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Accidental Entrepreneurs


Posted by Mitch Wagner, Jul 5, 2006 08:09 PM

If you're at all dissatisfied with your job, this is a tough week for you. You've got a four-day weekend behind you, and the height of the long, hot summer ahead of you. Plenty of time to sit and daydream about telling the boss to take a hike and making money doing what you love.

Many of you have personal Web sites you work on in your spare time, either blogs or little e-businesses or software-as-a-service applications. Wouldn't it be great if you could just make a living on that stuff and leave the paycheck-to-paycheck grind behind?

The subjects of our article on accidental entrepreneurs did just that.


InformationWeek interviewed five people who run successful Internet-based businesses that started out as hobbies. These are people who started out holding day jobs or unemployed and saw their hobbies bring in enough money that they could support themselves. A couple of our subjects got rich off it.

We interviewed Kevin Rose, founder of the Digg online news site; Joshua Schachter, founder of the del.icio.us social bookmarking service; Mena Trott, co-founder of Six Apart, the blogging software and service company that produces Movable Type software; Tom Davis, who wrote information management software called Zoot; and Heather Armstrong, who writes the popular blog Dooce.

Our article describes for you the history of their projects and how they evolved from hobbies into paying businesses. It required hard work, ambition, supportive spouses, and a little luck.

By the way, when I say InformationWeek did the interviews, I mean me. Yes, back before I was the glamorous editor-type you see before you today, I was a reporter. I did interviews and wrote articles. I decided to dust off my reporter's notebook and fedora with the PRESS card in the band to see if I still had the chops. I'm pretty pleased with the results, if I do say so myself.

One particularly interesting theme running through all the interviews was how the Internet makes it cheap to start a business. Web hosting is cheap nowadays, and the software to publish and manage a Web site is cheap or free.

So when am I going to turn my hobby into a business? Well, last I checked, there wasn't much financial demand for people who lie on the couch watching Homicide: Life in the Streets DVDs while eating Jimmy Dean Sausage, Egg & Cheese Biscuit Sandwiches. But as soon as that market takes off, I'm going to be filthy rich.

What are the Diggs and del.icio.uses of tomorrow? What's the most interesting emerging business you see on the Internet today? Leave a message below and let us know.

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