Tax Smart Real Estate Investors Podcast

By Hall CPABusiness

Favorites
225
Followers
Typical duration
35 min
per episode

Based on Podcast App listening data

Tax Smart Real Estate Investors Podcast episodes

June 18, 2025 332. Can AI Replace Your Tax Advisor?
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 rules
- A new listener question ChatGPT got both right and wrong
- Why nuanced tax strategy still requires a real human advisor
- How IRS regulations trip up AI systems
- Real examples where relying on ChatGPT could lead to audit risk
Plus, Thomas shares a fresh, real-world test he ran through ChatGPT just hours after recording and breaks down exactly where it gave conflicting answers. If you’re using AI to guide your tax decisions, this is an episode you don’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
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.
32 min
June 11, 2025 331. The Overlooked Tax Move that Could Save You Tens of Thousands
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 to support PAD calculations
- Real-life case studies, including one client who saved over $2 million
- When PAD losses are passive vs. non-passive
- Why traditional CPAs rarely take advantage of this strategy
- How to spot missed PAD opportunities in your depreciation schedule
Plus, Thomas and Ryan explain which types of renovations typically qualify and how to make sure your CPA isn’t leaving valuable deductions on the table.
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
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.
19 min
June 04, 2025 330. What Your CPA Isn't Telling You (And It's Costing You Thousands) with Justin Shore
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
- The overlooked grouping strategy that saved one client $150K+ in a single year
- What really happens when CPAs misuse the Augusta Rule (and how to do it right)
- How a "medical tax specialist" cost a client over $100K in phantom tax savings—and exposed them to penalties
If you’re working with a CPA who doesn’t specialize in real estate, this episode might just save you from years of missed opportunities or worse, an audit.
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
Wealth & Wisdom Event:
https://www.dklawmd.com/events-calendar/wealth-and-wisdom-2025
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.
43 min
May 28, 2025 329. What Really Happens During an IRS Audit (and How to Win One) with Troy Silfies, CPA
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—with documentation and strategy
- Why being “audit-ready” matters more than ever in the post-TCJA world
- What to do (and not do) the moment you receive that dreaded IRS letter
If you want to understand what an audit really looks like and how to protect yourself before one ever happens, this episode is a must-listen.
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.
44 min
May 21, 2025 328. Inside the “One Big, Beautiful Bill” & How To Prepare for it with Nathan Sosa, CPA, MST
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 the bill
- Changes to Qualified Opportunity Zones and what they mean for investors
- Section 179 expensing increases for short-term rentals and asset-heavy businesses
- QBI deduction bumps and simplified rules for service-based businesses
- Full expensing for industrial facilities (and how it could spark a manufacturing boom)
- “No tax on tips, overtime, or Social Security” — what made it in and what didn’t
Plus, we cover what provisions are being made permanent, what’s being rolled back, and why now is the time to align with a tax advisor who knows how to play offense with the tax code.
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.
38 min
May 14, 2025 327. 2025 Tax Bill Preview: Bonus Depreciation, SALT Cap Changes, and Investor Q&A
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 Professional Status)
- Using the STR loophole for boutique hotels
- Depreciating furniture in furnished rentals
- Grouping LP losses with active rentals
- Why tax planning still matters, even if you don’t qualify for REPS or STR
Plus, we tackle common mistakes CPAs make and discuss whether setting up a property management company for your own rentals actually makes sense.
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.
31 min
May 08, 2025 326. What to Do Now that Tax Day is Over + Answering Your Pressing Questions
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 Tax Smart Facebook group.
Topics include:
- Real estate investment takeaways from interviews with Robuilt, Avery Carl, Henry Washington, and more
- What to do (and not do) after 4/15 for tax savings
- The latest on the 2025 tax bill and bonus depreciation
- How step-up in basis affects depreciation
- Using Form 3115 to catch up on missed depreciation
- REPS Log and time tracking for short-term rental investors
- Why LP losses don’t offset W-2 income—and what to do about it
- The lazy 1031 exchange strategy for exiting syndications
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.
25 min
May 07, 2025 325. Why Now Might Be Multifamily’s Biggest Opportunity Yet with Michael Blank
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 driving investor hesitation—and how to overcome it.
- How tariffs, inflation, and interest rates are reshaping deal underwriting.
- Why syndication outpaces the BRRRR strategy for wealth and time freedom.
If you’ve been thinking about making the leap from single-family to multifamily—or are just curious what’s working in today’s unpredictable environment—this episode is packed with insights from one of the top minds in the business.
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
Training from Michael:
thefreedompodcast.com/thomas
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.
38 min
April 30, 2025 324. Which Boring Strategy Still Wins in 2025? With Henry Washington
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—without overreacting to headlines.
- Why he believes helping sellers matters more than squeezing every dollar.
- How to find pain points in the market—and actually solve them.
- What newer investors get wrong by chasing the “next big thing.”
If you’re looking for a grounded, proven approach to real estate investing, even in times of rising rates and economic uncertainty, this episode will give you clarity and confidence.
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
Connect with Henry on Instagram: @thehenrywashington
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.
30 min
April 23, 2025 323. 2025 Market Volatility: What Real Estate Investors Need to Know with Connor Low
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 investors can make smart, intentional decisions during periods of volatility.
Tune in to learn:
- Why today’s stock market volatility is driven more by emotion than economic data.
- How real estate investors can take advantage of discounted equities without abandoning their REI strategy.
- The right (and wrong) times to rebalance, lump-sum invest, or just sit tight.
- Why Connor isn’t bullish on infinite banking—and what he recommends instead.
- How his goal-based planning model helps investors make smarter decisions with both real estate and the stock market.
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
Connect with Conner: iarannwealth.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.
39 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.