Oswald Letter

Despite what I put on my bracket, I’m rooting for the underdog

Basketball tournament bracket with spot lighting on wood gym floby Dan Oswald

The NCAA men’s basketball tournament kicked off last week. It’s known as March Madness. Even if you’re not a college basketball fan, you may have filled out a bracket at home or for your office pool. More than 10 million people filled one out this year.

Every year, my wife, our kids, and I fill out our brackets in the spirit of a little family competition. When my daughter was younger, she would ask for my help in filling out her bracket. Her questions weren’t about how high the teams were ranked or their basketball abilities. Instead, she wanted to know the teams’ colors, their mascots, or in which state their schools were located. She would pick accordingly and sometimes would still be competitive with the rest of the family. That’s just the way the tournament works. It’s unpredictable.

This year, the clear-cut favorite is the undefeated University of Kentucky Wildcats. I heard the other day they have a 40% chance of winning the tournament. There are 64 teams in all (I don’t count the “play-in” games). If each of the teams had an equal chance of winning, each would have a 1.56% chance of being crowned champion of the tournament. So with a 40% chance of winning, the Kentucky Wildcats are clearly the dominant team.

I hope they lose. I’m sure I’m going to hear from the Kentucky nation, but I can’t cheer for the favorite. I don’t care if it destroys my bracket—I love to see the underdog come out on top. Every year, I pick all my teams and then cheer against them as soon as they play a competitive game with a lower seed. Who can’t cheer for little Georgia State, a 14 seed, as the coach’s son hits a three-point shot at the buzzer to beat 3rd-seeded Baylor University?

With four regions in the tournament, the teams are seeded 1 through 16 in each region. A 14 seed like Georgia State is one of the 12 lowest-seeded in the tournament. The lowest-seeded team to win the tournament was an 8th-seeded Villanova Wildcats. That was way back in 1985—30 years ago. Maybe this is the year that a new team will become the lowest-seeded team to ever win the tournament. I hope so!

So why do I so love the story of the underdog coming out on top? It might be that I grew up in a small town in Middle America and want to believe that great things can be achieved from humble beginnings. More likely is that I manage a small company and believe that we’re capable of competing with anyone. That as a small business we can be more creative, more nimble, and more resourceful than our bigger competitors. That as a small business we can take on anyone and somehow prevail.

I love to hear stories about small companies that have succeeded. I like to know that Apple started just 40 years ago in a garage in Cupertino, California, taking on the likes of IBM and today sitting atop the Fortune 500. I enjoy hearing the story of Whole Foods Market, which was started by a 25-year-old college dropout and his 21-year-old partner with $45,000 borrowed from family and friends. Today, the food store chain is also a member of the Fortune 500, with revenue in the billions. I can’t hear enough stories like that of Starbucks, which was started by two teachers and a writer with less than $10,000. The founders sold their business 16 years later, but the company they founded now has revenue exceeding $16 billion.

It’s reassuring to know that the little guy can compete. It’s comforting to know that companies can overcome humble beginnings to become the dominant player in their industry. I like to know that David can beat Goliath. So for me, I’m going to continue to watch the NCAA tournament and cheer for the underdog. And I’m going to do so knowing that every time the lower seed succeeds, it reconfirms my belief that anything is possible if you believe in yourself, believe in your teammates, and believe in your mission.

5 thoughts on “Despite what I put on my bracket, I’m rooting for the underdog”

  1. I wholeheartedly agree with rooting for the underdog! Except this year…the number one seed Wisconsin is due for their big day.

    And I have offspring who have that entrepreneurial spirit. They strive to be the business that began in the garage…one is working right now to get her business started. She is participating in Jacksonville’s One Spark crowd-funding event next month to raise the upstart money for her idea. Who knows…you may be writing about her next…

  2. I love your article, it would have been better if you said something about my school, Hampton University Pirates. We faced KY with our 17-17 record. It was David vs Goliath (34-0) meets the real world. We joked about having Jesus on the Main Line but for real we were hoping for a repeat of 2001 when people counted us out and Iowa (2) woke up the next morning to Hampton(15) moving on to the second round. That IS why it is called March Madness.
    When people write you off, work even harder, prove them wrong. Succeed not because you need to prove a point, succeed because it is in your DNA, your Destiny, it is in you!!! #BelieveinHamptonU #PirateNation #Let’sGoPIRATES

  3. Jeannie,

    On Wisconsin! I lived in Milwaukee for about 10 years during my youth. I can’t say I’m a big Badgers fan, but it’s hard for me to cheer against them.

    And WHEN you daughter makes it big as entrepreneurs please let me know so I can share her story!

  4. Robin,

    Nothing would have made me happier than Hampton once again working its 2001 magic and sending the top-seeded Kentucky Wildcats home!

    And I love your words of inspiration. So true!

  5. I recently read that we root for the underdog because in most cases WE are the underdog in some facet of our life. Let us not forget American was the underdog by miles but our heart won.

    There is nothing more inspiring than a good underdog victory. Nice article.

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