The Dental Family Office: Advanced Strategies for $25M+

Complexity is the tax on success

At $25M+, the challenge is rarely a single decision — it’s that dozens of moving parts (entities, accounts, properties, tax situations, advisors) grew up separately and no longer point the same direction. A family office sits above all of it: one team, one strategy, one long view, coordinating your CPA, estate attorney, and other specialists around a single plan.

What a family office coordinates

• Investment oversight integrated with tax and estate considerations
• Advanced tax planning across multiple entities and a liquidity event
• Estate and legacy planning, including trusts and wealth-transfer strategy
• Risk management, philanthropy, and preparing the rising generation
• A single point of contact who understands the whole picture

Case study: buy, borrow, die on a $52M portfolio

A hypothetical dentist-entrepreneur has sold a group of practices and holds a $52,000,000 diversified brokerage account with a low cost basis. They need $1,000,000 per year to fund their lifestyle. The question: how do they access cash tax-efficiently without dismantling the portfolio?

The problem with selling

Selling $1,000,000 of highly appreciated stock could realize roughly $1,000,000 of long-term capital gain. At a combined federal long-term capital-gains and net-investment-income tax rate of about 23.8% — before any state tax — that’s roughly $238,000 of tax to access $1,000,000. Repeated every year, selling steadily erodes the portfolio and triggers a recurring tax bill.

The buy-borrow-die approach

Instead of selling, the investor borrows against the portfolio through a securities-backed line of credit, drawing the $1,000,000 they need. Because a loan is not a taxable event, they access the cash with $0 capital-gains tax. The portfolio stays invested and keeps compounding. The only cost is interest on the amount actually drawn.

Even after five years of drawing $1,000,000 annually and accruing interest, the portfolio has grown from $52M toward roughly $73M, the loan remains a single-digit percentage of the assets backing it, and net worth has climbed. The investor funded $5,000,000 of spending while paying no capital-gains tax on it.

The “die” step

At death, the appreciated assets generally receive a step-up in cost basis to their current value, and the outstanding loan is repaid from the estate. The capital gains that were deferred for years can be effectively erased for the heirs — completing the “buy, borrow, die” arc. Estate-tax exposure is addressed separately through the estate plan (for example, with trusts or an ILIT for large estates).

Important disclosures

This case study is hypothetical and for education only. It is not a client, a projection, a recommendation, or a guarantee of any result. Figures are illustrative and simplified; actual returns, interest rates, taxes, and outcomes vary and can result in loss. Borrowing against investments involves significant risk, including forced liquidation. Securities-backed lending is provided by third parties. Nothing here is individualized investment, tax, or legal advice — strategies like this must be evaluated and implemented with your CPA, a tax/estate attorney, and your financial advisor for your specific situation.