In his book "How to Get Rich" he related his hint to pioneer PC-magazines publishing to his interest in early PC-games.
This seems to be the case PG wrote recently in his latest essay - when someone is experiencing a new thing purely as a user, not developer, and feeling and thinking about what's still missing that could be useful to others like him.
How about the thousands of guys who tried to imitate Penny Arcade's success with their own comic strips? Most webcomics aren't that profitable and gamer oriented comics are probably the most saturated market. It's like acting, some hit it big, most struggle in obscurity for years.