Tax Smart Real Estate Investors Podcast

By Hall CPABusiness

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Tax Smart Real Estate Investors Podcast episodes

April 21 374. How People Make $50K Tax-Free Renting Their Home (Augusta Rule)
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down the Augusta Rule, one of the most talked-about and misunderstood tax strategies in real estate.
In this episode, we cover:
- Where the Augusta Rule came from and how it ended up in the tax code
- Who actually qualifies (and who doesn’t)
- Why this strategy is often overhyped, especially for business owners
- Real examples of homeowners earning $10K–$50K tax-free during major events
- How events like the World Cup, Super Bowl, and Olympics can create big opportunities
- The most common mistakes that can disqualify the strategy
We also answer a listener's question about getting a rental property out of an S-corp and why that can become a tricky (and expensive) situation if you’re not careful.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle
Submit your question for Tom & Nathan: go.therealestatecpa.com/question
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.
32 min
April 16 MLRE: Carried Interest: What’s Really Behind the “Loophole” and Why It's Misunderstood
In this solo episode, Nate Sosa breaks down one of the most important — and most misunderstood — concepts in real estate syndication: carried interest.
From its surprising origins in 16th-century shipping voyages to its modern-day use in private equity and real estate deals, Nate walks through how carried interest actually works, why it exists, and how it’s taxed.
You’ll learn:
- How GP/LP structures and waterfall distributions work
- The difference between promote, profits interests, and equity
- Why carried interest is taxed at favorable rates
- The real risks GPs take (and why the upside exists)
- What Congress has tried (and failed) to change about it
- Common structuring mistakes that could trigger IRS issues
Whether you’re an active sponsor or passive investor, this episode will help you better understand deal economics and what to watch for when evaluating opportunities.
Request a free discovery meeting: go.therealestatecpa.com/mlre
Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide
Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber
Submit your questions to: go.therealestatecpa.com/question
The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.
20 min
April 14 373. Insurance Mistakes Real Estate Investors Are Making (And What They’re Costing You)
Most real estate investors spend a lot of time learning how to build wealth, but far fewer know how to protect it when disaster comes.
In this episode, Thomas and Nate sit down with Michael Fried, Vice President and Partner at Strategic Claim Consultants, to break down what real estate investors need to know about insurance claims, asset protection, and avoiding costly coverage mistakes.
Michael shares why insurance claims are so often underpaid, when investors should bring in a public adjuster, and how poor policy design can leave owners exposed after fires, water damage, storms, and other major losses.
Whether you own one rental or a large portfolio, this episode will help you think more strategically about protecting your properties.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle
Submit your question for Tom & Nathan: go.therealestatecpa.com/question
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.
39 min
April 09 MLRE: Why Multifamily Is Still Uninvestable (And Where Smart Money Is Going Instead) With Brian Burke
Brian Burke, CEO of Praxis Capital and author of The Hands-Off Investor, joins the show to break down the current state of real estate investing and why he believes multifamily is still too early to touch.
We discuss:
- Why the multifamily market looks like a “traffic collision” right now
- The biggest mistake investors make trying to time the bottom
- Why senior housing may be the most overlooked opportunity today
- The real impact of AI on real estate (and jobs)
- Why tax benefits should NEVER be your primary investment thesis
If you’re an LP or GP trying to navigate today’s uncertain market, this episode will help you think more strategically about timing, risk, and where the real opportunities are emerging next.
Request a free discovery meeting: go.therealestatecpa.com/mlre
Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber
Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/
Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide
Submit your questions to: go.therealestatecpa.com/question
The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.
39 min
April 08 372. How Top Investors Handle Tax Deadlines (Strategic Extensions Explained)
Tax extensions aren’t something to avoid. They’re something to understand and use strategically.
In this episode, Nate Sosa and guest co-host Justin Shore break down why filing an extension is a normal (and often smart) move, even for tax professionals. They explain how extensions give you more time to file accurately, reduce costly mistakes, and help you stay in control of your tax strategy.
You’ll also learn how to properly handle payments, avoid common penalties, and use extensions alongside quarterly estimates to stay compliant and efficient.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle
Submit your question for Tom & Nathan: go.therealestatecpa.com/question
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.
27 min
April 03 MLRE: Disguised Sales: How Refinances Can Trigger Unexpected Taxes in Syndications
In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa break down one of the most misunderstood areas of partnership tax law: disguised sales.
While many investors assume distributions and refinance proceeds are tax-free, the rules change when partnerships and contributed property are involved. Get it wrong, and what you thought was a tax-free event could actually be treated as a taxable sale.
You’ll learn:
- How partnership distributions actually work (and how they affect your basis)
- What a disguised sale is and why the IRS cares
- The 2-year rule that can trigger unexpected taxes
If you’re a syndicator, GP, or investor contributing property into deals, this episode is a must-listen to avoid costly tax mistakes.
Request a free discovery meeting: go.therealestatecpa.com/mlre
Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber
Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/
Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide
Submit your questions to: go.therealestatecpa.com/question
The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.
22 min
April 01 371. Why Your Tenants Leave (And How to Fix It Fast) with Ryan Barone
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa sit down with Ryan Barone, co-founder and CEO of RentRedi, to break down how real estate investors can simplify property management, reduce tenant turnover, and increase ROI using automation and data.
You’ll learn practical strategies to improve tenant retention, including why speed of response (not resolution) is one of the biggest drivers of long-term tenants, how simple rent reminders can increase on-time payments by 27%, and why offering credit reporting can boost payment consistency.
The conversation also dives into automation tools like auto-pay (with 99% on-time payments), maintenance coordination, AI-powered bookkeeping, and real-time portfolio tracking.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Register for our FREE Tax Mistakes Webinar: go.therealestatecpa.com/3PpELKu
Submit your question for Tom & Nathan: go.therealestatecpa.com/question
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.
40 min
March 27 MLRE: How He Built a $1B Multifamily Portfolio (Without Third-Party Managers) with Rob Beardsley
In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa sit down with Rob Beardsley, founder and CEO of LSCRE, to break down what it really takes to scale a vertically integrated multifamily business in today’s market.
Rob shares how his firm grew to nearly $1 billion in Texas multifamily assets, why vertical integration gives operators more control, and where many investors misunderstand underwriting. He also explains why AI may improve operational efficiency more than underwriting itself, how strong investor relationships are built over time, and why tax strategy remains one of real estate’s biggest advantages.
The conversation also covers 1031 exchange structuring, current multifamily market conditions, and what Rob is seeing as the best opportunities moving forward.
Request a free discovery meeting: go.therealestatecpa.com/mlre
Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber
Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/
Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide
Submit your questions to: go.therealestatecpa.com/question
The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.
41 min
March 24 370. Two Major Housing Changes Investors Need to Know: Senate Housing Bill + FinCEN Reporting
Two major housing developments just hit real estate investors in a short window, and both could have a big impact on how you buy, hold, and scale residential real estate.
In this episode of the TaxSmart REI Podcast, Thomas Castelli and Nate Sosa break down the Senate’s 21st Century Road to Housing Act and FinCEN’s new residential real estate reporting rule that went live on March 1. They cover what the proposed housing bill could mean for investors with large single-family portfolios, the key exceptions built into the legislation, and how forced exit rules could create major tax planning considerations.
Update: FinCEN's new reporting rule has been paused.
To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6
Register for our FREE Tax Mistakes Webinar: https://go.therealestatecpa.com/3PpELKu
Submit your question for Tom & Nathan: go.therealestatecpa.com/question
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.
35 min
March 20 MLRE: Flying Private: What Syndicators Should Know About Deducting a Jet
In this episode, Nate and Tom break down the truth behind private jet tax write-offs: what works, what doesn’t, and where investors get into trouble.
They break down how bonus depreciation can create significant tax savings, why most jet structures default to passive losses, and how rules like material participation, business use, and grouping elections can make or break your strategy. Plus, they walk through real tax court cases where investors lost and what you can learn from them.
Request a free discovery meeting: go.therealestatecpa.com/mlre
Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber
Get the Aircraft Acquisitions White Paper: www.therealestatecpa.com/aircraft-white-paper/
Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide
Submit your questions to: go.therealestatecpa.com/question
The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.
26 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.