Ask HN: Is Silicon Valley Becoming an Insiders Club?

I've been a web developer my whole career, with a CS degree, and 16 years experience. In 2007 I joined a new VOD startup and quickly rose to CTO position, then over the next 9 years grew it to 7-figure users and revenue, 16 engineers, and a highly respected brand in an industry niche. We hit a rough financial patch, so I left for another seed-stage startup which failed to gain traction.

Now, for the first time in 16 years I find myself looking for a job in SV without a direct reference. I was assuming that my broad experience, ability to bridge the technology-business gap, natural programming ability, and entrepreneurial spirit and tenacity would make me the kind of sought after employee that all growing SV companies claim they can't find enough of.

Unfortunately after interviewing at ten top companies (mostly later stage YC), I've been declined nine times. The last company where I felt the onsite went flawlessly and I had great rapport with every interviewer still thinks my experience isn't exactly the right fit for a tech lead position (even though this is exactly what I've done for the last 9 years!).

The things I think are hurting me are that I'm not great at whiteboarding, my experience is not at massive scale, and it's hard to summarize the scope and impact of what I've done as CTO growing a team from 2 to 16 engineers. Also the majority of interviewers are in their mid-20s and have come from Google, Facebook, Dropbox, Twitter, Uber, etc; I doubt they even have the context to understand the strength of my accomplishments. They seem to have fat hiring pipelines and value either top-1% algorithm brainteaser performance or specific large-scale experience at brand-name companies.

I'm coming away with the impression that SV is starting resemble the world of finance where pedigree is utmost importance. Is there anything to this assessment? Does anyone have any insight on the young hiring manager mindset in top YC companies these days?