What I've learned from hosting several hundred episodes of "The Puzzler" podcast

I’ve learned many important things during my year of hosting the daily podcast, “The Puzzler.”

I’ve learned, for instance, that wombat poop comes in the shape of cubes (a fact I discovered while researching a puzzle about marsupials). I learned that a knocknobbler was an old occupation whose duties involved chasing dogs out of churches (for a puzzle about jobs).

But I also learned — at least, I hope I’ve learned — how to make a better show. I’ve written some of these lessons below. My hope is that they might be applicable to other creative endeavors, and not just puzzle-based daily podcasts (but for those too).

NOTE: For those who don’t know, “The Puzzler” podcast is a daily show where we give our guests audio word puzzles. It’s produced by iHeart, which recently renewed it for a second season. I do it with a bunch of great people, including Chief Puzzle Officer Greg Pliska. We’ve had guests including Dax Shepard, Joseph Gordon-Levitt - as well as Julie Jacobs and Jessica Pliska (pictured above).

DON’T BE AFRAID OF MISTAKES

At first, I was terrified of making a mistake. What if I mispronounced “Nietzsche” or “Colonel” or “Adele”? I’d lose all my cred.

But 13 months in, I’ve learned that mistakes aren’t a bad thing — as long as you admit to them and correct them as soon as possible. (And as long as your show isn’t about surgery techniques or something).

In fact, making mistakes can have some upsides. First, admitting we’re wrong is just a good thing in a world filled with toxic certainty. Second, the errors engage our listeners, some of whom take well-justified glee in emailing us about our flubs. Third, it can lead to interesting discussions. Recently, I gave a puzzle about classic sitcoms, and I mistakenly said that CBS refused to show Lucille Ball pregnant. This was not true. They did show her pregnant. They just didn’t allow anyone to utter the word “pregnant.” The characters had to use the much more civilized word “expecting.” When a listener pointed out my error, I went down a lovely Internet rabbit hole about early television taboos, such as NBC’s refusal to let Tonight Show host Jack Paar say the phrase “water closet” because it means bathroom, and he quit in protest. This inspired us to do a puzzle about phrases with the initials W.C.

SPEAK DIFFERENTLY

Even at the start of the show, I knew enough to avoid speaking in a monotone. Unless you are Steven Wright, monotone isn’t a winning strategy. But in addition to monotone, I’ve learned to try to avoid anything else mono. I steer clear of monospeed, monovolume, monosentence-structure.

For better or worse, the human brain has evolved to crave change. Otherwise, it starts to tune out. So I try to vary my speed (talk fast, slow down on an important point), and my volume (raise it when I want to emphasize a phrase), my sentence structure (throw in questions and exclamations along with declaratives), and anything else I can think of.

I try to take inspiration from comedian Jim Gaffigan, who is brilliant at changing his tone from sentence to sentence, or even word to word.

TAKE ADVANTAGE OF THE MEDIUM

The first time I sensed that there could be a Puzzler podcast was when I narrated the audiobook of The Puzzler. I felt bad for the listeners since they were missing out on several visual puzzles contained in the paper-and-ink book (sudoku, for instance, is not audio-friendly).

So, I brainstormed a bunch of ideas that might only work in audio and not on the printed page. A lot of them were terrible. But some clicked — such as a puzzle that’s sort of an audio version of a rebus. I’ll say a word using a specific tone or accent, which is a clue to a two-word solution. So, I’ll say the word “fidelity” but in a high-pitched voice, and the answer would be “high fidelity.” Or I’d sing the word “chairs” in an operatic voice, and the answer would be “musical chairs.” Earbuses have become a popular feature on the show.

Every medium has its strengths and weaknesses, and for the podcast, I try hard to lean into puzzles that exploit audio.

FIND A THEME AND VARY THE BEJEEZUS OUT OF IT

I always admired the intro to The Simpsons. I love how, in every one of the 778 episodes so far, Bart writes a different phrase on the chalkboard (e.g., “The cafeteria deep fryer is not a toy.”)

For the first episode of The Puzzler, I said “Welcome to the Puzzler podcast, the cherry on your puzzle Sundae.”The next day, inspired by The Simpsons, I figured I’d try a different phrase. “Welcome to the Puzzler, the Miracle-Gro in your puzzle garden,” or the “free WiFi at your puzzle coffee shop.”

I’ve been doing new phrases for 300 episodes, with those phrases getting increasingly convoluted and absurd. It still sparks a bit of joy for me — and at least some listeners, too. Listeners have started to send in suggestions — in fact, about half of the intros are from listeners, including “the propellor atop your puzzle beanie” from Sri Kumar.

THE MORE THE MERRIER (AS LONG AS IT’S THE RIGHT MORE)

At first, I figured two voices would be ideal — me and a guest. Anything more might be confusing for the listeners. That turned out to be wrong. Now, every episode, our Chief Puzzle Officer Greg Pliska joins the conversation, either as a commenter, solver, or the one delivering the puzzles. I find Greg adds so much energy and just the right amount of chaos. I mean, it helps that Greg is brilliant and funny.

When there’s no guest, and it’s just Greg and I talking, we’re increasingly bringing in Associate Puzzler Andrea Schoenberg to provide another voice. I think this multiple-voice isn’t just applicable to podcasts. When writing my books, if I have to explain a complex topic, I often do so as a dialogue between an expert and me. It can make it more readable.

In addition to lessons about the structure of shows, I also learned a ton of random information when researching puzzles. So, I’ll end with a small sample of those.

—Bart Simpson is named “Bart” because it’s an anagram of “brat.” Or at least that was some of the motivation.

—Eye Rhymes are words that look like they should rhyme but don’t, such as “lemon and demon.”

—A word in which each of the vowels appears once and only once is called a supervocalic. Which is itself a supervocalic. Other supervocalics include ambidextrous and delusional.

The guy who voiced Astro the dog on The Jetsons is the same guy who voiced Scooby Doo.

Oh, I also learned that there’s no way we could do the show without the awesome Puzzler team, including producers such as Neely Harris (who first approached me with the idea), the visionary Adam Neuhaus, the most beloved man in podcasting Jody Avirgan, Brittani Brown, Claire Bidigare-Curtis, Andrea Schoenberg, Samantha Dwig, and our iHeart producer Lindsay Hoffman.