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May 16, 2026

Sometimes You're the Windshield

Time for a Pep Talk

This newsletter contains affiliate links. Not all of them, but some of them. I earn a small commission, and it doesn’t cost you anything. I call that a win-win.

I’m not looking for a pity party, but this is a pep talk to anyone who ever made a decision you wish you hadn’t. After going to the Podcast Show in London (on Libsyn’s dime) I didn’t go back after leaving (and wished I had).

I made a plan and put money away for the trip. Things were looking good. Then I went downstairs and heard what sounded like someone peeing in my basement (which is weird when you live alone). What I found was this:

So as I saw water spewing into my basement I thought, “Well that looks expensive” (and seriously unhealthy). It turns out it was…

As I had just gotten out of debt for this first time in probably 40 years, I really didn’t want to go back in debt. So I thought I would empty my savings (including my Podcast show money) to pay for five guys with jack hammers digging to China from my basement.

So Where Did I Land?

Fast forward, I’m not going to the Podcast Show in London again, half my savings is gone, and I’m back in debt. It was very expensive (so thanks to all of you who support this newsletter financially I DEEPLY appreciate it). The fun part is I’m not done. Everything I get into needs replaced (windows, electric and more…).

It dawned on me today, that had a just put the trip on a card (as I’m back in debt anyway) I would be at one of the largest (if not THE largest) podcast shows making connections, planting seeds, that might eventually lead to opportunities to make money. I mean when you’re going back five figures in debt what’s another $3k?

You Do What You Can With What You Got

Life throws you curve balls. To quote the great philosopher Myley Cryus

There’s always gonna be another mountain

I’m always gonna wanna make it move

Always gonna be an uphill battle

Sometimes I’m gonna have to lose

Ain’t about how fast I get there

Ain’t about what’s waiting on the other side

It’s the climb

Yes, you get tired of climbing. But if you can’t enjoy the climb, you’re never going to make it.

Get a New Perspective

Another thing dawned on me. I got out of debt after divorce one. I got out of debt after divorce two. I know how to save money. As a child my family was once on welfare, so I know how to get by on what you need not what you want.

I’ve done this before, and I’ll do it again.

So if you made a decision about your podcast and looking back you think, “I should’ve zigged when I zagged” don’t look at it as a failure, but as a lesson. Got to college in the USA is ridiculously expensive (and I’ve got two degrees so I know of what I speak).

My second divorce was just about as expensive as my teaching degree from Akron University. I learned more from the divorce than I did in the classroom. Life is a classroom. Try to learn something every day.

They aren’t failures, if you lean from them, they are lessons to prepare you better for your future.


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Every month I ask my audience a question for the School of Podcasting. Here is this month’s question:

Let's talk remote recording. Many podcasters have made their way through more than one. So which one did you land on? Which ones did you pass on? Would you recommend your current tool to a new podcaster? I need your answer by May 22nd

Ready to Answer? Click Here

The Classics Never Get old

David Letterman joined Stephen Colbert to throw things off the root of the Ed Sullivan Theater (which Letterman invented years ago).

DesignCrowd for Graphics

This is not a new concept, but at DesignCrowd you put our a dollar amount you want to pay for artwork and such, and people enter their artwork, and you choose the one you feel is best, or use their built in tools to have your audience vote on their favorite. Check it out.

Macaulay Culkin Totally Blows an Opportunity to Promote His Podcast

So Macaulay Culkin is on the Ellen show, and they talk Home Alone and his other movies, but he’s out to promote his podcast Bunny Ears, and when she finally asks about it, he describes in such a way that I can’t see anyone saying, “Oh man I can’t wait to hear this!” (Click play, it will go to that spot). He made is 97 episodes.

Shortstack for Giveaways, Sweepstakes, etc

While shortstack does landing pages, forms, and popups, they came on my radar when looking into giveaways. If you’re brand new, you might be able to use their free plan which is less than 500 views of your item in a month (no credit card required). Prices start at $29 a month. Check it out.

What’s Coming In The Future

I interviewed Jordan from Buzzsprout about her podcast that she was able to monetize (when she is a team of one).


Need Help With Your Podcast?

Whether you’re just starting or a seasoned podcaster, the School of Podcasting can help. Helping podcasters is what I do, and I’ve been doing it since 2005

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