Oliver Leopold was the youngest Bootstrapper we've ever had on the show. his first appearance was in 2012 as a 10-year-old. He was getting publicity when he wrote his own investment letter and was also featured in the Wall Street Journal. He is now a senior at Evanston Township High School. Since then, Oliver has become more involved with stocks and options, and several other ventures; he's written two books, one being The YouTubers Handbook, and has founded the startup, PrimarySearch. He'll be going to college in 2021 and wherever he goes and they'll be lucky to have him.