David LettermanAfter 22 seasons, more than 4,000 episodes and countless moments of laughter, David Letterman is set to retire from the late-night talk show business on May 20.

Letterman’s legacy in show business will live on, but other industries can also learn from the comedic genius, especially entrepreneurs.

In true Late Show fashion, here are the top ten reasons why entrepreneurs should channel David Letterman:

10. He Commands Respect

Though Jimmy Kimmel Live is a competitor of the Late Show with David Letterman, Kimmel will not air an episode of his show the night of Letterman’s final broadcast.

That’s because the comedian, like so many if his peers, has an incredible amount of respect for what Letterman does.

“I have too much respect for Dave to do anything that would distract viewers from watching his final show,” Kimmel said to The New York Times. “Plus, I’ll probably be crying all day, which makes it hard to work.”

To make a business work, entrepreneurs need to command respect from employees, vendors and even competitors.

9. Letterman Doesn’t Always Play Nice

Other than his comedy, Letterman is also known for feuding with high-profile celebrities, like Oprah, Madonna and Jay Leno.

Letterman was famously outspoken when Leno got chosen as Johnny Carson’s replacement for The Tonight Show in 1992, voicing his displeasure on multiple occasions before getting a job on a competing program.

In business, nice guys sometimes do finish last. Entrepreneurs don’t need to be unpleasant, but they may have to play rough from time to time.

If deadlines or goals aren’t being met, entrepreneurs need to be able to lay down the law sometimes.

8. He Knows When to Make Amends

Though Letterman had some famous feuds, he also knew when to let things go. After decades of feuding, he had Oprah on his show in 2005.

He, Oprah and Leno also appeared together in a commercial for the Late Show’s coverage of Super Bowl XLIV.

Since being an entrepreneur requires the ability to make connections with many different type of people, it is important to know when to take a step back, even after an issue.

7. He’s Adaptable

It is not easy to stay relevant after decades in the entertainment industry, especially on a show that comes on each night during the week. But Letterman has managed to keep the audience laughing for all of these years.

Entrepreneurs need to have vision, but it is just as important to be able to adjust that vision as society changes or technology advances.

6. Letterman Gets Branding

There are few people that can be recognized around the world simply by the sound of their laugh, but Letterman is one of them.

From his recurring segments on the show to his brand of humor and personal look, Letterman has a very clear brand that people respond to.

Branding is essential for entrepreneurs to understand. It is more than a logo, it is a reflection of the entire mission and purpose of the business. It is crucial to get it right.

5. He Isn’t Afraid to Try New Things

Though talk shows were around long before Letterman, his creativity and willingness to try new things completely changed the game.

Instead of pretending that the backstage world of cue cards, rehearsals, writers and producers didn’t exist, Letterman broke the fourth wall and made it all part of the show’s comedy.

Entrepreneurs have to try new things as they build their businesses. Testing is also important to make sure that the choices are made based on tangible data.

4. Letterman Brings Out the Best in Others

One of the reasons that Letterman has been so successful is because he knows how to bring out the best in the people around him. He makes he everyone talks to funny.

Entrepreneurs should be able to inspire others to be their very best. Especially with the small teams that are common in start-ups, the leaders need to be able to bring out the talent in their employees.

3. He Understands the Importance of Timing

Timing is the most important tool in a comedy. Letterman has impeccable comedic timing that allows him to milk every moment of a show.

Entrepreneurs need to have excellent timing as well. Timing will help to keep projects on track, make sure that funding is secured by the right deadlines and keep the company growing in an upward direction.

2. Letterman Gets His Audience

In show business and actual business, knowing your audience is key. Letterman knows what his viewers like and he consistently gives it to them. He also understands them well enough to surprise them with new material and still make them laugh.

For a new venture to work, clearly defined audiences are a must. Marketing, business strategy and product development should all be done with a specific audience in mind.

And the No. 1 Reason That Entrepreneurs Should Channel David Letterman: He is the Ultimate Influencer

Jimmy Kimmel, Conan O’Brien and so many other entertainers consider Letterman to be a major influence. Even after his last show, Letterman’s impact will continue to be felt in the world of comedy for a long time.

That should be the goal of any entrepreneur, to leave a lasting mark on their industries. A strong product or service is great, but the ultimate goal should be to be the company that people think of when they think about that product or service.


Erin PalmerErin Palmer is a writer and editor with a soft spot for late night talk show hosts. Her work has appeared in numerous publications and websites, including The Chicago Tribune and The Huffington Post.

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