That was definitely the weirdest point of that post. Even if you agree with "hire generalists over specialists", hiring generalists to build a custom S3 sounds like a terrible idea.
Hot take from someone with a decent amount of experience in this area, but half way across the world: Everything in this article is a terrible idea that only works when you're drowning in investor money.
If you try and apply articles like this outside of SV, you're going to be miserable.
The only point in this article I can't completely refute with my own experience is the one about funnel discipline, and really that one just boils down to "write stuff down" (still good advice, but hardly needs to be said).
Bad code spreads like cancer. 2-3 months is more than enough time to do serious damage. "Comfort in the false negative zone" is EXACTLY what you should be doing as a startup, your first bad hire will ruin you.
Even the framing at the start of the article (first 10-20 engineers) is wrong. The point of a startup is to create an environment where your devs can literally 20-100x the average dev at a big corp (10x is honestly too conservative with the rubbish I see in my day job). Each hire in that environment gets exponentially more difficult if you're doing it right. I think realistically the startup phase probably tops out at 5-10 devs, but it depends heavily on how many 'large modules' you can split your business up into. If you're operating more like 5 startups working together then maybe you can get into the 10s and 20s.
If you're hiring 10-20 devs to work on a single product, you're in no man's land. That's the point where you want to start converting to a business that relies on 1xers. To do that you need to scale up, and you can't do that unless you're already successful or you have boatloads of investor capital.
What these bozos call a "startup" in Silicon Valley is actually just medium/big business dev that doesn't make any money yet. You're welcome to try that approach if you have the investment to make it work, but as someone that's consulted for a bunch of companies doing exactly that and seen all of them spiraling rapidly down the drain, I'd advise against it.
This exact approach is why "99% of startups fail", it's just rolling a dice to try and skip the whole "building a sustainable business" phase and go straight to "billion dollar enterprise". That's totally fine if you understand exactly what's happening and what the trade off is. Not so fine if you don't understand and you're just following along with articles like this make it seem like generic good advice for all startups.
