The Step-By-Step Breakdown to Succeed and then Fail at Podcasting

Failure is a feature of the creative process, not a bug. But that doesn’t make failure any easier to swallow.

You can read all the articles in the world about how you should “fail fast,” “fail often,” or “fail to learn.” But that doesn’t mean anyone’s excited to fail. No one goes into a project hoping that they’ll blow it.

But failure happens. And it happens a lot.

So rather than getting upset, I try to frame the act of publishing/releasing something (a blog post, a book, etc) a success, even if no one likes, shares, or buys). Because other people’s negativity or praise are external — I have no control over the response to my work. I can only control my input — how hard I work or how well I keep the promises I make to myself.

But when I don’t keep my promises, that’s failure. There’s no getting around it. And that kind of failure hurts. It hurts way worse than an errant mean tweet or a Facebook post that doesn’t garner a single like.

And that’s what this story is about.

A Kick Ass Idea (Is Only the Beginning)

I spent a lot of my free time in 2015 writing and publishing my book, Improv ABC. But even before the book was finished (as is often my habit), I was already daydreaming about my next project.

I was dead set on starting a podcast.

Some might call me a podcast fiend. I subscribe (and routinely listen) to 23 podcasts each week, adding new ones and removing stale ones depending on my mood and interest level. And listening to so many in a given week, I was getting tired of the trite (and easy) 45min interview formula.

I knew I could make something better (which is how most of my projects start). With narrative, storytelling podcasts like Freakonomics and 99% Invisible as inspiration, my girlfriend and I decided to start a podcast. Each week, we’d interview creative entrepreneurs in our community, and then, using the “improviser mindset” (taking risks and accepting failure) along with their advice, we’d attempt to do some aspect of their craft.

Using that same improviser mindset, I didn’t spend much time “planning.” I made a very quick “potential guest list” and got started.

I figured I’d find my footing along the way.

The original interview request…the podcast was now real

On September 9th, I emailed Randy Vines, the owner of a St. Louis themed apparel shop, STL Style, to request an interview. I thought he’d be a great first guest for several reasons:

  1. He and his co-owner/twin-brother Jeff are incredibly passionate and outspoken community advocates.
  2. I wanted an excuse to make a t-shirt.
  3. And I’m not gonna lie — they have a large audience of their own, which I hoped would help net us some early traction.

We scheduled the interview for October 6th — less than a month away.

In the Meantime…

I don’t do things halfway.

While I eagerly awaited the interview, I dove into podcasting head first.

I started compiling a master list of to-dos, like possible sponsors, things I wanted to try creating, people to contact, questions to ask, and more. I knew I had to at least be a little organized — it would have been silly to launch a weekly podcast without having a few episodes in the hopper.

It was also during this interim period that I stumbled upon a name for the podcast — This Won’t Kill You (TWKY). It was born from the idea that a lot of people don’t create new things out of fear…but the thing they’re afraid of is fear itself, not any actual harm that could come to them. I also did a little mission statement exercise (recommended by my Internet idol, Jason Zook) to get clear on my purpose and intentions.

This is what I wrote:


This Won’t Kill You is a podcast that helps listeners overcome their creative hurdles and take action on their ideas. In each episode, Ben and Julia will explore what it’s like to run a creative business (by interviewing creative professionals) Using the improviser mindset, they’ll try their hand at some aspect of that business. They’ll prove that it’s ok to take risks, even if you’re scared — because if you don’t try, you’ll never succeed beyond your wildest dreams.

A little cheesy. A little ambitious. But better than nothing!

(Squandered) Investment

Having done some “research” (which mostly consisted of reading thisawesome article about Ira Glass), I knew that I needed more than my iPhone and some moxie if I was going to make this seem halfway professional. So I made a few initial investments:

  • Yeti Microphone: $109.99
  • Branding: $150
  • Domain: $12

Total: $271.99

The podcast cover art designed by Rob Armbrister

I was planning to use Audacity (a free program) to record and edit the audio, and ultimately, I was going to create a Squarespace site (but I hadn’t yet paid for it when I abandoned the project).

The First (and Only) Episode

On October 6th, Julia and I met the Vines at their store on Cherokee. We snapped a few photos and started the tease the new project.

A little Instagram teaser posted on the day of the first interview

We recorded a 30 minute interview with the brothers as well as some video, which we were planning to use on a companion blog that would provide more detail about each episode.

That night, I transcribed the interview and noted some of my favorite moments. And before the week was out, I’d written a full script — including interview pieces we’d use and narration that Julia and I would read.

We both huddled under a blanket on our couch and, using our iPhone flashlights, recorded our speaking parts. Of course, we didn’t get it in a single take. We sounded like we were reading a script (which we were — next time I’d write bullet points rather than a full script). Three takes later, we called it “close enough.”

That week, I also started designing the t-shirt for the episode. We knew it had to be St. Louis themed (since STL Style sells t-shirts themed after popular St. Louis locations), and we decided to create one for Washington Avenue (aka Wash Ave), a downtown district known for nightlife. It has an iconic cobblestone street and lights that hang above it, which you can see in the design. We recorded our entire process (much more improvisationally) from coming up with the main idea, to creating the design, to how it turned out.

Top: Screenshot of some of the tshirts for sale on the STL Style website. Bottom: The t-shirt we designed for the STL Style episode. Not my greatest work, but hey, that’s what the podcast is about!

From Second Opinions…

As the first episode came together, it was time to get feedback from a small, inner circle. I wanted to hear the honest opinions from a few unbiased listeners to know how we could improve the podcast as we geared up to record the second episode.

You can give the STL Style episode a listen if you’re curious (although it’s missing an intro and outro)

I chose four friends — two girls and two guys — with varying levels of creative experience and creative self-confidence. I asked them all the same set of five questions:

  1. Was there a key takeaway you are going to apply to future creative projects?
  2. After listening, do you feel inspired to work on a creative project?
  3. On a scale of 1–5 (1 is bad, 5 is great), how would you describe the audio quality?
  4. How was the length? Too long? Too short? Just right?
  5. Is this something you’d want to listen to on a weekly basis?

Overall, we got some awesome feedback on our first episode:

“I honestly wanted more. I was really into this show. As a concept, and in practice. This is great.”

“The best takeaway in the podcast applies to just about everything I do– don’t overanalyze!”

And some very actionable advice on how to make Episode 2 even better:

“I think it sounds a bit like you guys are reading at times, I can’t put my finger on it exactly, but maybe you’re over enunciating.”

“Maybe too short actually. I feel like there was more that could have been said, perhaps they could have gone a little more in depth, and a little more personal input from the two of you.”

…To a Second Attempt

With the positive feedback and the first episode almost completed, I reached out to our next guest, Wesley Hoffman of Treehouse Networkshop. During our interview, we discussed networking strategies, and Julia and I attended one of his open events to try Wesley’s tips in the wild.


An interview with Wesley Hoffman and me, putting his networking tips to work

Just from writing out the script and listening back to the recording, I could tell the second episode was (unsurprisingly/thankfully) going to better than the first. It was longer, more personal, and more actionable.

And that was the last thing I thought about the podcast before I realized I needed to shut it down.

TWKY is Dead. Long Live TWKY

Like reading an historical biography, the ending was spoiled before you ever started reading. You already knew that TWKY was never meant to be.

But if we were getting positive reviews and things seemed to be going well, why did I abandon the project?

The main reason was simply that the project was too ambitious. At the outset, I figured a 10–15 minute narrative podcast (even if it required a bit of writing and audio editing on my end) couldn’t be that difficult. But I was wrong.

I underestimated the amount of time required to schedule guests, do research, conduct interviews, write a script, record Julia and my portions, edit and mix, create the blog component, and of course, promote it.

When I write all that down — it certainly seems obvious how much work would be involved. But in September, when I came up with the podcast, I was so excited about the idea of the finished product that I hadn’t taken any time to consider the amount of work involved.

So What Did I Learn (aka The Good Good)?

There wouldn’t be any point in publishing this mammoth essay (except for my own self-gratification) if I didn’t learn something along the way. Right?


It’s OK to outsource

I could have easily taken some of the work off my plate if I had gotten others involved with the project. Maybe someone else could have edited the show (better and faster than I could). Maybe I could have found someone to transcribe the audio.

Sure, that most likely wouldn’t be free, but sometimes you need to invest in more than just a microphone and domain name if you want to be successful.

In the future, I would definitely find free or paid help on some of the tasks that were stressing me out.

I don’t have to do it like everyone else

A lot of the podcasts that inspired this project are released on a weekly schedule. That works for them, but it doesn’t mean it works for me. Steven Dubner (Freakonomics) and Roman Mars (99% Invisible) don’t work a 9–5 job. They have time (and an entire team) dedicated to producing their weekly podcast.

As I plan my future podcast, I’ve come to terms with the fact that a weekly release with no set end (while attractive) probably isn’t feasible. And while maybe it wasn’t my “ideal,” it would have better to release monthly episodes or do a set season versus get overwhelmed and release nothing (simply because I can’t meet some arbitrary goal that Roman Mars can).

Nothing is ever wasted

It sucks that I spent $271.99 and didn’t release a single podcast episode. But that doesn’t mean I flushed money down the toilet.

I’ve found ways to put the microphone to work (I used it to record my Better Blog Course lessons and random interviews) and use the branding I paid for. (I featured the art on a limited edition tee).

Julia modeling for the I’m Making All This Up tee

The domain name’s still sitting there doing nothing, but it’s a good one…and it’s mine.

Of course, I invested more than just money into the project. I put 50 hours into the podcast and have little show for it. But just because I don’t have physical proof of that time doesn’t mean it was wasted. I learned the basics of Adobe Audition (which I used over Audacity because I already pay for Creative Cloud), I got good feedback on how to make a narrative podcast, and now, I know the process for next time.

I also got this super long article out of it…

Do You Have to Finish What You Start?

That’s the question all this has been building towards.

The answer — sometimes.

It’s a problem I have. I never want to finish what I start. I love coming up with new ideas and imagining the possibilities, but when it comes to actually doing the hard work, I start daydreaming about the next thing.

But most things worth doing are hard. If I always gave up when the going got tough, I’d never have published a book, created an online course, orstarted my blog.

But I felt justified in giving up on this project because I’d rather not do a podcast than release a podcast that felt rushed, half-baked, or inconsistent.Then again, I was only afraid that the podcast would end up that way because I’d set an ambitious (if not unachievable) goal. I was setting myself up for failure by stubbornly sticking to a plan I’d created before I understood the process.

So do you always have to finish what you start? No.

But maybe next time, instead of saying “this won’t meet my standards” and abandoning the project, I should check my goals and honestly ask, “Am I setting myself up to fail?”

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