Today's Tax Strategy Pulse
New Bill Targets Large Trusts with Annual Withholding Tax
A proposed bill would impose an annual withholding tax on trusts that hold assets exceeding $50 million. The legislation aims to capture revenue from high‑value trusts through this new tax mechanism.
Kiplinger Warns Capital Gains Indexing Could Cut Taxes by $7,000 on $200K Sale
Kiplinger’s Tax Letter says the Trump administration is considering an executive‑action rule to index capital gains to inflation, a move that could reduce tax on a $200,000 asset sale by roughly $7,000. The proposal, if adopted, would shift cost bases upward, offering sizable savings for high‑net‑worth investors and prompting wealth managers to rethink timing and Roth conversion strategies.
5 Tax Planning Moves to Make Due to the One Big Beautiful Bill Act
The One Big Beautiful Bill Act (OBBBA), signed in July 2025, reshapes 2026 tax planning by making lower individual rates permanent, boosting the state and local tax (SALT) deduction cap to $40,000, and adding temporary deductions for tips, overtime, seniors,...
Iowa Overhauls Captive Insurance Rules, Adds Tax Break and Life Reinsurance
Governor Kim Reynolds signed House File 2766 on May 15, revamping Iowa's captive insurance framework with a premium‑tax break for redomesticating captives, a five‑year clawback provision, and a brand‑new life captive reinsurance regime. The changes also lower the capital floor...
Wyoming LLC: Tax‑Smart Crypto Strategy for $50K+ Portfolios
The complete digital asset LLC strategy: 1) Set up Wyoming single-member LLC 2) Transfer crypto before major gains 3) Track and implement suitable deductions 4) Consider insurance policy funding 5) Consider family gifting strategy. Most effective for portfolios currently over...
Executive Order on Cannabis and 280E Proves Empty
It took a while, but I co-authored an article about the recent nothingburger of an executive order about Cannabis and 280E. Read here: https://t.co/CStb3Qwkgu
Tax‑Smart Strategies for Investors with 90% of Net Worth in One Stock
Ben Carlson of Ritholtz Wealth Management says clients are now walking in demanding tax‑aware diversification as 90% of their net worth sits in a single stock. He and other experts highlight custom indexing, tax‑loss harvesting, charitable remainder trusts and 10b5‑1...
Your Client Is Buying a Business. Have They Considered Cost Segregation?
When acquiring businesses with real‑estate components, depreciation can outweigh purchase price in after‑tax cash flow. Cost segregation—an engineering analysis that reclassifies building elements to five‑, seven‑ or 15‑year lives—now often yields an immediate 100% bonus depreciation under Section 168(k) for assets...
The $40,000 Tax Move That Comes After Your 401(k) Hits Its Limit
Affluent investors who have maxed out 401(k) and mega backdoor Roth contributions can still shave taxes by switching a taxable S&P 500 ETF to a direct‑indexed separately managed account. On a $1.2 million sleeve, the strategy typically harvests $30‑$50 k of losses, translating...
Gift Low‑Value Assets to Trust, Preserve Exemption
The lifetime gift tax exemption in 2026 is $15 million per person, $30 million combined for married couples. Gifting assets into a trust while their value is lower preserves more of that exemption for later use. Assets that grow inside...
The NUA Strategy Retiring Executives Use to Cut Taxes on $500,000 of Company Stock in Their 401(k)
A 62‑year‑old Apple executive can avoid a $38,000‑$78,000 tax hit by using the Net Unrealized Appreciation (NUA) rule instead of rolling $500,000 of company stock into an IRA. NUA treats the $80,000 cost basis as ordinary income while the $420,000...
Small Planning Conversations That Lead to Bigger Engagements
In this episode, Kerry Sinnott and guest Jackie Cummings‑Koski highlight five quick, high‑impact strategies CPA financial planners can use to add immediate value for clients. They dive into expanded 529 plan uses—including paying for professional credentials, covering K‑12 expenses, seeding...
Ask an Advisor: We Earn $350K+ and Can't Contribute to a Roth IRA. Can We Still Do Roth Conversions Now?
High‑income earners over the Roth IRA contribution limit can still benefit from Roth conversions. There is no income ceiling on moving funds from traditional IRAs or 401(k)s into a Roth, but the converted amount is taxed as ordinary income in...
Fund Closure Forces UK Investors to Face Up to £14,000 Capital Gains Tax Bill
The Stewart Investors Worldwide Leaders Fund is shutting down, leaving investors with a £60,000 holding and a looming capital gains tax liability of up to £14,000. Experts advise exploring rollovers or professional advice to soften the impact.
TaxPlanIQ Presents Weekly Tax Strategy Hour for Tax Pros
TaxPlanIQ, a tax‑planning platform for advisory‑focused accounting firms, launched a free weekly virtual series called Strategy Hour. The sessions run Wednesdays from noon to 1 p.m. ET starting May 20 and each provides one CPE credit. Each week a specialist presents a...
Internal Revenue Service Publishes Final Rule for “No Tax on Tips” Deduction
The IRS issued its Final Rule for the One Big Beautiful Bill Act’s “no‑tax‑on‑tips” deduction, confirming the list of qualifying occupations and making modest updates. Three new occupations—visual artists, floral designers and gas‑pump attendants—were added, and three existing categories were...