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 and www.TaxSmartInvestors.com/Insiders for more free content and information. Enjoy!

Episodes

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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327. 2025 Tax Bill Preview: Bonus Depreciation, SALT Cap Changes, and Investor Q&A

May 13, 2025 • 30 mins
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere break down what real estate investors need to know about the upcoming 2025 tax bill, including where it stands, what’s likely to be included, and how it could impact your bottom line. Key topics covered: - Expected return of 100% bonus depreciation - Potential changes to the SALT deduction cap - How to properly log hours for REPS (Real Estate P...
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326. What to Do Now that Tax Day is Over + Answering Your Pressing Questions

May 7, 2025 • 24 mins
In this post 4/15 recap, Thomas and Ryan reflect on the key themes and expert interviews from the year so far, from tiny homes to creative finance, and reinforce a common truth: smart investing still works in today’s market if you stay focused and play the long game. They also dive into what’s happening with the 2025 tax bill, including the outlook on 100% bonus depreciation, and answer real investor questions from email and the T...
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325. Why Now Might Be Multifamily’s Biggest Opportunity Yet with Michael Blank

May 6, 2025 • 37 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with multifamily syndication expert Michael Blank to unpack why 2025 may be one of the best times in years to get started—or scale—in multifamily real estate. Tune in to learn: - Why today’s market conditions offer lower risk and higher long-term upside. - How Michael bounced back from losing millions to build a $300M multifamily portfolio. - What’s really dri...
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324. Which Boring Strategy Still Wins in 2025? With Henry Washington

April 29, 2025 • 29 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with seasoned real estate investor and author Henry Washington to discuss why he’s not chasing creative finance trends, and why his “boring” strategy continues to deliver results in 2025’s unpredictable market. Tune in to learn: - Why Henry sticks with off-market deals and direct mail (even in the age of AI). - How he adjusts his strategy based on market cycles...
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323. 2025 Market Volatility: What Real Estate Investors Need to Know with Connor Low

April 22, 2025 • 38 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan talk with wealth manager Connor Low, founder of Iarann Wealth, about how today’s economic uncertainty, from global tariffs to interest rate swings, is impacting investors, and what real estate investors should be doing about it. Connor breaks down the current market landscape, explains why panic is rarely a productive move, and shares how both real estate and equity inv...
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322. Real Estate Investor Case Studies: How One Client Saved $285K in One Year

April 15, 2025 • 36 mins
In this episode, Thomas and Ryan share real-life case studies from real estate investors who used strategic tax planning to save thousands, sometimes hundreds of thousands, on their tax bills. They also reveal the most common mistakes and missed opportunities they see from investors who waited too long or relied on the wrong advice. This episode explores: - How one couple saved $285K in a single year using REPS and cost segregati...
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321. Does Travel Time Count Toward Material Participation?

April 10, 2025 • 21 mins
In this Q&A episode, Ryan and Thomas answer real estate investors’ most pressing tax questions. From short-term rental loopholes to QBI deductions, they break down some of the most misunderstood topics in real estate tax strategy and provide practical, real-world guidance. They discuss: - STR Losses & NOLs - Travel Time & Material Participation - QBI Safe Harbor - STR Conversions Mid-Year - Bonus Depreciation Recapture - Home Imp...
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320. How Creative Financing Helps RE Investors Succeed in Every Market Cycle w/ Chris Prefontaine

April 8, 2025 • 30 mins
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere are joined by Chris Prefontaine, real estate veteran, founder of Smart Real Estate Coach, and leader of the Wicked Smart Community. Chris brings over three decades of experience to the table and breaks down how to invest without banks, structure zero-interest seller financing deals, and navigate subject-to transactions with confidence. You'll also hear...
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319. 3 Tax Scams to Watch Out for in 2025 (And 2 Risky Strategies to Avoid)

April 1, 2025 • 27 mins
In this episode, Thomas and Ryan break down some of the most common tax scams and questionable strategies being promoted to real estate investors—and how to avoid falling into these costly traps. This episode explores: - Why equipment leasing deals promising non-passive losses are almost always too good to be true. - How solar tax credits are being misrepresented and what the IRS has to say about it. - The truth behind inflated a...
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318. How to 2-3X Rental Income From Midterm Rentals with Jesse Vasquez

March 25, 2025 • 45 mins
In this episode of the Tax Smart REI Podcast, Thomas and Justin talk with midterm rental expert Jesse Vasquez, founder of AirVenture Academy, about how he accidentally stumbled into midterm rentals and scaled his business into a highly profitable portfolio. Jesse shares the exact strategies he uses to 2-3X rental income by securing long-term contracts with corporate clients, relocation companies, and healthcare providers, all with...
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317. Crush Break-Even: Pricing and Occupancy Hacks for your STR with Avery Carl

March 18, 2025 • 35 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan talk with short-term rental investor Avery Carl, founder of the Short Term Shop and author of Smarter Short-Term Rentals, about how she grew one cabin purchase into a portfolio of over 250 units. Avery shares the blueprint for choosing the right vacation markets, designing systems for self-management, and avoiding costly pitfalls in today’s higher-rate environment. Tun...
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316. Tiny Homes, Huge Returns: How Rob Abasolo Built a Winning STR Portfolio

March 11, 2025 • 43 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with short-term rental investor Rob Abasolo—the mind behind the “Robuilt” YouTube channel—to discuss how he transformed his copywriting background into a thriving short-term rental empire. Rob reveals how he maximizes ROI through unique stays, eye-catching design, and strategic tax planning. Tune in to learn: - Why tiny homes and unique spaces can command pr...
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