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Confessions Of A Failed Entrepreneur


I have gotten to this point before. Staring at a busy computer screen after hours of work, I had finally reached the moment where you shift from the planning phase to implementation. After a few keystrokes and entering my credit card info, the State of Florida graciously accepted my funds and established my business.

This was my first incorporation. Since the establishment of my first business adventure at age 20 I had remained in the land of the solo entrepreneur, also known as, the sole proprietor.

To me, I had felt like I had stepped up to the big leagues.

Like a Tim Tebow, out to prove himself in this game of business chess. Getting that first at bat would be a slightly trickier task.

It was early 2016 and my mother had just retired from 30 years of working at a deli in our local grocery store. Over the years, she had seen me try one project after another to no success, but never giving up.

My entrepreneurial spirit came when I was a 17-year-old teenager. My mother and step-father had just divorced, and our comfortable middle-class life quickly morphed into a poverty-stricken reality. The next several years we would be buried in debt and had even found ourselves without running water for 2 months.

We had to slowly save up money to afford getting our water pump fixed. In the meantime, my brother and I had to go to the local park to fill plastic milk jugs for drinking and showering. That was also when I was forced to learn how to make repairs myself.

We saved for a pump and I learned how to install it. On a side note, it is a great feeling when you accomplish something like that.

I had vowed that I was not living like that ever again.

Fast forward to 33-year-old me and I was finally staring at the possibility of making that life changing financial progress. Mom took a $10,000 chunk of her meager retirement and surprised me with an investment. This was a moment I didn’t take lightly, and I had promised her that we would soon be vacationing in Hawaii within a year. I was motivated to make a change and to take my mother to the place she had always wanted to visit. Her dream vacation.

It doesn’t matter how well researched your business plan is, there are always bumps in the road and mistakes to be made.

I had always wanted to start my own food truck. The popularity of food trucks in my city had grown very quickly. These are not your regular side-of-the-road roach coaches. Many of these trucks are operated by high quality chefs from the local area that easily bring in over 100k per year.

Within a 5-year span there had been at least 50 trucks of various offerings operating around the area and events centered around them became wildly popular.

I come from a background of cooking food as a part-time chef. My family has been working in and owning restaurants for many years. My full-time career since high school had been manning an ambulance as a paramedic. After 13 years of lights, sirens and 3 am wake-up calls, I was ready for a career change, I wanted to retire from the 911 life and start my very own food truck.

I had the plan and the menu, but because of inexperience I started to make critical mistakes.

Mistake #1- The Cart Before The Horse


Sometimes excitement can force you to make quick decisions and then you realize that your steps are out of order. This was a project I was trying to bootstrap on a limited budget and build the truck myself. Shortly after purchasing my used twenty-three-foot panel truck from FedEx, using a large chunk of my budget, I ran into issues with installing other equipment.

After navigating a series of unfortunate events, I came face to face with a problem that ended up derailing my food truck plans altogether.

I didn’t realize my FedEx panel truck had a fiberglass roof. I didn’t know that mattered either.

Why is this important?

Building a food truck requires having a stable roof to be able to connect things like overhead lighting, exhaust fans for the hood system, gravity fed clean water tanks which eliminates the need for pumps, shelving and fire sprinkler system hardware. This was an issue that caught me completely off guard.

Since I was fresh out of sheet metal, rivet guns and no money budgeted for stupidity, I was reeling for an answer. What in the hell was I going to do?

Mistake #2- Not Asking For Help Or Finding Mentors

My past circumstances in life had brought me to be very independent, even to a point of trying to do everything myself. No amount of reading and research can help you like an experienced mentor can. Find someone who has been there and done it. This is gold. This will help you to see that you really don’t know as much as you think, especially when you are taking on a project you have never done before.

At this point I had burned through half of my budget and I was nowhere close to being able to put a truck on the road to make money. What next?

Mistake #3- Trading a business model with a well-researched plan for one that has no plan at all.

When you work two jobs and have put everything on the line starting a business to create a better life, the last thing that you want to do is put it aside and regroup.

I was desperate for change and I wanted to finally make it. I wanted to prove the haters wrong and I wanted to win.

Instead of shelving the plan or finding investors, I thought I could launch a catering service to get something going and start making an income. I could come back in a year with more money and build the truck right.

At the time, I had created the incorporation but hadn’t applied for any other food related permits yet. To operate a food truck in Florida, you must operate from a licensed kitchen or commissary. Since the commissary I was going to work with had a large commercial kitchen ready to rent, it made sense at the time. The kitchen rental was affordable, and the permitting was easier because of the other small caterers that were already renting here. The Health Department evaluation process was a breeze.

With those things in mind, I changed my plans and became a caterer. Oh boy!

I had worked at catering companies before, so I was confident in the process. I changed the website, retrofitted my food truck menu to a classy catering menu and kept a lot of the same recipes. I advertised on several of the wedding and party planning sites and found a couple of early customers. Which brings me to…

Mistakes #4 and #5- Get it in writing, especially with family AND ALWAYS charge people you know, MORE! (seriously)

Not long after I started, I began advertising the business on my social media accounts. One of my cousins had asked if I would do a tasting and give her a quote for her wedding, which was about 8 weeks away. If I hadn’t popped up when I did, she said she was going with a local BBQ chain that was charging more than she wanted to pay.

The count for the wedding was 110 people. I saw quick opportunity to get my brand out there. Not only was I going to be able to test the process with a large crowd early on, but I was also going to use this as an opportunity to market and get more business. Pretty basic, right?

Since she was family, I decided to give her a nice discount and undercut the competition. I figured that the marketing potential was so high and wedding season was approaching fast, I could likely get another gig or two by word of mouth. How could I go wrong with that logic? That’s how this game works, doesn’t it?

It’s what you don’t see that gets you. Not everything is under your control. A lot of things are not under your control.

The day of the wedding wasn’t that stressful for me, not like I thought it would be. My business partner (and best friend) and I, had got an extremely early start and had the kitchen fired up and going. This was our first time using this kitchen, so there was a bit of a learning curve.

My anxiety didn’t start kicking in until we had started closing in on delivery time. Our kitchen was a 45-minute drive to a small country church out in BFE and we had to have the truck packed-up and rolling out at a very specific time.

We had documented our process well along the way, the pros and cons and stuff. We even managed to have a decent self-evaluation for improvement for the next event. We were confident in ourselves and our food.

I had arrived at the venue right on time. I was relieved to find out that the wedding was delayed shortly, while waiting on the bride’s family. That gave me more time to perfect the set-up.


At this point in the story, it would be a good idea to catch you up on a few key details.

First would be the that when I did the tasting, about two weeks prior to the event, I had dealt solely with my cousin, the bride. I didn’t know until later that her future grandmother-in-law was paying for the catering until the day of the event. It’s imperative that you know exactly who you are dealing with, period.

The tasting went well, and we had zeroed in on her perfect menu. Simple, but elegant. She was very pleased with what I had presented. That was also the time we had decided on price and she handed over a check for a deposit at the end.

I had failed to create a contract, something that most people wouldn’t think would be necessary when dealing with family, and it proved to be my undoing. If you run a service business of this type you MUST create contracts and outline each detail, so both parties can agree on what to expect. File that under Basics 101.

So, back to the wedding day.

I had finished the table in time and even stayed during service to replenish the set-up, something that wasn’t being charged for, but I did so I could market and get feedback. I hadn’t noticed the crowd size at that time, I was too involved in talking to guests and handing out business cards. Overall, I had received very positive feedback and even a referral for another event. Bingo! Just the jackpot I was banking on.

At the end of the dinner, however, I was approached by the bride and her new grandmother-in-law.

They had to pay me still, but by the look on their faces as they closed in, I started to get an empty feeling in my gut. They had asked me to exit to the parking lot with them.

In utter amazement, I had stood by while being blind-sided by complaints, ugly comments and the bride’s apparent disappointment. After a quick 2-minute tirade my cousin walks away and leaves me alone in the church parking lot with her new witch-in-law.

What had happened? What went wrong?

I had many compliments and I didn’t see anyone in the wedding party making faces while eating. If you cook for crowds, you know we always watch the initial reactions. All smiles.

After about 30 seconds of listening to this person talk, the light bulb had clicked, and I knew what was going on. Thirty seconds after that, she even had the audacity to say it out loud.

This is a lesson for your future, always get a contract signed.

She had smugly stated this as she turned and walked back inside.

You have got to be kidding me, was this the plan all along?

Further investigation revealed that the head count for the so-called 110-person event, was 41. I had been shafted because they were unpopular and mad that no one showed up to this wedding.

Now, they had big bill to pay and decided to rip me off instead.

My own sister and brother- in-law were present and they were shocked by what had transpired. They as well said good things about the food and didn’t hear anyone complaining.

As crappy as this moment turned out to be, I had really learned a lot but didn’t realize it right away. I had decided to close shop. The following year, I had fallen into a deep depression and was drinking all the time. The impact this failure had on me was tremendous. I lost my confidence and was mad at the world. Another failure.

After that rough and emotional year, I had finally got my head out of my ass and got help. I quit drinking and started getting focused on getting back into the business game.

I had decided to write off those thousands of dollars lost as an investment in my education. The School of Hard Knocks will kick your ass and take no prisoners. I had learned to dwell on the positivity of life and what I had, not on negatives and what I didn’t have.

I learned the hard way of the importance of contracts for all. I learned that if you deal with family you should charge them more. They are more likely to take advantage of you. I learned that having a great mentor can save you your time, your bank account and your business life. I learned to never drop off the food, until you have the check in hand for the balance of the project. No money, no catering, no reception. See how that works?

All in all, there are always going to be issues to deal with that you will never see coming. You just have to have the best back up plan possible and be flexible to roll with the punches. Even more important than that, you must be aware of the basics like contracts, the nuances of your venture and learn skills like negotiating.

You can never learn too much. Find the free resources and the platforms where you can meet mentors. Take online courses to sharpen your skill set. Use your skills to set you apart from the pack. Get out of your comfort zone and see what works and what doesn’t.

Don’t stop and never give up!

-Paul Cercy

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