What’s Letterman Got in Common With New Businesses?

Chad Wakefield
1 min readFeb 16, 2021

I’ve watched the Netflix Letterman series off and on over the past year or so. But recently I have rewatched many and caught up on all. It made me really curious to learn more about Dave’s beginnings. I’d been a fan since the 80s but I was pretty young and was not paying attention to People Magazine expose’s on him.

I am reading Jason Zinoman’s book on Dave that was released after he was fired from the Late Show (Letterman’s favorite bit about his retirement). In the “The Last Giant of Late Night” its written:

Letterman had saved some money, and now he had his first real Hollywood contact. “That was huge,” he said. He was ready to make the move.

Sounds like most of us who have started a business. You really have to have a few things fall into place. But you also have to be working your ass off and taking risks. Letterman got canned from a lot of gigs before he moved to LA; and even after.

You have to find your own voice and follow it. Others did not like his voice, so he did get fired a few times. But he kept on with it.

I very much felt that. In many stops, I made it clear how I thought things should be. And then took action without waiting for on high to follow my lead. When it became clear that no one was receiving it. Well, that was that. And off I went.

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