About

Most investors and business owners spend their careers working hard to build wealth, only to watch a significant chunk of it disappear into the IRS's pockets every April. The Tax Strategy Playbook is here to change that, turning your tax bill from a recurring pain point into a strategic advantage that fuels your long-term growth.

About the show

Hosted by David Wiener—known to his listeners as "Mr. Cash Flow"—this podcast cuts through the dry legalese and confusing tax code to give you a clear, tactical roadmap for keeping more of what you earn. We believe that taxes shouldn't be a guessing game or something you leave entirely to a CPA who only looks at your file once a year.

Every week, we bring in high-level experts—including CPAs, tax attorneys, and cost segregation specialists—to break down complex financial maneuvers into simple, actionable steps. Whether we are discussing the tax benefits of oil and gas investments or helping you navigate the massive legislative shifts in the 2025 tax code, our goal is the same: to provide the straight talk you need to stop overpaying. We focus on real-world application, offering concrete examples of how to optimize your entity structure or use tools like cost segregation for short-term rentals to slash your W-2 tax burden.

What you'll discover

How to avoid the common cost segregation traps that can trip up even experienced real estate investors.
Strategic ways to utilize R&D tax credits for construction, manufacturing, or software development without needing a lab coat.
How to execute a DST 1031 exchange to defer massive capital gains taxes when you're ready to stop managing properties.
The truth behind viral "tax hacks" and which social media strategies are actually audit bait.
How to properly classify your rental activity to ensure your rental losses don't stay trapped in passive status.
Why choosing the wrong entity structure between an LLC and an S Corp could be silently eroding your wealth.

Who this podcast is for

This show is built for the high-achieving real estate investor, the small business owner, and the high-income professional who is tired of playing defense. If you feel like your current tax strategy is non-existent, or you're worried that your lack of planning is costing you more than any bad market downturn ever could, you’ve found your home. You don't need to be a tax attorney to listen; you just need to be someone who cares about protecting your cash flow and is ready to take control of your financial destiny.

Meet the host

David “Mr. Cash Flow” Wiener has spent his career obsessed with the mechanics of wealth creation. He understands that for investors, the difference between building lasting legacy wealth and barely breaking even often comes down to tax efficiency. By stripping away the fluff and focusing on tactical, legal, and proven strategies, David helps his listeners bridge the gap between "working for money" and "making your money work for you."

Start listening

Stop letting the IRS dictate your financial future. Whether you have a five-minute commute or an hour-long drive, each episode provides a "ready-to-use" checklist you can hand directly to your CPA. Subscribe to The Tax Strategy Playbook today and start building the tax-efficient future you deserve.

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.