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Individuals with substantial business holdings often face complicated estate tax issues. Failing to recognize and plan for these issues may adversely impact the ability of the estate to timely pay any estate tax it owes. What is more, a lack of planning can affect the ability of the business to continue operating in the manner envisioned by the current and succeeding owners.

As tax strategy becomes more central than ever to business success, tax leaders must adopt new capabilities beyond those traditionally required to lead the tax function. Essential to this evolution is the ability to develop and execute a forward-looking tax roadmap that fully integrates emerging technologies such as artificial intelligence (AI).

This article explains how Tax Advantaged Equity (TAE) portfolios are traded over time and illustrates how value is achieved over the course of the portfolio’s life. For a TAE portfolio with an objective to harvest available losses and minimize gains while managing risk, there will generally be a few major phases through the life of the portfolio, including loss maximization, loss harvesting and gain minimization, and maturity.

Tax season is an ideal time to think about your overall financial planning strategies and goals, including charitable giving. In this article, Schwab Charitable provides an overview of the current giving environment, as well as introduce you to five donors to understand their giving strategies in action – and help you consider what might work with your broader family philanthropy planning goals.

Single family offices should understand Lender Bagel structures and consider using them if they are not already. Knowledge of this structure has spread like wildfire since the landmark case, Lender Management LLC v. Comm’s. This article equips the reader with an understanding of the core principles of what Lender Bagel structures and how to investigate if it will help the family. With the proper structure, families can harvest the tax savings and other benefits that are available.

Cryptocurrency has revolutionized the financial markets but also created tax traps for the unwary investor. Building on proposed regulations issued in 2023, the IRS has increased its oversight of cryptocurrency transactions by requiring brokers, beginning in 2025, to report investor sales and exchanges in connection with such transactions. Taxpayers not complying with these requirements may face penalties based on accuracy of reporting. For federal tax purposes and regulatory compliance, any form of virtual currency is treated as property and not cash.

In this 10-minute interview, attorney Jordan Bergmann of Foley & Lardner joins Brian Lucareli to discuss qualified business stock (QSBS). During the interview, Jordan defined QSBS and the tax benefits they provide and how family offices can take advantage of the QSBS as part of their wealth management and tax planning strategy.

The importance of meeting U.S. tax and reporting deadlines cannot be overstated. With the IRS continuing to strengthen its efforts to enforce compliance with initiatives specifically targeting foreign information reporting, this U.S. reporting checklist by Kozusko Harris Duncan can help family advisers and trustees of foreign trusts determine what if any U.S. reporting will be due.

The issue of concentrated low-basis holdings is a challenge that has vexed wealth managers and their clients for decades. Put simply, if a large majority of your wealth is concentrated in a single position, should you sell some of it and move the proceeds to a more diversified portfolio of investments? However, the sale position oftentimes carries enormous unrealized capital gains with a huge tax liability. But over the years, new ways of looking at the concentrated position have evolved to provide a more robust and meaningful solution.