My first paid position as a software developer was for a small, dot-com startup in Windsor, ON Canada. We co-located in Detroit - which meant border crossings (though this was pre-911 so crossing as a Canadian citizen was easier) - and had just a couple of servers on a rack. We were software engineers and had people who knew what they were doing. So yeah we were technically proficient. But I'm not sure I'd call that company among "the most technically sophisticated of organizations". We were tiny. In fact, when I first started working there, we were working out of a house with a workforce of like 25 people max.

When that company went under during the dot-com crash, I started my first business shortly after. It was 2003, I was 21 years-old and this business allowed me to work from home and feed my family until I re-entered the job market in 2018. For 15 years, I was a one-person organization, and because my business operated "free" adult-entertainment websites, bandwidth was my most significant expense. For that reason, even when Cloud became a thing (which it wasn't in 2003), I never migrated because of the bandwidth costs alone. Cloudflare was a major game changer but even it didn't exist when I first started out. There were CDNs like Akamai but they were crazy expensive and out of my league. So at its peak, I had about 12 bare metal servers around the world (all rented from the same hosting company - original called Server Matrix it then became Softlayer and then was bought by IBM and went to shit and is now IBM Cloud). I admin'd those on top of writing and maintaining all of the code and running the business independently with occasional help from my wife.

I am obviously very technically competent. I'm a Principal Software Engineer today. But technically sophisticated? There wasn't much sophistication about it. I did bare metal servers because it was the only cost-effective way to run my business. It was attainable and it worked. And it worked in a way that Cloud couldn't when Cloud came on the scene - so I never went Cloud with that operation just due to cost alone.