Learn more about capital gains planning and how the Tax Legacy Compass™ program can help you preserve your wealth.
Strategy comparisons in plain English
Most people are shown one strategy first—then everything gets built around that one tool. Tax Legacy Compass™ (TLC) helps you compare the major paths side-by-side, so your final plan fits your goals for taxes, income, flexibility, and family fairness.
Best for:
Real estate investors who want to defer taxes by reinvesting in similar property. Works well if you want to stay in real estate and can meet strict timelines (45 days to identify, 180 days to close).
Watch-outs:
You must buy “like-kind” property of equal or greater value. You’re still in real estate management. Tax is deferred, not eliminated—eventually you or your heirs may face the bill. Doesn’t help if you want liquidity or income now.
The TLC difference:
TLC helps you compare 1031 with income-generating or legacy strategies. If a 1031 makes sense, we coordinate with your team. If you want income or a charitable component, we show alternatives that might fit better.
Considering a 1031 but want to explore income or legacy options?
Best for:
Investors who want passive real estate exposure without active management. Often used as a 1031 replacement property when you don’t want to buy another building yourself.
Watch-outs:
You give up control—DST sponsor makes all decisions. Illiquid (hard to sell your share). Fees can be high. Still real estate risk. Tax deferral only; doesn’t create immediate income flexibility or legacy planning.
The TLC difference:
TLC evaluates whether passive real estate fits your goals or if a strategy focused on income, tax savings, and legacy makes more sense. We help you weigh liquidity, control, and family planning alongside tax deferral.
Want to compare DST with strategies that offer more control and income?
Best for:
People who want to support charity, eliminate capital gains tax on the sale, and receive income for life or a set term. Great if philanthropy is a priority and you don’t need to leave the full asset value to heirs.
Watch-outs:
Irrevocable—once assets go in, you can’t change your mind. Remainder goes to charity, not your family. Complex to set up and administer. Income is taxable. Not ideal if leaving wealth to heirs is your main goal.
The TLC difference:
TLC helps you model CRT scenarios and compare them with strategies that balance charity, family legacy, and income. We show how to maximize tax savings while honoring both charitable and family goals.
Want to see how a CRT compares to strategies that benefit both charity and family?
Best for:
Charitable giving with flexibility. You get an immediate tax deduction, avoid capital gains on donated assets, and recommend grants to charities over time. Simpler than a private foundation.
Watch-outs:
Contributions are irrevocable—money is committed to charity. Doesn’t provide income to you. Doesn’t help with legacy to heirs. Best as part of a broader plan, not a standalone capital gains solution.
The TLC difference:
TLC incorporates DAF into a comprehensive plan. If you want charitable impact plus income and family legacy, we show how to layer strategies so you achieve all three goals, not just one.
Interested in charitable giving as part of a bigger income and legacy plan?
Best for:
People who don’t need to sell now and want to pass assets to heirs with a “stepped-up” basis, eliminating capital gains tax for the next generation.
Watch-outs:
You stay invested in the asset (market risk, management burden). No liquidity or income now. Estate tax may apply if your estate is large. Requires you to hold until death—what if you need funds sooner?
The TLC difference:
TLC helps you decide: hold and hope, or act now to create income, reduce risk, and plan legacy on your terms. We model both paths so you can see the trade-offs clearly.
Wondering if holding until death is your best move, or if there’s a better plan?
Best for:
People who value simplicity and want to move on quickly. If the tax bill is manageable and you don’t want complexity, paying the tax and reinvesting net proceeds can make sense.
Watch-outs:
You lose a large chunk to taxes—often 20-40% of your gain. That’s money that could have generated income, funded legacy, or supported charity. Once paid, it’s gone.
The TLC difference:
TLC shows you what you’re giving up by paying the tax. We model alternatives that could save hundreds of thousands (or more) and create income or legacy value. Then you decide if simplicity is worth the cost.
Curious how much you could save and gain by exploring alternatives before paying the tax?
Best for:
People who trust their existing advisors to handle everything. CPAs and attorneys are essential—but most focus on compliance and legal structure, not proactive capital gains strategy design.
Watch-outs:
CPAs typically prepare returns and react to what you’ve done. Attorneys draft documents but may not specialize in advanced planning. You might miss strategies they don’t commonly use or aren’t trained in.
The TLC difference:
TLC works with your CPA and attorney, not instead of them. We bring specialized capital gains and legacy planning expertise, then coordinate implementation with your trusted advisors. Best of both worlds.
Want a specialist to work alongside your CPA and attorney to maximize your outcome?
Tax Legacy Compass™ is educational and planning-focused. We work alongside your tax and legal professionals to help you compare strategies and coordinate implementation.
Educational information only. Not tax or legal advice.
Get answers to common questions about the Tax Legacy Compass™ program and capital gains planning.
Capital gains tax is a tax on the profit realized from the sale of an asset. When you sell an asset for more than you paid for it, the difference is considered a capital gain and is subject to taxation. Long-term capital gains (assets held for more than one year) are typically taxed at lower rates than short-term gains.
The amount you can save varies significantly based on your specific situation, the type of asset, your tax bracket, and the strategies employed. In many cases, clients can defer, reduce, or eliminate hundreds of thousands to millions of dollars in capital gains taxes through proper planning. During your discovery call, we’ll provide a preliminary assessment of potential savings.
A Charitable Remainder Trust is a tax-exempt irrevocable trust designed to reduce taxable income. You transfer appreciated assets into the trust, which then sells them without paying capital gains tax. The trust pays you (or other beneficiaries) income for a specified period, and the remaining assets go to your chosen charity. This strategy can eliminate immediate capital gains tax while providing income and supporting causes you care about.
A 1031 exchange (named after Section 1031 of the IRS code) allows you to defer capital gains taxes when selling investment or business property by reinvesting the proceeds into similar “like-kind” property. This strategy is commonly used in real estate but can apply to other business assets. Strict rules and timelines must be followed to qualify.
The timeline varies based on your situation and the complexity of the strategies involved. Initial discovery and planning typically takes 2-4 weeks. Implementation can range from a few weeks to several months, depending on the strategies employed and coordination with other advisors. We work efficiently while ensuring every detail is handled correctly.
No! In fact, it’s best to engage with us before you sell. Pre-sale planning provides the most flexibility and opportunity for tax savings. However, we can also help if you’re in the middle of a transaction or have recently completed a sale, though options may be more limited.
Absolutely not. We work collaboratively with your existing CPA, attorney, financial advisor, and other professionals. Our role is to provide specialized expertise in capital gains planning and legacy design that complements their services. We believe the best outcomes come from a coordinated team approach.
We work with clients selling a wide range of highly appreciated assets, including: businesses and professional practices, commercial and investment real estate, land holdings, concentrated stock positions, investment portfolios, and other significant assets with substantial capital gains exposure.
Our fees are customized based on the complexity of your situation and the value we provide. We typically work on a project basis or percentage of tax savings. During your discovery call, we’ll discuss your situation and provide transparent pricing. Many clients find that our fees are a small fraction of the taxes they save.
While we often work with high-net-worth individuals, the Tax Legacy Compass™ program is for anyone facing significant capital gains from the sale of appreciated assets. If you’re looking at a six-figure or larger tax bill, our services can likely provide substantial value. The discovery call is complimentary, so there’s no risk in exploring whether we’re a good fit.
We’re continuously developing new guides, articles, and tools to help you navigate capital gains planning. Check back regularly for updates, or schedule a discovery call to get personalized guidance now.
