(published on LinkedIn July 2, 2019)

If you are working toward selling your business and you receive a proposal to sell the stock in your business, rather than the assets, I suppose you would be happy. Chances are you will be taxed at capital gains rates rather than ordinary income tax rates… all is well.

Assume, for this post, that the buyer is willing to pay your asking price. However, she wants to pay it over a long period of time and you are asked to “carry the paper” (the buyer will provide you with a promissory note to memorialize the debt).

Couple of thoughts:

• Be cautious. If you get a pledge of your stock as security, you may think that is sufficient. Think again. If the buyer drives the business into the ground and stops paying you under the promissory note, what good is the stock?
• Be creative. Oftentimes, there are alternatives… a lien on the underlying assets, personal guarantees, letters of credit, etc. Also, consider accepting a lower purchase price in order to accelerate the payments over a shorter period.

Bottom line, you are not wed to any deal structure. Consider several alternatives and analyze the consequences with your attorney. Remember, there is no correct answer; however, there are bad results.