Why Friends Should Rarely Do Businesses Together

Why Friends Should Rarely Do Businesses Together


I once saw this Everybody Loves Raymond episode on why it’s dangerous to do business with friends.

The episode goes like this…


Ray is the main character of the show.

One day, his oven broke.


Normally when something breaks, he asks his dad to fix it.

But as of late, his dad hasn’t been able to fix things.


Ray’s wife, Debra, ends up asking Ray’s friend, Gianni, to fix the oven.


Initially, Gianni is sweet talking away.

Talking about how he’s a licensed contractor and how he will fix the oven in no time.


Debra is excited!


Once Gianni is hired, the tune changes.

Rather than being a sharp contractor, Gianni turns out to be a lazy schmuck.


He brings a TV with him to work.


Cracks crass jokes.



Debra slowly loses patience.

She tells Ray that Gianni is no good.


Now Ray is caught in a weird predicament.

His wife wants to fire the contractor, but the contractor is his best friend.


Rather than fire Gianna, Ray decides to motivate him to the finish line.

‘Come on, Gianni! We are almost done.’


A few days pass by, and the new oven is finally here.

All Gianni has to do is install it, collect his paycheck, and life is good.


But as Gianni tries to put the new oven where the old oven was….

There is a problem.


The new oven doesn’t fit.


Gianni didn’t do the correct measurements.

He says he will get the correct-sized oven in a few weeks.


At this point, Debra is a volcano that is ready to erupt!!

Even Ray decides to throw in the towel.

He tells Gianni:

‘Just put the old oven back.’


Ray thinks that’s the end of it.


Not quite.


Gianni hands Ray the final bill.

2000 dollars.

The initial quote was 1500.


Ray says:

‘What the heck?? You’re charging me 500 extra dollars and I don’t even get a new oven???’


Ray confronts Gianni for his professionalism.

Gianni calls out Ray for trying to be a cheapskate.

They go back and forth.


Ray tears up the bill.

When he does that, Gianni says:

‘Don’t ever call me for anything again!’


The shredded bill symbolized that the friendship was over.


Luckily, this was a TV show.

At the end, Gianni apologized for his behavior and Ray did the same.


But in real life, a lot of friendships end because of business.

2 friends decided to go to business together and it didn’t go as planned.


Every now and then, going into business with a friend is fine.

You 2 complement each other like peanut butter & jelly.


Just know what you’re getting yourself into.

  • Have hard boundaries.


If they are your friend, then it’s not a problem to say:

‘If I’m going to give you money, I expect the project to be on point.’


It’s good to even admit:

‘Me as a friend is all fine and dandy. However, I’m a pain in the ass to work with. I like to be on time, and I’ll call you out if you’re not on time.’


You could say this with a smirk.

But the smirk is accompanied by fiery eyes which imply:

‘Don’t let the laughing fool you, I’m serious.’


Adding in the variable of money is tricky when it comes to friendships.


Personally, I don’t like to do business with friends unless it’s something small like getting a haircut.

If they mess up, my hair will grow back.

I won’t resent them.


Other things take a while to grow back.

And each second it doesn’t grow back, each second there is a dark cloud looming over the friendship.


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