A gypsy swap is a unique method by which a company may raise capital without issuing debt or holding a secondary offering. In many respects, a gypsy swap is similar to a rights offering. except that the restricted party's equity claim does not elapse and the swap instantly becomes dilutive. (To learn more about rights offerings, be sure to read Understanding Rights Issues .)
The gypsy swap is broken into two parts:
1. An existing shareholder exchanges freely traded shares for restricted shares (shares restricted by time and/or price constraints) from the issuing company. In economic terms, the existing shareholder neither gains nor loses money from the transaction, although it may have tax consequences.
2. The issuing company then sells the existing shareholder's freely traded shares to a new investor(s) at a price that may be higher or lower than the current market price. The issuing company now has additional capital and the new investor(s) has equity in the issuing company.
In almost every case, a gypsy swap is a last-ditch financing option because the new investor(s) almost always demands some combination of below-market value price or special consideration from the deal. In fact, if the issuing company could raise funding conventionally - internally from the equity markets or from the debt markets - it certainly would choose to do so.
This question was answered by Justin Bynum .