- CEO: This is a publi company, but not really; It's his way or the highway. That's fine, and that makes sense given his financial family inheritance, and his proxy vote for his family and other board members. It's reality. This is NOT an ad hominem smear, but a valid concern for anyone considering employment here. He's a poor judge of character, irrationally reliant on devout trust in and devotion towards him and his abusive, flighty, and paranoid ego. Those whom he has personally mentored into leadership positions would be and actually are hard pressed to find even remotely equivalent employment elsewhere (and have actually lead their personal lives to ruin under his tutelage). So the CEO is one of two people that ultimately matter. (The CEO is quite bright and would make an entertaining lecturer or dinner guest, but these traits don't translate into his presence being a pro of employment at Overstock.)
- President: You shouldn't cross the President whose emotions, whims, hobbies, and ire are followed by her pawns -- and quite often by the CEO -- with Pavlovian aplomb. What makes this unique and a con is: 1) the fact that the President has a long and twisted relationship with the CEO where he appears to be directly controlled by the President (e.g., the CEO says he won't tolerate dishonesty, but the President regularly lies to him and plays him like a fiddle), and; 2) that the President is financially illiterate, both in fluency with data and P&L, and personal finances (having had to be bailed out by). As a result, the company will always trip over itself. Like the CEO, the President is paranoid and a narcissist, so be warned that if you cross her or someone in her network, and you'll soon find yourself shown the door as scores of others have, both high and low.
- Deep Capture: This is the name of the CEO's quite interesting and compelling blog where this self-styled, typo-ridden CEO-journalist endeavors to reveal the flaws in our financial/governmental systems. The concept of deep capture is that legislators and regulators -- those who are to ensure order and fairness -- are captured pawns of powerful and greedy financial barons. Why should prospective employees care? Because the CEO has unwittingly created the same scenario at Overstock, where he is the captor, and senior and lower executives are bound by velvet handcuffs from behaving rationally, justly, or even honestly. This is less troublesome in a public company than a democracy, but it will impact your potential job here (i.e., no one really has your back), so I thought you should consider it.
- This next point is relevant given the Utah location. There's increasing anti-Mormon sentiment among leadership and at the company broadly. Consequently, deep schisms are being opened in the company culture. Statements that would violate protected classes are more frequently uttered in certain circles, and after work hours among management and sr. management. Those who point to some Mormon execs as counter-proof avoid the fact that these few are marginalized "yes men" who are on their way out, or are captured.
