Case Study
entrepreneur save income and estate taxes
while addressing his philanthropic life goals.
Subject
Concentrated position in an early-stage private growth company
(~92MM 409A valuation).
Objectives
- Tax-efficient diversification and de-risking of the portfolio
- Provide financial security for immediate and extended family
- Establish a structured, lasting charitable giving program
Process
- LTax Team: analyzed the current tax position and forecast outcomes across liquidation scenarios and proposed IRS code changes
- Wealth Planning Team: compiled all personal and financial data into a comprehensive baseline plan, the foundation for every strategy decision
- Estate & Trust Team: designed a multigenerational estate plan to preserve family values and mitigate estate tax
Strategy
- Applied Section 1202 QSBS exemption to reduce capital gains
- Stacked the exemption via multiple irrevocable family trusts
- Established a Donor Advised Fund, with a path to a private foundation
- Elected state pass-through entity tax (PTET) to reduce federal business income
- Assessed Section 1045 rollover of gain into another QSBS company
- Modeled relocation from a high-tax state with no Section 1202 conformity
Results
Client has structure and process around decision-making for exercised options and remaining ISOs. Funding of retirement and financial plan has been initiated. Portfolio risk has been significantly reduced.
Estimated tax savings: $437,179.00
LTax and Advanced Wealth Planning delivered a specific, actionable plan covering diversification, family security and philanthropy, combining QSBS stacking, a PTET election and a coordinated estate and charitable structure.
Potential estate and income tax savings: $22,319,485
LTax is a boutique tax firm emphasizing personalization, communication, and
initiative-taking responsiveness.
We take a consulting approach to tax preparation and planning, ensuring regular client communication and a personalized understanding of our clients’ needs. We tirelessly research tax mitigation strategies and develop actionable recommendations for the benefit of our clients.
Adam Raschke, JD
Director, Tax Practice Lead
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