Podcast
Into the Woods
Hosted by Woods Oviatt Gilman · EN
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.
18episodes
Episodes
Newest firstAll episodes
Episode 21 – Estate Planning as a Team Sport (Part 2)
Mar 300:16:23Tap to summarizeIn 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.
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Episode 20 – Estate Planning as a Team Sport (Part 1)
Feb 1700:17:28Tap to summarizeIn 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.
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Episode 19 – Real Estate & Estate Planning: Trusts & LLCs (Part 2)
Feb 300:14:06Tap to summarizeIn 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.
Transcribe →2026 Trends Video Special – Top 5 Estate Planning Trends for the New Year
Jan 2100:11:25Tap to summarizeIn 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.
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Episode 18 – Real Estate & Estate Planning: The Fundamentals (Part 1)
Dec 3000:15:56Tap to summarizeIn 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.
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Episode 17 – Charitable Giving: Doing Good While Doing Smart
Dec 900:15:09Tap to summarizeIn 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.
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Episode 16 – The Five-Year Lookback Period: What You Need to Know (Part 2)
Nov 1800:23:36Tap to summarizeIn 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.
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Episode 15 – The Five-Year Lookback Period: What You Need to Know (Part 1)
Nov 400:13:35Tap to summarizeIn 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.
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