In the weeks leading up to David Letterman’s very last show, a procession of entertainers—from Tom Hanks to Tina Fey—stopped by his studio to thank him for inventing a new dialect of American television, a funny and irreverent language that inspired many talented young men and women to take risks and try out for a life in show business.
But actors and comedians aren’t the only ones that have much to learn from Dave; helming one of the most talked about TV programs for more than three decades, Letterman has much to teach all of us who labor to get a company, a non-profit, or any other sort of enterprise off the ground.
Here, then, as a tribute to the Master, are the Top 10 things you can learn from CEO David Letterman:
- Always bet on talent. In the spring of 1984, NBC executives were hard at work trying to figure out what to do about a renegade disc jockey who was making up raunchy games, trash-talking his corporate overseers, and ignoring most of radio’s perceived wisdom. To the suits in the executive suites, Howard Stern was a threat and a problem; to David Letterman, he was an uncommon talent. And so, while the NBC brass plotted to fire Stern and hired an attorney to operate a mute button in case Stern got too rowdy, Letterman, then still at the Peacock Network, invited Stern to be a guest on his late-night show. It was a bold move, as Stern was far from a national household name back then, and it helped the embattled radio genius cement his status and his reputation. The King of All Media never forgot Letterman’s support, and returned to Dave’s couch no less than 43 times.
- It’s never about you. America has many TV personalities, but only one with whom Joaquin Phoenix, say, felt comfortable carrying out his elaborate hoax, only one whom Drew Barrymore felt compelled to flash, and only one that, upon hearing that his friend Warren Zevon was dying of cancer, dedicated an entire hour to the dying musician. Like any other great leader, Letterman realized that he was always as strong as his team, and he worked hard to make sure his guests knew he was there to serve them, not the other way around.
- Assemble a stellar team. Can you imagine Letterman’s show without Paul Shaffer? Without Biff Henderson? Surrounding yourself with a stellar staff and letting them do their best work is essential to success.
- Don’t be afraid to be stupid. Would you like to see a blindfolded border collie catch a Frisbee? What about a Lab mix climb a ladder? Sure you would, and so, it turns out, does everybody else. It took Letterman’s daring to realize that sometimes, the smartest thing you can do is just be silly.
- Always innovate. Those who stick to the old formats rarely win. Those who wear Velcro suits and jump off trampolines and stick to felt-covered walls, on the other hand, thrive. Innovation doesn’t always pay off, but it’s never boring and always conducive to progress and growth.
- Be true to yourself. As he started his broadcasting career, David Letterman was tapped to host his own morning talk show. It was a big break, but it meant being warm and fuzzy and at-ease, things that Letterman is most decidedly not. Rather than trying to reshape himself to fit his lucky break, he abandoned the morning gig and waited for the right platform to come along. Within months, it did, giving Letterman his now-iconic late show on NBC.
- When you mess up, admit it. Finding himself in the midst of a blackmailing scandal that exposed his sexual relations with women who had worked on his show, Letterman didn’t shy away from taking the matter head-on. In a memorable on-air monologue, he addressed the allegations, spoke candidly about his misdeeds, and cleared the air.
- Refuse to put up with nonsense. On September 24, 2008, then-presidential candidate John McCain cancelled an appearance on Letterman’s show at the last minute, claiming he had to rush back to D.C. to attend an important vote. Letterman called in a substitute guest, but, midway through taping his show, learned that the senator from Arizona was down the street, taping an interview with CBS News. Furious, Letterman ran the raw feed of McCain getting his makeup on and prepping for the interview, hurling funny insults at the senator the whole time. It was more than just great television: it was a necessary reminder to politicians that someone is keeping tabs, and that there’s a limit to how far they can stretch the public trust.
- Be uncomfortable. After the terrorist attacks of September 11, 2001, most comedians hesitated before going back on-air. No one wanted to be the first to tell jokes when it was far from clear that America was ready to laugh again. But someone had to jump in, and that someone was Letterman: On September 17, he went on air to deliver what many call one of the greatest moments in TV history, being funny while still giving voice to the confusion and rage so many of us felt in those dark days.
- Know when to quit. He could’ve done his show for 30 more years, and we would’ve still watched. But like every truly great artist, Letterman realized that the only time to quit is when you’re solidly ahead.
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