Adventures In Podcasting


Starting something new is always scary but with podcasting it’s more exciting than anything else.  Now, maybe that’s because I’ve been doing radio for almost 30 years and the similarities are uncanny. But the digital wild west has plenty of land to offer us all.  In this blog post I’ll tell you some of what I’ve learned in the short 3 months of doing The Bailey Show Podcast.

Before being fired in October 2021 I was already dabbling in podcasting with a free one day a week episode called Bailey’s Black Cloud Podcast. It’s a short 30 minute listen of this “black cloud” that follows me. The idea has been known to my audience for sometime so the podcast form turned out to be successful in a small dose.

The idea all along was to create a network of sorts offering different content everyday of the week. The blueprint was to have this done in 3 months in which me and my team were able to accomplish.  This way we can offer sponsors and most importantly the audience something new on demand 7 days a week on different platforms that include audio and video.  So far, this blueprint seems to be working.

It’s funny, the everyday struggles with corporate radio just aren’t there with podcasting if you have all of the tools to succeed. One’s endless creativity can do anything without having any mental restrictions of “will it work” or “is it PPM (radio’s rating structure) friendly.”  I have a studio, 2 employees, a built-in audience from my radio career, endless old audio and a relaxed working environment to produce great content.  So far so good, right?

Yeah, it’s good but of course money is always an issue. We’ve taken the “Facebook / Social Network” approach. Let’s make it “cool” or a “thing” and the rest will follow.  And, so far, that has seemed to work.  Our sponsors seem to want to be a part of the process and because of the direct “ear-to-brain” demand the sponsors are getting a return on investment.  

Now, there are struggles with being one of many podcasters in the world. Especially one without millions of downloads or plays.  We currently sit at just under 200,000 downloads / plays in 3 months. Not bad, but no Joe Rogan, yet. 

The struggle is, you’re just another podcaster.  Booking big guests can be a struggle unless you have a relationship or connection with the guest.  One of the things I disliked about radio was the guests booked on my shows. It’s a double edged sword. One, guests can be good for shows especially if you’re a good interviewer. I consider myself a good interviewer.  Two, guests can be bad because you usually talk about nothing of interest to the audience.  You get that 8-10 minute of time to talk about some show that airs strictly on an app that no one has. Even the best interviewers in the world would struggle with those parameters.  

For podcasting I’ve found that the guest process is much more interesting. I can get into the good stuff with the guest and for as long or short as I want.  The podcaster makes the rules.  I’ve seen that guests open up more and are way more relaxed doing podcast interviews.  

This might be my favorite thing about podcasting so far.  Podcasters seem to want to help one another.  Radio, not so much. I absolutely love the comradery that exists in the digital space.  Also, the audience is much more cult-like in podcasting. I’ve seen this before at a station I worked at in Orlando, FL (Real Radio 104.1). The audience there had that do-or-die mentality.   I’m seeing that in the podcasting space.  What did “the Kid” say, “You got 3 or 4 good pals then you have a tribe and there ain’t nothing stronger than that?” Yes, that’s a Young Guns quote. 

There are very few things that I dislike in the podcasting world.  I love challenges and this a challenge not only for the radio veteran starting something new in a new world but for any podcaster that wants the creative freedom to reach an audience with their content.

So, what does the future hold?  Who knows? For me, I’m sure I’ll go back to corporate radio at some point if the opportunity is right. But, to always have the podcast, will and can create a constant for content distribution. That I really, really like.  There are 750,000 active podcasts (Edison Research) out there. Can you imagine just getting 2% of that audience?  The possibilities are endless!

In radio there is a term, “being bit by the bug.”  In Orlando, FL, 1995, my first day in a radio station I was, “bit by the bug.”  Fast-forward, I’m once again being, “bit by the bug.”  

I can say that so far this adventure has been liberating and exciting.  I wish you nothing but the best as we all saddle up to place our flags on our new digital land.  YeeeHawww!


Jason Bailey 

Host /Creator / The Bailey Show Podcast

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4 Comments. Leave new

  • Jose Rodriguez
    January 24, 2022 6:32 pm

    Good Day Sir!

    Do you have a target audience for your show? I’m talking about demographics, age groups, race, etc…

    the reason I asked is because my boy age 13 [he will be 14 in February] would like to participate in Smarta Marta, he’s been listening to the Radio program for the Game shows part of the radio on his way to school, now he listens to the Podcast and he would like to participate, let us know if the possibility exists if not that’s cool!

    Thank you

    kindly reply to my email

  • It’s a dog eat dog world out there. I have about 15 podcast shows in my library ( yours included). I look for “ contents”. You’re new and doing good for being new to the game. Do you listen to other podcast ( like “ Smartless”, or “The Steam Room” with Ernie Johnson & Charles Barkley?

    Best wishes b

  • Tara Ferguson
    January 26, 2022 3:13 am

    Looking forward to how this all goes!! A 2% from the start- you are a great host and you have a great tribe with you! I have never followed a radio personality before like I have you and your tribe. You are very relatable and fun to listen to.

  • Dude, this was a good read. Keep posting!


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