The Web Dude Story

Jun 1, 2011 | About Me

By: Jarrod "Jay" Skeggs

By: Jarrod "Jay" Skeggs

Founder & CEO

Behind every business is a story. Some are great and inspirational, some are not. Whether my story inspires you or not is probably dependent on where you’re at in life and whether or not you own and operate your own business. Regardless, I hope my story inspires you in some way. And if it does, leave me a comment below and let me know how.

[toggle title_open=”Read the Short Version” title_closed=”Read the Short Version” hide=”yes” border=”no” style=”white” excerpt_length=”0″ read_more_text=”Read More” read_less_text=”Read Less” include_excerpt_html=”no”]Got Fired. Thought about what to do. Started a Business with a friend. Sold my house and moved me and my family into parents basement for 2 years. Paid off $50,000 plus in debt. Finally found success. Sold part of the business I started with my friend. Friend and I decided to go different directions in business. Started up The Web Dude.[/toggle]

The Beginning

It all began quite a while back, on February 5, 2006. No, that’s not the day I started The Web Dude or even the day I decided to go into business for myself. Rather, it was the day that I arrived at my corporate job as usual, to quickly realize that on this day, nothing was as usual. My email wasn’t working, I couldn’t access the company CRM system. I checked my voice mail, and oddly, I had received no messages over the weekend.

I very quickly added up in my mind, the events of the meeting that was held the previous Friday, along with the strange happenings I had experienced upon my arrival to work and concluded… They are letting me go. I decided to perform one more quick check to make sure. I rang my assistant’s phone and asked her if she had email service and access to the company CRM. She replied with an affirmative. It was then I was sure that a new chapter in my life was about to begin.

I’m not one to delay the inevitable, so, when I saw the Vice President pass by my office, I popped up out of my chair, walked out to him in the hall, wished him a good morning and told him that I felt like this was going to be the best day ever. Interestingly, he avoided direct eye contact and seemed a bit nervous. I walked with him back to his office, and asked if he had a moment to chat. He replied with an uneasy, “Sure”. We both walked into his office. I closed the door behind us, and simply asked, “Can we go ahead and get this over with?”. He looked at me with a bit of an unsure look and asked, “Get what over with?”. I smiled with my best, ‘come on dude, you know what I’m talking about‘, smile and replied with, “You guys are letting me go, right? Would you mind coming up to my office so I can gather my belongings and head on out. I have an 11:00 a.m. tee time and they don’t like it when I’m late.”

Quite taken aback, my boss, the VP, was all but speechless for what seemed like 10 minutes, but I’m sure it was actually only a few seconds. “How did you find out about this? This is not the way it was supposed to happen.” This was about all he could say at that very moment. I explained to him the obvious signs and he then made it clear to me that he fought, tooth and nail, till nearly 9:00 p.m. the previous Friday evening to try and convince the CEO to place me in another position instead of letting me go. I expressed my gratitude for his efforts. We walked up to my office, I packed my belongings, and embarked upon what has proven the be the most enjoyable roller coaster ride I’ve ever taken.

The Unknown

So begins the story of how I became The Web Dude. In the days, weeks and months to follow, I did a lot of pondering, planning, and praying. During this time a life-long friend of mine, Kevin Gilbert, was working a job that he absolutely hated. He had a vision for a potential business. A business that offered services like helping churches, non-profits, and even small businesses learn and understand the craft of podcasting. Kevin possessed the technical skills, capabilities, and knowledge we needed to offer these services, and I possessed the sales and marketing expertise required to acquire clients.

After a little more pondering, planning and praying, we together formed Digital Design Solutions. To be honest, we floundered, flopped, dillied, dallied, and chased practically every single rabbit that jumped within 100 yards of our path for quite a while. All with the mindset and belief that there was a market for “helping” people with every new thing we came across. And there was a market for it; a very limited market, but a market nonetheless. After nearly a year of floundering, bootstrapping out of our own pockets, and making very little money, (ok, making NO money), we realized and understood that at the crux of what we wanted to offer in the way of podcasting consulting, was this company out of Cupertino, California known as Apple, Inc. And they were driving probably 95% of the innovation behind podcasting. Based on that, and based on the fact that both Kevin and I had been Apple users for more than 30 years combined, we decided that a sure fire way to actually make money and become successful was to become tried and true, Apple Consultants. Finally, after nearly a year of poking the box, we actually knew what our business had to offer.

Fish or Cut Bait

It was about this time, roughly February of 2007, that my family and I had a really big decision to make. A full year with no income. And as a result, the accumulation a lot of additional debt. My wife had already made the decision to return to the teaching profession. She had been a stay-at-home mom since 1997 when our son was born. But the time had come to decide whether I would continue to “Fish” or whether I was going to fold things up, pat myself on the back for giving entrepreneurship a good run, and find J-O-B, aka, “Cut Bait”. We had depleted all of our savings, and we weren’t sure how we would pay our next house payment. I was making some sales for our newly founded venture, but not enough to support my family. And nowhere near enough to support two families, which is why Kevin was still working at the full-time job that he hated and helping me at night and on the weekends.

As crazy as it sounded, I knew what the right answer was. It was the hard answer. I was the risky answer. The answer was to “Fish”. Keep it up. We were gaining some momentum and had a couple of accounts that were very close to signing up with us. However, my family and I had to figure out how we were going to make it till revenue was enough to support us. It always seems that with answers, more questions follow huh?

The Sacrifice

My wife and I talked heart-to-heart about our options for survival. For maintaining the great credit score we’d worked so hard to attain. How were we going to make this work because we believed fully that God lead us to this answer. And with that, God also lead us to the answer of How we would make it work.

At 36 years of age, married with a wife and 2 children who were 10 and 7 years old at the time, we decided to sell our house, and much of our material possessions, and live in my parents basement. Our plan was to live there while building up a business and paying off our debt.

Keep in mind, this was early Spring of 2007. The housing market had been steadily declining and real estate inventory was at an all-time high. We knew we needed to sell our house, and we knew there was no way we could afford a Real Estate Agent. However, within view of our front yard, there were 4 homes on the market, listed with Real Estate Agents. So what did we do? We put a For Sale By Owner sign in our front yard. And at the bottom of that sign in big, bold letters it said, AGENTS WELCOME 2.5% COMMISSION.

Our house was under contract within 28 days of putting the sign in the yard. The buyer was brought to us by an Agent who was showing the house 2 doors up the street. I wish I could take credit for the sign idea, but I must be honest, it came straight from God.

We moved into my gracious parents basement on April 28, 2007. My mission was clear and precise. First, attack my families debt, in excess of $50,000, with every spare penny we could scrape up. Second, sign on clients and become a profitable business. I knew that the achievement of these two goals would ultimately lead us to a great deal of freedom and accomplishment as a family.

You did what?

As I mentioned earlier, Kevin and I decided after nearly a year of floundering that we would offer Apple Consulting Services. I’m not afraid to admit that it took me two attempts at taking the certification test to pass. Yes, this means that I failed the first time. One thing I’ve learned over the past few years though is that failure is a good thing; it’s also temporary. On May 29, 2007, I officially passed my first Apple Certification test, which is a pre-requisite for joining the Apple Consultants Network. I joined shortly thereafter and Kevin and I were off to the races.

As 2007 progressed, we landed our first BIG client and got our first really BIG Apple Project underway in late fall. At this point in time, Kevin was still working his regular, good paying, full-time job. He still hated it. In fact, he hated it more and more every single day. We began discussing his transition of leaving his regular job and joining me full-time. The idea being two can grow a business better than one.

We together did some pondering, planning, and praying. We mapped out how things would work and when the right time would be for Kevin to make the transition official. There were a number of things that needed to be put in place financially and logistically. In the midst of working these things through one afternoon I got a phone call from Kevin. I’ll never forget his words…

Well, I hope you’re ready. I just gave my two week notice.

I thought to myself, “You did what?” The truth is, I wasn’t ready. The business wasn’t ready. And frankly, I’m pretty sure Kevin would admit that he wasn’t ready. But whether we were ready or not, his notice was official, and on January 11, 2008, Kevin and I joined forces together full-time.

Holy Cow, it worked!

Kevin and I built a nice steady Apple Consulting business from the ground up. It took a bit of time but by the end of 2008 and into early 2009 we’d finally “arrived”. We had acquired several quality clients that we did lots of regular work for on a monthly basis. Kevin was supporting his family. I was supporting my family by attacking debt and saving money every month as well.

Along the way, back in early 2008, right after Kevin joined in full-time, one of the things that we decided to do was build a better website. By this time we’d both become quite technically adept and decided that we could probably do this ourselves. We explored several platform options for building our website. And after a bit of comparison, we settled on a platform called WordPress. The big factors that drew us in were the price, (It’s forever FREE and owned by the community at large), scalability, and ease of customization.

As we worked together to build our website, we realized quickly that there was likely a market for building and creating websites for many of our clients using the WordPress platform for them as well. As we learned the ins and outs of WordPress and became comfortable with our custom coding abilities, we began pitching our website services to some of our clients for whom we’d been doing Apple Consulting. We signed a few folks on for our website services and as we worked on their web projects we began to realize something. We positively enjoyed every minute we spent building websites, but the time we spent troubleshooting Apple IT Networks, well, we really didn’t enjoy it. Almost instantly we really wanted to spend as much time as we could building websites and as little time as possible doing Apple Consulting. One problem though, we had a lot of steady revenue coming from the Apple Consulting and not so much coming from building websites.

Goodbye Basement, Hello Home

In the Spring of 2009, on April 28, exactly 2 years to the day after we had moved into my parents basement, my family and I moved into our new home in Flowery Branch, GA. Our sacrifice was worth it, and we ended up buying our home for $45,000 less than original asking price due to the market downturn in Real Estate.

Apple Consulting or Web Design and Consulting?

During the late Summer of 2009, we really began going after website business heavily. Kevin and I were pretty sure we wanted to pursue Web Design and Consulting with 100% of our time, but we had to find a way to transition out of our Apple Consulting business. We talked with other consultants about letting them serve our clients, splitting fees, and such, but it seemed like everyone was either not interested in taking action or too busy with existing business.

Then, one day out of the blue, we got a call from an Apple Consulting firm out of California. They were by far the biggest Apple Consulting firm in the U.S. and more importantly, they were interested in buying an Apple Consulting practice in the Southeastern United States Market. We negotiated for a couple of months and finally in late 2009, we signed an agreement and sold them the Apple Consulting part of our business. Finally, we could focus on Web Design and Consulting.

Web, Web, and more Web

With nearly a couple of years of Web experience under our belt at this point in time, we began really honing our craft and gaining some good traction. We were still working with a number of clients for whom we’d done Apple Consulting work and we were acquiring new clients at a very steady pace.

After completing a large healthcare project, Kevin and I began to discuss what markets we should pursue in the future and we felt that perhaps some focus was in order. Interestingly, we didn’t see eye-to-eye on this. Kevin, really wanted to follow his heart, and work with ministries and non-profits helping them deliver their message and gain traction with their market. While I wasn’t opposed to that, I really embrace the challenge of lead generation and conversion and really wanted to focus more on helping small businesses with web marketing. For the time being, we agreed that we would somewhat focus on both, and ultimately, made some good strides in each of these areas.

The Split

As we continued working together, Kevin and I realized, what we were really doing was not so much “working together” but rather, sharing resources. We have our own web hosting company, and numerous subscriptions to loads of web resources. But ultimately, we really seek out and work with our own clients respectively.

About a month ago, we both realized that in order to really reach our goals and be able to focus on what we really enjoy doing for clients, that it made sense to continue to share resources, but it also made sense to start our own businesses individually so we could pursue the things that are rooted deep in our hearts. We still work together and are best of friends. (Did I mention we’ve known each other for 34 years? Yeah, long time).

The End Beginning

So, that’s the LONG story about how and why I am now operating as The Web Dude. If you’ve read this far, your obviously interested in learning a bit more about me, and frankly, you should probably get some sort of reward. And for that matter, you will, if our paths ever cross. I’m helping a lot of small businesses make a lot of money in a down economy by doing web marketing that is tailored to their business and the markets they serve. I am The Web Dude, and I’d appreciate the opportunity to help your business do the same. Let’s talk

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