Accidental Tech Entrepreneurs Turn Their Hobbies Into Livelihoods

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 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.

The Armstrongs use software called Movable Type (more on that later) to run their blog and Apple iBooks and a G5 tower to compose and manage it. Heather takes pictures with a Nikon D70 camera, improves them with Adobe Photoshop, and posts them to the Flickr photo-sharing service. She uses a simple File Transfer Protocol program to move files around. Their hosting provider is Liquid Web; they pay $200 per month for the server access and bandwidth. As for the content, Armstrong blogs in loving, exasperated tones about the joys and frustrations of being a stay-at-home mom and tells stories about her extended family (including her mother, whom she refers to as the Avon World Sales Leader). Leta is the star of the blog, with their dog, Chuck, a popular supporting player. The blog is a cheerful chronicle of 21st century digital domesticity, peppered with good-natured profanity, toilet humor, and sentimental stories. From Unemployed To Company President Mena Trott is the 28-year-old president of a hot technology company. Trott and husband Ben run Six Apart, which distributes Movable Type blogging software and the LiveJournal, TypePad, and new Vox blogging services.

Risk paid off for Rose (right, with Digg CEO Jay Adelson)

The Trotts started writing Movable Type as software for Mena's blog, Dollarshort, in early April 2001. It was a hobby. Then they were laid off from their jobs at a small Web design firm, where she was a designer and he was an engineer, in September 2001--amid the dot-com bust and just a few days before 9/11. They released Movable Type a month later. Movable Type is one of the dominant software platforms for managing personal and professional blogs. The software lets authors create a blog easily, using templates or by creating a fresh design from the blank page. Authors write posts either in a form in their Web browser or offline, then Movable Type handles the rest--publishing the posts to the Web, collating old posts into archives, managing user comments, and handling subscriptions by e-mail or RSS feed. Movable Type was light-years ahead of competitors when it came out. Other blogging tools predated it, but none had its power and flexibility. Competitors have emerged since--open source WordPress, most notably--but Movable Type remains competitive in functionality. Because it's written in a scripting language, Movable Type can be customized by users with programming skills. An API set allows for extensions. You don't need programming chops to use Movable Type or even need to know any HTML. Anybody who can write an e-mail or compose in Microsoft Word can publish and update a Movable Type blog. The software was initially donationware--users lent what they thought was appropriate. In late 2001, Six Apart introduced a commercial license for $150. Now the company has 135 employees. It's Delightful! It's Del.icio.us! Like the Armstrongs and the Trotts, Joshua Schachter saw his hobby become a business as demand for it took off. Schachter created the del.icio.us service while working in IT for several financial companies; his previous employers included Montgomery Securities, Bank of America, and Morgan Stanley.

Del.icio.us is free technology for saving and sharing bookmarks that are viewable to the general public. Each user has a page of bookmarks on the site. Instead of saving the bookmarks in folders, users describe each bookmark with keywords, or tags. Unlike a folder organization system, each bookmark can have multiple tags. A user who finds an interesting page about Linux alternatives to Microsoft Exchange might tag it "linux," "microsoft," and "exchange." Users subscribe to individual tags and see bookmarks from others who have that tag. (Try it out on the links in this paragraph.) Del.icio.us grew out of the popular late-'90s blog Memepool, which Schachter authored. That was back when blogs were hand-coded, almost exclusively run by techies, and consisted mainly of daily links and descriptions of interesting Web sites the authors had discovered during the day's recreational surfing. Memepool--named for the word meme, meaning idea, and a play on the phrase gene pool--takes suggested links from users. When Schachter got behind in posting to the blog, he copied links into a file. After a year or two, the file had grown to 20,000 links--out of control. In 2001, he wrote a single-user tool to track the suggestions; he called the tool Muxway, a nonsense word. He did that work on the side, while continuing to work in finance. Muxway became the multiuser del.icio.us service. He quit his job in March 2005 to devote himself to del.icio.us full time and received an undisclosed amount of venture and angel funding later that month. The service had 300,000 users and eight employees when it was acquired by Yahoo in December for an undisclosed purchase price. Schachter now works for Yahoo as director of engineering. Media Mogul Where the Armstrongs, Trotts, and Schachter became entrepreneurs as opportunity arose, Kevin Rose, co-founder and CTO of online news site Digg.com, sought out his new Web-based career.

(click image for larger view)Favorite links are a del.icio.us treat

Rose's background is in both IT and broadcasting. He worked in networking and systems administration in Nevada, then did online marketing and systems administration for IBM. At the time he created Digg, Rose was hosting a technology program on TechTV, now known as G4tv.com. Digg mixes the principles of Slashdot and del.icio.us. Users register to join it, and when they see an interesting technology article anywhere on the Web, they submit the URL, along with a headline and description. Submitted articles appear in a queue, which any registered user can review. If users see articles they like, they click an icon marked "Digg This." Articles receiving the most Diggs, or votes, appear on the home page. "I was sitting around thinking about how this would play out," Rose says. "My background in school is in computer science. I wrote a scoping document to a friend, who is a developer. The friend said it would take two or three weeks to create and cost 700 bucks, so I said, 'Let's go for it.'" That was in October 2004. Digg launched in December. When Comcast bought TechTV and dropped its technology focus, Rose quit. As is true for all the entrepreneurs we profile, he found that the Internet made it possible to start a business with little investment--much, much less than was needed before the Net became mainstream. Rose launched Digg on a $99-per-month server and built it on open source software--the basic Lamp architecture: Linux, Apache, MySQL, and PHP. He put up $700 for development costs, plus $99 per month for Web hosting. "It was something I was willing to take the risk on," he says. "I was planning for success. I decided to go for a dedicated server off the bat." Digg now has 16 full-time employees. The developer who wrote the initial code for Digg is lead developer at the company. Digg secured $2.8 million in funding in October from sources including Greylock Partners with Omidyar Network, plus angel investors including Netscape co-founder Marc Andreessen. Digg is privately held and won't disclose revenue. It generates sales from Google ads and recently entered into a partnership with Federated Media for ad sales. The Lone Developer Tom Davis had a career problem. He'd majored in marketing and advertising in college and worked at an ad agency his senior year. "I really didn't like advertising, and I kind of freaked out," he says.

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. CommonBond 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

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 del.icio.us. 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.