Case notes

Short, real examples with the names removed. Each one shows the industry, the rough size, the mistake avoided, and the one thing that would have gone wrong without a CPA and an attorney in the same room.

Exit and structure

Owners and the companies they built

Medical practice · North JerseyEnterprise value ~ $10M

The diagnostic method was worth millions. It was sitting inside the operating practice for free.

Situation: A single-owner specialty practice with a proprietary imaging methodology and a recognized trade name. Any buyer would have priced the whole thing as one business, and the physician's most valuable asset would have gone out the door at the practice multiple.
What we did: Placed the methodology and the trademark into a separate IP holding company, independently valued in the millions on a royalty basis, and licensed it back to the practice. Ownership of the holding company was moved into irrevocable trusts for the family, with the tax return and the trust instruments designed together.
Without both licenses: A license agreement whose royalty rate did not match the valuation, or a valuation the trust attorney never saw, invites recharacterization. The transfer documents, the appraisal and the tax reporting had to agree, and they were written by the same hand.
Result: An asset that can now be licensed, sold separately, or carried past a sale of the practice, outside the physician's taxable estate.

Physician practice · Pre-saleProduct IP carve-out

Selling the practice without selling the thing he invented

Situation: A dermatologist contemplating a sale of his practice had also developed AI-enabled product technology alongside it. Left alone, the buyer's counsel would have swept the technology into the practice assets at no additional price.
What we did: Built a plan to disaggregate the enterprise goodwill of the practice from the physician's personal goodwill and the product IP, move the IP into its own company on licensing rails, and sequence the conversations with the technology partner and the prospective buyer so nothing was conceded before it was priced. Health-care regulatory limits were mapped before the structure was drawn.
Without both licenses: The tax treatment of personal goodwill and the legal separation of the IP are the same question asked two ways. Answer one without the other and either the buyer or the IRS gets the benefit.
Result: A physician who can sell the practice and keep, license or sell the technology on his own terms.

Design and fabrication · $4M revenuePartner separation

Not every exit is a sale to a stranger

Situation: A two-partner company, one U.S. principal and one foreign partner, each at 50%. The principal had carried the business through the pandemic and secured roughly half a million dollars in government funding. The partners' economics no longer matched their contributions, and the foreign partner's filings had never been handled correctly.
What we did: Designed a reorganization: a new corporation owned by the principal, with the legacy company repurposed as a staffing entity. Treated the principal's compensation as guaranteed payments for services, corrected the partnership's capital accounts, and brought the nonresident partner's withholding and international reporting current, with a formal position letter to the partner's counsel.
Without both licenses: The corporate reorganization and the partnership tax treatment had to be one design. A lawyer drawing the new entity without the tax view, or a CPA correcting the returns without the legal separation, would have left the seam wide open.
Result: A clean structure the principal controls, defensible filings, and a documented answer to the departing partner's objections.

Land development · S corporationFinal sale and wind-down

Thirty years of lot sales, and the basis of the last one

Situation: A family S corporation bought a tract in the 1990s, subdivided it, and sold lots over three decades. The final lot sold in 2025. Reporting the gain correctly, and closing the entity cleanly, depended on reconstructing cost basis from records that predated everyone's current software.
What we did: Traced the original acquisition, the development costs and every prior allocation through the historical returns and closing files to establish the basis of the final lot, then reported the sale and planned the wind-down.
Without both licenses: Basis is money at closing. Unsupported basis becomes taxable gain; a corporate dissolution without the tax sequence right becomes a second tax.
Result: A supportable gain, a final return, and an owner who knew the number before the state did.

Family office

Families and the wealth behind the business

Retirement accounts · Eight grandchildrenTrust design

Who controls the payout from the retirement accounts after you are gone

Situation: A couple with substantial IRA and pre-tax plan balances, four adult children and eight grandchildren, and accounts spread across two custodians. Naming the grandchildren directly would have put the timing of taxable distributions in the hands of minors and their parents.
What we did: Drafted a retirement benefits trust designed to receive the accounts, with the trustee controlling the year-by-year liquidation plan and separate shares for each grandchild. Consolidated the accounts at one custodian, prepared the beneficiary designation package and certification of trust, and coordinated with the family's financial advisor so the paperwork matched the plan.
Without both licenses: A trust that is beautifully drafted but named wrong on the custodian's form, or a designation that ignores how the distributions will be taxed, fails at the moment it is needed.
Result: An executed trust, designations that match it, and a written list of what remains to be retitled.

Rental real estate portfolioTax strategy

Whether the rentals are a business, and what that is worth

Situation: A couple building a portfolio of rental properties, with roughly $200,000 of renovation spend before two properties were placed in service, asked whether they qualified as real estate professionals and how their losses would be treated.
What we did: Wrote a research memo on real-estate-professional status, material participation, the rental safe harbor and the aggregation election, then updated it to answer the couple's follow-up questions and recommended making the aggregation election with the current year's return, with the lifecycle trade-offs spelled out. Cost segregation on the renovation spend was evaluated alongside.
Without both licenses: An election made for this year's deduction without the exit in view can cost more when the properties are sold. The memo covered both ends.
Result: A documented position, an election with eyes open, and a plan that survives the eventual sale.

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