You’ve invited someone to lunch and then asked them to pay for it.

You might be a shame-faced entrepreneur if…you’ve invited someone to lunch and then asked them to pay for it.

Geez, this is so embarrassing I think I’m repressing the memory and forgetting the details of how it all came about. Kids, don’t do this. I mean, it’s one thing if you forget your wallet, but we actually planned this one out. My only defense is that I was only an accomplice to the crime, although that doesn’t absolve me from responsibility for being weak and spineless and going along with the plot.

The target? Brandt Andersen, former CEO of uSight, now real estate mogul and owner of an NBA development league? Geez, Brandt’s all over the place these days, which only makes this all the more embarrassing.

The year, 2000, or thereabouts.

The location. Olive Garden.

So my partner and I were college students, as was Brandt, but Brandt had experienced quite a bit more success than we had. We wanted to see if there was any chance of forming a partnership and so we invited him to lunch. Now at this point I really don’t know what happened. I don’t know if we just happened to not have any money in our bank account that day, or our credit card was maxed out, or what, but I find it difficult to believe we couldn’t have paid for lunch somehow. But if I remember correctly my partner was really against the idea of paying for it because we were hard up for cash.

So we pre-meditated a plan to go to lunch, and then tell Brandt we were too poor to pay for lunch, and would he take care of it? Argh…it’s too painful to even think about. What were we thinking? Talk about no class. And somehow we did it. Brandt was all class. He took it all in stride and acted like it was no big deal, and he’s even been a gentleman to me since, but man, it still pains me whenever I think about it. I’m not so much embarrassed in the presence of Brandt as I am in general because I feel like this was more a crime against humanity than Brandt himself.

Anyway, being a cash-strapped entrepreneur can lead to strange things. If anyone ever tells you money, or the lack thereof, doesn’t change people’s behavior, think again. I’ve tried make up for my sin by always offering to pay for lunch, even when someone else invites me to lunch, but the guilt remains. Maybe I need to go through one of those life experiences where I live an utterly degraded life of self-loathing and bitterness, only to be rehabilitated and redeemed years later by a group of master ninjas, after which I return to Utah to fight crime and teach business etiquette lessons.