Going up against the Internet giants, the Hieggelkes of Chicago's Newcity are building a gateway to alternative media on the web.

After months of crisscrossing the country to court collaborators, Brian J. Hieggelke, AB'83, MBA'84, launched in June what he hopes will become a very loud voice for the alternative media on the World Wide Web.

Through his NewcityNet, Hieggelke, the president of Chicago-based New City Communications, aims to give "young urban adults with a disposition toward iconoclastic, independent, and creative ideas" a single point of entry to Web sites designed with them in mind.

The concept is known, in Web lingo, as a "portal." Microsoft, Excite, and Yahoo! run some of the largest portals on the Web. Their pages provide an entry point to Web sites on a multitude of topics, from autos to health to sports. By contrast, the smaller portals-such as Femina, which links to sites on women's issues-typically focus on one topic. In this quickly consolidating virtual world, Hieggelke is building a gateway to sites that serve a purpose on the Web akin to that, in print, of free city weeklies, known for their hip, edgy take on news and entertainment.

Hieggelke's foray into electronic media-and onto the national media stage-follows the 12th anniversary of his company's own flagship free weekly, Newcity, a Chicago tabloid that has the U of C written all over it. In February 1986, Hieggelke, along with his wife, Jan Muzzarelli Hieggelke, AB'85, and his brother, Brent J. Hieggelke, AB'88, published the first issue as a biweekly neighborhood newspaper, with former Maroon chief Frank M. Luby, AB'85, serving as editor. Earlier this year, the Hieggelkes celebrated the paper's first 12 years with a 16-page expansion and a complete redesign.

While Newcity has won nine Chicago journalism awards, New City Communications has earned a national reputation for its entrepreneurship. In 1993, it helped form the Alternative Weekly Network, which gives its 100 member papers the circulation and clout to attract national advertisers like Levi Strauss. The network's sales have grown from a few hundred thousand dollars to a projected $20 million in 1998. New City's national sales division, which specializes in network deals, is expected to account for nearly $5 million of the network's total sales this year.

"Five years ago, national advertising didn't exist in this business," says Richard Karpel, the executive director of the Washington-based Association of Alternative Newsweeklies, an industry group representing 114 city papers. "The network has had triple-digit increases each year. Brian and his people have been the biggest sellers of those ads."

Industry eyes are now watching Hieggelke's efforts on the Web. "It's a bold move and it's hard to tell what will work," says Karpel. "A big part of what alternative weeklies do is tell people how to spend their leisure time, and a lot of companies are betting that people will go to the Web for this information. We want to be positioned to meet this challenge, and what Brian is doing could put us there."

Over the last nine months, Hieggelke has visited potential Web affiliates in more than 40 cities, logging 4,639 miles on the road and 24,359 miles in the air. He's targeting city papers in the 100 largest markets and Web sites that cater to the same audience. So far, he has signed 17 city weeklies-including St. Louis's Riverfront Times, New Orleans' Gambit Weekly, and Portland, Oregon's Willamette Week-to provide links to their Web sites from NewcityNet's home page, found at the address http://www.newcitynet.com. In return, NewcityNet gives the affiliates technical support and national advertising sales.

The idea, Hieggelke says, is to do for alternative Web sites what CBS did for independent radio stations. "CBS had a business model where it developed the national strategy, while each station was left to develop its own local strategy," he explains. "The financial awards were distributed across the spectrum. We want to similarly build a brand name with equity on the national level that the local affiliates can benefit from."

Hieggelke has been racing to establish a Web presence for Newcity and other city weeklies before some big names with deep pockets move too far into the weeklies' arts-and-entertainment domain. Already, Microsoft has been busy constructing Sidewalk, a smaller portal on its general network home page with links to city entertainment guides created, owned, and operated by Microsoft. America Online and Yahoo! also run portals to localized entertainment listings. The corporate draw? Ad dollars and an audience. Karpel estimates that alternative papers last year earned $400 million-mostly in ad sales- and were picked up by some 20 million people each week.

Despite the competition from the Internet giants, Hieggelke maintains that NewcityNet meets a need. "If the Web is going to consolidate into portals, then there should be a place that speaks to our audience," he says. "Unlike everyone else, we are encouraging local control and targeting a specific demographic niche as opposed to grabbing mainstream, mass-market share."

Hieggelke's charge into alternative media contrasts with where he and Jan seemed headed during their College days. The Joliet, Illinois, natives met in a high-school English class, married in 1980, and had their first of three children as second-years. Jan completed her economics degree after taking a year off, while Hieggelke-a varsity football player, Phi Gamma Delta brother, and economics concentrator who entered the GSB as a fourth-year-took a job buying and selling securities for Goldman Sachs.

In the fall of 1985, Hieggelke, a self-described "media junkie," caught the "entrepreneurial bug" and convinced Jan to help him start a paper for their Printer's Row neighborhood (where they still live in a Dearborn Street loft). His brother Brent, a second-year at the time, came on board as the paper's main ad salesman, taking the Jeffrey Express downtown every afternoon to put in 60-hour work weeks on top of his studies. Hieggelke persuaded Luby, who edited the first 10 issues and is now a marketing consultant in Bonn, Germany, to join over Edwardo's pizza.

"The U of C is mostly responsible for what I'm doing now," says Hieggelke. "When I went to the U of C, I was a classic suburban kid who did very well in high school without lifting a finger. My creative side got unlocked and I learned to write at the U of C, where a show of Kandinsky watercolors sparked my interest in art and Joe Williams beat the hell out of my writing and, thank god, gave me confidence." Early on, Hieggelke squeezed in 6 a.m. editorial meetings before the market opened, later also writing a media column. In the fall of 1988, he decided to leave Goldman to work full time for the fledgling media company. From the beginning, he has served as the "big-picture" man, while Jan, as company vice president and copublisher of Newcity, has acted as the "nuts-and-bolts," day-to-day business manager, devising practical plans to implement Hieggelke's grand visions. When he wanted to mark the paper's 10th anniversary with events in 10 different venues on the same night, for example, she arranged 10 events over the course of the year. "Brian's tendency to think big sometimes risks getting too far away from where the business is in terms of staff and resources in the present," she says. Jan also recalls the craziness of the paper's startup-carting a computer back and forth from home to a nearby office, shuttling stacks of the paper around town, all while they were raising a young family: "Considering what we went through in the early years, I get great satisfaction from what we have accomplished so far."

In 1990, the Hieggelkes decided the paper would be more competitive for ad dollars and more effective editorially if it came out weekly and covered the whole city. "Our articles had already angered all the neighbors," laughs Hieggelke. But as a weekly, they found themselves going directly up against the venerable Reader, Chicago's reigning free weekly. "We tackled a gorilla," says Brent, who rejoined the family business after a two-year hiatus working for investment bank Morgan Stanley. His one-year plan to help with the expansion turned into seven, along the way enlisting some circulation and invoicing help from wife Kimberly Sutton Hieggelke, AB'88.

"It was a longer project than any of us thought," says Brent, who is now marketing director of ABC Technologies, a Portland, Oregon-based software firm. "We underestimated the competitive environment. I couldn't walk away and not feel guilty until it was making money."

Today, Newcity has carved out its niche, notes Karpel, as the alternative paper geared to Chicago's younger (20- and 30-something) hipsters. Hieggelke wears his hair a good 2 inches longer than in his U of C days, and the North Halsted office in River West that he shares with Jan (her desk 6 feet from his) boasts exposed brick rather than wood paneling. They plan to keep their multimillion-dollar company independent for the foreseeable future-and to keep the bold moves coming.

Take the recent redesign, which generated more letters to the editor than any other issue. Disgruntled readers thought the new look-which features funky sideways columns and bumping text separated by hairline rules-went over the top. The noise prompted an article in the summer issue of Design, published by the Society for News Design, which asked if the changes spelled "great design or just a pain in the neck" and reprinted 24 of the letters, including a note from the mother of one of the paper's cartoonists who proclaimed the redesign "horrific."

Hieggelke takes such flak in stride, considering it a sign that Newcity is pushing the right buttons. And, like a true U of C grad, he can cite an appropriate source: Joseph Schumpeter's theory of "creative destruction." He explains: "The vision for the paper is expressed in its first word, 'new.' Without destroying something, you can't make it better." With a new look for the paper, a new way to sell ads, and a new portal on the Web, Hieggelke still believes that going out on a limb is what makes work "fun and exciting."