M&A and Liquidity Event Planning

The short version

When your company is acquired or goes public, the decisions that matter most have short windows and no undo button. We coordinate the whole event — how your equity is treated, what lands in which tax year, how much concentration you carry through closing, and what the withholding gap actually is — alongside the CPA and attorney you already have. The work starts before the deal closes, because that is when the levers still move.

This is for you if

Your company has announced a transaction, or you have credible visibility that one is coming
A meaningful share of your net worth is in employer equity you cannot freely sell yet
You have a CPA and an attorney, and neither of them is sequencing the whole picture
You are trying to decide what to do before closing rather than reconstruct it afterward

What we handle

Equity treatment under the deal. Reading the merger agreement's treatment-of-equity provisions alongside your grant documents to establish what actually happens to vested shares, unvested awards, options, and performance shares — assumption, cash-out, or acceleration — and what that means in dollars and in timing.

Section 280G exposure. Modeling your base amount and the 3x safe harbor before closing, when waivers, cutback elections, shareholder votes at private companies, and non-compete valuations are all still available. After closing, they are not.

Double-trigger and change-of-control provisions. Establishing what your acceleration terms actually require, what the "good reason" definition covers, and how that interacts with the role you are offered post-close.

The withholding gap. Employers commonly withhold on supplemental income at a flat statutory rate. If deal income moves you into a higher bracket, the shortfall on a large accelerated amount can run to six figures — payable the following April, on value measured at vest. We size it in advance and decide how it gets funded.

Concentration through closing. Between announcement and close, deals can break on financing, regulatory review, or a shareholder vote. How much single-stock exposure you carry through that window is a real decision, constrained by trading windows and any existing 10b5-1 plan.

Escrow, earnout, and rollover equity. Consideration you do not receive at closing has its own timing, its own risk, and in the case of rollover equity, its own concentration problem in a company you did not choose.

Tax-year sequencing. Charitable timing, deferred compensation elections, option exercise timing, and loss harvesting elsewhere in the portfolio — coordinated around the year the deal income lands rather than each in isolation.

How the work runs

Document intake. Grant agreements, the equity plan, your employment and change-of-control agreements, cost basis by lot, and the insider trading policy. The answers are in these, not in the press release.
Model the event. Full-year tax projection with deal income included, 280G analysis where relevant, and the concentration picture including unvested awards.
Decide and sequence. Which levers apply, in what order, against the trading calendar and the closing timeline.
Execute alongside your CPA and attorney. We do not replace them. We make sure the three views agree with each other.

Questions we hear most often

When should I start?

Before closing, and ideally before announcement if you have visibility. Most of the meaningful levers — withholding, concentration, charitable timing, 280G mitigation, tax-year positioning — close as the deal closes.

I already have a CPA. What's different here?

Your CPA sees the tax year, usually in arrears. Your attorney sees the agreement. Neither is typically modeling what happens to your balance sheet across the whole event and the years after it. That coordination is the work.

What if the deal falls through?

Terms generally revert, which is exactly why concentration between announcement and close deserves a deliberate decision rather than a default.

Do you work with people who are not yet clients elsewhere?

Yes. A liquidity event is one of the most common reasons people engage an adviser for the first time.

What does an engagement look like?

That depends on complexity and what you need. The first conversation is a thirty-minute call to establish whether the fit is there — it is a conversation, not a pitch.

Educational content only. This is not tax, legal, or accounting advice. The treatment of any specific transaction depends on your plan documents, your deal documents, and your own facts.