I’ve spent the last decade evaluating long-term relationships through my work as a venture capitalist, investing in startups and founders. Now, as I step back into dating for the first time since I was 21, I’m struck by how much the venture capital mindset applies to modern relationships.

A candid reflection on dating after 40, men’s attraction to younger women, and navigating among confidence, competition, and self-worth.

In a recent podcast episode, I talked about something I’ve been reflecting on for a while: how easy it is to develop a default no mindset. Recently, I started questioning whether this approach was still serving me.