The Short Answer19th Hole Financial uses advanced tax mitigation strategies for the largest tax events in a high earner's life: selling a business, real estate or concentrated stock, and an estate above the federal exemption. Each plan is built from your own numbers and designed with your CPA and attorney before anything is sold, signed or filed.
What Are Advanced Tax Mitigation Strategies?
Planning for the tax events too large for ordinary year-end moves: the sale of a business, a building or a concentrated stock position, and an estate above the federal exemption. These events usually happen once, so the planning starts before the sale or transfer, while the timing and structure are still open. Tyler models the tax on your actual numbers, lays the options side by side, and coordinates the plan with your CPA and attorney. The details are specific to each client.
What Does Selling An Appreciated Asset Cost In 2026?
For a Californian, the tax on a large gain stacks three layers:
- Federal capital gains: 20% on long-term gains once taxable income passes $613,700 for married couples filing jointly ($545,500 single).
- Net investment income tax: another 3.8% once modified adjusted gross income passes $250,000 joint ($200,000 single). Those thresholds are not indexed for inflation.
- California: capital gains are taxed as ordinary income, at up to 12.3% plus a 1% surcharge on taxable income over $1 million.
Where each stated top rate fully applies, 23.8% federal plus 13.3% California adds up to 37.1%, or about $1.86 million on a $5 million gain. The rate on a particular sale depends on taxable income, net investment income and the character of the gain, which is why the sale and the estate are modeled together.
How Do These Strategies Fit Estate Planning?
In 2026 each person can pass $15 million free of federal estate tax, and that amount is indexed for inflation from 2027. Amounts above it are taxed at up to 40%. California stopped requiring estate tax returns for deaths on or after January 1, 2005, so for Californians the federal estate tax is the one to plan around. Your estate attorney drafts the documents, and Tyler coordinates the plan with them and your CPA. See your own estate tax exposure.
Who Are Advanced Tax Mitigation Strategies Right For?
- You hold a highly appreciated asset such as a business interest, real estate or concentrated stock
- You expect a large sale, a liquidity event or an unusually high-income year
- Your estate is near or above the federal exemption
- You want the capital gains and the estate planned at the same time
How Does Tyler Work With Your CPA And Attorney?
Your CPA and attorney keep their seats. Tyler models the options and briefs them on every move before anything is filed or signed, and every decision stays yours.
What Do Ventura County Business Owners Ask Before A Sale?
In the Department of Labor's 2024 filings, at least 115 employers in Ventura County cities sponsored a small defined benefit or cash balance plan: 28 in professional services, 11 in construction and contracting and 10 in wholesale distribution, among other industries. Each of those industries holds different assets, such as client relationships, equipment, inventory or real estate, and the mix of assets in a sale is a question for your CPA and attorney. The tax layers above apply to the gain. Where each stated top marginal rate fully applies, their arithmetic sum is 37.1%, and the rate on a particular sale depends on taxable income, net investment income and the character of the gain.
Planning starts before the sale terms are set, with your CPA and attorney in the loop, on Zoom or in person around Ventura County. Ventura County planning covers how a sale fits local owners.
Common Questions
What is tax mitigation?
Tax mitigation means lowering what you owe through choices the tax code already offers: when income is recognized, which account or entity holds an asset, and how an asset is sold or passed on. It is planned in advance and reviewed with your CPA.
When should I start planning a business or real estate sale?
Before the sale terms are set, ideally months ahead, so your CPA and attorney can still shape how the deal is structured and when it closes.
Does California tax capital gains differently?
Yes. California taxes capital gains as ordinary income, at up to 12.3% plus a 1% surcharge on taxable income over $1 million, on top of federal capital gains tax and, where it applies, the 3.8% net investment income tax.
