They're easy to find. Perhaps your use of
my entire career is a tell? You find these people doing non-work/non-tech activities.
Activities clubs are beneficial for this. But surprisingly, attending my kids' school sports events is also awesome. I meet parents from diverse backgrounds, and we instantly have something in common (kids on the same team). I meet a lot of people all over the income spectrum.
I live in a rural area that is quite poor. Over the past couple of years, I've encountered about a dozen parents who look and dress normal, but are wealthy, and they're either in or they run interesting businesses.
They all have super interesting stories and perspectives and you realize a lot of people are successful because they've tried a ton of different things. They don't have high success rates, maybe ~10%, but they're consistent and they're persistent.
(I also talk to the poor parents and hear their stories. I have this weird thing where I try to introduce some of the harder working and ethical poor parents to the richer parents, where there may be some mutually-beneficial opportunities, when they'd otherwise be too adverse to introducing themselves.)
