Various embodiments provide a system for enforcing investment policies created by an account owner. An investment policy tool may receive account data from an account database, including a portfolio and a policy, and a transaction generated by a trader for the account from a trading system. The investment policy tool may use the portfolio and the transaction to generate a speculative portfolio. The transaction and the speculative portfolio may be compared with the policy, to determine if either the transaction or the speculative portfolio violates any elements of the policy. If the investment policy tool determines that the policy has been violated, the investment policy tool may stop the transaction, stop the transaction and notify the account owner of the violation, hold the transaction and request approval from the account owner, or allow the transaction to proceed and notify the account owner of the violation.