The Vending Machine Hustle

The Professor made his living “losing money” in vending machines.

Phil Autelitano
The Hustle

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I once had the pleasure of meeting a man we’ll call, “The Professor.” He was an older chap, with white hair and a white beard. He wore a tweed jacket and smoked a pipe and drove an older, but classy, Mercedes. He literally looked like he taught philosophy at Yale or something, thus the nickname.

The first time I saw him, was at a laundromat in Upstate New York. He had just lost his $2.50 in the super big-load washer and the attendant was making good on it. I thought nothing of it at the time.

About an hour later though, I ran into him again at the local pizza place. Ironically, he had lost $3.50 in the cigarette machine, and the owner was giving him a bunch of quarters. Interesting… was it just a stroke of bad luck?

As I ate my pizza, I watched him walk across the street to a gas station where it appears he lost some money in the soda machine, and was getting a dollar back from the clerk. From there, he made his way through a shopping plaza where I’m sure he “lost” more money wherever he found an opportunity to do so.

I was on to his racket. Not bad.

A few hours later, I got to my local hang-out, a 24-hour diner, where I happened to run into him again! This time he was having dinner. I sat in the booth across from him and after it looked like he was done eating, I struck up a conversation.

After I told him I had seen what he’d done, he wasn’t shy about telling me more. They never are.

He told me how he had been married for 30 years and lost his wife to cancer. They had planned to travel everywhere but she died before they got the chance. So now he was making good on it, travelling to all those places they wanted to go — New York, Miami, Nashville, Chicago, L.A., San Fran, and so on — and financing the entire trip by simply “losing” his money everywhere he went. Soda machines, snack machines, newspaper machines, washers, dryers, car washes — wherever he could lose money, he “lost” it.

“Drive down any Main Street in the U.S.A., and you’ll find hundreds of opportunities to “lose” your money,” he told me.

Not a bad gig, very little risk — who’s going to question this respectable-looking old guy when he says he lost two bits in your machine?

The Professor “lost” on average, $100 to $150 a day. Not a fortune, but certainly not chump change, especially for a guy pushing 70 on Social Security.

Not all of the money came in the form of cash though. Some places had to send him a refund in the mail, and other places would simply give him whatever it was he was supposedly trying to buy — i.e., a pack of cigarettes from the machine, a soda, etc. So in addition to pockets full of change, he always had a trunk full of stuff to sell.

I went ahead and bought five packs of smokes off him for $10. Two bucks a pack — a steal at that time. Before I left the diner I sold them for $12 and paid for my coffee, plus tip.

So there you have it, The Professor traveled the country, from city to city, “losing” money everywhere he went. It paid for his dinners, his hotels, his gas, and whatever was left he put away for a rainy day.

Again, who would question this guy? No one. It was the ultimate con. No one got “hurt” bad. He could have probably panhandled that much a day, but at least he was being creative.

“If you believe me, then I won it fair and square,” he told me.

I’d heard that before. It’s like the con man’s credo.

Sure it was a grind, but he didn’t have anything better to do. He was alone. And he was on a mission to visit all those places him and his wife dreamed about. She would have wanted him to do that. Apparently Social Security wasn’t enough to pay for it, so he found another way.

I often wonder if he’s still out there doing it or if he finally visited everywhere and has since joined his wife. I’d love to know how much he made “losing” his money all those years. I imagine it adds up significantly.

Next time someone comes into your place of business telling you they lost their money in your vending machine, remember The Professor.

— P.

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Phil Autelitano
The Hustle

a/k/a Phil Italiano, Publisher, Screw Magazine | www.screw.wtf | @PhilAutelitano