Tax Smart Real Estate Investors Podcast

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.

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.

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.

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.

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.

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.

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.

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. 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.

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.

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa sit down with Taylor Jones of STR Search to break down the top five non-negotiables for profitable short-term rentals in 2026. What You’ll Learn: - Taylor’s 5 biggest STR non-negotiables for 2026 - Why revenue management can dramatically increase profitability - How one-bedroom couples retreats can outperform larger homes 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 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.

K-1 season can be confusing for real estate investors, especially when depreciation, passive losses, and capital accounts start showing up on your tax documents. In this episode, Nate and Tom break down the fundamentals of depreciation in real estate partnerships and how it impacts both general partners (GPs) and limited partners (LPs). They walk through how cost segregation studies accelerate deductions, why passive losses matter for investors, and how depreciation is allocated inside syndications. They also explain why capital accounts and outside basis determine whether investors can actually use the losses shown on their K-1 and why partnership operating agreements need to align with IRS rules like Section 704(b). Whether you're a syndicator structuring deals or an investor trying to understand your K-1, this episode provides a clear overview of how depreciation works inside real estate partnerships. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber 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.

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa react to Robuilt’s video on the buy, borrow, die strategy and the short-term rental loophole. They break down how wealthy investors use leverage to build tax-efficient wealth, why real estate can be the easiest entry point into this strategy, and how short-term rentals may help W-2 earners unlock major tax savings. Thomas and Nate also cover key concepts like cash-out refinances, step-up in basis, bonus depreciation, cost segregation, material participation, and the limitations investors need to understand before putting this strategy into action. If you’ve ever wondered how buy, borrow, die actually works and how the short-term rental loophole fits into the picture, this episode breaks it all down. 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 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.

In this episode of the Major League Real Estate Podcast, we sit down with Victor Menasce, tech executive turned real estate developer, host of the Real Estate Espresso Podcast, and author of Magnetic Capital, to break down what’s really happening in today’s market. From leaving Silicon Valley in 2009 to building multifamily projects in uncertain cycles, Victor shares how his background in tech shaped the way he approaches development, capital raising, and long-term wealth building. But that’s not all. Victor also dives into: - Why the real estate market is “splitting in two” and who gets squeezed - The biggest mistake syndicators make when raising capital - What lenders are doing behind the scenes (including term sheet bait-and-switch tactics) - Why real estate should be treated like product design, not a commodity For GPs raising capital, LPs evaluating deals, or operators trying to adapt to a rapidly changing market, this episode delivers strategic insights on surviving — and thriving — in the 2026 real estate cycle. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question Connect with Victor: ystreetcapital.com/ 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.

In this episode, we break down a real-life tax scenario from a $25M dealership owner who’s trying to reduce a massive annual tax bill. Here’s the situation: - A successful dealership generating $25 million in revenue - An equipment rental business purchasing millions in assets each year - Ownership of the commercial building they operate out of - Two short-term rentals purchased to “unlock” tax savings On paper, it sounds like they should be crushing their tax strategy. In reality? They’re leaving hundreds of thousands of dollars on the table. As always, this is a modified real-world case study designed to help you learn from situations we see every day. 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 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.

In this episode of the Major League Real Estate Podcast, Thomas Castelli shares the full story of his journey, from attending local RIAs and investing as an LP, to joining the GP team on an 82-unit apartment complex, navigating hurricane due diligence, raising capital under pressure, and exiting during the chaos of COVID in 2020. But that’s not all. Tom also opens up about: - The hardest lesson he learned about capital raising - Why most new GPs underestimate the importance of investor relationships - What changed in the syndication world since 2017 - The risks LPs don’t think about (until it’s too late) - How a failed ATM investment reshaped his investing philosophy -,Why experience matters more than ever in today’s market For GPs raising money, LPs evaluating risk, or investors entering the syndication space, this episode shares practical, experience-backed insights. Request a free discovery meeting: go.therealestatecpa.com/mlre Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: contact@therealestatecpa.com 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.

In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa dive into a recent Tax Court case that’s turning heads in the tax community. They break down how a taxpayer’s DIY tax returns spiraled into a full-blown IRS audit, with the IRS reconstructing income through bank deposits, uncovering significant underreported receipts, and disallowing deductions when documentation couldn’t be produced, including depreciation tied to rental properties. But the wildest part? The defense relied on AI-generated, hallucinated Tax Court case citations that didn’t actually exist. It's an expensive lesson in why AI isn’t ready to be your CPA and why “close enough” recordkeeping can get you crushed when the IRS starts asking questions. If you’re investing in real estate, running a business, or leaning on AI for tax answers, this episode is a must-listen on why bookkeeping, documentation, and competent representation matter more than ever. 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. 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 Castelli and Nathan Sosa sit down with Preston Holland, President and Founder of Prestige Aircraft Finance, to unpack what it really takes to buy back your time through private aviation. The conversation tackles the big tax questions: Can you really write off 100% of a private jet using bonus depreciation? What qualifies as legitimate business use? And how closely is the IRS scrutinizing aircraft deductions? If you’ve seen the “write off a private jet” hype online and want the truth about what works and what doesn’t, this episode is required listening. 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. 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 Castelli and Nathan Sosa answer the most pressing questions from real estate investors and high-income earners in 2026. If you're investing in real estate, you may very well have these same questions. 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. 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 Castelli and Nathan Sosa break down the most common - and most expensive - real estate tax filing mistakes investors make, and why many of them don’t show up until tax season, when it’s already too late to fix them. This episode is for high-income W-2 earners, business owners, and real estate investors who want to ensure they file correctly, protect their tax strategy, and avoid preventable leaks. If you want to understand the filing side of real estate taxes and avoid the errors that cost investors the most, this episode is required listening. 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. 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 Castelli breaks down how high-income earners can legally build tax-advantaged, tax-free income through real estate - even without REPS or short-term rentals. You’ll get a practical crash course on how the U.S. tax system actually works, why real estate is treated so favorably by the IRS, and how savvy investors use depreciation, refinancing, and smart exit strategies to increase cash flow while lowering their effective tax rate. This episode is for high-income W-2 earners, business owners, and real estate investors who want to zoom out, understand the bigger picture, and stop chasing one-off tax hacks. If you’re looking to build long-term, tax-efficient wealth through real estate -- this is your roadmap. 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. 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.