Bob Pittman is Chairman and CEO of iHeartMedia, Inc., the number one audio company in America. Prior to iHeart, Bob has just had the most amazing career as a co-founder and programmer who led the team that created MTV. He has also led some of the most incredible turnarounds as CEO of MTV Networks, AOL Networks and Time Warner Enterprises and as COO of America Online, Inc. and later AOL Time Warner. In Today's Episode with Bob Pittman We Discuss: 1. From Flying Lessons to Radio: How Bob first made his way into radio at the age of 15? What does Bob know now that he wishes he had known when he started his career? What is the most painful lesson Bob has learned in his career that he is pleased to have learned? 2. Decision-Making in Leadership: How does Bob structure all decision-making as CEO today? Why does Bob ensure that all decisions are made within 24 hours? What are the pros and cons? How does Bob prevent consensus decision-making? How does Bob create dissent in a discussion? How do the best leaders know when to kill a project? What do most do instead? 3. Tactics vs Strategies: Why Plans Are BS! What is the difference between a tactic and a strategy? When is the right time to change your strategy and tactics? What have been Bob's biggest lessons on how to get teams on board with tactical changes? Why does Bob believe that plans are BS? When can they be useful? 4. The Secret to Messaging and Storytelling: What does Bob believe is the universal truth to successful consumer messaging? What has changed and what has not changed in the way companies tell stories to their customers? Is there a difference between a great product and a great company? What are examples? What excites Bob most about consumer habits today? 5. Bob Pittman: AMA: What does Bob believe is the success to successful parenting? How has it changed? How does Bob analyze his own relationship to money today? How has that changed? Why does Bob not believe in legacy? What do people get most wrong when it comes to ego?

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