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.
15episodes
Episodes
Newest firstAll episodes
Episode 28 – Medicaid Applications: The Documentation Gauntlet
2d ago00:16:27Tap to summarizeIn this episode, Dave Shaffer, Hannah Mills, and Kristel Martini discuss the documentation process for Medicaid applications, covering deadlines, caseworker requests, and tips for navigating the five-year lookback requirement.
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Episode 27 – Will Contests: When Family Fights Back
2w ago00:16:43Tap to summarizeIn this episode, Dave Shaffer and Hannah Cannon discuss the legal grounds for contesting a will in New York, no-contest clauses, and lessons from the movie Knives Out about why will challenges rarely succeed.
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Episode 26 – Digital Legacy Planning: Beyond the Will (Part 2)
May 500:11:48Tap to summarizeIn Part 2 of their digital estate planning series, Dave Shaffer and Caroline Cercone discuss digital legacy planning, explaining why you need both a legal will and a social media plan—plus a Taylor Swift-themed breakdown of how each works.
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Episode 25 – Electronic Wills: Welcome to the Digital Age (Part 1)
Apr 2800:18:40Tap to summarizeIn Part 1 of their electronic wills series, Dave Shaffer and Caroline Cercone discuss New York's new digital will law (effective December 2027), covering how it works, the risks involved, and lessons from the Samsung Galaxy Will case.
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Episode 24 – Transfer on Death Deeds: Does New Mean Good?
Apr 1400:17:55Tap to summarizeIn this episode, Dave Shaffer and Morgan Napierski discuss New York's new Transfer on Death deed law, explaining the limitations and pitfalls that make this probate avoidance tool less useful than it seems for most families.
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Episode 23 – Why Estate Planning Isn’t Just for Your Parents and Grandparents
Mar 3100:18:31Tap to summarizeIn this episode of Into the Woods, attorney Hannah Mills joins host Dave Shaffer to explain why estate planning isn’t just for older generations. They cover New York’s intestacy laws, planning considerations for young families, unmarried couples, and business owners, and share a cautionary tale about the author of The Girl with the Dragon Tattoo.
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Episode 22 – 10 Immediate Steps to Take When a Loved One Passes Away
Mar 1700:18:43Tap to summarizeIn this episode of Into the Woods, host Dave Shaffer and estates paralegal Deana Kilpatrick walk through the 10 immediate steps families should take when a loved one passes away – from obtaining death certificates and finding the will to tracking assets, managing debts, and knowing when to seek legal guidance.
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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.
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