As someone that is 46 and founding only his second startup, I can say that the wisdom and choices of how I've gone about this has felt like it's an order of magnitude improvement over my last startup which I founded in the early 2000s. And by this I mean, not just my choices in an absolute sense, but also relative to the rest of the startup ecosystem (which is obviously vastly different now).
I can draw a winding line from all of the things I've worked on over the last 20+ years, and see how they culminate in this current project. And I can draw upon a wide array of insights and learnings I've had along the way.
But the thing that I think gets underappreciated about older founders, is that the stakes are immeasurably higher. When you start something in your 20s and 30s, you see how the current project is something you are trying on, and you will evaluate how it fits. But failure is a learning exercise, and you know there will be other opportunities lined up waiting.
When you start something in your mid-to-late forties, knowing that a startup can often take 10+ years to see through to fruition, you have to consider that this could be your last meaningful project. So you start battling not just for success but for a sense that your life choices have added up to something meaningful. And that you've been able to have the kind of impact that you'd been working your whole life to have.
This might seem overly dramatic, but it's definitely the case for me. The shot clock is ticking down, and that does amazing thing to one's sense of focus and purpose.