New Adventures in Podcasting

A long-overdue re-brand is here

Five years ago, I sat my wife down in the living room, looked her in the eye and confessed the four words every wife fears most: “I’m starting a podcast.”

She stood up, patted me on my cranium and—to her immense credit—said, “Go for it!” So I did.

I didn’t know then exactly what the show was going to be. Along with Mike Carano, my editor and the guy who convinced me that a podcast about money and happiness was neither presumptuous nor a complete waste of time, I chose the name?Crazy Money?because, honestly, we couldn’t think of anything better. And, what the hell,we could always change it, right??

Almost 2,000 days and 222 episodes later, we’re making that change.

The coolest thing about having a podcast has been the opportunity to talk to people I would otherwise never have met. One of my favorite guests on?Crazy Money?has been author Oliver Burkeman who has appeared?twice. As with so many people I have encountered on this journey, I didn’t know of Oliver’s work until I stumbled across it, probably as an Amazon recommendation. If I liked Book x, Amazon suggested, I’d probably like Oliver’s book?The Antidote: Happiness for People Who Can’t Stand Positive Thinking. Oh algorithm, how you understand me!

At the time, I didn’t know who Oliver was or that he wrote a much-loved column for the?Guardian.?But when I saw the title, I knew this book was for me. It said that the author wanted to examine sources of fulfillment in life (me too!) and that he was skeptical about false positivity (me too!) and suspicious of the self-help publishing genre (also me too!).?

That’s what an effective book or podcast title should do - indicate to the potential reader or listener the content and tone of the show and, just maybe, a peak under the hood into the host’s curmudgeonly personality.

Unfortunately, "Crazy Money"?has never done that. While it plays on a double meaning about wealth and the fact that money can drive us bananas, it doesn’t offer the potential listener a clear hint as to the show’s purpose. It might be about getting out of debt, career management, or providing “a foolproof method to earn millllllionz in real estate while you sleep,” which explains the hundreds of off-the-mark pitches I get from publicists every year.

Speaking of which, a podcast name has to speak to both potential listeners and to potential guests. Last year, I received a warm introduction to Ed Begley, Jr.’s publicist and assumed that booking the actor was a slam dunk. But the publicist—who could not have been cooler—replied thoughtfully with this paraphrased question: “why would Ed do a show about making crazy money? This isn’t really on-brand for him…” After a long explanation that the show was about the connection between success and fulfillment, he gave me the green light, and I had a great conversation with Ed about his wonderful memoir,?To the Temple of Tranquility...and Step on It?(a truly joyous read).

Before Mike and I chose the name all those years ago, I hadn’t put any thought into the questions, “how do people discover podcasts?” or “by what criteria do desirable guests decide which shows they will or won’t do?” or “what would you think if you saw someone wearing a Crazy Money t-shirt?” (“what a d-bag!” comes to mind.)

But five years in, I wonder how many potential listeners have skipped over the show and how many potentially amazing guests have passed because the name was off-brand or—let’s be honest—a little bit cheesy. We’ll never know, my friends, but it’s at least dozens!

The new name is?Reasonably Happy?with Paul Ollinger. The conversations will remain mostly the same but we’ll shake up the show structure a bit, shoot all shows live, in person and focus a little bit more on fun than on cerebral self-gratification.

No, I don’t think this name change will immediately make the show the most popular podcast in the world, but the more I think about it, the more I believe it captures what I’m going after and who I am. It’s about making the proactive choice to be grateful even if we can be grumpy fucks a lot of the time. And there’s the peak into my psyche.

I have been very lucky in life, and I am pretty darn happy. But I am—like, I believe, most people—also chronically unsatisfied. I think this is a feature, not a bug in our wiring. This drive sometimes takes me out of the moment, but it has also driven me to succeed and keeps me moving forward. Despite all its downsides, anxiety gets shit done.

Listen on Apple Podcasts, Spotify or wherever you get your pod goodness.

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