Lessons In High Stakes Gambling

By Adam Coughlin, Managing Partner at York IE

When I was in the fifth grade, my older brother and I were in the same school for the first time ever. At the time, as he continues to be, my brother was my hero. Yet the only time the entire school year that we randomly bumped into each other was the day I passed him on my way to the principal.

I will never forget the long march from the playground, down the eighth grade hallway to the principal’s office. My brother saw me, gave a loving wave, and I lowered my head in shame, acting as if I didn’t see him.

I was hard to miss, however, because I wasn’t alone. I was marching in a procession of fifth grade boys — all on our way to the principal’s office. Our crime? We were guilty of simply participating in a hallowed McKelvie Middle School tradition. We were playing in a playground basketball tournament. My own brother even played in it years earlier.

Three players per team. $5 per team to enter. Tournament style. Winning team gets the pot.

I guess, to the school administration, this was called “gambling.” I guess we were the only boys to ever get caught. I am pretty sure we had to call our parents, which in some ways was the most perverse punishment possible.

But I still, nearly 25 years later, object to the term gambling. If we were randomly putting money on teams we were watching on television then yes that description would apply. But we were not. We were playing in the game. We had a direct impact on the outcome.

We were not gambling. We were betting on ourselves.

And I think it is bad form to tell a young child that there is anything wrong with betting on oneself. It is actually one of the bravest things you can do and often is what separates “super talented employee” and “startup founder.”

When I left Oracle this past summer to strike out on my own, I was once again betting on myself. If I am being honest, I was scared. And then a friend made an astute observation:

“Do you trust your future more in your own hands or Larry Ellison’s?”

It was such a simple way of putting it but it became so clear. I would be a fool not to bet on myself.

And that reminds me of another objection to my fifth grade discipline. I wasn’t just betting on myself. I was betting on my team. I was putting my faith in other people. I was combining complementary skill sets that made the whole greater than the sum of its parts. That is a valuable lesson, which, since we weren’t allowed to play, I was denied seeing through.

But here’s the thing when you bet on yourself: sometimes you lose. And sometimes you win.

The teammates I chose for that fifth grade tournament were Stefan Gagnon and Kyle York.

Yes, Kyle and I bet on each other back then. And, twenty five years later, we’re doing it again. But this time, I’m marching down the hallway with my head held high. This time, no one is going to stop us.

-Adam