Tax Smart Real Estate Investors Podcast

Hosted by Hall CPA

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460

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Oct 2026

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About the show

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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60 recent

November 5, 202632 min

From Losing Everything as an LP to Owning 1,500+ Apartment Units with Gary Lipsky

On this episode of the Major League Real Estate Podcast, Nate and Tom talk with Gary Lipsky, founder of Break of Day Capital, a firm that buys and operates workforce apartment communities in the Southwest, mostly in Tucson, Arizona. Before real estate, Gary built an after-school education company to more than 700 employees. Gary shares the lessons from losing all his money as a passive investor, including chasing a 25% IRR and relying on a friend’s due diligence. He also explains why he focuses on one asset class in a few markets, and how he has operated through a tough cycle of near 100% staff turnover, flat NOI, and a six-month refinance. 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 Gary: https://www.linkedin.com/in/gary-lipsky/ https://breakofdaycapital.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.

November 3, 202624 min

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

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.

October 29, 202636 min

From $70M in Personal Guarantees to Debt-Free Investing with Joel Friedland

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.

October 27, 202635 min

401. Dave Meyer Returns to Score His 2024 Real Estate Predictions (and Makes New Ones)

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. 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 To learn more about how oil and gas can support your tax strategy and long-term income goals: eckardenterprises.com/taxsmartrei/?u…copy_hyperlink 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 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.

October 22, 202641 min

$100B+ in Deals After Thinking She’d Get Fired at Morgan Stanley: Deb Smith

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.

October 20, 202640 min

400. The Core Tax Strategy Blueprint: The Plan We Give Our Top Clients

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.

October 15, 202649 min

Investing by Gut Feeling? Why Data Beats It “by a Million Miles” with Neal Bawa

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.

October 13, 202636 min

399. Thinking About a 1031 Exchange? 5 Key Questions to Consider with Julia Fritzlen

In this episode of the Tax Smart REI podcast, Tom and Nate welcome Julia Fritzlen 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.

October 8, 202627 min

Claim Denied: The Insurance Mistakes That Could Cost You

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.

October 6, 202631 min

398. 4 Ways Your Short-Term Rental Occupancy Tax Can Go Wrong with Serena Verma

Airbnb may be collecting occupancy tax for you, but that doesn't mean you're in the clear. In this episode of the Tax Smart REI podcast, Tom and Nate talk with Serena Verma, founder of Hostvisors and Monterra Tax, about an audit that uncovered $250,000 in tax exposure and the four ways occupancy tax goes wrong: over-collection, under-collection, over-remittance, and under-remittance. She also explains why platforms like Airbnb, VRBO, Booking.com, and Expedia don't always get it right, why you may still owe a zero-dollar return, how far back auditors can look, and what to check first if you've been hosting for years without reviewing your bookings. Connect with Serena at monterratax.com and hostvisors.com 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 & Nathan: go.therealestatecpa.com/question To learn more about how oil and gas can support your tax strategy and long-term income goals: https://eckardenterprises.com/taxsmartrei/?utm_source=taxsmartrei&utm_medium=podcast_ad&utm_campaign=taxsmartrei_podcast_2026&utm_content=podcast_ad_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.