Jerry Reinsdorf, a former IRS tax attorney who made his first fortune in real estate, has owned the Chicago Bulls since 1985, winning six NBA titles, and the White Sox for nearly 40 years.
Cyrus McCormick built a company around the mechanical reaper, with manufacturing, marketing and a sales force; it became part of International Harvester in 1902.
Richard Warren Sears was a Minnesota railroad station agent who, after a refused shipment of gold watches in 1886, went on to co-found Sears, Roebuck with Alvah Roebuck.
Marshall Field rose from dry goods clerk in Pittsfield to Chicago partner in 1862 and founded the department store that carried his name, later funding the Field Museum.
William Wrigley Jr. arrived in Chicago in 1891 with $32, sold soap and baking powder, and found his fortune when the free chewing gum premium outsold everything else.
Sam Zell, the Chicago-born son of Polish refugees who escaped on Sugihara visas, managed apartment buildings as a student and built a real estate and investment empire including EQ Office and Tribune Media.
Ray Kroc was a milkshake-mixer salesman who convinced the McDonald brothers to let him franchise their San Bernardino burger stand, bought the brand in 1961 and grew it into the world's biggest fast-food company.
Oprah Winfrey rose from poverty in rural Mississippi to host The Oprah Winfrey Show for 25 years and build a media empire including the Oprah Winfrey Network. She received the Presidential Medal of Freedom in 2013.
A kid who couldn't afford instruments at his local Guitar Center grew up to cover Slayer on banjo, drum in a Billboard-charting comedy band, and set a Guinness World Record for the largest guitar pedalboard ever built.
A Halo pro from the Chicago suburbs picked up a new battle-royale game in late 2017, then played it on stream with Drake — breaking a Twitch viewership record and becoming the platform's first 3-million-follower streamer within months.
