Anyone here ever start an investment club with coworkers? How’d it actually go?

A few coworkers and I have been talking about starting a small investment club and I'm curious how this usually plays out in real life.
The rough idea is.
We each put in a set amount every month (thinking around $250 each), invest it into a brokerage account, probably index funds to keep it simple. And let it grow let it for a year or two.
After that, we'd potentially pivot into real estate deals like apartments complexes once there's enough capital built up.
On paper it sounds straightforward. In reality, I know money plus group dynamics can get messy.
For anyone who's actually done this.
Did it work out long term?
What made it run smoothly?
What were the headaches you didn't expect?
Did you formalize it legally (LLC, written agreement, etc.) Or keep it simple?
Any friendship or workplace drama come out of it?
If you moved into real estate, what caught you off guard?
We're trying to think through the blind spots before we start moving money around.

Would appreciate any honest experiences, good or bad.