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The Truth About Start-ups

What frustrates Dart is that this tenuous situation has stemmed in part from the distractions inherent in starting up. "You end up spending an incredible amount of time and management effort on things that other banks are taking for granted," he says. "Like designing our logo. Developing plans for our office space. Building facilities. Purchasing furniture. Installing computer systems. Training people. Developing personnel policies.

"At the same time," he continues, "you're hemorrhaging red ink, and you can't just sit back and say, 'Gee, I'm kind of conservative.' " Result: the bank made loans, says Dart, before it had airtight procedures to oversee them. And it made mistakes.

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Dart's main aim now? It remains, despite his troubles, similar to the one most start-up founders take to bed. "My number one goal is to have the bank survive. Pure and simple. Basically, I'd do anything to ensure that happening."

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THE HARD PART

Forget the strategic challenges a start-up presents; the emotional ones can be worse

Granted, leaving a $175,000-a-year job to start a business at home is probably not the prototypical entrepreneurial experience. Nor is doing that at age 27. Nor is pocketing about a million bucks, just a few years later, for 40% of the equity. Tim DeMello isn't representative of people who run four-year-old companies; he's been successful.

On the other hand, DeMello, founder of Wall Street Games Inc. (WSG), a marketer of national stock-market competitions, has struggled with at least one thing common to every company founder who sets out, as most do, utterly alone: an exposed and very vulnerable sense of self. "This is a way of life," DeMello explains, echoing countless others. "It's not a job, it's not a career, it's a way of life. I started a business for the sense of accomplishment, period." Trouble is, that sense of accomplishment takes a while to happen. And the lack of it can destroy confidence, summon doubt, and breed a paralysis no founder can afford.

"I came out of an environment with phones ringing a zillion times a day," says DeMello, who spent four years at Kidder, Peabody & Co. and two at L. F. Rothschild. "I believed if I reached for more, the rewards would be there, right then. I felt pretty confident of my skills."

He knew that new challenges -- marketing, accounting, advertising -- would tax that confidence. As difficult, though, was keeping his emotional balance without the support of a workplace. No more helpful, motivating colleagues; no more affirmations of personal worth from above (promotions, bonuses, commendations in the company newsletter); toughest of all, no more perspective of the sort you have when a job is something you do only at the office.

"When I started Wall Street Games, that was the loneliest period of my entire life. Those months I worked at home, I used to attack my wife in the driveway when she'd pull in, because I needed some form of companionship. Plus, you're focusing on something no one can truly appreciate. It's one of the scariest things in the world to sit there with an empty yellow legal pad and understand that nothing's going to happen unless I initiate it, so what in God's name do I do now?"

That vulnerability kept him from asking for help. "You don't want to try out your ideas on everyone, because you don't want a lot of people to say, 'This is crazy.' You're going through so much self-doubt as it is, you don't need anyone else's. You end up waiting until the idea is totally together before you start presenting it. I think you've got to go through that stage, but it's tough."

When outside investors paid $500,000 for a 20% stake, WSG moved into the marketplace. DeMello added managers and a flock of part-time student workers to staff the telephones over which customers buy and sell mock stock. As the personnel and infrastructure grew and changed -- there are now 10 full-time and 125 part-time employees -- so did the way the world dealt with DeMello. He started to become a star again.

"Perceptions are funny. In the office, new students will ask someone, 'Can I meet Tim?' And it's like, 'Yeah, you'll probably meet him next to the urinal.' But I used to think that way, too. We paint people to be bigger than life."

To maintain balance, DeMello says he "revisits the vision constantly" and doesn't look back on past victories -- or even perceptions of victories. "I read the Inc. story only once. I remember saying to people, 'It doesn't mean anything.' Hopefully it gives you a little boost of self-esteem, and you use it in your business if you can, but you go on."

Still, DeMello no longer feels like just another stockbroker. "I know how much work it was to get where I am -- and I don't mean I think I'm at the top; as soon as I say something like that I'll crash in two seconds. But I feel I've done something that isn't that simple."