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 Dolly Parton and the catalog she built to outlast her.

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.