Earlier this month, Randall Munroe, creator of the hugely popular web comic xkcd, announced on his blog that he would be publishing a book collection of the strip. Given the number of six-figure book deals that major book publishers have thrust upon popular bloggers, there’s little doubt that Munroe’s millions of monthly readers could have easily garnered him a similar signing. But he chose to publish his book through BreadPig, a company set up by Reddit founder Alexis Ohanian. The book is available in xkcd’s store, where the artist has been selling T-shirts and other merchandise for years. Munroe wrote that the work might “possibly” appear in bookstores.

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The fact that Munroe considers traditional brick-and-mortar book stores to be an afterthought sheds light on the entrepreneurial nature of online web comics creators. (Munroe did not respond to an interview request for this article). According to a list compiled on Wikipedia, there are at least 40 self-sufficient web comics that are “known to produce the primary income of their artists and/or writers.”

Back in June, political cartoonist Daryl Cagle published a blog post about the annual Association of American Editorial Cartoonists (AAEC) convention.

“In recent years, the convention has had the flavor of a wake, as cartoonists mourn the loss of full-time newspaper positions,” he wrote. “Many newspapers used to cover the cost of their employee/cartoonists attending the long, four-day AAEC convention and now cartoonists have to find a way to cover the cost on their own.”

Cagle noted that many newspapers are shedding their full-time cartoonists, forcing many of these artists to become freelancers. With the industry in decline, what can newspaper cartoonists learn from these entrepreneurial web cartoonists? How are these self-sustaining artists making a living and why are they choosing to forgo traditional publishing outlets to deliver content to fans?

Comics for free, merchandise for sale

Richard Stevens created the web comic Diesel Sweeties in 2000. Depicting a world where humans and robots co-exist — often romantically — the individual strips are largely self-contained and have a number of recurring characters. The comic was picked up for newspaper syndication in early 2007, but in 2008 Stevens went back to the web-only version. He told me that today his site receives about 30,000 readers a day. Of those, he said, he really only needs to find about one or two percent of his fan base to support him financially.

“I know in mass media terms our numbers aren’t that big, but because we’re so close to the ground we have a closer relationship to [our audience],” he said. “So I think if you’re in my bracket up to Randall [Munroe’s] bracket [in terms of readership], I would say one or two percent are really going to support you.”

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Like others I interviewed for this piece, Stevens makes most his money through selling merchandise, most notably T-shirts. He operates his business out of his home, purchasing the shirts in bulk and selling them on his website. In that sense, the web comic is a kind of loss leader (though one person I spoke to disliked that term) for the print product. It gathers fans that can be turned into paying customers.

Surprisingly, however, many web comic artists don’t simply transfer their comics to the T-shirt. Though classic strips like The Far Side have done well in T-shirt form, several web artists create special, separate content for their merchandise.

“I might do a comic of eight panels of people digressing,” Stevens said. “It wouldn’t work on a shirt very well…Sometimes, if I get a lot of reader responses, I’ll try to transfer a line from the comic into a shirt, but mostly I make the T-shirts for myself. And gleaning evidence from the message boards, from Facebook, from having conversations 24/7 with my fans, I can get a sense of what will sell.”

From middle management to we cartoonist

Howard Tayler was making a six-figure salary as a middle marketing manager when he decided to quit his job to work on his web comic, Schlock Mercenary, full time. The move came when the comic was losing money, leaving him in a sink-or-swim situation.

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“So I quit the day job and then frantically and desperately over the period of the next 15 months applied everything I knew about business and marketing and the Internet, all that stuff, to finding a way to monetize what I had,” he told me. “And what I had was a captive audience.”

Tayler differs from many web cartoonists because he makes most of his money selling book collections of his comics. Since 2006 he’s released five books — with a sixth on the way — and he said that his family takes in about $30,000 per book. He orders print runs of about 5,000 titles; he says that at this print run he can get them for almost the same price as a major New York publisher, ensuring a high profit margin even if he sells them wholesale. His wife helps with the business side, taking care of invoices and shipping.

Though most of his money comes from books, he also has gone the more traditional merchandising route by selling T-shirts, buttons, and even digital-only PDFs of his work. (Sometimes he uses these products to help raise money for charitable causes). He also sells special edition books that include original sketches, an idea that turned out to be a particularly profitable moment of inspiration. But would he forgo all this for a traditional publisher if one came along?

“If I had the opportunity to sell my books to a large publisher, I’d probably jump on it,” he said. “The way we’re doing it, the business is kind of taking over the whole house. My wife is the production manager, she’s our chief of operations; when we ship out books for a pre-order, she spends a month collating receipts, invoices, sorting postage. We printed $40,000 worth of postage this year, and all that’s a lot of work. I’d much rather just be a cartoonist, and if that opportunity presented itself, if a publisher came to me and said, ‘Hey we’ll sell your books, and we’ll sell 250,000 of them,’ then I’m still making a living so I won’t complain.”

I asked Tayler about newspaper woes and whether his breed of content monetization would be a viable model for comic strip artists. He said that before he quit his day job he studied “disruptive technologies,” where profitable businesses meet new models that slowly chip away at their profit margins until suddenly they upend the entire model.

“You’ll see it’s happened with everything from sailing ships versus steam ships, automobile versus horse and buggy,” he said. “It happened five times with the disk drive alone, where new technologies have undercut the old technologies. I look at that pattern and I look at what’s happening now, and I know two things. One, newspapers and comics syndicates are definitely the old technology, the old business model. They were at their most profitable 15 years ago, and they’re dying. They’re going to be replaced by something.

“The other thing I know,” he continued, “is the thing that replaces them, whatever it is now, is not meeting the needs of the current newspaper customers. They’re going to look at what comes next and say this isn’t what I wanted, I long for the good old days. But 20 years from now, we’ll all be better off, and whatever comes along to replace newspapers will finally have been able to do whatever the newspapers do and then some. Whether that’s me, guys doing what I do, or someone who replaces me in the interim, I don’t know… Newspapers are dying, and the syndication model is dying, and something better is going to come along to replace it.”

Simon Owens is a social media consultant and associate editor for MediaShift. For more about him read his blog or contact him at simon.bloggasm@gmail.com