Real Questions Wealthy Families Actually Ask | Ep. 54

In this episode, Dave Grant and Heather Townsend go rapid fire through a stack of real listener questions in a special “What Would You Do?” format. No deep dive, just straight answers, real-world trade-offs, and the money conversations high earners actually have behind closed doors.What you’ll learn...• The truth about the short-term rental “tax bill to $0” claim, and when depreciation can actually offset W-2 income• Why cost segregation matters, and why the land value (like beachfront property) can kill the strategy• How to figure out what’s pre-tax vs after-tax when you’ve rolled multiple401(k)s into an IRA (and what happens if you cannot prove it)• What to do if your phone (with cards attached) gets stolen, plus why credit cards beat debit cards for fraud protection• Why freezing your credit can be a pain, but worth it• Hedge funds, limited partnerships, and long-short funds explained simply, including the biggest risks: fees, complexity, and illiquidity• How to keep a future inheritance separate in a second marriage, and why an estate attorney matters before the money hits• The “huge bonus” playbook: taxes first, emotions second, then intentional spending and saving• What to do when a surviving spouse inherits complex real estate, including the step-up-in-basis angle and the “would you buy this today?” test• Plus: the unexpected “Would you rather?” showdown (Bitcoin vs Birkin)