USA 1099 question

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We had an employee venmo payment to a person providing entertainment for a company party and now wants reimbursement. But my question is how to handle the 1099 aspect as the entertainer is self employed and should be a 1099 contractor but since the company didn't write the check I'm not sure how to handle.
 

DrStrangeLove

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Was the company party a party the company held for its own employees? If so, the entertainer was a vendor, not an employee, and a 1099 for the entertainer isn't appropriate.

If the company party was something it held for outside people--like, the company threw a bash for all its customers in a given area, for example--is this entertainer regularly employed by you to work such functions, and do you hold such functions regularly? If not, you could just treat the entertainer as a vendor of a service, if they were hired for just the one event. Again, no 1099 required; just treat the expense like any other payable.
 
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