You’re not wrong.
But once you’re inside the enterprise world, it’s a different game.
If I, as a CTO, decide to self-host or use a smaller provider, I’m the hero, until the first outage. When AWS goes down, half the internet does too. That’s cover. When my own setup fails, I’m alone.
That’s the tradeoff: risk tolerance dies with scale. It’s why “nobody ever got fired for buying IBM” became a mantra. Safety becomes strategy. And when that happens, innovation suffocates.
We need cultures that stay bold as they grow.
And tools that make decentralization as easy as the cloud.
DHH, you’ve built some of that spirit into Kamal and Omarchy.
Now we need to bring that freedom to 50- and 500-person companies too.
If a CTO is self-hosting and has not set up redundancy and fail over, he may be under qualified. But 37 Signals---they are self-hosting with multiple servers in different regions. CTO 101. You don't need cloud to have redundancy.
Oct 20, 2025 · 9:21 PM UTC




