Into the Woods

Episode 26 – Digital Legacy Planning: Beyond the Will (Part 2)

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.

Episode 25 – Electronic Wills: Welcome to the Digital Age (Part 1)

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.

Episode 24 – Transfer on Death Deeds: Does New Mean Good?

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.

Episode 23 – Why Estate Planning Isn’t Just for Your Parents and Grandparents

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.

Episode 22 – 10 Immediate Steps to Take When a Loved One Passes Away

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.

Episode 21 – Estate Planning as a Team Sport (Part 2)

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.

Episode 20 – Estate Planning as a Team Sport (Part 1)

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.

Episode 19 – Real Estate & Estate Planning: Trusts & LLCs (Part 2)

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.

2026 Trends Video Special – Top 5 Estate Planning Trends for the New Year

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.

Episode 18 – Real Estate & Estate Planning: The Fundamentals (Part 1)

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.