The Tax Strategy Playbook

David Wiener, "Mr. Cash Flow"
  • 5.0 (5)
  • Investing

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. 2h ago

    Rental Property Depreciation Explained: How It's Calculated

    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 for rent) instead of the closing date, and how the mid-month convention shapes your first year. If you've ever searched how to calculate depreciation on rental property, the duplex example in this episode is the whole answer.   Then David takes apart the advice to skip depreciation so you won't owe tax when you sell. The IRS lowers your basis by the depreciation allowed or allowable, whichever is greater, so the deduction you skipped still counts against you at the sale. Of all your rental property tax deductions, depreciation is the one that never costs you a check, and it still matters on a rental that shows a loss.   Built for the investor with one to five rentals who has never looked at the depreciation line on their own return, the business owner who owns or is buying a rental or the building their company runs out of, and the tax professional who wants a plain English version to hand a client. It also covers converted homes, inherited rentals, short-term rentals (where 27.5 versus 39 years is a judgment call your tax professional makes), and when an engineering-based cost segregation study, with an in-person site visit, moves parts of the building onto 5, 7, and 15 year schedules. Every dollar figure in the episode is an illustration, not a client.   CHAPTERS 00:00 What is rental property depreciation? 27.5 vs 39 years explained 05:12 How to find your cost basis and split land from building 10:11 When does depreciation start on a rental? Placed in service and the mid-month convention 13:12 How to calculate depreciation on rental property: a duplex example 17:39 Repairs vs improvements: de minimis safe harbor and the old roof problem 21:33 Do you have to depreciate rental property? Allowed or allowable and passive losses 25:12 Depreciation on a converted home, inherited rental, short-term rental, or business building 28:37 Cost segregation and 100% bonus depreciation on a rental property 33:34 Rental property depreciation FAQ 37:06 Your rental property depreciation playbook: five steps this week   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/   #RentalPropertyDepreciation #RealEstateDepreciation #RentalPropertyTaxDeductions #CostSegregation #TaxStrategyPlaybook

    Rental Property Depreciation Explained: How It's Calculated

  2. Oct 13

    R&D Tax Credit for Startups: Get Paid Even If You're Losing Money

    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 business, one under $5 million in gross receipts and within its first five years of receipts, can elect to use up to $500,000 a year of R&D credit against the employer share of Social Security and Medicare. David walks through the three clocks that decide whether that money shows up and when, including how a filing date moved one startup's $90,000 by nine months. Then the lens widens to the tax credits for businesses with employees: the SECURE 2.0 retirement plan credits, worth about $65,000 over five years for one 18-person company, the small employer health care credit, the paid family and medical leave credit that changed for 2026, and the credits that are gone for 2026 hires. Built for the founder or CFO of a young company paying engineers, developers or designers and not yet profitable, the owner of an established business with 10, 20 or 50 employees who has never been walked through the credits that come with having them, and the tax professional who wants to know where the traps sit in the middle of extension season. CHAPTERS: 00:00 Small business tax credits: why they're missed, not hidden 03:50 Tax credit vs tax deduction: which one saves you more 05:53 What qualifies for the R&D tax credit (no lab required) 09:20 R&D tax credit for startups: using it against payroll taxes 10:37 Who qualifies for the R&D payroll tax offset: the $5 million and five-year tests 14:24 When does the R&D payroll credit start? The filing date that costs nine months 18:06 R&D tax credit example: a 12-person startup's $90,000, quarter by quarter 22:28 Retirement plan tax credits for small business: SECURE 2.0 and Form 8881 25:45 Small business health care tax credit and the paid family leave credit for 2026 29:33 Is the Work Opportunity Tax Credit gone? FAQ and the Playbook Nothing in this episode is tax advice for your situation. Your facts are your facts, and they need a professional who knows them, so work with your own tax professional. Tax evasion is a crime, but tax avoidance is mandatory. Your host: David Wiener, "Mr. Cash Flow" https://davidhwiener.com David.wiener@cashflowstrategies.us 770-224-8504, option two Book a no-cost analysis. No obligation, no pitch, and David will tell you if a study won't pay for itself: https://calendly.com/david-wiener/cs 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/ #RDTaxCredit #SmallBusinessTaxCredits #StartupTaxes #PayrollTaxCredit #TaxStrategyPlaybook

    R&D Tax Credit for Startups: Get Paid Even If You're Losing Money

  3. Oct 6

    Why Nobody on Your Team Has Mentioned Cost Segregation

    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 do 1031 exchanges, how 100% bonus depreciation changes the math when a deal is underwritten, how depreciation recapture works when you sell, and when not to do a cost segregation study at all. Built for the real estate investor who assumes a bigger portfolio means better tax planning, the business owner who owns the building the company runs out of and has never had anyone look at it closely, and the tax professional who knows how cost segregation works and wants a 25-year view of how these conversations start inside a family office, and who starts them. WHAT YOU WILL LEARN Why a missed cost segregation study is usually an oversight, not a decision, and who is most likely to raise it How wealthy families pick advisors by trust, and why a bigger team can mean fewer tax strategies reach you The five types of family office real estate investors and which ones have someone watching for cost seg When not to do a cost segregation study: a short hold, a sale without a 1031 exchange, losses you cannot use yet Why tax benefits belong in the real estate underwriting model, and how depreciation recapture works on the way out CHAPTERS 00:00 Same tax code, different outcome: why big real estate owners miss cost segregation 03:03 What is cost segregation? 27.5 and 39 years vs 5, 7, and 15 year property explained 04:39 Why family offices underuse cost segregation, and what the callers asked 05:56 Missed tax strategy: a decision or an oversight? Who wealthy families trust 09:20 The five types of family office real estate investors and who handles cost seg 13:18 How many families skip 1031 exchanges and opportunity zones 18:24 When not to do a cost segregation study: short holds, small properties, passive losses 20:30 Bonus depreciation in the underwriting model: how tax benefits change real estate returns 24:26 Depreciation recapture, 1031 exchanges, and why cost seg cannot fix a bad deal 29:24 Your cost segregation playbook: the question to ask your tax professional this week 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 770-224-8504, option two Book a no-cost analysis. No obligation, no pitch, and David will tell you if a study won't pay for itself: https://calendly.com/david-wiener/cs 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 #FamilyOffice #RealEstateTaxStrategies #RealEstateInvesting #TaxStrategyPlaybook

    Why Nobody on Your Team Has Mentioned Cost Segregation

  4. Sep 29

    179D Is Not Dead: Claim It on a Building You Have Owned for Years

    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 old year. David Wiener, Mr. Cash Flow, walks both doors: the 179D tax deduction rates by year, from a flat $1.80 a square foot before 2023 to the 2026 scale of $0.59 to $1.19 base and $2.97 to $5.94 with prevailing wage, Form 7205 and the engineering certification behind it, the 179D allocation letter that hands the deduction to architects and engineers, and why 179D and cost segregation pull from two different piles on the same building.   Built for three people. The owner or investor who never claimed 179D on a building or a renovation. The developer whose project was underway this spring and finishes years from now. And the architects and engineers who design for schools, cities, hospitals and universities, because your version runs on a three year clock, not a twenty year one.

    179D Is Not Dead: Claim It on a Building You Have Owned for Years

  5. Sep 22

    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 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 770-224-8504, option two Book a no-cost analysis. No obligation, no pitch, and David will tell you if a study won't pay for itself: https://calendly.com/david-wiener/cs 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

  6. 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 770-224-8504, option two Book a no-cost analysis. No obligation, no pitch, and David will tell you if a study won't pay for itself: https://calendly.com/david-wiener/cs 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

  7. 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

  8. 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)
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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
    33
  • Rating
    Clean
  • Copyright
    © 2026 David Wiener, "Mr. Cash Flow"
  • Show Website
    The Tax Strategy Playbook

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