Tax Smart Real Estate Investors Podcast

By Hall CPABusiness

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Tax Smart Real Estate Investors Podcast episodes

October 22 $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.
41 min
October 20 400. 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.
41 min
October 15 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.
50 min
October 13 399. 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.
37 min
October 08 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.
28 min
October 06 398. 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.
32 min
October 01 Investing in the “Infrastructure of Daily Life”: Express Car Washes, Oil Changes, Healthcare, & More with Chris Salerno
What happens when a real estate investor decides traditional multifamily no longer offers the opportunities it once did?
In this episode of the Major League Real Estate Podcast, Nate and Tom sit down with Chris Salerno, founder and CEO of QC Capital Group, to discuss why he moved beyond multifamily into express car washes, oil changes, flex industrial real estate, healthcare, and other alternative investments.
Chris shares how he looks for investments tied to the “infrastructure of daily life” and why cash flow and tax benefits play such a big role in his strategy.
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.
46 min
September 29 397. How a Pharmacist Built a 14-Property Student Housing Portfolio with Ryan Chaw
Ryan Chaw went from working long shifts as a pharmacist to owning 14 student rentals with 90 tenants. He joins Tom and Nate to explain how he built his portfolio using a rent-by-the-room strategy while still working his W-2 job.
Ryan talks about the expensive mistakes he made on his first property, what he looks for when buying student rentals, and how he manages his portfolio. He also shares how rental income allowed him to leave his full-time job behind and how real estate impacted his tax situation.
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
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.
36 min
September 24 Why This $100M+ Investor Traded Apartments for Manufactured Homes With John Cohen
John Cohen, co-founder of Toro Real Estate Partners and JC Property Group, joins Nate and Tom to break down a real estate journey that started with $300 tax deed auctions and grew into hundreds of millions in multifamily, land, and development deals.
John explains why he and his team sold almost their entire multifamily portfolio between 2020 and 2023 right before interest rates spiked, why he believes multifamily is a great long-term hold but a terrible short-term play right now, and why he's shifted his focus to buying land and putting brand-new manufactured homes on it for first-time homebuyers using FHA and USDA financing.
The conversation covers deal economics, unlevered 20–30% return targets, why he avoids traditional debt on his land deals, his take on the data center land rush, and the biggest lessons and mistakes he's seen after more than a decade investing through multiple market cycles.
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.
39 min
September 22 396. 60 Days Left To Buy A Short-Term Rental For 2026 Tax Savings
With Q4 underway, time is running out to put the short-term rental tax strategy to work for 2026. In this episode of the Tax Smart REI Podcast, Tom and Nate sit down with returning guest Justin Shore to break down the real "60-day countdown" investors face if they want to close on a property, get it rented, and qualify for STR tax benefits before year-end.
They cover how many guest stays you actually need, why personal use in year one can wreck your deductions, what really counts toward the 100-hour material participation test, the gray areas around travel time and "barter" stays with influencers, and why cost segregation timing matters less than people think. They close with a look at the excess business loss limitation and what to do if you don't make the 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 & 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.
35 min

About Tax Smart Real Estate Investors Podcast

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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.