The Tax Strategy Playbook

Getting paid by a client won't cost you the R&D tax credit. Your contract can. Two tests decide whose credit it is when a client pays for the work. In part two of a four-part solo series on the research and development tax credit, David Wiener, Mr. Cash Flow, walks through the funded research rule in plain English. The risk test asks whether you were going to be paid whether the research worked or not. The rights test asks whether you can use what you figured out in your own business without paying the client for it. You...

Rental property depreciation is the one deduction the IRS counts against you whether you take it or not. Here's how yours is calculated, line by line.

In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, walks through real estate depreciation from the beginning. You'll see what goes into your cost basis and what stays out, how to split land from building using your county assessor's ratio instead of a flat 20 percent guess, why the clock starts on the placed in service date (the day the property is ready and available f...

The R&D tax credit can pay a startup that is losing money, through payroll taxes it already owes. Miss one box or one date and the cash waits, or never comes.

Most small business tax credits aren't hidden. They're missed, because every one of them runs on a clock. In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, opens a four-part series on the research and development tax credit with the question founders ask most: we don't make money yet, does any of this help us? It does. A qualified small...

Cost segregation is a real estate tax deduction many of the largest property owners never use. The reason has nothing to do with money. David Wiener, Mr. Cash Flow, sits down with DJ Van Keuren, founder of the Family Office Real Estate Institute and co-founder of Evergreen Property Partners, who has spent 25 years inside family office real estate. They cover why a cost segregation study so often never reaches the people who make the decisions, who actually brings a new tax strategy to a wealthy family, why DJ's annual family office study finds about 80 percent of families do not...

The 179D deduction did not die on June 30, 2026. The energy efficient commercial building deduction closed to new projects that begin construction after that date, and that is the entire loss. Every commercial building already placed in service still qualifies, and so does every project that broke ground before July 1. If you own a warehouse, office, hotel, self storage facility, medical building, or an apartment building four stories or taller placed in service since 2006 and never claimed section 179D on it, you can catch the whole deduction up on your current return through Form 3115, change number 152, without amending a single...

Mobile home park investing has a cost segregation edge most real estate investors never see. On most manufactured housing communities the operator owns the land and the residents own their homes, so nearly the whole purchase price sits in roads, utility lines, pads, and site work instead of a 27.5 year building. Run an engineering-based cost segregation study on that and 40 to 80 percent of the purchase price can land in 15-year land improvements that qualify for 100% bonus depreciation in year one. David Wiener, Mr. Cash Flow, sits down with Leo Young, founder and managing partner of Cornell Communities, an operator...

Took a COVID EIDL loan and have not thought about it in years? Check your status today. In late March the SBA moved hundreds of thousands of non-performing EIDL and PPP loans to the Treasury Department for enhanced collection, the hardship payment plans ended, and an EIDL loan default now gets collected like any other federal debt. The Treasury Offset Program can take your tax refund, administrative wage garnishment can take up to 15 percent of your paycheck, and a collection fee of roughly 30 percent gets added to the balance. No lawsuit, no day in court. In this episode of...

Bought your rental years ago and never had a cost segregation study done? You did not miss your window. There is a four-page IRS form, Form 3115, that lets you catch up every dollar of depreciation you should have taken since the day the property was placed in service, all on one current return, with no amended returns at all.

In this episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, breaks down the cost segregation look back study, the Section 481(a) catch-up adjustment, why the three-year amended return clock does not apply to...

A self-directed IRA lets you use old retirement money to buy real estate, fund private loans, and invest in businesses, tax deferred or even tax free. Most investors have never been told this account exists. That old 401(k) from a job you left years ago? It could be working a lot harder for you.

In this episode of The Tax Strategy Playbook, I sit down with Daniel Tercey, senior account executive at Directed IRA, to walk through the whole roadmap in plain English. You'll learn what "self-directed" actually means (it's a marketing term, and it applies to...

Can a cost segregation study rescue a bad real estate deal? No. But cost segregation can turn a marginal rental property into a genuinely good one for the right investor, and this episode shows exactly where that line sits, with real numbers.

It started with a Reddit post: close on the deal, do a cost seg study, and let the depreciation bail you out. Hundreds of upvotes. It's wrong, and believing it can cost you real money. David Wiener, Mr. Cashflow, breaks down what a cost seg study actually does, who can use the losses...

A cost segregation audit isn't an accusation — it's a request for proof. Here's the IRS's own checklist (Pub. 5653) so your study passes every time.

David Wiener breaks down the IRS Cost Segregation Audit Techniques Guide (Publication 5653) and the 13 elements examiners use to evaluate every study. You'll see exactly what an information document request looks like and why accuracy-related penalties can turn a saved deduction into a five-figure loss.

What you'll learn:
• Why cost segregation studies draw a second look (and why a $20K-to-$300K swing isn't the red flag people assume)
• The IRS's own 13...

The conversation explores the critical role of tax strategy in investment decisions, emphasizing the importance of tax mitigation and exit planning. It delves into the distinction between planning for taxes and reacting to taxes, highlighting the impact of tax strategy on long-term wealth. Additionally, it discusses cost segregation, 1031 exchanges, challenges, and the use of Delaware Statutory Trusts (DSTs) as an alternative option. The conversation covers various real estate investment options, including DST, 1031 exchange, and opportunity zones. It delves into the comparison of these options, the understanding of opportunity zones, and the exploration of alternative strategies. It also discusses customized...

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:

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,” thi...

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...

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 deprecia...

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...

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...

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 Ed...

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 investmen...

⚠️ 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 leg...

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...

Tired of TikTok “tax hacks” and viral write‑off tricks that could actually trigger an IRS audit? In this Tax Strategy Playbook episode, David Wiener (Mr. Cash Flow) exposes 7 social media tax myths and shows you the real 2026 tax strategy wealthy investors use instead.

If you’re serious about long‑term tax planning, bonus depreciation, cost segregation, and keeping more cash flow in your pocket, this is your playbook.

In this episode, David explains why the IRS added misleading social media tax advice to its 2026 Dirty Dozen list of tax scams and how Americans are losing ten...

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If you’re a high-income W-2 earner, 1099 professional, real estate investor, or business owner looking for advanced tax strategies to reduce taxes, this episode breaks down a powerful oil and gas tax strategy to legally offset W-2 income, use intangible drilling costs (IDC) deductions, and stack oil and gas investing with cost segregation and other tax planning moves to cut your IRS bill and increase cash flow.

In this episode of The Tax Strategy Playbo...

Real estate tax strategy with short-term rentals is one of the most powerful ways high-income W‑2 earners and business owners can legally slash their tax bill without real estate professional status. In this episode of The Tax Strategy Playbook, David Wiener (Mr. Cash Flow) and CPA/investor Ryan Bakke break down how to use the short-term rental “loophole” plus cost segregation and bonus depreciation to offset W‑2 and business income in year one

$100K+ R&D TAX CREDIT 2026 EXPOSED – The Secret Dollar-for-Dollar IRS Tax Credit You’re Quietly Donating Every Year! Construction Tax Credits, Manufacturing Tax Credits, Software Development Tax Credit, Architecture & Engineering Tax Savings, Winery R&D Credits, Brewery Tax Credits, Law Firm Tax Hacks & More – NO Lab Coats, NO Patents, NO Billion-Dollar Tech Company Needed! Business Owners & Entrepreneurs Are Claiming Massive Tax Strategy Wins in 2026! Are you accidentally leaving $100,000 or more in legal R&D tax credits on the table every year? Most business owners have no idea they qualify — even if they run a construction company, manufacturing plant, software business...

In this eye-opening episode of the Tax Strategy Playbook, David Wiener (Mr. Cash Flow) sits down with 179D expert Brian Broussard to reveal how commercial building owners, developers, and designers can still claim massive Section 179D energy-efficient tax deductions before the June 30, 2026 deadline under the One Big Beautiful Bill. Discover who qualifies, how the deduction works on new builds and renovations, real-world six- and seven-figure success stories, and how pairing 179D with cost segregation studies can supercharge your first-year tax savings. Whether you own offices, hotels, warehouses, or design government/non-profit facilities, this is the window to turn energy...

Real estate investors: stop writing massive checks to the IRS!

Learn how a 1031 like-kind exchange lets you sell property, defer 100% of capital gains tax + depreciation recapture, and roll every dollar into bigger, better deals — forever. Dave Foster (The 1031 Investor) reveals the exact rules, timelines, strategies, and generational wealth hacks every investor needs to know.

Landlords Don’t Have a Tax Problem—It's a STRATEGY Problem Killing Cash Flow

Most landlords think they’re overpaying taxes. The truth? Their properties, tenant laws, and tax code are all pulling in opposite directions — quietly destroying cash flow and passive income.

In this episode of The Tax Strategy Playbook, David Wiener sits down with top real estate broker Christian Walsh to expose the biggest rental portfolio mistakes investors make nationwide — from the dangerous “never sell” myth to silent cash-flow killers like insurance, HOA fees, property taxes, poor management, and terrible retur...

Most business owners and real estate investors are about to sleepwalk past the biggest tax opportunity of the decade—and the IRS is counting on it.

In this episode of The Tax Strategy Playbook, host David Wiener breaks down the 2025 “One Big Beautiful Bill” and shows you, step by step, how to turn this new tax law into a weapon instead of a hammer.

If you own a business, rentals, or both, this is not another boring tax update. It’s a playbook you can literally take to your CPA.

Most real estate investors assume a cost segregation study automatically creates a tax win. But if the IRS sees your rental as passive, those losses may not offset your W-2 or business income the way you expected. In this episode, David Wiener and Gabriel Virdaru break down passive vs. active real estate in plain English, explain real estate professional status, and show how material participation can unlock serious tax savings.

We also cover:

• What counts as passive income vs. active income.

• Why many investors misunderstand real estate professional status.

• How material partic...

You’re about to find out whether your LLC or S corp is quietly costing you thousands in taxes.

In this episode of The Tax Strategy Playbook, host David Wiener sits down with Matt Bontrager, CPA, managing partner of TrueBooks, a firm that works almost exclusively with real estate investors and entrepreneurs. Matt has seen hundreds of real‑world structures—good, bad, and ugly—and he pulls back the curtain on how entity decisions actually impact your tax bill, liability protection, and future flexibility.

🔑 In this episode, you’ll learn:

This episode delves into the concept of cost segregation and bonus depreciation in real estate, explaining how it works, its benefits, myths, and considerations for choosing a quality cost segregation firm. The episode provides practical insights for property owners and investors to optimize their tax planning and cash flow.

Takeaways

Stop letting the IRS be your biggest business partner. In this first episode of The Tax Strategy Playbook, host David Wiener (“Mr. Cash Flow”) sits down with tax strategist Greg Taylor to unpack the real reasons real estate investors and business owners quietly overpay the IRS year after year—and what to do about it.

Greg is the founder of Taylor Tax Strategy, where he helps investors and entrepreneurs use proactive planning to legally reduce their tax bill and keep more cash working inside their portfolios.

In this conversation, Greg shares his jo...