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I often get asked "How much is my collection worth?" It you have ever watched the "Antiques Roadshow" or a similar show where they tell you what something is worth, they usually put a disclaimer such as "At a well advertised auction, with the right people in the crowd" right before they tell the price. Shotglasses are just like any other collectible -- How much an item sells for depends on who is buying, but an equally important factor is how it is sold.
When selling a collection, there are a number of factors to consider: How much time and effort are you willing to put into the sale? What is your primary objective: "to get rid of them all" or "to get the most money?" Selling a collection as one lot is the fastest way, and it ensures that you "get rid of them all" but selling one large lot will probably not bring in the most money. Think of your collection as a "box lot" -- a jumble of items of varying value and importance that is being sold for a single price. Some people will buy a "box lot" because they want every item, but that is the unusual case. It is more likely that someone will buy the "box-lot" for one or two items, as long as the whole lot does not exceed the value of the item(s) they want. There are other people who will not buy a "box lot" because they do not want to have to deal with getting rid of the unwanted parts.
Selling each item individually is also not the best approach, especially if selling online, because most people are not willing to pay $3.00 shipping for a $3.00 item. Most collections contain a few items that are not very "desirable" for one reason or another: Maybe they are "boring" (a plain glass or one with a simple design) or made out of plastic (I hate plastic shotglasses) or maybe you have items such as bottle-stopper jiggers/pourers that most shotglass collectors are not interested in. If one of your goals is to "get rid of them all" then you will probably fail when trying to sell these individually.
A more balanced approach is to sell the collection in smaller lots. Selling smaller lots brings the price per lot down to where more people are willing or able to buy (more people can afford to buy a $10 item than can afford a $10,000 item). Smaller lots may attract more people by lowering the "signal to noise ratio" -- the amount of stuff you do want (the signal) compared to the amount of stuff you don't want (the noise) -- More people will buy a group of 10 items to get the 5 items they want than will buy a group of 500 to get those same 5 items. When selling many smaller lots, the "less desirable" objects might actually sell better -- a small lot of shotglasses and plastic bottle-top pourers, might be bought by a pourer collector, who would never have bid on the shotglass lot of 500. If selling online, selling smaller lots is more attractive to a buyer than the single glass approach because the shipping for an auction becomes a much smaller percentage of the total price for an auction.
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