The scenarios below are hypothetical composites drawn from situations that recur in this work. They are written to show the reasoning — what the decision actually turns on — rather than to claim a result. No figure here represents an outcome produced for a client, and nothing on this page is a prediction of what any household should expect.
Married physicians, mid-40s, combined income $850,000, $2.4 million portfolio held at a national wirehouse brokerage.
Paying 1.15% advisory fees plus 0.65% in underlying fund expenses plus $3,200 per year in trading costs. No tax-loss harvesting. No integrated financial plan. The couple spoke to a rotating "team" — never the same person twice.
Consolidated to a single tax-efficient portfolio built around low-cost index and institutional share-class funds. Implemented systematic tax-loss harvesting across all taxable accounts. Built a comprehensive financial plan covering retirement projections, education funding for three children, a disability insurance gap analysis, and updated estate documents.
What the work turns on. Three separate costs were being paid and only one was visible. The advisory fee appeared on a statement; the fund expenses and the trading costs did not. Before anything is restructured, the first job is simply to total what is actually being paid — and then to establish whether moving a position is worth the tax it triggers, which is a question about basis, not about fees.
The figures above describe the position this household started from — not a result produced for them.
Software founder, early 50s, sold his company for $12 million in after-tax proceeds. First time with significant liquid wealth.
Three banks competing for the account, each proposing proprietary products and structured notes. No one had asked about his goals beyond "growth." A significant portion of net worth remained concentrated in a single stock during the transition period.
Designed a 90-day structured unwinding of the concentrated position using tax-aware lot selection to minimize capital gains impact. Built a diversified portfolio anchored to a written financial plan with explicit goals, risk tolerances, and withdrawal assumptions.
Coordinated with estate attorney on trust structure, a gifting strategy for adult children, and generation-skipping provisions to preserve wealth across three generations.
What the work turns on. “Sell everything Monday” and “hold and hope” are both decisions, and both have a cost. The real question is the schedule: which lots, in what order, across how many tax years, and what the household is willing to give up in diversification to defer the bill. That is a conversation about the goals the money has to fund, which is why it comes before the portfolio rather than after it.
The figures above describe the situation and the plan — not a result produced for anyone.
Dual-income couple — a finance executive and an attorney — late 50s, $4.8 million portfolio, relocating from Manhattan to Fort Lauderdale.
Still paying New York state income tax despite spending most of the year in Florida. Prior advisor had never flagged the domicile documentation requirements. No homestead protection filed on the new primary residence.
Conducted a comprehensive residency audit and assembled the documentation required to establish Florida domicile. Filed homestead exemption on the primary residence. Restructured portfolio for Florida-favorable tax treatment and coordinated with the couple's CPA and estate attorney on updated trusts reflecting the new state of residence.
What the work turns on. Domicile is decided by evidence, not by intention or by how many nights were spent where. The states being left audit these moves and the burden of proof sits with the taxpayer, so the work is documentary and behavioral: where the filings originate, where the advisers sit, where the driver's license and the voter registration point, and whether the record tells one story or two.
The figures above describe the situation and published tax rates — not a result produced for anyone.
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Begin ConversationImportant Notice. These scenarios are hypothetical composites for illustrative purposes only. They do not represent any specific client or guarantee of results. Individual outcomes vary based on market conditions, timing, and personal circumstances. Past performance and hypothetical illustrations are not indicative of future results. All investment strategies carry the potential for profit or loss.
Important Disclosures. Wolfson Private Wealth, LLC ("WPW") is an investment adviser registered with the Florida Office of Financial Regulation. Registration does not imply a certain level of skill or training. All investment strategies have the potential for profit or loss. Past performance is not indicative of future results. Diversification does not guarantee a profit or protect against loss.
Information presented on this website is for educational and informational purposes only, does not constitute investment, tax, legal, or accounting advice, and should not be construed as a solicitation, offer, or recommendation to buy or sell any security. Any client scenarios described are hypothetical composites for illustrative purposes only and do not represent any specific client, actual performance, or guarantee of results.
WPW does not offer tax or legal advice. Clients should consult qualified tax and legal professionals regarding their individual circumstances. Assets are custodied at Interactive Brokers LLC, a qualified custodian. WPW is not affiliated with Interactive Brokers LLC. The presence of a link to a third-party website does not imply endorsement.
Florida tax and asset protection commentary represents general information as of the publication date and is subject to change by legislative or regulatory action. WPW encourages all readers to obtain situation-specific counsel. Our complete disclosure brochure (Form ADV Part 2A) is available upon request and on the Investment Adviser Public Disclosure (IAPD) website.