Jonathan Blow is a good speaker – I haven't seen this talk (will watch later) but I'm sure the content is good.
However, he has also not worked in a tech company of the kinds we see today (games are a different business), and he hugely underestimates the necessary complexity of systems. He is right that there's a lot of unnecessary complexity, and that we should push back on complexity of all kinds, but I've always found his opinions around this to be naive, to lack nuance, and to lack experience. His arguments often boil down to criticising progress rather than acknowledging the issues progress brings and finding ways to work around or minimise those issues.
Getting to five 9s is hard, and as software does more it'll get harder, but it's not impossible, particularly if we look at five-9s from the user's perspective, as clients get smarter we have more leeway to accept minor downtime without harming the user experience.