My dad is a serial entrepreneur. When I was young, he owned an excavating company, then a commercial roofing company, then he started a concession business, then another excavating business. When you're family's in those businesses, you learn to fix things, so that you can put some dinner on the table. We always had good looking equipment, because Dad would let me "practice" paint and bodywork on the commercial vehicles. As long as they are the same color, with similar logos, you'd be impressed how good old equipment can look, but I digress.
Growing up, Dad had some very good tools, and a lot of "improvising" to make do. Poor is as poor does, I guess. When Dad sold the excavating business (at the peak of the housing boom), he sold everything, including all of his tools, all of his equipment, etc. It was a great move, and a luxury many small business owners never get to see. It's not often that businesses like this aren't either handed down, or auctioned off.
Like I said, my Dad is a serial entrepreneur, so he now owns a trucking company. Go figure.
So, back to when I started collecting tools. I think I was probably 13 and I decided that I needed to start getting some of my own tools, so I asked for them for Christmas/Birthdays, etc. I tool an interest in bodywork, so I started buying bodywork tools, as well as paint guns, airbrushes, etc... I still have most if not all of those tools to this day.
I traded labor and things like that for tools, as well. There was always someone coming by the shop looking for money, wanting to sell a car or a mower or tools, etc. So I guess I became a bit of a horse trader. I painted my grandmother's house for my grandpa's old craftsman top chest. I figure I've only got a couple thousand in labor in that thing. But I was able to pass it on to my sons, so that's a cool thing.
I've always enjoyed fixing my own things, so I guess I justify it that way.
For my current "collection" I started when I got a "real" job out of college, and I built things "one bonus" at a time. I was brought up learning to make do, so I never really got in a hurry about building my collection. Slow and steady as they say.
I knew I wanted to build a house someday, and I knew that I would want to do the woodworking for it, so I started buying quality woodworking tools to build my collection. One at a time, usually one a year, until I had what I needed to get started milling flooring and trim.
I've started doing the same thing with my metalworking tools. I got a decent air compressor, then a sandblast cabinet, then a sandblast pot, then a cut-off saw. I still need to get a torch and a welder, but like I say, steady does it.
Recently, I've started filling the gaps in my "basic hand tool" collection by buying the missing wrenches/ratchets/etc. I travel quite a bit, so I scour the pawn shops, craigslists, etc.
Some how, since I started coming to GJ, I've gone from 3 ratchets to 15. The obsession is starting, I think.
... my mom and dad for the $99 STACK on from kmart (i was 8 afterall) and a plastic Snap On emblem from my uncle (i didnt know the difference) and i got my first toolbox 
