It's just casual life differences accumulating over time. They may not even notice it's strange to others since it's just how their life works now.
Somebody who has been an employee at 4 successful startups over 10 years has different life patterns ("yeah, I'm an employee, but I'm also an LP in some VC funds and I angel invest on the side and take advisor shares every few months") than someone who has also worked at startups for 10 years but every previous startup they worked for failed or no longer exists.
"Oh, you cashed out some stock during your startup's latest funding round and now you're complaining your Tesla order is being delayed by two months? I'm soooo sorry. What's new with me? Thanks for asking! I got a yearly salary increase of 0.5% again this year, which doesn't in any way cover the 15% yearly rent increase on my apartment. Enjoy your new $100,000 car while I scrape together another $300/month for rent I don't have."
Its not obvious nor is it as common as the GP makes it seem.
For a concrete example: https://news.ycombinator.com/item?id=10410723 -- A thread in which some guy asks about renting a Skylake-based server. When I read it originally it already had 3 people telling to build it himself as though a $1000 system is loose change you people in SV find down the back of your couch.
Somebody who has been an employee at 4 successful startups over 10 years has different life patterns ("yeah, I'm an employee, but I'm also an LP in some VC funds and I angel invest on the side and take advisor shares every few months") than someone who has also worked at startups for 10 years but every previous startup they worked for failed or no longer exists.
"Oh, you cashed out some stock during your startup's latest funding round and now you're complaining your Tesla order is being delayed by two months? I'm soooo sorry. What's new with me? Thanks for asking! I got a yearly salary increase of 0.5% again this year, which doesn't in any way cover the 15% yearly rent increase on my apartment. Enjoy your new $100,000 car while I scrape together another $300/month for rent I don't have."