Small businesses have so much trouble with their IT support, especially if they are really small, have been around for a long time, and have owners that have just enough knowledge to know that they can do better. This was brought home to me with a nearly hour-long call with a friend of mine whom I will call Bob. Bob has four full time staff and several part timers, and has been in business for decades. We go back to the 1990s and have remained in touch, and he has called me for help on numerous times over the years.

I don’t mind being his IT support guru, and hey, I get to write this column as a result to share his pain with you. Let’s dive in.

Bob has several problems that he revealed by peeling layer by layer during our conversation. First was an aging Mac, and by aging I mean of late 2015 vintage. It is too old to run the current MacOS, a situation that I am all too painfully aware of myself. More on that in a moment. Then he needs a new printer. And what about his website? That has been down for some time, thanks to a variety of things.

And for DNS nameservers he is still using a friend from the dawn of the internet who has his own business to run — and the friend sometimes forgets that Bob’s email depends on him when he upgrades his servers, which will happen from time to time over many years. Bob is fearful about making any changes without understanding what he is doing. Oh, and by the by, his emails are getting blocked because he hasn’t set up DMARC/SPF et al. properly. And by properly, I mean he hasn’t set any of this up at all. And could his issues be due to a bad DNS entry somewhere? Perhaps.

Bob is typical of many small business people. They aren’t computer experts, even though Bob certainly knows his way around the tools mentioned above. But Bob has several things working against him:

1. As he reminded me, I once told him his problem is that he takes really good care of his gear, but then hoards it way beyond the sell-by date. I am alot like him in that regard: last year I bought a Mac Studio that replaced a ten-year old Mac Mini. But the longer out you go with your gear, the harder it is to replace it. It took me months agonizing about this decision, so long that I missed several product review opportunities because I couldn’t run modern applications. Bob just wants to get his work done, he isn’t using anything special. Just old.
2. He likes the all-in-one iMacs. I don’t: if you have to upgrade, you have to toss the whole unit out. Much better to have a separate monitor, and to have a system that you can add parts to it as needed. He does max out on memory when he buys his gear, which is a good strategy. But that 2015 vintage is time for the donation bin.
3. He has multiple suppliers for his online presence. Having one ISP as his registrar, another one for his email, another for his website, and probably a few others for bits and bobs isn’t a good situation. I have two major ISPs: one for my registrar (GoDaddy) and Pair.com for my content (email lists, website). Make that three ISPs: I also use Google Workspace for my regular email functions. See how hard it is to keep track? As for Bob, his friend from the dawn of the ‘net is now ghosting him, and he doesn’t know what to do.
4. He set a lot of this up years ago, back when things were simpler. That means his security exposure is a lot greater. Take the DMARC/SPF issue. It took me about six months and lots of help (in my case from Valimail) to get this working properly. Bob is frozen in indecision about how to even start on this particular project.
5. He likes to have vendors that he can call up on the phone and talk him through things. I do too — that got me into trouble when my ISP died from Covid. He was a one-man operation, but once he was gone there wasn’t anything there. The trick is finding a company that prides themselves on good phone support. I am happy to report that Pair does a terrific job in this regard.

Bob will eventually figure this stuff out, get the right gear, and bring his operation at least into the 2020s. But all of this takes time away from doing productive work that generates income for his business. And that is the rub that many smaller businesses have to deal with: they aren’t IT specialists, and they don’t want to be. I don’t have that excuse: I have to play an IT guy on TV, or at least on the internet, every day.