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Mitch Wagner
Mitch Wagner
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Accidental Tech Entrepreneurs Turn Their Hobbies Into Livelihoods

InformationWeek interviewed five accidental entrepreneurs, including the founders of and Digg and the author of the blog Dooce, to find out how they freed themselves from the paycheck-to-paycheck grind.

Most people who pull down a paycheck dream of making a living at their hobby. For IT managers, the dream is more within reach than it is for most professionals, as their technical skills can give them a head start in building businesses on the Web. A supertalented few have even made fortunes.

How do they do it? We went straight to the sources, interviewing tech pros who turned their cyberhobbies into full-time jobs. Many of them truly were accidental entrepreneurs; others at least had an inkling they could make a go of it. All were helped along by a business-fertile Internet environment, their raw ambition, supportive spouses, and a little luck. They haven't all become rich, but they're all making a living at what they used to do for fun.

The Blogging Mom

Heather Armstrong, 30, is one of the accidentals. Her blog, Dooce, is the chronicle of the roller coaster that is the last five years of her life. Armstrong was single when she started it in 2001, working as a Web designer and writing disparagingly about her overpaid, spoiled employers at a Los Angeles software developer and her life partying and hanging out with her friends. "I worked for drug-addicted executives and discovered what life was like as a recovering Mormon," she writes on the About This Site page of Dooce. "This means that life was filled with PowerPoint templates and lethal amounts of tequila." The blog takes its name from a typo she often made while instant-messaging friends and co-workers; instead of typing "dude," she'd write "dooce."

Getting fired can lead to good things, the Armstrongs found out

Getting fired can lead to good things, the Armstrongs found out

Photo by Lance Clayton
She got fired in 2002 when her employers discovered her blog--and the disparaging things she wrote about them. Being fired for blogging was her first exposure to online fame. Word got out, and the name of her blog became Internet slang--to be "dooced" is to be fired for blogging about work.

After getting her walking papers, Armstrong continued blogging, and the popularity of the site grew. Her life changed, too: She married; moved to Salt Lake City with her husband, Jon; and had a daughter, Leta, now 2. The Armstrongs started thinking about running ads on the site about a year ago but were reluctant to go commercial. "There wasn't a tried-and-true method of advertising working on a blog. I was worried about backlash," Heather says.

Last October, two companies--BlogAds and Pheedo--approached the couple about advertising. "They paid enough that my husband was going to be able to leave his frustrating and soul-sucking job," Heather says.

Jon helps his wife run Dooce. For the first two years, she hand-coded Dooce, but he convinced her to automate the process with blog-publishing software. He set up the business and arranged lawyers to incorporate. These days, Dooce gets its ads from two sources: Federated Media for the Web site, and Pheedo for ads in the site's RSS feed. The two networks supply sales help and serving technology, and set ad rates.

A few short years ago, starting a Web business required a huge investment. Now the tools are cheap or free, essential to keeping the family biz in the black. Heather worked for a Los Angeles company that was founded by the crown prince of Dubai--this wasn't the place she was fired from, but another job. "They spent millions of dollars developing their own content management system, and in the two years that I was there, they didn't get a tenth of the traffic of what my site is doing." Dooce gets 45,000 to 65,000 unique visitors on weekdays, about half that on weekend days.

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