15 Lessons I’ve Learned Working Online For 20 Years

December 28, 1998 was a time when it was unheard of to work online.

The Internet was just beginning to rise in popularity as people were getting online with their dial-up connections using America Online a/k/a AOL (I’m sure you remember the disks they used to send out in the mail).

I actually never planned to “work online” I just wanted to have a website.

The Beginning

This day twenty years ago, I had just received a new Gateway 2000 computer as a Christmas gift from my parents, and wanted to create my own homepage on the Internet that could be viewed across the world.

I was amazed that there was something I could create in my bedroom and it could be viewed anywhere there was an Internet connection.

Being born and raised in a small town in West Virginia, I was in awe that I could actually reach an audience, especially at 13 years old.

Growing up an avid sports fan, I decided I’d make a website dedicated to news about all the different sports.

I spent hour-after-hour learning how I could create this “homepage” and get it published.

Within a few weeks, Geocities.com/~sportsfan13 was born.

Lesson 1 – I Needed My Own Domain

It became obvious that I would need my own domain (i.e. a .com) if I was going to gain an audience.

The URL, Geocities.com/~sportsfan13, was too long and hard for people to remember.

However the problem with registering a domain was the cost of $75 for one year.

Being 13 years old, this was a lot of money, so I had to consider my domain carefully.

Lesson 2 – I Needed To Narrow My Niche

Along with my own domain, I quickly realized it was going to be impossible to cover all the major sports working in my free time.

Even after getting my identical twin Richard involved to help type news, ESPN had severely beaten us to the party, covering all major sports with their massive staff.

In order to gain an audience, I was going to have to narrow my focus to something that was manageable.

Lesson 3 – Learning From My First Failure

Applying my first two lessons, I decided to abandon the sports niche completely, and instead create a website that would help other people start their own website.

Having just gone through months of learning HTML, servers, graphics, and many other trials and tribulations, I figured a website that would help others get through this daunting process would take off.

Therefore in the summer of 1999, I registered my first domain, ProWebResources.com and launched a website:

Screenshot from Archive.org Nov 1999

This is also where I got started offering web hosting as I purchased my first dedicated web server later that year.

Despite working on the website for a year straight, I failed to gain an audience, and decided to once again re-shift my focus:

Given the Internet was still very young I believe I had narrowed my focus to a niche that was not quite large enough. Personally, I believe had I stuck with it a bit longer (patience has never been my strong point) I would have eventually had a very large web hosting company.

Lesson 4 – Go Where The People Are

As you can see in the above screenshot, I left the webmaster resource niche and began covering professional wrestling.

I actually can’t take credit for the “idea” at all; it was all my identical twin brother Richard.

Combining my talents of website creation/server management and his exceptional writing skills, we decided to create a website together that covered the two most popular pro wrestling “federations” WCW and WWF.

If you ever watched pro wrestling in the late 90s/early 2000s you know how “addicting” it was.  I even think it was beating Monday Night Football in ratings!

He had the idea to combine both WCW and WWF into a domain: wcwwwf.com.

Instantly the website was a success!  The first night we registered it we had over 500+ visitors to a coming soon page.  Within the first month we were up to 10,000+ daily unique visitors!

Lesson 5 – Learning To Manage Money

With the rising popularity of our website, we soon found that we needed a lot more funds to fuel the dedicated server costs including really expensive bandwidth.

As luck would have it, we were approached by a company in 2000 called Black Dog Media that was an affiliate of a large organization called UGO.

We struck a deal with them where we would be paid $4 for every 1,000 468×60 banner impressions ($4 CPM):

Screenshot from Archive.org Dec 2000

Very quickly the money started to roll in.

The first contract guaranteed at least $350/month.

By the second or third month we were right around the $4,000/month mark; a lot of money for a couple 14-year-olds! 

This however was put to good use as our server expenses quickly soared to ~$700/month. 

Lesson 6 – Surviving The “Dot Com” Crash

Unfortunately the good times didn’t last long.

Throughout the year 2000, the “dot com bubble” began to burst and by December, we were informed we wouldn’t be paid out on the remainder $5,000 and our contract was cancelled immediately.

With rising popularity and hosting costs we had to immediately begin re-investing all the money we had saved (thankfully we didn’t go on a spending spree).

By mid 2001 my brother and I were both mentally and physically exhausted.

We had spent every waking second (outside of school) working on the website and trying to manage the business.

This also cost us our entire social life; hence we made the decision to sell:

Screenshot from Archive.org May 2001

It was a tough decision, but we really just wanted to get out from under it, and get back to a normal teenage life.

Lesson 7 – Refusing To Give Up

Once the website was sold and teenage life was in full force, my brother and I gained experience working our first “real job” for our father’s local hardware and lumber business.

We quickly realized that working a real job wasn’t near as much fun as working in our bedrooms from home on our own terms.

Creating website was also my “hobby” hence it was something I loved to do.  While money was a factor, it wasn’t about that, it was about spending my time carrying out my passion.

Therefore in the fall of 2002, our senior year of high school, we decided to get back into business.

Unfortunately wcwwwf.com was gone, but we were able to re-acquire WrestlingUnlimited.com from BuyDomains.com.  We had let the domain expire hence had to pay a $500 premium to get it back:

Screenshot from Archive.org Nov 2002

I apologize the above screenshot doesn’t include images, but I felt it was important as it brings me to my next lesson.

Lesson 8 – Diversification

Having lived through the dot com crash we felt it was important to diversify the business so if we lost a single ad contract it didn’t send us back out.

Therefore we decided to startup other businesses, as shown above, a web hosting company.

This would eventually be branded as TheHostRack.com:

Screenshot from Archive.org Oct 2003

Being young and energetic, I thought it would be possible to manage multiple businesses at once.

I actually tried this on more than one occasion, but eventually discovered it was very difficult to manage multiple things at once without sacrificing other parts of life (more on this later).

There are however other ways a single business can be diversified.

Lesson 9 – Having A Backup Plan

Being jolted by the dot com crash I still didn’t have enough confidence to only rely on the diversifications of my businesses.

Early on when I started making money, I begged my parents to allow me to drop out of high school. I felt it was only holding me back and I could do so much more if I could focus on work 100%.

Following the crash in the 2000s, I changed my mind on that and decided to pursue a college education.

With much help and support from my parents, I felt like work was always going to be there, but I only have my youth once.

While it was certainly challenging watching some of my online buddies skip college and go on to create some very large companies, I still don’t think I’d ever go back on this decision.  My college years were some of the best years of my life and helped me develop business and social skills I may never have had otherwise.

Lesson 10 – Trying To Do Too Much At Once

While in college, my online businesses continued to grow; a popular professional wrestling website and a thriving web hosting business.

If I was able to succeed in getting my college diploma, I had to let some of it go.

This became very apparent when I was on Spring Break in 2006 to Las Vegas when I spent my entire first night in the hotel room trying to cleanup a root kit that was installed on one of my servers.

I physically and mentally couldn’t handle running two businesses, going to college, and trying to fit in a social life.  Therefore I made the tough decision to sell off the web hosting company.

Lesson 11 – Maintaining Integrity

When I graduated college in the spring of 2007, I was ready to spread my wings, and make all the money I felt like I missed out on.

While business was good, I had these dreams as aspirations of becoming a billionaire and was willing to do anything and everything to make it happen.

Not only that, I wanted it to come instantly.

As mentioned above, my patience has never been a strong point, and I was willing to stay up day and night to make it happen.

This eventually led me down the path of CPA (cost per acquisition) Affiliate Marketing.

I had read a thread on a popular Internet Marketing forum where I learned of others making millions of dollars by pushing free ringtone offers on Google Adwords.

As an affiliate marketer, you’d signup for an account at an Affiliate Network, get access to the ringtone offers and were paid a heavy commission for each “free trial” started (anywhere from $30 – $70 per trial).

The only problem with this was the end-user thought they were getting something for free, but hidden in the terms, it was actually a recurring subscription.

While many would argue the terms were clearly shown on the landing page (which Google eventually required a checkbox) it wasn’t very straight forward and what was I would consider deceptive marketing.

I would go on to promote hundreds of these offers expanding out into other verticals such as skin care, pay day loans, diet/weight loss, and many more.

Looking back a decade later, this was a very immature decision I made being self consumed into building my own ego and pride.

I thought wealth equaled the power and happiness that every college graduate was “competing” for.

One of the final things I heard one of my business college professors say was to always maintain your integrity because this is all you have.  It makes sense today, but back then, money was my motivator and this is when my online business career took a major turn.

Lesson 12 – Working For Money

Once I got my affiliate operation going full force, I was amazed how I could scale so quickly going from $0 to $1,000s overnight once I hit a winning campaign (the right offer + traffic source) with very little work.

While my other businesses had always made money, this was like taking a shot of steroids before hitting the gym.

As a bonus, since I was an affiliate for a larger company, I didn’t have to worry about billing, customer service, inventory, etc. I just picked an offer and ran wild with it.

I felt like all my other businesses were built in vein and I had been going about it the wrong way.

This became like a drug to me where it was never enough. I was never satisfied with my income, I always wanted more.

Once I hit one goal, I wanted the next, and it started this vicious cycle.

What had started out as this passion to building websites and having them viewed by people across the globe had turned into an addiction to working for money.

While I’m sure many would argue this, but when I was working for the money I felt there was no more passion involved, it was all about the next big goal or the next high I could reach.  This took a severe toll on me personally.

Lesson 13 – Working With Business Partners

While on my wild quest to get rich, I decided I could expand even faster with business partners. 

This wasn’t a bad thing; I met some fantastic and exceptionally talented people that would end up becoming life long friends. 

The only consideration however that has to be made when selecting a business partner is how the relationship works. 

Entering into a business partnership is a lot like entering into a marriage (for those that are married it’s likely you’ll likely relate to this).

Legally the ownership of the business is the % stake agreed upon entering into the partnership.

So for example, many new businesses will just split it half and half.

Say two people go into a business together, one party owns 50% and the other has 50%. 

Therefore not one member has a controlling interest over the company.

What happens if there is a disagreement?

One person wants to take the company in a different direction than the other?

This can arise conflict where some type of mediation has to occur.

What happens if one business partner doesn’t pull the load that you think they should be pulling?

Eventually the honeymoon phase of turning an idea into a company wears off and these real issues have to be addressed; especially after money starts flowing in.

Most of this isn’t considered when you’re wearing the money blinders.  

Thankfully I never had many of these issues but eventually decided business partnerships wasn’t for me.

Being exhausted from constantly chasing the next shiny object to make the most money, I just wanted to get back to my original passion regardless how much money it made.

This was the decision that led up to the foundation of NameHero. 

Lesson 14 – Finding The Perfect Balance

This is something I couldn’t see for a long time.

For a while work was life and life was work.

If work was good, life was good.

If work was bad, life was bad.

I had no balance. I lived to work.

For me, this was an easy trap to get into being young.

Coming out of college I didn’t have a wife, kids, and family so I decided I’d just put all this off until I got rich, because I had the belief that money would buy me happiness.

I know this sounds very clique as I had heard this for many years, but I had to experience it first hand to believe it. 

I had to go down the path of being spiritually bankrupt to see this. 

Today, work is a part of my life, but it’s not my life.

I’m a husband. I’m a father. I’m a brother. I’m a son.

I don’t spend every waking second working nor am I slave to money.

I look at NameHero as an opportunity to be of service to others.

Rather than waking up with the goal of stacking more dollars in my bank account, I look for ways I can be of maximum service to others. 

I get to help our customers get their businesses online by providing training through our Blog and YouTube channel.

I get to restore some faith to the web hosting industry by providing high-speed web hosting with exceptional customer service.

I get to put people and relationships above profits.

I get to share our success with our employees with the goal of our growth blessing them and their families.

Today I have actual start and stop times for my work days where I can then take this same energy and spend it with my family.

Lesson 15 – Getting Out Of The Fast Lane

From my college graduation in 2007 until August of 2014 I lived life in the fast lane.

Not only did I want instant riches, I wanted everything else life had to offer.

This created a fairly wreck-less life style.

One thing they never taught in business school was how to manage life when you start to become successful.  And what even is success in the first place?

Through my 20s I thought life was all about money, power, and partying.

While these experiences taught me a lot of lessons, I don’t believe that to be the case anymore.

I personally see true happiness achieved by living a balanced lifestyle stepping outside of one’s self and being of service to others. 

Along with this comes patience, one thing I’ve always struggled with.

Since 1998 I’ve been part of around 10 different companies, six of which have went on to become multi-million dollar corporations.

While some of them were faster than others, with hard work and dedication, the success will come with patience and learning from failures.

I could have thrown in the towel and number of times and would have missed out on a number of opportunities. 

Final Thoughts

I know this post is completely out of the ordinary than what we normally publish on our blog.

With today making 20 years working online, never having a “real job”, I wanted to share my thoughts and experience to benefit others.

It’s my goal that aspiring Entrepreneurs and other business owners will pull something of value out of the lessons I’ve learned through practical experience.

Being 33 years old, I have no plans on retiring anytime soon, and continue to learn new lessons daily.

If there was anything I could go back and tell my younger self, it would be to remain patient and never sell myself short for the quick buck.

Life is so much more than money.  While it’s a vital tool, a successful business career is measured by so much more.

I’m no rocket scientist nor was I ever top of my graduating class.

I’ve been told a number of times I couldn’t or my goals were to big, but I never accepted it.

I believe anyone anywhere can become a successful Entrepreneur as long as they have willingness and are open to learning from failures.