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This sort of scenario was so undesirable that societies must have created money to facilitate trade, argues Smith. Aristotle had similar ideas, and they’re by now a fixture in just about every introductory economics textbook. “In simple, early economies, people engaged in barter,” reads one. (“The American Indian with a pony to dispose of had to wait until he met another Indian who wanted a pony and at the same time was able and willing to give for it a blanket or other commodity that he himself desired,” read an earlier one.)
Other countries, though, do not have the reporting requirement that the U.S. does concerning proceeds from barter transactions, but taxation is handled the same way as a cash transaction. If one barters for a profit, one pays the appropriate tax; if one generates a loss in the transaction, they have a loss. Bartering for business is also taxed accordingly as business income or business expense. Many barter exchanges require that one register as a business.
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However, this isn’t always possible. For instance, you may have a $150 digital music player and want a small refrigerator worth $100. In this case, if both parties are certain of what they want and understand the difference in value, there should be no barterer’s remorse. Alternatively, you can ask for the mini-fridge plus $50 to make the trade – the worst anyone can say is “no.”
Bartering does have its limitations. Many bigger (i.e., chain) businesses will not entertain the idea and even smaller organizations may limit the amount of goods or services for which they will barter (i.e., they may not agree to a 100% barter arrangement and instead require that you make at least partial payment). But in an economic crunch, bartering can be a great way to get the goods and services you need without having to pull money out of your pocket.
In his analysis of barter between coastal and inland villages in the Trobriand Islands, Keith Hart highlighted the difference between highly ceremonial gift exchange between community leaders, and the barter that occurs between individual households. The haggling that takes place between strangers is possible because of the larger temporary political order established by the gift exchanges of leaders. From this he concludes that barter is "an atomized interaction predicated upon the presence of society" (i.e. that social order established by gift exchange), and not typical between complete strangers.
It’s hard to answer that without actually seeing a modern gift economy in action. Luckily, modern gift economies actually do exist. On a small scale, they exist among friends, who might lend each other a vacuum or a cup of flour. There’s even an example of a gift economy on a much larger scale, albeit one that’s not always in operation: The Rainbow Gathering, an annual festival in which about 10,000 people gather for a month in the woods (it rotates among various national forests around the country each year) and agree not to bring any money. Groups of attendees set up “kitchens,” in which they prepare and serve food for thousands of people every day, all for free. Classical economists might guess that people would take advantage of such a system, but, sure enough, everyone is fed, and the people who don’t cook play music, set up trails, teach classes, gather firewood, and perform in plays, among other things.
In the United States, Karl Hess used bartering to make it harder for the IRS to seize his wages and as a form of tax resistance. Hess explained how he turned to barter in an op-ed for The New York Times in 1975. However the IRS now requires barter exchanges to be reported as per the Tax Equity and Fiscal Responsibility Act of 1982. Barter exchanges are considered taxable revenue by the IRS and must be reported on a 1099-B form. According to the IRS, "The fair market value of goods and services exchanged must be included in the income of both parties."
He would have heard of channels and sandbanks, of natural features of the land useful for sea-marks, of villages and tribes and modes of barter and precautions to take: with the instructive tales about native chiefs dyed more or less blue, whose character for greediness, ferocity, or amiability must have been expounded to him with that capacity for vivid language which seems joined naturally to the shadiness of moral character and recklessness of disposition.