the harm that may happen to the startup itself. As in, it's quite likely -- 90% likely! ;) -- that the startup you create will die. But isn't that kind of like saying it's risky to scratch off a lotto ticket that someone gives you? It's "risky" for the lotto ticket I suppose, but not really for you.