First, you will need to create a new dummy bank account. You will also need a due to the owner as a liability type account to use it for later reimbursement.
Step#1 Use bank deposit form (create + sign > other > bank deposit) to record contributed amount by the owner to pay a contractor. Account to show as due to the owner liability type account. See screenshot below.
Step#2 Use Expense form (create + sign > vendor > expense) to create contractor expense posted to appropriate expense account. See screenshot below.
Step#3 Use Check form (create + sign > vendor > check) to write the reimburse check to the Company Owner. See screenshot below.
In case there is no need to reimburse the owner (step#1), you will use a capital contributed account which would be an Owner’s Equity type account.
Review of 1099 vendors and payments list. See screenshot below.