Simmons learned how to ask after one Barter Babe, a veteran barterer, told her she needed to post a wish list. Following the advice, she eventually got not just one bike but two (one for her and one for Matt), a TTC pass, yoga lessons, a haircut and food she wanted to eat, among hundreds of other things. Simmons made exceptions for some unique trades, too, such as both circus performance training and butter churning lessons, the latter of which she now barters as a skill to others. She even worked up the nerve to approach local businesses in person, armed with a business case for barter. One café near her apartment traded a month’s worth of morning coffee for a financial session; a boutique hotel, Hotel Ocho at Queen and Spadina, took a financial seminar luncheon for its employees in return for an overnight stay for Simmons’s parents, who were celebrating their 35th anniversary.
Yes…yes…yes! When I went to school to become a Registered Massage Therapist, and discovering how difficult it (still) is for a male RMT to get a legit job be it here or a small town, our instructor told us to consider bartering whenever possible. This was in a smaller city (100,000) where bartering can do well for you to make inroads with the Downtown Council, locally owned businesses; let’s say for example a new yoga studio or health club or salon is opening. I bring my massage chair over and do free 10 minute chair massages and give out my business card, in exchange, the yoga groups can use my space if they need to add an extra class. The salon knows if they’re doing a training on a day I’m not working, they can use my studio. Things like that.
While it may be free, there is no one monitoring the barter ads, so you must be aware of potential Craigslist scams, and realize that you are always at risk when it comes to meetups and exchanges. For example, about a year ago, I arranged to trade massage gift certificates for housecleaning. Since the individual was coming to my home, I was more nervous than usual. However, she offered good previous references, and we  arranged for a time to meet when my husband would be home, in case an odd, unexpected, or even dangerous situation arose.
Barter, the direct exchange of goods or services—without an intervening medium of exchange or money—either according to established rates of exchange or by bargaining. It is considered the oldest form of commerce. Barter is common among traditional societies, particularly in those communities with some developed form of market. Goods may be bartered within a group as well as between groups, although gift exchange probably accounts for most intragroup trade, particularly in small and relatively simple societies. Where barter and gift exchange coexist, the simple barter of ordinary household items or food is distinguished from ceremonial exchange (such as a potlatch), which serves purposes other than purely economic ones.
In recent years, barter has enjoyed a resurgence as a means of countering economic insecurity, unemployment and worker exploitation. The nature of modern-day work, the pervasiveness of the Internet and the rise of social networking have all contributed to its spread. Other examples of alternative economic systems include gift economies, sharing economies and time banks.
As Orlove noted, barter may occur in commercial economies, usually during periods of monetary crisis. During such a crisis, currency may be in short supply, or highly devalued through hyperinflation. In such cases, money ceases to be the universal medium of exchange or standard of value. Money may be in such short supply that it becomes an item of barter itself rather than the means of exchange. Barter may also occur when people cannot afford to keep money (as when hyperinflation quickly devalues it).[15]
Trade did occur in non-monetary societies, but not among fellow villagers. Instead, it was used almost exclusively with strangers, or even enemies, where it was often accompanied by complex rituals involving trade, dance, feasting, mock fighting, or sex—and sometimes all of them intertwined. Take the indigenous Gunwinggu people of Australia, as observed by the anthropologist Ronald Berndt in the 1940s: 

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. 

Anthropologists have argued, in contrast, "that when something resembling barter does occur in stateless societies it is almost always between strangers."[6] Barter occurred between strangers, not fellow villagers, and hence cannot be used to naturalistically explain the origin of money without the state. Since most people engaged in trade knew each other, exchange was fostered through the extension of credit.[7][8] Marcel Mauss, author of 'The Gift', argued that the first economic contracts were to not act in one's economic self-interest, and that before money, exchange was fostered through the processes of reciprocity and redistribution, not barter.[9] Everyday exchange relations in such societies are characterized by generalized reciprocity, or a non-calculative familial "communism" where each takes according to their needs, and gives as they have.[10]

Other anthropologists have questioned whether barter is typically between "total" strangers, a form of barter known as "silent trade". Silent trade, also called silent barter, dumb barter ("dumb" here used in its old meaning of "mute"), or depot trade, is a method by which traders who cannot speak each other's language can trade without talking. However, Benjamin Orlove has shown that while barter occurs through "silent trade" (between strangers), it also occurs in commercial markets as well. "Because barter is a difficult way of conducting trade, it will occur only where there are strong institutional constraints on the use of money or where the barter symbolically denotes a special social relationship and is used in well-defined conditions. To sum up, multipurpose money in markets is like lubrication for machines - necessary for the most efficient function, but not necessary for the existence of the market itself."[12]
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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.
Some businesses that may not directly barter with customers may swap goods or services through membership-based trading exchanges such as ITEX or International Monetary Systems (IMS). By joining a trading network (which often charges fees), members can trade with other members for barter "dollars." Each transaction is subject to a minimal fee; the exchange facilitates the swap and manages the tax components of bartering such as issuing 1099-B forms to participating members. You may find a nearby exchange through the International Reciprocal Trade Association (IRTA) Membership Directory. Before you sign up and pay for a membership, however, make sure that members offer the types of goods and services you need. Otherwise, you may find yourself with barter money or credit that you cannot use. 
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