You sound pretentious, hence why you don't inspire VPs enough to follow your projects. For that purpose, being skilled in SWE is barely important comparing to relational skills.
It's time to question yourself.
I think the main problem is that the average investor feels uncomfortable around me when they know my backstory. Maybe it makes them question the meritocracy narrative. Maybe they feel guilty (about their own success) by being around me. People don't like to be reminded about how lucky they are.
Respectfully, it seems like you didn't take the following comment to heart.
> You sound pretentious, hence why you don't inspire VPs enough to follow your projects. For that purpose, being skilled in SWE is barely important comparing to relational skills. It's time to question yourself.
Instead you deflected, re-asserting your internal monologue of: it's not me, it's them. It doesn't matter what your backstory is if you're not likable. That isn't a judgment on your character -- you may be a wonderful person and friend. Likability is a skill that can be learned, and one that is arguably more important than any software skills you may have (as you may have implicitly observed).
I get that, but if I must change who I am to fit in with specific people, then that would make me a phony. Though I suppose at that level, most people are phony. Phony is normal and genuine is awkward.
I guess when a rich person is always surrounded with phony people who will do anything to get something from them, it must feel uncomfortable to be faced with genuine people who just tell it like it is.
It's easier to fool someone than convince them that they have been fooled. It's easier for someone to like you by telling them what they want to hear than by telling them the truth.