The work culture is beyond your standard “work long hours startup”, Square wants your soul. After voicing my concerns to my manager that the amount I was expected to work was jeopardizing my overall happiness and time spent with my spouse, I was told in no uncertain terms that I could either choose to spend more time on my relationship or Square. There was no middle ground. As you can probably guess, I chose the former. I expect that relationship to last much much longer than Square will be around for.

Jack is a curious CEO, though with little experience running a company. I mean, the guy got kicked out of Twitter. He also works two full time jobs, both as CEO of Square and whatever he does at Twitter nowadays. The company culture comes from top down. When your CEO works two full time jobs, lives within a 4 block radius of both of them, doesn’t invest a lot of time in friends, family, or other non-work related relationships, everyone that gets hired below that is expected to do the same. My own social life started to dwindle rapidly in my time there and almost everyone else I spoke to experienced the same.