Apply for a free educational briefing. We will map your 180-day window, explain which slice of your gain may qualify for deferral (your CPA confirms), and give you the questions to ask anyone who wants your capital, including us. Nothing is for sale on this call.
The day your deal closed, a federal clock started running. Inside that window, the law allows a seller to reinvest the capital-gain portion of their proceeds and defer the tax on that portion. Outside the window, the option is gone. No extensions, no appeals, no "we didn't know."
This is not a loophole. It is Section 1400Z-2 of the Internal Revenue Code, passed in 2017 and made permanent by Congress. Institutional investors have used it since day one. The person selling an HVAC company or a machine shop has usually never heard of it.
Whose job was it to tell you? The M&A advisor closes the deal. The attorney papers it. The CPA reports the sale after the fact. The wealth manager shows up after the decisions have hardened. The window sits in the seam between all of them. That seam is what we work on.
Only the capital-gain slice of your proceeds qualifies. Not the whole wire. If you sold assets, depreciation recapture, consulting payments, and covenants are ordinary income and do not qualify. Sometimes the eligible slice is most of the deal. Sometimes it is smaller than you expect. Your CPA confirms which slice qualifies, and that confirmation is step one of any serious plan.
Anyone who assumes your entire check is eligible has either not read the statute or is hoping you haven't.
Ask your CPA for the proceeds breakdown: capital gain, recapture, ordinary items, by entity. This one document tells you whether the window matters to you.
What deferral does and does not do. How funds are structured, what fees look like, who owns the assets, and the questions to fire at anyone who wants your capital.
Documents, diligence, and wires take longer than people expect, and day 180 does not move. Arrive at week 24 undecided and you make a rushed decision or none.
Education cuts both ways, so here are the limits. Deferral is not forgiveness: the deferred tax comes due. The longer-term benefits require a ten-year hold in illiquid investments that carry real risk, including loss. A tax benefit attached to a bad investment is still a bad investment. And sometimes the right answer, after real analysis, is to pay the tax and stay flexible. A seller who reaches that conclusion deliberately has still done better than one who never knew there was a decision to make.
The Seller's Tax Playbook. The 180-day rules, the capital-gain-slice breakdown to request from your CPA, the timing choices for flow-through entities, and the ten diligence questions, in plain English. Included with your briefing.
An educational briefing. A short call to map your specific window and timeline. Nothing is for sale on this call. Your CPA is welcome, and we mean that: the best briefings include them.