Via investopedia

And, yes, the financial markets also use common Thanksgiving terms for their own purposes, and they have room for pilgrims and turkeys. 

Pilgrims in the markets, though, often walk barefoot. A "barefoot pilgrim" is a slang term for an unsophisticated investor who loses all of his or her wealth by trading equities in the stock market. A barefoot pilgrim is someone who has taken on more risk than necessary or entered investments carelessly, without doing the proper research. An investor shouldn't take on more risk than necessary to achieve her required return, so someone desiring a 3% return should invest in Treasury securities, not the stock market, and an investor requiring an 8% return should invest in the S&P 500, not in emerging markets. 

A barefoot pilgrim is someone who has lost everything, right down to his shoes, because of his poor investment choices. Becoming a barefoot pilgrim is akin to losing your shirt. A sophisticated professional investor might condescendingly refer to a non-professional investor he perceives as naive, as a barefoot pilgrim. A barefoot pilgrim's trading decisions could be viewed as on par with gambling. 

Allegedly, pilgrims ate turkeys and that is why turkey is the main course in Thanksgiving. But if you eat a financial turkey you may have digestion problems. Investopedia defines "turkey" as a slang for an investment that yields disappointing results or turns out worse than expected. Failed business deals, securities that realize significant losses and unsuccessful initial public offerings (IPOs) could all be called "turkeys". For an individual investor, a turkey could be a speculative equity investment in a startup technology company that subsequently goes bankrupt. For a corporation, a turkey could be the purchase of a smaller company that ends up producing much less revenue than anticipated, making it an investment that gobbles up the company's profits.

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