If you’re a regular reader here then you probably realize that I’m someone who over plans everything, I like MindMaps and Action Sheets for creating blueprints for every step in a project.

In fact, by the time I’m ready to start a project I usually have it so well laid out that I could just hand everything over to a total noobie and feel confident that if they followed the blueprint it will turn out just as well as if I do it all myself.

I do all of that because I like to try and discover and head off any possible potholes in the plan before they arise.

Some call me anal retentive in my process, and it would be fair to assume that someone like me is probably pretty conservative in my business most of the time.

However, those whom I work with and who know me well also see that while I pay extra attention to details when planning out a project, my overall views on business are often a little radical, and I’m actually fond of taking risks by going against the grain.

For example, over the last year there’s been a huge trend towards using membership sites and other paid-for content models among Internet marketers.

A couple of well known marketers created products around these models and tons of other marketers bought into the hype and promises of “all you need is a continuity model”.

I’m not saying continuity sites aren’t worth building, they sure are if you can get a hungry crowd.

The point I’m making is that while the trending has been towards memberships and paid-content models, I’ve been exploring the other direction–and having some impressive (to me at least) results.

So, while lots of marketers have been building niche membership sites and paid-content training courses to sell subscriptions to, I’ve been playing with the Commercial Open Source model and finding ways to apply it to content as well as software.

The basic idea is that if you create a great product, you can give it away free, or as open source, and revenue streams will grow from customizations and support services. A great example of this is WordPress, where the core product is open source, but a lot of designers have made small fortunes on custom themes and many programmers have made good with plugins and widgets.

But, while this model works really well for great software, finding ways to apply it to content is a little harder, and frustrating at times.

The most obvious idea, which is as old as the web itself almost, is simply providing advertiser sponsored content.

That’s actually a great model, but the problem most people and businesses run into with it is two-fold.

First, your content must be paid for up-front, however your returns on the content will be slow and long-term.

For example, if I pay a freelance writer $20 for an article and post it to my site that earns strictly through Google AdSense, then I’m out $20 today and it may take 6 months or longer for that article to accumulate $20 worth of advertising clicks.

Of course, the up-side to that is once you break even, every penny that article earns from then on is pure profit.

In talking about a single article this doesn’t seem like a major obstacle, but for a full-blown content site where you’ll need to publish multiple articles every day the up-front costs for content can add up quickly, yet the returns will remain slow and long-term.

That’s partly why some print publications have had trouble moving online profitably, they’re used to paying for an issue’s content, printing the issue, collecting the cover sales and ad checks and moving onto the next issue. Everything is contained in these short-time windows around each printed issue.

But online where content can last forever, the view can’t be “this month’s revenue must cover this month’s costs”. Because this month’s content can (and should) continue earning revenue for you month after month going forward, so the production costs have to accounted for in that long term revenue stream too.

And that leads into the second major problem many run into, and that’s creating content that is evergreen. This is what trips up most news publishers, as well as many entertainment, gossip, political and other fluid themed sites.

If your site is centered on content that’s going to be “old news” or outdated quickly, then that’s going to cut into your long term revenue capabilities from your content.

However, content that’s evergreen has a longer (or infinite) shelf-life and can continue earning you money for years. An example of this is a small utility program I made about 10 years ago that was just a simple Color Picker for webmasters, it still gets 20+ downloads every day, ten years later, and I still get a few clicks (revenue) from the ads on the download page each week.

That tiny little script that took me about 30 minutes to create 10 years ago has probably earned me several thousand dollars now. That’s the power of evergreen content.

So, I’ve gone a little off-track here, but the point is advertising sponsored content can be a profitable model, and if you’re smart about your content it can continue bringing you revenue for a very long time.

Another smart way to convert free content into revenue is by simply repurposing your free content.

Giving it away free on your site pages (with advertising) is great, but does it meet the needs of every member of your target market?

Do any of them have iPods? Then converting some of your content into podcasts is a great way of repurposing it, and if you build a listening audience up then you can sell in-broadcast advertising with it. Just like you sell in-mailing ads with your weekly/monthly newsletter.

You are sending out newsletters from your site(s), right? If not, there’s another opportunity to repurpose content and deliver it straight to your market’s Inboxes, with their permission of course, and with direct ad sales inside each mailing.

How about videos? With almost no real creative talent at all, you can take the audio of your podcast and mix in some screen shots or stock images to create a neat slideshow video presentation from your existing content.

Publish collections of your content as free eBooks. You can do it as PDF’s, or better yet, turn your content into Windows executables (there’s tons of HTML to EXE converters out there for free), that way you can list the content software in some new places to attract new visitors. — Best is to create both PDF’s and EXE’s from your content to give your visitors every possible option. And again, your eBooks can contain advertising.

The bottom line is if you’re serious about earning revenue by giving your content or products away for free, there are ways to do it. You just have to get your mindset in the right place, and understand that whatever the upfront cost of publishing your content is, the revenue is going to be slow and long-term from each piece–but if you’re creating evergreen content it should work out to be profitable over time.

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