The Tax Strategy Playbook

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.

  1. 3d ago

    Cost Segregation Myths vs Reality | Which Owner Pays More?

    Cost segregation myths could be costing you tens of thousands of dollars in taxes you don't actually owe. In this episode of the Tax Strategy Playbook, David Wiener (Mr. Cash Flow) puts 5 of the most common cost segregation myths up against the actual numbers — and shows exactly which owners end up paying more simply because they never checked. You'll get the exact cost basis threshold, $150,000, that determines whether an engineering-based cost segregation study is worth running on your property — and why it applies to residential long-term rentals, short-term rentals, commercial, and industrial properties alike, not just large commercial buildings. David also breaks down why a properly documented, engineering-based study isn't the audit risk people assume: the real risk is the cheap, calculator-based shortcut version, not the strategy itself. CSSI, the cost segregation partner behind this show, has completed more than 65,000 engineering-based studies nationwide without ever triggering an audit. You'll learn why your tax professional isn't already running this analysis automatically as part of a normal tax return (it takes a separate engineering-based study to unlock it), and why a look-back study means you haven't missed your window even if you've owned the property for years — it can capture missed depreciation going back as far as 15 years without amending a single prior return. You'll also hear why short-term rentals often qualify even more cleanly than long-term rentals thanks to faster-depreciating furniture, appliances, and finishes, how a 1031 exchange or long-term hold can address depreciation recapture before it becomes a problem, and the exact question David recommends bringing to your tax professional this week — worded so it actually gets you a real answer instead of a shrug. ⏱️ CHAPTERS 00:00 Introduction 01:49 The Promise 03:15 Who This Episode is For 04:16 Why This, Why Now 05:48 Myth #1 - The Big Building Myth 14:31 Myth #2 - The Audit Magnet Myth 19:10 Myth #3 - The Tax Pro Myth 21:08 Myth #4 - The "Too Late" Myth 23:41 Myth #5 - The "Long-Term Rental" Myth 26:44 FAQ 28:43 The Playbook 31:57 Conclusion If a myth in this episode has been quietly costing you money, share it with one investor or business owner who needs to hear it. Subscribe to the newsletter for free resources, including the current 2026 tax planning guide: https://www.taxstrategyplaybook.com/newsletter And before you go, send this to one more person in your circle who owns real estate or a business — a rumor is only expensive until somebody sends them the truth. Contact David directly to discuss your situation or to receivee a free preliminary analysis of your property at David.wiener@cashflowwstrategies.us #CostSegregation #RealEstateInvesting #TaxStrategy #BonusDepreciation #ShortTermRentals

    Cost Segregation Myths vs Reality | Which Owner Pays More?

  2. Jul 14

    The 5 Assets That'll Save Your Heirs (and the 5 That'll Destroy Them)

    I want you to sit with one number: $177,500. That's the tax bill one of my clients avoided entirely — not through a loophole, but by understanding how step-up in basis actually works for real estate investors.   In this episode of The Tax Strategy Playbook, I walk through the 5 best assets you can leave your heirs and the 5 worst estate planning traps real estate investors fall into — traps that can cost families six figures in avoidable taxes and legal fees.   You'll learn: ✅ How step-up in basis can erase capital gains and depreciation recapture at death ✅ Why holding property in an LLC + revocable living trust keeps your estate out of probate ✅ How cost segregation studies compound across generations ✅ How real estate depreciation can fund tax-free Roth IRA conversions for your heirs ✅ Why an ILIT (irrevocable life insurance trust) solves the liquidity problem real estate creates ✅ The 5 worst mistakes: undivided ownership interests, unplanned depreciation recapture, un-documented short-term rental businesses, oversized traditional IRAs, and property left entirely in your personal name ✅ How the 2025 One Big Beautiful Bill Act (OBBBA) changed bonus depreciation and the federal estate tax exemption for 2026   Real-world case study included: how the "Wilsons" — a couple with a $4.4M real estate portfolio — could lose $350K–$500K in unplanned taxes and fees, or preserve it with proper structure.   If you're a real estate investor with rental or commercial property and you've never had a real conversation about how your portfolio and your estate plan fit together, this episode gives you the questions to ask and the gaps to close.   ⏱️ Want cost segregation, a 179D lookback study, or an R&D credit study for your own portfolio? Link in the description to book a call with our team.   🔔 Subscribe to The Tax Strategy Playbook for a new episode every Tuesday.   📌 Topics covered: step-up in basis, cost segregation, LLCs and revocable living trusts, depreciation recapture, Roth IRA conversions, ILITs, bonus depreciation under OBBBA, 1031 exchanges, short-term rental succession planning, and probate avoidance for real estate investors.   Disclaimer: This content is for general educational purposes and is not personalized tax, legal, or financial advice. Consult a qualified tax strategist and estate attorney about your specific situation.   #EstatePlanning #RealEstateInvesting #TaxStrategy #StepUpInBasis #CostSegregation #WealthBuilding #PassiveIncome #GenerationalWealth #1031Exchange #TaxPlanning

    The 5 Assets That'll Save Your Heirs (and the 5 That'll Destroy Them)

  3. Jul 7

    Cost Segregation + Opportunity Zones 2.0: The Tax Strategy Nobody's Talking About

    On July 4, 2025, the One Big Beautiful Bill Act made Opportunity Zones a permanent part of the tax code. On June 18, 2026, the IRS released Notice 2026-40 — brand-new transitional guidance on the handoff from Opportunity Zone 1.0 to Opportunity Zone 2.0. My guest, Jason Watkins, CPA and Chair of the Novogradac Opportunity Zones Working Group, had less than 24 hours with the notice before joining me to break it down.   In this episode of The Tax Strategy Playbook, Jason and I cover exactly what changed and what it means if you have a capital gain in 2026.   You'll learn: ✅ What a Qualified Opportunity Fund (QOF) is and how the capital gains deferral actually works ✅ Why Opportunity Zones becoming permanent under the One Big Beautiful Bill Act matters for investors ✅ The new rolling 5-year deferral and basis step-up: 10% tax-free for urban investments, 30% tax-free for rural ✅ The tax-free 10-year exit — and why there's no bonus depreciation recapture at sale ✅ The critical 180-day investment window, and why it can stretch to nearly 21 months for pass-through gains ✅ IRS Notice 2026-40: the working capital safe harbor, the 10% raised / 5% spent test, and the December 31, 2026 deadline for Opportunity Zone 1.0 census tracts ✅ The difference between an actual inclusion event and a deemed inclusion — and why it matters if you want to redefer your gain into 2027 ✅ How an engineering-based cost segregation study stacks with OZ tax deferral on real estate acquired inside a Qualified Opportunity Fund ✅ Red flags to watch for before investing in a QOF, including the 7% IRS underpayment penalty for non-compliant funds   Jason also shares data on the program's real-world impact, citing EIG research on new housing units created in Opportunity Zones since 2018 — figures worth verifying directly with EIG before you cite them elsewhere.   If you have a 2026 capital gain — from a property sale, a business sale, or a stock sale — this episode gives you the 180-day math and the deadlines you need before you talk to your tax professional.   🔔 Subscribe to The Tax Strategy Playbook for a new episode every Tuesday.   📩 Get the free newsletter at taxstrategyplaybook.com/newsletter for planning guides and cost segregation strategies delivered to your inbox.   📌 Topics covered: Opportunity Zones 2.0, qualified opportunity fund, One Big Beautiful Bill Act, capital gains tax deferral, IRS Notice 2026-40, working capital safe harbor, 180-day rule, basis step-up, rural opportunity zones, cost segregation, bonus depreciation, tax-free exit, real estate investing.   Disclaimer: This content is for general educational purposes and is not personalized tax, legal, or financial advice. Consult a qualified tax strategist and CPA about your specific situation before making an investment or filing decision.   #OpportunityZones #TaxStrategy #CapitalGainsTax #QualifiedOpportunityFund #RealEstateInvesting #CostSegregation #TaxPlanning #OneBigBeautifulBill #WealthBuilding #IRS

    Cost Segregation + Opportunity Zones 2.0: The Tax Strategy Nobody's Talking About

  4. Jun 30

    The Cost Segregation Deduction Trap That Catches Investors Off Guard

    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, understanding these financial risks is essential for accurate cash flow planning. We cover the mechanics of depreciation recapture and how it impacts your bottom line upon exiting an investment. By preparing for these potential tax bill scenarios now, you can avoid unexpected liabilities later. This breakdown is designed to help you make informed decisions about your real estate portfolio. Subscribe for weekly real estate tax breakdowns, and comment below if you have specific questions about your depreciation schedule.

    The Cost Segregation Deduction Trap That Catches Investors Off Guard

  5. Jun 23

    Former IRS Agent: Why Syndicated Conservation Easements Are About to Blow Up

    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 worked directly on the conservation easement enforcement campaign, helped train IRS revenue agents nationwide, and co-authored updates to IRS publications and Form 8824. Today she runs Boon Tax Group and Boon Tax Educators, where she helps taxpayers and tax professionals navigate what the IRS is doing next. We cover what conservation easements are supposed to do, why syndicated deals went off the rails, what the courts are actually finding wrong, and — critically — what to do if you're sitting in one of these deals right now. 🔔 Subscribe for weekly tax strategy breakdowns: https://www.youtube.com/@taxstrategyplaybook ━━━━━━━━━━━━━━━━━━━━━━━━ 📌 CHAPTERS ━━━━━━━━━━━━━━━━━━━━━━━━ 0:00 – Cold Open: 90-Day IRS Settlement Window 0:06 – Show Intro & Why This Episode Matters 2:38 – Meet Victoria Boon: 20 Years Inside the IRS 3:03 – What Is a Conservation Easement? The Basics Explained 4:31 – Where Legitimate Easements End and Tax Shelters Begin 6:09 – What the IRS Saw That Triggered the Enforcement Campaign 8:07 – The 2026 IRS Settlement Offer: 90 Days, Penalties, and the Final Push 11:53 – Syndicated vs. Legitimate: The Valuation Problem Explained 12:39 – What Tax Courts Are Actually Finding Wrong 14:45 – If You Did a Deal 5-6 Years Ago — What Should You Do Now? 18:53 – Audit Defense: The First 3 Things Victoria Looks At 19:46 – The Most Dangerous Assumptions Tax Pros Make 22:48 – Can Conservation Easements Still Work Legitimately in 2026? 23:38 – Rapid Fire: Wait or Be Proactive? 27:27 – The #1 Misconception Real Estate Investors Have 28:15 – Where to Find Victoria Boon and Boon Tax Group 29:43 – Outro & Listener CTA ━━━━━━━━━━━━━━━━━━━━━━━━ 💼 ABOUT DAVID WIENER ━━━━━━━━━━━━━━━━━━━━━━━━ David Wiener is the founder of Cash Flow Strategies and a nationally recognized cost segregation and tax strategy expert. Every week on The Tax Strategy Playbook, he breaks down the strategies real estate investors and business owners use to legally keep more of what they earn. 📩 Work with David: https://www.taxstrategyplaybook.com 💼 LinkedIn: https://www.linkedin.com/in/davidwiener ━━━━━━━━━━━━━━━━━━━━━━━━ ⚠️ DISCLAIMER ━━━━━━━━━━━━━━━━━━━━━━━━ This content is for educational and informational purposes only and does not constitute legal, tax, or financial advice. Consult a qualified tax professional before making any decisions related to your tax situation. #ConservationEasement #TaxStrategy #IRSAudit #RealEstateTax #TaxPlaybook

    Former IRS Agent: Why Syndicated Conservation Easements Are About to Blow Up

  6. Jun 16

    Bad Timing Costs You More Than Bad Investments Ever Will - The Cash Flow Clock

    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. 💡 WHAT YOU'LL LEARN IN THIS EPISODE: ✅ What the Cash Flow Clock is and how to apply it to your portfolio today ✅ Why bad TIMING — not bad investments — destroys most financial plans ✅ The "Lazy Zone," "Safe Zone," and "Volatility Zone" of cash flow planning ✅ How asset location (not just allocation) could save you hundreds of thousands in taxes ✅ Why deferring taxes forever is a trap — and how to time your tax bracket strategically ✅ The Widow's Tax Trap that blindsides surviving spouses at the worst moment ✅ When Roth conversions make sense (and when they don't) ✅ How cost segregation, bonus depreciation, and big deduction years fit into lifetime tax planning ✅ Why CPAs must shift from tax preparation to tax planning — and how to do it without overhauling their practice ✅ The first 3 steps any business owner or real estate investor should take in the next 30 days 🕐 CHAPTERS: 00:00 – Introduction: Why timing destroys good investments 02:12 – Meet Gary Preisser & Stonebriar Wealth Advisors 03:36 – The real villain: bad timing, not bad decisions 05:04 – Real client case study: $10M portfolio, wrong asset location 07:31 – Tax planning vs. tax preparation (why April 14th is too late) 10:42 – What is the Cash Flow Clock? (Plain English breakdown) 14:06 – Lifetime tax planning for business owners & real estate investors 17:19 – Selling a business, retiring, taking on partners — how to time it right 20:09 – How much do you really need to retire? (The right question) 21:24 – Cost segregation, bonus depreciation & tax lever strategy 24:51 – Roth conversions: who benefits and who doesn't 28:04 – A simple playbook for CPAs to start timing-first conversations 30:35 – How CPAs, financial advisors & tax specialists should collaborate 32:22 – One key takeaway for business owners, real estate investors & CPAs 🔗 CONNECT WITH GARY PREISSER: (See show notes for Gary's contact info and Stonebriar Wealth Advisors) 📩 FREE RESOURCES — Subscribe to the Tax Strategy Playbook Newsletter: 👉 https://taxstrategyplaybook.com/newsletter • 2026 Tax Planning Guide • Updates on every new episode • Free tax strategy resources for business owners and investors 🎙️ ABOUT THE TAX STRATEGY PLAYBOOK: Hosted by David Wiener — Mr. Cash Flow — the Tax Strategy Playbook breaks down real-world tax and cash flow strategies for business owners, real estate investors, and the CPAs who serve them. Every episode delivers actionable insights to help you keep more of what you make, smooth out your cash flow, and avoid the "I had no choice" moments the tax code loves to create. ⭐ If this episode helped you, please leave a rating and review — it helps more business owners and investors find this content! #TaxStrategy #CashFlowClock #RealEstateInvesting #TaxPlanning #BusinessOwner #RetirementPlanning #WealthManagement #RothConversion #CostSegregation #FinancialFreedom #TaxPlaybook #CPAs #PassiveIncome #AssetProtection #TaxReduction

    Bad Timing Costs You More Than Bad Investments Ever Will - The Cash Flow Clock

  7. Jun 9

    Former IRS Attorney Reveals 7 Real Estate Tax Traps Destroying Investor Wealth

    ⚠️ 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. Scott spent years INSIDE the IRS. He's seen both sides of the audit table. Now he's revealing exactly what the IRS looks for, what trips investors up, and how to legally protect your wealth before that audit letter ever shows up. ### ✅ FREE RESOURCE MENTIONED: Grab the Real Estate Investors Tax Pitfall Checklist & Record-Keeping Playbook — covers all 7 traps, what to audit in your own setup, and Scott's 3-Question Filter. 👉 Subscribe FREE at: taxstrategyplaybook.com/newsletter --- ### 🔗 CONNECT WITH SCOTT ESTILL: 🌐 Website: scottestill.com 💼 LinkedIn: Search "Scott Estill" --- ### 📌 TIMESTAMPS: 00:00 — Introduction: Why bad tax decisions crush investors 02:57 — Meet Scott Estill: Former IRS Senior Trial Attorney 03:30 — Trap #1: Record-Keeping Nightmares 09:22 — Trap #2: Entity Misalignment & Dealer Status Danger 21:33 — Trap #3: Self-Directed IRA Prohibited Transactions 33:40 — Trap #4: Travel & Education Documentation 36:23 — Trap #5: Dealer vs. Investor Status 40:08 — Trap #6: Tax Strategy vs. Exit Plan 44:36 — Trap #7: The 3-Question Filter 51:46 — Your Do-This-This-Week Checklist 52:43 — Where to Find Scott Estill --- ### 🎙️ ABOUT THE TAX STRATEGY PLAYBOOK: Hosted by David Wiener (Mr. Cash Flow), The Tax Strategy Playbook delivers practical, battle-tested strategies for real estate investors and business owners who want to keep more of what they earn and build durable, tax-efficient wealth. 📧 Newsletter: taxstrategyplaybook.com/newsletter 📺 Subscribe on YouTube | 🎧 Apple Podcasts | 🎵 Spotify

    Former IRS Attorney Reveals 7 Real Estate Tax Traps Destroying Investor Wealth

  8. Jun 2

    How Tired Landlords Are Escaping $1M Tax Bills Using DST 1031 (Without Buying Another Property)

    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 Statutory Trust (DST) advisory firms — to walk through exactly how investors are using DST 1031 exchanges and 721 UPREIT strategies to exit active real estate without writing a seven-figure check to the IRS. 🔑 What You'll Learn: ✅ What a Delaware Statutory Trust (DST) actually is — in plain English ✅ How to defer $800K+ in capital gains AND $300K in depreciation recapture using a 1031 exchange into a DST ✅ Why California landlords can lose up to 50% of their sale proceeds in taxes if they sell outright ✅ The real risks of DSTs that most advisors won't tell you about ✅ How a $3M commercial property sale was diversified across 6 DSTs for stable, passive income ✅ What a 721 UPREIT is and how it can provide a path to liquidity and estate planning advantages ✅ The "swap till you drop" strategy for lifetime tax deferral ✅ Who is (and isn't) a good candidate for the DST-to-UPREIT pathway ✅ The top questions to ask BEFORE you invest — and why your CPA needs to be in this conversation early 💡 Whether you're approaching retirement, burned out on property management, or just want your equity working harder without the headaches, this episode breaks down one of the most powerful — and underutilized — tax strategies available to real estate investors in 2026. 👉 Ready to explore your options? Visit kpi1031.com to access free DST resources, recorded webinars, and schedule a one-on-one call with Tommy and the Kay Properties team. 📌 Resources Mentioned: - Kay Properties & Investments: https://www.kpi1031.com - Schedule a Call with Tommy: https://www.kpi1031.com (click "Schedule a Call") - Tax Strategy Playbook Show Notes: https://www.taxstrategyplaybook.com 🔔 Subscribe for weekly deep dives on legal tax reduction, real estate strategy, and cash flow optimization for investors and business owners. 📧 Have a tax or deal structure question? Drop it in the comments — it might become our next episode! --- Disclaimer: This content is for educational purposes only and does not constitute financial, legal, or tax advice. Past performance does not guarantee future results. DST investments involve risk, including potential loss of principal. Consult a qualified tax advisor and financial professional before making investment decisions.

    How Tired Landlords Are Escaping $1M Tax Bills Using DST 1031 (Without Buying Another Property)
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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.

Information

  • Creator
    David Wiener, "Mr. Cash Flow"
  • Years Active
    2026
  • Episodes
    20
  • Rating
    Clean
  • Copyright
    © 2026 David Wiener, "Mr. Cash Flow"
  • Show Website
    The Tax Strategy Playbook

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