Provided is a lending system and computer system implemented method of lending facilitating profit sharing. The system provides a tool for use by lenders and borrowers to 5 enable peer to peer type lending arrangements to be established, monitored, analysed and reconciled. The system is configured to automatically identify compatible borrowers and lenders, establish the borrower/lender relationships, administer agreements, monitor the loan, and facilitate financial reconciliation and profit sharing on conclusion of the loan and/or individual single asset sale or per transaction. In some embodiments loans can be made up 0 of thousands of single assets across multiple borrowers and lenders. Embodiments of the system can also be configured to perform automated performance assessment of borrowers and/or lenders and output risk management data and ratings. Lenders and borrowers can interact with the system via an internet portal to manage their portfolio.