As The Audacity to Podcast celebrates 15 years of professional podcasting, I invite you to take a critical look back at the biggest mistakes I've made and things I wish I did differently with my show. My hope is that this will inspire you to either fix these things early for yourself, or avoid them altogether!

Even though I published the first episode of The Audacity to Podcast 15 years ago on June 17, 2010, I've actually been podcasting longer than that. I published my first-ever episode in April 2007. But I consider The Audacity to Podcast to be when I really took podcasting seriously and even “professionally.”

Besides the first and last items on this list, the following regrets in no other particular order. To keep this episode “shorter,” I'll let you figure out how to apply each of these yourself, but please let me know if you'd like more information about any of these in a future episode!

Regret #1: Hiatuses

This is my biggest regret about my podcast: the embarrassingly long hiatuses I've taken. It started in late 2017 when I suddenly disappeared due to a devastating family emergency. And the long times away since then have been multiple shockwaves from having my world turned upside down.

But here's what's difficult to confess: I could have returned to the mic sooner if not for my own “head junk.” It was a mix of “imposter syndrome,” self-doubt, unnecessary distractions, some level of “perfectionism,” self-criticism, and even some fear and laziness.

It cost me a lot of opportunities, audience, influence, authority, and even income.

And even though I mention income, please hear me clearly that I am not bringing back The Audacity to Podcast for money. Instead, I'm finally taking the steps against my negative “head junk” and stepping back into a burning passion to continue educating and inspiring you!

Regret #2: Not building an email list sooner

You probably hear this one so often from entrepreneurs that you're sick of it.

But email lists aren't only for marketers!

Even if you podcast only for the fun of it, there are plenty of great ways you can use an email list no matter why you're podcasting! For example, you can use an email list to provide actionable information from your podcast episodes to your audience, get more personal with your audience, solicit feedback you can share in your podcast, get to know your audience, and—yes—even promote things to your audience.

Regret #3: Not promoting my episodes via email

Speaking of email, I actually recommend against using an email list only to promote your latest episodes. But my regret is that I didn't promote my latest episodes in my emails at all! I often think about creating an additional email list solely for the sake of providing my full notes and links to you so you can easily take action on anything even after you delete the podcast episode from your podcast app. But I've not even been good at simply including an auto-updating widget in any of my emails—nothing from my email list or personal emails. Granted, part of this is because my email service provider, ActiveCampaign, used an outdated RSS validator that would choke on valid podcast RSS feeds—at least the last time I tested it.

I actually still haven't corrected this, either. But please let me know if you would be interested in receiving my episode notes via email automatically after I publish my episodes!

Regret #4: Pursuing the wrong business

I started The Audacity to Podcast in 2010 while I was still full-time employed. The job I had was my dream job, but I burned out (largely due to some bad choices on my part). I was looking for an exit and was especially interested in running my own business, but didn't see how I could grow a business until after I had launched The Audacity to Podcast.

But I still had the wrong business in mind!

Because I was a web-designer in my job at that time, and I enjoyed designing websites, I thought, “Podcasters need websites, and I'll be the guy to make them!” But I seriously misjudged the market, especially since there weren't many people who wanted to pay for the completely custom design service I was offering.

When I had my last web-design client a few years after starting my business, I really didn't want a web-design client. So I quoted them a really high price that would make it worth my time—and dang it they accepted that quote without any negotiation!

I dragged my feet on that project because my heart wasn't in that kind of work anymore. They eventually fired me, and it even hurt a friendship at that time. But when I got that email telling me I was fired, I was actually relieved! And that's when I realized I couldn't design websites for other people anymore. And I think it was shortly after that narrowing of my focus that my business started growing much better—the right business for me!

Regret #5: Not creating enough training products

Even after I realized the right business for me, I still didn't leverage it enough! I should have created more digital products like courses, ebooks, group coaching, and more. But I didn't. And to this day, I still don't have my own “how to podcast” course, which is something I still very much want to create!

But the courses I did create—SEO for Podcasters (which was the first-ever podcast-SEO training!) and Zoom H6 for Podcasters—were both very well received and I'm still very happy with their production quality (even though I no longer promote my SEO course because about one third of it is outdated). Nonetheless, I could have and should have created much more!

Regret #6: Waiting too long to register my trademark

I've claimed and defended “The Audacity to Podcast” as my own trademark for many years and indicated that with the unregistered trademark symbol (™). And after more than 10 years of use, I finally decided to hire my friend Gordon Firemark as my business lawyer and to help me officially register the trademark. But after 10 years of exclusive use, we discovered someone filed for a very similar trademark only a few months before we did! And sure enough, our two filings were too similar for the United States Patent and Trademark Office (USPTO) to grant both trademarks.

So that began a costly process. The other party's trademark was actually not very good, and I offered them suggestions and even free consulting so they could not only have a better trademark, but a better launch and business over all. But they wouldn't budge. Then my lawyer offered an “agreement to coexist,” which would allow us to both have our registered trademarks with the understanding that we wouldn't sue each other, but they wouldn't respond to that. I even tried to gently point out to them several times that if we had to go to court over it, it would be expensive and I would win because I had 10 years of usage already (they had nothing but a temporary website).

Finally, after nearly 4 years, their website disappeared and they stopped renewing their trademark filing, which allowed my own to go through! And in January 2025, The Audacity to Podcast® was finally a registered trademark!

Thankfully, I didn't have any of this trouble when I registered the trademark for Podgagement®. I did that before I even announced the new name, and that word didn't exist on the Internet before I coined it.

So if I could go back into the past, I would have registered The Audacity to Podcast as soon as I had the money to do it or knew it would be a major part of my business.

Regret #7: Trying to do things cheaply

And speaking of money, trying to do a lot of podcasting things cheaply or free actually cost me a lot. I remember one time wasting several hours—maybe even a couple of days—trying to figure out a process to force my MacBook Pro to 1,280 × 720 high-DPI resolution (for recording my screen at the perfect quality and size) because I didn't want to spend $4 on an app that made it a 2-click process.

There were other things I spent hours hacking together to do what I wanted because I didn't want to spend the money for the solution.

But my solutions were not actually cheap or free! Like most “free” things, they cost me time and knowledge (maybe even brain cells and graying my hair—if I had any left!).

I think ID3 Editor was my first purchase (for only $15) that made me realize how much better my workflow could be by investing where I needed.

Yes, sometimes, the things I need were simply too expensive and so I had to be resourceful. But I've also learned that sometimes it's worth investing in something that will save me a whole lot of time or do things better than I could do them myself. (That's a big reason so many podcasters use Podgagement—it saves you more than 11 million mouse clicks every day!)

Regret #8: Not publishing more through other channels (including video)

I'm not touching the “video podcast” debate right now. But I definitely regret not publishing more content—original or repurposed—in many places.

One of the things that held me back was a “save it for the podcast” mentality that I felt like any new content ideas I had should be shared first (or maybe even exclusively) in my podcast. Or I was thinking, “I can't do this topic justice by covering it in only a couple of minutes. I better just do a whole episode about it.”

Another thing that held me back was my obsession with excellence. I just couldn't stand publishing a video without good lighting and great audio. (It's now a whole lot easier to get both of those with modern smartphones, especially with amazing and affordable little mics like the Hollyland Lark M2S!)

And there was (and still is some) disdain for how some platforms work. For example, I still abhor how TikTok mirrors video recorded into it, and I hated how many platforms would let you record for only seconds at a time, requiring lots of stops and starts or disjointed phrases. And, of course, I hated vertical video.

But I look back at all the P.R.O.F.I.T. (popularity, relationships, opportunities, fun, income, or tangibles) I missed by not publishing in more places!

Regret #9: Not reaching out to the press about significant things

I live near Cincinnati and I've gotten press only once—and it wasn't even for my own accomplishments! I was featured in The Cincinnati Business Courier and on local TV talking about podcasting because International Podcast Day was coming up (I'm one of the cofounders and organizers).

But I didn't try for any coverage when several of my podcasts were nominated for awards. I didn't try for any coverage both times The Audacity to Podcast won the People's Choice Podcast Awards. I did try for coverage when I was inducted into the Podcast Hall of Fame, but I didn't try hard enough and I didn't get any coverage. I regret not being more proactive about these things when they was most timely!

Regret #10: Accepting sponsors

Did you know that I had some sponsors many years ago? I accepted them because I saw the income potential (which wasn't much, but I was kind of desperate for income back then!). But now I regret it because I should have focused more on creating and selling my own stuff, which would have been much more profitable.

I'm not saying I'll never again have sponsors on The Audacity to Podcast, but those past sponsors weren't even podcasting-related!

For many years, I've said that I actually can't afford to have sponsors on my podcast. The cost is too high! In fact, I would rather read out gift notes from you than getting paid to promote some other business! (So if you'd like to support what I do, click here to give back whatever you feel The Audacity to Podcast is worth to you!)

Regret #11: Not creating “value4value” opportunities for my audience

And going right along with this, I regret not embracing “value4value” (or “v4v”) philosophy years ago. This is not a Bitcoin thing and it's not even a Podcasting 2.0 thing! Instead, it's a philosophy that goes like this: I'm giving you value through my podcast—education, entertainment, inspiration, and such—and I can provide opportunities for you to consider what that is worth to you so that you can give some of that value back. You're giving value back for the value I give you, or you could say that I give you something of value for the value you'll give me for it. That's why it's called “value for value”—coined by the guy who invented podcasting, Adam Curry (the Podfather).

I did value4value on my other podcasts, but my big reason for not including it on The Audacity to Podcast is that I always felt it would undermine my business, because I have actual things to sell.

But it took the Podcasting 2.0 revolution for me to realize the truth worth of value4value: community, relationships, and reciprocity. That's why I now (when I remember to) promote ways you can support the value I give you through The Audacity to Podcast by giving back any amount you feel the podcast is worth and I also accept Podcasting 2.0 payments through Bitcoin via a modern Podcasting 2.0 podcast app.

Regret #12: Working solo for too long

I very much have the “superhero syndrome” Chris Ducker described in his book Virtual Freedom. I wanted to do everything in my business. And to set aside modesty for a moment, I was pretty good at most of it!

But it took me a while to discover I could buy back my time (the name of another book I recommend on this topic, Buy Back Your Time, by Dan Martell) to pay someone else to do things I couldn't or shouldn't do. In fact, it was Virtual Freedom that inspired me enough to finally hire someone else to build the My Podcast Reviews service for me. And now I rebuilt that into Podgagement, the most valuable thing my business sells right now.

I also discovered the freedom it brought when I hired a podcast-editor and my first personal assistant in my business. Before these things, I was definitely working solo for too long! While I was preparing this episode and without his even knowing what this episode was going to be about, my podcast-editor John Bukenas coined the term entrepodneur:

A person who independently produces every aspect of their podcast from start to finish—recording, editing, promoting, booking guests, uploading, and managing the show—without any outside help.

Please show my editor some love by upvoting his entry in Urban Dictionary!

Regret #13: Using a cute (and expensive) domain

I don't exactly regret the name The Audacity to Podcast (or at least not very much), especially now that it's my registered trademark. But I do regret the domain I got for the podcast network I launched at the same time I launched The Audacity to Podcast (and I was hosting 3 of my own shows at that time). These were all connected as part of my professional podcasting strategy. I went for a “cute” domain because I saw people using .tv, .ly, or having really creative stuff like the webpage bookmark service Delicious with the domain del.icio.us.

Unfortunately, the “cute” domain I had in mind was expensive. And since I hate letting domains go that I've ever publicly shared, I have to pay that domain's expensive renewal fee every year for the rest of my life!

Several years after I already started the network, I realized a much cheaper and even more understandable domain. I switched to that I think only 1 year before retiring the network!

Bitly is another example of this. Their domain used to be bit.ly, but it's now simply bitly.com.

Regret #14: Getting involved with the wrong people

I'm not going to name anyone here, but I've gotten involved with some bad people in the past and it turned out to cost me dearly in my professional and podcasting endeavors. I'm still suffering repercussions from some of them. I wish that I had never pursued those things that I thought were great opportunities, even though I did have concerns, because my concerns ended up being proven true.

And what really frustrates me about my mistakes is that when things started crashing down, I took them way too personally and failed to stand up as strong as I should have and fight for the right things.

Lessons learned. “Never go in against a Sicilian when death is on the line!”

Regret #15: Not focusing more on relationships

And on the flip side is my previous regret, but certainly not least. I wish I had focused more on relationships with people.

While this certainly has heavy ramifications outside of podcasting (and I might do an episode about that someday in the future), I am referring strictly to my professional and podcasting pursuits. While I see others building a bunch of relationships, I've often spent more time on the content than on the people. Like with The Audacity to Podcast, you've rarely heard me talk about my life or share personal things that help you get to know me—unless they somehow totally relate to the subject at hand. The main reason for that is that I have this idea stuck in my mind that you're not here for me—I could even say you don't “care” about me—but you're here for what I teach. And so I self-filter out a lot of stuff because I want to give you the content I promise to give you: podcasting education and inspiration.

But despite that, I still remember how many men and women were there for me a few years ago when I went through a very difficult time in my life. Countless people prayed for me and with me, sent me notes of encouragement, checked in with me, and more. I especially remember a Podcast Movement I attended while my emotional wounds were still bleeding. Mark Deal, from Atlanta, made it a point to give me a hug every day of the conference, and that meant a lot to me! But I didn't learn until later that he's actually not a hugger, but he knew I need those hugs! And Emily Prokop sent me encouraging voicemails and was the only person to make me cry at that conference—simply because of her warm kindness and compassion.

(And side note as another part of this: I even debated naming these people—but I can't even explain why that was a debate!)

And I've lost plenty of relationships over the years, especially these past few years. Some of those are my fault, some are the faults of the others despite my attempts at friendship, and some are from misunderstandings and false judgments.

So there you have it. 15 regrets from 15 years of professional podcasting through The Audacity to Podcast. I hope that you can learn—and even laugh—at my mistakes so that you won't make the same ones. Because in everything I do through my podcast, I want to—you know what's coming!—give you the guts and teach you the tools so you can start and grow your own podcast for passion and PROFIT!

If you've been with me through the difficult times and even since the beginning, THANK YOU!

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Disclosure

This post may contain links to products or services with which I have an affiliate relationship. I may receive compensation from your actions through such links. However, I don't let that corrupt my perspective and I don't recommend only affiliates.