This paper explores how private contracts tailor GAAP and whether tailoring reflects the characteristics of the contracting parties. The analysis reveals that contracts of bank and insurance lenders are different with bank agreements closer to public debt. Tailoring is one of several characteristics associated with insurance lending agreements. The extensive tailoring of GAAP income in insurance contracts enforces dividend and payout restrictions that are consistent with the interest of long-term insurance lenders. In contrast, bank lenders deal with borrowers' default risk by negotiating shorter maturities, security, sinking funds, and loan syndication.