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my most humiliating business failure

Like many business owners, my “origin story” into the world of entrepreneurism had a rough start chock-full of embarrassment and humiliation.

I did a lot of stoopid thangs when I started my first business. And I’m telling you this story as a cautionary tale, so you can prevent some of the boneheaded mistakes I made.

Let's rewind our clocks back to 2015:

In 2015, I was still in a touring band. We played shows all over. We went on a week-long Colorado tour. We traveled down the east coast, hitting the Carolinas for another week-long tour. When we weren’t on week-long tours, we were on weekend-long tours. We typically played 3 or 4 weekends each month, and each weekend we’d have 2-3 shows. We recorded two albums in the studio while I was in the band. And we practiced at least a couple times a week.

I say all that just to explain that I was busy as a mf during this time. I had a part-time job that paid me pennies on the dollar, i.e. just over minimum wage. And I listened to a bunch of podcasts which spawned an entrepreneurial itch deep inside my psyche.

One of the podcasts I listened to at the time sponsored what sounded like, in theory, a great business opportunity. I could work on my business while I traveled with my band. What could go wrong?

Well, everything did. Murphy’s Law in full effect.

I forget the name of the specific software, but methinks it’s gone out of business by the time you’re reading this story.

Anyway, here was the gist of the software:

This software helped you create apps that you could then sell to local businesses. Think an app for restaurants where folks could browse your menu, see your orders, and even order online.

The app cost something like $500 to buy, which seemed like a small price to pay to sell local businesses an app for at least $1,000 bones. And I had an investor: My grandma.

Anyway, I made a bunch of humiliating mistakes (which came back to bite me in the arse when I explained to my family that I was quitting my cushy job to launch my own business four years later).

My first mistake?

Not doing my due diligence.

I let the dopamine about the idea of starting a business cloud my judgment. I thought it would be easy-peasy to go to local businesses and sell them an app for their business. And I thought the piece of software I (errr, my grandma) bought would help me make attractive and useful apps.

I couldn’t have been more wrong.

The app was an utter piece of junk. The few apps I made looked hideous. The interface I used to design apps was worse than using WordPress to build an attractive site when you don’t have any coding skills. In fact, MySpace was easier to use and design on… IYKYK.

Describing the hate I felt trying to use this app to make an attractive-looking app is almost impossible. I saw red every time I logged in. I felt humiliated that I wouldn’t be able to pay back my grandma. And worst of all, I felt like a fraud drowning in shame any time it popped into my head.

My second mistake?

Not doing ANY market research.

Again, I blame the dopamine my brain released when I got the “ok” from my grandma that she’d invest in this side project.

I just kinda figured local businesses would want an app.


Not only did they not want an app, but this was the time after apps became super popular. Nobody used apps anymore — not business owners nor their customers.

The only apps people had on their phone were the usual suspects: Twitter, Facebook, YouTube, Fantasy Football, Maps, etc. Non-social media or entertainment apps already died a quick and sudden death. But I didn’t care, because the dopamine surged through my brain whispering sweet nothings into my ear into how I could become rich.

Turns out, no business owners I talked to wanted this app. And I gave up completely after being rejected a few times.

Back then, I didn’t know how to deal with rejection. I still took it personally. But mayhap it was a blessing-in-disguise because I became too embarrassed to even approach any more business owners because I didn’t believe in my product because every app I “created” with their drag-and-drop interface looked like a steaming pile of hot shit.

My third mistake?

Ignoring all the red flags and trudging along anyway.

The apps looked like shit.

The business owners I reached out to laughed in my face.

The customers the business owners would sell these “apps” to wouldn’t have used them if you paid them too.

And not only did I suck at sales, but I feared rejection.

In other words, I had a recipe for disaster, humiliation, and failure.

I called this business “APParatus Mobile Apps,” which I thought was oh-so-clever at the time. And it made a whopping $0. Actually, it lost me (aka my grandma) $500 because I didn’t sell a single app.

My fourth mistake?

I had no good “offer.” I don’t remember what my “offer” was, but it was probably even worse than the apps I created.

The only mistake I didn’t make?

Quitting on the business, and going back to square one.

Now, I don’t usually advise giving up on a business after feeling the sting of rejection a few times.

When I started this business—my copywriting one that pays my bills, funds my travels, and generates my freedom—I dealt with a ton of rejection. Especially when I first started because I sucked at sales, to put it mildly. But I kept trucking along because I believed in myself, my offer, and my copywriting skills. I can’t say the same about my failed app building business.


If you need a partner to help you minimize your mistakes in business, focus on the fundamentals of building and scaling a business, and increase your email revenue by as much as 264%…

You read this article for a reason you know — and this is your sign to take the next step towards building your dream business and life.


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