Into the Woods

The legal landscape doesn’t have to be a dark, scary place. With host Dave Shaffer, Partner and Chair of the Family Wealth and Estate Planning Department at Woods Oviatt Gilman, as your guide, we talk through a variety of legal topics, shedding light on the issues of the day, welcoming guest attorneys from across the Woods Oviatt Gilman law firm, and answering questions to help you see both the forest and the trees.

Episodes

Mar 3, 2026

16 min

In Part 2 of their teamwork series, Dave Shaffer and Hannah Cannon discuss estate administration, tax filing requirements, and the importance of working with financial advisors—plus a $21 million lesson about fiduciary duty.

Feb 17, 2026

17 min

In Part 1 of their teamwork series, Dave Shaffer and Hannah Cannon discuss why estate planning requires collaboration between lawyers, financial advisors, and insurance agents—plus a cautionary case about the cost of failing to coordinate.

Feb 3, 2026

14 min

In Part 2 of their real estate series, Dave Shaffer and Tom Rickettson discuss trusts and LLCs as tools for avoiding probate, protecting assets, and managing property—plus celebrity examples of creative trust naming for privacy.

Jan 21, 2026

11 min

In this special video episode filmed at the WOG holiday party, Dave Shaffer and Caroline Cercone preview the top 5 estate planning trends for 2026—including New York estate tax strategies, gifting, asset protection, and digital asset planning.

Dec 30, 2025

15 min

In Part 1 of their real estate series, Dave Shaffer and Tom Rickettson discuss how property ownership affects estate planning, explain common deed structures, and share lessons from HBO's Succession about the importance of planning ahead.

Dec 9, 2025

15 min

In this episode, Dave Shaffer and Caroline Cercone discuss the fundamentals of charitable giving, including donor-advised funds, private foundations, and charitable trusts. They share practical planning advice and a cautionary tale about vetting charities before you donate.

Nov 18, 2025

23 min

In Part 2 of their series on the five-year Medicaid lookback period, attorneys Dave Shaffer and Hannah Mills discuss overlooked transactions that can count as gifts, share lessons from a real fair-hearing case, and offer documentation tips to help families avoid costly Medicaid penalties.

Nov 4, 2025

13 min

In this episode, attorneys Dave Shaffer and Hannah Mills explore the five-year Medicaid lookback period, explaining how it works, why it matters, and sharing a real fair hearing case about the consequences of making gifts to family members—even with good intentions.

Oct 21, 2025

17 min

In this episode, attorneys Dave Shaffer and Hannah Cannon explore the critical role of beneficiary designations in estate planning, explaining how these often-overlooked forms can override your will and sharing lessons from a Supreme Court case about the costly consequences of neglecting to update them.

Oct 7, 2025

26 min

In this episode, attorneys Dave Shaffer, Kelly Gusmano, and Hannah Mills explore asset protection trusts for Medicaid planning, explaining how these irrevocable trusts can protect your home and investments from nursing home costs while preserving your right to live comfortably.

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