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

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.

Looking for alternative careers in 1992, Davis hit on software development. He had an idea for the program that later became his livelihood. Called Zoot, the software helps researchers manage random bits of primarily text-based information, including notes and excerpts from articles. He taught himself to program in Visual Basic and got to work.

Davis saw programming as a way to escape the corporate life. He moved to a mountaintop house in Vermont and made his own hours. Ironically, Zoot became popular and he found himself working 12-hour days, seven days a week. "Zoot is pretty complicated, and as sole programmer, it was a lot of work," he says.

Later, as the Internet and Web became mainstream, Zoot became more useful for clipping and organizing Web pages, articles in Web-based newspapers and magazines, and e-mail. In addition to making Zoot more useful, the Internet helped make the business of selling Zoot easier.

When Davis started Zoot Software more than a decade ago, the online world consisted of a couple of hundred thousand people on services such as CompuServe. Advertising was expensive, and marketing consisted of lobbying reviewers in the PC magazines and hoping to get noticed. Now, Google AdSense makes advertising cheap and easy, and bloggers help spread the word about software. Zoot initially was distributed on diskettes through the mail. Now there are hundreds of software libraries on the Internet, and distribution services will, for a small fee, upload a developer's software to all of them.


These entrepreneurs have a lot in common. They have IT backgrounds. They were in the right place at the right time, with the right product or service. While Rose is single, the others have supportive spouses, a couple of them partners in the business. They all faced a moment of truth, when they had to screw up courage and stake their financial futures on their new businesses. They stay true to their own visions. And they're a little obsessed.

The Trotts' software became a career-driver

The Trotts' software became a career-driver
Timing is a critical factor. The Trotts launched their software just as post-9/11 politics were driving blogging into the mainstream. Soon after Digg launched, Paris Hilton's cell phone was stolen and its address book--filled with juicy celebrity contact info--was hacked. Digg posted links to the story, and Google and Yahoo gave the story prominent play.

When Zoot came out, Davis discussed the program on an online forum for users of Lotus Agenda, a similar program that was, even then, obsolete and no longer supported. Among the participants: James Fallows, a noted journalist whose work has appeared in Slate, The New York Times Magazine, and The New Yorker. Fallows fell in love with Zoot and wrote a glowing article in the Atlantic Monthly (paid subscription required). Zoot also got a favorable review from PC Magazine reviewer Bill Machrone. For Davis, Zoot is a lifestyle business. He's married, and his wife brings in income as a loan officer.

The Trotts run Six Apart together. They're former high school sweethearts. The company takes its name from the difference in their ages, in days. The Trotts stopped looking for jobs in July 2002, when they realized they were spending full-time hours updating and supporting the software and were making enough money to break even and cover rent and food. The turning point came when they received funding from Neoteny, a Japanese venture capital firm, in April 2003. The same month, they hired their first employee. The company grew to five employees by that July.

Schachter wasn't too concerned when he quit his job to devote himself full time to He had no financial responsibilities. "My co-workers were very supportive. I didn't think I'd have a lot of trouble finding another job in the financial industry if I had to. So it didn't seem the price of failure was particularly high," he says.

Accidental entrepreneurs often don't pay attention to the business side of things--for a while, at least. They focus on their creative visions. "When we started Movable Type, we didn't have a business model, and we didn't have a plan," Mena Trott says. "It was all about the product, and we were really motivated about creating a good product. With that, a good business followed."

To succeed, accidental entrepreneurs need a bit of obsessiveness: "It doesn't ever go away," Heather Armstrong says. "Some people can walk away from their jobs, but my job follows me into bed at night." (That's literally true--she occasionally blogs about things that happen in bed at night before going to sleep or in the morning while waking up.)

Says Schachter, "Anything worth doing is worth obsessing over."

Not everyone can be an accidental entrepreneur. It requires skill, dedication, vision, courage--and a little luck. But for a fortunate few, accidental entrepreneurship has changed their lives.

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