Is it easier to go from an operational role to VC or from VC into an operational role?
Part of the answer(s) depends on how long you’ve done either.
Venture Capital is an incredibly specialized skill set. If you’ve been an associate, analyst or principal for a few years … those skills can (sort of, kind of) translate into biz dev, partnerships, strategy, etc. That’s an easy transition.
But … as time goes on … and all you have ever been is a VC for 10, 12 years … those skills don’t really add much operational value at all. Unless it’s into a corporate venture fund or maybe corp dev.
A lengthy operating history, e.g. CEO, founder, etc. also only helps being a VC up to a point. And the higher up the org chart in the better of a company, the better for sure. And the further you took a successful startup as a founder-turned-VC, the better for sure. But at some point enough is enough to be able to evaluate other start-ups … and to get them to pick you.