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Never found a sustainable business model that justified the considerable expense of running their site
Many people will tell you that they will become paying customers if you build this feature or that feature. Even if you build it, 9 times out of 10, that person won't become a paying customer, and you just spent a lot of time and energy building something that nobody uses. Be careful when talking to non-paying users.
Trade violations, founders and board members were accused of illegally bidding on auctions breaking the law.
Instead of building a great and very simple MVP, created an unstable product with too many features
Big Board, Young Team, Mindless Management -- When you have an overly experienced board, and a technically talented young team who don't see eye to eye, you do not fix it by bringing in an ex-accountant to be COO / Manager, especially if they no idea about startups or tech.