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A Podcast about Failure – Smart Passive Income


Have you ever failed at something?

For a while in late 2020, we were failing pretty hard at developing a new podcast.

Last fall, the SPI Media Content team (yours truly and senior content manager Karen Beattie) and Podcasts team (senior producer Sara Jane Hess and producer David Grabowski) put our heads together to brainstorm ideas for a new show.

Our mission was exciting but daunting: to come up with a compelling podcast concept, something that could stand astride our flagship shows, the Smart Passive Income Podcast and AskPat 2.0, but also stand on its own. We wanted to create something new and different. Some fresh energy that fit the brand but also expanded it. And of course, something our audience would be excited to tune in to.

No presh, right? Here’s how the process unfolded.

Take 1: A New Spin on an Old Idea

Our first idea was a show where we interviewed everyday entrepreneurs and experts about the sweet—and sometimes bittersweet—road to success. 

We thought about answering questions like: What does success mean? How do you find it? Why is it sometimes so elusive? How does it feel when you finally get it? And what happens when you lose it? 

Yeah, success stories aren’t exactly a novel concept. But we figured if we approached the subject from enough interesting angles, we could do something cool with it. We thought we had something.

So we got to work creating a test script for a pilot episode, based largely on snippets from interviews we’d done earlier that summer for a series of entrepreneurial success story blog posts.

Having those interviews to work with gave us a boost, and we threw together the script pretty quickly.

Our very first test script: the making of the sausage.

But the script felt, well, stitched-together. And more than that, we realized we just weren’t that jazzed about the concept. Success is awesome! We just weren’t sure we had a lot of new things to say about it.

So we kept brainstorming.

Take 2: The COVID Diaries

Our next idea was a show about how entrepreneurs are coping, surviving, and maybe even (gulp) thriving through the havoc COVID-19 has wreaked on our lives and businesses.

Once again, we dipped into our success story interviews for material. The coronavirus pandemic was (unsurprisingly) a theme in all of those interviews, so we had a decent amount of content to create a test script again.

This time, we felt like we had something a little more focused to work with. Maybe this idea’s got legs! We used our test script to record a test episode, complete with intro music, to see how the concept would land in our ears.

Aaaand it landed kind of flat.

As we found with the first test script, using bits of interviews we’d recorded for a different purpose and piecing them together with new commentary just didn’t result in a highly compelling piece of podcasting.

And with things changing so quickly on the epidemiological front, we also wondered if the COVID focus would reduce the podcast’s shelf life. (COVID obviously hasn’t disappeared yet, so maybe the concern was ill-founded, but it’s what we thought at the time.)

Everything considered, a COVID-focused podcast didn’t grab us the way we wanted it to, so it was back to the drawing board.

Take 3: Getting Closer! (Or Are We?)

We tossed out some other ideas. We workshopped them, and even came up with outlines of what a season of each of those shows might look like.

But the upshot was—for various reasons—we either didn’t feel excited enough about, or ready to turn any of those ideas into a podcast right now.

(You’ll notice I didn’t share any specifics, because we might still turn some of those concepts into a podcast some day!)

So we marched on.

Take 4: Flops Arrives

Then we got to thinking about our original idea: success. Maybe we’ve got it exactly backward. What if we flip the script and talk about failure instead?

And thus Flops was born.

What’s Flops? I’ll let the trailer do the talking:

Our vision with Flops is to present an honest portrait of entrepreneurial failure in its numerous forms. Season 1 features interviews with entrepreneurs who’ve failed big in some way, along with stories of failure from recent and not-so-recent history, in business and beyond—along with some guest cameos that reveal a lighter side of failure.

It may sound cliché, but failure really puts things in perspective. It’s amazing what people can withstand and bounce back from.

In season 1 of Flops, we talk to more than one entrepreneur who lost six figures, one whose new business got exactly zero clients, and another whose first retail product was bleeding money while she battled cancer.

These three entrepreneurs bounced back in different ways, while others we spoke with are still struggling to find their footing. We want to show the messy, unvarnished side of failure, because failure is to be expected. Failure is human. And it can change your life irrevocably, sometimes for the better, and sometimes not. What really matters is what you do with that failure.

So say hello to Flops. We hope it doesn’t fail, because we believe these stories are valuable to hear—and that we’ve put together a podcast that tells them in a pretty compelling way.

But if Flops does fail, well, we’ll dust ourselves off and try again.

The first season of Flops launches this Wednesday, March 31, with new episodes every Wednesday. Find it at smartpassiveincome.com/flops, and on Apple Podcasts, Spotify, or wherever you listen to podcasts.

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