Get Your Bet On!

To see MainStreet’s stories on Dealing with a Sudden Windfall, such as Putting Your Super Bowl Winnings To Work, What To Do With a $1 Jackpot, and How Not To Blow Your Budget On Betting, click here.

Ladies and Gentleman, start your brackets!

The NCAA basketball tournament is set to tip off and for the next three weeks some 37 million coworkers, basketball fans and non-basketball fans alike, will unite in March Madness by joining an office betting pool. 

The NCAA tournament brackets may be 65 squares meaning nothing (to some), but fill them in with enough winning college teams, and you could find yourself with a nice windfall (of Monopoly money, of course). At the same time, the odds are against most companies' bottom lines. Millions of workers are expected to follow this week's afternoon hoops action on CBS, CBS.com (CBS) or ESPN.com (DIS). In fact, the Chicago-based placement firm Challenger, Gray & Christmas, Inc. estimates that this year's March Madness could cost employers more than $1.7 billion in lost productivity.

At least companies can cut back on their corporate retreat budgets: March Madness is about team building, says Trev Rogers a sports handicapper with BetVega.com. “It is proof that men and women can have a friendly competition in the workplace,” he says. "Bosses seem to find it a nice diversion for a couple of days that allows for some bonding with colleagues you might not have known really otherwise." The fact that so many parts of the country are involved at once makes this tournament extra entertaining, adds Joe Sheehan, managing editor of BasketballProspectus.com. “Other sports playoffs are special, but there is something extra about the NCAA tournament."

Because the games are so unpredictable, there is no need for the casual or even unknowing picker to feel intimidated when filling out their bracket with the teams they think will win. “The college junkie overanalyzes and examines," says Rogers. "The secretary or girlfriend who ends up going by team color, logo, or mascot can end up winning the championship pool."

So if we’re all “picking” and not "betting" (gambling is illegal after all) what’s the key to winning all that play dough? One tactic Rogers swears by is to pick at least seven upsets in the first round, which is about the average amount each year, he says. “It’s good for leverage,” Rogers says. Just because a team is ranked high, does not mean it will go far. “The best teams almost never all advance,” says Sheehan. “The real trick is to pick the Final Four teams right.” When picking some people consult formulas like Jeff Sagarin’s for USA Today  (GCI) or Ken Pomeroy’s of Basketball Prospectus. “Very few people do it strictly one way," says Sheehan. “Go with your instincts,” adds Nando DiFino, a contributor to Sam Walker’s book on Fantasy Sports Games, Fantasyland. “You can blindly pick teams and still do well.  It’s got the same euphoria as scratching off a lottery ticket, just prolonged over a few weeks.”

But just like with the lottery or any other gambling, do not let your March get too mad. Even if you are betting legally in Las Vegas, financial advisers suggest you set a strict budget and stick to it. “Don’t bet more then you are prepared to lose,” says Cary Carbonaro, a financial planner with Family Financial Research in New York. “And, if you win, pay off any credit card debt  or your taxes.”  You could also start an emergency fund. Not surprisingly, Sheehan disagrees: “Fun money is fun money. You don’t spend it on bills! Buy a round of drinks for your friends or spend it on your significant other.” Either way, good luck!