In my case, I bought my speakers first. I wound up buying Magnepan’s 1.7i, as that was the best speaker I could find within my budget at the time. I wound up replacing my preamp with a BAT VK-30SE (used obviously) and it was a significant improvement over the Emotiva XSP-1 Gen 2 I bought as a temporary preamp when my PS Audio 5.0 preamp died. After that, I sold my PS Audio S300 (also bought as a temporary solution when my Bryston 3B died) and bought a Bryston 4B SST2. Also a significant improvement over the PS Audio unit.
Going by original MSRP of the gear (I did buy mine used), my amplification to speaker ratio is aproximately 80/20, much higher than that if I had bought equivalent new amplification at today’s prices.
Other things I’ve done to the system such as improved tonearms, cartridges, phono preamp, turntable drive systems have been readily audible and the 1.7i speakers have kept up with all changes to the point that I’m really enjoying the system and not not second guessing my choice of speakers at all.