Up Front: October 2015

Bob Pittman, who runs America’s largest radio network, told me during our interview for this issue that he actually demands mistakes in the workplace. I believe him.

He said he learned an important lesson early in his career from his mentor, Warner Communications founder Steve Ross, who told him, “You will never be fired at this company for making a mistake…we fire for not making mistakes, because mistakes are the byproduct of innovation.” Considering the amount of innovation Pittman has stewarded in the media world, it’s obvious that this philosophy has worked for him. 

It occurs to me, however, that when it comes to the upkeep and flying of his Falcon 900EX, he is a perfectionist. It is a beautiful aircraft, meticulously maintained and managed by the Teterboro, New Jersey-based team at Gama Aviation. As Gama president and CEO Tom Connelly told me, “Bob is very particular about the condition of his aircraft and the status of the maintenance, more so than the average aircraft owner, because he flies it himself.”

Indeed he does. Pittman—who has an Airline Transport Pilot’s rating for airplanes and current type ratings for helicopters and three jet variants—expertly flies himself not only around the U.S. but also into some of the most challenging airports in other parts of the world.

I couldn’t help but ponder the apparent dichotomy between these two personas: Pittman is a CEO who encourages mistakes in the workplace and also a pilot who clearly seeks to avoid even the slightest misstep in the cockpit.

But maybe it isn’t such a dichotomy after all. Pittman understands that mistakes in the office can easily lead to the next quantum-leap and also that error-free operation is essential in the sky. And he’s consistent: this is a man who, whether on the ground or in the cockpit, always strives for the best.