Here's $40K for your business, Bob.
So. Pros and cons? Okay, maybe the answers are a bit obvious.

Pro: They return the money promptly and say they owe you one.

Con: They return the money late, or never return it at all. Trust is lost, “friendship” is broken, silence ensue, follow by hate and bitterness…

Letting people borrow money is an iffy issue. Especially if it involves family members, because unfortunately sometimes family members are the ones most likely to take advantage of you. Thankfully I don’t have family members like that, but I’ve read/heard plenty of stories.

Thinking back, high school was a period of time where people were constantly asking to borrow money from their “friends.” They can be small amounts, but they certainly add up. One particular person from back in high school still owes me $60 till today. Not a large amount really, but it still tickles my bone in a wrong way whenever I think about it.

I’ve borrowed money occasionally too, but mostly because I just don’t have cash on me. To my recollection I’ve paid everyone back ( but I’m not perfect so I probably owe a buck here or there). These days it’s not really an issue, as I haven’t let anyone borrow any money — not because I don’t want to, but because no one asked. Although I think I’ve learned my lesson, and can distinguish between those that are trustworthy and those that aren’t.

Which reminds me of something I read before on an online message board. There are two types of borrowers: Those that can pay you back but wont, and those that want to pay you back but can’t.