Tax Smart Real Estate Investors Podcast

Tax Smart Real Estate Investors Podcast

The Tax Smart Real Estate Investors Podcast is a show that focuses on tax, accounting, and finance tips for real estate investors and business owners. We bring on guests to talk through complex topics and we break it down into bite-sized chunks of knowledge for our listeners. Our episodes generally run 30-60 minutes of no-nonsense, hard-hitting information. We know your time is valuable so our goal is to save you thousands of dollars per episode. Hall CPA, PLLC is a CPA firm that exclusively serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch. Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information. Enjoy! The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor

Episodes

347. W-2 Tax Strategies in 2025: What's Actually Working

September 29, 2025 • 39 mins
In this episode of the Tax Smart REI Podcast, hosts Thomas Castelli and Ryan Carriere dive into one of the most-requested topics from high-income investors and professionals, W-2 tax strategies. Tune in to learn: - Why W-2 income is so highly taxed and the biggest obstacles to offsetting it - How Section 469 passive activity rules work and proven ways to navigate them with real estate professional status (REPS) or short-term rent...
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346. From Cockpit to Capital: Tax Strategies High W-2 Earners Need to Know with Tait Duryea

September 22, 2025 • 55 mins
From the cockpit to commercial real estate, Tait's story shows how a high-earning W-2 professional can build wealth outside of the stock market. In this episode of the Tax Smart REI Podcast, Tait shares the lessons he learned moving from single-family to multifamily to syndications and the strategies that help pilots and other professionals put their money to work more effectively. You'll learn: - How Tait’s early mistakes shaped...
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345. Estate Planning for Real Estate Investors (Trusts vs. Wills) with Attorney Diana Khan

September 15, 2025 • 31 mins
Estate planning is one of the most overlooked parts of real estate investing, but without it, your portfolio and family can be left exposed. This week on the Tax Smart REI Podcast, we sit down with attorney, broker, and investor Diana Khan to talk about how real estate investors should approach estate planning. You'll learn: - Why every investor needs at least a will and power of attorney (even at 18) - The difference between wil...
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344. Is a Condo or Single-Family Home Better for Maximizing Bonus Depreciation? (And More FAQ)

September 9, 2025 • 27 mins
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, answer real investor questions from the investing community, tackling some of the most pressing topics around bonus depreciation, short-term rentals, and advanced tax planning. Tune in to learn: - How cost segregation results differ between condos, single-family homes, and properties with big-ticket land improvements like pools - Why new renovat...
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343. 100% Bonus Is Back: Is Now the Time for a Short-Term Rental?

September 2, 2025 • 39 mins
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, break down the two most common questions investors are asking after the passage of the “Big Beautiful Bill” and the return of 100% bonus depreciation: - Should you invest in real estate or specifically short-term rentals for tax savings? - When does it make sense to start working with a tax strategist? Tune in to learn: - Why existing landlords...
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342. This Mistake Could Sink You in an IRS Audit with Justin Shore, EA

August 26, 2025 • 39 mins
In this episode of the Tax Smart REI Podcast, Thomas Castelli sits down with Hall CPA Advisory Manager Justin Shore to break down why bookkeeping isn’t just busy work, it’s the foundation of audit defense and financial success as a real estate investor. Tune in to learn: - Why sloppy bookkeeping can raise red flags and trigger IRS scrutiny - The key differences between Schedule E and Schedule C—and why they matter for your rental...
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341. From One Rental to $943K in Depreciation and Almost Zero Taxes with Zack Mattos

August 19, 2025 • 38 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with financial planner and short-term rental investor Zack Mattos to unpack how he went from a 20-year career focused solely on traditional retirement accounts to leveraging real estate to nearly eliminate his tax bill, including a staggering $943K in depreciation from one luxury rental property. Tune in to learn: - How he turned his Austin dream home into a h...
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340. From Chickens to Cashflow: Inside a $3.5M Lending Portfolio and 100+ Door Empire

August 12, 2025 • 37 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with entrepreneur and investor John Paul Houston to unpack his journey from running a backyard chicken operation to building a $3.5M private lending portfolio and a 100+ door real estate empire — all while dramatically reducing his tax bill by qualifying as a Real Estate Professional. Tune in to learn: - How John went from semi-retirement to scaling multiple i...
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339. Multiple Businesses, Major Write-Offs: Marty Geier’s Path to a $40K Taxable Income

August 5, 2025 • 49 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with entrepreneur and investor Marty Geier to unpack how he reduced his taxable income from $1.4 million to just $40K using a blend of business building, short-term rentals, and advanced tax strategy. Tune in to learn: - How Marty uses the 500-hour rule to make short-term rental losses non-passive and deductible - Why he starts a new business each year and how...
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338. The Truth About Infinite Banking: What You’re Not Being Told with Alex Savage CPA, CFP

July 29, 2025 • 46 mins
Before you commit to a whole life insurance policy, you need to understand what it really is and what it isn’t. This week on the Tax Smart REI Podcast, we sit down with financial planner Alex Savage, CPA and CFP, to break down the infinite banking concept and whether it truly makes sense for real estate investors and high-income earners. You'll learn: - What whole life insurance and infinite banking actually are (beyond the sales...
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337. Cost Segregation, REPS, and the $280K Wake-Up Call with Lauren Kraus

July 22, 2025 • 34 mins
Before you hire just any tax pro, you need to understand what a real estate-focused advisor can actually do for you. This week on the Tax Smart REI Podcast, we sit down with investor and developer Lauren Kraus to hear how working with a specialist helped her uncover over $280K in missed tax savings—and dramatically shift her investing strategy. You'll learn: - Why her CPA dismissed cost segregation (and why that was a $280K mista...
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336. The One Big Beautiful Bill Is Law: What You Need to Know Now

July 15, 2025 • 38 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down everything real estate investors and business owners need to know about the now-official “Big Beautiful Bill”, the sweeping tax package that just became law. Key topics covered: - 100% bonus depreciation is back and permanent: who qualifies and when it starts - QBI updates: simplified rules, new thresholds, and small business wins - SA...
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335. Syndication Legal 101: What Every First-Time Sponsor Must Know with Tilden Moschetti

July 6, 2025 • 35 mins
Before you syndicate your first deal, you need to get your legal foundation right. This week on the Tax Smart REI Podcast, we sit down with Tilden Moschetti, real estate attorney and experienced syndicator, to talk through the legal must-haves for your first capital raise. You'll learn: - When a deal becomes a syndication in the eyes of the SEC - The two-entity structure every sponsor should use - What PPMs, subscription agreement...
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334. Grouping Elections: Why Your STR Doesn’t Belong with Your LTRs

July 1, 2025 • 18 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas and Ryan answer real estate tax questions submitted by the community. From LLC structuring and grouping elections to retroactive cost segregation and solo 401(k) eligibility, this Q&A session covers some of the most common (and confusing) issues investors face midyear. Key topics covered: - Can I move my STR into an LLC if the deed and mortgage are in my name? - Why shor...
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333. The Senate’s version: Permanent 100% Bonus Depreciation

June 24, 2025 • 30 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, break down the Senate’s draft tax bill and what it could mean for real estate investors if it becomes law. Key topics covered: - 100% bonus depreciation made permanent: what this really means - Major changes to Qualified Opportunity Zones (QOZs) - Updates to Section 179 and interest expensing rules - The fate of the SALT cap and why it’s ...
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332. Can AI Replace Your Tax Advisor?

June 17, 2025 • 31 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, put ChatGPT to the test to answer a question that’s on the minds of many real estate investors: Can AI actually replace your tax advisor? Key topics covered: - Where AI like ChatGPT performs well and where it fails - Real-time testing of ChatGPT on short-term rental strategies - Common AI mistakes on REPS, depreciation, and passive loss r...
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331. The Overlooked Tax Move that Could Save You Tens of Thousands

June 10, 2025 • 18 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, dive deep into Partial Asset Dispositions (PADs), a powerful but often overlooked tax strategy that can unlock substantial savings for real estate investors during renovations. Key topics covered: - What a partial asset disposition (PAD) is and how it works - When and how to claim a PAD on your tax return - Using cost segregation studies ...
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330. What Your CPA Isn't Telling You (And It's Costing You Thousands) with Justin Shore

June 3, 2025 • 42 mins
In this episode of the Tax Smart REI Podcast, Thomas, Justin, and Ryan break down the most common (and costly) mistakes we see from other CPAs and the massive tax savings real estate investors are missing because of them. Tune in to learn: - Why electing out of bonus depreciation without knowing it can cost you tens of thousands - How improperly classifying repairs vs. improvements could trigger an audit or shrink your deductions...
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329. What Really Happens During an IRS Audit (and How to Win One) with Troy Silfies, CPA

May 27, 2025 • 44 mins
In this episode of the Tax Smart REI Podcast, Thomas, Troy, and Ryan unpack real IRS audit case studies involving real estate investors and break down exactly what happened, how they responded, and how they won. Tune in to learn: - What triggers IRS audits for short-term rentals and REPS (and how to avoid them) - The one thing most CPAs get wrong when representing clients in an audit - How a $209K tax bill was reduced to $296—wit...
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328. Inside the “One Big, Beautiful Bill” & How To Prepare for it with Nathan Sosa, CPA, MST

May 20, 2025 • 37 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down what real estate investors need to know about the draft of the 2025 tax bill, dubbed the “One Big, Beautiful Bill”, including what’s in it, what might change, and how to prepare for the opportunities it presents. Key topics covered: - The likely return of 100% bonus depreciation (and who qualifies) - SALT cap drama: why it could derail...
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