(FORTUNE Magazine) – LA CRESCENTA, CA. Founded 1995 Revenues: N.A. Employees: 110 Private www.citysearch.com

Bill Gross started out looking for a haircut. He ended up founding a company. That's just the kind of guy Bill Gross is.

The 37-year-old serial entrepreneur is the technological wiz who once headed up a team at Lotus Development and went on to create edutainment software house Knowledge Adventure. Now he has invented CitySearch, a company born when Gross, in New York City for a wedding, decided he needed a haircut.

"I looked in the Yellow Pages," he says. "There were pages and pages of barbers, and I didn't know where they were or how good they were. So I just chose one and got in a cab. When the cab pulled up, I knew immediately it wasn't the kind of place I wanted, but by then it was too late."

Most people would have waited a few weeks for the lousy haircut to grow out and forgotten the whole episode. Not Gross. He decided that if he'd had photos of the barber shops, he could have made a more informed decision. From that follicle of an idea came CitySearch, which will offer troves of urban info--where to eat, where to play, even where to vote--via the Internet. For each city it covers, the service will supply photos and information on thousands of businesses as well as postings on volunteer opportunities and community events. CitySearch today covers only Chapel Hill, North Carolina. Pasadena and, yes, New York City are next. It expects to add some 30 cities by the end of next year.

Never one to wait around, the peripatetic Gross has headed off to found other businesses: He left CitySearch in the hands of Charles Conn, 34, a former partner at McKinsey & Co. While burgs like New York and San Francisco already have rudimentary Internet directories, Conn hopes CitySearch will set the standard for comprehensiveness and ease of use. "We have to overcome the mom factor," he says--the fact that right now most sites require so much computer expertise that your mom would rather make do without them.

CitySearch is easier than that. Say you want to eat at an Italian place in the neighborhood. You log on, type in your address and the words "Italian" and "restaurants," and select a five-mile radius. Up pops a list of dining options. (A similar list would pop up if you substituted "eateries" or "food." Conn hired a lexicographer to build a database of 25,000 words commonly used to find goods and services--that saves Mom the hassle of having to try dozens of keywords in hopes of finding a good match.) You can peruse menus, compare decor, and even view a map showing how to get to the place you pick. You can personalize CitySearch, so that every time you log on, it will present you with a list of activities that might appeal to you.

For users, CitySearch is free. The company plans to make money the yellow pages way: Each business gets a listing at no charge and pays less than $100 a month to post information. The free listing will keep CitySearch comprehensive and help drum up business. On the Chapel Hill site alone, users can compare 25 nightclubs, 23 pizza joints, and, pace Bill Gross, 15 barbershops.

--Tim Carvell