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 worke...

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 cou...

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 develo...

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 n...

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,...

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 pu...

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, administrati...

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 Fl...

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 a...

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...

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 penaltie...

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 Tr...

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...

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‑...

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,...

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 c...

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 m...

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 ow...

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 &...

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 work...

⚠️ 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...

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...

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, t...

Here’s a revised YouTube description with a first paragraph that’s intentionally loaded with relevant keywords while still reading naturally. 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 dril...

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 depreciati...