Case Study: Business Owner Trust - Tax-Free Exit and Preserved Wealth

A business owner faces a steep capital gains tax bill when selling their private company, threatening decades of equity. They partnered with DeferCapitalGains.ai for a tax-efficient exit, seeking liquidity, diversification, and flexibility.

The Challenge 

Selling would trigger: 
  • Lose a quarter a third or more of proceeds to capital gains taxes.
  • Reduced funds for reinvestment.
  • Limited retirement income and heir's benefits.
The owner sought tax deferral and investment freedom.

The Solution: Business Owner Trust DeferCapitalGains.ai structured a Business Owner Trust:
  • Business Transfer: Company moved business into the trust.
  • Tax-Free Sale: Trust sold the business, avoiding constructive receipt.
  • Diversified Assets: Proceeds invested in a diversified portfolio.
  • Tailored Income: Payments matched retirement goals and risk.
  • Tax Deferral: Gains taxed only on distributions, optimizing brackets.
The Results
  • No Upfront Taxes: 100% of gains deferred.
  • Full Reinvestment: Entire proceeds fueled growth.
  • Diversified Wealth: Seamless shift to a balanced portfolio.
  • Reliable Income: Steady cash flow for retirement.
  • Heir Advantages: Potential basis step up and minimizing taxes.
Why It Matters

The Business Owner Trust turned a taxable sale into a wealth-building engine, safeguarding equity, enhancing retirement income, and maximizing flexibility for the owner and their heirs.

Exit Smarter, Tax-Free. Schedule a confidential consultation at DeferCapitalGains.ai.
November 20, 2025
A senior executive held a highly appreciated, concentrated stock position, facing portfolio risk and a significant tax burden. Selling would trigger substantial capital gains taxes, reducing reinvestment capital. They engaged DeferCapitalGains.ai for a tax-efficient, flexible diversification strategy. The Challenge Liquidating the stock would trigger: Losing a quarter a third or more in capital gains taxes. Reduced capital for reinvestment. Persistent single stock risk. The executive sought immediate diversification without significant tax implications. The Solution: Stock Diversification Trust DeferCapitalGains.ai implemented a Stock Diversification Trust: Stock Transfer: Executive moved shares into the trust. Tax-Free Liquidation: Trust sold the stock, avoiding constructive receipt. Diversified Reinvestment: Proceeds funded a balanced portfolio. Tailored Income: Payments aligned with risk tolerance and goals. Tax Deferral: Gains taxed only as payments were received, optimizing brackets. The Results Full Tax Deferral: No capital gains tax at sale. 100% Reinvestment: Entire stock value invested, boosting compounding. Diversified Portfolio: Reduced risk vs. single stock. Lower Volatility: Stabilized wealth. Estate Planning: Potential basis step-up for heirs, minimizing taxes. Why It Matters The Stock Diversification Trust converted a risky, taxable stock position into a diversified, tax-advantaged portfolio, preserving wealth, enhancing long-term income, and optimizing for the executive and their heirs. Unlock Tax-Free Diversification. Schedule a confidential consultation at DeferCapitalGains.ai .
November 20, 2025
A senior executive held a highly appreciated, concentrated stock position, facing portfolio risk and a significant tax burden. Selling would trigger substantial capital gains taxes, reducing reinvestment capital. They engaged DeferCapitalGains.ai for a tax-efficient, flexible diversification strategy. The Challenge Liquidating the stock would trigger: Losing a quarter a third or more in capital gains taxes. Reduced capital for reinvestment. Persistent single stock risk. The executive sought immediate diversification without a large tax hit. The Solution: Stock Diversification Trust DeferCapitalGains.ai implemented a Stock Diversification Trust: Stock Transfer: Executive moved shares into the trust. Tax-Free Liquidation: Trust sold the stock, avoiding constructive receipt. Diversified Reinvestment: Proceeds funded a balanced portfolio. Tailored Income: Payments aligned with risk tolerance and goals. Tax Deferral: Gains taxed only as payments were received, optimizing brackets. The Results Full Tax Deferral: No capital gains tax at sale. 100% Reinvestment: Entire stock value invested, boosting compounding. Diversified Portfolio: Reduced risk vs. single stock. Lower Volatility: Stabilized wealth. Estate Planning: Potential basis step-up for heirs, minimizing taxes. Why It Matters The Stock Diversification Trust converted a risky, taxable stock position into a diversified, tax-advantaged portfolio, preserving wealth, enhancing long-term income, and optimizing for the executive and their heirs. Unlock Tax-Free Diversification. Schedule a confidential consultation at DeferCapitalGains.ai .
November 20, 2025
A real estate investor faced a significant tax burden when selling a highly appreciated property. Seeking liquidity, flexibility, and tax deferral beyond a 1031 exchange, they turned to DeferCapitalGains.ai for an innovative solution. The Challenge Selling the property would trigger taxes on any gains. The investor needed: Immediate liquidity without 1031 deadlines (45/180 days). Diversification beyond real estate. Legal capital gains tax deferral. Greater control than traditional exchanges. The Solution: Real Estate Shelter Trust DeferCapitalGains.ai structured a Real Estate Shelter Trust to defer taxes and optimize wealth: Property Transfer: Investor moved the property into the trust. Tax-Free Sale: Trust sold the property, avoiding constructive receipt. Diversified Reinvestment: Proceeds funded a tailored portfolio (stocks, bonds, etc.), unrestricted by real estate. Flexible Income: Investors received payments based on risk tolerance and goals. Tax Deferral: Gains taxed only on distributions, optimizing brackets. The Results Full Tax Deferral: No upfront capital gains tax at sale. 100% Reinvestment: Entire proceeds reinvested, maximizing growth. No Deadlines: Freedom from 1031 restrictions. Diversified Portfolio: Enhanced returns beyond real estate. Tax Smoothing: Payments spread over years, reducing tax rates. Estate Planning: Potential basis step-up for heirs, minimizing future taxes. Why It Matters The Real Estate Shelter Trust converted a taxable event into a strategic wealth-building opportunity, preserving capital and boosting long-term income through diversified, tax-advantaged growth. Protect Your Gains. Schedule a confidential consultation at DeferCapitalGains.ai to explore tax-efficient solutions.