I got into my hobby through perseverance and penny pinching.
When I was 17 I purchased my first racing bicycle and gear ( (think $2500+). A few months went by and I was really getting into the sport. My split times on the 25km loop were getting faster and faster. Then one day my bike was stolen from the store room, which had a kryptonite lock secured to a D ring bolted to the wall..
It took me an entire year before I took the plunge and bought another racing bike (around the same price and quality). That was four years ago.
It has been an expensive and frustrating start but now I am enjoying my rides whenever I get the opportunity. I enjoy maintaining it with a level of ocd that only usually occurs at work, which also means it is going to last a while yet. I have turned down a few offers to tag along with the local group - I prefer riding by myself. Its my time, my zone and nobody can disturb me.