Bah, not a huge surprise given how brutal the travel tech industry is, but they remained my fav travel site - seemed to often find fares that were missing off google flights or other competitors. Loved the U/I too. RIP.
If nothing else, he held his equity for long enough to only get hit by long-term capital gains taxes. (per wikipedia, in canada, that's half your typical tax rate).
Yeah, a lot of big bay-area and boston funds now have NYC offices too. General Catalyst - mentioned as being based in Cambridge in the article has an office on Lafayette street in NYC now with a couple of partners in it. This has changed the funding game more than the homegrown VC's (USV, as an example).
Depending on their workloads, running their own datacenter(s) might save them millions a month. I know it does in my own case. That said you give up flexibility for the $ savings. They may think the additional flexibility is worth the cost differential at this point.
My guess would be more along the lines that people who walk/subway are generally more fit than those who take a car everywhere. NYC doesn't have a lot of fat people in general. (though it's worse than it used to be)