The Tax Strategy Playbook

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.

The Tax Strategy Playbook is a business podcast hosted by David Wiener, "Mr. Cash Flow", with 24 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

David Wiener, "Mr. Cash Flow" hosts The Tax Strategy Playbook, a business show with 24 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #22

  Tax Trouble: What To Do When Things Go Sideways

  Aug 4, 202645 min

  Got an unopened IRS letter in a drawer? Tax attorney Jason Wiggam breaks down exactly what to do when you owe the IRS and can't pay. We cover the first 3 things to do after any IRS notice, how installment agreements and offers in compromise actually work, when currently not collectible status makes sense, and why bankruptcy can sometimes wipe out tax debt. Jason Wiggam, founding partner of Wiggam Law in Atlanta, has helped hundreds of individuals and businesses resolve IRS and state tax debt without panic or shame. What you'll learn in this episode: - Why tax trouble happens to smart, successful people, not just "reckless" ones - The exact documents to gather before your first call with a tax attorney - How the IRS decides between an installment agreement, currently not collectible status, or an offer in compromise - Why only 15% of offers in compromise get accepted, and how to know if you'd qualify - Whether bankruptcy can legally discharge income tax debt - The 4-step Tax Strategy Playbook for going from IRS notice to full resolution If you're a real estate investor, business owner, or self-employed professional worried about an IRS letter, audit, or tax debt, this episode gives you a clear, no-shame plan. 0:00 Intro: What to Do When You Get an IRS Letter 2:17 Meet Jason Wiggam, Atlanta Tax Resolution Attorney 4:37 Who Really Ends Up in IRS Tax Trouble 7:21 Common Pathways Into IRS Tax Debt and Audits 8:59 The Danger of TikTok Tax Hacks and Bad Advice 11:48 Step 1: Open Your IRS Notice — Don't Ignore It 14:37 Documents to Gather Before Calling a Tax Attorney 18:04 IRS Installment Agreements: Full Pay vs Partial Pay 21:19 Currently Not Collectible Status Explained 22:53 Offer in Compromise: When It's Real vs Wishful Thinking 28:19 IRS Audits, Appeals, and US Tax Court 30:16 Should a CPA or Tax Attorney Handle Your Audit 35:08 Habits to Stay Off the IRS's Radar 38:15 Will You Go to Jail for Owing the IRS? (No) 40:20 The 4-Step Tax Resolution Playbook 44:06 Where to Reach Jason Wiggam / Wiggam Law ️ Listen to the full podcast: https://taxstrategyplaybook.com Get the free Tax Strategy Playbook newsletter: http://taxstrategyplaybook.com/newsletter Book a free cost segregation consultation: https://calendly.com/david-weiner/cs Contact David Wiener directly: david.wiener@cashflowstrategies.us or call 770-224-8504 ext. 2 Learn more about Jason Wiggam: wiggamlaw.com New episodes of The Tax Strategy Playbook drop every Tuesday — subscribe so you never miss a strategy that protects your cash flow. #IRSTaxDebt #TaxStrategyPlaybook #OfferInCompromise

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  Episode #21

  The Wealth Elevator: What Happens When You Actually Run the Numbers?

  Jul 28, 202641 min

  Most investors think they’re buying cash flow, but the ones who really build wealth know the deal either works after taxes, depreciation, and the exit… or it never worked at all. In this episode of The Tax Strategy Playbook, David Wiener (“Mr. Cash Flow”) and Lane Kawaoka (founder of The Wealth Elevator) rip apart the myths that keep real estate investors stuck in mediocre deals and show how high‑net‑worth investors really structure portfolios using syndications, alternative assets, and smarter underwriting. If you’ve ever looked at a proforma and thought, “This looks too good to be true,” this conversation will change how you read pitch decks, how you underwrite deals, and how you balance cash flow today against long‑term upside. You’ll hear why chasing a few thousand dollars a month in cash flow at a million‑dollar net worth is often a distraction, how to stop mistaking “activity” for “progress,” and how to build a portfolio that actually supports financial freedom instead of just more headaches. Lane shares his journey from engineer with 11 single‑family rentals to accredited investor allocating across large apartment syndications, private equity, oil and gas, and even T‑bills once you hit “critical mass.” You’ll hear exactly why he sold off his small rentals, reduced legal liability exposure, shifted into LP positions, and began underwriting deals using conservative, reality‑based assumptions instead of rosy operator spreadsheets. Inside this episode you’ll learn: Why most “cash flow” deals fall apart after taxes, depreciation, and realistic expenses. How accredited investors rebalance from small rentals into diversified commercial and alternative assets. The difference between activity vs. progress in your investing journey. How to underwrite syndication deals using PLs, rent rolls, and your own analyzer instead of trusting glossy pitch decks. When it makes sense to prioritize cash flow today vs. long‑term upside across dozens of deals. Why you may be better off in T‑bills or savings accounts than owning paid‑off rentals with low returns and full liability exposure. How the “Wealth Elevator” framework changes your strategy at each net‑worth floor—from under $1M to $4–5M+. FREE BOOK – THE WEALTH ELEVATOR Lane is giving away copies of his book “The Wealth Elevator” to listeners of this episode. Listen through for David’s instructions on how to claim your copy. Chapters: 00:00 – Why most investors overestimate cash flow and underestimate taxes 02:15 – Meet Lane Kawaoka: from engineer to accredited investor 05:11 – The Wealth Elevator: floors of the wealth game 05:51 – How beginners should underwrite single‑family rentals 10:21 – Legal liability and why many millionaires sell small rentals 10:57 – Shifting into LP positions and institutional assets 11:27 – Why pitch decks lie: PLs, rent rolls, and your own analyzer 13:02 – Balancing cash flow vs. long‑term upside in syndications 32:25 – Why “traction” in saving matters more than any single deal 33:19 – The one skill new investors must master: spreadsheet underwriting 35:26 – Redefining financial freedom at higher net‑worth levels If you care about what happens after the spreadsheet—and you want tax‑smart, risk‑aware strategies for building long‑term wealth—subscribe and turn on notifications so you never miss an episode of The Tax Strategy Playbook. #RealEstateInvesting #SyndicationDeals #PassiveIncome #TaxStrategy #AdvancedTaxPlanning #AccreditedInvestor #WealthBuilding #CashFlowInvesting #BonusDepreciation #CostSegregation #TheTaxStrategyPlaybook #WealthElevator #AlternativeInvestments #ApartmentSyndication #FinancialFreedom #AfterTaxCashFlow

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  Episode #20

  Cost Segregation Myths vs Reality | Which Owner Pays More?

  Jul 21, 202635 min

  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

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  Episode #19

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

  Jul 14, 202625 min

  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

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  Episode #18

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

  Jul 7, 202647 min

  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

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