Always Trying New Things to Grow The Working Experience Brand Makes Me Feel Like a Used Car Salesman

M. Francis Enright
5 min readAug 30, 2021
Photo by Steve Harvey on Unsplash

Matty Kerr is co-creator with John Brancaccio of The Working Experience. He is also a filmmaker and published author. Listen to our podcast on iTunes and Spotify and visit our website: theworkingexperience.com for videos, merchandise and more. You can also find us on Facebook, Linked In, Instagram, and Twitter.

TWE: Always Trying New Things Makes Me Feel Like a Used Car Salesman

I picture myself in a cheap, loud blazer, delivering my sales pitch to a skeptical man or woman.”

“Just see yourself and the wife and kids hitting the open road…it’s fully loaded…I drive this model myself…oh, that’s my mother-in-law’s name.”

I try to smooth out my comb over and try to cover the fact that I am sweating in desperation because I am way over-extended, drowning in debt and I need to make this sale.

“Well, let me show you something else!”

They are leaving, shrinking back, needing to get away from me and my hustler’s stink.

“Please!”

I sometimes feel like a cheap hustler with The Working Experience. We just hit 500,000 listens but we are still trying to get listeners, trying to get people to watch our videos, buy our t-shirts, still trying new things. But how far should we go?

A critic once opined that Madonna has the ability to constantly reinvent herself to keep up with the times. A counterpoint offered was that this just made her a product with no real identity as an artist. Businesses have to invent new products or, more commonly, just fiddle with old ones to keep up with new trends and demands. But is that how Madonna sees herself? As a business? Or is she an artist? What does she find valuable and fulfilling as opposed to just what sells?

A business also needs a core identity. People want to know what they are getting. If you run an Italian restaurant, you need to serve chicken parmesan, baked ziti and lasagna. If you run a Greek restaurant, you need to serve gyros, souvlaki, and roasted lamb and do it on a consistent basis.

If people go to a Rolling Stones concert, they want to hear Start Me Up.

However, tastes change. People want the old stuff, but they want new stuff as well: iPhones, Spotify, Tik Tok. Artists need to come out with new music.

The danger of constantly trying to follow the trends is never having a core identity. People just don’t know who or what you are. More importantly, you don’t know who or what you are. Catering to audiences is not authentic and they can sniff that out a mile away. Maybe it works in the short term, but if one is looking to do something fulfilling and meaningful, something that sustains, it is ultimately unsatisfying. If you want to be personally fulfilled by your endeavors, then you need to stick with what speaks to you and not worry about the audience.

However, I also want to make money from The Working Experience, the podcast and the brand. So how do we grow our audience and try new things without losing our core?

Disclaimer: I have no idea. I pose questions; I do not answer them.

Conventional wisdom tells us that with a creative enterprise many ideas need to be tried and see what sticks. I get it. There is a lot of trial an error. We have tried a lot of different things for The Working Experience: fifteen minute Thank God It’s Monday episodes (kind of bombed); fifteen minute Thank God It’s Friday Episodes or It’s Friday MOFOs (really bombed). I spent about $1,000 to shoot some short comedy videos for Twitter, Instagram, and Facebook (bombed). I did a bunch of short videos just talking into my phone from an office I set up in my house, playing the part of a paranoid employee. It bombed. Crickets.

We spent about $3,000 employing a social media expert to get more listeners for the podcast and more views on social media. Nothing happened. We may have gotten a few more listeners but we may as well not exist on social media. We might as well have flushed the money directly down the toilet.

As far as merchandise goes, we have sold four t-shirts, which I bought for my family. I suppose I could just keep buying the shirts, but I don’t think it is a sustainable business model.

Part of me gets tired of trying to find ways to make money. It is makes it difficult to focus on one thing and really make it quality. I am not a businessman; I do not enjoy selling products or marketing. I do not like being a schemer, looking for the next big thing. I’m no good at it.

If I had to make a living selling cars or real estate, I would starve.

On the other hand, it is an interesting challenge. I like coming up with new video ideas and seeing what works. I like trying new things and seeing if the audience responds. It feels good when we are ranked in the Top Ten for Business and Careers in Ghana, Angola, or Finland. We are creating something.

We do need to try new things for our audience but also for the sake of our own satisfaction. We do not want to keep doing the same thing over and over even if it were successful. Audiences are difficult. People want what is familiar but we need to hold their attention too. There is a sweet spot in there.

I get a rush from the prospect of actually making The Working Experience into a profitable brand. Reaching the half million unique listens mark feels good. We do have a lot more listeners than many of the podcasts out there, putting us the top 10%. (It honestly seems like if we are in the top 10% we should be able to make money but that is just not the case in the Wild West of Social Media.)

And I have had the opportunity to interview many interesting people, people I would never have crossed paths with in my ordinary life as a teacher. When or why would I have had to opportunity to speak with Congresswoman Donna Edwards or the Deputy Chief of Counterterrorism for the CIA, Phillip Mudd? I see these people on CNN and MSNBC and I actually got to speak with them. Coach John Beam, Coach John Mosely, Brittaney Wagner, all from Netflix’s Last Chance U. These were awesome opportunities, and I learned a lot from those conversations and I think our listeners did too.

I need to appreciate that.

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M. Francis Enright

Co-creator and cohost of The Working Experience Podcast. We explore what people do for work, how they do it and how they feel about it. Twice a week!