After two years of writing daily articles, I’m taking a little break to finish some other projects (a book and a small startup, among other things) and working on a long overdue redesign of Dissociated Press. While I do so, I thought I’d share some thoughts about how NOT to create, develop, and maintain a site. We’ll be back with fresh daily linkage and pithy commentary sometime soon, perhaps on a new domain.

How To Not Get Rich Developing A Web Site

1.) Don’t Get Too Clever With The Brand

When you’re naming a media property, you want something clever and catchy, but not too clever. While “Dissociated Press” is indeed a kind of clever name, it in fact fails six ways to Sunday. One of the more amusing things I learned over time was that the people who were most likely to appreciate the name were also the most likely to remember it incorrectly, constantly changing “dissociated” to “disassociated”. For the record, most dictionaries list the latter as an alternate form. But that’s irrelevant. The name is hard to remember, and can’t be turned into a verb like “googling” or “twittering” or otherwise be repurposed easily. And I honestly had no idea what “dp” meant to a lot of people. Yikes.

2.) Stay “White Hat” With The SEO

Early on I generated remarkable traffic and reasonable site revenue with some slightly sketchy search engine strategies. The downside? The site seemed to get “sandboxed” for a while, and has never recaptured the same same volume of visitors. This is actually a no-brainer, but I wanted to see the results of this kind of strategy firsthand. If you’re interested, the site went from zero visitors on June 11, 2008 to nearly 200,000 page views by December of the same year. And then promptly disappeared almost completely from all three major search engines. As of this writing, there are about 30,000 page views monthly, and although that has been increasing, it is increasing verrrrry slowly.

3.) Alternately, Don’t Rely Entirely On Organic Search Traffic

On the other hand, unless your site has very narrowly focused content, and some likelihood of high quality inbound links, don’t rely on simply coding and keywording the site well. Get out there and promote it in every way imaginable. If you don’t use sites like Digg, StumbleUpon, Reddit, or other sharing sites, tap into your friends who do. Or solicit links from sites that rank for content related to yours. I have done neither, and I’m seeing the lackluster results of relying solely on organic search results.

4.) Use The Usability Knowledge That You Possess

When creating the original layout for the site, I did something remarkably stupid, in spite of knowing better. And paid for it. Or rather didn’t get paid because of it. The original design I used for almost two years presented daily posts in different categories on the front page. The newest article was always at the top, under a heading that said “Featured Today”, but the articles were arranged vertically, so people CONSTANTLY assumed that the site wasn’t updated daily, because they simply assumed the site was a “blog” with posts descending down the page in date order. A painful reminder of the fact that PEOPLE SEE WHAT THEY WANT AND EXPECT TO SEE, not what’s right in front of them. In a decade of web development, I’ve watched people constantly do things like clicking on the word they want to be a link, in spite of it clearly not being a link. And yet I want to believe that “the user” is not a numbnut. Accept it. The user is a numbnut.

5.) Polite Placement of Ad Content?

In the original design, I placed almost all the ad content in sidebars, as a courtesy to the user. I assumed people would occasionally click on ads as a courtesy. HAHAHAHAHA! That’s really, really stupid. I won’t resort to popups that make you click ads by accident or other fishy methods like those annoying “hover ads” that many sites torture us with, but POLITE AD PLACEMENT? What does that even mean? Stick ‘em in there baby, and use the heatmap. You’ll notice that the current layout uses the maximum allowable AdSense ads, placed in standard hotspots.

6.) Fresh Quality Content vs Promotion & Marketing

If you’re working alone, and are forced to make a decision between consistently fresh quality content and marketing, maintain a balance, and favor the marketing a little. The truth is that unless you have marketed the site and know that you have regular visitors from a specific source, your search engine traffic will comprise the bulk of your visitors, and they will have NO IDEA whether you update daily, and won’t care. Spend six months building up some quality content, then MARKET, MARKET, MARKET. When you get the traffic up to a respectable volume, you’ll actually be generating enough revenue that you can afford to write every day. Until then you’re just an underpaid writer, and there’s nothing dumber than being independently broke. I’m kind of an expert on that topic. Trust me.

7.) Quit If It’s Failing

Take the advice of people like Seth Godin and quit when it makes sense . And then follow the lead of people like Wikipedia founder Jimmy Wales and fail quickly and successfully. I’ll be back to let you know if my failure succeeds.

Here are Jimmy Wales’ theories of failure:

Fail faster. If a project is doomed, shut it down quickly.
Don’t tie your ego to any one project. If it stumbles, you’ll be unable to move forward.
Real entrepreneurs fail.
Fail a lot. But enjoy yourself along the way.
If you handle these things well, “you will succeed.”