Having grown up in a working-class New Jersey family with nine siblings, Barbara Corcoran starting working from a young age. By age 23, she had already worked 22 jobs, and her latest gig was a secretarial position for the Giffuni Brothers' real estate company.
While she was working for the Giffunis, Corcoran's boyfriend at the time fronted her $1,000 to start a real estate firm, she tells Guy Raz on the NPR podcast, "How I Built This": "He said to me, 'With your personality, Barbara, you'd be great at real estate sales.' I said, 'OK, I'll try it.' … The only person I knew was Mr. Giffuni, and I asked him if he would just let me rent one of his apartments."
Giffuni gave her a listing to try to rent for $330 a month. "It was a dungeon," she recalls. "He gave me the worst one. Maybe it was a challenge. Maybe nobody could rent it. Who knows."