I think there are a few things that explain the phenomena:
1. You're asking rich and powerful people to give up control. Everyone hates giving up control, but my experience is that people accustomed to control hate it more.
2. It's not familiar, which means it feels risky.
3. It objectively lowers total payout in the best and worst case scenarios for power, and it's not actually clear the E(V) for the capital class goes up. It might, but no one knows apriori, and it's expensive to test.
This mix of low information, a small number of potential actors, and feelings of anxiety around uncertainty and loss of control is a pretty potent mix for inefficiencies like this to persist IMO.
If an employee #1 share grant isn’t for you (as it isn’t for me), there are plenty of other capable engineers out there who are willing to take a lower stake for a variety of reasons.
I don't think this is an accurate representation of my views. I'm happy to take more in the 2-3x range so long as I'm protected from the founders cashing out while screwing me out of my paper gains.
> there are plenty of other capable engineers out there who are willing to take a lower stake for a variety of reasons.
Maybe, but they can't always find them! Businesses rarely fail for one reason but maybe 1/3 of the startups that approached me and failed were bogged down by poor technical decisions made early on (what's that? your engineering lead with 3 years of experience set up a totally custom kubernetes cluster and it's slowing down your execution? Man that's rough!)
Now you want to give a lot of small shareholders liquidity. The pricing is far more often. The whims of the world plus poorly negotiated deals can make a small sale be far below the last investment price. Psychologically this is bad even for wealthy investors and investing is heavily based on psychology.
No one wants to let that happen except the employees. The founders, the board, and the earlier investors don’t want anything that can jeopardize their argument for what their shares are worth.
In regards to the very first 1-2 employees, from what I have seen is that they are either a) fairly inexperienced (and therefore willing to take lower compensation), b) very excited about the technology and willing to work for less compensation, or c) very experienced and compensated well and/or given a ton of shares to the point where they may even be considered a founder.
So if you are employee #1 and you are very experienced and can negotiate for a nice chunk of shares, you almost always will get pulled into the founding team. It is not uncommon for startups to have minority founders that have 5-10% of the shares.
And that means when you hear about an early employee complaining about their compensation, they are most likely going to be from category a or b. You aren't going to be hearing from category c, because they were treated well and might even consider themselves founders.