You know when they say never lend your friends or family money. I will add that you also shouldn't invest in your friend's or relative's business, unless you are 100%ready to lose your money.

I invested in a friend's business. Turns out the fact that he hasn't worked a job in his life makes him woefully unprepared to start a business. I thought I was a 100% ready to lose the money, but seeing him make one stupid mistake after another did not sit well me. Even after I gave him so much advice, which he totally ignored, and wouldn't admit he was wrong. I even gave him a loan in the hopes that things would work out, which they didn't obviously. So many stupid decisions.

We eventually brought in a managment company to take over things, but that's not what ended our friendship.

I was going through a rough patch a while ago, so I was asking some friends I had lent money to if they could pay. I knew my friends were also going through rough times, which is why I was only asking, and didn't pressure any one of them. In fact, I actually ended up not getting any money back from these friends.

Once he found out I was asking for money he wouldn't take my calls and ignored me for the last year and a half.

He has contacted me recently, after the long absence. Incidentally, we're renegotiating the contract with the management company right now. It turns out he wanted to add some changes and wants me to back him with the other partners.

So yeah, I lost my best friend. I try to tell myself that it's a learning experience, but it's not fun learning that people you trust completely can sometimes turn out unreliable.