What My First Failed Business Idea Taught Me About Life

And what you can learn from my mistakes


Jon Upshaw

3 years ago | 5 min read

Photo by George Becker from Pexels

“Unfortunately, I’m no longer in business. for the inconvenience.”

Those were the final words I spoke to my last customer. Hearing those words come out of my mouth was embarrassing and disheartening, but I knew it was time to call it quits on my personal venture after 3 months of attempting to scale my prototype startup at the time — an apartment-based garbage removal business for college students too busy and too concerned about the safety risks to walk 50–60 yards to the dumpsters during the evenings.

Before starting my first business, I had read the story of Jeremy Young, Art History student student turned entrepreneur after successfully scaling his unique approach to laundry services at Hamilton College in Clinton, New York. Inspired to do the same, I decided that I wanted to create my own job instead of working for someone else.

While at work the following week, the idea came to me in a flash of inspiration. If I didn’t know any better, I could have sworn that some Muse of Startup Ideas had blessed me with her presence and delivered to me the multimillion-dollar idea I had been yearning for. I quickly began typing out the business concept when I got home later that day.

It wouldn’t be long before I pitched the idea to a close friend to check whether or not I was stupid for thinking of it. After the conversation confirmed that well, maybe I am onto something, I adjusted the pricing strategy, created a Facebook business page, and designed a small flyer to print and distribute around the student apartments I lived in at the time.

Yes, this was my idea for the advertising and brand concept.
Yes, this was my idea for the advertising and brand concept.

To me, it seemed like the perfect set of circumstances to start this kind of business in: college students are normally strapped for time, and there had recently been increasing reports of crime near my college campus. This meant that people were less likely to go out anyway, especially at night. Plus, my college apartments normally charged students fees in addition to their rent if trash was left outside for too long. My business idea would save college students both time and money.

It was game time.

When Opportunity Met Adversity

I posted flyers around the apartment complex. I pitched my services to college students around the area. Then, there was that one time someone practically ran away from me while I tried to sell them on the idea of hiring me to pick up their trash for them. Ouch.

But after a week or so, I had actually managed to acquire a few customers and things seemed to be picking up. This is why rejection is only temporary, or so I thought.

However, the property manager soon picked up on what I had been doing and shut down my advertising operations immediately. Because the majority of my advertising had been previously done on the property, that meant the method I used to get most of my customers had been immediately eliminated. To keep up my business, I absolutely had to find another way to market to customers.

Another rising issue I experienced was that of customer management. At the time I had 3 customers, each paying $5 a week. Taking out their trash, on the other hand, required a significant amount of effort relative to the time it took me to complete the task. I realized that my pricing model, though cheap and designed for the low-income college student, was seriously flawed. Even if I had managed to use social media to acquire more customers, there was no way I could manage any more than 5 before needing to hire someone else to help.

To make matters worse, I didn’t even have the resources to scale the business model appropriately. To acquire more customers required more people and more transportation resources, not just me — a struggling college student with no car.

Because of these fatal flaws in pricing and resource management, I was only able to maintain a relationship with those 3 customers. Had I understood how to connect with the right people with the right expertise and resources, I could expanded my customer base quickly and pivoted my advertising model away from traditional print distribution.

In the end, those three customers eventually turned to zero as I gave up trying to scale the business in favor of finishing the semester. However, there were a couple of lessons I learned from that experience — lessons I hope you take with you on your next business venture.

Lesson #1: Figure Out Your ‘Why’ — And Make It Clear

When starting my first business, I knew that I wanted to be financially independent and create my own source of income. While it was clear that my business addressed an everyday need and generated some profit, that initial motivation began to wane once I didn’t get what I expected.

Take it from me — without a clear and distinct reason for building your business that involves more than just “being your own boss”, you set yourself up for failure when you don’t get the results you want.

Everyone has a unique motivator that drives them to overcome their fears when times call for it. Make yours special to you and don’t follow the influencer crowd.

Lesson #2: Customers Generally Want The Greatest Benefit For The Lowest Cost

This was a harsh one for me to accept. In other words, I underpriced my services and the customer was happy to pay for them — but not for the reasons that I was thinking. The effort required to take out their trash required a lot of time and energy from me, and they only had to pay $5 a week for it!

Know and be confident in the monetary value of your business, whatever it may be. It’s the one thing that separates a successful venture from a failed one.

Lesson #3: You Might Look Like An Idiot— And That’s Okay

Being an entrepreneur for the first time was a great learning experience for me. It was clear that I didn’t know what the hell I was doing, but I certainly had fun taking the risk and making myself look like an idiot at times.

It’s common knowledge that building any business requires some level of risk-taking. What isn’t commonly known, however, is that the more risks you take, the more resilient you become as a result of experiencing failure.

My Final Thoughts

I think everyone should try entrepreneurship at least once. If I ever choose to have kids, I would want to encourage them to blaze their own trail as early as possible in life.

I would tell them about all the times that I failed, and help them understand that failure does not mean life is over or that it’s time to give up.

Lastly, I would demonstrate to them that my firm belief in the idea that we need persistent innovators and creative thinkers in the world, or else humanity would never question its place in the universe.


Created by

Jon Upshaw







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