The Challenge: Expanding Beyond the Basics
Laura had already taken the foundational steps: maxing out 401(k) contributions and conducting Roth conversions. The challenge now was to identify opportunities that went beyond “check-the-box” retirement planning and find advanced strategies to reduce her W-2 tax burden, diversify her concentrated stock positions, and create long-term flexibility for her family.
Gelt’s Strategic Approach: Layered Planning Across Asset Classes
Retirement Planning
- Recommended deferring Roth conversions to years with lower taxable income, preventing unnecessary bracket creep.
Investment Diversification
- Introduced the concept of an exchange fund, enabling Laura to diversify her concentrated stock position without triggering capital gains.
- Reviewed the potential use of the investment interest deduction to expand mortgage interest benefits beyond the $750K cap.
Real Estate Opportunities
- Explored how short-term rentals, structured with material participation, could generate active losses to offset W-2 income.
- Identified the benefit of cost segregation studies to accelerate depreciation and front-load deductions.
- Highlighted the role of 1031 exchanges to defer capital gains on real estate sales by reinvesting into new properties.
Charitable & Other Deductions
- Recommended donating appreciated stock via a Donor-Advised Fund (DAF) to avoid capital gains while achieving charitable goals.
- Reinforced the value of non-cash donations up to $5,000 without appraisal (with receipts).
- Flagged medical expenses exceeding 7.5% of AGI as a potential deduction when itemizing.
Results & Implementation
With Gelt’s guidance, Laura is now pursuing several parallel strategies:
- Researching exchange fund opportunities to diversify stock holdings without incurring gains.
- Exploring mortgage and investment interest deduction structures to expand tax efficiency.
- Setting up 529 plans for each child to allow for future Roth IRA conversion benefits.
- Preparing to use charitable donations of appreciated stock for upcoming giving.
- Reviewing potential short-term rental opportunities for loss generation and accelerated depreciation.
Conclusion: Building Layers of Tax Advantage
Laura had already mastered the basics of retirement planning, but working with Gelt expanded her perspective on how to use tax strategy across her entire financial picture. By layering retirement, investment, real estate, and charitable approaches, Laura is positioned not only to reduce her current tax burden but also to create long-term flexibility for her family.
Gelt showed me how much more I could do beyond maxing out my 401(k). From real estate strategies to smarter charitable giving, they’re helping me think bigger about tax efficiency and together we found about $30,000 in annual tax savings.
— Laura, New York, NY
Disclaimer: This case study is based on a real client engagement. Certain names, locations, and identifying details have been changed to protect client confidentiality. The challenges, strategies, and outcomes described reflect actual facts. Show more
This material is provided for informational and educational purposes only. It does not constitute, and should not be relied upon as, tax, legal, or accounting advice. Each individual’s circumstances are unique, and readers should consult their own qualified professional advisors before making any decisions.To comply with U.S. Treasury Department regulations (Circular 230), we inform you that any tax information contained in this communication is not intended or written to be used, and cannot be used, for the purpose of (i) avoiding penalties under the Internal Revenue Code, or (ii) promoting, marketing, or recommending to another party any transaction or matter addressed herein.This material is provided for informational and educational purposes only. It does not constitute, and should not be relied upon as, tax, legal, or accounting advice. Each individual’s circumstances are unique, and readers should consult their own qualified professional advisors before making any decisions.To comply with U.S. Treasury Department regulations (Circular 230), we inform you that any tax information contained in this communication is not intended or written to be used, and cannot be used, for the purpose of (i) avoiding penalties under the Internal Revenue Code, or (ii) promoting, marketing, or recommending to another party any transaction or matter addressed herein.
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