How I Accidentally Became An Entrepreneur

Joshua Davidson
Feb 12, 2019 · 10 min read

The following is an edited excerpt from The Entrepreneur’s Framework: How Businesses Are Adapting in the New Economy by Joshua H. Davidson.

In a lot of ways, I owe the worst economic climate as one of the contributing factors to becoming an entrepreneur.

Without facing one of the hardest, most depressing times of my life during my most impressionable years, there is a chance I would not be where I am today. You probably recognize this period of time as the Great Recession that hit the globe hard from 2008–2009.

Where I grew up, our local economy was heavily impacted by the city next door: Atlantic City, New Jersey. Almost everyone in my hometown worked in Atlantic City, or had a job directly tied to the city’s success. For those who are unfamiliar with Atlantic City, the best way to describe it is as a hand-me-down version of Las Vegas on the beach.

During a recession, one of the very first things that individuals cut out of their daily expenses are the non-essentials, such as entertainment. Unfortunately, Atlantic City and our entire local economy was based on that one industry alone. Once people could no longer afford their mortgages and necessities in life, visits to Atlantic City were quickly deducted from their expenses. Why gamble away whatever little you have left when you had so much debt and limited disposable income?

Soon after, as one can easily expect, casinos began to cut any “non-essential expenses” they could spare, which meant massive layoffs and soon, full-on closures. Entertainers, executives, dealers, servers, cleaners, cooks, customer service representatives, any job you could think of, all faced the same harsh reality. It seemed like everyone was out of a job, and would be for a long time.

I can still remember hearing from some of my closest childhood friends that their parents had foreclosed on their homes. I can still see some of the local businesses I grew up with closing up shop, as our town’s population began to shrink. I will never forget my father working three different jobs at one point to support our struggling family.

At the time, I was your stereotypical, average suburban sixteen-year-old

For some reason, I thought that having the longest hair possible without needing to brush it was fashionable. My clothing of choice was jeans and a zip-up hoodie that was always one size larger than it should have been. My only real possessions were my laptop (which started as a family laptop, and within a few weeks became mine exclusively) and a digital camera that was given to me as a birthday gift a year earlier.

Except for school and working as a busboy at the local Red Robin, the majority of my time was spent chatting in online forums (or message boards, as they were known then). I first stumbled upon AOL chat rooms and AOHell (a popular AOL hacking tool) in the mid-90s. Then came Yahoo GeoCities in the late 90s, Macromedia (now Adobe) Fireworks, MySpace layouts, and finally, message boards in the early 2000s.

I loved interacting with people online, and it was through these experiences that I learned my calling was making things for other people. When I was twelve or thirteen years old, I created a fan site for my favorite local theme park, Six Flags Great Adventure in Jackson, New Jersey. This not only became the most popular theme park fan site on the Internet at its prime, but replaced Six Flags as the number one search result in the early days of Google. By the time I turned sixteen, I knew I wanted to create something that was digital, and make some actual money doing it.

Still, I wouldn’t characterize this as wanting to be an entrepreneur; not yet. It was a mixture of being a naive teenager wanting to demonstrate my own independence, while also doing something that I deeply enjoyed (unlike working as a busboy at the local Red Robin).

The very first moment that led to my accidental entrepreneurship

It was mid-July 2009, in the later part of the morning, and I was spending time in the basement of one of my childhood best friends, Kegan Gilbert. We initially became friends out of proximity — he was the only friend I could walk to without having to beg one of my parents to drive me over to his house as we both lived on the same street — but later bonded over our love for computers, software, websites, and message boards. As Kegan played Castle Crashers on his Xbox, I mindlessly browsed the Internet, trying to think: What should I do? What could I do? What could I be good at?

Sometimes a random thought just pops into your head. You could be taking a walk, you could be reading a book…anything. And that random thought can spark a firework in your head. This happened to me while I was aimlessly browsing the Internet that day. I started thinking… do any of the local businesses in our area have websites? I tried searching online for all of the local businesses I knew around my town and couldn’t find anything. Except for a basic landing page every now and then, not a single small business had a website of their own. It’s hard to believe now, but it wasn’t normal for a small local business to have their own website back then. And then it suddenly clicked. I realized I could make websites for the local businesses I thought needed one (which to me, was automatically everyone who didn’t have one).

When a firework lights off in my brain I become — at least briefly — uncontrollably obsessed with the idea. It’s something that has carried over the years — my team at Chop Dawg can tell you it is both my most wonderful and annoying trait.

I looked for domain names to register. Kegan joined me and we debated over names for a solid hour. I wanted the name Chop Shop — I wanted something to sound “bad ass.” He kept pushing “Top Dog,” as a way to clearly communicate to customers who is the best. We kept going back and forth until we compromised.

“How about Chop Dog?”

“Yeah, that sounds good.”

It turned out ‘Chop Dog’ wasn’t available to purchase as a domain name, but another similar name was: Chop Dawg.

As a sixteen-year-old, I liked the wordplay. Kegan also liked it because it would only make the company stand out further from the crowd. It helped too that where we grew up in New Jersey many people had a slight accent where when they pronounced ‘dog,’ it came out ‘dawg’ anyways.

One click of the computer mouse later, and, the very same company that I run today, was born.

At that moment, without even realizing it, I became an accidental entrepreneur.

Now I needed my first customer…

If you haven’t visited New Jersey in the summertime, let me paint a picture for you. First, it is hot. Quite hot. You’re looking at temperatures between the high 80s and low 100s. Second, it is humid. Within five to ten minutes of being outside, you’re covered in a gallon of sweat. It isn’t the most pleasant of experiences, to put it lightly.

Unfortunately for my sixteen-year-old self, I didn’t have the luxury of driving around in an air-conditioned car to deliver my pitch to the local businesses. Instead, I walked. And keep in mind, this isn’t the city life where everything is walking distance. This is the suburban life, where you would walk miles to your nearest shopping center as it was intended for you to drive to.

Kegan would usually tag along for moral support. I also hoped with him being slightly older than me, that these business owners would take us more seriously. Unfortunately for me, Kegan looked younger than his age. Oh well, at least I had the company on those long, sweltering summer days.

Every morning, we would leave my house around 9:00 AM (the time most local businesses opened up) and visit each individual shopping center, going door-to-door to pitch my website design services to these businesses. I was confident they would see I could be a savior to their business in this harsh economic climate.

Imagine a sweaty sixteen-year-old who has no idea how to appropriately dress, walking door to door and asking to speak to the person in charge. He wants to pitch his services, and make his services known. Imagine him somehow getting in front of that person in charge, trying to sell web design for the first time of his life without any proper presentation. Now imagine another teenager following along who just stood there during the pitch, without saying a word. It was an awkward situation every time. Needless to say, I scored zero sales.

In hindsight, there was a ton wrong with my “plan” of attack

It wasn’t just the awkwardness I put these people through that was the big problem. Today, having a website is viewed as an almost necessity. But back in 2009, many small businesses thought of websites as accessories, not necessities.

That mentality, mixed in with a terrible economic climate, meant that almost immediately, everyone mentally dismissed the idea of such an “accessory.” I had many small local business owners kindly explain to me, “I’ve been in business for X years without a website, and I’ve been fine! Why would I need one now?” I honestly couldn’t come up with a defense. To me, a website was a no-brainer. I could not grasp how some people did not feel the need for a website.

Over time, though, I began picking up subtle cues from the business owners I spoke to. I started to identify what they wanted to hear, and what they didn’t. I also started figuring out what type of clothing I should wear to make people want to listen to me — just by changing my attire alone, I had fewer owners pointing at their “do not solicit” signs. I was determined to make this work. I knew, deep down, that I was going to find my first customer. I had the mindset that for every “no” I was hearing, I was getting closer to that first yes. From there, I told myself, the rest would be history.

It’s the one feeling I wish I still had today. Today, even when I am feeling confident, there is always a small voice in my head that has a shred of doubt. It’s because I know I have so much left to go in this journey. On one hand, I love it, as this little shred of doubt keeps me grounded and always working harder. On the other hand, there was something so amazing about that time before becoming jaded by the daily grind. It’s that “naive optimism,” as Treehouse founder Ryan Carson called it. I miss that feeling.

And then, somehow straight out of folklore, something just happened

It was August 31st, 2009, the final day of my summer vacation before junior year of high school began, and Kegan and I were down to the final shopping center. These were the last few businesses in the entire town that I had yet to pitch to. First, there was only five remaining, then four, three, two… finally, I had one shop left before I could say that I officially struck out, spending my entire summer pitching my services that no one wanted.

This last shop was a small pet boutique and grooming service called “It’s a Doggie Dog World.” It was a perfect fit, in my head at least. I remember thinking it was a sign — “They’re all about dogs, and our company has the name ‘Dawg’ in it.” This was obviously meant to be. Kegan thought I was crazy when I said this out loud (he was probably right).

Kegan and I put on that look of confidence we’d gotten accustomed to wearing over the previous month and a half, walked in, and went to the very first employee we could find. There was only one in the entire store, right at the checkout register. As it turned out, he wasn’t an employee, but one of the co-owners of the shop, Michael Baker.

The entire store was painted blue, with red accent walls every few feet and plants laid out. It all set the mood for what the customer could expect when walking in. It was one of the nicest, most put-together small shops we had walked into all summer. Michael was speaking to a customer behind his register and then paused, looked right at us, and asked what we wanted. I explained briefly I wanted to offer him a website, and he immediately said he was with a customer, and that he could talk to us once he was done with her.

We were used to being told no or go away, so this was one of the best responses we ever got. A small victory, already.

I wasn’t going to waste my last at-bat. Once the customer had left the store, which candidly felt like hours (although in reality, was just minutes), I pitched to Michael exactly what I was capable of, why I was the guy for the job, and how I could help his business. In response, Michael began discussing how disappointed he was with his current website, how he couldn’t update it, how it looked terrible and didn’t reflect his store. All of a sudden, I didn’t need to sell myself to him anymore. Having a website was not an accessory for him, he felt it was a necessity too.

I told him I could resolve everything he had mentioned, without any hesitation.

He looked at me, Kegan, then back at me again, asking: How much?

Whoops! I hadn’t thought about how much I’d charge for this as a service. I had been so occupied with finding a paying customer, I didn’t think of the price that I would want anyone to pay. One of the most make or break fundamentals of business was something that I now needed to decide on the fly. I blurted out, “$200.”

I really didn’t know what to charge, or where even to begin. Was $200 too much? Too little? Do small businesses spend $200 on their expenses? $200 was a lot of money, right? How much do small businesses spend a month on expenses?

My mind was still racing when Michael said, “It’s a deal.” He shook my hand and asked how soon I could have something for him. I officially had my first customer.

To learn more about how to succeed as an entrepreneur in the New Economy, pick up The Entrepreneur’s Framework: How Businesses Are Adapting in the New Economy by Joshua H. Davidson.

Joshua Davidson

Written by

CEO of @ChopDawgStudios. A passionate student of entrepreneurship. 📚 Author of The Entrepreneur’s Framework. Speaker, radio & podcast host 📲 Philly sports fan

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade