Pros
My position allows me to be a fly on the wall. I interact with executives, entry level associates and mid-management folks on a regular basis. Very laid back environment. Upward mobility in this company is a very real possibility. The CEO, Dr. Patrick Byrne, is an eclectic student of eastern thought and this is very apparent in his decisions. Your happiness will very much depend on the department that you are in. I've luckily been placed in one where the department's VP knows me personally and will advocate for anyone worthwhile and coach the ones that aren't worth a grain of salt out. If you are seeking a rainbow friendly, pet-advocating, fair trade proponent employer then O.co is the place for you. Just read the next section to understand the cons.
Cons
Nepotism. Nepotism. Nepotism. This a prevailing theme inside of the organization. It wouldn't bother me so much if they were contributing members of their team. The benefactors are placed into positions they are so clearly unqualified for. This makes surrounding colleagues pick up the slack. If professionalism is something that you highly value, I'd suggest to keep looking. Vulgarity is quite acceptable and sometimes encouraged. Patrick always has a colorful comment during company-wide meetings - entertaining to me personally, but I can see how offensive certain people. Compare the salaries of senior executives against Amazon - Overstock pays theirs nearly double. This is very unwarranted for some executives and a real slap in the face when you see the disparity compared to hourly employees and the promise of a "bonus" each year. Management is very volatile. I understand this industry requires agile decision making, but the amount of change is staggering. Like I said, upward mobility is a very real possibility in this company - but that sometimes isn't a good thing. On the plus side, if you don't like your boss it's a very good chance you will have a different one in a few months. With any job, but especially this one in particular, I'd recommend having a backup plan and continuing to seek employment. I've known entire teams to disappear and executives traversing the many levels below them to personally fire someone if they don't like them.