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PLUG IN Rich Wiklund's name on an Internet search engine and a rough outline of his seven-year ride on the dot-com roller coaster flashes onto the screen.

There he is back in 1994, going it alone in his basement, doubled over with stomachaches as cash dwindled and workdays stretched past midnight.

Scroll down a bit and find him on a brief high in early 1995, just after his company was bought by Lancaster Information Group, a Pennsyvlania-based printing firm.

Finally there are traces of the present-day Wiklund and his latest venture, PortCD, as it morphed into Avideon Corp. earlier this year. At this point, Wiklund can be found, fingers on the keyboard, working in a borrowed office in Hunt Valley, still waiting on the next deal to come through and still battling the occasional stomachache.

"Stress," he explains. "And the fear of possible failure. But you also get the highest highs, and you can get them the same day, minutes apart." Which, at age 34, makes him wonder: "At what point do you say, all right, this is a success? When do your friends say, 'Hey, this guy's really done it'?"

Wiklund is hardly alone with such concerns in the sprawling amusement park called the dot-com industry. It's a crowded, boisterous place where the rides seem to crash as often as they thrill, some from the weight of debt, others from their breakneck speed, leaving customers behind even as they outpace competitors.

Dave Kelley, currently between jobs, likens a dot-com career move to "trying to jump on a train at 100 mph, and you're hoping you're jumping into the right car. ... I hate to paint it as some kind of adrenalin junkie, but [a dot-commer] is a person who can see an opportunity and take a few risks."

The popular perception of this workforce is that of a wired - literally and figuratively - pack of 20-somethings in black clothes and sneakers. They're the cliches you see on dot-com ads, with their scooters and trendy haircuts, expected to either make their first million or their first three job moves within a year of starting their careers.

Plenty of those types exist. But on the entrepreneurial side of the business, propelling the industry from its earliest days, a lot of the 20-somethings have become 30-somethings. Business plans once scribbled on the backs of napkins or hashed out over a few cups of latte have evolved into detailed tomes designed to please increasingly wary venture capitalists, whose purse strings aren't nearly so loose as in the boom years that led to the tech investment binge of 2000.

Ask venture capitalist Frank A. Adams for his take on the dot-com crowd and he'll start by describing entrepreneurs in general.

"Entrepreneurs are unique people," says Adams, president of Grotech Capital Group in Timonium. "They are about passion, risk taking, and they generally have a good head for business. Now what we have seen over the last four or five years [with dot-coms] is the age of the entrepreneur dropping dramatically, and while they all have the passion and energy and the willingness to take risks, they don't all have a good head for business. ... They typically don't have financial skills and don't understand the power of cash, or the crisis that comes with lack of cash."

Look at Wiklund, for example.

Back in '94, about all he'd done with his journalism degree from the University of Richmond was to help start a desktop publishing business in suburban Virginia for a Richmond-based printing company, Cadmus Journal Services.

He took a look around at the state of the art and decided he could do some of the same things better, and faster, via the Internet. So, he quit his job and formed in his then Baltimore City home, marketing to the hundreds of various journals and associations in the fields of science and medicine.

Helping him get started were his father-in-law and his wife's uncle, investing nearly $30,000 apiece. His own family wouldn't throw in a dime. They thought he was nuts.

Learning fast

A few months later he was wondering if they were right. His wife had just quit her job to have their first child, and he, as sole breadwinner, was working out of their basement almost nonstop, fast discovering what his father-in-law meant when he'd cautioned, "You don't know what you don't know."

What Wiklund didn't know was practically everything about running a business and making deals, so he learned by trial and error, maxing out his credit cards to keep the venture infused with cash. He went back to his father-in-law and his wife's uncle for an extra $30,000 apiece.

As the business began to grow, he developed the first online catalog for Waverly Press in Baltimore. He produced an online version of the American Cancer Society's magazine, the Journal of Cancer. In early '95 he moved to a "business incubator" dormitory on Key Highway, across from the Museum of Industry. Huge cranes and equipment from Baltimore's past business booms loomed right outside his window by the waterfront.

By spring his company had been snapped up by Lancaster Press, which was itself bought soon afterward by Cadmus, putting Wiklund back to work as a vice president for his original employer. Not only was he able to pay back his family investors with a 20 percent return, he also had a steady, well-paying job with nice benefits.

So, of course, he was soon itching to quit and start his own dot-com company again.

Dave Kelley, 34, well understands such urges.

Early 'Net worker

While Wiklund was working in the basement of his Baltimore County home, Kelley was preparing to come aboard as one of the first dozen or so employees at Clarknet, one of the early Internet service providers in the Baltimore area. He was vice president of marketing, working closely with guys who would soon be spinning off their own dot-com ventures - Mark Nugent, founder of BusinessMonkey; Bill Twigg, founder of Alexander and Tom; Steve Crawford, founder of ZeroToEighty.

Kelley stayed aboard when Clarknet was bought in 1997 by another new venture, Verio, and he was aboard when Verio went public in 1998, making a decent chunk of change for his troubles. He later left to become vice president of sales with Nexus Communications, but soon left when that position turned out to be more of a sales job than a 'Net job. That's when he became a partner with fledgling Rand Interactive, a Baltimore producer of some of the flashiest Web sites going.

Then Rand was bought by Change Technology Partners, in late 2000. Kelley left Change Technology a few weeks ago to scout for his next opportunity.

Contrast all those moves to the career path of Kelley's father, who worked 30 years in sales for IBM, living by Big Blue's rigid dress code - white shirt, tie, blue pants, no facial hair - while knowing he'd probably have his job for as long as he wanted.

Such assurances no longer exist, but in dot-com land neither does such rigidity.

"That's another thing I like about this industry," says Kelley, of Ellicott City. "It's a lot more relaxed."

That goes for decision-making, too.

"I loved the time I spent at Clarknet, when we had five or six guys and we'd get into a room and be able to make decisions and build things in a single afternoon."

Indeed, says Adams, the venture capitalist, while the strategic planning of dot-com people tends to be "a bit myopic, on the other hand, because of this they are very nimble, and can change direction on a dime."

One reason the dot-coms are so nimble is that they have to be, because the technology they're built on changes so fast.

"It changes literally every day," Kelley says. "It's morphing as we speak. I'll go home and check my e-mail and something new will be developing. That's the high, really, seeing things as they change."

Unfortunately, customers don't always keep pace. "A lot of them," Kelley says, "just learned how to put an attachment onto an e-mail."

For Wiklund, this brings to mind the way relatives used to mail him Web addresses they'd clipped out of newspapers and magazines back when he was first getting into the business, with notes saying things like, "Here's a Web address. Thought you might be interested." The Internet seemed like such a strange and foreign new world except to those already immersed in it.

Keeping up to the minute

But any business moving this fast generally requires its practitioners to put in long hours to keep pace themselves. Add that to the already tough demands of entrepreneurship - "their job is their mistress," Adams says - and you've got a formula guaranteed to strain family life.

"I think it is extremely hard on relationships, quite frankly, and I think it did contribute to the loss of mine," says Kelley, divorced father of a 3-year-old girl. "At Verio I was working close to a hundred hours a week, with a lot of travel and a lot of holidays. But, again, no regrets, because it got me where I am now, and financially my daughter is set. But it does take a toll."

"It hasn't been easy, that's for certain," adds Wiklund. "I've had to take a good hard look at how I've behaved. In the beginning of [his current venture] in '99, I spent every waking hour and far into the night working and thinking about the business. My wife told me several times, in several discussions, 'You've got to realize there is more to life.' ... But it is interesting I'm still married, and I intend to stay that way."

His latest company, Avideon, a partnership with two other dot-commers, could be on the verge of a business breakthrough, though it hasn't come easily.

Avideon tries to sell corporate clients on the idea that they can lure more of their customers to their Web sites by supplying the customers with promotional CDs. Not only do those CDs help link the customers to the Web site, they're also designed to relay customer preferences to the company running the site.

Clients so far have included Toyota and Heineken, and as Wiklund waits to see if they'll take the plunge for multimillion CD orders, he has stretched finances toward the limit. He laughs when you ask him how much he's in for.

"If I let it out and my wife read it, she'd freak out. On a monthly basis I'd go to the bank and take out a cash advance on my credit card to pay my mortgage. In June we're going out with a test for credit card marketing with a major bank. If it works, it could be an order for a million CDs. Or it could be nothing. And we are about to sign a licensing agreement with a major music label to test our product with a platinum music CD. You get the highest highs - 'Wow, imagine what could happen!' - and then things get put off."

Kelley, by contrast, is taking a breather of sorts while he mulls his options. He has that luxury thanks to some of the dot-com stock sales of the past several years, and he's catching up for lost time with his daughter.

But soon enough it will be time to jump back aboard that 100-mph train, and even though the ride isn't always smooth, he wouldn't have it any other way.

"I've learned a ton, more than I ever could have in any MBA program," he says. "I've helped build a couple of companies and helped take another one public. I think no matter what I do, the Internet is going to have something to do with it. It's pretty much what I know."

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