A $210 million exit. Ninety days to act.
The founder of a regional financial services firm received an acquisition offer. Without intervention, the combined federal and state tax burden would have consumed more than half the proceeds. Monolith restructured the transaction before it closed.
A thirty-year business. A ninety-day window.
James Castellan had founded a regional financial services firm in 1993. Over thirty years, he had grown the business to 180 employees and $210 million in enterprise value. He had always assumed he would sell eventually — but the offer arrived before he had done any pre-transaction planning.
The acquirer was a national firm seeking regional market share. The offer was structured as a cash transaction with a ninety-day close. Castellan's M&A attorney had negotiated favorable terms. His CPA had modeled the tax consequences.
The model was accurate. The outcome it described was not acceptable.
More than half the proceeds were going to disappear.
Castellan's basis in the business was approximately $4 million — the original capital he had contributed over the company's early years. The $210 million transaction price represented a $206 million gain.
At the federal long-term capital gains rate of 23.8% (including the net investment income tax) and his state's income tax rate of 9.3%, the combined tax burden on the transaction would have been approximately $68 million — leaving him with approximately $142 million after tax.
He had ninety days. Most pre-transaction planning strategies require significantly more lead time. The question was what could be accomplished within the constraint.
$68 million in combined federal and state tax on a $210 million transaction.
Pre-close restructuring within the available window.
Charitable remainder unitrust (CRUT) contribution
Prior to close, Castellan contributed a portion of his equity interest — representing approximately $42 million in value — to a CRUT. The contribution was made before the transaction closed, establishing a charitable deduction and removing the contributed interest from the capital gains calculation. The CRUT will pay him an annuity for life, with the remainder passing to a donor-advised fund.
Installment sale structure for retained interest
A portion of the transaction was restructured as an installment sale, spreading the gain recognition across multiple tax years and allowing Castellan to manage his effective rate by controlling the timing of income recognition relative to other deductions.
Opportunity Zone reinvestment
A defined portion of the recognized gain was reinvested into a Qualified Opportunity Zone fund within the required 180-day window, deferring that gain until 2026 and potentially reducing it through the step-up in basis provisions.
Dynasty trust establishment
The after-tax proceeds were transferred to a dynasty trust structured to hold assets across multiple generations without triggering additional estate or generation-skipping transfer tax. The trust was established in a jurisdiction with favorable trust law and no state income tax on undistributed trust income.
Thirty years of work. Preserved.
The restructuring increased Castellan's post-tax proceeds from approximately $142 million to approximately $180 million — an increase of $38 million. The combined effective tax rate on the transaction was reduced from approximately 32% to approximately 14%.
The CRUT provides Castellan with a guaranteed income stream for life, funded by the pre-tax value of the contributed interest. The dynasty trust holds the remaining proceeds in a structure designed to preserve wealth across three generations without additional transfer tax.
The engagement was completed in sixty-one days — within the ninety-day window. Castellan's M&A attorney, CPA, and financial advisor were all engaged in the restructuring and remain his primary advisors.
This case study is a composite narrative. Names, industry, and identifying details have been changed to protect client confidentiality. The financial structures and outcomes are representative of actual engagements. Past results do not guarantee future outcomes. The Clearview Group does not provide legal or tax advice. All strategies are implemented in coordination with qualified legal and tax counsel.