Funny Stories about my Life — Wantrepreneur
“I have not failed. I’ve just found 10,000 ways that won’t work.”
Thomas Edison
At the end of 10th grade, my friend Jeremy suggested we open an ice cream truck business for the summer. Just this mere suggestion set my mind on fire with excitement. The idea of running my own business captured my imagination, and it quickly became my sole obsession. I pictured myself rolling up to the suburban Atlanta neighborhoods and kids of all ages swarming my truck, eager to hand me cash for one of my tasty frozen treats.
Besides, this would enable me to quit my embarrassing current gig of cooking burgers at McDonald’s.
I began doing my due diligence and researching what it would take to procure a business license. Did we want to go through the Good Humor franchise program, or should we just build out our truck our way and buy product wholesale?
Should we hand pick our favorite treats and give them clever regional names like Georgia Blue Balls and the Kennesaw Claw, or do we stick with the tried and true Three Stage bomb pops and Fudgsicles? How do we set prices? How do taxes work? How much startup cash did we need, and how would we get it? I had so many questions.
Diving deep into the nuances of the ice cream business, I called Jeremy to run some name ideas by him.
“How about Atlanta Frozen Delights?” I asked.
“My dad won’t let me. He says I must work with him hanging billboards all summer. Sorry man.”
There was no way I’d have enough money to buy the truck on my own. Deflated, I gave up my brief dream and went back to flipping burgers in a paper hat.
After transferring to the University of Georgia my sophomore year, I started smoking lots of weed. My minimum wage job serving desserts didn’t make it easy to justify spending $40 for a quarter ounce of Mexican schwag. Consequently, I started buying ounces and selling three quarters so I could smoke for free. Over the course of the year, I graduated to ¼ pounds and then to pounds. I no longer was just making free weed but also pocketing a handsome profit.
My customer base grew, and I took my illegitimate new business seriously. Unlike most weed dealers, I was responsive and reliable. The only problem was that I was terrified of getting busted and going to jail. I recognized that I was only getting paid to sell weed because I was willing to take the risk.
I was making 1–2k/month in profit, which enabled me to live comfortably in college and beef up my record collection, but I knew that my whole world would come crashing down if I were ever caught.
I proclaimed I needed a legitimate business to “clean” my money as I saw in the Godfather movies. It was a ridiculous idea, but I really just wanted to run a legitimate business. I talked my roommate and fellow drug dealer Bradley into opening a legit business fulfilling two unmet needs on campus. We applied for our business license, and “Clean Greens Veggie Stand” was born.
We had no intention of selling vegetables, we just thought we were so clever and opined that we were “cleaning our greens,” which was our illegitimate weed profit. Clean Greens sold Snapple and cigarettes. I wasn’t a smoker, but everyone was always bitching about not having anywhere to buy smokes on campus, and Snapple was so much better than the offerings in the campus Coke machines. Opportunity knocks, so I was going to sell those cancer sticks and fancy juice drinks at a handsome markup.
After utilizing our business license to establish a wholesale relationship with a food and beverage warehouse, we procured our inventory and picked our spot on a busy corridor in front of Stegeman Hall. I set up my homemade sign, and we opened for business.
The response was tepid initially since nobody knew what we were selling. So I decided to use my pipes to get the word out. “Snapple and ciggies….come get your Snapple and ciggies!” I barked at a high volume between classes to the throngs of students passing by.
The smokers came out of the woodwork. I moved 2.5 cartons of ciggies and a case of Snapple in my first 3-hour shift. I felt bonified. This is my first real business!
The next day, it was Bradley’s turn to work the Clean Greens stand since I had classes all day, which was our agreement. I told him I’d meet him there with the inventory and help him set up. He slept in and left me waiting for over an hour until I had to stash the inventory and go to class. I was perturbed.
Later that evening, I confronted him about standing me up, and he told me he didn’t think we’d really have to work the stand, and there was no way he was going to sling drinks and smokes for hours at a time. He quit before he even started and taught me my first business lesson in the process:
DON’T GO INTO BUSINESS WITH LAZY DRUG DEALERS.
I worked at Clean Greens periodically for the remainder of the spring of 1996 until I ran out of inventory. Atlanta was hosting the Olympics that summer which had the entire region abuzz. My college town, Athens, was hosting several Olympic events, including the final 8 matchups for the Olympic soccer tournament, which was a huge international draw. The downtown city streets were being closed off to car traffic so international tourists could revel and celebrate the 1996 Olympics.
“This is a huge business opportunity,” I told my friend Raze.
He agreed, and we hatched our plan to open “Classic City Artwork,” where we’d sell artwork to wealthy European travelers and make a mint. Over three months before the Olympics, we signed an agreement with ten local artists to sell their work on a consignment basis over the 2.5 weeks of the Olympic games.
\We rented a booth and diligently wrote up descriptions of each piece in our tent. Our friend Eric agreed to allow us to store all the artwork in his record store at the end of each day. We spent over two months getting ready and were ecstatic for the Olympics to start and see the tourist dollars flow.
Raze and I worked hard to get everything set up. It would be a hassle to set up and break down our display every day and night, but we couldn’t risk our artwork to theft or rain and were ready to do the work. We raced around the morning of the opening ceremony to ensure we’d be prepared for the crowds.
Our display was organized and appealing, and we were finally ready. It was 95 degrees with 70% humidity that day. Wanting to come across as professional art dealers, we ignored the heat and dressed in sportscoat and slacks with dress shoes. We were businessmen.
The other vendors lined up and down College Ave and were also ready. This was going to be huge!
On the first day, nobody came. I don’t mean that just a few people came and didn’t buy anything, literally, nobody came to our booth or to any of the other booths. We were open from 10a to 9p, and only a few local Athenians meandered down the streets. They definitely weren’t buying anything.
The second day was just like the first, with no action. The third and fourth days were equally desolate. The soccer tournament didn’t start until the second week of the Olympics, so we pinned our hopes on week 2. We abandoned the suits and dressed like the college kids that we were.
The vendors all got to know one another, and we passed around a petition to get our money back from the asshole who organized the debacle. The turkey leg guy was livid, he was sitting on 2000 giant turkey legs and had sold less than 10 by the end of week 1.
Each day, we’d hear from our friends attending the various Olympic events in Atlanta and Athens while Raze and I sat in the Classic City Artwork stand feeling like losers. We felt deflated and agitated at the same time. We weren’t only losing our ass, we were missing the Olympics in the process. A few more people showed up in week 2, but not many. No European teams made the final 8 in soccer which didn’t help matters.
We had one couple from California agree to buy a $400 sculpture, but they never came back at the end of the night to pay and work out shipping arrangements. My mom came up one day, and I took the afternoon off to see an Olympic soccer game before returning to work at the empty art booth.
After 3 months of prep work, we literally didn’t sell a single piece of artwork. The entire exercise was a waste of time and money. We were pissing in the wind, and I felt like an A-1 asshole for dragging my buddy Raze into the failed endeavor.
As an English major with shitty grades, I was like a boat without a rudder. I wanted to run my own business but didn’t know how or where to start.
Although I was a failure in business thus far, the one thing I was confident about was my ability to throw a ragin’ party. Additionally, I had been training at the boxing gym weekly for a year and wanted to learn how to fight. Pairing these two objectives, I decided to organize and host a boxing tournament combined with a chili cook-off.
My best buddy James helped me carve out a dirt ring in our buddy Frank’s backyard, and we put 5 kegs on ice. We bought headgear for the fighters but inadvertently bought junior-size equipment that didn’t fit on anyone’s head. Fuck that noise anyway. Seeing everyone’s faces as they battled each other was more fun anyway.
The tournament consisted of 8 heavyweight and 8 lightweight fighters. This was a single-elimination tournament, meaning the winner would have to win 3 fights that day to take the trophy. I was a svelte 190 pounds and fought in the heavyweight division with several of my friends, including James.
My good friend Pat was scheduled to fight in the lightweight division. He came by my house the night before to spar with me in my parking lot to get ready. He jacked me in the jaw right off the bat and then followed it up with a powerful right to the side of my head. He damn near knocked me down, and I was rattled.
I sure am glad that skinny motherfucker isn’t in my weight division, I mused as I shook the cobwebs out of my brain.
We had three judges, a dirt ring, a ton of beer, and a boatload of chili. The college kids came in droves, and the party was on. We required that all of the fighters take a nickname to make it more fun. My buddy and roomie “Fat Rail Cale” beat the shit out of the Elfpower singer “Ragin’ Reiger.” (rock stars aren’t fighters) Then “Pinto Bean Pat” beat the holy beJesus out of Fat Rail Cale and advanced to the lightweight finals where he dominated “Bootyman Boudreau” to take the lightweight title.
My first fight was against my fellow rugby teammate “Salty Brock.” I declared my boxing name was “Shitfoot” which I borrowed from a funny anecdote about a nasty short bastard that would pick fights with big dudes then beat his larger opponent into submission, before stomping his opponent on the back of the neck ala Ed Norton in American History X.
I was nervous about my first time in the right, but my adrenalin flowed and I was in good shape.
I fought hard, but Salty Brock was athletic, ambidextrous, and slippery. The battle went the distance, and I barely pulled out a victory on the judges’ scorecards and advanced to the second round. I bulldozed my second opponent to earn my spot in the heavyweight finals. “Hurricane James” won his first two fights to pare me up against my best friend, mono y mono.
The crowd of college kids was abuzz.” How are you going to punch your best friend?” I was asked.
“Easily,” I responded.
Our fight was epic and bloody, and I was fortunate to win. The party was off the chain.
I was going to be a boxing promoter.
James and I procured a business license for “Dirtcircle Promotions,” and we convinced the owner of 40 Watt Club to let us book our first legit boxing tournament in the spring of 1997. We brought in a quirky 6'6" ring announcer and convinced the hottest girls we knew to be our scantily clad ring girls.
James and I spent four months planning and promoting this event, including doing radio shows and press releases to promote the event. We expanded to three weight classes, added a smaller female boxer bracket, and even convinced a Falcons cheerleader to sign up to fight. We built a massive tournament board suspended high up behind the boxing ring so everyone could follow the single-elimination tournament as it progressed.
On the event day, I was apprehensive about yet another business failure. I decided to dip my head out of the venue thirty minutes before the doors were to open at 40 Watt. To my delight, a line of college kids stretched three blocks up Washington Street. I breathed a sigh of relief.
We packed the house both nights, and the event was a raging success. I also fought in the tournament and won the heavyweight division. (A little bit of training goes a long way.) We made 5k which James and I split down the middle. We felt good about ourselves.
We immediately planned our next tournament and named it the “Fall Classic”, which also went well. This was my first taste of business success, and it felt fantastic.
Once the elation of hosting a successful event subsided, the reality was that this was not a full-time business. We decided to try to duplicate our success on other campuses and scale up so we could become full-time promoters. We tried to host a tournament at Georgia Southern University a few hours south but didn’t get any traction. It was difficult to attract fighters when you didn’t live on campus with a sphere of influence. I didn’t realize it at the time, but I was learning another important lesson in business:
BUILDING A BUSINESS TAKES EXTENSIVE PLANNING AND RIGOROUS EXECUTION. DESPITE BEST EFFORTS, THE BUSINESS WILL STILL LIKELY FAIL.
After seven successful tournaments in Athens over a 3yr timeframe and zero events elsewhere, I had to get a real job. James decided to change his life and move to Montana. My 4th business, Dirtcircle Promotions, was a terrific experience, but our business model had run its course.
Five years later, my friend Aidan asked me to promote rock shows with him. I was working full-time for a predatory mortgage broker and was making money but not fulfilled by my work. Newly married, my wife gave me tacit approval, and I-Fi Promotions was born.
I worked 3–4 nights a week for a year promoting events and never saw a dollar profit. After promoting a huge, failed festival where we lost 44k, and I personally lost 12k, my dream of being a promoter faded. My 5th business was an abject failure.
After making deep six-figure W2 money for a few years in the mortgage industry in the mid-2000s, everything nosedived during the mortgage meltdown of 2007–2008. The company I worked for was owned by debt-beleaguered AIG and shuttered. My best broker-client hired me to start their commercial mortgage division, which seemed like a terrific opportunity.
However, the entire lending industry seized up, and I worked for four months without seeing a single paycheck. I dressed in a suit daily, working in a beautiful corner office, but the financial world went into a deep freeze. After toiling fruitlessly for four months, I closed one small commercial loan yielding me a grand total of $2600 before tax.
Although I was just a tiny cog in a massive lending machine, part of me felt responsible for the lending meltdown that brought the entire American economy to its knees in 2008. I felt slimy that I was in the middle of the financial collapse as a wholesale Account Executive buying subprime mortgages from brokers, many of which certainly went into foreclosure. Personally, I was building my dream house while all of this was going on, and I could foresee my own financial demise. I was crestfallen.
Working as a loan officer making about 4k/month was not sustainable given my obligations, including child support. I wanted to leave the sleazy mortgage industry behind and do something different.
James called me one day and told me to turn on NPR. I did so and listened to a long segment about the emerging energy conservation sector. I care about addressing climate change, and the idea of doing something positive for the environment in an emerging niche market was exciting.
Additionally, my good friend from college, Samson, was also struggling. He worked in engineering and kept getting laid off since the construction industry had ground to a halt. I told him about the opportunity, and he was interested.
We utilized the SBA business plan template and spent six months diligently working through the details of our business model and projection numbers. We were to perform energy audits to identify where a home is losing energy, and then we’d fix the problems.
We borrowed 30k from our mutual friend Cale and procured a 12k SBA microloan for a business startup through the Obama stimulus plan. The only catch was that Samson’s credit was garbage, so I had to sign for the loan.
I quit my loan officer gig and put everything into the new company. We performed our first job on March 30th, 2010, and my 6th business was born — Energy Efficiency Systems (EES). President Obama pushed significant federal monies into incentivizing energy efficiency, and this helped our young business get off the ground very quickly. After five years, we had ten employees, six ratty company vehicles, and we were doing just under 1mill/year in sales.
We learned our craft and became the top-rated weatherization company in the Atlanta market. Georgia Power gave us the “Contractor of the Year” award in 2014. We built a terrific reputation amongst homeowners for fixing weatherization problems, and the phone rang constantly. Samson and I were only making about 55k/year by then, but we were in high demand and knew the business had legs. We were both tickled pink as the nation emerged from the recession. The future looked bright.
Until it didn’t.
With my sales background and office experience, I ran the front end of the business. Samson was super handy and clever with a deep construction background, and he was to oversee production on all jobs. He was a dedicated father of two young kids, and family came first — along with his tame but reliable social life at several local bars.
Samson used the company debit card for his personal expenses whenever he saw fit. When I queried on our business bank account website, the name of Samson’s favorite Atlanta bar, “97 Estoria”, >$2000 in charges came up in the most recent year, which was supposed to be business expenses. He was my buddy since college and a genuinely good guy, but Samson refused to pay his bills, and as a 50/50 partner, he did what he wanted.
This included purchasing a 1970 antique truck saying it was a work vehicle which was ridiculous. Samson had never had a credit card before, and having the company debit and credit cards empowered him — and pissed me off. His wasteful expenditures were sucking the profit out of the business. This was a significant point of contention.
Samson did very little work, refused to fix his perennially shitty credit, and made multiple daily visits to the bar. Clients often smelled the liquor on his breath.
The tension between the two of us escalated. We had been close friends for over 25yrs, but now we were business partners with our fiscal futures intertwined. Our friendship dynamic changed, and our relationship became contentious.
Our employees had several car accidents, which drove up our already high insurance costs. When we came short of covering our 15k-ish bi-weekly payroll, we borrowed money at a high-interest rate to keep things rolling. (When I say “we,” I actually mean “me” since Samson’s credit was such a mess — even though we were both compensated as equal partners.)
The high-interest loan would auto deduct a hefty daily payment from our company checking account each business day for up to a year. This crimped our cash flow, and then we’d get in a jam again and roll the loan into another high-interest predatory style loan. If we didn’t pay our hand-to-mouth employees in time, they would leave us, and our business would collapse.
We found ourselves in a death spiral of high-interest debt.
Rather than spending 200k/yr on spray foam insulation subcontractors, we decided to finance our own spray foam rig and do the work in-house to improve our profit margin. This added a lot of labor and material costs to manage, and my partner Samson seemed to have checked out. He called in sick frequently or would be doing errands for his mother-in-law or just go on a kayaking trip in the middle of the week if it struck his fancy.
I would often find myself scrambling to make payroll the next day while he was cavorting with the employees and friends at the bar. He had nothing on the line and seemed to stop caring. In contrast, I was working 10–12hrs/day and was highly stressed.
CREDIT IS IMPORTANT — DO NOT GO INTO BUSINESS WITH SOMEONE WHO DOESN’T PAY THEIR BILLS.
I was finally an actual business owner, and this shit SUCKED ASS!
I used to be a W2 employee daydreaming about becoming an employer. Then I found myself as an employer daydreaming about being a W2 employee.
Then we were sued — twice! One homeowner was convinced the smell of the spray foam insulation was making her sick. Another client’s 2yr old daughter vomited one time, a week after our foam application. The couple moved out immediately, blaming our foam application for the vomit.
The legal fees piled up quickly and exacerbated our already dire financial situation.
After nine years in business with Samson, everything built to a crescendo including over 300k in debt that was in the company name with my personal name behind it. I thought that building a business that would amass equity after almost a decade of hard work. Instead, I built up colossal liability.
EES collapsed under its own weight in August of 2019 and took my personal credit down with it. My personal animus towards Samson festered. He walked away without a scratch while I had to file for Bankruptcy. Our 30yr friendship came to an end. My 6th business was yet another failure.
After deep and solemn introspection, I figured out a way to salvage the nine years of work I had put into the old company. Our customers still loved us, and our online reputation was second to none in our market. We were very good at what we did — we just weren’t profitable. Our builder business was also strong, and there were not many other companies in the Atlanta market with our expertise.
I convinced a well-positioned colleague to start up a business with only a slight name deviation from the old EES, and I would run and manage the company, and he would pocket 35% of the profit. My 7th business Energy Conservation Systems (ECS), was born. We only perform testing, which keeps overhead and labor costs low and easy to manage. The strategy worked, and our customers just viewed this as a name change. Business was brisk, and we didn’t lose a beat.
COVID hit six months later, and we managed to weather the storm. One year later, I borrowed 20k from a good friend and bought out my business partner. Now it’s three years later, and I have no business partner to share profits or decision-making.
I’ve learned some important lessons through my many mistakes in business for myself over the years. In the past, I would take any job that came my way. Now, I only take profitable jobs. I don’t borrow money and pay my bills as soon as they come in. I’m still learning to be a business owner, but I think I’m more clear-eyed now and starting to get the hang of it. I’m optimistic that this business will feed me for the rest of my life.
The appeal of running my own business is not just the autonomy of being my own boss. It’s about the opportunity to create something big and then profits from my inventiveness and hard work. There is always a possibility that I will hit it big. The unbridled potential is what keeps me excited and engaged.
I watch the entrepreneurs on Shark Tank, and I get jealous. Entrepreneurship seems to come easy for some people — it has not been like that for me. After running seven businesses over the past thirty years, I’ve seen much more failure than success.
I’m 49yrs old, and I have no superior to answer to. I have ambitious professional goals and still have fire in my belly. Some people call this entrepreneurial spirit.
