A method of maximizing the number of shares purchased under an ESPP with limited employee capital contributions, comprising the steps of selecting a monetary contribution amount or an amount to be deducted from an employee's monetary compensation for contribution to the plan, wherein the contribution amount is less than a maximum allowable contribution under allowable limits of the plan; selecting a rebalancing price at which the employee wishes to sell shares of employer stock at the end of an offering period under the plan; taking a simultaneous short and long position in derivative or other financial instrument that would allow for the disposition of shares acquired in the plan at an employee-designated strike price, the short and long positions having different strike prices; having a third party or broker-dealer provide a supplemental monetary contribution equal to a difference between the employee's selected contribution amount and the maximum allowable contribution under the plan over the course of the offering period on behalf of the employee to the employer; the supplemental monetary contribution received by a financial or ledger account used to purchase shares via the plan at the end of the offering period and the delivery of shares to a financial market counterparty or open market transaction to repay the proceeds of a interest free loan and comply with employee elections.