Tax Smart Real Estate Investors Podcast

Hall CPA

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

  1. 8 hr ago

    390. The Tax Elections You Might Already Be Stuck With (And How to Save Up to $40,000)

    Some tax decisions are easy to change. Others can lock you into a strategy you may not be able to undo. In this episode of the Tax Smart REI Podcast, Nate Sosa sits down with Hall CPA Senior Advisory Manager Justin Shore to break down tax elections that real estate investors need to understand before filing their returns. They discuss how elections can be buried inside a tax return or even be made simply by failing to file a form or check the right box. Nate and Justin cover real estate professional status and grouping elections, opting out of bonus depreciation, installment sales, 1031 exchanges, Section 754 elections, and grouping businesses under the passive activity rules. They also explain why timing matters, when an election can restrict future tax-planning opportunities, and why investors should understand the decisions being made on their returns rather than simply signing and filing. If you're buying or selling real estate, claiming depreciation, qualifying as a real estate professional, or making other major tax moves, this episode highlights the questions you should be asking your tax professional before the return is filed. Request a consultation from Hall CPA at go.therealestatecpa.com/3KSEev6 Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ 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.

    390. The Tax Elections You Might Already Be Stuck With (And How to Save Up to $40,000)

  2. 5 days ago

    Why a Will Isn't Enough: The Estate Planning Mistakes Investors Keep Making

    Why aren't we putting more emphasis on estate planning? In this episode, Nate Sosa and Thomas Castelli break down the essential estate planning strategies every real estate investor should understand. They cover why a simple will often isn't enough, how living trusts help avoid probate, the importance of powers of attorney and healthcare directives, and how estate planning intersects with tax planning. They also discuss estate tax exemptions, the step-up in basis, gifting strategies, and when more advanced trusts may become necessary as your portfolio grows. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ 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.

    Why a Will Isn't Enough: The Estate Planning Mistakes Investors Keep Making

  3. 4 Aug

    389. Don't Sell Your Land Until You Know This IRS Rule (It Could Cost You 6 Figures)

    Many real estate investors assume that holding land for several years automatically qualifies them for favorable capital gains treatment. Unfortunately, that's not always true. In this episode, we break down one of the most misunderstood areas of real estate taxation: dealer status. You'll learn how the IRS determines whether your land is an investment or inventory, why intent alone isn't enough, and how seemingly small decisions before a sale can dramatically impact your tax bill. We discuss the seven factors courts use to evaluate dealer status, real-world tax court cases, why 1031 exchanges and installment sales may no longer apply if you're classified as a dealer, and how entity structuring may help strengthen your position. Whether you're land banking, flipping properties, developing real estate, or simply planning your next investment, understanding these rules could save you hundreds of thousands of dollars in unnecessary taxes. Request a consultation from Hall CPA at go.therealestatecpa.com/3KSEev6 Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ 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.

    389. Don't Sell Your Land Until You Know This IRS Rule (It Could Cost You 6 Figures)

  4. 30 Jul

    Too Big for REPS? The Tax Question Every Real Estate Operator Should Ask

    Many real estate investors assume that as their business grows, qualifying for Real Estate Professional Status becomes automatic. The reality is much more complicated. In this episode, Nate and Tom tackle the question: Can you become too big for REPS? They break down what actually qualifies as material participation, whether capital raising counts toward REPS, how delegation changes the analysis, and why large syndicators and fund managers need to understand the difference between running a real estate business and simply owning one. The discussion also covers notable tax court cases, President Trump's publicly discussed tax returns, common REPS misconceptions, and planning considerations as your portfolio grows. In this episode, you'll learn: - What Real Estate Professional Status actually requires. - Whether CEOs, fund managers, and syndicators can still qualify. - Why scaling your business may or may not affect your tax benefits. - The IRS's position on material participation. - Common REPS myths that continue circulating in the industry. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ 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.

    Too Big for REPS? The Tax Question Every Real Estate Operator Should Ask

  5. 28 Jul

    388. Trump Accounts: What You Need to Know Now That They're Live with Jacob Orr

    Trump Accounts are now live, giving parents and grandparents another option for saving and investing on behalf of their children. In this episode of the Tax Smart REI Podcast, Thomas Castelli, Jacob Orr, and Nate Sosa discuss how Trump Accounts work, who qualifies, how the government's $1,000 contribution is claimed, and where these accounts fit alongside strategies like 529 plans, Roth IRAs, and hiring your children in your business. In this episode, you'll learn: - Who qualifies for the $1,000 government contribution - Annual contribution limits - How contributions and withdrawals are taxed - How Trump Accounts compare to 529 plans - When a Roth conversion may make sense Request a consultation from Hall CPA at go.therealestatecpa.com/3KSEev6 Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/?u…copy_hyperlink 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.

    388. Trump Accounts: What You Need to Know Now That They're Live with Jacob Orr

  6. 23 Jul

    What's Next for Commercial Real Estate? According to a Broker Behind $10 Billion in Deals

    Commercial real estate is changing, and the smartest investors are already adapting. In this episode, Nate Sosa and Thomas Castelli sit down with Mark Sinnett, Head of Capital Markets for Quebec at Avison Young. After closing more than 800 commercial real estate transactions totaling over $10 billion, Mark shares what institutional investors are seeing before everyone else. They discuss: - Why retail may be the biggest opportunity today - Whether office buildings are making a comeback - What's really happening in multifamily housing - How sale-leaseback transactions create massive liquidity - The role AI will play in commercial real estate - Why every investor needs multiple exit strategies If you invest in commercial real estate or want to understand where institutional capital is moving, this episode is important for you. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ 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.

    What's Next for Commercial Real Estate? According to a Broker Behind $10 Billion in Deals

  7. 21 Jul

    387. How a Pizza Guy Acquired 2,000 Apartment Units & $400M in Assets With Gino Barbaro

    How does someone go from working in their family's Italian restaurant to building a $400 million multifamily real estate portfolio? In this episode, Gino Barbaro shares the lessons that transformed his life, from losing money in his first investment to building over 2,000 apartment units with his partner Jake Stenziano. We discuss: - Why today's multifamily market looks surprisingly similar to 2013 - How to build a buy box that helps you avoid bad deals - Why seller financing is making a comeback - What most investors misunderstand about market cycles This conversation combines practical investing advice with the mindset shifts that make success possible. Request a consultation from Hall CPA at go.therealestatecpa.com/3KSEev6 Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/?u…copy_hyperlink 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.

    387. How a Pizza Guy Acquired 2,000 Apartment Units & $400M in Assets With Gino Barbaro

  8. 16 Jul

    The New Housing Bill and the Future of Institutional Investors with Troy Silfies

    Update: The 21st Century ROAD to Housing Act became law on July 11, 2026, after President Trump neither signed nor vetoed the bill within the constitutional deadline. In this episode, Nathan sits down with Troy Silfies, VP of Tax at Hall CPA, to discuss the new 21st Century Housing Bill and what it could mean for investors, builders, landlords, lenders, and prospective homebuyers. Together, they examine the proposed 350-home threshold for large institutional investors, the bill's key exceptions, build-to-rent developments, rent-to-own programs, manufactured housing, and other provisions that could influence housing supply and real estate investment. If you invest in real estate, this conversation will help you understand what's changing, what could happen next, and how the legislation may affect the market. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ 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.

    The New Housing Bill and the Future of Institutional Investors with Troy Silfies
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About

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

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