In This Episode

The good news is you’ve gotten that offer you can’t refuse and you are going to sell your company.  Now the question is what do you do next?  Do you stay on with your company after the acquisition?  Do you ride off into the sunset?  Do you start another company?  So many choices and so little time.

We’ve been blessed in our coaching business to have taken several clients through the process of growing, running, and eventually selling their businesses.  While each situation is unique, there are several questions you’ll want to answer when deciding what to do next including the possibility of staying on with the new owner.

So here are some things to consider if you’re trying to decide if you should stay on board with your company after selling to a third party:

  • Employee vs. Boss: whether you’ve been running your business for five years or five decades, you can most likely appreciate that it’s very different being the boss vs. being an employee.  Our guess is you’ve done pretty well as a boss since you’ve been able to grow and sell your business.  But how are you as an employee?  Maybe you don’t remember what it was like to work for someone else.  Maybe you’ve never worked for someone else.  In any case, it’s going to be a big deal because you’ll now have to be answering to someone else.  Maybe you view this as a relief that you won’t have to make all the decisions any more or bear all the financial responsibility.  Be careful what you wish for.
  • Take Time: do you have enough money to walk away and not work anymore?  This might seem like an easy question to answer, but it often comes down to more than the money.  Give yourself permission to take some time off.  To figure out what you want to do next.  During the show today Jack talked about how he is a twice failed retiree.  What you tend to find is that even when you aren’t working to make a living and put food on your table, it’s still really fun and satisfying to run, grow, and operate a business.  So what if you took all the knowledge you now have and use it to do something new?  Most people never take a significant amount of time off.  How about a sabbatical for the business owner?  They don’t just have to be for professors!
  • Other Options: if you’re like many small business owners we know, chances are you don’t have too many hobbies or other interests outside of your business.  “So what,” you say, “now I’ll have time to pursue those other interests!”  Well yeah, maybe.  Don’t be so fast to put aside business as an interest.  Most people don’t realize how fun, exhilarating, and rewarding business ownership can be.  Too many folks think about work as being a job.  You know better.  Maybe there is another business or two you could help.  Perhaps become an investor or a partner in another business or two and bring your knowledge and expertise.
  • Significant Other: what’s your significant other think?  This could be your spouse, life partner, best friend, whatever.  If you’re currently living with someone, how do they feel about the possibility of you being around more often.  Of you not having anything in particular to do.  Of getting in their way.  It can be a bit of a pain dealing with someone who doesn’t have to work any more.  The people closest to you should tell you how things really are and provide a good sounding board for you.

As discussed on the show today, we’ve counseled several people through this process and we’ve been through just about every situation you can imagine.  Many of our clients chose to stay with the company that bought them.  The reasons for doing this include curiosity, loyalty, and fear.  The curiosity piece of what’s it like working for someone else/a bigger company/etc.?  The loyalty piece comes from not wanting to abandon your team and walk away once the deal closes.  Many of your employees have been loyal to you and you want to show that in return.  The fear piece is just typically fear of what’s next.  You’ve been working for as long as you can remember.  What will you do if you aren’t working any more?  Hopefully today’s show helps you work through these and many other questions you have when considering whether or not you want to stay on after selling your business.

People, Companies and Resources We Mentioned in the Show

Should I Stay or Should I Go” by the Clash (

“Hotel California” by The Eagles (

Terry Walkerly DSSB Interview Talking About Getting Fired From Every Job He Had (April 7, 2022) (

Shark Tank (