Game of Risk

Look both ways before you cross the street.

That's the first rule, and the others we also know all too well. Don't take candy from strangers. Don't swim for an hour after eating. Careful what you touch in the woods. Wear a bicycle helmet. If you're lost, find a policeman. Fasten your seatbelt. Don't play with matches.

Don't take risks.

All good rules, of course, but most parents know to tell their little startups that rules are sometimes meant to be broken, or at least bent. Yes, that smiling child with the missing tooth at the playground is a stranger, but he's harmless. Making a snow angel could result in the sniffles, but let's do it anyway. Sure, after your bike's training wheels are removed, you might fall; but then again, you might not.

Not taking a risk is taking a risk.

Starting a business is a risk in itself, but in a way, getting a new company off the ground is the easy part. If you started with little, you had little to lose. But once you have employees-whether it's five or 500-what you do or don't do may affect the lives of them and their loved ones. You have customers. Suppliers. A reputation. A bottom line that, if not cared for, could lead you back to the bottom. Take a risk now, and everybody may suffer the consequences.

Or reap the rewards.

We talked to three entrepreneurs who embrace risk even more than your average business owner does-taking leaps when the economy is sour, betting on unproven businesses and trusting their guts for all their major decisions. Take a look-if you can stomach it.

This article was originally published in the April 2002 print edition of Entrepreneur with the headline: Game of Risk.