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Well, to be fair, most of the borrowed money came from his own pocket, which is why he ended up owning more than 40% of zappos (probably more that 50% if you include venture frogs' 36% involvement).

Most boards hate companies who spend extravagantly on their employees. For example, even though Google is doing great, quite a few of their board members hate how Eric Schmidt feeds Google employees so well. According to a few I know at google, they had to pull back a few items on the menu to keep the board happy. Most boards are just after profits and don't really see the connection to employee happiness.

In fact, there was a YC company board who rejected the purchase of an expensive espresso machine just because the employees wanted it... that destroyed employee morale for the next 2-3 months, and also caused traffic to go down. Eventually the board gave in and bought the company the espresso machine and it really paid off -- employees were happy, traffic rebounded, and board members actually stated that they wished they knew this earlier. Won't say which YC company, but it was a talk from one of the YC dinners during my round.

tl;dr: Boards are always after the cash and rarely see the connection to keeping employees happy, yet time after time they make the same stupid mistakes.



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