Fred Wilson posted a great story from his grad school days today. I won’t spoil the tale, but it’s one of a genre that I’ve long enjoyed — the rogue who wins a difficult or unwinnable game by refusing to play in a traditional fashion.
The best known version in geek circles is Star Trek’s Kobayashi Maru, Starfleet’s unbeatable test that’s designed to test how a potential captain handles death, destruction and failure. Famously, only one cadet, James Tiberius Kirk, ever passed. He did so by hacking and reprogramming the simulation, changing the rules of the game and winning a commendation for his cleverness.
I have my own small-scale contribution to the canon. In fifth grade, I was sent weekly to a “gifted and talented” program at my neighborhood elementary school. (I was in parochial school at the time.) In my second week there, we were doing a paper airplane competition as a class exercise. Teams were split up to compete in contests for distance, tricks and aesthetic design — with a business twist. Each team got a stack of Monopoly money to buy supplies in an auction: paper, markers, tape, glue, scissors, paperclips, etc. There were a limited number of each item, and the bidding on, for instance, different colored markers, might vary. Each competition had a payout, and the team with the most money at the end won.
As we started the supply auction, it was clear that my new teammates hadn’t decided yet if I passed the sniff test. So I had to be really forceful as each item came up for auction and I insisted that we not bid at all. They got more and more uncomfortable as the markers, paperclips and other items were claimed by the other teams. I was entering the land of negative popularity very quickly.
I had taken careful note of the order of auction items — and the paper was last. I gambled that every other team would buy at least one item along the way, leaving us with the most money when the paper came up. As soon as it did, I bid all of our money for all of the paper, unable to conceal a wicked grin. “We win!” I exclaimed, as I smacked down the pastel-colored stack of bills on the teacher’s desk, knowing no one could enter a paper airplane competition without paper.
The teacher announced that my team would get A’s, but that we’d reset the competition with new rules to prevent my strategy from ruining the game.
We won the second version too.
I always try to remember this, and other stories of the “hack-to-win” canon when approaching a business problem. Sometimes the only way to win is to change the rules.