Episodes

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...

Tax Strategy vs TikTok Hacks: 7 Viral Myths That Trigger Audits Are you tired of scrolling through TikTok and seeing “tax hacks” and viral write-off tricks that could actually land you in hot water with the IRS? In this episode of The Tax Strategy Playbook, host David Wiener, also known as “Mr. Cash Flow,” cuts through the noise. He exposes 7 common social media tax myths that are actually audit bait and reveals the legitimate, long-term tax strategies that wealthy investors use instead. If yo...

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 Playbook, David Wiener (Mr. Cash Flow) and CPA M...

The short term rental tax loophole is how a high-income W-2 earner or business owner can use rental losses against wages and business income without qualifying as a real estate professional. Pair it with a cost segregation study and 100% bonus depreciation, and one property can produce a first-year loss big enough to matter on a six-figure return. In this episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, sits down with Ryan Bakke, CPA, real estate investor, and founder of Tax S...

The R&D tax credit is a dollar-for-dollar federal credit for businesses that solve technical problems, and most of the companies that qualify have never claimed it. No lab coats, no patents, and no research department required. If you run a manufacturer, a software company, an architecture or engineering firm, a construction company, or even a winery or brewery, and your people are paid to work through problems they don't already know how to solve, this episode is for you. In this episode of Th...

Section 179D is the energy efficient commercial buildings deduction, and it's one of the least understood tax breaks available to commercial building owners, developers, and the architects and engineers who design government and nonprofit buildings. The One Big Beautiful Bill Act ended it for buildings whose construction begins after June 30, 2026. Projects that began construction on or before that date can still qualify, and the deduction is claimed in the year the property is placed in service...

What if you could sell a rental property, defer 100% of your capital gains tax and depreciation recapture, and roll every dollar into a bigger, better deal, then keep doing it forever? That's exactly what a 1031 like-kind exchange allows real estate investors to do. In this episode of The Tax Strategy Playbook, host David Wiener sits down with Dave Foster, founder of The 1031 Investor and one of the country's leading experts on 1031 exchange strategies. Dave breaks down the exact rules, timelin...

This episode dives into how landlords use real estate to build durable wealth and tax efficiency, featuring investor, broker, and educator Christian Walsh. Christian shares his journey from traditional real estate work into becoming a trusted guide for everyday investors who want to play the game more strategically. He breaks down how to think like a long-term investor, why understanding local market dynamics matters more than chasing national headlines, and how to structure deals so they actually support your lifestyle and goals. You’ll hear practical examples of using leverage wisely, positioning yourself for opportunities in shifting markets, and avoiding the common mistakes that keep investors stuck. The conversation also touches on building a personal brand as an agent or advisor, communicating clearly with clients, and creating content that attracts serious investors instead of tire-kickers. By the end, listeners walk away with a clearer blueprint for growing a resili…