In 2006, Adam Klawonn cashed out his newspaper job vacation pay to reinvent himself as a digital journalist. He bought a laptop and a camcorder, and trained himself how to create a blog, edit HTML code, shoot video and edit it in Final Cut Pro, edit photos, create graphics in Photoshop, and manage a Web site—specifically, “The Zonie Report,” an online regional news magazine about Arizona (tag line: “The rest of the Arizona story”) that he started on his own dime without any big funders or major journalism connections.

Last week, Klawonn announced that after nearly four years, and “not a penny to show for it,” The Zonie Report would shut down. He had hustled to promote the site: attending mixers and industry trade shows, relentlessly marketing online through social networking sites, and speaking at media-related events. He even showed up at local charity road races with The Zonie Report logo prominently displayed on his chest alongside his runner’s bib, wearing a sombrero just to draw attention. He had also worked to create a steady stable of contributors. He got local journalism students involved, hired some regular bloggers, signed freelancers to contracts and paid them—out of his own pocket—the shockingly competitive rate of forty to fifty cents per word. He freelanced on the side to keep himself afloat.

In the end, he had a total of five inquiries from advertisers over nearly four years, and lost all but $500 of the $20,000 he sank into the endeavor. At the height of his site’s traffic, his audience was 8,000 monthly visitors out of the six million Arizona citizens that he considered potential readers. “In hindsight, I stuck with this longer than I should have,” Klawonn said. “I should have quit two years earlier.”

It’s no big secret that deep pockets and name recognition will help any startup company, or that spreading out your risk by finding investors is a good idea. The Internet, though, is supposed to level the playing field somewhat for aspiring publishers, with no major elbow-rubbing efforts, marquee name-endorsements, VC backing, or Ivy League degree required to find success. Many old-media refugees have taken this idea to heart and founded their own one-man startups, only to learn that success can be more elusive than they think—see here and here. Like them, Klawonn found that having money and connections count just as much online as they do in the real world.

In the words of Thomas Levenson, a professor of science writing at MIT:

[Klawonn] tried a local, focused, partly free-labor news source model and failed. […] It remains the underlying fact that he is one of a number of folks finding it difficult to produce an alternative to oligopolistic mass media on one side and boutique or labor-of-love narrowly focused sources on the other.

“On the Internet, there’s something for everyone and if you want to start up a publication about something very specific, like healthcare for children with multiple sclerosis, for example, you can do that. It may not pay the bills, but nothing is stopping you,” Klawonn said. “But if your goal is to be the Voice of San Diego or MinnPost it certainly doesn’t hurt to have old media or old money connections.”

Klawonn, now thirty-one, had neither. He worked at The Arizona Republic for three years right out of college before reporting for the San Diego Union Tribune for two years. He left to create The Zonie Report in 2006, after he felt like he wasn’t learning the new media skills he’d need to stay competitive in a changing industry. He conceived of the project as a sort of master’s course in journalism, investing the money he had saved to pay for a graduate degree. He figured he had nothing to lose even if The Zonie Report didn’t make it.

“I was either going to go broke making this site a success and least re-train myself and have fun doing it, or it would be a huge success and I would laugh someday about how it started in my home office,” he said. “Either way, I’d either be really successful or back in the workforce as a totally reinvented journalist.”

Alexandra Fenwick is an assistant editor at CJR.