I’m not trying to brag, but I was the treasurer of my third grade class. I didn’t know what a treasurer of a third grade class was supposed to do. I still don’t know what I was supposed to do or even remember what I did after I was elected. All I knew was that I wanted to be in charge of the money.

I won the election due to a brilliant campaign centered around a simple concept: “In Kevin We Trust”. Below is a re-creation of the advertisement I passed out during on my way to election victory.

Kevin on a Ten

How many third graders do you know smart enough to come up with this marketing campaign? I'm not one of them (my mom did it)

It was a simple concept; even third graders know they want to trust their elected officials. I needed to make sure that all my constituents could trust me to be honorable with the class’ money (or whatever I was supposed to do).

Unfortunately, I wasn’t the right guy for the job. At least, not right away.

I wasn’t much of a football fan when I was a third grader, but I did watch the AFC Championship when the ’93 Buffalo Bills beat the Miami Dolphins. It was definitely the best football team I had ever seen in my life (probably because it was the only game I’d ever watched) and I was sure they would beat the Dallas Cowboys in the Super Bowl.

I was so confident the Bills would win that I made a $1 bet (when you’re in third grade, that’s like betting your life savings) with a kid at school on the Super Bowl. I took the Bills and he took the Cowboys. We made the bet at least a week before the actual game was played, because I was pretty sure my friend had forgotten about the bet by the time the game rolled around. “Sweet!” I thought. “If the Bills win I’ll ask for my dollar, and if the Cowboys win, I won’t mention it.” I couldn’t lose!

When Buffalo lost to the Cowboys, I was noticeably disappointed. My mom asked me what was wrong and I told her about my bet and how I was sad I wouldn’t get to collect on my winnings. Then she reminded me that I had to pay up because I lost. I responded:

I’m pretty sure he doesn’t remember about the bet. I’m just gonna wait for him to ask, and if he doesn’t ask then I don’t have to pay.

Remember “In Kevin We Trust”? I was welshing on a $1 bet. (Did you know the term “welshing” originated because some English bookies would move to Wales to avoid paying on bets? I didn’t either until I looked it up just now)

At least, I was planning to welsh on it before I talked to my mom. She reminded me about how I gave that boy my word and how I couldn’t be a man of integrity if I didn’t pay. She asked how I would have felt if Buffalo had won and he didn’t pay me. I cried like a sixth-grade girl who got grounded the day of a Justin Bieber concert, but deep down I knew Mom was right.

The next morning, I took a dollar out of my Tootsie Roll bank (you know you had one) and paid my friend. He had indeed forgotten about the bet and was so freaking happy when I gave him that dollar. And you know what? So was I!

I hated losing a whole dollar, but I felt so good when I paid on my bet that I’ve never forgotten that lesson. To this day, I will always pay on a bet I lose or a loan I take out.

This principle is the reason I have never gotten in over my head when gambling in Las Vegas or betting on sports games. It has guided me when I have considered taking out massive loans for purchases I knew deep down that I shouldn’t have been making.

I’ve known since I was nine years old that I need to be responsible enough with my money that I can always pay on my debts, and I truly believe it has been the foundation of my financial life.

What lessons did you learn as a child that you still carry with you to this day?

*Note: All stories this week are about why I’m not qualified to give you professional financial advice while I am qualified to make you laugh while I give my financial perspective that’s generally pretty good.