We’ve made a bunch of decisions that I deeply regret because they were entirely monetary in nature. What I said to the team was, I’m fine with us making purely monetary decisions, but we didn’t even do those well.
It’s not as if we had a predictable rate of return that said, “We’re going to close our eyes here, double our money, and walk away.”
The reason I brought that up to them: Our decision-making can’t bleed over time. Right now it’s very hard for us, as an organization, to know how much should be mission driven and how much should not. When should we really double down on things that aren’t working, when should we not. When should we just give up?
It is the thing that we are now the most emotionally sensitive to. The opposite may be true: If the diabetes business turns out to work, does the 101st person that works in Social Capital say, “Fuck it, we’re just going to buckle down.” When they’re writing cheques and we’re 50 million deep into something and it’s clearly not going to work, was that it?
I don’t have a really good answer, but it’s the thing that I think about the most.
When do you know, how do you know, to keep going for it? When do you know that it’s too much? When do you know that your decision making is bleeding into a vein that is not constructive? I have no idea.
It’s powerful to be able to say, “I don’t know.”
American culture is a weird thing of know-it-alls. Everybody has to know everything. How the fuck can you ever learn [if everyone has to know everything]? When is that going to be valuable?
Own that one line: I don’t know.
Behind that is a self-awareness and confidence that I think is increasingly rare.