Into the Woods

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.

Episode 17 – Charitable Giving: Doing Good While Doing Smart

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.

Episode 16 – The Five-Year Lookback Period: What You Need to Know (Part 2)

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.

Episode 15 – The Five-Year Lookback Period: What You Need to Know (Part 1)

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.

Episode 14 – The Critical Importance of Beneficiary Designations in Estate Planning

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.

Episode 13 – Asset Protection Trusts & Protecting Your Home

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.

Episode 12 – Do I Really Need a Trust?

In this episode, attorneys Dave Shaffer and Morgan Napierski explore the fundamentals of trust planning, explaining when trusts are necessary, how they work, and the critical importance of proper trust funding.

Episode 11 – Understanding Probate and Estate Planning Basics

In this episode, attorneys Dave Shaffer and Caroline Cercone explore the probate process, debunking common misconceptions while explaining when to avoid probate and when court oversight can actually protect your loved ones.