Episodi

  • 402. The $512K Tax Cap Most High-Income W-2 Earners Don’t Know About

    402. The $512K Tax Cap Most High-Income W-2 Earners Don’t Know About
    Nov 3 2026
    You qualified for real estate professional status or you’re running the short-term rental strategy, and your depreciation losses are offsetting your W-2 income. Then you hit the excess business loss (EBL) limit, which caps those losses at $512,000 for married filing jointly and $256,000 for single filers. In this Tax Smart REI podcast episode, Tom and Nate explain who it affects and why. Losses over the cap don’t disappear. They carry forward as a net operating loss that can offset up to 80% of your taxable income in later years. They also explain why this works best as a multi-year plan and why you should work with a tax advisor instead of doing it on your own. Be the first to hear about our new offering: https://www.therealestatecpa.com/join-the-list/ Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart Join the Hall CPA Team: go.therealestatecpa.com/team Submit your question for Tom & Nate: 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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    25 min
  • From $70M in Personal Guarantees to Debt-Free Investing with Joel Friedland

    From $70M in Personal Guarantees to Debt-Free Investing with Joel Friedland
    Oct 29 2026
    What if the best way to invest in real estate is to skip the debt? In this episode of the Major League Real Estate Podcast, Nate and Tom talk with Joel Friedland, founder and CEO of Brit Properties, a Chicago firm that buys small single-tenant industrial buildings in the Chicago suburbs. After the 2008 crash, Joel rebuilt his syndication business with almost no debt. He shares why debt kills, how a debt-free deal pencils out with a cost segregation example, and how investors can exit in about 30 days. Request a free discovery meeting: go.therealestatecpa.com/mlre 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 Connect with Joel: https://www.linkedin.com/in/joel-friedland/ 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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    36 min
  • 401. Dave Meyer Returns to Score His 2024 Real Estate Predictions (and Makes New Ones)

    401. Dave Meyer Returns to Score His 2024 Real Estate Predictions (and Makes New Ones)
    Oct 27 2026
    Housing prices aren’t crashing, but they aren’t taking off either. BiggerPockets’ Dave Meyer calls this “the great stall.” In this episode of the Tax Smart REI Podcast, Tom and Nate revisit Dave’s 2024 predictions and ask what’s next. Dave explains why he thinks the lock-in effect is getting stronger and why he expects flat to declining real prices for years. He covers where investors can still find opportunity, including buying at a discount and value-add projects. He also shares his views on the AI and data center build-out, rising bond yields, and why patience matters more than anything in this market. Connect with Dave: LinkedIn: https://www.linkedin.com/in/dave-meyer-5660846/ Instagram: https://www.instagram.com/thedatadeli/?hl=en Bigger Pockets Website: https://www.biggerpockets.com/ On The Market Podcast: https://www.biggerpockets.com/podcasts/on-the-market Bigger Pockets Real Estate Podcast: https://www.biggerpockets.com/podcasts/real-estate Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart Join the Hall CPA Team: go.therealestatecpa.com/team Submit your question for Tom & Nate: go.therealestatecpa.com/question To learn more about how oil and gas can support your tax strategy and long-term income goals: eckardenterprises.com/taxsmartrei/?u…copy_hyperlink 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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    36 min
  • $100B+ in Deals After Thinking She’d Get Fired at Morgan Stanley: Deb Smith

    $100B+ in Deals After Thinking She’d Get Fired at Morgan Stanley: Deb Smith
    Oct 22 2026
    What happens when AI makes information a commodity and the old real estate categories stop working? In this episode of the Major League Real Estate Podcast, Nate and Tom sit down with Deb Smith, co-founder and CEO of CenterCap Group, a real estate investment bank, who has worked on more than $100 billion in deals. Deb shares her unexpected path from a dairy farm in rural Australia to Morgan Stanley and the Gables go-private deal. She also tells the story of launching a boutique investment bank in 2009, in the middle of the financial crisis. She explains why office, retail, industrial, and multifamily no longer describe the market, and how niches like IOS, cold storage, senior housing, health and wellness, and sports and entertainment real estate have emerged. Connect with Deb: https://www.linkedin.com/in/deborahsmith-centercap The CenterCap Group: https://centercapgroup.com Request a free discovery meeting: go.therealestatecpa.com/mlre 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.
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    41 min
  • 400. Year-End Tax Strategy Playbook: REPS, STR Loophole & Exit Options

    400. Year-End Tax Strategy Playbook: REPS, STR Loophole & Exit Options
    Oct 20 2026
    In this episode of the Tax Smart REI podcast, Tom and Nate break down the core tax strategy playbook used by real estate investors and high-income earners to minimize their tax burden before year-end. They dive deep into the real estate professional status (REPS) requirements, the short-term rental loophole, grouping elections, cost segregation, and 100% bonus depreciation. They also evaluate exit strategies like 1031 exchanges, lazy 1031s, 721 UPREIT exchanges, and the "Buy, Borrow, Die" model, alongside common business strategies including S-Corp elections, the Augusta rule, employing your children, home office deductions, and oil and gas working interests. Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart Join the Hall CPA Team: go.therealestatecpa.com/team Submit your question for Tom & Nate: go.therealestatecpa.com/question To learn more about how oil and gas can support your tax strategy and long-term income goals: eckardenterprises.com/taxsmartrei/?u…copy_hyperlink 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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    41 min
  • Investing by Gut Feeling? Why Data Beats It “by a Million Miles” with Neal Bawa

    Investing by Gut Feeling? Why Data Beats It “by a Million Miles” with Neal Bawa
    Oct 15 2026
    Neal Bawa, a former tech founder who has invested in apartments since 2013, joins Nate and Tom to talk about using data to make real estate decisions. He explains why he passed on investing in Huntsville, Alabama, despite its growth, and where he sees multifamily rents heading over the next two years. He also discusses how Claude now handles much of his underwriting, from screening incoming deals to pulling comps and building dashboards for about $10 a month in tokens. Neal also gets into why most people who call themselves data-driven aren’t, why he’s buying retiring CPA firms, and what AI means for the accounting profession. Find Neal’s work at: multifamilyu.com Request a free discovery meeting: go.therealestatecpa.com/mlre 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.
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    50 min
  • 399. Thinking About a 1031 Exchange? 5 Questions to Ask Before You Commit with Julia Fritzlin

    399. Thinking About a 1031 Exchange? 5 Questions to Ask Before You Commit with Julia Fritzlin
    Oct 13 2026
    In this episode of the Tax Smart REI podcast, Tom and Nate welcome Julia Fritzlin of Insight Investment Advisors to talk about helping real estate owners exit without a large tax bill. Julia explains how she moved from healthcare equipment financing into 1031 exchanges and Delaware Statutory Trusts (DSTs), and why she starts every conversation by asking what life should look like after the property is gone. The group covers the 45-day and 180-day exchange deadlines, debt boot, what makes a DST a good or poor fit, how illiquid these investments are, and why the investment itself should come before the tax benefit. They close with practical first steps for owners who are approaching a 1031 deadline. Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart Join the Hall CPA Team: go.therealestatecpa.com/team Submit your question for Tom & Nate: go.therealestatecpa.com/question To learn more about how oil and gas can support your tax strategy and long-term income goals: eckardenterprises.com/taxsmartrei/?u…copy_hyperlink 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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    36 min
  • Claim Denied: The Insurance Mistakes That Could Cost You

    Claim Denied: The Insurance Mistakes That Could Cost You
    Oct 8 2026
    Nobody wants to talk about insurance until something goes wrong. In this episode of the Major League Real Estate Podcast, Nate and Tom walk through real court cases and news stories showing how real estate investors lose coverage over technicalities, from misstating a property's use (single-family vs. short-term rental) to deeding it to an LLC or family trust without updating the policy. They also cover outdated replacement-cost estimates and LA fire victims who can't rebuild, flood coverage gaps after Hurricane Helene, a Miami deal killed by insurance quotes, State Farm's exit from California apartment policies, and why umbrella insurance matters when a $50M lawsuit exceeds your property policy. Request a free discovery meeting: go.therealestatecpa.com/mlre 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.
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    28 min