In other words, Jeff has done a tremendous job at creating a community and audience for his site and podcast, but he hasn’t found a way to make real money off his activities. If you monetize your online activities, you can then justify and devote more time to the activities to establish and grow your community.

But if you can’t make any money, it’s hard to justify spending so much time online. And if you can’t spend the necessary time online to build your community, your site or podcast won’t take off.

Although David was critiquing Jeff, I felt like he could have been equally speaking to me. I listened carefully, waiting for the key ingredient Jeff was missing. What was he not doing? What was he not seeing? How does one move from a hobby site/podcast that has a growing enthusiasm to one that makes enough money to sustain you full time?

I have a few notes, gathered from anecdotes and people I know:

• Just recently Cameron Moll, a well-known web designer whose blog is Authentic Boredom, quit his job and turned to freelance full-time. He sells posters and job listings on his site and does some freelance work, I believe.
• A basketball buddy of mine explained that, according to Jason Van Orden (who creates the Internet Business Mastery podcast), I should be making $1 per month for every follower I have with my site. Translating that, I should be pulling in more than $2,000 + every month.
• My former brother-in-law taught me that information products about making money online are more profitable than selling regular products. He’s an eBay mogul who earns thousands of dollars teaching people how to drop-ship products on eBay. The business of teaching others how to drop-ship is more profitable than actually drop-shipping.
• About a year ago Jane kept prodding me to sell some ads in my sidebar. I finally did, mostly by contacting companies separately and pitching ads, and it worked. But ad revenue doesn’t scale. I only have about 12 spaces there. (By the way, there’s an empty spot, if you’re interested.)

Lately I have been mostly resigned to the idea that “information wants to be free,” and that the real benefit of having a blog or podcast is the capitalization on the attention economy of my audience, as cool and unprofitable as it sounds.

But the other day I was talking with Sean, my brother-in-law (a different one), who is an interactive programmer and runs his own company, HD Interactive. Sean manages a successful online business, so I asked him what I am missing. What is that missing element that I could adjust so that I would be profitable? Create a premium version of the podcast? An online site with video tutorials for WordPress or other software? Sponsored posts? WordPress blog design projects? T-shirts? Webinars? e-books? A forum?

As I talked with Sean, it became clear to me that no single product would provide an online revenue model of the sort I’m searching for. There is no missing ingredient. Rather, the revenue model of the Internet is the Long Tail. Of course! I should have seen it coming.

If you’re unfamiliar with the Long Tail, it’s a model by Wired Magazine’s Chris Anderson and purports that online stores such as Amazon.com make more from long-term sales of their niche products than they do by selling mainstream products. For example, the Grateful Dead Mug from 1979 that someone purchases from your online store for $5 combines with a thousand other low-selling, inexpensive niche products to surpass the income that you make from selling top-of-the-chart music CDs or other mainstream products.

The neat thing about the Long Tail is that it seems to apply to so many phenomenon online, not just revenue. There’s a long tail of participation. A long tail of travel. There’s even a Long Tail blog, where all of this is discussed. I never thought the Long Tail could apply to my attempts to make money online.

But as I spoke with Sean, I realized that the revenue stream for online activities really is the Long Tail. You won’t make your fortune selling one product or service (even though some have). Instead, it’s the combination of various revenue streams, of selling a variety of products, that combines to create an income to equal your goals.

For example, you sell a premium and paid version of a podcast, and maybe 50 people sign up for the premium version. You sell ads in your sidebar, and maybe a dozen sign up. You create a forum and offer a tiered membership, and some more sign up. You sell T-shirts, mugs, and other paraphernalia, and some more sign up. You sell video tutorials and e-books and print books, and more sign up. You present at conferences and coordinate webinars, and more sign up. You offer one-on-one tutorials and online training, and more sign up. Any of these methods alone would produce income that is weak and unsustainable, but the combination of them all accrues a revenue stream that is substantial.

Now that I think about it, this is also the strategy Jason Van Orden recommends in a podcast with a hobby geneologist (though I didn’t realize it at the time).

The Long Tail may be the model underlying a number of phenomenon on the Internet. It may also be the best answer to the conundrum of making money online from a popular blog or podcast.

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O’Reilly’s definition is intriguing because it’s the opposite of the natural law of use. Your car doesn’t get better the more you use it. A music track doesn’t get better if more people listen to it. Your bank account doesn’t improve as more people use it. Your feet don’t get better the more you use them. Very few things actually get better the more you use them. Not Web 2.0. It’s almost paradoxical. The more people who use it, the better it gets.

O’Reilly gives two main examples:

• Google. With Google, every time a user makes a link to another site, Google uses that hyperlink to better inform its search algorithm.
• Amazon. Borders and Barnes & Noble have the same stock of books, but Amazon integrates user reviews and commentary to add more value to their literary collection. With each review, the site gets more valuable.

O’Reilly also mentioned eBay and Craigslist. With each system, the more people use it, the better it gets. O’Reilly also has interesting research on publishing and digital libraries, but I’ll save that for another post.

The question for technical writers is not how you can enable user-generated content with your help, but how you can make your documentation better as more people use it.

I wish I could say I have lots of cool ideas on how to do this. I don’t, maybe you do — refine search results based on user queries, allow users to comment on topics, sort topics based on popularity of views, enable users to contribute their own topics, configure search results based on topic viewing time, provide user community, yada yada yada.

These ideas aren’t new or particularly interesting. Partly it’s because they’re still so pie in the sky, how- -do-you-even-do-it type features. Next I’ll suggest telepathically downloading hotspots in user-brains to note the kinesthetic, verbal, or auditory preferences of your users based on the lobes that light up.

Yet we’re at a point technically where many of these features exist or are available. Our problem is that most help authors aren’t programmers, and few programmers get jazzed about coding help tools. When’s the last time you saw an open source help authoring tool that was specifically designed to create help systems?

(Okay, I did see one last week — called PHP Manual Creator, but it looked really primitive.)

In contrast, look at the explosion of social networks, blog platforms, video sharing tools, and countless other killer web 2.0 apps. Inevitably, help systems will also migrate more towards O’Reilly’s idea of Web 2.0. But rather than seeing these blow-your-mind-web-2.0-type tools emerge from the help developer community (i.e., all those companies who advertise in Intercom), I think the next-generation tools will come from web developers and designers who create them for another purpose. We’ll simply repurpose them to deliver help content.