The Tax Strategy Playbook

Avoid a surprise irs tax recapture bill after your cost segregation study. Learn how to plan for the tax implications of selling property.

Completing a cost segregation study is a standard strategy for real estate investors, but many overlook the long-term tax consequences. This video explains why the irs may reclaim deducted amounts when you sell your investment property. If you are a property owner or real estate investor,...

The IRS just opened a 90-day settlement window — after that, it's 40% penalties and a near-total deduction wipeout. If you or any of your clients have ever participated in a syndicated conservation easement, this is the most important episode you'll watch all year.

My guest, Victoria Boon, spent over 20 years as an IRS Senior Revenue Agent and Subject Matter Expert inside the Large Business & International Division. She wo...

Bad timing destroys more wealth than bad investments ever will. In this episode of The Tax Strategy Playbook, David Wiener (Mr. Cash Flow) sits down with Gary Preisser — Managing Partner of Stonebriar Wealth Advisors and creator of the Cash Flow Clock — to break down exactly how business owners, real estate investors, and CPAs can stop reacting to tax disasters and start designing wealth that works on their terms.

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⚠️ Most real estate investors don't lose money on bad deals — they lose it on BAD TAX DECISIONS they didn't even know they were making.

In this episode of The Tax Strategy Playbook, host David Wiener (Mr. Cash Flow) sits down with Scott Estill — a former IRS Senior Trial Attorney turned nationally recognized tax attorney, speaker, and author — to expose the 7 tax traps quietly destroying investor wealth in 2026.

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Are you a tired landlord sitting on hundreds of thousands — or even millions — in capital gains and depreciation recapture, terrified of the tax bill that comes with selling? You're not alone. And there IS a better way.

In this episode of The Tax Strategy Playbook, host David Wiener (Mr. Cash Flow) sits down with Tommy Olson, Vice President at Kay Properties & Investments — one of the nation's leading Delaware ...

Tired of TikTok “tax hacks” and viral write‑off tricks that could actually trigger an IRS audit? In this Tax Strategy Playbook episode, David Wiener (Mr. Cash Flow) exposes 7 social media tax myths and shows you the real 2026 tax strategy wealthy investors use instead.

If you’re serious about long‑term tax planning, bonus depreciation, cost segregation, and keeping more cash flow in your pocket, this is your playbo...

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If you’re a high-income W-2 earner, 1099 professional, real estate investor, or business owner looking for advanced tax strategies to reduce taxes, this episode breaks down a powerful oil and gas tax strategy to legally offset W-2 income, use intangible drilling costs (IDC) d...

Real estate tax strategy with short-term rentals is one of the most powerful ways high-income W‑2 earners and business owners can legally slash their tax bill without real estate professional status. In this episode of The Tax Strategy Playbook, David Wiener (Mr. Cash Flow) and CPA/investor Ryan Bakke break down how to use the short-term rental “loophole” plus cost segregation and bonus depreciation to offset W‑2 and bu...

$100K+ R&D TAX CREDIT 2026 EXPOSED – The Secret Dollar-for-Dollar IRS Tax Credit You’re Quietly Donating Every Year! Construction Tax Credits, Manufacturing Tax Credits, Software Development Tax Credit, Architecture & Engineering Tax Savings, Winery R&D Credits, Brewery Tax Credits, Law Firm Tax Hacks & More – NO Lab Coats, NO Patents, NO Billion-Dollar Tech Company Needed! Business Owners & En...

In this eye-opening episode of the Tax Strategy Playbook, David Wiener (Mr. Cash Flow) sits down with 179D expert Brian Broussard to reveal how commercial building owners, developers, and designers can still claim massive Section 179D energy-efficient tax deductions before the June 30, 2026 deadline under the One Big Beautiful Bill. Discover who qualifies, how the deduction works on new builds and renovations, real-world six- and s...

Landlords Don’t Have a Tax Problem—It's a STRATEGY Problem Killing Cash Flow

Most landlords think they’re overpaying taxes. The truth? Their properties, tenant laws, and tax code are all pulling in opposite directions — quietly destroying cash flow and passive income.

In this episode of The Tax Strategy Playbook, David Wiener sits down with top real estate broker Christian Walsh to expose the biggest rental po...

Most business owners and real estate investors are about to sleepwalk past the biggest tax opportunity of the decade—and the IRS is counting on it.

In this episode of The Tax Strategy Playbook, host David Wiener breaks down the 2025 “One Big Beautiful Bill” and shows you, step by step, how to turn this new tax law into a weapon instead of a hammer.

If you own a business, rentals, or both, this is not another boring ...

Most real estate investors assume a cost segregation study automatically creates a tax win. But if the IRS sees your rental as passive, those losses may not offset your W-2 or business income the way you expected. In this episode, David Wiener and Gabriel Virdaru break down passive vs. active real estate in plain English, explain real estate professional status, and show how material participation can unlock serious tax savings.

We ...

You’re about to find out whether your LLC or S corp is quietly costing you thousands in taxes.

In this episode of The Tax Strategy Playbook, host David Wiener sits down with Matt Bontrager, CPA, managing partner of TrueBooks, a firm that works almost exclusively with real estate investors and entrepreneurs. Matt has seen hundreds of real‑world structures—good, bad, and ugly—and he pulls back the curtain on how enti...

This episode delves into the concept of cost segregation and bonus depreciation in real estate, explaining how it works, its benefits, myths, and considerations for choosing a quality cost segregation firm. The episode provides practical insights for property owners and investors to optimize their tax planning and cash flow.

Takeaways

• Cost segregation and bonus depreciation can significantly improve after-tax returns and free up ...

Stop letting the IRS be your biggest business partner. In this first episode of The Tax Strategy Playbook, host David Wiener (“Mr. Cash Flow”) sits down with tax strategist Greg Taylor to unpack the real reasons real estate investors and business owners quietly overpay the IRS year after year—and what to do about it.

Greg is the founder of Taylor Tax Strategy, where he helps investors and entrepreneurs use proactiv...