05/18/2026
I recently met with a business owner that is getting towards the end of his career and is going to be selling his business. He felt locked in, like everything was leading up to this. He felt like this was going to finally be THE WIN.
He is 52 years old and he came to me about 8 months prior to the sale of his business.
The deal was going to be a little north of $4,000,000.
He has spent his life on this.
Long days away from his family.
A lot of sacrifices.
It is his identity.
Like many owners, nearly all his net worth is tied up in the business, and the sale feels like the culmination of years of hard work and sacrifice.
Here’s what he did see.
In this scenario, the owner began exploring his options several months before a possible transaction. While he had focused extensively on growing the business and negotiating terms, he had not yet considered the broader tax and planning implications that can accompany a liquidity event.
And once you sign, that’s it. No fixing that.
This is where advance planning can matter.
When discussions happen early—while a deal is still under consideration and valuations are being evaluated—there may be opportunities to review ownership structure, estate considerations, and other planning strategies.
These steps don’t change the transaction itself, but they can help a business owner better understand potential outcomes and tradeoffs before decisions are finalized.
The broader lesson is not that the sale alone represents the “win,” but that preparation ahead of time can help business owners approach a major transition with greater clarity and flexibility.
Once an agreement is finalized, available planning options may become far more limited.
The win is how you prepare for it.
Because once that ink dries… that’s it..