Apr 17, 2026
In this episode:
- Why most taxpayers don’t itemize anymore, and when it still actually makes sense to do so
- The hidden fine print on mortgage interest deductions, including caps that quietly limit what high-balance homeowners can write off
- How home equity loans can either save you on taxes, or cost you the deduction entirely depending on how you use the money
- The real story behind points, refinancing, and why timing matters more than most people realize
- Why some common “write-offs” like mortgage insurance premiums rarely benefit higher earners
- A major shift in state and local tax deductions, and why some business owners may suddenly see bigger write-offs
- The growing cost pressure of employee health insurance, and the moment your business is legally required to offer it
- How benefits strategy isn’t just an expense, it’s a recruiting weapon if you play it right
- A surprising tax change around gambling income that quietly increases what people owe
- Why the IRS insists you pay taxes throughout the year, not just in April, and how that impacts cash flow
- The concept of “safe harbor” payments and how it can protect you even if your income swings wildly
- A lesser-known payroll strategy some business owners use to legally manage timing of tax payments
- Why tax planning isn’t just a nice-to-have, it’s the difference between scrambling in April and being in control year-round