My guest today, Bob Pittman, has had one of the most interesting careers I’ve ever come across. Today, he’s the CEO of iHeartMedia, the country’s largest operator of radio stations and podcasts. Bob also created MTV, was the CEO of Six Flags and 21 Century Real Estate, and the COO of AOL and AOL Time Warner. He’s the Dos Equis man of business. In our conversation we discuss why convenience is king for consumers, his lessons from building MTV into one of the most iconic brands and media properties in the world, the rise of user-generated content platforms, and the future of media. We also discuss what qualities make for a great host, a topic that given my current position, is always fascinating. Please enjoy my great conversation with Bob Pittman. DocSend is a document sharing platform that enables companies to share business-critical documents with ease and get real-time actionable analytics. With DocSend’s security and control, startup founders, investors, business development executives, and financial professionals can drive business outcomes that have a lasting impact. Start for free at www.docsend.com. This episode of Founder’s Field Guide is also brought to you by NetSuite. Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly. Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at https://www.netsuite.com/invest. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:56) – (First question) – His personal interest that unites all of his business ventures (4:09) – His philosophy on the consumer (7:43) – Biggest quality mistakes business leaders make (9:31) – Respecting convenience in consumer preferences (11:08) – Founding insight to build MTV (16:23) – Fred Seibert on Math in Magic Podcast (17:14) – How the music video concept evolved with MTV (22:37) – Role of hosts vs guests in the media world (25:13) – Quality that increases the odds a host works (30:15) – Why everyone needs to know how to tell a good story (31:53) – Peak of his time at MTV (37:51) – Lessons for new media from his experience (43:46 – The largest uncertainty in the media landscape amid the rise of user generated content platforms (49:27) – Where he finds inspiration outside of business (55:40) – What Other People Say May Change What You See (56:16) – Different ownership structures and how they changed his behavior (59:09) – Finding and respecting your audience (1:02:11) – Lessons from time at Six Flags (1:02:24) – Most interesting thing about podcasting (102:52) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

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“What did the council decide on item 42?” — answered with the speaker and the moment.