
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!
Latest episodes

Dec 13, 2024 • 22min
304. 2025 Tax Changes & The Corporate Transparency Act Update
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
- Tips on Staying Proactive with Voluntary Compliance Measures
- Advice for Real Estate Investors to Prepare for Year-End
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
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.

Dec 6, 2024 • 41min
303. From Rookie to Mogul: How to Build Rental Real Estate Riches with Travis & Regan Perry
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with Travis and Regan Perry, real estate investors who have crafted a flourishing portfolio of short-term rental properties. With roots in Iowa, the Perrys share their journey from purchasing their first home to managing multiple properties across several states.
Tune in to learn:
- Steps to start investing in short-term rentals and build a substantial property portfolio.
- How to leverage local events and tourism to maximize rental income.
- The importance of tax strategies, including cost segregation, to enhance cash flow.
- Practical tips for managing properties remotely and building a reliable team.
Whether you’re a budding entrepreneur or an experienced investor, this episode is brimming with invaluable insights and inspiring stories to help you expand your real estate ventures.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Connect with Travis & Regan:
https://shorttermrentaledge.com/
https://perrydisevacationrentals.com/
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
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.

Nov 29, 2024 • 35min
302. Short-Term Rental Financing: Taxes, Loans, and Winning Strategies with Stacey Dowling
In this episode of the Tax Smart REI Podcast, Thomas & Ryan sit down with Stacey Dowling, a seasoned mortgage lender specializing in short-term rental financing. Stacey brings over 30 years of experience to the table, offering actionable insights into obtaining loans for short-term rentals.
Tune in to learn:
- How to qualify for a short-term rental loan.
- The impact of tax returns, depreciation, and cost segregation on lending decisions.
- Strategies to navigate regulations and mitigate challenges from neighbors or local laws.
- Creative approaches like midterm rentals to adapt to changing market dynamics.
Whether you’re a seasoned investor or just getting started, this episode is packed with expert advice and real-world examples to help you achieve your real estate goals.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Connect with Stacey Dowling:
Email: sdowling@dg-lending.com
Visit PURE at: www.rentpure.com
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
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.

Nov 24, 2024 • 45min
301. Why the Wealthy Invest differently: Timing, Trends, and Tax Benefits with Ben Fraser
In this episode, Thomas and Ryan are joined by Ben Fraser, Chief Investment Officer of Aspen Funds and host of the Invest Like a Billionaire podcast, to explore strategies of the ultra-wealthy and how they invest differently.
They cover:
- The difference between ultra-high-net-worth investors and retail investors
- Why private markets, including real estate and private equity, are the cornerstone of billionaire investment strategies
- The trade-offs between active and passive real estate investing
- Key insights on evaluating sponsors and deals to avoid common pitfalls
- Emerging trends in the alternative investment space
- And much more!
If you’re curious about how the wealthiest individuals protect and grow their capital—and how you can apply those strategies—this episode is full of actionable insights.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Visit PURE at: www.rentpure.com
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
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.

Nov 17, 2024 • 36min
300. The 14-Day Rule & Personal Use Days: Avoiding Common Pitfalls for STR Owners
In this episode of the Tax Smart REI podcast, Thomas and Ryan explore the critical nuances of personal use days for short-term rental properties, a topic that generates frequent questions from their community of real estate investors and tax-savvy listeners.
They break down the 14-day rule, share actionable strategies to avoid common pitfalls, and provide clarity on how personal use impacts your tax benefits—especially for those leveraging the short-term rental loophole.
Here’s what they discuss:
- The 14-day rule and how it applies to short-term rental properties
- What counts as personal use and how the IRS defines it
- Travel days, family stays, and the gray areas of personal use
- Best practices for keeping credible time logs & avoiding audit risks
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Visit PURE at: rentpure.com
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
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.

Nov 10, 2024 • 31min
299. Corporate Transparency Act Checklist: Avoid Costly Mistakes with FinCEN Filing Agents
Heather Lucor, CEO of FinCEN Filing Agents, shares crucial insights about the Corporate Transparency Act and its looming 2024 implications for real estate investors and small businesses. She explains key reporting requirements and the dire consequences of non-compliance. The conversation highlights strategies to streamline the filing process, the importance of timely updates, and privacy concerns regarding sensitive information. Lucor also addresses the alarming low filing rates and offers solutions for those feeling overwhelmed by the upcoming deadlines.

Nov 2, 2024 • 41min
298. From Schedule E to Cost Segregation: Tackling Taxes with an Expert Q&A
Discover essential tax strategies for short-term rental owners, including the differences between Schedule C and Schedule E. Learn about maximizing deductions on travel, meals, and home offices. Explore capital gains strategies and how to minimize tax liabilities using Qualified Opportunity Zones. Delve into the long-term tax benefits of losses offsetting future profits and the importance of accurate record-keeping. Plus, get tips on navigating potential IRS audits and year-end tax planning!

6 snips
Oct 29, 2024 • 56min
297. Drilling Into Profits: A Case Study on Oil & Gas Working Interests with Troy Eckard
Troy Eckard, an oil and gas expert with over 40 years of experience, shares his invaluable insights on working interests. He discusses a detailed case study that highlights cost structures and common pitfalls in investing. Troy emphasizes the importance of modern drilling technologies in reducing risks and maximizing returns. He also explores the long-term investment potential of oil and gas, showcasing substantial tax benefits that can diversify portfolios. His practical strategies and due diligence tips are essential for anyone considering this sector.

Oct 22, 2024 • 34min
296. Top Year-End Tax Strategies: Maximize Deductions Before December 31st
Explore savvy year-end tax strategies specifically designed for real estate investors. Learn about the benefits of purchasing short-term rentals and how to leverage the short-term rental loophole. Discover ways to maximize vehicle deductions, especially for heavier vehicles. Gain insights on qualifying for real estate professional status and the importance of cost segregation. Plus, find out how to effectively implement tax loss harvesting, prepay expenses, and ensure proper documentation for contractors to boost your deductions before the year closes.

Oct 15, 2024 • 56min
295. The Future of Housing: How Interest Rates and Labor Shape Real Estate with Logan Mohtashami
Logan Mohtashami, a renowned housing analyst, dives deep into the dynamics of the current real estate market. He discusses how mortgage rates are influenced by labor data and Federal Reserve policies. The podcast highlights the impact of supply and demand on pricing and potential interest rate cuts that could reshape market affordability. Logan also shares insights on demographic shifts affecting housing demand and provides strategies for investors navigating today’s challenging market conditions.