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Chicago entrepreneur Josh Schneider has a lot on his mind.

He’s running 25 minutes late for his 9 a.m. appointment. He’s forgotten to bring a check to cover payroll at his software start-up, Epigraph Entertainment. He’s not ready for his meeting with Epigraph’s advisers. And he’s due for an early lunch in 90 minutes at the Standard Club with the silver-haired CEO of another of his ventures, ePrairie.com.

A boyish figure in a navy-blue Zegna suit, he’s walking fast, head down, earphones on, immersed in the heavy-metal sounds of Black Sabbath.

He looks, as he often does, serenely happy.

And why not?

The 27-year-old is known in Chicago tech circles as a wunderkind.

Six years ago when Schneider was a senior at the University of Illinois, he and partner Michael Hakimi founded one of the area’s first Internet service providers, American Information Systems. They sold it to Exodus Communications in early 1999 for $20 million in cash, plus stock options.

Schneider quit Exodus soon after, forfeiting his options, to do what he likes best–start another company. He wound up a player in several.

The Internet scene was bubbling with promise and venture cash when he teamed with computer whiz Keith Amonlirdviman, now a 21-year-old Stanford University grad student, to develop Web sites for the likes of guitar freaks and aviation buffs.

Choosing a red star for Epigraph’s logo in a tongue-in-cheek nod to a Communist ethos, they envisioned visitors to these sites forming vibrant online villages, building their own content by contributing Web pages and interacting online–Internet communities in the truest sense.

But their success was limited. Flight.com never took off, nor did SilverPlate.com, a digital photo site. Two others proved more promising. Guitar.com, with upward of 1 million unique users per month, reportedly is merging with Los Angeles-based Musician.com (Schneider wouldn’t comment on the deal). And ePrairie.com, a media site aimed at Chicago’s high-tech community, is expected to announce its first round of venture financing this week.

Schneider enjoys the start-up scene as much as he loves guitars, computers (he has five linked in a high-speed network in his city apartment), ramen noodles and Las Vegas blackjack tables.

His business instincts come naturally. His great-grandfather was a grocer on Chicago’s West Side; his maternal grandfather, a downtown car dealer.

Networking is his most important talent. He has a gift for attracting older business people as advisers, customers and colleagues, even as he surrounds himself with brainy twentysomethings.

He knew to listen early this year when one of Epigraph’s advisers, e-commerce guru Mohanbir Sawhney, counseled that Epigraph’s commercial potential lies not in its Web sites, but in the proprietary software that makes the sites work.

So Schneider traded his blue jeans and T-shirts for those Zegna suits, and his grilled-cheese sandwich lunches for Standard Club fare, to build Epigraph into a major software company.

He’s been hiring managers and talking to potential investors with an eye to launching a commercial software product formally late this year.

He’s also re-reading an author he’s revisited periodically since his high school days at Glenbrook North.

“Have you read John Kenneth Galbraith’s `The Great Crash’?” he asks ePrairie’s CEO over lunch. “Or `A Short History of Financial Euphoria’?”

He ventures an opinion that the tech stock market won’t improve any time soon.

“I’m personally preparing for two more years of this,” Schneider says matter-of-factly.

The CEO stares at him.

“Sorry to be so grim,” he apologizes, ducking his head toward his soup and flashing a grin.

Schneider has a lot on his mind.

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