I like this answer to this question.
Benchmark’s Sarah Tavel: Startup Mega-Rounds Are ‘Double-Edged Sword’ | Fortune:
Do you think your operating experience has made you a better investor?
TAVEL: Without a question. One, you have an immediate level of empathy for the founders because it’s so freaking hard. Two, I’m much more interested than I used to be in the thought process that got to the metric they’re focused on today because that reflects how they’re running their company.
It’s important to remember that no company that goes through hyper-growth is always up and to the right. There are always these moments where you’re asking, “Are we going to lose this?”
I remember by the end of my time at the Pinterest, I joked that I felt like one of these veterans that you see in World War II movies. They would be sitting there, smoking their cigarettes when a little bomb goes off. All the new recruits run for their guns or jump for cover, while the veterans are still smoking their cigarettes. By the end of your experience at a high-growth company, you’re the veteran smoking the cigarette. And that’s who you want on your board. You don’t want the person who is going to be jumping for their gun or running for cover when there’s a little bump in the road because there will always be bumps. You want the person who isn’t frazzled by it and is always focused on the long-term. You can get that from 20 years of being a venture investor or from a few years of being an operator.