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The Tax Strategy Playbook

The Tax Strategy Playbook

By: David Wiener "Mr. Cash Flow"
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The Tax Strategy Playbook is where real estate investors and business owners learn how to stop overpaying the IRS and turn taxes into an opportunity center instead of an annual pain point.

Each episode, host David Wiener (“Mr. Cash Flow”) sits down with CPAs, tax attorneys, cost segregation experts, and top investors to break down complex tax rules into clear, step‑by‑step strategies you can actually use.

You’ll hear real case studies, before‑and‑after numbers, and practical checklists on things like cost segregation, bonus depreciation, real estate professional status, short‑term rental strategies, entity structure, and more—without legalese or fluff. Expect straight talk, tactical advice you can hand to your CPA, and simple action items at the end of every show so you always know what to do next.

2026 David Wiener, "Mr. Cash Flow" Economics Personal Finance
Episodes
  • Stop Overpaying Taxes: Cost Segregation and Bonus Depreciation Explained

    Stop Overpaying Taxes: Cost Segregation and Bonus Depreciation Explained
    Mar 17 2026

    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 capital for property owners and investors.
    • Choosing a quality cost segregation firm is crucial for ensuring a high-quality engineering-based study and robust audit support.
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    17 mins
  • Why Tax Strategy Is the Real Wealth Multiplier (and How Real Estate Investors Actually Use It).

    Why Tax Strategy Is the Real Wealth Multiplier (and How Real Estate Investors Actually Use It).
    Mar 9 2026

    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 proactive planning to legally reduce their tax bill and keep more cash working inside their portfolios.

    In this conversation, Greg shares his journey into real‑estate‑focused tax strategy, the “lightbulb moment” that changed how he views the tax code, and the top mistakes he sees even experienced investors make.

    You’ll hear:

    • The 3 biggest ways investors and operators routinely overpay in taxes

    • How proactive planning (vs. once‑a‑year filing) can dramatically change your cash flow

    • A real client story where better strategy meant a major tax savings

    • The one action you should take in the next 7 days if you suspect you’re overpaying.

    If you’re ready to stop writing unnecessary checks to the IRS and start using the tax code as a wealth‑building tool, this episode is your starting point.

    Connect with Greg Taylor:

    • Website: https://taylortaxstrategy.com

    • LinkedIn: https://www.linkedin.com/in/gregtaylor

    Connect with your host, David “Mr. Cash Flow” Wiener:

    • Website: https://taxstrattegyplaybook.com

    • LinkedIn: https://www.linkedin.com/in/cashflowstrategies/

    Hit play, take notes, and then send this episode to one investor or business owner you know is probably overpaying in taxes.
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    22 mins
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