Before asking if you should sell your business, figure out what you actually want and what the company needs. Evaluate the real consequences of selling, raising capital, getting acquired, recapitalizing, fixing things and waiting, or staying put.
The work I'm increasingly interested in is the conversation before that. What does the owner want? What does the company need? What's standing in the way? What happens economically under each choice? What happens personally under each choice? And which decisions create more options instead of fewer? Then we can talk about the transaction. And maybe the answer is sell. Great. Maybe it's acquire. Maybe it's bring in capital. Maybe it's recapitalize. Maybe it's fix the business for 2 years and revisit the question. Or maybe the smartest thing you can possibly do is keep the damn company. That's fine too, because the objective isn't to manufacture a transaction. The objective is to make a better decision. So if you're sitting there wondering whether you should sell your business, I'd start one step earlier. Don't ask, should I sell? Ask, what am I actually trying to accomplish and what choices do I need to preserve to get there? Because the transaction somebody is offering you and the decision you actually need to make aren't always the same thing.
