4 Smart Business Lessons You Can Learn From David Letterman

May 21, 2015

On May 20, David Letterman closed the curtain on his epic 33-year run as America’s favorite late night television host. The emotional, star-studded finale (which included a montage from nearly every living US president) was an appropriate send-off for a man who’s been referred to as one of the most influential people in television history. It’s hard to overstate the impact that Letterman has had on comedy and television, but this wouldn’t be a small business blog if we didn’t provide you with the entrepreneurial angle. Here are our top 4 small business lessons that you can take away from David Letterman.

1. Don’t Take Yourself Too Seriously

Letterman is famous for making jokes at his own expense, and his sendoff show was no different.  Entrepreneurs can learn a valuable lesson here. When you put everything on the line to start your small business, sometimes you’ll need to sit back and laugh at yourself. It will help you cut down on stress and stay sane while you’re on your road to success.

2. Keep Yourself Organized with Lists  

Letterman’s Top 10 List is a popular segment in which he, in typical letterman style, pokes fun at pop culture or makes irreverent jokes. Starting your day with a top 10 list is a great way to keep yourself organized and prioritize key activities for your day. If something doesn’t get checked off by the end of the day, re-evaluate how important it is and weather it needs to make it to tomorrow’s list.   

3. Turn Your Setbacks in to Success

In 1992 when Johnny Carson ended his own career on NBC’s ‘The Tonight Show’ many assumed that Letterman would take the reins from his mentor. So when Letterman famously lost the show to his rival Jay Leno it was a major blow to his career and ego. Rather than letting that failure define him, Letterman instead picked himself up and turned that public upset into unending fuel for comedic material when he moved to CBS and launched ‘The Late Show with David Letterman’.  Now David Letterman is retiring as the undisputed king of late night. Protect your startup against the worst kind of setbacks with small business insurance so you can quickly bounce back.

4. Have the Courage to Be Yourself

What sets Letterman apart from his contemporaries is his unique brand of goofball humor. Long before Jimmy Kimmel and Jimmy Fallon started their late night antics, Letterman’s "Stupid Pet Tricks" And "Monkey Cam" segments were groundbreaking in their comedic elements. Likewise, small business owners shouldn’t be afraid to inject a bit of their own flair or personality into their branding. When it comes to marketing, especially on social media, strive to be your authentic self and make connections. When done right, your audience (customers) will appreciate your one-of-a-kind touch.  

Are you a Letterman fan? What other small business lessons do you take away from his career? Let us know in the comments!