Did any of you lose money on your first flip/investment?

[Bill Thompson]

My fiance and I are new to real estate investing and she is the primary in this venture.  She's a Corporate Financial Manager making good money and I am an IT Project Manager making pretty good money, but she is feeling a little disillusioned with her career and says she's always wanted to flip houses.  As such, we went to a "guru" seminar which was a waste of time (Nick Vertucci... got our money back) and are now trying to read everything we can and are talking to others for advice.  

This is more her thing than mine and I'm still on the fence.   I support her, but am just not sure how much I want to be involved yet or put my savings at risk.  I've read testimonials of success stories, but haven't really heard from anyone who's lost money, particularly on their first venture.  I'm not trying to dwell on the negative, but rather would like to get a more realistic picture of how much of a financial risk this is, as we'll likely be using much of our/her own funds.  I don't expect to have huge success out of the gate, but don't want to lose our collective shirts either.

What has been your experience when starting out?

Thanks so much in advance.