Into the Woods

In this episode of Into the Woods–the final part of a three-part series on intellectual property–attorney Trent Bolar joins host Dave Shaffer to explain how copyright works, when a work enters the public domain, and why ownership structure matters so much for a creator’s estate. Plus, the AI training lawsuits reshaping copyright law, the Tupac estate’s cease-and-desist letters, and a tribute to Do...

In this episode of Into the Woods–part two of a three-part series on intellectual property–attorney Trent Bolar joins host Dave Shaffer to explain what a trademark actually protects, why use in commerce is the key to keeping one alive, and what happens to a mark when its owner passes away. Plus, the NCAA’s trademark fight with DraftKings and the reason bars and restaurants call it the big game.

In this episode of Into the Woods–part one of a three-part series on intellectual property–attorney Trent Bolar joins host Dave Shaffer to explain how patent rights are handled after death, including executor responsibilities, ownership structures, and maintenance fees. Plus, the fascinating story behind Michael Jackson’s patented shoe that made his famous lean possible.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.