Theodore Black has started 37 different companies in this three decades as an entrepreneur, each of which has been shut down within a year due to government investigations, negative press, or waves of sexual harassment claims. He hires his nephew, Toby, to work in company number 38 (a diet pill telemarketing business). Toby is a naive young college graduate eager to learn the keys to business success, and he rises quickly from making telemarketing calls to producing infomercials. While building the new company together, Toby and his uncle fight for the heart of the company receptionist, Linda, and struggle to ward off an investigation by the Federal Trade Commission that could land both of them in prison.