One Wall Street billionaire and the ultimate college hedge.

Ava Kofman and Daniel Golden:

One of her areas of expertise is how to pay for college. In her writing, media interviews, and YouTube videos, she cautions parents not to “follow the herd with your donating dollars” or pin their hopes for their children on getting into brand-name colleges. “Don’t believe the hype,” she tells them. “You might find yourself obsessing over those annual college rankings. Don’t take them too seriously.” The sensible solution, she argues, is for families to “pick a few financial safety schools” — public universities close to home. A degree from an elite college, she reminds readers, may not translate into higher earnings in later life. “The Ivy League isn’t necessarily the gravy train.”

This is not quite the message imparted by Horace Mann, the exclusive prep school where the Shaws sent their children. At Horace Mann, the need to battle for slots at the nation’s most prestigious colleges is ingrained in students from an early age. Peers of the Shaw children remember classmates talking about where they wanted to go to college — and understanding that they might very well not go there — as early as the sixth grade. “It is difficult to dodge the school’s reputation as a ‘pressure cooker,’ college-obsessed school when, for example, a seventh-grade class has divided into teams named after the eight Ivy League institutions,” noted an editorial in the school’s newspaper, The Record, in a 2014 issue printed shortly before Rebecca Shaw’s graduation.