I’ve been trying to make money as an entrepreneur for most of my life now ever since my first adventure in junior high school when I began buying Pokemon card packs and reselling them on eBay to people for triple the $3 price I paid (see my about me story). My best sale was for $25 on a pack I bought for $3 at the card game store. I still can’t comprehend how that worked but knowing there were so many idiots out in the world struck a chord deep within me – How do I extract as much money from idiots willing to part with their money? And with this guiding principle in hand I set out on more money making journeys. Not everything has worked out as well as I had anticipated and what follows are my top 7 worst websites ever created:

1. Investing in Drugstore.com stock

Like George from Seinfeld I set out to “make a big score,” but not by investing my library money in art – instead I reinvested the money I made selling Pokemon card packs in Drugstore.com stock at $43 a share. I lost a couple thousand dollars when the stock fell to a few dollars a share as the rest of the internet stocks crashed. While this isn’t quite a website I created in an attempt to make money online it is what helped to lead me down the path to try earning money online by making websites and not investing in them on the stock market.

Lesson 1: Don’t invest in the stock market unless you know what you’re doing. Extra Credit: If everyone in the country is talking about how you should jump in on a trend right now you know the bubble is about to burst.

More failures and lessons learned are continued after the break…

2. ClassicNES.com

This was the very first website I tried creating back in 2003. It’s done entirely in HTML and tables. This is the best version of it so you can see the crap I created. I learned a valuable lesson with this website because not only was it my first attempt to make a website I also bought the hosting for 12 months and got the domain for free. Little did I know that when the hosting company fell apart 9 months later they took my domain name as well.

Lesson 2: Buy domain names through a reputable company apart from your web hosting provider.

3. NESGaming.com

After losing my ClassicNES.com domain name I decided to buy another one and try again with NESgaming.com. I didn’t learn my lesson with improving the quality when I first rebuilt the site as evidenced by this old version. Yes if you wait long enough for it to load that’s a character from Mike Tyson’s punchout saying “When I’m not tanning I’m at NESgaming.com.” Soon after this fail I decided that I needed to improve the quality of the website. I moved to vBulletin and paid for a professional skin and the result was this. After about 6 months (maybe more) I realized that this was not going to be the best way to make money online.

Lesson 3: In order to make money online a website needs to look better than a circa 1997 GeoCities web page. Extra Credit: People don’t care enough about an old video game system from the 1980’s to bother talking about it in a forum.

4. GamingVidz.com

Based on the lessons I learned from my first website creations I decided that I should try a forum in an area that would be ever changing – current generation video games. As I’ve shared in my about page this was one of the first websites where I got a taste for earning money online, but even at it’s height of 500,000 page views a month I was only earning $500 a month at best. I also spent a lot of time every day managing the forum and dealing with trouble makers.

Lesson 4: If I’m not earning enough money from one website, then I should start more websites.

5. WorldofWarcraftBoard.com, XboxLiveArcade.com, HaloBoards.com

Even though I was only earning $500 per month at the peak of popularity for GamingVidz.com I decided what I needed was more video game forums so that I could earn more money on other websites at the same time. So I set out to create more video game forums. The problem I faced now was that managing even more forums in a niche where members are always getting into arguments and causing trouble due to their maturity level. So instead of making more money I just buckled under the work load and the communities slowly suffered.

Lesson 5: More websites is not always the answer, especially if you stay in the same general low paying niche.

6. BestArcade.info

Not content to try earning money off video game forums I decided to branch out and try a video game arcade. I liked the idea of setting up the website once and the only time I’d have to spend on it later would be promotion. The problems I faced were all too familiar – video games are a low paying niche and despite the fact that I didn’t have to work on the website daily it still didn’t earn enough money to warrant the effort.

Lesson 6: As much as I love video games, it’s time to branch outside of my bubble if I want to try and earn a solid income online

7. ChrisGuthrie.net

After spending a lot of time researching how to make money online I came across the internet marketing niche. I figured that although I wasn’t making a full time income online I have a lot of experience building websites and trying to earn money from them that I should start a blog about my adventures of earning money online. I spent about a year and a half blogging on this domain name and never earned more than a few hundred dollars per month.

Lesson 7: Just because someone else can make money blogging about how much money they make online doesn’t mean I can.


Most of my early time spent building websites was more about having fun and learning. As this desire for having fun transitioned towards making money I took too long to venture out of the comfort of the over saturated niche I knew so well: video games. It wasn’t until a year of blogging on ChrisGuthrie.net later that I started truly branching out into other niches on the web and only after doing that I started earning good money. As the money I earned from these websites grew I started to blog less and less on ChrisGuthrie.net. Then in late 2009 after losing my job and already earning enough money from my websites to support my family, I decided that I wanted to return to the internet marketing niche offering the perspective of a full time internet entrepreneur so that I could share all that I learned. So I bought a new domain name that more accurately described the purpose of my blog and started writing again in early 2010. My goal for this blog is to cut through the misinformation that is spread all over the web on how to make money online and to teach you through examples how I make several thousand dollars per month. I hope you come along for the journey.