Selling a business, stock, or real estate triggers capital gains tax. A capital gains tax advisor helps you structure the transaction, time the sale, and apply proven strategies — before you close, not after. Michelet Financial serves clients in all 50 states.
Quick Answer — What Is Capital Gains Tax Planning?
Capital gains tax planning involves strategies to reduce or defer the taxes owed when you sell an asset — a business, stock, real estate, or investment — for more than you paid. A capital gains tax advisor can help business owners and high-income investors time their sales, use tax-loss harvesting, opportunity zones, or installment sales to minimize what goes to the IRS.
Capital Gains Fundamentals
Capital gains tax is the federal — and in most states, state — tax you pay on the profit from selling a capital asset: your business, real estate, stocks, or other investments. The taxable gain is the difference between your sale price and your cost basis (what you originally paid, plus improvements and transaction costs).
At the 20% federal long-term rate plus the 3.8% Net Investment Income Tax, the federal bill on a $1,000,000 gain can exceed $238,000 — before state taxes. Capital gains planning exists to change that number legally before the transaction closes.
Rate Comparison
The single most consequential distinction in capital gains tax is how long you held the asset. Holding for more than 12 months before selling can cut your federal rate nearly in half.
On a $500,000 gain, the difference between short-term and long-term federal treatment is more than $60,000. When timing a sale, an extra few months of holding can be one of the highest-ROI financial decisions you make.
Tax Reduction
These are not aggressive schemes — they are strategies written into the federal tax code and used by the wealthiest investors and business sellers in the country. The difference is having an advisor who applies them before you transact, not after.
The simplest strategy: hold assets more than 12 months before selling. The rate difference between short-term (up to 37%) and long-term (20%) is immediate and substantial. When timing a business sale or investment exit, holding a few additional months can save tens of thousands in federal tax alone — and it requires no complex structuring.
Sell underperforming investments at a loss to offset capital gains from profitable sales. Losses offset gains dollar-for-dollar: $50,000 in realized losses eliminates the tax on $50,000 in gains. Losses in excess of gains can offset up to $3,000 of ordinary income annually, with the remainder carried forward indefinitely. See our full tax-loss harvesting guide.
Reinvesting capital gains into a Qualified Opportunity Zone (QOZ) Fund allows you to defer capital gains tax until 2026 (or an earlier sale of the fund). More significantly, appreciation inside the fund is entirely tax-free after a 10-year hold. For large, one-time gains — business sales, real estate exits — QOZ investments can generate substantial permanent tax elimination.
Instead of receiving the full sale price in year one, spread payments over multiple years. This distributes the taxable gain across multiple tax years, potentially keeping you in lower brackets, avoiding NIIT thresholds, and deferring tax on the gain until cash is actually received. Installment sales require careful structuring to comply with IRS rules — but the deferral benefit can be significant on large transactions.
Transfer appreciated assets into a CRT before the sale. The trust sells the asset without paying capital gains tax, reinvests the full proceeds, and pays you income over a defined period. You receive a partial charitable deduction in the year of the transfer, and the remainder passes to charity at the end of the trust term. Complex, but highly effective for large appreciated assets where the owner wants income and has charitable intent.
How you sell your business can matter as much as what you sell it for. In an asset sale, different assets are taxed at different rates — goodwill often at long-term capital gains rates, equipment subject to depreciation recapture, inventory at ordinary rates. In a stock sale, proceeds are typically all long-term capital gains if you have held your shares more than 12 months. The QSBS exclusion (IRC §1202) can eliminate up to $10M in capital gains entirely for qualifying small business stock held 5+ years. Negotiating the deal structure has direct, permanent tax consequences.
Who We Serve
Capital gains planning is not a filing-season activity. The best strategies require months — often years — of lead time before the taxable event occurs. If any of the following apply to you, you need a capital gains tax advisor now, not in April.
Whether you are 6 months or 5 years from selling, the tax structure of your exit begins today. Entity type, ownership structure, holding period, and deal terms all determine your post-tax proceeds. Michelet Financial models every scenario before you engage a buyer.
Appreciated real estate triggers significant capital gains and depreciation recapture. 1031 exchanges, installment sales, and opportunity zone investments each offer meaningful deferral or elimination options — but all must be structured before closing, not after.
If you hold concentrated stock positions, vested equity, or investment portfolios with significant unrealized gains, proactive capital gains planning determines how much of that appreciation you actually keep.
Stock options, RSU vesting, company sales, and secondary transactions all trigger capital gains. The timing of exercises and sales — relative to your other income — dramatically affects your tax outcome. AMT planning for ISO options is a specialized need that requires a forward-looking strategist.
Our Approach
Brandt Michelet is a Financial Strategist — not a traditional tax preparer or CPA. His background managing financial strategy across hundreds of business units means he approaches capital gains planning the way a CFO does: model the transaction, stress-test the structure, quantify every scenario before any decision is made.
Michelet Financial works with business owners and high-income investors nationwide to:
The goal is not to file the paperwork on what happened. It is to change what happens before the transaction closes.
FAQ
Capital gains tax is one of the largest single expenses business owners face. A well-timed strategy — built before you transact — can save six figures. Book a free consultation and let’s model your options.
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