Immediately, the author assumes that everyone is playing a zero-sum game, which is the root of the problem with his viewpoint:
"We've got about 400 people in this room.... Imagine if dinner was carted into this room, and four people got half the food. The night would end in violence,"
It's actually lower than retail bank interest rates. For example, if they get a huge mortgage, usually it is at least 100 basis points lower. This is because these people are considered extremely low risk.
You are quite naive. These people don't have to sell their stocks in order to finance something like building a house. They get massive loans using their stocks at collateral.
"Delight" consumers was used 34 times in their S1. "Delighting" customers seems to be the new hip way to describe what SAAS companies should do these days. At the end of the day, it's nothing but marketing speak. Lemonade is not a true software company... it's an insurance company at its core. And let's be honest -- nobody gets delighted when buying insurance or making an insurance claim.
A lot of the comments here are about investors. Think about it this way as well: if you were an engineer, would you work for Skilling? Hell, if you were anyone that did anything, would you work for him?