Podcast
Tax Smart Real Estate Investors Podcast
Hosted by Hall CPA · EN
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.
Our episodes generally run 30-60 minutes of no-nonsense, hard-hitting information. We know your time is valuable so our goal is to save you thousands of dollars per episode.
Hall CPA, PLLC is a CPA firm that exclusively serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch.
Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information.
Enjoy!
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
208episodes
Episodes
Newest firstAll episodes
369. 5 Non-Negotiables for Airbnbs in 2026 with Taylor Jones
Mar 1700:46:24Summary readyIn 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.
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MLRE: K-1 Season Explained: Depreciation, Capital Accounts, and Passive Losses
Mar 1200:25:41Summary readyK-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.
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368. Does Buy, Borrow, Die Still Work? Breaking Down Robuilt’s Strategy
Mar 1100:37:39Summary readyIn 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.
Summary
MLRE: How to Survive the 2026 Real Estate Cycle: AI & Capital Raising Strategies
Mar 500:46:11Summary readyIn 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.
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367. The Short-Term Rental ‘Loophole’ That Didn’t Work for This $25M Business
Mar 300:27:18Summary readyIn 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.
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MLRE: The Syndication Mistakes I'd Never Make Again (An Investor Deep Dive)
Feb 2600:26:46Summary readyIn 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.
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366. AI vs. The IRS: What Every Investor Must Learn from This Tax Court Case
Feb 2400:26:45Summary readyIn 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.
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365. Can You Really Write Off a Private Jet? What Actually Works with Preston Holland
Feb 1700:47:05Summary readyIn 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.
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364. The Tax Questions High-Income Real Estate Investors Are Asking in 2026
Feb 900:25:06Summary readyIn 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.
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363. Tax Filing Mistakes That Cost Real Estate Investors Thousands
Feb 300:33:54Summary readyIn 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.
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