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

Aug 4, 2026
Aug 4, 2026
15 min
In this episode of Into the Woods, attorney Hannah Cannon joins host Dave Shaffer to explain New York’s spousal right of election–the law that prevents a spouse from being completely cut out of an estate. They cover how the right works, when it can be waived, and share a cautionary tale about the lead singer of The Cars and his estranged supermodel wife.

Jul 14, 2026
Jul 14, 2026
16 min
In Part 2 of their retirement accounts series, Dave Shaffer and Morgan Napierski cover SECURE Act 2.0, exceptions to the 10-year rule, and the difference between conduit and accumulation trusts—plus a fun Jeopardy round to test it all.

Jun 23, 2026
Jun 23, 2026
11 min
In Part 1 of their retirement accounts series, Dave Shaffer and Morgan Napierski discuss how IRAs and 401(k)s pass at death, beneficiary designation best practices, and the major changes brought by the SECURE Act 1.0.

Jun 2, 2026
Jun 2, 2026
16 min
In 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.

May 19, 2026
May 19, 2026
16 min
In 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.

May 5, 2026
May 5, 2026
11 min
In 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.

Apr 28, 2026
Apr 28, 2026
18 min
In 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.

Apr 14, 2026
Apr 14, 2026
17 min
In 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.

Mar 31, 2026
Mar 31, 2026
18 min
In 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.

Mar 17, 2026
Mar 17, 2026
18 min
In 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.








