This really is a GREAT thread. Interesting to see how folks got started.
I got started in the early 70's. I had horses, and being a young adult with no money, I started hanging around an old saddle shop. The old gent who owned the place told me if I was going to continue being there, he was gonna put me to work. Started with hand stitching, which moved to simple tack repairs, which moved into saddle repairs. When he passed on, and the shop sold off, I concentrated on my horses and showing. Sure was nice to be able to fix my gear..and word got around the show circuit that I could. As you can imagine, I started getting repair commisions from folks in my area. This turned into a nice "drop off/pickup" arrangement with a local tack shop.
I was still showing my horses, but, being vertically challenged (lol) I could never find chaps that would fit me. I picked up a pattern, made some modifications to that, and put a set together. They were pretty rough looking, but got the job done. I made another pair later with some improvements, which then turned into "those are really nice, can you make me a set?" I have been making custom chaps ever since.
Over the years, I was forced to move back to Illinois for family reasons. This was the first time in 20 year I was without any horses, so I bought a motorcycle to ride instead. Last year, like so many others, I lost my full-time employment. This left me with too much time to ride my bike (which is now a trike). On a charity motorcycle run, I was approached by a gentleman asking where I got the chaps I was wearing. They happend to be a much improved set I had made during my horse days. When I told him I had made them, he asked to take a closer look, so I pulled them off so he could inspect them. He was so impressed with the hand-tooled yokes and quality that he asked me to run the custom shop in a new biker leather store he was opening.
These days, I am still making chaps, just for Iron Pony riders. The fun part is I get to bring a bit of western influence into the biker world. I offer hand tooled yokes/cuffs, belt inlays, western conchos, and buckle, tip, and keeper sets. You should see these guys go nuts over this stuff...LOL
The great part is, I now get to work every day doing something I love, leatherwork. I just have to grin and bear it when I get teased about the country music playing on my shop radio....
If you happen to be in No. Illinois and would like to check out the shop, send me a pm and I will be happy to give you info on the shop location.