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20VC: The Story of Turning Around MTV, AOL and Time Warner | How To Be Effective When Making Hard Decisions | Tactics vs Strategy and Why Plans Are BS with Bob Pittman, CEO @ iHeartMedia

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Dec 9, 2022

Bob Pittman, Chairman and CEO of iHeartMedia, shares his remarkable journey from co-founding MTV to leading turnarounds at AOL and Time Warner. He discusses the importance of swift decision-making, advocating for choices within 24 hours while managing dissent in discussions. Pittman believes that plans are often ineffective, emphasizing the need for adaptable strategies. He also touches on effective messaging and how early experiences shaped his career, highlighting the continuous process of growth and the role of innovation in leadership.

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ANECDOTE

Early Radio Days

Bob Pittman started in radio at 15 to pay for flying lessons.
He fell in love with radio after realizing the power of connecting with people through music.

ADVICE

Embrace the Unexpected

Embrace unexpected opportunities, even if they seem unconventional.
Bob Pittman's career trajectory was largely shaped by taking chances on underappreciated platforms like cable and the internet.

INSIGHT

High Performance Teams

High performance relies on a shared goal and teamwork.
Build teams with diverse skill sets where members complement each other's strengths and weaknesses.

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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?