Andrew "Flip" Filipowski (Tribune photo by Charles Osgood)

It was the winter of 1986 when Andrew "Flip" Filipowski finally made it to Harvard.

The school had rejected his application years earlier, but now Filipowski was the 35-year-old head of a hot Chicago software company.

All week at an executive-training program, he peppered the professors with witty remarks and novel takes on the school's famous case studies. Even the Harvard Business School elite had to concede that the Polish guy from Chicago had something on the ball.

But Filipowski wasn't finished. At the closing dinner, he popped up and told the b-school professors he could turn their lives around. It was simple: Buy out Harvard Business School. Professors would rule, and the administrators would work for them.

At the time, everyone laughed. But nobody's laughing at Filipowski's wild ideas today.

Now the college dropout with the ponytail, diamond-stud earring and flowered Hawaiian shirts is looking to turn Chicago into a high-tech haven.

At 49 years old, he still knows how to work a crowd. And his ability to make his grand plans sound like the next big thing has, for better or worse, installed him as the face of Chicago's fledgling dot-com community.

Whether that's a good thing is set to be tested in coming days as Filipowski offers stock to the public in his latest big vision.

It's called Divine Interventures Inc., a new-economy conglomerate that invests in Internet firms. And Chicago has seen nothing like it before.

But Filipowski's plan for a splashy public offering is loaded with peril. The market for these ventures has soured and one of his leading advisers has warned him to back off.

If his company flops, Filipowski will not flop alone. A glittering lineup of investors stands to suffer as well--from Michael Jordan to the heir to the Wrigley fortune.

Moreover, Chicago's effort to emerge as a high-tech center in the same league as San Francisco, Boston or New York would be undermined, perhaps for good. That would confirm the city's image as a backwater for the fastest-growing part of the economy.

It's all riding on a guy with an uneven track record, who was demoted at one company, kicked out of another and wooed into selling a third after promising he would keep it.

"Flip is a wonderful promoter, but I'm not sure he's a good investor," said Len Batterson, chief executive of a Chicago venture capital company. "There's a certain danger in that. If (Divine) doesn't make it, it's a high-profile failure" for technology in Chicago.

If the past is any indication, what happens to Divine won't change a thing about the man himself: Filipowski will remain a flamboyant collector of everything from multimillion-dollar homes to vintage comic books. He will continue to seek out extreme business risks, thinking nothing of putting on the line his own reputation and the livelihoods of his employees.

"You can back off and melt into the background," said Filipowski. "Or you can step forward, hang a bull's-eye on your chest and take the good with the bad."

At least Filipowski is no interloper. He grew up on Chicago's Near West Side, sweeping up at his father's grocery stores, though never well enough to satisfy his dad's standards. His parents, Polish immigrants, pushed him to achieve.

His father often recited a Polish expression, which Filipowski translated: "No matter how people want to sugarcoat it ... in their minds, they will absolutely be thinking that if you're poor, you're stupid and if you're stupid, you're poor."

His first brush with wealth came in the 8th grade, at the exclusive St. John's Military Academy in Wisconsin, a private boarding school where he lived with children from wealthy families.

"I felt that if these kids could be rich, as stupid as they were, this truly was the land of opportunity," he said.

After finishing at the top of his St. John's class, Filipowski applied to Harvard and Yale, expecting to get into one or both schools, but the Ivy League institutions rejected him. He returned, heartbroken, to Chicago and enrolled at the University of Illinois at Chicago, dropping out a year later.

Despite the setback, his first wife, Janet Filipowski, recalls he "had this flair about him." Filipowski took her to fancy restaurants and brought her flowers on every date. She fell in love with him, she says, because he cried when they saw the movie "Love Story." About six months after they met, he proposed.

Filipowski launched his career in the computer equivalent of the mailroom. He worked the 4 p.m. to midnight shift at the Time-Life Building on Michigan Avenue, changing printer paper and feeding punch cards into the primitive machines. During breaks, he would sneak into Time's video library, where he taught himself COBOL and other programming languages.

His talent for technology became apparent when he was hired at Motorola Inc. as a computer programmer. The 19-year-old Filipowski and another young programmer, Ray Nawara, would speed-read technical manuals and make cutting-edge computing look like "child's play," said Bob Pappas, who supervised the two. "I've never seen anything like it before or since."

Filipowski's career took off.

After a stint at A.B. Dick Co., he reunited with Nawara at Cullinane Software of Boston, where ace salesman Filipowski rose to become chief operating officer.

As the company prepared to go public in 1978, founder John Cullinane wanted Filipowski to pitch the firm to potential investors.

"Flip would get up and say almost anything," Cullinane said. "If it turned out he was wrong, it didn't seem to faze him. He would go on."

But Filipowski went too far--a habit that would hurt him later in his career, too.

He devised a plan to split the company into three parts, even though the firm had just told a much different story to investors.

Flip sent packing

Cullinane wasn't pleased. "He came on so strong and so aggressively, I had to rein him in ... and send him back to Chicago," he said.

So Filipowski returned to his hometown, quit his $100,000 job at Cullinane and started his own firm.

"I remember feeling like I was sweating at the same time I was taking a shower," said Filipowski, recalling the day he left Cullinane.

The company Filipowski started, DBMS Inc., specialized in what he wanted his former employer to do--develop software applications, education and consulting services for the Cullinane database system.

Joined by his friend Nawara, Filipowski installed in DBMS a culture similar to those in today's Internet start-up companies--spurning business attire, centralized authority and the 40-hour workweek. At 10 p.m. most weeknights, Filipowski and most of his employees were still at the office.

"His mind was working 24 hours a day," Janet Filipowski recalls. "He'd wake up in the middle of the night talking computers. I would poke him in the ribs and say, `Be quiet. I don't understand one word you're saying.'"

Filipowski and Nawara were inseparable, often traveling together to Las Vegas, where Filipowski displayed a penchant for gambling and breaking rules.

On one trip, Filipowski approached a $5 blackjack table and plunked down a bet of several thousand dollars. When the dealer said he couldn't cover it, Filipowski glanced over at the pit boss, who instructed the dealer to disregard the rule.

DBMS expanded to 450 employees, but its spending grew even faster. Steep salaries, research and development, and expensive office space forced Filipowski to fire 100 employees.

At the same time, Filipowski began clashing with Nawara. Filipowski wanted the company to focus on a new IBM database product, while Nawara thought it should stick with the Cullinane system. The disagreement became personal.

In one incident, the two sat at different tables during a company dinner in the Bahamas. Each started ordering more and more expensive dishes and drinks off the menu, upping the ante with items like Napoleon brandy. "Each wanted to see who could outspend the other," said Pappas, who had become a DBMS executive. "It got to be absurd."

Several former DBMS employees said Nawara resented being thought of as the lesser partner in the company and began bad-mouthing Filipowski to others at the firm.

In November 1986, Filipowski took the problem to the board of DBMS, which agreed that Nawara should be fired.

But Nawara didn't stay away. With the support of new investors, Nawara returned to the offices of DBMS four months later and, in a kind of corporate coup, took over.

When Filipowski arrived at work, he was ordered to leave and security guards escorted him from the premises.

Once as close as brothers, Filipowski and Nawara have barely spoken since their fallout. Nawara declined to be quoted in this article.

Most people who talked with Filipowski after he was kicked out of DBMS remark on his resiliency.

But his wife had a different impression.

"That's when he changed," Janet Filipowski said. "He put a shell around himself. I think he was hurt so badly by it. And he was more determined than ever to make a big, successful company."

Filipowski called on rich friends to fund his new company, Platinum Technology International Inc.

"I really wondered if he was going to make it," said Art Friego, a friend of Filipowski's who was among the early investors. "I never expected to get any money back."

Filipowski's marriage was coming apart. Janet Filipowski's reaction to the DBMS debacle contributed to the problem. "I told him to get a real job," she said. "He never forgave me for saying that."

Filipowski's new company, which he started in the basement of his Lisle home, made and sold software to support the databases that companies use to conduct their routine business operations, such as payroll, inventory and marketing.

But DBMS, which had a similar product and mission, filed a lawsuit against Platinum, Filipowski and other former DBMS executives. The lawsuit asserted a variety of wrongdoing by Platinum workers, such as stealing DBMS' employees and customers.

Filipowski denied then--and still denies--the allegations in the lawsuit. But to settle the case he gave up his entire remaining stake in DBMS, which was worth millions.

Freed of that legal burden, he focused on Platinum, convincing employees that it was bound for greatness.

`Knute Rockne effect'

"Flip would walk into a room and start talking and you would think we were an enormous company," although at the time it had only about 200 employees, said Corey Ferengul, Platinum's director of product integration. "It's kind of a Knute Rockne effect."

Filipowski's expensive tastes were reflected in the annual retreats for the company's top salespeople he held at the best hotel in Maui.

A concierge service sent flowers, ordered theater tickets and even planned weddings for employees. People who adopted children could take time off and receive $5,000 in assistance. Employees could even get pet insurance.

Filipowski worked tirelessly. He went on calls with salesmen, spent days with customers and participated in technical meetings that sometimes lasted 16 hours. "He would be there for every minute," said Mark Fetherolf, a Platinum executive. "I've never seen anybody make that kind of management style work the way he did--not micromanage, but get into every corner of the company."

Once a rumor spread through the company that Platinum employees in Asia had started wearing more formal attire to conform to the local business culture.

"He left this message that said, `If anybody in this company tries to do this I want to hear about it. It's not going to happen here,'" Fetherolf recalled. "He got so much mileage out of that, (especially from) the engineers. These guys wanted work and lifestyle and all that to be integrated, and he was their champion."

Around 1992, the database market began to shift. Companies began to scrap mainframe computers in favor of client-server systems, in which employees at all levels were given greater access to corporate information.

The movement spurred consolidation among softwaremakers and set off a round of acquisitions and mergers in the industry. Filipowski was left with a decision: whether to unload Platinum to the highest bidder or become an acquirer himself.

He charged ahead, gobbling up smaller software companies--often paying top dollar. And to inspire his employees, Filipowski vilified Platinum's competitors.

Computer Associates, a software company that was growing even faster than Platinum, emerged as enemy No. 1--a cheap, uncaring corporate behemoth, in Filipowski's view.

Platinum employees followed Filipowski's lead. They made fun of Computer Associates executives and flaunted T-shirts that read, "Friends don't let friends buy from CA."

But when Platinum ran into trouble in 1998, missing its quarterly earnings estimates, Filipowski changed his view of CA.

The earnings shortfall was partly due to a delay in completing an important new product. The high spending hurt, too: Revenue per employee at Computer Associates was about three times the $129,000 revenue per employee at Platinum.

Platinum's stock tumbled from more than $30 to under $10 per share, making the firm a prime target for a CA takeover.

To his employees, Filipowski's attitude toward CA seemed the same as ever. On more than one occasion he swore that he would never sell.

Still, when Sanjay Kumar, the president of Computer Associates, called to arrange a meeting in the spring of last year, Filipowski agreed.

Over dinner in a restaurant near Filipowski's sprawling North Carolina home, Kumar offered to buy Platinum's stock for nearly three times its going price.

Filipowski said he at first said no, saying the deal could fly only if Computer Associates took the unheard-of step of putting several billion dollars in an escrow account and promising to let Platinum keep the money even if antitrust regulators stopped the acquisition.

"He reached across the table and said, `Done deal,'" Filipowski recalled. Kumar couldn't be reached for comment.

At the time, the $3.5 billion deal was the largest sale ever for a software firm. Filipowski, who personally pocketed about $290 million, expressed little remorse about going back on his earlier statements, saying that in the end he had no choice.

Soon after the sale, Filipowski launched Divine Interventures.

Employing his marketing panache, Filipowski billed Divine as an "Internet zaibatsu," a reference to corporate clans that built Japan into an imperial power before being banned after World War II.

The fanfare worked, as the riches from the Platinum deal and the boom in technology stocks made Divine an easy sell. Filipowski quickly raised $400 million.

Microsoft Corp. was an early backer of Divine, as were Dell Computer Corp., Compaq Computer Corp., Hewlett-Packard Co. and Chicago's Aon Corp. Numerous local businessmen, many Filipowski's personal friends, also invested in Divine. (Tribune Co., which owns the Chicago Tribune, has a $2 million stake in the company.)

The city joined the excitement over Filipowski's new enterprise, contributing $14 million in tax increment financing for Divine's planned Goose Island headquarters campus. Last December, Mayor Richard Daley and Filipowski held a joint news conference at Goose Island, where the mayor announced how the city planned to become a "high-tech hub."

Selling to Chicago

Promoting Divine, Filipowski spoke at business forums throughout Chicago declaring that the city's corporate elite needed a swift kick to join the new economy.

While the speeches sounded impressive last fall, they ring a little hollow now as the red-hot technology market has cooled.

The tech-heavy Nasdaq stock market is trading 25 percent below its record high in March, and investor interest in speculative technology ventures has declined sharply.

Divine, which had rapidly grown to more than 750 employees, laid off 29 people last month because of a slowdown in deals. Construction at its $62.9 million Goose Island campus, which was originally scheduled to open this fall, has been delayed and could be canceled. Like many Internet companies, Divine has never posted a profit.

As investors have soured on technology stocks, Divine-style "incubators" that nurture Internet start-up companies have been hit especially hard. Two similar companies elsewhere that have already gone public, CMGI Inc. and Internet Capital Group, this year have seen their stocks plunge 66 percent and 85 percent, respectively.

Divine also faces an increasingly crowded field as hundreds of existing and new companies start incubators around the world.

"A year from now there will be blood in the streets," predicted Charles Rutstein, an analyst with Forrester Research. "There's too much money flowing into these things."

Divine's lead investment banker, CS First Boston, tried to postpone the company's stock offering until the climate improved.

Filipowski's response reflected the gung-ho attitude that has marked his entire career: He fired CS First Boston and replaced it with another firm that was willing to be more aggressive.

Then Filipowski and the new firm, San Francisco-based Robertson Stephens, jacked up the price of the shares and the total amount of cash to be raised in the initial public offering, from $140 million to $200 million. The IPO could give insiders a chance to unload some of their stock for a profit after a mandatory waiting period. Filipowski declined to comment on the pending public offering.

To some, the plan to proceed with the offering sounds almost as dicey as the quip long ago to buy out Harvard Business School.

Those who know Filipowski see the rush to market as almost inevitable, given his hard-charging style and the get-rich-quick culture of Internet enterprises.

Now the stock market is due to weigh in on whether Filipowski has what it takes to lead corporate Chicago--belatedly--into the on-line Gold Rush.

Tribune reporter Ray Gibson contributed to this story.