If he is legitimately in business to the point where he is actively seeking sales or service revenue from customers or clients, he can enter the business expenses on his tax return to create a deduction. Otherwise, any expenses incurred up to the point of being actively open for business should be accumulated into a lump sum to be deducted as start up expenses in the year he is open for business.
The documentation required would be copies of invoices supporting the deductions and proof of payment of them.
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