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Found via the NYTimes

MARKUS FRIND, a 29-year-old Web entrepreneur, has not read the best seller “The 4-Hour Workweek†— in fact, he had not heard of it when asked last week — but his face could go on the book’s cover. He developed software for his online dating site, Plenty of Fish, that operates almost completely on autopilot, leaving Mr. Frind plenty of free time. On average, he puts in about a 10-hour workweek.

For anyone inclined to daydream about a Web business that would all but run itself, two other details may be of interest: Mr. Frind operates the business out of his apartment in Vancouver, British Columbia, and he says he has net profits of about $10 million a year. Given his site’s profitable advertising mix and independently verified traffic volume, the figure sounds about right.

There’s much to be admired in Mr. Frind’s entrepreneurial success. But his site, now almost five years old, has some unfinished patches and irritating quirks and seems to come from the Anti-Perfectionist School of Design.

Mr. Frind built the Plenty of Fish Web site in 2003 as nothing more than an exercise to help teach himself a new programming language, ASP.NET. The site first became popular among English-speaking Canadians. Popularity among online daters in many United States cities followed more recently, and with minimal spending on advertising the site. According to data from comScore Media Metrix for November 2007, Plenty of Fish had 1.4 million unique visitors in the United States. In December, Mr. Frind said, the site served up 1.2 billion page views, and page views have soared 20 percent since Dec. 26.
Spending time at Plenty of Fish is a visually painful experience. Wherever a row of members’ photos is displayed, which is most pages, many of the faces are elongated or scrunched because Mr. Frind has not taken the trouble to write the software code that would automatically resize frames or crop photos to prevent distortion. When I asked him why he had not addressed the problem, he said it was a “trivial†issue that did not bother users.

A blasé attitude is understandable, given that Plenty of Fish doubled the number of registered customers this past year, to 600,000, Mr. Frind said, despite the fact that each month it purges 30 percent of users for being inactive. Somehow, the site instantly replenishes the lost customers and attracts many more to boot.
No one heads to Plenty of Fish for the customer service, which is all but nonexistent. The company does not need a support structure to handle members’ subscription and billing issues because the service is entirely advertising-based. Its tagline is: “100 percent free. Put away your credit card.†For hand-holding, users must rely on fellow members, whose advice is found in online forums. The Dating & Love Advice category lists more than 320,000 posts, making up in sheer quantity what it lacks in a soothing live presence available by phone.

The principal customer service that Plenty of Fish provides is responses to complaints about possibly fraudulent identities and to subpoenas and search-warrant requests. Last year, Mr. Frind hired his first, and still only, employee to handle these requests, freeing him to attend to adding new servers when required and tweaking code. “Most of the time, I don’t need to do anything,†he said.

To keep his site’s forums free of spam, Mr. Frind has refined a formula for analyzing customer feedback and arriving at a determination of whether a given forum post is spam and should automatically be deleted. He has also devised some new software twists that enable him to offload work to his customers, letting users review the photos that are uploaded to the site.

Mr. Frind says that close to 50,000 new photos come in every day, each one of which needs to be checked to verify that it is an actual person and that it does not not contain nudity. The work would be costly if Mr. Frind relied on a paid staff to do it.
Fortunately for him, there seems to be an inexhaustible supply of humans eager to look at pictures of other humans, and Mr. Frind taps his customers to carry out the reviewing, gratis. Some have made it their principal pastime. Among Plenty of Fish’s volunteers were 120 who last year evaluated more than 100,000 images each. He explains his volunteers’ enthusiasm for the work as an expression of gratitude: “Lots of people feel like they want to give back to the site because it’s free.â€

Plenty of Fish displays banner ads, Google-supplied ads and, most profitable of all, “affiliate†marketing links that send users to other dating sites. For example, Mr. Frind said, when one of his customers clicks on an advertisement for a book titled “Double Your Dating†and, after being sent to the publisher’s Web site, ends up buying it for $40, the publisher pays Plenty of Fish a commission — of $40 — for the sale, glad to have landed a customer that past experience shows is a good prospect for “upselling†other goods and services related to dating.

For all that Mr. Frind has accomplished, his site looks puny when compared with Craigslist, which has built a mighty automation engine tended by only a handful of people. Craigslist’s personals draw about six million unique visitors a month, more than any other dating site, and its listings for all categories generate 10 billion page views a month. It covers 450 localities in 50 countries around the world — with only 25 employees. It is among the top 10 busiest English-language sites, but the customers who enjoy its free listings, like Plenty of Fish’s, must serve themselves or seek assistance from others. “Anything that represents customer hand-holding represents a failure of site design,†said Jim Buckmaster, Craigslist’s chief executive. “We try to make changes to the site to make the problem go away.â€

BOTH Plenty of Fish and Craigslist have created sites that run almost completely on their own, but in different ways. Craigslist has no commercial messages other than listings, and it collects fees only for a minuscule slice of its posts. It charges employers for jobs listings in 10 of its 450 cities, and brokers for apartment listings in New York City. All other listings are free. “To most of our users,†Mr. Buckmaster said, “it’s a mystery how we make money.â€

At Plenty of Fish, there is no mystery: a large square of advertising sits in the middle of most profile pages. Its success demonstrates that many consumers will tolerate, and even embrace, advertising when a site offers a free service for which others charge membership fees.

Mr. Frind has found that rare business in which the profits gush in, whether or not he leaves his hammock.

Randall Stross is an author based in Silicon Valley and a professor of business at San Jose State University. E-mail: stross@nytimes.com.

http://www.nytimes.com/2008/01/13/business/13digi.html

:fastlane:
 
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