Someone made an interesting point on a discussion I saw yesterday: Travis has never worked at a company that he hasn't started himself[0]. He had a short stint at Akamai when one of his companies was bought but it was shorter than one year.
The take away is that he has never worked at a place with a rigid corporate structure or real HR. While that might be good for a startup that needs to move fast, it's not good if you want to learn on how to cultivate a healthy company culture, or have any empathy for your employees.
In other words, he has been running a college frat house for the past 7 years and it shows. He's probably more ignorant than mean-intended.
And too many entrepreneurs/co-founders in Silicon Valley are in the same position.