> I noticed that a particular sliver of my contemporaries had stopped pretending to be broke, or poor

My thoughts on this: its kind of self-fulfilling by the culture.

Although I was raised to rely on my own earnings for everything, some of my parent's colleagues quipped that some of my accomplishments and risks I took were because I could fall back on my parents. My parents were insulted, I was insulted .... at the time. Were my 13 hour days and multiple jobs and barely making rent after barely finishing a college degree irrelevant!? But then I started to wonder if subconsciously it was true. Or what other forms of privilege I was enjoying. What I found was that the support system while I was in grade school and college was very important, and the lack of some distractions is important, but I still found that I had to play the cards I was dealt very meticulously, I was relying completely on my own acumen and finances - at the time.

Where this introspection did lead me though, was that I wasn't taking enough risk because they were correct, my parents would support me. So I took on more risk because "the proletariat" forced that perception on me and there's

A) No point in bragging about having no support from parents.

B) No point in wasting time being poor for the bragging rights. We are not the same no matter what.

My parents were familiar with corporate America and a career like that. I did that and I was good at that. But as I had begun noticing what a "friends and family" round was, and all these startup founders had their seed rounds filled by their parents, I noticed the complete cultural difference between the other side of society that says "don't take money from family" because of the idea that it will ruin all relationships. No, turns out when the covenants are clear, like with equity, as opposed to a promissory note, people are willing to be professional about it. So I did the same. Something I wouldn't have done, and made money on that, and took the difference as described in the contract. It wasn't all uphill, it was dangerous and scary and sometimes a loosing bet. But there was enough resources to do it again if necessary. I wouldn't have ever even tested the limits of my parents willingness to support. But now I can more clearly see other groups of people who have actual generational wealth based around this. Based around asking for millions of dollars of support into their new hedge fund, from their parents or community. The legal trusts that unlock as different rites of passage are hit, correlated with age. Something previously unrelatable, but now I see it. And I wouldn't have noticed if salty people didn't force their differences on me.

I feel like others have reached similar conclusions. That its gotten kind of boring pretending that "I got a good deal on rent" in that expensive area. Not everyone is rent controlled and good deal meant market price. The paths diverge, just own it.

If you have a card to play that helps your goals, then play it.

The trust fund kid that has a successful startup they didn't need to save up for could just as easily been an ambitionless person, perhaps even distracted by vices.

So its all about playing the cards you were dealt. I respect that, no matter what the cards are now.

I think the push to “recognize privilege” actually accelerates people to double down on it. Like oh we’re not pretending anymore, then lets make this gulf as wide as it can go.