Your framing seems somehow backwards. Based on the other article[0] Nate and David bought out the business from Blue Systems. Jonathan (previously employed by Blue) proposes a co-op model, the new owners say “no thanks, we’re good”. Jonathan is surprised at this, storms out, detonating all the bridges on the way.
It’s commendable to want to start a “cooperative socialist paradise”, you can pitch it and see if there’s interest with others. But it’s totally OK as well for others to not want to join that, and go the more conventional way.
It sounds like Nate is set on starting a conventional company, and that should be fine. The previous company apparently never made financial sense so it also doesn’t work to just continue that model directly and so things and people get cut. It can be both hard to communicate and to hear, doubly so when you’re emotionally invested. That’s why IMO it’s important to separate your self worth from your job at some level, for your own mental wellbeing.
Look at almost all successful companies and they're pretty "boring" under the hood: GitHub and Stripe are Ruby on Rails, Facebook is PHP, Google is Java (still almost all new code written in 2020)... it gets the job done. Yes, they do some optimizations (HHVM etc.), but nobody is considering rewriting FB, Stripe or Google services in the language du jour.
The complexity of the infra and deployments are always relative to the size of the company, and no two companies are alike there. Small or big, it's all bespoke. Even if a few pieces are shared as open source projects, there's a veritable iceberg of complexity in the form of inhouse knowledge and tooling in each of the companies, there is nothing even close to a standard deployment system in either green field startups or FAANGs today.
I'm surprised at the 12 deployments per day, if that's truly to production. There's bugfixes etc., but feature wise Slack has been... let's say slow. Not Twitter slow, but still slow, in making any user visible changes.
In my previous company we had 20 million daily active users and we ran that on 4x M4.large EC2 instances. 4 instances not because it had any significant load (probably ~10-15% sustained), but purely because of high-availability and the ability to do a rolling release update.
[0] https://pointieststick.com/2025/03/10/personal-and-professio...