About

The Tax Strategy Playbook is a podcast for real estate investors and business owners who are tired of letting the IRS be their biggest business partner. Each episode breaks down practical, legal strategies to reduce taxes, increase cash flow, and accelerate wealth—without turning you into a tax professional. If you own rental property, syndicate deals, or advise investors, this show is designed to help you use the tax code as a wealth‑building tool, not just an annual chore.

Hosted by David “Mr. Cash Flow” Wiener, The Tax Strategy Playbook focuses on real-world conversations, case studies, and step‑by‑step plays you can discuss with your own advisors. You’ll hear from tax strategists, CPAs, attorneys, lenders, and active investors who are actually using these strategies in the field. Topics include cost segregation, bonus depreciation, 179D and energy incentives, passive loss rules, short‑term and long‑term rental planning, entity structure, and how to coordinate your overall tax plan with your investing strategy.

The Tax Strategy Playbook exists because most investors don’t have a tax strategy—they just have a tax preparer. David created this podcast to close that gap and give you the same kind of thinking normally reserved for the boardroom and the ultra‑wealthy. Episodes are intentionally practical: you’ll walk away with questions to ask your CPA, ideas to run by your attorney, and concrete next steps you can take before year‑end, not after the damage is done.

Whether you’re just buying your first rental or you’re managing a large, multi‑state portfolio, you’ll find insights you can apply at your level today. The show is especially useful for:

Real estate investors (single‑family, multifamily, commercial, and STRs)
Syndicators, fund managers, and deal sponsors
Business owners
CPAs, EAs, and tax professionals who want to think more strategically for their clients

New episodes are released regularly and are designed to be both educational and conversational—no fluff, no scare tactics, just honest, practical tax strategy from people who live in the real estate world every day. If you’re ready to stop overpaying in taxes and start playing offense with your tax planning, you’re in the right place.

At the end of each episode, David encourages you to identify one idea to explore with your advisory team and one person to share the episode with. Over time, those small, consistent moves can create a major shift in your after‑tax wealth. Welcome to The Tax Strategy Playbook—where smart investors learn how to make the tax code work for them.

About the Host

David Wiener

CEO, Tax Strategist, Speaker, Educator

David “Mr. Cash Flow” Wiener is a nationally recognized authority on real estate tax strategy and cash flow optimization, and the host of The Tax Strategy Playbook podcast. As Founder and CEO of Cash Flow Strategies, Inc., David has spent decades helping real estate investors, business owners, and their advisory teams legally reduce taxes, unlock hidden cash flow, and put more money back into productive assets instead of into the IRS.
Over the course of his career, David has become especially known for his work with cost segregation, 179D energy-efficient commercial building deductions, and other engineering-based tax incentives that accelerate depreciation and free up capital. He has also built a long track record in cash flow and accounts receivable optimization, helping clients improve profitability and financial stability without simply “working harder” or taking on more risk.
David is a sought‑after speaker, trainer, and educator, with audiences ranging from national industry conferences to small mastermind groups and professional associations. He is known for his clear, practical teaching style and his ability to translate complex tax concepts into simple, actionable plays that investors and advisors can use right away. Whether he is speaking to CPAs, medical and dental practice owners, or real estate investors, David’s message is consistent: tax strategy is one of the most powerful—and most overlooked—wealth multipliers available.
On The Tax Strategy Playbook, David brings that same real‑world experience and teaching approach to the microphone. Each episode features in‑depth conversations with top tax strategists, CPAs, attorneys, lenders, and active investors who are using the tax code proactively to build wealth. David guides listeners through topics like bonus depreciation, passive loss rules, real estate professional status, short‑term rental planning, and entity structuring, always with an eye toward what actually works in the field, not just on paper.
Beyond his professional credentials, David is a husband, father, and grandfather who understands that tax planning is ultimately about building lasting wealth and freedom for real families, not just chasing deductions. He created The Tax Strategy Playbook to give serious investors and their advisors a place to learn the strategies usually reserved for boardrooms and ultra‑high‑net‑worth clients—and to empower them to have better, more strategic conversations with their own tax professionals.
If you’re ready to stop treating taxes as a once‑a‑year headache and start using them as a core part of your wealth strategy, David Wiener is the guide you want in your corner.