A Conversation, a special bonus episode, taped in San Francisco in front of a live audience, here is the audio, video, and transcript. Here is one bit:
RAJAGOPALAN: …Daniel, if you’re looking for talent in investing or finance, how does that look different from the talent in the start-up world?
GROSS: In the start-up world? What makes a good investor is very different from what makes a good founder. If you were to make a scatterplot of it, some of the attributes are completely diametrically opposed. For example, I think very good investors are the right degree of optimistic but also realistic, whereas founders are too optimistic, which they should be.
At the end of the day, start-ups are a very funny activity when you think about it from a probability standpoint. Most companies fail. Almost all companies fail, and yet, people seem to be seemingly doing this activity over and over. They’re jumping off the cliff over and over again. You look over the cliff, and everyone who jumped off of the cliff is just on the ground dead, but people keep on jumping off the cliff. Founders are almost too optimistic.
When you’re evaluating a business, especially at later and later stages, I think optimism can be your enemy. Often, you see when a lot of founders later on in life — and I’m such a person — who started a business, sold it, and became an investor, you actually have to be able to wear very different kinds of psychometric hats. One of them is this continuum of realism and optimism. I’d probably say that’s the starkest difference between what makes a good start-up investor and a good founder. There are probably many others, but that’s the main thing that you look for.
I later have a monologue on chocolate ice cream, but overall Shruti steals the show. Recommended.