I'm not talking about running a family business -- that's a different topic with a whole host of its own risks and challenges -- I'm talking about buying, selling, and doing deals with pals and kinfolk.
Here are five common pitfalls:
• You lose their money: This is always the biggie. When that money goes down the drain, people tend to become a lot less philosophical. They may say "Hey, don't worry about it, I took the risk," but in all likelihood your relationship will forever be tainted -- whether subtly or dramatically -- by the experience. Family money is often said to be the easiest to get, but it can also be the most expensive.
• The business comes to the family picnic: There are people who can completely shut off work and draw a solid line across their lives when they close the office door behind them. The rest of us inevitably bring our working lives home with us in one way. When you do business with family and friends, at some point you'll be with them at an event. If there's tension brewing between you, aside from your own discomfort, it will affect those around you.
• You can't un-ring the bell: Once you remove the "arms-length" and start doing business with people who are close to you, you often start down a course that's hard to change or reverse. Changing or getting out of friends/family dealings is much harder than business-as-usual.
• There's collateral damage: I've introduced friends to my own important business contacts, only to have that introduction turn sour. We all like to think that grownups can keep clear heads about these things, but again, human nature is such that it's always easy to be calm and philosophical going in, much harder coming out. If you decide to play matchmaker, make sure it's very clear to all parties that you are simply making an introduction, the rest is completely up to them.