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It has taken eight years of his life, practically every cent he ever saved and more sleepless nights than he cares to remember.

But the struggle has made Chicagoan Michael Friedman into something of a David against the Goliaths of the modern record industry, his pint-sized Premonition record label more than once vanquishing giant competitors on the Billboard jazz charts.

More important, with an artist roster that includes vocalist-pianist Patricia Barber, tenor saxophone giant Von Freeman, drummer-for-all-occasions Paul Wertico and visionary singer-songwriter Terry Callier, Premonition clearly has come to represent some of the more dynamic facets of Chicago jazz. Not quite avant-garde but not conservative or retro either, Premonition somehow has managed to bring forth new ideas in music without alienating the middle-of-the-road, everyday record buyers who are essential for any record to win a berth on the jazz charts.

One-man operation for 5 years

Considering that Friedman was the label’s sole employee for its first five years (it now has three), starting in 1993, that’s no small feat. But the journey has not been easy.

“It’s a killer,” says Friedman, a former jazz drummer who found his calling on the other side of the microphones. “Interestingly enough, I got out of being a musician because of the unpredictability of it, and the fact that it was so hard to have a real life as a musician.

“And then I jump into the record business, and I find it’s pretty much the same thing, only more intense.”

But consider the rewards, both for Friedman and for music lovers. Classic Barber recordings such as “Modern Cool” (1998) and “Nightclub” (2000) not only established the Chicago artist as a major attraction around the world but won for Premonition a coveted distribution and licensing deal with Blue Note Records, which stamps its logo on Barber’s Premotion recordings and places the discs in record stores around the world. This alone gives Premonition a leg up on other indie labels across the country, which perennially face distribution woes.

Label wins high visibility

Moreover, discs such as Freeman’s freewheeling “Live at the Dakota” (2000) and Wertico’s breakthrough “Don’t Be Scared Anymore” (2000) have earned lavish critical praise, giving Premonition a level of visibility not often accorded boutique labels of its size. Billboard gushed that Wertico was “a cross between Jimi Hendrix and Ornette Coleman,” Down Beat termed Freeman “one of the greatest tenor players in modern jazz” and the New York Times swooned over singer Laurel Masse, whose work also appears on Premonition, citing her “marvelous sense of style” and her “purity of tone.”

“You might not believe it, but just by having an album on Premonition we got coverage from Billboard magazine, as well as all the major jazz magazines, the drum magazines, everything, really,” says Wertico, who has been recording for roughly two decades but achieved his greatest artistic and commercial success with his Premonition CD.

“That’s pretty remarkable, because if anybody wants to know about the record business, they should watch the Animal Planet channel — it’s all about a fight for survival.”

No particular plan

So how did Friedman transform the dream of owning a jazz record label into reality?

“I just took a leap,” says Friedman, who says he doesn’t make much more money than when he was gigging as a drummer, first in Chicago in the late 1970s and early ’80s, then in New York from 1983 to ’88.

“I had no grand plan, no business plan. I always loved trying to turn people on to the music, and when I started Premonition, in 1993, jazz record sales were at their height, with Wynton Marsalis as the icon,” adds Friedman, who was born in Chicago and graduated from New Trier High School and then the University of Illinois, as a percussion major.

“Wynton was great for record sales, so I thought, Why not?”

But Friedman took one more crucial step, releasing as his first Premonition disc a stunning recording by Chicago bassist Larry Gray, who was well known as a superior sideman. His work as composer, arranger and bandleader on “Solo + Quartet” surprised listeners everywhere.

It was Barber who put Premonition on the map, with Friedman to date having released four of her titles, each since “Modern Cool” advancing both Barber’s career and Premonition’s profile. Thanks to the success of “Modern Cool,” the one-man operation quadrupled its staff, which in these slowing economic times has been cut back to three.

Even so, with a catalog of more than a dozen discs and an additional six to be released before this year ends, Premonition clearly is gaining momentum. And though its roster is stylistically too wide-ranging to allow anyone to pigeonhole the label’s music, a certain sensibility defines everything the label does, says Friedman.

“If I had to describe what Premonition is all about,” says Friedman, “I’d say it’s not art for art’s sake, but it’s not commercial either. It’s really somewhere in the middle.

“What’s exciting to me about jazz is that the musicians are creative and there’s a definite artistic imperative, but there’s also a sense that the music arises out of a community and speaks to a community.

“In other words, I’m always searching for artists who are trying to reach out to listeners, to make a connection to them. That’s what people like [Thelonious] Monk and [Duke] Ellington always did, and they’re two of the role models.”

So are Blue Note Records president Bruce Lundvall, “for all the creative work he records,” says Friedman, and Chicago’s Bob Koester, whose long-running Delmark Records label Friedman considers “maybe the biggest and most important indie label in the country. Bob Koester has given his blood to that company, and now he has something to show for it.”

Give Chicago credit

Koester, for his part, marvels at how much Friedman has achieved in so little time.

“I’m always amazed at what he puts out with just one or two employees — frankly, I don’t understand how he does it,” says Koester.

“I think he picks his shots, and he picks them well, as opposed to me, who just puts out anything I like,” says Koester.Both Koester and Friedman, however, realize that the degree of success each has achieved probably could not have been duplicated in any other American city.

“Chicago is unique, a big metropolitan area with a tradition in the arts with a real community of people who will stand outside a club in freezing weather to hear music,” says Friedman, who also gives credit to the city’s enormous jazz infrastructure.

“There aren’t too many clubs like [Chicago’s] Green Mill or Jazz Showcase or Empty Bottle around the country, there’s only one Jazz Record Mart, and the kinds of artists who live here speaks for itself,” says Friedman.

“And yet you don’t have to a pay a fortune in rent, as you would in New York. So I’ll probably stay here for the rest of my life. But I would point out to anyone who wants to get in this business that it’s not for the faint of heart.”