Congrats! Being able to run a nice company bootstrapped seems amazing.
Turning 10, you might want to stop ditching WordPress for being 15 on your homepage though ;)
Your customers demand blazing-fast digital products, web standards are evolving at the speed of light, yet you rely on 15-years-old solutions like WordPress that force you to deliver heavy, low-quality user experiences.
I like the house analogy, but I like to think of it as if the people building the house did not know how it was supposed to look (or function). This is mostly true, since very few developers know exactly how the end result (product/service) should look and function when the start coding.
e.g. "We did not know where to put the piping at the start, so we put it on the outside and now installing a new restroom is sort of tricky."
> I'm currently building a skyscraper on the foundations of a bikeshed.
Not sure if you are joking or not, but I often hear similar things and I believe that it misses the point. What constitutes a good foundation in software is very subjective - and just saying "foundation bad" does not help a non-technical person understand _why_ it is bad.
It's better to point at that one small rock (some ancient perl-script that no-one longer understands) which holds up the entire thing. Which might be fine until someone needs to move that rock. Or something surrounding it.
Turning 10, you might want to stop ditching WordPress for being 15 on your homepage though ;)
After all, you'll be there in only 5 years!