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)