Funny Money: Dribbling All Over Your Brackets for Fun and Profit

This is the year: Get ready to crush your local March Madness bracket and rake in the cash — even if you know absolutely nothing about college basketball.

The fun and profit of NCAA Bracketology

You’re supposed to be working right now, and that’s just what you’re doing. It’s just that you’re not focused on any of that lame, boring stuff your company is paying you to do. Instead, your focus is on the shared national obsession of NCAA Tournament brackets.

The goal here, as with work-work, is to make some good money, possibly by owning your office pool and winning bragging rights away from Steve in accounting who has won the title three years running.

Never mind that you’ve entered for the last 10 years, have had your bracket obliterated after the first weekend every time and sworn you would never again waste time and effort on such a fool’s errand. This is your year, because you’ve learned from your mistakes and will do things differently this time around.

Here are some suggestions to help make this year’s bracketology endeavor more profitable:

Play moneyball

Attack your bracket from the brainy, research-based perspective. Pore over stats compiled by such numbers-crunchers as and FiveThirtyEight.

Scan each team’s schedule to evaluate scoring tendencies, factor in the location of the games and compare your evaluations to Las Vegas betting lines. Familiarize with a few bits of knowledge shared by those in the know: A 16 seed has never topped a 1, and at least one 12 seed — and usually a 13 seed — wins at least one game every year. Also, be aware that a double-digit seed almost always makes it to the Sweet 16, so choose a dark horse and hope it’s the one you ride to glory.

Forsake your school

Sure, it’s fun to make believe and click your alma mater to improbably win game after game, but it doesn’t pay to let loyalty cloud your judgment.

Do your bracket a tough but necessary favor and eliminate the school that was foolish enough to hand you a diploma as soon as they face a higher seed, if not a round before. While your’e at it, do the same for the hometown favorite. Because everyone around you is more likely to give Homeboy U the benefit of the doubt, you’ll get an edge by bouncing them early if they choke and ruin everyone else’s bracket but your own.

Choose at random

Despite your best laid plans, your educated guesses and reasonable assumptions, you’re probably no more likely to pick the correct Final Four than the little old lady in accounting who can’t pick out a basketball from a golf ball.

So let random chance be your aid, and submit an alternate bracket decided almost entirely by coin flip. Don’t do anything so silly as pick a 16 seed over a 1, but just about any other contest is fair game. It’s a can’t-lose proposition. Either your coin flip bracket will give you a fighting chance after your regular one fails, or that one will flop and you’ll get an ego boost from the knowledge that your brains outperformed blind= guessing.

Enter free contests

Why waste money on your office pool, gambling for small potatoes, when you can go for lotto-style money for free?

The internet is flooded with massive bracket competitions. I’m most intrigued by the Quicken Loans Billion $ Bracket Challenge, which is offering a billion bucks to someone who can do the impossible and pick the perfect bracket.

If you want to settle for a measly million dollars, head over to the Sports Illustrated Bracket Challenge. The ESPN Tournament Challenge offers $50,000 and a trip to a Final Four, and the CBS Bracket Challenge offers a plain ‘ol Final Four trip with no big money attached. If you win a big-money contest, your next bit of on-the-job side work may be penning your resignation letter.

Read more:

Want FREE help eliminating debt & saving your first (or next) $100,000?

Money Under 30 has everything you need to know about money, written by real people who've been there. Enter your email to receive our free weekly newsletter and MoneySchool, our free 7-day course that will help you make immediate progress on whatever money challenge you're facing right now.

We'll never spam you and offer one-click unsubscribe, always.

About Phil Villarreal

Phil Villarreal writes Funny Money weekly for Money Under 30. He lives in Tucson and works for the Arizona Daily Star. He's also an author, blogger and Twitterer.