mid-career networking/job searching

I'm 40, mid-career, 13 years post MBA
My background is in mostly in PE for about 10 years, briefly IBD before that, and a year in corp dev and IR for an NYSE-listed mobile Internet company.

I'm trying to network into my next job.
But I find it confronting, embarassing, and uncomfortable to reach out to alumni.
Plus there's so many social engineering rules - you can't ask for a job, you have to do "informational interviews" and ask for advice.
I dislike that too. It's so disingenuous.

My hope is to move back to Silicon Valley from overseas and join a tech company, or otherwise represent a tech company in Asia (where I currently live)

So how can one actually work w/ alumni to find a job or join a new startup company in some fashion?

1) trying to go thru the MBA database, find alumni that are in tech and do informational interviews

2) leverage my current role as head of investments at a family office to bring deals to VCs, and try to get close to them that way --> that is the "come bearing gifts" model

Open to other ideas. Thanks for helping a fellow WSO monkey