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The Gambler Story

Updated: Feb 11, 2021

There was a gambler who taught me the most ingenious vehicle service contract (VSC) selling process for cash customers.

A few days ago, I was talking with an unusual couple. The wife was this stunning business woman. She looked like Angelina Jolie in a custom perfectly fitted business suit. She wore these large red eyeglasses. She had handed me her business card which described her as the Chief Actuary for a major insurance company. Her job was to calculate all of the risks that the insurance company would underwrite. She was a wizard at math and figures. She literally calculated her sales tax in her head without a calculator. I was in awe of her. She had this incredible mind while being wickedly attractive.

Her husband was very different. He was a rugged good-looking cowboy type. He wore blues jeans and a flannel shirt. He also had glasses. But his were sun glasses. He was wearing sunglasses in my office! It was odd because I never knew whether he was looking at me or not.

When it came time to present the menu options, I started going through my normal presentation process. The woman seemed disinterested. But the husband slowly raised his sunglasses to his head. He seemed strangely intent and even picked up a pen and jotted down a few notes as I explained the risks and benefits of the products.

When I finished, I asked them if they had any questions and asked which option would work best for them. Almost immediately, the wife said, “We will take the base principal and interest option. Thank you for your explanation of our possible options, but we will stick with just the principal and interest payment.”

“Not a problem. These are just options. You can take some of them, all of them or none of them. They are just options. If you will sign this short waiver saying that I have presented you the available options and you have chosen to decline them, I will move on with the rest of the paperwork.”

“I need to have both of you sign the waiver if you don’t mind.”

I noticed that the husband was thinking about something. I slid the waiver over to the husband to have him sign first. He seemed distracted and I wasn’t sure if perhaps he was having second thoughts about the declination.

“Before we sign this waiver, I do have a question. You mentioned in your presentation that the VSC was for 10 years and could be cancelled or transferred at any time, correct?”


“How does the cancellation work? Is there a refund of part of the premium?”

“Yes, the 3000 premium is divided by the number of months, in this case 120, and the policy earns $25 each month. If you keep the policy for 1 month and then cancel, the policy earns $25 and the cancellation amount would be 3000 less the $25. There is also a cancellation fee of $50.

“So, the policy earns $300 a year. If we keep the car 5 years, we would get half of our premium back, correct?”


“If I would sell the car to a friend or neighbor or co-worker, they would get the remaining coverage?”


“Is that true for the other products as well”


He leaned over to his wife and whispered something into her ear. Her eyebrows raised and then she smiled. She looked at me and said, “We will take the Best Seller Package”.

I was stunned. Seconds ago, she was disinterested and almost dismissive during the presentation. Her brilliant mind seemed to conclude that the products were not worth the money. I was intimidated by her title, her brains and her wicked good looks. My mind had already conjured up a vision of her telling me that as the chief actuary, she had looked at the pricing and calculated that she would be better off simply paying for any repairs when they happened. I was terrified of her dismissing my arguments and making me feel miserable about myself. My instinct was simply to run the paperwork and not have a confrontation with this impressive woman.

But now I had to know. What did he whisper in her ear that made her raise her eyebrows and then break into a big smile? What did he say?

“I am happy to get the paperwork done. I think you guys have made a great choice. But I am curious. Your wife seemed so dead set against the products and when you whispered into her ear, she seemed excited and happy to have them. What did you say?”

The husband smiled with a broad grin. He lowered his sunglasses. I could no longer see his eyes. “You never asked what I did for a living.”

“What do you do?”

“I am a professional gambler.” He looked at me and smiled. “Do you want to know what I asked?”

“I am dying to know what you asked.”

“How valuable would it be for you to have a question so powerful that you change a brilliant actuary’s decision with that single question?”

“It would be super valuable.”

“How many more sales would you get each month if you had the ability to ask that question at just the right time?”

“Well, I would definitely sell a lot more of my cash buyers and a significant number of my finance buyers that currently are giving me a hard no at the beginning of my presentation.”

“So, would you sell at least ten more service contracts each month?”


That would be a good thing, right? You are paid a commission on everything you sell, correct?


“I will make a deal with you. I will give you the question. But you need to know that my wife is a numbers genius. She can do math in her head like a supercomputer. For her, she can easily see how the math works.

However, you will have to do some work to allow most of your customers to visually see the math. They won’t get it, unless you visually demonstrate the numbers. Are you following me?’


“Good. Write me a check for $1000 from your personal checking account. I won’t cash the check for 90 days. You commit to demonstrating the math to your customers and I will agree to only cash the check if in 90 days, you make a lot more commission and the $1000 is one of the smartest investments you have ever made. Deal?”

I was taken aback. I didn’t want to write a check for a $1000, but I did want to know what he had said. I started to have doubts that the question would actually work for me. But, he had given me an ironclad guarantee. If it didn’t work, he wouldn’t cash the check.

I have a question for you. You are a professional gambler, right?


“How much did you make last year on gambling.”

Then his wife leaned forward and winked at me. “He reported $763,846.27 in winnings last year.”

“Here’s my check.”

To discover the question that the gambler asked his beautiful and brilliant wife, email:

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