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
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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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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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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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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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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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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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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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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March 3, 2025 • 28 mins
In this episode, Thomas and Nathan Sosa take a deep dive into the potential 2025 tax changes that could reshape the landscape for real estate investors. They outline what may happen if the Tax Cuts and Jobs Act expires, how bonus depreciation could come back (or not), and what you need to do to prepare now so you’re not caught off-guard.
They discuss:
- Tax Brackets & QBI: How rates could shift in 2025—and why that matters for yo...
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February 24, 2025 • 27 mins
In this episode, Ryan and Thomas take a deep dive into depreciation, one of the most powerful tax-saving tools available to real estate investors. They break down how depreciation works, how to accelerate it, and strategies to minimize depreciation recapture when selling your properties.
They discuss:
- Depreciation 101 – What it is, how it works, and why it matters for investors.
- Cost Segregation & Bonus Depreciation – How to ...
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February 12, 2025 • 30 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with short-term rental investor Michael Chang to discuss how he went from Wall Street investment banker to building a 38-property short-term rental empire. Michael shares how he leveraged rental arbitrage, short-term rental tax strategies, and automation to achieve financial freedom.
Tune in to learn:
- How Michael transitioned from a high-pressure Wall Street...
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February 11, 2025 • 22 mins
In our first monthly Q&A episode, Ryan and Thomas answer the most pressing tax questions from listeners. They tackle a variety of hot-button topics, including when flipping property income is considered “active” (and why that matters if you have a W-2), how partial asset dispositions really work, and whether or not a cost segregation study has to be performed in the first year.
They discuss:
- Flips & W-2 Incomes – Why these pro...
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February 6, 2025 • 23 mins
In this episode, Ryan and Thomas pull back the curtain on LLCs, busting the biggest myths that trip up real estate investors—and revealing how to truly protect your rental portfolio.
They discuss:
- Asset Protection vs. Tax Savings—understanding what LLCs really do (and don’t do).
- The Right Structure—single-member, multi-member, or holding company?
- Pitfalls to Avoid—from the “due on sale” clause to S corp mix-ups.
- And more!...
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January 29, 2025 • 43 mins
In this episode of the TaxSmart REI Podcast, Thomas and Ryan sit down with Dave Meyer, Head of Real Estate Investing at BiggerPockets, to discuss the 2025 real estate market outlook and what investors need to know.
Tune in to learn:
- Where we are in the current real estate market cycle and what’s next for home prices and sales volume.
- How interest rates and affordability will impact investors in 2025.
- The state of commercial...
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January 25, 2025 • 50 mins
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with John Bianchi, founder of STR Search and an expert in short-term rental data and investment strategies.
With a 100% track record in helping investors identify and acquire over 200 profitable short-term rental properties, John shares his insider knowledge on leveraging Airbnb data to find winning deals.
Tune in to learn:
- How to use the “20% Rule” to eval...
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January 18, 2025 • 42 mins
In this episode of the Tax Smart REI Podcast, Thomas, Ryan, and Justin sit down with Austin Dean, a financial planner at Waystone Advisors specializing in real estate-focused financial planning.
With over 13 years of experience, Austin offers valuable insights into creating financial independence through strategic investments tailored to real estate investors.
Tune in to learn:
- Why real estate is a powerful tool for building w...
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January 12, 2025 • 23 mins
In this episode, Ryan and Alex break down the top overlooked deductions real estate investors often miss—and how to ensure you’re capturing them all.
This episode explores:
- Why closing costs and loan costs should be included in your depreciable basis.
- The most common insurance mistakes that leave money on the table.
- The importance of taking depreciation (and what happens if you don’t).
- And More!
If maximizing your tax sav...
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January 4, 2025 • 29 mins
In this episode, Thomas and Ryan break down the essentials of real estate professional status (REPS) and how to qualify this year.
This episode explores:
- What REPS is and why it’s one of the top strategies for high-income earners.
- The two key tests to qualify and how to navigate them.
- Activities that count toward REPS—and what doesn’t.
- How grouping elections simplify meeting material participation requirements.
- Using c...
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December 27, 2024 • 29 mins
In this episode, Thomas and Ryan walk you through the short-term rental loophole updates to keep an eye on this year.
This episode explores:
- The passive activity rules and why the short-term rental strategy is a game-changer.
- Material participation tests and the most popular ways to qualify.
- How to use cost segregation and bonus depreciation for massive savings.
- Common mistakes to avoid and tips to set your business up f...
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December 12, 2024 • 22 mins
In this episode of the Tax Smart REI podcast, Thomas and Ryan address pivotal updates as the year draws to a close.
They provide essential insights into the expected 2025 tax changes, the implications of the new administration, and the recent developments regarding the Corporate Transparency Act's enforcement status.
Here's what they discuss:
- The Expiration of the Tax Cuts and Jobs Act
- Corporate Transparency Act Updates
- T...
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