Episodes

Democrats won Congress. Your 100% bonus depreciation didn't change. Three depreciation deadlines did not care who won, and one of them lands in 2026. In this solo news episode, David Wiener, Mr. Cash Flow, sorts every post-election tax headline into three buckets (law, proposal, or needs a signature) and walks through what the midterms mean for bonus depreciation, cost segregation, Section 179D, the R&D tax credit and the new qualified production property deduction for factory buildings under Se...

A charitable remainder trust lets you sell an appreciated building with no tax due at closing, reinvest every dollar, and collect income for life. The trade: what is left goes to a charity you pick, not your kids, and the tax does not disappear. It reaches you a slice at a time, in an order the tax code sets. In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, explains how a charitable remainder trust works in plain English: the charitable remainder annuity trust (CR...

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 pay...

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 servic...

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...

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 ...

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 sect...

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 ...

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 p...

Form 3115 is the four-page IRS form that lets you catch up every dollar of depreciation you should have taken on a rental or commercial building since the day it was placed in service, all on one current return, with no amended returns at all. Bought the property years ago and never had a cost segregation study done? You did not miss your window. In this episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, walks through the cost segregation look back study and the machinery behind...

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-directe...

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 ...

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 stu...

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...

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 ...

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 ...

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...

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. These are traps that can cost families six figures in avoidable taxes and legal fees. You'll learn: ✅ How step-up...

Unlock the Power of Opportunity Zones 2.0: A Tax Strategy Nobody's Talking About On July 4, 2025, the landscape of tax incentives for investors and business owners shifted dramatically with the passage of the One Big Beautiful Bill Act, which made Opportunity Zones a permanent fixture in the U.S. tax code. Just over a year later, on June 18, 2026, the IRS released Notice 2026-40, offering crucial transitional guidance for the evolution from Opportunity Zone 1.0 to the newly established Opportun...

Depreciation recapture is the bill that shows up when you sell a property you've depreciated, and a cost segregation study makes a bigger slice of it come back at ordinary income rates. That's not a reason to skip the study. It's a reason to plan the exit before you take the deduction. In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, walks through the back half of cost segregation that almost nobody talks about: what happens when you sell. What's covered: Why ev...

The IRS has recently announced a critical 90-day settlement window for syndicated conservation easements. After this period expires, participants could face a staggering 40% penalty and a near-complete loss of their claimed deductions. If you or your clients have ever been involved in a syndicated conservation easement, this episode is essential listening. Joining host David Wiener is Victoria Boon, a former IRS Senior Revenue Agent and Subject Matter Expert from the Large Business & Internat...

Bad Timing Costs You More Than Bad Investments Ever Will - The Cash Flow Clock On The Tax Strategy Playbook, host David Wiener, known as "Mr. Cash Flow," dives deep into a critical financial concept with guest Gary Preisser. Gary is the Managing Partner of Stonebriar Wealth Advisors and the innovative creator of the Cash Flow Clock, a revolutionary framework designed to help business owners, real estate investors, and their CPAs move beyond reactive tax planning to proactively design wealth tha...

Tax Traps. Most real estate investors often get crushed not by bad deals, but by poor tax decisions they weren't even aware of. This video features a former IRS senior trial attorney who shares insights on how common tax pitfalls, such as incorrect entity choices or inadequate documentation, can lead to significant financial losses during a tax audit. Understanding proper tax planning and tax strategies is crucial for business owners to avoid IRS red flags and protect their wealth. 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 7 real estate tax traps quietly destroying real estate investor wealth in 2026.

Tired Landlords: Escape $1M Tax Bills with a DST 1031 Exchange Are you a real estate investor feeling the exhaustion of active property management? Do the recurring challenges of tenants, toilets, and trash weigh on you, while the thought of selling your appreciated assets fills you with dread over massive capital gains and depreciation recapture taxes? If you're sitting on hundreds of thousands, or even millions, in potential tax liabilities, know that you're not alone, and there is a strate...