Tax Evasion, Trust Funds and Video Rentals

The job: 55th Street Video – cashier

My age: 14?

Hourly Wage: $4.50 – cash

55th street video – the local video store, just a few minute walk from my house. It was one of my earliest jobs and really wasn’t the most taxing job at all.

I think I somehow got this job because I was always in there renting videos, and I struck up a conversation with the owner, and he offered me a job.

This is a good reminder to all that if you can strike up a conversation with any owner of a business you are interviewing whether you think you are or not – always know the hiring managers. My neighbor Brian always somehow meets the owners of most stores he goes into and usually gets a deal along the way. Talk to the owners! Be like Brian!

Back to the story:

I liked to rent videos.


I liked movies.


It seemed natural to work at a video store.

But, this video store was unique a few ways –

The owner was required to run a business in order to receive his montly inheritance from a deceased parent.

You read that right, this guy had to run a business in order to receive a check in the mail each month.

So what? His parent decided the best way to incentivize this guy was to force him to run a business. Seems somewhat micro-managy from the grave. What this led to was an owner who really didn’t care and just had the video store for no other reason than to make sure he was getting his inheritance.


How I found all this out at 14 is beyond me, but another life lesson is to talk with people, ask questions, and shut up. People love to talk and spill secrets. If they see you as trustworthy, they will tell you more. When you find out things, keep them to yourself, and you will out more things than you would believe.

Each time I worked a shift at the video store I had to run the cash register, help people with movie selections, and sometimes charge people if they had not rewound their video tapes.


A young me had no concept that someday all video stores would be extinct and I could watch any movie in the history of mankind all from home without going to a video store. That fact still blows my mind.

I do miss Friday nights when my now wife and I would head to the video store in south Minneapolis where we lived and spend 45 minutes debating which movie we would watch. Inevitably this would also be followed with picking up takeout food from a few places near the video store – it made for quite the night. I also really enjoyed when the staff at the video store would make recommendations – all of that has now been replaced by the algorithm – I miss the local video store employees recommendations for sure.

Back to 55th street video.

The owner did take good care of us employees. I think he paid us cash, from the cash register, and now I understand that while I made more money, we were both probably committing tax evasion? Things you don’t know when you are 14 – if someone pays you cash, Uncle Sam is not getting his cut. Maybe this is something for DOGE to take on? 😊

The owner also pulled money from the till and bought us pizza during shifts – this was a big perk. I’m not sure why we had two people working at a time at the store, but it was fun to eat pizza with co-workers – and growing up in Chicago, good pizza was always nearby.

This job taught me a number of things including how to make movie recommendations to people wandering the aisles of a forlon video store.


It also taught me more about working with numbers, listening to people and giving advice and a lot about customer service.

If you can work in retail and deal with customers, it will serve you well for your whole career. AI bots still aren’t that great at dealing with customer issues. Have you tried resolving something with an airline chat bot? Get me to the human as quickly as possible.

If you can deal with sticky customer situations, you will always have value in organizations. The ability to hear and understand issues, be empathetic and find resolutions to problems? This will never go out of style and is always needed. Customer retention is the true multiplier in any business. Finding new customers is super hard, the last thing you want to do is lose them.

The owner of the store often came in and took cash from the register – again making me wonder if he was up to some more illicit activity than just tax evasion – but I’ll never know.


55th street video eventually went out of business and I think the owner sold the strip mall it was located in as a real estate transaction.


I’m not even sure how long I lasted at this job, but it was fun while it lasted.


Did you ever work at a video store? If not, do you have memory of going to the video store to get movies?

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