I worked for an established company (not a startup) and had a run in with Wal-Mart. Wal-Mart managed to buy some stuff at an ultra low discount because ... someone thought maybe if we get in there we could sell tons to their IT team.
Meanwhile I'm working with their IT guys. They hate the product. They tell me in no uncertain terms and in every unprofessional way you can imagine (that part was pretty shocking). Of course what they're really doing is just buying the minimum and pounding the hell out of support with complaints as they pump 20 gallons into 10-gallon hat of our product.
What happens? We keep providing them free services, extra services. The folks at the top think they're at the tip of a big sale, big money despite myself and others telling them "These guys don't like our widget, they don't want it... and they're not capable of even making good use of it. All while giving it to them for free, why would they pay a dime more?"
By the end I hear we've made like our 5th pitch to them that is barely profitable for us... just on the face value of the product and support. Somehow Wal-Mart convinced these guys to take a 'big sale' moment and turn it into a loss if you consider all the time put into working with them. And they were happy to do it.
Finally we had a stroke of luck, we were acquired, and the new CEO had worked with Wal-Mart before as a customer and cut them lose. Finally all that effort and energy that went into this big deal that never happened (probably for 18+ months) could be put to use with better customers.
It's amazing how some folks can over time convince other people to actually propose a bad deal... for themselves.