Episodes

The 2025 Tax Bill, officially known as the One Big Beautiful Bill, is the biggest tax law change in nearly a decade. And most small business owners and real estate investors are about to sleepwalk right past it. In this episode of The Tax Strategy Playbook, host David Wiener breaks down exactly what the One Big Beautiful Bill means for small businesses, real estate investors, rental property owners, and entrepreneurs, and how to turn these new tax law changes into a concrete action plan before ...

Most real estate investors assume a cost segregation study automatically creates a tax win. But if the IRS classifies your rental activity as passive, those losses may be trapped, unable to offset your W-2 income or active business income the way you expected. In this episode of The Tax Strategy Playbook, David Wiener and CPA Gabriel Virdaru break down the passive vs. active deduction rules in plain English. You'll learn exactly how the IRS distinguishes passive income from active income, why...

Choosing the wrong entity structure is one of the most expensive mistakes real estate investors and small business owners make, and most don't find out until it's too late. In this episode of The Tax Strategy Playbook, host David Wiener sits down with Matt Bontrager, CPA and managing partner of TrueBooks, a firm that works almost exclusively with real estate investors and entrepreneurs. Matt has reviewed hundreds of real-world LLC and S corp structures and pulls back the curtain on how entity s...

In this episode, we break down cost segregation for real estate investors who want more cash flow and less tax drag on their rentals and commercial properties. You’ll learn how cost segregation accelerates depreciation by carving out 5, 7, and 15-year components inside your property, and how bonus depreciation lets you front load those deductions into the early years of ownership. We cover how cost segregation applies to everyday investors across many asset types: single-family rentals, dupl...

If you're a real estate investor or business owner, tax strategy is the single most powerful wealth multiplier available to you, and most people are using it wrong. In this debut episode of The Tax Strategy Playbook, host David Wiener ("Mr. Cash Flow") sits down with tax strategist Greg Taylor, founder of Taylor Tax Strategy, to unpack exactly why real estate investors and business owners quietly overpay the IRS year after year, and what proactive tax planning can do about it. Greg shares the ...