It's not clear what he means by apply. I assume he means that they only ever applied for one or two jobs without having been recruited/having a connection to the company already. Of course in another sense, everyone applies for every job they've ever had, because there's always some sort of approval process for hiring.

I don't think he means that top 1% only ever worked at one or two companies because that's certainly not true (that or he and I have very different ideas about what kind of people the top 1% are).

I would suspect Joel is discounting the summer work that young people do. i.e. he probably means: *They only ever applied for one or two [programming] jobs in their lives."

scholarships are pretty plentiful, if you're willing to do the application hustle.

I'm not sure why this would get downvoted. As a middle class white male in my major I was ineligible for a great many scholarships at my state university, and I was ineligible for most of the remaining ones because I had attended a concurrent high school and college program that did not publish class rank or inflate GPAs well beyond 4.0 as is common practice in normal high schools. As a result I could not get scholarships that required "(X on SAT or Y on ACT) and (Z GPA in high school or W percentile in high school) and *," in spite of my 800/710 SAT and 3.8+ GPA at the concurrent high school and college program.