If you will have an employee you must pay them as such and they must fill in a W-4.   

If they will be a sub contractor then before you pay them dollar one have the fill in the W-9 even if they will be below the $600 requirement to issue a 1099.     If you are ever audited then you will need this info for the IRS to support your deduction. 

And yes ... if you are taking the deduction then they must report the income even is no 1099 is issued.  

Q. Can I deduct this expense from my taxes, and if so how do I prove it. 

A. You don't pay in cash.  You pay by check or electronic transfer. 

Paper Trail = audit protection 

Thank you. So with that low amount of payment I don't need them to fill out a W-9 and claim it in order to deduct it from my taxes? I can just pay them electronically and this will be enough? 

ALWAYS  CYA  by having them fill in a W-9 ... they are free and simple.  Never pay anyone a dime until you have this info ... you may think you will only pay them a small amount now but what happens if you do over that amount later in the year and you have no luck tracking them down in January for the needed info.   If they will not fill in a W-9 for you then you don't need to use them ... it is a disaster waiting to happen. 

https://www.irs.gov/pub/irs-pdf/fw9.pdf

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@Dallisaurora  wrote:

Thank you. So with that low amount of payment I don't need them to fill out a W-9 and claim it in order to deduct it from my taxes? I can just pay them electronically and this will be enough? 

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You will be required to issue a 1099-NEC if the amount you pay is more than $600. 

If you don't request a W-9 now, you could end up in hot water if your business expectations change and the person decides later to take your money and not give you the form.  You can request the W-9 to have the information on file, without issuing the 1099-NEC if your payments are under $600.