A friend of mine is a pilot for these types of folks (founders of non-tech household names), unless they're going to an event (say the Super Bowl), they fly into smaller airports.

There are many airports within easy driving distance of major metropolitan areas, and regardless of what happens, once they get off the plane they get into a car driven by a driver.

I don't think it matters much to them whether they spend the hour in traffic out of JFK, or on a highway from White Plains.

Most places I've lived, there are tiny airports much more conveniently located than the large commercial airport. I would absolutely fly out of smaller airports, but don't because I fly commercial, and if they even fly out of the smaller airports it usually means more stops.

Depends where you're going though. DCA looks pretty convenient if you're visiting the capital; but lots of big cities have smaller airports that are more convenient if you can land at any airport.