H and I aren't really affected by this since we don't offer a service that our friends need.
We do have friends that are in businesses that offer things that we'd need...for example, one friend works at a car dealership that we'd be interested in buying from. A few of my friends are also photographers, others sell from home businesses, and some do landscaping related services.
So far we've had pretty good luck with mixing business with our friendships--but we haven't really done it that much. I'm afraid that one of these times we might not be happy with the work they've done or feel like we're getting the run around money wise, and it will bite the friendship in the ass.
Do you do business with friends, or do you go elsewhere? Has it ever gone badly?
Re: Doing business with friends
One of my "good" friends (she's not really that good of a friend but she considers us bff's because we've known each other forever) is a hairstylist and has done my hair since college, so I've done business with her for years. That, however, has somewhat bitten me in the a$$ recently. I decided for various reasons it was time to move on and my cousin is a hairstylist now so I had her do my hair last time and I LOVE it--her shop is also much more peaceful and drama free than my friend's so it was all around a better experience. Telling my friend I went somewhere else sucked but, I had my reasons.
I'm careful who I choose to do business with. The only REALLY big thing was our realtor when we bought our house--he was an old college friend of mine (who I hadn't talked to in years). But I knew he was a trustworthy person and had been a great person in college (he fixed my laptop freshman year for the cost of a 2-liter of Dr. Pepper), and I had an inkling he would do a good job for me. Since home buying is a big thing and there are some crap realtors out there, I felt better going with him. And I'm glad I did--he turned out to be a great decision.
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I'm admittedly a little worried about one business exchange in particular--the vehicle situation. H is going to need a new truck within the next year, and he of course wants the same make that he has now. Our friend is pretty high up in the dealership--and he and his wife have made it clear they're going to want our business if H goes with the same type of truck. If things were to go badly, it would ruin the friendship. If we don't use them at all, it will ruin the friendship/make things awkward for us. Kind of screwed either way, really. I'm sort of crossing our fingers that H will switch to wanting a different type of truck so we won't have to worry about any of it.
I think you always have to use your best judgement and if you guys are good friends everyone should understand that. We try to do business with friends (but not so much family) because we appreciate the same from friends. The old saying "treat others as you wish to be treated" rings loud in my ears.
My husband owns a business and he does business with a few friends and it is honestly something we weigh individually with each friend. We kind of go down the list of everyone we think would ever be interested. If we think it could go "bad" in any way we really think about taking on the job.
I also work for myself now and I always feel like I need to put myself out there while at the same time not putting too much pressure on anyone to use me. I am working on a deal with a friend right now, whom I have known for seriously my entire life... I just have so much anxiety to get her exactly what she wants and nothing less. Love her to death and want no negative effects on our friendship.