Guest Contributor

The Cultivated Exit

April 19, 2022

Contributed by Brian Simon

If someone showed up on your doorstep today with an offer to buy your business, would you listen?  What number would it take to continue the conversation?  The eventual transition of your business may be the most significant financial transaction of your life.

There is a 100% certainty that you will exit your business–maybe by choice, maybe by circumstances beyond your control–and there are only three ways out: you can sell it to insiders; you can sell it to outsiders; or you can keep it until your death.  Which path is best for you?  Well, like a lot of things, the answer is: it depends.

We call our process The Cultivated Exit because we want you to grow your business and leave it on your terms.  We also use the term “cultivate” because there’s more to selling a business than just the transaction itself.  There are relationships involved, sometimes with real family, sometimes with work family, sometimes with both.  There is sophisticated planning that needs to be done to achieve the best results.  For more information about planning a transition, please check out our mini-course at

Here are some questions to consider for the future of your business:

  • How do you see your involvement in the business changing in the future?
  • What’s your next great adventure after you leave the business?
  • What obstacles could derail your personal or business goals in the next few years?
  • What role does your business play in helping you achieve financial freedom?
  • Do you plan to pass along ownership of your business or arrange for a sale someday?
  • Which method or methods have you used to assess the value of your business, and how confident are you in that process?
  • Given your buyer (or successor) plans, have you thought about who the best leader for your business might be?
  • What do you think will happen to your customers, your vendors, your employees, and your competitors if something happens to you?
  • Which planning suggestions have other business advisors given you to prepare for the future ownership of your business?
  • What do you see as your greatest challenge when you think about planning for the future?

Brian Simon is a Registered Representative and Financial Advisor of Park Avenue Securities LLC (PAS).  Securities products and advisory services offered through PAS, member FINRA, SIPC.  Financial Representative of The Guardian Life Insurance Company of America (Guardian), New York, NY.  PAS is a wholly owned subsidiary of Guardian.  Alliance Financial Group is not an affiliate or subsidiary of PAS or Guardian.  CA Insurance License ID #0G10296.  2020-103647 Exp 06/22.

Contact Brian by calling 239.561.2900 X203 (Office), 239.246.8928 (Mobile) or emailing