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InvestHub.com's
Finance Dictionary and Glossary of Investment Terms

Cashless Exercise  

Definition 1.

A transaction that is used when exercising employee stock options (ESO). Essentially, what you do here is borrow enough money from your broker to exercise the options. You then simultaneously sell enough shares to pay for the purchase, taxes, and broker commissions.
 

Definition 2.

A method of converting options into stock that requires no initial cash payment to cover the strike price. Essentially, a broker briefly loans enough money to exercise the options, and a portion of the stock is sold immediately after exercise in order to repay the broker. In this respect it is essentially buying on margin. The broker is willing to enter this arrangement when that broker feels that the option holder will honor his/her commitment and quickly sell his/her stocks to settle the debt to the broker.
 
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