GRRRRREAT question. I've had many failed sites so I'll touch upon a few...
1) Internet Marketing Site
I gave up because the niche was overcrowded and I could never get enough traffic no matter what I did. I could never get over the 150 visitor per day hump for nearly 3 years.
I kept pushing products that helped people make money when I wasn't making money myself. So my content was stale, and pretty much a re-write of what was already out there.
I got very bored. The site stayed around for about 4 years but I was working on other sites at the same time.
2) Reality TV Forum
Big mistake starting off with a forum and no traffic foundation. I tried to use another site I owned to promote it but that site was only getting 200 visits per day and it wasn't enough to keep the forum going.
I only had the site for about 6 months.
3) Soap Opera site
I used to be an avid Days of Our Lives fan so I created a site that focused on the humorous aspects of the show. I had some javascript face warps where people could warp the character's faces with their mouse, etc. but it was very hard to monetize that site because it was visited largely by teens.
Teens don't have a lot of buying power so when I would promote products they never bought. Plus it was really hard to get to know what kind of products to push. Even though I knew my site was largely visited by stay at home moms and teens, I found it was difficult to monetize an entertainment site. (This was before AdSense, by the way)
Traffic was also another issue. I couldn't get over the 200/visitor per day hump. I also got bored with the show and finally stopped watching so of course I had no motivation to keep the site going.
The site lived about 4 years.
This is a wonderful question, Mike.
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