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Home 15 Regrets from 15 Years of Professional Podcasting [episode 394]
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15 Regrets from 15 Years of Professional Podcasting [episode 394]

Team EntertainerBy Team EntertainerJune 18, 2025Updated:June 20, 2025No Comments19 Mins Read
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15 Regrets from 15 Years of Professional Podcasting [episode 394]
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As The Audacity to Podcast celebrates 15 years {of professional} podcasting, I invite you to take a essential look again on the largest errors I’ve made and issues I want I did in another way with my present. My hope is that this may encourage you to both repair this stuff early for your self, or keep away from them altogether!

Although I revealed the primary episode of The Audacity to Podcast 15 years in the past on June 17, 2010, I’ve truly been podcasting longer than that. I revealed my first-ever episode in April 2007. However I take into account The Audacity to Podcast to be after I actually took podcasting severely and even “professionally.”

Apart from the primary and final objects on this listing, the next regrets in no different explicit order. To maintain this episode “shorter,” I am going to let you determine learn how to apply every of those your self, however please let me know if you would like extra details about any of those in a future episode!

Remorse #1: Hiatuses

That is my largest remorse about my podcast: the embarrassingly lengthy hiatuses I’ve taken. It began in late 2017 after I all of the sudden disappeared attributable to a devastating household emergency. And the lengthy occasions away since then have been a number of shockwaves from having my world turned the wrong way up.

However this is what’s troublesome to admit: I may have returned to the mic sooner if not for my very own “head junk.” It was a mixture of “imposter syndrome,” self-doubt, pointless distractions, some stage of “perfectionism,” self-criticism, and even some worry and laziness.

It value me lots of alternatives, viewers, affect, authority, and even revenue.

And though I point out revenue, please hear me clearly that I’m not bringing again The Audacity to Podcast for cash. As a substitute, I am lastly taking the steps towards my adverse “head junk” and stepping again right into a burning ardour to proceed educating and provoking you!

Remorse #2: Not constructing an e-mail listing sooner

You most likely hear this one so usually from entrepreneurs that you just’re sick of it.

However e-mail lists aren’t just for entrepreneurs!

Even in case you podcast just for the enjoyable of it, there are many nice methods you need to use an e-mail listing regardless of why you are podcasting! For instance, you need to use an e-mail listing to supply actionable data out of your podcast episodes to your viewers, get extra private along with your viewers, solicit suggestions you may share in your podcast, get to know your viewers, and—sure—even promote issues to your viewers.

Remorse #3: Not selling my episodes by way of e-mail

Talking of e-mail, I truly suggest towards utilizing an e-mail listing solely to advertise your newest episodes. However my remorse is that I did not promote my newest episodes in my emails in any respect! I usually take into consideration creating an extra e-mail listing solely for the sake of offering my full notes and hyperlinks to you so you may simply take motion on something even after you delete the podcast episode out of your podcast app. However I’ve not even been good at merely together with an auto-updating widget in any of my emails—nothing from my e-mail listing or private emails. Granted, a part of it is because my e-mail service supplier, ActiveCampaign, used an outdated RSS validator that might choke on legitimate podcast RSS feeds—not less than the final time I examined it.

I truly nonetheless have not corrected this, both. However please let me know in case you could be concerned about receiving my episode notes by way of e-mail robotically after I publish my episodes!

Remorse #4: Pursuing the flawed enterprise

I began The Audacity to Podcast in 2010 whereas I used to be nonetheless full-time employed. The job I had was my dream job, however I burned out (largely attributable to some unhealthy selections on my half). I used to be searching for an exit and was particularly concerned about working my very own enterprise, however did not see how I may develop a enterprise till after I had launched The Audacity to Podcast.

However I nonetheless had the flawed enterprise in thoughts!

As a result of I used to be a web-designer in my job at the moment, and I loved designing web sites, I assumed, “Podcasters want web sites, and I will be the man to make them!” However I severely misjudged the market, particularly since there weren’t many individuals who wished to pay for the utterly customized design service I used to be providing.

After I had my final web-design shopper just a few years after beginning my enterprise, I actually did not need a web-design shopper. So I quoted them a extremely excessive worth that might make it value my time—and dang it they accepted that quote with none negotiation!

I dragged my toes on that challenge as a result of my coronary heart wasn’t in that form of work anymore. They finally fired me, and it even damage a friendship at the moment. However after I acquired that e-mail telling me I used to be fired, I used to be truly relieved! And that is after I realized I could not design web sites for different individuals anymore. And I feel it was shortly after that narrowing of my focus that my enterprise began rising significantly better—the proper enterprise for me!

Remorse #5: Not creating sufficient coaching merchandise

Even after I spotted the appropriate enterprise for me, I nonetheless did not leverage it sufficient! I ought to have created extra digital merchandise like programs, ebooks, group teaching, and extra. However I did not. And to at the present time, I nonetheless do not have my very own “learn how to podcast” course, which is one thing I nonetheless very a lot need to create!

However the programs I did create—Search engine optimisation for Podcasters (which was the first-ever podcast-Search engine optimisation coaching!) and Zoom H6 for Podcasters—had been each very properly acquired and I am nonetheless very pleased with their manufacturing high quality (though I not promote my Search engine optimisation course as a result of about one third of it’s outdated). Nonetheless, I may have and may have created far more!

Remorse #6: Ready too lengthy to register my trademark

I’ve claimed and defended “The Audacity to Podcast” as my very own trademark for a few years and indicated that with the unregistered trademark image (™). And after greater than 10 years of use, I lastly determined to rent my pal Gordon Firemark as my enterprise lawyer and to assist me formally register the trademark. However after 10 years of unique use, we found somebody filed for a very related trademark just a few months earlier than we did! And positive sufficient, our two filings had been too related for the USA Patent and Trademark Workplace (USPTO) to grant each logos.

In order that started a pricey course of. The opposite social gathering’s trademark was truly not excellent, and I provided them recommendations and even free consulting so they may not solely have a greater trademark, however a greater launch and enterprise over all. However they would not budge. Then my lawyer provided an “settlement to coexist,” which might permit us to each have our registered logos with the understanding that we would not sue one another, however they would not reply to that. I even tried to softly level out to them a number of occasions that if we needed to go to court docket over it, it will be costly and I would win as a result of I had 10 years of utilization already (that they had nothing however a short lived web site).

Lastly, after almost 4 years, their web site disappeared and so they stopped renewing their trademark submitting, which allowed my very own to undergo! And in January 2025, The Audacity to Podcast® was lastly a registered trademark!

Fortunately, I did not have any of this hassle after I registered the trademark for Podgagement®. I did that earlier than I even introduced the brand new title, and that phrase did not exist on the Web earlier than I coined it.

So if I may return into the previous, I’d have registered The Audacity to Podcast as quickly as I had the cash to do it or knew it will be a serious a part of my enterprise.

Remorse #7: Making an attempt to do issues cheaply

And talking of cash, making an attempt to do lots of podcasting issues cheaply or free truly value me so much. I keep in mind one time losing a number of hours—perhaps even a few days—making an attempt to determine a course of to power my MacBook Professional to 1,280 × 720 high-DPI decision (for recording my display on the excellent high quality and dimension) as a result of I did not need to spend $4 on an app that made it a 2-click course of.

There have been different issues I spent hours hacking collectively to do what I wished as a result of I did not need to spend the cash for the answer.

However my options had been not truly low cost or free! Like most “free” issues, they value me time and data (perhaps even mind cells and graying my hair—if I had any left!).

I feel ID3 Editor was my first buy (for under $15) that made me notice how significantly better my workflow could possibly be by investing the place I wanted.

Sure, typically, the issues I would like had been just too costly and so I needed to be resourceful. However I’ve additionally realized that typically it is value investing in one thing that can save me a complete lot of time or do issues higher than I may do them myself. (That is an enormous purpose so many podcasters use Podgagement—it saves you greater than 11 million mouse clicks daily!)

Remorse #8: Not publishing extra by means of different channels (together with video)

I am not touching the “video podcast” debate proper now. However I positively remorse not publishing extra content material—unique or repurposed—in lots of locations.

One of many issues that held me again was a “put it aside for the podcast” mentality that I felt like all new content material concepts I had needs to be shared first (or perhaps even uniquely) in my podcast. Or I used to be pondering, “I can not do that matter justice by overlaying it in solely a few minutes. I higher simply do a complete episode about it.”

One other factor that held me again was my obsession with excellence. I simply could not stand publishing a video with out good lighting and nice audio. (It is now a entire lot simpler to get each of these with trendy smartphones, particularly with superb and inexpensive little mics just like the Hollyland Lark M2S!)

And there was (and nonetheless is a few) disdain for the way some platforms work. For instance, I nonetheless abhor how TikTok mirrors video recorded into it, and I hated what number of platforms would allow you to report for under seconds at a time, requiring numerous stops and begins or disjointed phrases. And, after all, I hated vertical video.

However I look again in any respect the P.R.O.F.I.T. (reputation, relationships, alternatives, enjoyable, revenue, or tangibles) I missed by not publishing in additional locations!

Remorse #9: Not reaching out to the press about important issues

I dwell close to Cincinnati and I’ve gotten press solely as soon as—and it wasn’t even for my very own accomplishments! I used to be featured in The Cincinnati Enterprise Courier and on native TV speaking about podcasting as a result of Worldwide Podcast Day was arising (I am one of many cofounders and organizers).

However I did not attempt for any protection when a number of of my podcasts had been nominated for awards. I did not attempt for any protection each occasions The Audacity to Podcast gained the Individuals’s Selection Podcast Awards. I did attempt for protection after I was inducted into the Podcast Corridor of Fame, however I did not attempt exhausting sufficient and I did not get any protection. I remorse not being extra proactive about this stuff after they was most well timed!

Remorse #10: Accepting sponsors

Do you know that I had some sponsors a few years in the past? I accepted them as a result of I noticed the revenue potential (which wasn’t a lot, however I used to be form of determined for revenue again then!). However now I remorse it as a result of I ought to have targeted extra on creating and promoting my very own stuff, which might have been far more worthwhile.

I am not saying I am going to by no means once more have sponsors on The Audacity to Podcast, however these previous sponsors weren’t even podcasting-related!

For a few years, I’ve mentioned that I truly cannot afford to have sponsors on my podcast. The associated fee is simply too excessive! Actually, I’d moderately learn out reward notes from you than getting paid to advertise another enterprise! (So if you would like to assist what I do, click on right here to present again no matter you are feeling The Audacity to Podcast is value to you!)

Remorse #11: Not creating “value4value” alternatives for my viewers

And going proper together with this, I remorse not embracing “value4value” (or “v4v”) philosophy years in the past. That is not a Bitcoin factor and it isn’t even a Podcasting 2.0 factor! As a substitute, it is a philosophy that goes like this: I am providing you with worth by means of my podcast—training, leisure, inspiration, and such—and I can present alternatives so that you can take into account what that’s value to you in an effort to give a few of that worth again. You are giving worth again for the worth I offer you, or you possibly can say that I offer you one thing of worth for the worth you will give me for it. That is why it is referred to as “worth for worth”—coined by the man who invented podcasting, Adam Curry (the Podfather).

I did value4value on my different podcasts, however my massive purpose for not together with it on The Audacity to Podcast is that I at all times felt it will undermine my enterprise, as a result of I’ve precise issues to promote.

Nevertheless it took the Podcasting 2.0 revolution for me to comprehend the reality value of value4value: group, relationships, and reciprocity. That is why I now (after I keep in mind to) promote methods you can assist the worth I offer you by means of The Audacity to Podcast by giving again any quantity you are feeling the podcast is value and I additionally settle for Podcasting 2.0 funds by means of Bitcoin by way of a contemporary Podcasting 2.0 podcast app.

Remorse #12: Working solo for too lengthy

I very a lot have the “superhero syndrome” Chris Ducker described in his ebook Digital Freedom. I wished to do every little thing in my enterprise. And to put aside modesty for a second, I used to be fairly good at most of it!

Nevertheless it took me some time to find I may purchase again my time (the title of one other ebook I like to recommend on this matter, Purchase Again Your Time, by Dan Martell) to pay another person to do issues I could not or should not do. Actually, it was Digital Freedom that impressed me sufficient to lastly rent another person to construct the My Podcast Critiques service for me. And now I rebuilt that into Podgagement, probably the most invaluable factor my enterprise sells proper now.

I additionally found the liberty it introduced after I employed a podcast-editor and my first private assistant in my enterprise. Earlier than this stuff, I used to be positively working solo for too lengthy! Whereas I used to be getting ready this episode and with out his even realizing what this episode was going to be about, my podcast-editor John Bukenas coined the time period entrepodneur:

An individual who independently produces each facet of their podcast from begin to end—recording, modifying, selling, reserving friends, importing, and managing the present—with none exterior assist.

Please present my editor some love by upvoting his entry in City Dictionary!

Remorse #13: Utilizing a cute (and costly) area

I do not precisely remorse the title The Audacity to Podcast (or not less than not very a lot), particularly now that it is my registered trademark. However I do remorse the area I acquired for the podcast community I launched on the similar time I launched The Audacity to Podcast (and I used to be internet hosting 3 of my very own reveals at the moment). These had been all related as a part of my skilled podcasting technique. I went for a “cute” area as a result of I noticed individuals utilizing .television, .ly, or having actually inventive stuff just like the webpage bookmark service Scrumptious with the area del.icio.us.

Sadly, the “cute” area I had in thoughts was costly. And since I hate letting domains go that I’ve ever publicly shared, I’ve to pay that area’s costly renewal charge yearly for the remainder of my life!

A number of years after I already began the community, I spotted a less expensive and much more comprehensible area. I switched to that I feel just one 12 months earlier than retiring the community!

Bitly is one other instance of this. Their area was bit.ly, nevertheless it’s now merely bitly.com.

Remorse #14: Getting concerned with the flawed individuals

I am not going to call anybody right here, however I’ve gotten concerned with some unhealthy individuals previously and it turned out to value me dearly in my skilled and podcasting endeavors. I am nonetheless struggling repercussions from a few of them. I want that I had by no means pursued these issues that I thought had been nice alternatives, though I did have issues, as a result of my issues ended up being confirmed true.

And what actually frustrates me about my errors is that when issues began crashing down, I took them manner too personally and failed to face up as sturdy as I ought to have and combat for the appropriate issues.

Classes realized. “By no means go in towards a Sicilian when demise is on the road!”

Remorse #15: Not focusing extra on relationships

And on the flip aspect is my earlier remorse, however definitely not least. I want I had targeted extra on relationships with individuals.

Whereas this definitely has heavy ramifications exterior of podcasting (and I would do an episode about that sometime sooner or later), I’m referring strictly to my skilled and podcasting pursuits. Whereas I see others constructing a bunch of relationships, I’ve usually spent extra time on the content material than on the individuals. Like with The Audacity to Podcast, you have not often heard me discuss my life or share private issues that show you how to get to know me—except they by some means completely relate to the topic at hand. The primary purpose for that’s that I’ve this concept caught in my thoughts that you just’re not right here for me—I may even say you do not “care” about me—however you are right here for what I educate. And so I self-filter out lots of stuff as a result of I need to provide the content material I promise to present you: podcasting training and inspiration.

However regardless of that, I nonetheless keep in mind what number of women and men had been there for me just a few years in the past after I went by means of a really troublesome time in my life. Numerous individuals prayed for me and with me, despatched me notes of encouragement, checked in with me, and extra. I particularly keep in mind a Podcast Motion I attended whereas my emotional wounds had been nonetheless bleeding. Mark Deal, from Atlanta, made it a degree to present me a hug daily of the convention, and that meant so much to me! However I did not study till later that he is truly not a hugger, however he knew I would like these hugs! And Emily Prokop despatched me encouraging voicemails and was the one particular person to make me cry at that convention—merely due to her heat kindness and compassion.

(And aspect notice as one other a part of this: I even debated naming these individuals—however I can not even clarify why that was a debate!)

And I’ve misplaced loads of relationships over time, particularly these previous few years. A few of these are my fault, some are the faults of the others regardless of my makes an attempt at friendship, and a few are from misunderstandings and false judgments.


So there you have got it. 15 regrets from 15 years {of professional} podcasting by means of The Audacity to Podcast. I hope that you may study—and even snigger—at my errors so that you just will not make the identical ones. As a result of in every little thing I do by means of my podcast, I need to— what’s coming!—provide the guts and educate you the instruments so you can begin and develop your individual podcast for ardour and PROFIT!

Should you’ve been with me by means of the troublesome occasions and even because the starting, THANK YOU!

Supercharge your podcast engagement and develop your podcast!

Do you ever really feel like your podcast is caught? Such as you’re pouring your coronary heart into your podcast nevertheless it looks as if nobody is listening?

Strive Podgagement that will help you supercharge your podcast endgagement!

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Ask your questions or share your suggestions

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Disclosure

This put up could comprise hyperlinks to services or products with which I’ve an affiliate relationship. I’ll obtain compensation out of your actions by means of such hyperlinks. Nonetheless, I do not let that corrupt my perspective and I do not suggest solely associates.



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