Death, Taxes, and the Caregiver To-Do List

After a few months away, Barry and Bobby are back—and there’s a lot to catch up on.

Bobby shares the loss of his mother after her long journey with Alzheimer’s and talks about something many families may never have considered: whole-body donation for medical education and research. He walks through his family’s experience, how the process works, what happens afterward, and why having these conversations and making decisions ahead of time can make an enormous difference for the people left behind.

From there, naturally, it’s time for the other unavoidable topic: taxes. Bobby shares some lessons from handling his mother’s estate, particularly why anyone inheriting an annuity needs to understand exactly what they have before assuming all that money is theirs to spend.

Barry also shares an unsettling encounter his dad had with aggressive door-to-door home-improvement salespeople—and the surprisingly simple “do not call, do not knock” approach that finally stopped them.

And then there’s something nearly every caregiver recognizes: the list. You arrive to visit someone you love and, before you’ve gotten through the door, there are already four things waiting for you to fix. Barry and Bobby talk about setting boundaries without feeling guilty—and why “I’ll put it on the list” might be one of the most useful phrases in the caregiver vocabulary.

Finally, the guys wrap up with a few tech picks, including countdown apps Bobby uses to keep upcoming events visible and Barry’s wonderfully simple solution to the eternal video-call question: “Am I muted?”