Sarah Tavel has spent the past four years as a general partner at venture capital firm Benchmark, after previously serving in the same role with Greylock Partners and as the first-ever product manager at Pinterest. In this episode Shane and Sarah how studying philosophy helped in her career as a venture capitalist, the value of intellectual rigor, her concept of the net-present value of pain, why every strength has a corresponding weakness, where executive boards go wrong, assessing the performance of a CEO, lessons of rapidly scaling at Pinterest, and so much more.