Note: The audio version of the “That Was Stupid” podcast is ALWAYS available for free right here and wherever you listen to podcasts. Click here to find it on your favorite platform.
I wasn’t sure if I was ever going to be able to say these words, but I am: The “That Was Stupid” podcast is back!
Some of you may have no clue what I’m talking about. If you give me a minute, I can explain.
In early 2023, I hit a rough patch. Part of what I do is media consulting, drawing on my years in the news business and building digital platforms. But in March of that year, I lost my biggest client. The company’s founder actually called me up while I was boarding a plane with my daughter and took about two minutes to break the news.
And just like that I had way more time on my hands than I wanted.
So I decided to do something I had always wanted: start my own podcast. I had hosted other people’s podcasts before, but never my own. And I had this idea that had been ruminating in my mind for awhile.
See, I’ve always been inspired by stories of people who took chances, who took a leap of faith, who did what others told them would never work. Part of the reason is because I am overly cautious, so maybe I live a little vicariously through these people.
I wanted to hear stories of people who heard “that was stupid” when they took their chance, and then they got the last laugh.
I’ve always been inspired by stories of people who took chances, who took a leap of faith, who did what others told them would never work. I wanted to hear stories of people who heard “that was stupid” when they took their chance, and then they got the last laugh.
So I took my own leap of faith and launched “That Was Stupid.” It's a fun, informative, and candid show interviewing business people, celebrities, influencers, newsmakers, leaders, and even regular people about monumental, life-changing decisions that caused everyone at the time to say, "That was stupid!" Those decisions, though, ended up being incredibly rewarding and either changed the person, the landscape, or the world.
Season 1 was a blast. We interviewed Miss America about leaving America; we talked to an ESPN star who gave it all up to work for a non-profit; and we even talked to a successful businessman who drank sewage in order to bring the world clean water.
We took a break last May to work on some other things; most importantly I took a break to work on myself. You’ll actually be getting that story very, very soon. But now we’re back!
For Season 2, we have some great guests lined up, including a worship pastor who left ministry to become one of the top realtors in Texas, the story of the top faith journalist in the country, and more.
Currently, the plan is to release one episode every other week. But I reserve the right to increase or even decrease that.
One important note: You will not have to pay for any episode of “That Was Stupid.” It is free here, as well as on all major podcast platforms. However, if you’d like to watch the video version of the podcast, that will only be available to paid supporters here on Substack. I’ll embed it at the bottom of each episode post.
As always, you’ll get notified whenever a new episode is posted. However, if you ever want to check if you missed an episode or go back and listen to a previous one, just go to this page. In fact, go catch up on old episodes before the new season starts later this week!
Excited to have you join us for “That Was Stupid.” Welcome!
— Jon
P.S. If you’re wondering about why I title the episodes like I do, it’s because if it works for one of the best comedies of all time, I thought it would work for me. 🤷♂️
Paying supporters, watch the video version by clicking play on the image below:
The one where we're back!