I sincerely wish him luck. It was a blunt, forthright essay. Lots of self-revelation, and he didn't sugarcoat anything. I don't know the chap, but, from what I read, the essay seems to fit his personality.
I might not enjoy working for him (but I could be wrong -I often am), but I completely sympathize with him, and his essay gave me a good window into the current SV mindset. I am glad to read his empathy for folks that don't have it as good as he does, and I suspect he has it pretty good. I don't encounter that kind of awareness too often, and it's nice to hear, from a C-level. He seems to have both feet planted firmly on the ground.
I worked for some fairly "stolid" corporations, for most of my career. It was not a particularly enjoyable experience, the whole time, but it taught me a lot of things about Integrity, Loyalty, personal Honor and Consistency. I was never paid FAANG wages, but was, nevertheless, able to build up enough of a "nest egg" to get to the point where I don't need to work, if I don't want to. I'm currently working with a 501(c)(3) startup, not making a dime, and working harder than I ever have in my life.
And loving it. I currently feel as if it has all been worth it.
The thing that really bothers me, is that the entire tech industry is now built around engineers remaining at a company for 18 months. I was talking to a Facebook manager, some time ago, and he was boasting about being at FB for longer than he had ever worked anywhere.
"How long was that?" I asked.
"27 months."
I worked at my last company for 27 years. It has drawn a lot of sneers from current SV denizens, but I'm proud of my record. I went places that people have no concept of. I worked at a level of trust, for a conservative, classic Japanese corporation, that few Americans ever experience, and my tenacity and Integrity had a lot to do with it.
When high turnover is endemic, it has a huge impact on architecture, corporate culture, productivity, hiring, and, at the end of it all, product quality.
I tend to design fairly large, heterodox, infrastructure systems. They take months and years to develop and refine, and I expect them to last for years. I have written software architectures that are still in use after 25 years (albeit greatly changed).
In my experience, "letting go" is vital. I spent ten years developing and refining a project that I turned over to a new team, about three years ago, and walked away completely, so they don't have the "Grandpa can't let go" thing happening. They have done very, very well. My being there would have destroyed a decade's worth of work. Instead, they built out my infrastructure into something amazing.
Walking away also gave me the luxury of working on new stuff. I'm in the middle of refactoring a server system that I wrote two years ago. It lay fallow until the project I'm working on now, and it has aged very, very well. I look forward to, one day, turning it all over to someone else, and walking away to new horizons.