He’s ba-ack! Flip Filipowski, who more than any other individual dramatized Chicago’s Internet aspirations, has survived a billion dollar bankruptcy of his publicly held Chicago-based divine inc. and a personal downfall that left him with a significantly diminished fortune.

Of course, he started with the $3.5 billion he made by selling his startup software company, Platinum technology, in 1999 — an unheard of sum for a young entrepreneur at the time.

His official bio barely mentions the existence of divine — always spelled with a small “d” — or that Andrew J. “Flip” Filipowski was a CEO who raised $1 billion from the public in the fateful summer of 2000. That money disappeared into bankruptcy along with millions more invested earlier at pre-IPO prices by well-known Chicagoans including Bill Wrigley Jr. and Michael Jordan. And Mayor Daley approved a $14 million subsidy for Filipowski to build a dot-com incubator on Goose Island.

Filipowski’s “Internet zaibatsu” concept of melding a few dozen small companies into one mutually supporting organization incinerated virtually every operating unit within the zaibatsu when the Internet bubble burst in 2000.

How does Filipowski describe himself today?

“Somewhat humbled, but seasoned, scarred, a little older, hopefully wiser. . . . Never have I been more certain that life is just full of ups and downs, and that you sometimes have to end up reflecting back and saying that the downs, as tough as they are, are almost as bittersweet as the ups — from the standpoint that they define your life, like scars on furniture make them into antiques as a result of the damage.”

At age 55, his beard is more silver-and-gray than it was in 2000, but his ponytail retains its natural dark-brown color, and the attitude is only moderately subdued. There are still undertones of the bold warrior who defied corporate America when I interviewed him at the top of the Internet bubble in April 2000.

At the time he said, “Look, the fact is companies die. They die like human beings do. And they’re supposed to die to make room for the next generation.”
In that interview, he cited Sears as a prime example of a company that should die — and in hindsight, he was right. And also was right about his belief in the accelerating pace of change in the economy.

At the time, he was lionized by some for his tech-inspired vision, and resented by others for his, well, just about everything, from his name to his ponytail to his all-black dress ensemble, to his know-it-all attitude.

So when Flip’s public relations handler called to let me know that Flip was ready for a follow-up interview, I was ready to hear him out. After all, as Flip also said in 2000, “The bubble moves, and you gotta move with it.”

Like many of you, I wondered where he’d moved.

Though he has great affection for his native Chicago, where he was raised on the North Side by his Polish-born parents, Flip has lived and worked in North Carolina for the last two decades, including the divine era. He returns only infrequently to Chicago, where he maintains a residence, as well as some investments in real estate. And he’s the sole owner of Mastro Auctions Inc., based in Burr Ridge, an international leader in sports and Americana memorabilia auctions.

His main effort is as executive chairman and CEO of SilkRoad equity, a Winston-Salem-based holding company that includes more than a dozen ventures, standing alone as their own businesses but also doing business with each other in the Internet zaibatsu model resurrected.

He describes the SilkRoad technology unit as “an outsourcing firm that will handle the [personnel] recruiting process by using its technology to predict success in the hiring process, cultivate talent to make employees as productive as possible, and handle all aspects of training and ‘provisioning’ — such as laptops, Blackberries and other technology needs — for a client company’s employees.”

In other words, I ask, you’re sort of an outsourced HR department for client companies?
I’m greeted by a withering silence. Then: “We now have over 500 companies using the product, and we have been adding new customers at a faster rate than any of our competitors, and our suite of products has been judged by Gartner [a research organization] to be as good as exists in the marketplace, and I feel we have a shot at being one of the, if not the leading offerer in the hot market that is today in the HR space.”

Flip’s enthusiasm for his own creations is clearly undimmed. He explains that his new company grew out of the ashes of a small division of divine. This division, Eprise, was first acquired in the divine bankruptcy by a competitor that subsequently sold some of the assets back to Flip. He was interested in its “content management system,” which he built into a service that “replaces the traditional way of managing talent by using Excel spreadsheets and paper files.”

Filipowski explains the big difference in his service: “It doesn’t require them [client companies] to turn over their HR department. They just get on the Internet and start using the software. They don’t have to buy it or install on their computers. . . . The customer just gets a license to have their HR people log on, and get a personalized view of the application for their company, for the purposes of managing their processes.

“It is no longer feeling like a big leap for these companies to outsource. But what really popped our eyes was when Salesforce.com sold the concept that you can do customer-relationship management cheaper and better this way than by spending millions with a SAP or Siebel systems. Now we do it for HR.”

The concept might be revolutionary, but there’s a lot of the same old Flip.

“Right now, my No. 1 objective for SilkRoad technology,” he said, “is to be a great fun place to work, and have the kind of reputation — internally and externally — that Platinum technology had, where it is the greatest place on the planet for a tech person to work.”

While Flip was more than eager to explain his business concept, I was most interested in how his life and attitude had changed — or not changed — in the six years since his spectacular fall from grace.

Here’s Flip on Flip:

*On lessons learned: “The enormous lessons I’ve learned, I keep to myself, and I cry over them in my pillow. But I don’t know how to find the words to share the lessons with someone else.”

*On feeling guilty: “Of course I do, even when everyone tells you not to feel guilty, I do. Even when everyone else has forgiven you, the only person left is me. . . . The only place where it counts is between my ears. All else is irrelevant. These are sufferings and pain you can only experience yourself.”

*On being an entrepreneur: “If you have it in you to be an entrepreneur, then you are challenged by the risks and variety of factors that affect your effort . . . . Sometimes you get a great success like Platinum technology, and sometimes a great failure like divine. [This experience] had an enormous impact on my enthusiasm for entrepreneurial activity, and I had to fight tooth and nail to get it [my enthusiasm] back.”

*On doing things differently: “I’ve been far more cautious, far more dependent on getting the right talent in the right place, far more interested in risking only my own capital, rather than someone else’s.”

*On the importance of friends and family: “Without friends and family, there’s no way to get through this, and I’m deeply indebted to all my friends, many of whom are CEOs, and have given up more than they should have in terms of support and counseling and mentoring… It is impossible to get through a divine without a lot of that. And then it takes an enormous gumption to get back in the saddle and ride again.”

*And to his former investors: “To investors, large and small, I would do anything on the planet to eliminate their loss, help them regain it. I wish that penance was available in some rational way, but if you read the column you wrote six years ago, everyone at that time — like, most recently, those in the real estate market, or anywhere else — we all choose to be venture capitalists, and when we do this, we should know the risks associated with it.

“It doesn’t make me feel any better, but the truth is when you take a high risk it’s called that because it is!”

Terry Savage is a registered investment adviser.