When theft gets taxing with Bob Keebler
AICPA Personal Financial Planning (PFP)
Release Date: 04/04/2025
Latest tax proposals: Real-time tax and financial planning conversations
AICPA Personal Financial Planning (PFP)
In this special crossover episode between the AICPA’s Tax Section Odyssey and PFP Section podcasts, April Walker is joined by Bob Keebler and Mark Gallegos to break down the fast-moving tax legislation landscape. They walk through key provisions in both the House’s “One Big Beautiful Bill Act” and the Senate’s proposal, sharing what matters most for client conversations right now. Topics include: Timing and reconciliation process in Congress Section 199A and SALT cap updates PTET deduction differences and planning impact Section 174 R&D expensing changes Bonus depreciation and...
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AICPA Personal Financial Planning (PFP)
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AICPA Personal Financial Planning (PFP)
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AICPA Personal Financial Planning (PFP)
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AICPA Personal Financial Planning (PFP)
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AICPA Personal Financial Planning (PFP)
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When theft gets taxing with Bob Keebler
AICPA Personal Financial Planning (PFP)
In this episode, Cary Sinnett is joined by renowned CPA and tax expert Bob Keebler to unpack the complexities of theft and casualty loss deductions under IRC Section 165. From pig butchering scams to IRA fraud and Ponzi schemes, this episode dives deep into the kinds of losses the IRS will—and won’t—let you deduct, what qualifies as a profit motive, and how financial planners can guide their clients through one of the most emotionally and financially painful tax situations. Five Key Insights for CPA Financial Planners: Profit Motive Determines Deductibility To qualify under Section...
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AICPA Personal Financial Planning (PFP)
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AICPA Personal Financial Planning (PFP)
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Estate Planning & Portability
AICPA Personal Financial Planning (PFP)
In this episode of the AICPA Personal Financial Planning Podcast, Cary Sinnett welcomes Bob Keebler, a nationally recognized expert in estate and tax planning. Together, they break down the critical topic of portability in estate planning—what it is, how it works, and why it matters for both financial planners and clients. Key Insights: Portability: Use It or Lose It – If you don't elect portability within the required time frame, the deceased spouse’s unused estate tax exemption is lost forever. Deadlines Matter – The DSUE must be filed within 9 months of death, but an...
info_outlineIn this episode, Cary Sinnett is joined by renowned CPA and tax expert Bob Keebler to unpack the complexities of theft and casualty loss deductions under IRC Section 165. From pig butchering scams to IRA fraud and Ponzi schemes, this episode dives deep into the kinds of losses the IRS will—and won’t—let you deduct, what qualifies as a profit motive, and how financial planners can guide their clients through one of the most emotionally and financially painful tax situations.
Five Key Insights for CPA Financial Planners:
- Profit Motive Determines Deductibility
To qualify under Section 165(c)(2), a theft or loss must stem from a transaction entered into for profit. Losses from romantic or emotional scams—where no profit motive exists—do not qualify. - Five Scam Archetypes to Know
A recent IRS CCA outlined five fraud scenarios:- Compromised account scams
- Pig butchering (crypto fraud)
- Phishing and impersonation
- Romance scams
- Kidnapping/extortion schemes
Only the first three had profit motives and were deductible.
- The IRA Trap: The Tax Hit Before the Scam
If a client is duped into withdrawing funds from an IRA and then loses the money to a scam, they face a double blow—taxable income and no deductible loss. CPA advisors must flag this risk early. - Documentation Is Critical for IRS Support
To substantiate a theft loss, clients need:- Bank records (e.g., wire transfers)
- Law enforcement reports
- A clear, detailed paper trail showing the loss and the attempt to recover funds
Directing the IRS to the assigned FBI agent can strengthen the claim.
- Mitigation and Planning: Protecting Vulnerable Clients
Encourage older or high-net-worth clients to follow a “1–2% rule” on risky investments. Foster opens dialogue with family members and advisors to prevent fraud and ensure support if it occurs.
Access resources related to this podcast: Note: If you’re using a podcast app that does not hyperlink to the resources, visit Libsyn (PFP) to access show notes with direct links.
- IRC Section 165
- IRS CCA 2025-101015 (the ruling discussed)
- Revenue Procedure 2009-20 (Ponzi Scheme Safe Harbor)
- AICPA PFP Section
- Guiding your clients who are financial caregivers
- Scam Tracker Risk Report
This episode is brought to you by the AICPA’s Personal Financial Planning Section, the premier provider of information, tools, advocacy, and guidance for professionals who specialize in providing tax, estate, retirement, risk management and investment planning advice. Also, by the CPA/PFS credential program, which allows CPAs to demonstrate competence and confidence in providing these services to their clients. Visit us online to join our community, gain access to valuable member-only benefits or learn about our PFP certificate program.
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