When I first got back into bikes and started riding fixed, I bought basic tools to maintain my own bike. Then I got a job at a shop and started buying a lot of bigger stuff (headset press, truing stand, etc) at cost over the span of a couple of years. Once Retrogression opened, one of the smaller distributors we work with offered me great 'new shop' discount program for buying tools and supplies so I dropped some pretty serious coin on tools I never would have needed if I weren't a shop owner (along with some I don't even really need now).