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How to represent “out of pocket” purchases in general ledger journal entry?
You're lending the money to your business by paying for it directly.  The company accounts must reflect a credit (the amount you lend to it) and a debit (what it then puts that loan towards).   It's fairly normal for a small(ish) owner-driven company to reflect a large loan-account for the owners.  For example, if you have a room at home dedicated for the business it is impractical to pay rent directly via the company.  The rental agreement is probably in your name, you pay the rent, and you reconcile it with the company later. You could even charge your company (taxable) interest on this loan. When you draw down the loan from the company you reverse this, debit your loan account and credit the company (paying off the debt). As far as tracking that expenditure, simply handle those third-party invoices in the normal way and file them for reference.