[bobiny]

I believe that deep and interesting conversations need to have stakes. In your example with VCs, stakes would be trying to figure out where the market is going or trying to strike a deal. Latter also works for rich people.

In context of modern social media, the main stake is emotional involvement. Which is often a sign of a shallow understanding of a subject.

Take reddit conversations on controversial subjects. There would be loud statements with many upvotes and counterpoints with many downvotes. And downvotes discourage debating for regular people. So you are left with homogenous opinions and trolls.

I think interesting conversations may happen with individuals that you stumble upon by chance. Easiest way to get lucky is to be involved in some community that fits your interests.