Why Podcasts Need Structure: Finding The Funny With Creative Constraints

I've relaunched this Broadcaster Meets Podcaster column to tell my story as a radio broadcaster navigating through the world of podcasting. I'm launching a new podcast called The D Brief, and I'm sharing the lessons I learn from it with other radio broadcasters who want to do the same. If you missed my first column, you can find it here.

I have been a radio broadcaster for over 20 years, working on-air in medium and major markets, including New York City, Boston, Seattle, St. Louis, Providence, and Silicon Valley. Over the course of two decades, I've gotten good at the basic mechanics of being a disc jockey: frontselling, backselling, teasing, plugging the promotion, hitting the post, etc. As any experienced DJ will tell you, once you master the blocking and tackling, you can start playing around with them. And this is where the fun comes in.

I think I can be pretty funny on the air. But don't take my word for it; listen to my aircheck and judge for yourself:

A favorite technique of mine is to pull a pop culture headline from the news and find a way to mash it up with whatever song or artist I'm talking into or out of. The result is breaks that combine Taylor Swift and Mark Zuckerberg, Incubus and Kim Kardashian, or Led Zeppelin and Sean Spicer. Often, the humor comes from a reaction to the rules: I have to backsell the song, so I'm forced to find a humorous way to do so.

When I began podcasting, I assumed that the lack of rules fencing me in would allow me to be even funnier. In fact, the opposite was true. I quickly discovered that I was nowhere near as funny on my podcast episodes as I was on my radio shows.

My Taste Trekkers podcast series was built around one-on-one phone interviews, and while there were moments of levity, the laugh-per-minute ratio was far lower than on my radio shows. At first, I thought it might be because the interviews were over the phone. So I built a podcast recording setup that would allow me to go on the road and do in-person interviews. But interviewing my guests face-to-face didn't seem to amp up the humor quotient at all. So I was stuck, unable to figure out how to punch up my podcasts with punchlines.

Lessons from Stand-Up Comedy

I started dabbling in stand-up comedy a year and a half ago, and I have found that I struggle with writing jokes in the same way I struggle with podcasting: When you have a blank sheet of paper in front of you and you're trying to be funny, it's really hard. The hard challenge for me wasn't coming up with punchlines; it was coming up with premises for jokes.

One of the best pieces of comedy writing advice I received came from Chili Challis, a former writer for The Tonight Show with Jay Leno. "Comedy is about making lists," Chili said. "When you sit down to write, if you can't come up with anything, just start making lists." I eventually came to understand what he meant by this. Often, a great premise just sets up the pairing of two lists.

One night, I after a couple of glasses of wine, I made an impulse purchase on Amazon for something that I had absolutely no use for. When it arrived in the mail, I felt stupid -- but I also realized that I had a premise for a joke. So I made two lists: everything I know about Amazon, and everything I now about drinking alcohol.

For example, Amazon:

• Free two-day shipping
  
• One-click feature
  
• Amazon Prime
  
• Etc.

And alcohol:

• Two-drink minimums
  
• Designated drivers
  
• Alcoholics Anonymous
  
• Etc.

Then, I start pairing things up from the list:

• Free shipping with a two-purchase minimum
  
• Swigging Scope and clearing your browser cache to hide your drunk online shopping habit at work
  
• A 12-Step program called "Amazonics Anonymous"

And so on. Once I had a good premise, rattling off punchlines by combining items from my lists was easy. In fact, I've turned this combination of lists into a solid 5-minute routine that won me a recent competition at Mark Ridley's Comedy Castle here in Metro Detroit. That's how I learned that Chili was right - the trick is to find a premise that allows you to combine two lists.

The Problem with Blank Canvases

This experience made me realize that it's precisely the "blank canvas" nature of podcasting that makes it harder to be funny. With a blank canvas, you have to come up with premises. But on the radio, the rules provide me with those premises. I grab a headline from the news I'm forced to combine it with whatever song I am introducing. That's why punchlines flowed so much easier: The "walls" gave my mind something to bounce off of. They created joke premises.

This phenomenon is known as "creative constraints." Once I recognized it, it became obvious what I needed to do if I wanted to add more humor to my podcasts: I needed to put the rules back in. I need "walls" to bounce off of.

As radio broadcasters, there's something very tempting about the freeform nature of podcasts. But the best podcasts out there, from Serial to WTF to Hardcore History, aren't the ones with no rules; they're the ones with different rules. As you set out to create your first podcast, don't tell yourself that your show doesn't need any structure. Instead, tell yourself that the show can have any structure it wants, and ask yourself what type of "walls" will give you the most to bounce off of.

COMING UP: While my past podcasts have all had a basic structure in place, with my new podcast, The D Brief, I'm adding more "rules" than ever before in an attempt to maximize the opportunities for humor. In my next column, I'll explain how I'm doing this.