The Tax Strategy Playbook

David Wiener, "Mr. Cash Flow"
  • 5.0 (5)
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The Tax Strategy Playbook is where real estate investors and business owners learn how to stop overpaying the IRS and turn taxes into an opportunity center instead of an annual pain point. Each episode, host David Wiener (“Mr. Cash Flow”) sits down with CPAs, tax attorneys, cost segregation experts, and top investors to break down complex tax rules into clear, step‑by‑step strategies you can actually use. You’ll hear real case studies, before‑and‑after numbers, and practical checklists on things like cost segregation, bonus depreciation, real estate professional status, short‑term rental strategies, entity structure, and more—without legalese or fluff. Expect straight talk, tactical advice you can hand to your CPA, and simple action items at the end of every show so you always know what to do next.

  1. 2d ago

    Why Mobile Home Parks Are One of the Best Cost Segregation Assets in Real Estate

    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 of more than 500 pads across eight states, to walk through what a cost seg study finds on a park, what changed when the One Big Beautiful Bill Act made 100 percent bonus depreciation permanent, when to order the study, what the engineer needs on site, and a real acquisition where a $1.05 million park produced close to $800,000 in accelerated depreciation.   Built for the real estate investor who has passed on manufactured housing because it looked small next to an apartment complex, the passive investor weighing an operator's deal and the K-1 that comes with it, and the business owner or tax professional who wants to see exactly where the depreciation comes from on a land-heavy asset.   WHAT YOU WILL LEARN Why mobile home parks beat apartment buildings on cost segregation: land improvements, not a 27.5 year structure What a cost segregation study finds on a manufactured housing community: roads, utilities, pads, fencing, signage, and how park-owned homes push the number toward 80 percent 100% bonus depreciation under the One Big Beautiful Bill Act, and why the placed-in-service date controls, not the date of the study When to commission the study, what to hand the engineer, and why septic tanks and buried water lines need an on-site walkthrough with your contact How to vet an operator before you invest: why the jockey matters more than the horse, and the recourse and exit questions to ask CHAPTERS   Nothing in this episode is tax advice for your situation. Your numbers are your numbers and they need a professional who knows them. Tax evasion is a crime, but tax avoidance is mandatory.   Your host: David Wiener, "Mr. Cash Flow" https://davidhwiener.com David.wiener@cashflowstrategies.us 770-224-8504x2 Schedule a conversation or free consultation at https://calendly.com/david-wiener/initial-consultation Subscribe to The Tax Strategy Playbook Podcast Channel: https://www.youtube.com/@TaxStrategyPlaybookPodcast/?sub_confirmation=1 Get updates, special episodes and live streams, and free resources on the latest tax strategies: https://www.taxstrategyplaybook.com/newsletter/   #CostSegregation #MobileHomeParkInvesting #BonusDepreciation #RealEstateInvesting #TaxStrategyPlaybook

    Why Mobile Home Parks Are One of the Best Cost Segregation Assets in Real Estate

  2. Sep 15

    The EIDL Time Bomb: How the Treasury Is Now Seizing Refunds Without a Court Order

    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 The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, sits down with Phillip Zagotti, JD and CPA, founder of North Star Law Firm in Houston, to walk through what happens after an SBA loan default: who actually signed a personal guarantee, what the $25,000, $200,000 and $500,000 thresholds mean, why closing your business does not make the debt disappear, the 1099-C cancellation of debt surprise that follows EIDL loan forgiveness, the SBA offer in compromise window, and why Subchapter V bankruptcy may still be on the table even when the business is gone. This one is for the business owner who took an EIDL loan during COVID and assumed it was forgotten, the real estate investor whose operating company or rental business carried one, and the CPAs, EAs, and tax professionals who are about to get the call when a client's refund does not show up. Phillip Zagotti, JD and CPA, founder of North Star Law Firm, Houston. Admitted to the U.S. Tax Court, federal courts in Texas, and the California State Bar. His contact information is in the show notes at https://www.taxstrategyplaybook.com Nothing in this episode is tax or legal advice for your situation. Your facts are your facts and they need a professional who knows them. Your host: David Wiener, "Mr. Cash Flow" https://davidhwiener.com David.wiener@cashflowstrategies.us 770-224-8504x2 Schedule a conversation or free consultation at https://calendly.com/david-wiener/initial-consultation Subscribe to The Tax Strategy Playbook Podcast Channel: https://www.youtube.com/@TaxStrategyPlaybookPodcast/?sub_confirmation=1 Get updates, special episodes and live streams, and free resources on the latest tax strategies: https://www.taxstrategyplaybook.com/newsletter/   #EIDLLoan #EIDLDefault #SBALoan #TreasuryOffset #WageGarnishment #EIDLForgiveness #SmallBusiness #TaxStrategy #TaxStrategyPlaybook

    The EIDL Time Bomb: How the Treasury Is Now Seizing Refunds Without a Court Order

  3. Sep 8

    Bought Your Rental Years Ago? You Can Still Claim Every Missed Deduction

    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 change in accounting method, how bonus depreciation rates are locked in by the year your property went into service, and how to tell whether the catch-up is cash in your pocket this year or a suspended passive loss that waits.   Your host: David Wiener, "Mr. Cash Flow" https://davidhwiener.com David.wiener@cashflowstrategies.us 770-224-8504x2 Schedule a conversation or free consultation at https://calendly.com/david-wiener/initial-consultation Subscribe to The Tax Strategy Playbook Podcast Channel: https://www.youtube.com/@TaxStrategyPlaybookPodcast/?sub_confirmation=1 Get updates, special episodes and live streams, and free resources on the latest tax strategies: https://www.taxstrategyplaybook.com/newsletter/   #CostSegregation #Form3115 #RealEstateTax #BonusDepreciation #RentalProperty #TaxStrategy #RealEstateInvesting #DepreciationDeduction #TaxStrategyPlaybook

    Bought Your Rental Years Ago? You Can Still Claim Every Missed Deduction

  4. Sep 1

    Are You Breaking These Self-Directed IRA Rules? (Don't Find Out the Hard Way)

    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 traditional and Roth accounts alike), how a rollover from an old 401(k) really works, and why real estate investors love checkbook control through an IRA LLC. Then we get into the rules that can blow up the whole tax advantage. Daniel names the seven disqualified persons you can never transact with, explains why fixing your own rental's leaky faucet counts as a prohibited transaction, and tells the story of a client who called his son a "business partner" and learned that lesson the hard way. We also break down UBIT and UDFI without the jargon, including why a solo 401(k) sidesteps UDFI entirely and how depreciation and cost segregation fit in when your IRA buys property with a non-recourse loan. You'll hear real examples too: a 56-year-old running wholesale deals through a solo 401(k) so he can pull the profits out tax free in retirement, a group of Georgia investors who formed their own private lending bank from their retirement accounts, and a pilot whose Roth IRA bought a plane. We also dig into private money lending, why Daniel calls it the gateway drug of self-directed investing, and how to structure a note so your custodian can actually tell when it's in default. The episode closes with a five-step playbook for opening and funding your first self-directed IRA the right way. ⏱️ CHAPTERS 00:00 [Add chapters after upload] Know a real estate investor or business owner with an old 401(k) collecting dust? Send them this episode. It might be the most profitable thing they watch all year. Subscribe to the newsletter for free resources, including my 2026 tax planning guide and a check sheet for every episode: https://www.taxstrategyplaybook.com/newsletter And if this opened your eyes to money you didn't know you could use, share it with one investor or business owner who needs to see it. Connect with Daniel Tercey at Directed IRA: https://directedira.com Full show notes: https://www.taxstrategyplaybook.com #SelfDirectedIRA #RealEstateInvesting #TaxStrategy #RetirementPlanning

    Are You Breaking These Self-Directed IRA Rules? (Don't Find Out the Hard Way)

  5. Aug 25

    Cost Segregation Can't Save a Bad Real Estate Deal (Here's What It Actually Does)

    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 it creates, and the bill that shows up later that nobody online mentions. What's covered: Why cost segregation is a timing tool, not free money. It moves write-offs you were always going to get from year 15 up into year one. Useful, yes. The same as creating value, no. How 100% bonus depreciation changed the math, and why a 27.5-year versus a 39-year depreciation schedule catches short-term rental owners off guard. Depreciation recapture, the part that never makes the Reddit thread. Building write-offs come back at a rate capped around 25%. The pieces a study carves out come back at ordinary income rates as high as 37%, plus net investment income tax in some cases. Passive loss rules. By default these losses get parked until you have rental income to offset or you sell. Two ways to use them now: qualifying as a real estate professional, or the short-term rental rules for properties with an average stay of seven days or less that you actively run. A full worked example on a $500,000 short-term rental. $100,000 land, $400,000 building, a study that finds 25%, roughly $97,000 of extra year-one write-off and about $36,000 in tax savings at the top bracket. Same study, two deals. On a marginal property it flips an $8,000 annual loss into roughly $28,000 in your pocket. On a property bleeding $40,000 a year, you're still underwater, and by year two the cushion is gone. The five-step test to run before you sign a contract, including the zero benefit question that settles it in ten minutes. Cost segregation studies referenced here are engineering-based and delivered through CSSI. ⏱️ CHAPTERS 00:00 [Add chapters after upload] Want to know whether a specific property belongs in the cost seg pile or the walk-away pile? I'll run a no-cost preliminary analysis on any property you own or are considering. No obligation, no pitch, and if a study won't pay for itself, I'll tell you that. Book a time: https://calendly.com/david-wiener/cs Or call 720-224-8504, option two. Know an investor three tabs deep into a Reddit thread talking themselves into a marginal deal? Send them this one. Free breakdowns like this in your inbox, plus playbook notes for every episode and my 2026 tax planning guide: https://www.taxstrategyplaybook.com/newsletter More from the show: https://www.taxstrategyplaybook.com If it was useful, pass it to one investor or business owner underwriting a deal right now. #CostSegregation #RealEstateInvesting #TaxStrategy #ShortTermRental #BonusDepreciation

    Cost Segregation Can't Save a Bad Real Estate Deal (Here's What It Actually Does)

  6. Aug 18

    Cost Segregation Audit: The 5 Documents That Save You

    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 elements of a quality cost segregation study • The exact 5 documents that turn an IDR into a formality, not a fight • What happens when a study can't hold up: reclassification, deferred tax, and a 20% accuracy-related penalty • Your taxpayer rights during an audit, including representation and IRS appeals Chapters: 0:00 Intro – The Letter Every Investor Fears 0:45 Why Cost Segregation Studies Draw IRS Attention 2:18 IRS Audit Techniques Guide (Publication 5653) Explained 3:16 The 13 Elements of a Quality Cost Segregation Study 4:37 What an IRS Examiner Actually Checks First 6:42 The 5 Documents That Turn an Audit Into a Formality 8:45 Inside an IRS Cost Segregation Audit, Step by Step 11:07 The 20% Accuracy-Related Penalty Explained 12:33 Investor A vs Investor B: Same Deduction, Opposite Outcomes 16:43 3 Steps to Pass a Cost Segregation Audit Before It Happens 19:01 Anatomy of a Losing Cost Segregation Study 21:56 Listener Q&A: Does Cost Seg Increase Audit Risk? Your host: David Wiener, "Mr. Cash Flow" 📧 David.wiener@cashflowstrategies.us 📞 770-224-8504 ext. 2 Schedule a conversation or free consultation: https://calendly.com/david-wiener/initial-consultation Subscribe to The Tax Strategy Playbook Podcast Channel: https://www.youtube.com/@TaxStrategyPlaybookPodcast/?sub_confirmation=1 Get updates, special episodes, live streams, and free tax strategy resources: https://www.taxstrategyplaybook.com/newsletter/ #CostSegregationAudit #IRSAudit #TaxStrategyPlaybook #RealEstateInvesting #CostSegregation

    Cost Segregation Audit: The 5 Documents That Save You

  7. Aug 11

    Sophisticated Investors Do This Before Selling Property

    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 tax planning, practical steps for tax planning, mindset shift in tax planning, actionable steps for tax planning, and finding expert advice. Takeaways Tax strategy shapes investment decisionsPlanning for taxes is crucial for long-term wealth Real estate investment options vary in terms of tax benefits and investment strategies.Understanding the differences between DST, 1031 exchange, and opportunity zones is crucial for informed decision-making. Chapters 00:00 Tax Strategy and Investment Decisions02:14 Tax Mitigation and Exit Planning03:05 Planning for Taxes vs. Reacting to Taxes05:10 Long-Term Wealth and Tax Strategy06:39 Cost Segregation and Cash Flow Maximization09:09 1031 Exchanges and Strategic Moves12:18 Challenges of 1031 Exchanges14:59 Pivoting and Changing Plans17:24 Delaware Statutory Trusts (DSTs)24:09 Real Estate Investment Options25:12 Comparing Investment Options25:27 Understanding Opportunity Zones29:18 Exploring Alternative Strategies35:04 Customized Tax Planning39:08 Practical Steps for Tax Planning43:51 Mindset Shift in Tax Planning44:44 Actionable Steps for Tax Planning46:15 Finding Expert Advice

    Sophisticated Investors Do This Before Selling Property

  8. Aug 4

    Tax Trouble: What To Do When Things Go Sideways

    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

    Tax Trouble: What To Do When Things Go Sideways
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About

The Tax Strategy Playbook is where real estate investors and business owners learn how to stop overpaying the IRS and turn taxes into an opportunity center instead of an annual pain point. Each episode, host David Wiener (“Mr. Cash Flow”) sits down with CPAs, tax attorneys, cost segregation experts, and top investors to break down complex tax rules into clear, step‑by‑step strategies you can actually use. You’ll hear real case studies, before‑and‑after numbers, and practical checklists on things like cost segregation, bonus depreciation, real estate professional status, short‑term rental strategies, entity structure, and more—without legalese or fluff. Expect straight talk, tactical advice you can hand to your CPA, and simple action items at the end of every show so you always know what to do next.

Information

  • Creator
    David Wiener, "Mr. Cash Flow"
  • Years Active
    2026
  • Episodes
    29
  • Rating
    Clean
  • Copyright
    © 2026 David Wiener, "Mr. Cash Flow"
  • Show Website
    The Tax Strategy Playbook

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