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. 380. The IRS May Owe You a COVID-Era Refund: What to Know Before July 2026

    1d ago

    380. The IRS May Owe You a COVID-Era Refund: What to Know Before July 2026

    Did you pay IRS penalties or interest during the COVID years? The IRS may owe you a refund. In this episode, Thomas Castelli and Nathan Sosa break down two major court cases that could impact taxpayers who paid penalties and interest between 2020 and 2023. They explain why recent court rulings have challenged the IRS's interpretation of COVID-era tax relief, who may be eligible for a refund, and what steps you should take before the July 2026 deadline. You'll learn: - Why the IRS's handling of COVID-era penalties and interest is being challenged - How the Kwong and Abdo cases could affect taxpayers - Who may qualify for a refund - How to check your IRS transcripts for potential claims - What a protective claim is and why filing one may be important - Why real estate investors and business owners should pay particular attention Plus, Thomas and Nathan answer a listener question about short-term rental tax strategy, cost segregation studies, and how personal use can impact your ability to utilize losses. Important: This opportunity is not guaranteed, and the IRS is continuing to challenge portions of these rulings. However, taxpayers may need to take action before July 10, 2026, to preserve their rights. If you're wondering whether you may qualify, this is an episode you won't want to miss. 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 Register for the FREE Investing Debate: go.therealestatecpa.com/debate 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.

    23 min
  2. MLRE: What Every Syndicator Gets Wrong About Depreciation Recapture

    6d ago

    MLRE: What Every Syndicator Gets Wrong About Depreciation Recapture

    What happens when a real estate syndication exits and all that bonus depreciation comes back into play? In this episode, Nate Sosa and Thomas Castelli break down depreciation recapture, cost segregation, and the tax implications GPs and LPs need to understand before selling a deal. Topics discussed include: - Bonus depreciation and cost segregation - Depreciation recapture mechanics - 1245 vs. 1250 vs. 1231 gains - 1031 exchanges in syndications - Refinancing strategies - Partial asset dispositions - LP communication and tax planning - Time value of money and tax deferral Request a free discovery meeting: go.therealestatecpa.com/mlre 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.

    18 min
  3. 379. From Losing $100K to 17 Rentals Without a Property Manager with Becky Nova

    May 26

    379. From Losing $100K to 17 Rentals Without a Property Manager with Becky Nova

    Former cancer researcher Becky Nova transformed financial hardship into a thriving real estate portfolio spanning New York and the Dominican Republic. In this episode, Becky shares how she went from losing over $100,000 in a failed business overseas to building a 17-door portfolio through house hacking, strategic acquisitions, and remote property management. In this episode, we cover: - How Becky house hacked her first duplex in Yonkers - Scaling to 17 units across multiple markets - Investing in the Dominican Republic remotely - Building systems for self-managing rentals - Why she avoids “hot markets” from social media lists - Tax strategy lessons from working with multiple CPAs - The rise of the Lady Landlords community - Real estate investing as a path to financial independence 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 Register for the FREE Investing Debate: go.therealestatecpa.com/debate Submit your question for Tom & Nathan: go.therealestatecpa.com/question Join Lady Landlords: https://www.facebook.com/groups/LadyLandlords/ 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.

    52 min
  4. MLRE: The Hidden Tax Problems Inside Real Estate Syndications

    May 21

    MLRE: The Hidden Tax Problems Inside Real Estate Syndications

    In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down what happens when experienced CPAs integrate directly with syndicators and fund managers. Topics Covered: - Common operating agreement tax mistakes - Entity structuring and partnership considerations - K-1 season expectations and extension strategies - 1031 exchanges, refinance considerations, and exit planning - How to choose the right CPA for your syndication business Most syndicators think their CPA’s job starts and ends with filing partnership tax returns and sending out K-1s. But in reality, the right CPA should function as a strategic partner throughout the entire lifecycle of your deal. Request a free discovery meeting: go.therealestatecpa.com/mlre 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.

    24 min
  5. 378. The Truth About Paying Your Kids Legally (And Whether The IRS Cares)

    May 19

    378. The Truth About Paying Your Kids Legally (And Whether The IRS Cares)

    Can you legally pay your children through your business and use it to build tax-free wealth for their future? In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa break down one of the most powerful family tax strategies available to business owners and real estate investors. You’ll learn: - How to legally pay your kids through your business - The entity structures required to avoid payroll taxes - What jobs children can reasonably perform - How much you can realistically pay them - Roth IRA strategies for children - Trump Accounts vs. 529 Plans If you're a real estate investor or business owner with kids, this episode could completely change how you think about family wealth building and tax planning. 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 Register for the FREE Investing Debate: go.therealestatecpa.com/debate 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
  6. MLRE: How to Raise Capital Legally for Real Estate Deals with Attorney Mola Bosland

    May 14

    MLRE: How to Raise Capital Legally for Real Estate Deals with Attorney Mola Bosland

    In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli sit down with securities and real estate attorney Mola Bosland to break down the legal and strategic side of real estate syndications. Mola shares how successful syndicators structure their entities, when to use a 506(b) vs. 506(c), the biggest mistakes new operators make when raising capital, and why investor trust matters more than flashy projections. The conversation also dives into fund structures, private equity partnerships, preferred returns, investor relations, and the growing institutionalization of real estate investing. Whether you’re raising capital for your first deal or scaling into larger funds and family office partnerships, this episode is packed with actionable guidance to help you stay compliant, protect investors, and grow sustainably. Request a free discovery meeting: go.therealestatecpa.com/mlre 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.

    40 min
  7. 377. You Can't Escape Depreciation Recapture (But Here's How to Defer It)

    May 12

    377. You Can't Escape Depreciation Recapture (But Here's How to Defer It)

    What happens when you sell a rental property after taking depreciation deductions? Many investors are shocked to learn they may owe more than just capital gains tax. In this episode, Thomas Castelli and Nate Sosa break down how depreciation recapture actually works, including the three different tax “buckets” investors need to understand: Section 1245 recapture, unrecaptured Section 1250 gain, and Section 1231 capital gains. They explain how bonus depreciation, cost segregation studies, and qualified improvement property impact your taxes when you sell and why accelerated depreciation can still make sense despite future recapture. If you own rental properties, short-term rentals, or commercial real estate, this episode will help you understand what taxes to expect when exiting a deal and how to plan ahead to minimize them. 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.

    31 min
  8. MLRE: S Corps, C Corps & Syndications: The Structuring Mistakes Investors Make

    May 7

    MLRE: S Corps, C Corps & Syndications: The Structuring Mistakes Investors Make

    Should your real estate syndication use an S corporation, a C corporation, or an LLC taxed as a partnership? In this episode, Thomas Castelli and Nate Sosa break down the real tax implications behind entity structuring for syndicators, fund managers, and passive investors. They explain why LLCs taxed as partnerships are typically the gold standard for real estate syndications, where S corps can accidentally limit depreciation benefits, and how C corps can create double taxation problems that investors often overlook. You’ll also learn: - Why depreciation and debt allocation matter so much in syndications - The hidden limitations of S corps for real estate investors - When a C-corp blocker actually makes sense - How GP entities and management companies should be structured - The biggest mistakes syndicators make before raising capital 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.

    19 min
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424 Ratings

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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