As we all know, IT is not a priority for many execs. As the thinking goes, why spend money when the current technology is working fine -- if it ain't broke, don't fix it, right? But a small company can ride this mentality to an extreme.
A few years ago, I did some consulting work for a customer who put IT at the bottom of the list. This was a small company with no IT staff; instead, one of the employees knew a fair amount of computing and stepped in when needed. The owner saw no reason to make upgrades. His policy was to spend the bare minimum on repairs and to work the hardware and software until they broke.
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I understand making the most of your assets, especially in a bad economy, but sometimes you need to invest in IT to avoid spending even more later. As a contractor, I didn't like to intrude, but I mentioned to the owner the benefits of up-to-date technology. He insisted nothing needed to be changed -- everything was fine. He also cautioned me to fix only what was called for and nothing more because he wasn't wasting good money on my shenanigans.
At the beginning, I was called in for hardware problems. This customer had Pentium III-based servers in production that still worked fairly well. I helped replace failed hard drives (and clear out dust). I also tracked down used units on eBay because it was getting harder and harder to find parallel SCSI hard drives.
In addition, I fixed a couple of hot-swappable, redundant power supplies. The server manufacturer no longer made them, and I wasn't able to find any used ones online. I ended up ordering parts from my favorite online electronic parts store and then doing component-level repair to fix those power supplies.
I tried laying out the situation in practical terms to the owner, explaining how one of the dangers in having such old hardware is that it becomes harder and harder to find replacement parts. Even for component-level repair, it gets to a point where the labor cost for the repair is more than what the old hardware is worth. Furthermore, technology changes -- CPUs have moved from 32-bit to 64-bit, for example. He waved me away, saying again it worked fine and there was no need to upgrade.