From a concentrated stock position and a scattered real estate portfolio to a coordinated family plan.

The situation

The family came to us after a liquidity event. One spouse had exited a technology company years earlier and was still holding a large concentrated position in the acquirer's stock, plus a mix of RSUs from a second role. The other spouse ran a small real estate portfolio, four rental properties acquired over fifteen years, self-managed, with no consistent depreciation strategy across them.

They had a wealth advisor at a large firm, an estate attorney they liked, and a CPA who filed a very complicated return every year and never picked up the phone in between. Adult children were starting to ask questions about the family finances and no one had a coherent answer.

What we found

In the first working session we mapped the full balance sheet, pulled three years of returns, and put every asset on one page for the first time. What jumped out:

• Concentrated stock. A significant portion of net worth was sitting in a single public company. No plan for diversification. No conversation about whether any of the original founder shares still qualified for Section 1202 QSBS treatment, or how to sequence sales to manage capital gains rates and net investment income tax.
• RSUs. Vesting was being handled by the employer's default withholding, which was consistently under-withholding at the family's actual marginal rate. Every April produced a large balance due that no one had modeled in advance.
• Real estate. Four properties, all held in personal name. No cost segregation had ever been done. Depreciation schedules were inconsistent. Two of the properties were prime 1031 exchange candidates the family had never considered.
• Charitable giving. They gave meaningful amounts every year by writing checks. No donor-advised fund, no consideration of gifting appreciated stock instead of cash.
• Estate. A revocable trust was in place. No irrevocable structures for the next generation, no annual gifting program, no discussion of the current lifetime exemption window.

What we did

Year 1. Get the picture right and pick the low-hanging fruit. We stood up a proper quarterly planning cadence, coordinated with the wealth advisor and estate attorney so everyone was reading from the same page, and built a multi-year projection of income, deductions, and capital gains.

On the concentrated stock we set up a 10b5-1 style disciplined sale plan and identified a slice of shares that qualified for Section 1202 QSBS exclusion, which materially changed the after-tax outcome on that portion. We funded a donor-advised fund with appreciated stock instead of cash and captured a deduction against a high-income year.

Year 2. Real estate and the next generation. We commissioned cost segregation studies on the two most recently acquired rentals and adjusted depreciation on the portfolio going forward. We structured a 1031 exchange on a property the family wanted to reposition out of. We coordinated with the estate attorney to launch an annual gifting program to the children and, where appropriate, use trust structures to move future appreciation outside the taxable estate.

Year 3. Coordination as the default. Quarterly advisory sessions with the family, with the wealth advisor and estate attorney looped in on a defined cadence. Year-end planning became a working meeting with actual decisions on the table, not a review of what had already happened.

Where they are now

• Concentrated stock exposure reduced on a schedule, with QSBS treatment captured where it applied and charitable giving funded from appreciated shares.
• Real estate portfolio held in a structure the family understands, with depreciation aligned and a 1031 completed to reposition one property.
• A gifting and trust strategy in place that uses the current exemption window intentionally rather than by default.
• Adult children brought into the conversation with a framework to understand it, not a stack of returns.

What we would say to another family in the same seat

A note on scope. We do not manage investments, we do not perform business or real estate valuations, and we do not draft estate documents. What we do is sit at the center of the plan, coordinate the specialists, model the tax consequences of every meaningful decision before it happens, and make sure nothing important falls between the cracks.

If the story on the previous page could be your family, that is what a coordinated advisory relationship looks like. It is not a product. It is a cadence.