The Entrepreneurship Of March Madness

March Madness and Entrepreneurship

Mexican-born entrepreneur Pablo Esteves shares his take-out on the unexpected lessons to be learnt from participating in a US sporting event as an outsider.

This is my first time – being from Mexico – participating in the all-American pastime of filling out a bracket for March Madness, the single-elimination US college basketball tournament that takes place every spring. This means that before the very first tip off, I must pick a winner for each of the 64 games in the tournament, then watch the scoreboard seal my fortune over the next two weeks until the final Championship game. I’m playing in two pools: one with my girlfriend’s family, the other with work colleagues. Ninety nine percent of the people I’m playing against are Americans – the only exception being my colleague Chris (he’s Canadian.) In both pools – the brackets doggedly confirm each time I check on them – I am the bottom feeder.

Why take advice from someone who lost not one but two basketball pools this year? Because as any seasoned entrepreneur will tell you, failure is not a bad thing; there’s learning in failing. And even better, I’ve learned from some of my few successful picks. Learning from success gives me better understanding of what works. This year’s experience, both the successes and the failures will help me achieve a better result next year.

The highs and the lows of picking winners and losers, the anticipation and the disappointment round after round. This sort of madness is not unlike being in startup. In fact filling out a college basketball bracket has some surprising similarities to pursing an entrepreneurial endeavor.

To pick a winner, you have to do your homework. Having followed the basketball season is an obvious advantage when filling out a March Madness bracket. It helps to know the players, their individual strengths and weaknesses, their successes and injuries. This is the same information gathering and pattern recognition process an entrepreneur employs when launching a new product, identifying a niche or pulling off a pivot. It’s the innate analytical ability that enables a smart entrepreneur to connect data, make smart decisions with confidence, and identify opportunities that others might not see.

Sometimes a long-shot pays off. A good March Madness tactic is to identify those “underdog” teams that could upset a favorite. For example this year, the Florida Gulf Coast Eagles (seeded at 15) had an unlikely win over second-seeded Georgetown. Most people probably picked Georgetown, so anyone who actually chose Florida Gulf for the win earned points while everyone else was eliminated of that bracket. Entrepreneurs must be able to smartly identify these long-shot opportunities of which their competitors are still unaware. You could go “chalk” – always pick the favorite, or the most obvious choice – or you can bet that upsets like Florida Gulf will happen.

Trust your gut feeling. You can make all the research you want, but in the end you have to fill out the bracket and predict the winner. Sometimes, you just have to go with your gut feeling, whether it’s during March Madness or an entrepreneurial endeavor. Bold choices sometimes lead you to a win, other times they blow up in your face. Being an entrepreneur means having the guts to take a “leap of faith,” to follow through, remain resolute and strong in the face of failure, and to change or pivot in the right moment.

Seek the advice of the fans. Being a good entrepreneur is more than solely relying on analytical skills. It entails getting input from others, to find mentors and hire people smarter than you – people smarts. For example, I should have asked my American friends to give me a point or two on my bracket choices. It’s also important to use experience, practicality, and common sense – i.e. street smarts. And finally, let’s not forget, you have to try new and unexpected ideas, you have to innovate in order to grasp patterns and see opportunities that no one else sees. Creative smarts. The ability to mix these four “smarts” will make you a better entrepreneur. And, with a bit of luck, help you win your office pool.

Luck helps. Just like in an entrepreneurial endeavor, Lady Luck always has a say in the matter when filling out a bracket. Regardless of the amount of research you do about the player’s height or the coach’s playing style, who you asked for help or advice, and how confident you might be with your choices, when it comes down to “the” game, most times you can’t control the outcome– you can’t determine if the point guard broke up with his girlfriend the night before, or your competitor launches their new website overnight. How can you make yourself luckier? Act with humility, optimism, and genuine intellectual curiosity; you’ll find yourself developing a lucky attitude in no time.

So next year, when time comes for you to fill your March Madness bracket – or in your future entrepreneurial endeavors – look at all the predictions, statistics and data you want and take them with a grain of salt. Be smart about your picks. Go with your guts. And hope for a little luck. Either that, or ask your favorite grandmother for some basketball picks.