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

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

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

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

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

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 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

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📌 CHAPTERS

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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

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💼 ABOUT DAVID WIENER

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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

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⚠️ DISCLAIMER

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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

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