Why entrepreneurs have much to learn from little old ladies

Have you ever been done over by a clever little old lady? This bank president had … and the lesson he learned was that entrepreneurial skills are not merely the domain of young, thrusting Type A people.

It took the wit and deviousness of this elderly lady to bring two very senior professionals down to size in this allegedly (hmmm) true story…

joke about balls

I’ll bet you $25,000 that your b*lls are square.

How to outwit your opposition

A few decades ago a little old lady went into her very large Chicago branch of the Bank of America one day, carrying a bag of money. She insisted that she must speak with the president of the bank to open a savings account because, of course, yes, it’s a lot of money.

After much hemming and hawing, the bank staff finally ushered her into the president’s office.  The bank president then asked her how much she would like to deposit. She replied, “$165,000” and dumped the cash out of her bag onto his desk.

The president of course was intrigued by how she came by all this cash, so he asked her, “Ma’am, I’m surprised you’re carrying so much cash around. Where did you get this money?”

The old lady replied, “I make bets.”

The president then asked, “Bets? What kind of bets?”

The old woman  said, “Well, for example,  I’ll bet you $25,000 that your b*lls are square.”

“Ha!” laughed the president, “That’s a stupid bet. You can never win that kind of bet!”

why banks shouldn't take on old ladies

The old lady challenged, “So, would you like to take my bet?”

“Sure,” said the president, I’ll bet $25,000 that my b*lls are not square!”

The little old lady then said, “Okay, but since there is a lot of money involved, may I bring my lawyer with me tomorrow morning at 10:00, as a witness?”

“Sure!” replied the confident president.

That night, the Bank of America president got very nervous about the bet and spent a long time in front of a mirror checking his b*lls, turning from side to side, again and again. He asked his wife to thoroughly examine them, too, until they were both absolutely positive that in no way were his b*lls square and so, he would win the bet.

The next morning, at precisely 10:00 am, the little old lady appeared with her lawyer at the president’s office. She introduced the lawyer to the president and repeated the bet: “$25,000 says the president’s balls are square.”

The president agreed and confirmed the bet again and the old lady asked him to drop his pants so they could all see. The president obliged. The little old lady peered closely at his b*lls and then asked if she could feel them.

“Well, OK,” said the president, “$25,000 is a lot of money, so I guess you should be absolutely sure.” Just then, he noticed that old lady’s lawyer was banging his head against the wall. The president asked the old lady, “What the hell’s the matter with your lawyer?”

“Nothing, she replied, “except I bet him $100,000 that at 10:02 this morning, I’d have the President of the Chicago State Street Bank of America’s b*lls in my hand.”

Dontchya love clever seniors?

What funny stories about seniors can you share?




  1. Well, I will never trust a little old lady again!

  2. Trudy Van Buskirk says

    RFLOL!!!!!! I’ve seen this one before and it always makes me laugh 🙂