I know we’re at dangerous levels of Chris Sacca overload. But in a three-hour, contentious, emotional, funny, and candid conversation with the sole partner managing $1 billion in assets, there was a lot to highlight.

One of my favorite insights that he brought up last night was about the difference between Google under Eric Schmidt and Google under Larry Page. As Sacca — an ex-Google exec under “the triumvirate” — described it, Schmidt’s leadership rigor allowed Page and Sergey Brin the freedom to engage in outrageous thought experiments that led to wacky projects like the self-driving car. If Page has to be the responsible exec, does he self-censor too much?

Later, he remarked on why Google fundamentally doesn’t get Twitter, saying it was the same reason Google never put adequate resources behind Evan Williams’ first company Blogger. Because both are more art than science. Put another way: Neither solves a math problem. That could explain the mixed success of Google’s social efforts under Page.

On the subject of Twitter, Sacca not only shared his views on the ousters of Jack Dorsey and Evan Williams, but he explained why he thought keeping Twitter independent was so important.