Valentine also considered raising money from Wall Street. But he lacked the polish and training that preppy New Yorkers expected. He had not attended an Ivy League college or an elite business school, and he hated conceited know-it-alls, a category that he defined to include “people with hyphenated names or roman numerals after their last name, direct descendants of immigrants who arrived on the Mayflower, people who had enjoyed living on the East Coast, and those who wore Hermès ties, suspenders, cuff-links, signet rings, and monogrammed shirts,” as a distinguished lieutenant wrote later.

