At the Money• Apr 15, 2026• 16:30Interview

At The Money: Tax Day Special | At the Money

From At the Money

Bill Artseronian•Director of Tax Services at Ritholtz Wealth Management

Executive Summary

The episode provides a comprehensive guide to year-end tax planning for 2025, focusing on strategies for high-income individuals and business owners.
Key topics include optimizing charitable giving through bunching and donor-advised funds, maximizing retirement account contributions, and strategic timing of capital gains and losses.
It highlights significant recent and upcoming changes in tax law, including the increased SALT deduction cap (with phase-outs) and new limitations on charitable deductions starting next year.
The discussion emphasizes a proactive, year-round approach to tax management, integrating it deeply with overall financial and generational wealth planning.

10 quotes

Concerns Raised

Investors misunderstanding the difference between tax deferral and tax avoidance, leading to future tax liabilities.
New tax laws include income phase-outs for benefits like the increased SALT deduction, meaning not all high-earners will benefit.
Upcoming changes in 2026 will introduce a floor on charitable deductions and limit their value for the highest earners.
Failing to meet specific requirements, such as wage levels for the QBI deduction, can lead to the complete loss of significant tax benefits.

Opportunities Identified

Utilizing bunching strategies and donor-advised funds to maximize charitable deductions, especially before new limitations take effect.
Leveraging the increased $40,000 SALT deduction for those whose income falls below the new phase-out thresholds.
Employing continuous tax-loss harvesting through direct indexing to offset capital gains throughout the year.
Maximizing retirement savings through vehicles like the mega backdoor Roth 401(k) and HSAs.

Key Themes

Strategic Charitable Giving

The episode details methods for maximizing the tax efficiency of charitable donations. This includes bunching several years of contributions into a single year to exceed the standard deduction and using donor-advised funds (DAFs) to time the deduction while maintaining a steady stream of giving.

With higher standard deductions and new floors on charitable gifts coming, understanding these strategies is crucial for philanthropically-minded individuals to ensure their contributions provide a tax benefit.

Navigating Evolving Tax Legislation

The conversation centers on recent tax law changes, particularly the increase of the State and Local Tax (SALT) deduction cap to $40,000 and its income-based phase-outs. It also looks ahead to 2026 changes, such as a new floor for deductible charitable gifts and limits on itemized deductions for top earners.

Tax laws are dynamic, and staying ahead of these changes allows taxpayers to accelerate deductions into more favorable years and avoid being caught off guard by new limitations.

Proactive Capital Gains Management

The discussion advocates for a continuous, thoughtful approach to managing investment gains and losses, rather than a last-minute December activity. Strategies include deferring Q4 gains into the next year to allow more time for tax-loss harvesting and employing state-specific tactics like a "gains harvest" in states like New Jersey that disallow loss carryforwards.

A year-round strategy for managing capital gains, often enabled by tools like direct indexing, can significantly reduce an investor's annual tax liability and improve after-tax returns.

Optimizing Tax-Advantaged Accounts

The episode covers maximizing contributions to accounts like 401(k)s, IRAs, and Health Savings Accounts (HSAs). It highlights advanced strategies like the mega backdoor Roth 401(k) and notes a key change in 2026 requiring catch-up contributions for those over 50 to be made on a Roth (after-tax) basis.

These accounts are powerful tools for wealth accumulation, and understanding their contribution limits, rules, and advanced strategies is essential for effective long-term retirement and healthcare savings.

Tax Planning for Business Owners

The conversation touches on specific opportunities for small business owners, with a focus on the Qualified Business Income (QBI) deduction. It stresses the importance of meeting specific wage and other requirements to avoid having this valuable 20% pass-through income deduction significantly reduced or eliminated.

For entrepreneurs and owners of pass-through entities, proactive planning around QBI and retirement contributions can lead to substantial tax savings that directly impact the business's and owner's bottom line.

Get started free

Topics

Tax Planning Year-End Strategy Tax-Loss Harvesting Capital Gains Charitable Giving Donor-Advised Funds (DAFs)SALT Deduction Retirement Accounts 401(k)Roth IRA HSA (Health Savings Account)Qualified Business Income (QBI)Direct Indexing Equity Compensation State Tax Law

Processed Apr 15, 2026 yt-dlp + mlx-whisper + Gemini