M&A + Liquidity Events
Most of what determines the tax outcome of a sale is decided before closing, not after. We model gain scenarios, entity consequences, real estate and reinvestment decisions while the deal terms are still open.
By the time a business sale, recapitalization or other liquidity event reaches closing, most of the decisions that determine the tax outcome have already been made: how the deal is structured, what entity is selling, and what happens to the proceeds afterward, which is where capital and CFO strategy picks up. Trying to plan around the tax bill after the purchase agreement is signed leaves very little room to change the outcome. The work has to happen while the deal terms are still open.
Who this is for
This applies to owners selling all or part of a business, taking on a new investor or partner in a way that triggers gain, or otherwise facing a large, one-time liquidity event. It also applies earlier than most owners expect, while a deal is still in negotiation and the structure is still flexible.
- Owners in active discussions with a buyer or investor
- Owners considering a recapitalization or partial sale
- Businesses where real estate, equipment or other assets sit inside the entity being sold
- Owners who expect meaningful proceeds and have not yet planned for where they go
What we model
We build gain scenarios under the deal structures actually on the table, an asset sale versus a stock or equity sale, and how each is taxed differently at the entity and owner level. We look at whether real estate inside the business should be separated from the transaction, including whether a 1031 exchange makes sense for it, what an installment structure or earnout does to the timing of the gain, and how charitable giving or reinvestment strategies might offset part of the liability. The goal is a clear picture of after-tax proceeds under each realistic structure before agreeing to one.
Why the order of decisions matters
Some of the most effective planning here, entity restructuring, charitable structures and reinvestment vehicles, needs lead time to set up correctly, and generally cannot be layered in after a letter of intent is signed. Bringing tax and legal review into the process early, alongside the deal team, is what keeps these options available instead of foreclosed by the time the deal is done.
Where these decisions connect
Deduction and gain treatment depends on individual facts and current law, and should be reviewed with the tax and legal professionals responsible for your return.
Start with the numbers
The first review is free. We will look at your current situation, identify the areas worth modeling, and tell you whether there appears to be a meaningful planning opportunity.