Tax Smart Real Estate Investors Podcast

By Hall CPABusiness

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per episode

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Tax Smart Real Estate Investors Podcast episodes

April 16, 2025 322. Real Estate Investor Case Studies: How One Client Saved $285K in One Year
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 segregation.
- Why timing matters when using the short-term rental loophole—and how to get it right.
- What happens when a CPA mistakenly opts you out of bonus depreciation.
- How a non-REPS investor reduced their taxes by $40K annually—without changing jobs.
- Real examples of costly filing mistakes, disqualified STRs, and even unintentional fraud.
If you're serious about using real estate to build wealth and reduce taxes, while avoiding irreversible errors, this is an episode you can’t afford to skip.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Subscribe to REI Daily & Enter to Win a FREE Strategy Call:
go.therealestatecpa.com/41JuQBX
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.
37 min
April 11, 2025 321. Does Travel Time Count Toward Material Participation?
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 Improvement Records
- The 14-Day Rule Explained
Remember to submit your questions at [email protected] or the Tax Smart Investors Facebook group.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Subscribe to REI Daily & Enter to Win a FREE Strategy Call:
go.therealestatecpa.com/41JuQBX
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.
22 min
April 09, 2025 320. How Creative Financing Helps RE Investors Succeed in Every Market Cycle w/ Chris Prefontaine
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 about:
- Why 2008 changed the way Chris does business forever
- How creative financing works in any market cycle
- The power of principal-only payments
- Real-world examples of building long-term wealth without traditional loans
Whether you're looking to grow your long-term rental portfolio, invest in short-term rentals, or just want to stop competing in the bank-financed rat race, this episode is packed with insights and strategy.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Subscribe to REI Daily & Enter to Win a FREE Strategy Call:
go.therealestatecpa.com/41JuQBX
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
Free Resources from Chris:
Get his best-selling book FREE at wickedsmartbooks.com/TSI
Watch his free creative financing workshop: smartrealestatecoach.com/mastersclass
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.
31 min
April 02, 2025 319. 3 Tax Scams to Watch Out for in 2025 (And 2 Risky Strategies to Avoid)
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 art donation deductions and the risks they carry.
- Two high-risk strategies—discounted IRA rollovers and deferred sales trusts—that aren’t scams, but require extreme caution.
If you're serious about protecting your wealth and staying out of IRS crosshairs, this is one episode you won’t want to miss.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Subscribe to REI Daily & Enter to Win a FREE Strategy Call:
go.therealestatecpa.com/41JuQBX
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
Connect with Jesse:
www.youtube.com/channel/UC2x-yFc6Dbtzul2eN_Iskgw
www.airventureacademy.com/
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.
28 min
March 26, 2025 318. How to 2-3X Rental Income From Midterm Rentals with Jesse Vasquez
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 without the constant turnover and management headaches of short-term rentals.
Tune in to learn:
- Why midterm rentals are the most overlooked and under-regulated strategy in today’s market.
- How Jesse consistently lands corporate housing contracts that pay 2-3X traditional rent.
- The step-by-step method for connecting with hospitals, construction firms, and relocation companies.
- Why midterm rentals offer fewer risks (and more reliable tenants) than long-term leases.
- How Jesse structures his rentals to maximize cash flow and leverage tax-saving strategies.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Subscribe to REI Daily & Enter to Win a FREE Strategy Call:
https://go.therealestatecpa.com/41JuQBX
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
Connect with Jesse:
https://www.youtube.com/channel/UC2x-yFc6Dbtzul2eN_Iskgw
https://www.airventureacademy.com/
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.
46 min
March 19, 2025 317. Crush Break-Even: Pricing and Occupancy Hacks for your STR with Avery Carl
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.
Tune in to learn:
- Why buying where you’ve actually vacationed can give you a guest-focused edge.
- How strategic pricing and technology keep your calendar booked—even off-season.
- The real scoop on “mega-theming” and the simple design approach that still earns five-star reviews.
- Tips for building a reliable local team when you’re investing from afar.
- How Avery leverages the short-term rental tax strategy to keep more cash in her pocket.
This episode will help you spot the right deals and scale sustainably.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Are You Ready for the 2025 Tax Changes?
Click HERE to Access the FREE Tracker:
go.therealestatecpa.com/4gDayj7
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
Connect with Avery:
The Short Term Shop: theshorttermshop.com
Avery Carl on Instagram: @theaverycarl and @theshorttermshop
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.
36 min
March 12, 2025 316. Tiny Homes, Huge Returns: How Rob Abasolo Built a Winning STR Portfolio
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 premium nightly rates.
- How reinvesting in a property’s outdoor amenities can boost revenue—and profit—dramatically.
- Practical tips on professional photography, design, and marketing that set listings apart.
- Key strategies for leveraging the short-term rental loophole and bonus depreciation.
- Rob’s blueprint for scaling a short-term rental portfolio, including his biggest upcoming deal.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Are You Ready for the 2025 Tax Changes?
Click HERE to Access the FREE Tracker:
go.therealestatecpa.com/4gDayj7
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
Connect with Rob:
https://www.instagram.com/robuilt/
https://www.hostcamp.com/
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.
44 min
March 04, 2025 315. The Future of Bonus Depreciation and SALT: 2025 Tax Updates with Nathan Sosa, CPA, MST
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 your business income.
- 100% Bonus Depreciation: Whether it might return, why it’s a hot-button issue, and how to plan for different outcomes.
- SALT Deduction & Carried Interest: Why these provisions make headlines, what reforms might occur, and how changes could affect you.
- Legislative Timing: The critical milestones for budget reconciliation and what to expect from Congress in 2025.
- Survival Strategies: Extending your returns, tracking key bills, and taking advantage of planning opportunities to minimize taxes.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Are You Ready for the 2025 Tax Changes?
Click HERE to Access the FREE Tracker:
go.therealestatecpa.com/4gDayj7
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.
29 min
February 25, 2025 314. Depreciation 101: How to Use It the Right Way to Save Thousands in Taxes
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 front-load tax savings and boost cash flow.
- Depreciation Recapture – The “dark side” of depreciation and how to avoid unnecessary tax hits.
- Strategic Planning – When a cost segregation study makes sense and how to use depreciation to offset W-2 or passive income.
- The Lazy 1031 Exchange – A little-known strategy to defer taxes without doing a full 1031 exchange.
- And more!
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Are You Ready for the 2025 Tax Changes?
Click HERE to Access the FREE Tracker:
go.therealestatecpa.com/4gDayj7
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.
28 min
February 13, 2025 312. From Wall Street to Short-Term Rentals: How to Build a 38-Property Empire with Michael Chang
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 career to full-time real estate investor.
- The basics of rental arbitrage and why it’s an ideal starting point for new investors.
- How Michael scaled his short-term rental business to 38 properties while optimizing for tax efficiency.
- The key technology and AI tools that help him manage his portfolio remotely.
- Strategies for reducing taxes and maximizing cash flow as a short-term rental investor.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Are You Ready for the 2025 Tax Changes?
Click HERE to Access the FREE Tracker:
go.therealestatecpa.com/4gDayj7
Join the Tax Smart Insiders Community:
go.therealestatecpa.com/3Xx1Cpd
Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli
Connect with Michael: https://www.strlikethebest.com/
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.
31 min

About Tax Smart Real Estate Investors Podcast

From the publisher's feed

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.