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Winning the Finance & Investment Challenge Bowl

A first-place regional finish, and the round I lost by knowing the answer.


A full account, including the part where I threw away a round we had already won. That is the round I actually learned something in, so it is the one written up in most detail.

How the game works

Thirty questions per round, in three phases, single-elimination with a consolation bracket for teams knocked out in the first round.

Phase one is six questions, alternating between teams, multiple choice or true/false, on more or less anything financial. Five points for a right answer and nothing lost for a wrong one. They are there to warm you up and teach you something — one of ours was “is there an ATM in Antarctica?” The answer is yes.

Phase two is ten questions, still alternating, but now a miss can be stolen. Ten for a right answer, minus five for a wrong one, and the other team gets a shot at it.

Phase three is fourteen toss-ups. Buzz whenever you think you know it, including before the question is finished. Twenty for right, minus ten for wrong, and on a multiple choice you have to say the actual answer — naming the letter does not count.

Round 0: losing a round we had already won

We opened badly, missing the true/false questions and going down 5–15. Phase two fixed it. I answered most of them, but I ran every answer past the other two before buzzing, in case one of them knew something I did not.

By late in phase three we were far enough ahead that the other team could not catch us. Not probably — actually. With the questions left and twenty points each, there was no sequence of events where they won, provided we simply stopped answering.

So I answered. Early, without checking, and wrong. Minus ten, they took it for plus twenty, and a thirty-point swing reopened a round that had been closed. They kept going and passed us. We were seeded worse for the rest of the tournament because of it.

The mistake was not the wrong answer. The mistake was taking a bet with no upside: we could not gain anything we needed and could lose everything we had. I think about that round more than the one we won, and it is a large part of why I now build tools whose job is to tell me when I am about to do something like that with money.

Round 2: the quarter-final

A bye in round one, then a quarter-final that was boring for two and a half phases. Both teams answered nearly everything correctly and the toss-ups arrived with the score close.

Around question eighteen the other team changed gear — faster on the buzzer and right when they got there. One of my teammates told me, in as many words, to lock in.

I did. I took almost every remaining question before the host had finished reading it, and we won by more than a hundred points.

Round 3: the semi-final, and five minutes of deliberation

Menomonie had three of the four semi-finalists. We were the fourth. They had dominated this competition for years. We turned up in suits; they turned up in quarter-zips.

Halfway through the toss-ups: “Short answer — what is a balance sheet?” I buzzed before the host finished the word “answer”. I had taken a full year of accounting and competed at state level in Accounting II. If I did not know this one, I did not know anything.

What I said was: a financial statement that shows the different accounts in a company and how much is in them at that point in time, including assets, liabilities and owner’s equity.

The judges deliberated for nearly five minutes. Some said yes, some said no. The host thought I was right and so did the event coordinator, and the points stood. It put us ahead.

The round went to overtime. The overtime question was multiple choice, and I listened to it the way you listen when you do not know: A, no. B, no. C, no. I buzzed on the reveal of the last option and said D with total confidence. When my teammates asked afterwards how I knew, I had to tell them I did not. I knew it was not the other three. That is a completely different thing, and it is worth being honest about which one you are doing.

Then we chose not to answer the final overtime question at all. We did not need it, and answering could only cost us. It pushed the match into a second overtime, and we won there. That decision was the round 0 lesson applied about an hour and three matches later.

The final

The prizes were announced before the last round: a trophy, a place at state and $150 for first, $100 for second, $50 each for third and fourth.

Which meant Menomonie, with three of the four semi-final slots, had already banked $200 before the final started. I was not willing to add first place to that.

We won by roughly seventy points. Nothing like as close as the semi-final.

What I actually took from it

The most expensive thing in that tournament was not a gap in what I knew. It was a moment of confidence in a position that was already winning.

Knowing an answer and being able to eliminate the alternatives are different states, and treating them as the same is how people talk themselves into positions they cannot defend.

Declining to play is a move. When you are ahead and the downside is larger than the upside, the correct action is frequently nothing at all — which is most of what I have since read about position sizing, arrived at a year early and the hard way.