Bob Pittman desperately needed $10 for his first flying lesson but was turned down for a job at a retail store and another at Piggly Wiggly. Refusing to take no for an answer, he walked into his local radio station and managed to snag a position that paid $1.65 an hour – never imagining that this perseverance would set him up to become not only a pilot, but the co-founder and former CEO of MTV Networks, COO of AOL Time Warner, CEO of Six Flags, CEO of Century 21, and a co-founder and CEO of iHeartMedia – the leading audio company in the United States whose broadcast reaches over 250 million Americans every month. In this episode, Randall and Bob discuss:- Bob’s experience growing up in the segregated South- Leaving your comfort zone to identify problems and find solutions- How Bob’s passion for aviation led him to the radio industry- The necessity (or not) of a college degree- Moving a company from a $20 million operating loss to turning a profit within 18 months- How companies can create a brand without spending millions on marketing- Why success and failure are the same thing- The critical importance of marketing- The great opportunities in working for a company nobody’s ever heard of- 3 key elements to success- And other topics…Bob Pittman is a rockstar radio and TV programmer, marketer, investor, and media entrepreneur. He is currently co-founder, CEO, and Chairman of iHeartMedia, the leading audio company in the United States. iHeartMedia owns 863 radio stations, reaches over 250 million people every month, and had $3.85 billion in revenues over the last 12 months.Bob is also the former COO of AOL Time Warner after its $180 billion merger, the former CEO of Six Flags Theme Parks, the former CEO of Century 21 Real Estate, and the former CEO of Clear Channel Outdoor, one of the world's largest outdoor advertising companies. He is a founding member of the Pilot Group, a New York-based private investment firm whose investments include Huffington Post, Zynga, and Facebook. Bob is also a co-founder of Casa Dragones Tequila, a host of a podcast called Math and Magic Stories from the Frontiers of Market, and is also a dedicated philanthropist among many other organizations.Resources Mentioned:Incognito, by David EaglemanNew York’s Public TheaterRock and Roll Hall of FameTime Magazine’s Man of the YearSponsors:Sandee | Bliss: BeachesWant to Connect? Reach out to us online!Website | Instagram | LinkedIn