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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 ...

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 ...

With the new administration in the U.S. and its focus on various parts of the Tax Cuts and Jobs Act (the TCJA) and the estate tax, changes are expected amid the balancing of competing considerations. In this 10-minute interview, Jason Kohout, partner and co-chair of the Family Offices group at Foley & Lardner, and John Strom, federal lobbyist a...

For many art collectors, the allure of acquiring and displaying art often overshadows the effort required to manage it properly and plan for its eventual disposition. After all, upon death, you can’t take it with you. Estate planning for art collectors involves navigating a complex landscape of valuation, tax, and management issues. Without a strat...

Effectively transitioning a business to the next generation of owners through a business succession plan that incorporates estate tax planning will result in the most value being retained by the owners and their families. Whether the business is entirely family owned or has unrelated owners, each scenario comes with its own complications but with c...

With an unprecedented $80 billion additional funding allocated for the Internal Revenue Service (IRS), there will be an expected 3,700 new agents hired as part of ramping up audits of the largest and most complex partnership returns and other tax enforcement initiatives. There will also be more focus on high income individuals, foreign bank account...

A major trend with family enterprise organizations is designing ways to develop and retain early career professionals. The most effective emerging practice is to develop a strategy that blends the quantitative skills necessary to meet the financial, legal and technical needs of a family, along with the qualitative skills needed to navigate complexi...

The success of a private equity fund’s investment in a portfolio company largely hinges on the performance of the Chief Financial Officer (CFO). Initially chosen CFOs may be ideal for early goals, but market shifts might necessitate a change in CFO to adapt and succeed. Understanding the unique skills of different CFO archetypes is key for funds to...

The most popular forms of equity-based compensation are stock options and restricted stock. It is not uncommon for these vehicles to compose a substantial portion of an executive’s net worth. Accordingly, it is important that executives fully understand the income tax treatment of options and restricted stock in order to maximize the after-tax valu...

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, i...

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). ...

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 cur...

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. Taxpayer...

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 investi...

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 ...