Matthew Erskine

5 days ago | fa-mag.com | Matthew Erskine

Parents face a perennial question in estate planning: whether they should equally divide the assets they’re going to pass on to their children. Traditionally, equal division has been the norm, since parents want to be fair and keep the family unified.

1 week ago | forbes.com | Matthew Erskine

The recent upheaval in the senior management of Market Basket, a leading supermarket chain in the Northeast, serves as a stark reminder of the challenges inherent in family business succession planning. CEO Arthur T. Demoulas's has been suspended allegedly because he is planning a work stoppage and has circumventing established succession protocols to name his successors. This incident is a cautionary tale for estate planning professionals and family business owners.

1 week ago | forbes.com | Matthew Erskine

For ultra-high-net-worth (UHNW) families, effective planning transcends financial management. It involves a comprehensive strategy that integrates tax, legal, investment, and philanthropic efforts together with both eldercare for older clients and education for younger clients, into a seamless whole. Unfortunately, many UHNW individuals still experience fragmented planning, as many firms focus narrowly on specific areas like tax mitigation or asset protection without considering the big picture.

2 weeks ago | forbes.com | Matthew Erskine

In the world of financial planning, few strategies have garnered as much attention and intrigue as the "Thiel Strategy." Named after Peter Thiel, the co-founder of PayPal, this approach leverages the unique tax advantages of Roth IRAs by investing in high-growth, illiquid assets like startup equity. The essence of the strategy lies in funding a Roth IRA with assets that, while initially undervalued, such as founder’s stock, have the potential to appreciate significantly over time.

3 weeks ago | forbes.com | Matthew Erskine

In2020, I explored several options for deferring capital gains tax on the sale of artwork. Since then, tax law has evolved, and new tools have emerged, offering collectors, investors, and estate planners updated strategies for managing highly appreciated art and collectibles. As of 2025, sellers face an effective federal tax rate that can exceed 31.8%, plus state taxes, when parting with artwork—making proactive tax planning more essential than ever.