Tax Smart Real Estate Investors Podcast

In this episode of the Tax Smart REI Podcast, Thomas Castelli sits down with Hall CPA Advisory Manager Justin Shore to break down why bookkeeping isn’t just busy work, it’s the foundation of audit defense and financial success as a real estate investor.

Tune in to learn:

- Why sloppy bookkeeping can raise red flags and trigger IRS scrutiny

- The key differences between Schedule E and Schedule C—and why they matter for your rentals

- How proper categorization of expenses (like cleaning vs. repairs) can make or break your audit defense

- Why bank statements aren’t enough, and the documentation you must keep to substantiate deductions

- The penalties and costs of poor records and how to avoid them

- The line between bookkeepers and tax preparers, and what responsibilities truly fall on you

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

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. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.

In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with financial planner and short-term rental investor Zack Mattos to unpack how he went from a 20-year career focused solely on traditional retirement accounts to leveraging real estate to nearly eliminate his tax bill, including a staggering $943K in depreciation from one luxury rental property.

Tune in to learn:

- How he turned his Austin dream home into a high-income rental and tax-saving machine

- The cost segregation strategy that generated nearly $1M in depreciation in a single year

- Why he paused retirement account contributions to focus on real estate acquisitions

- How REP status transformed his tax outcomes and influenced client recommendations

- The S-corp move and family payroll strategy that added tens of thousands in annual savings

- His plan to build a portfolio of luxury rentals in one high-demand neighborhood for scale and ease of management

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

Subscribe to REI Daily & Enter to Win a FREE Strategy Call:

go.therealestatecpa.com/41JuQBX

Connect with Zack: https://www.zackmattos.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. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor

In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with entrepreneur and investor John Paul Houston to unpack his journey from running a backyard chicken operation to building a $3.5M private lending portfolio and a 100+ door real estate empire — all while dramatically reducing his tax bill by qualifying as a Real Estate Professional.

Tune in to learn:

- How John went from semi-retirement to scaling multiple income-producing businesses

- Why he shifted from passive lending to active investing for greater returns and tax benefits

- The REP strategies and depreciation plays that helped him save big on taxes

- How he structures equity incentives to retain top talent and transfer ownership

- Why West Virginia is his secret weapon for finding 12-cap multifamily deals with minimal red tape

- The role private lending plays in his long-term diversification and estate planning

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

www.taxandlegalsummit.com/registration

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.

In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with entrepreneur and investor Marty Geier to unpack how he reduced his taxable income from $1.4 million to just $40K using a blend of business building, short-term rentals, and advanced tax strategy.

Tune in to learn:

- How Marty uses the 500-hour rule to make short-term rental losses non-passive and deductible

- Why he starts a new business each year and how it helps offset active income

- The exact way he structures his real estate and businesses to maximize Section 179 and bonus depreciation

- How he tracks performance across 10+ ventures to know when to scale, pivot, or exit

- What most investors underestimate about the real-time commitment of running rentals

To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6

Get your FREE ticket to the 2025 Tax, Legal, and Wealth Summit:

https://www.taxandlegalsummit.com/registration

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.

Before you commit to a whole life insurance policy, you need to understand what it really is and what it isn’t. This week on the Tax Smart REI Podcast, we sit down with financial planner Alex Savage, CPA and CFP, to break down the infinite banking concept and whether it truly makes sense for real estate investors and high-income earners.

You'll learn:

- What whole life insurance and infinite banking actually are (beyond the sales pitch)

- Why policy loans aren't “free money” and how they really work

- What hidden costs, commissions, and risks most people overlook

- How this strategy compares to simply investing in real estate or ETFs

- Who this approach might actually work for and who should avoid it

If you've been pitched on infinite banking or are wondering whether to use life insurance as an investment vehicle, this episode gives you the full picture so you can make an informed decision.

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.

Before you hire just any tax pro, you need to understand what a real estate-focused advisor can actually do for you. This week on the Tax Smart REI Podcast, we sit down with investor and developer Lauren Kraus to hear how working with a specialist helped her uncover over $280K in missed tax savings—and dramatically shift her investing strategy.

You'll learn:

- Why her CPA dismissed cost segregation (and why that was a $280K mistake)

- How real estate professional status (REPS) changed their entire tax position

- What Form 3115 did to retroactively unlock depreciation

- How tax strategy helped get her husband fully on board with real estate investing

If you’re self-managing, scaling across markets, or wondering what your current CPA might be missing, this episode will open your eyes to what’s possible with the right strategy in place.

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.

In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down everything real estate investors and business owners need to know about the now-official “Big Beautiful Bill”, the sweeping tax package that just became law.

Key topics covered:

- 100% bonus depreciation is back and permanent: who qualifies and when it starts

- QBI updates: simplified rules, new thresholds, and small business wins

- SALT cap expansion (finally!) and what the five-year phase-in means for planning

- Section 179 expensing: higher limits and how it benefits STRs and commercial assets

- Qualified Opportunity Zones get renewed: what’s changing in 2027

- And more!

Plus, we highlight the planning window left in 2025, how to take action before year-end, and why this bill sets the stage for strategic investing and long-term tax savings.

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.

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 agreements, and operating agreements actually do

- Why you shouldn’t rely on capital raisers (and how to avoid SEC trouble)

Whether you're raising $200K or $2M+, this episode is packed with real-world advice to help you syndicate legally and confidently.

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

Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/

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.

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 short-term rentals can’t be included in a Dash-9 grouping election

- What counts as "placed in service" when a tenant isn’t paying rent

- How to take 100% bonus depreciation in 2025 for a 2022 STR purchase

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

Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/

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.

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 still a moving target

- Expanded QSBS exclusion and its impact on startup investors

- The Senate’s fix to Excess Business Loss (EBL) carryovers

- Why QBI stays at 20% and who gets left out of the benefit

Plus, Thomas and Ryan take questions from the Tax Smart community on short-term rentals without guest stays, the risks of self-preparing complex tax returns, and what happens when you sell a property at a loss.

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

Connect with Eckard Enterprises: https://eckardenterprises.com/taxsmartrei/

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.