PODCAST · business
Tax Smart Real Estate Investors Podcast
by 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 podca
Episodes
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395. Debunking 5 Material Participation Myths Real Estate Investors Keep Getting Wrong
Material participation is one of the most important and misunderstood tax rules for real estate investors. In this episode of the Tax Smart REI Podcast, Tom and Nate debunk five common myths involving Real Estate Professional Status (REPS), short-term rentals, the 100-hour test, property…
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Why Mobile Home Parks Might Be the Best Tax Play in 2026 with Michael Pansolini
Michael Pansolini went from PwC and Brookfield to buying mom-and-pop mobile home parks. In this episode, he breaks down why he believes the asset class presents such a compelling opportunity for real estate investors. Michael joins Nate and Tom to explain how his experience underwriting...
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394. 10 Years of Hall CPA: From Startup to a $17M Real Estate CPA Firm with Brandon Hall
Hall CPA is officially 10 years old, and Founder & CEO, Brandon Hall is back on the Tax Smart REI Podcast to talk about how the firm got to where it is today. In this special anniversary episode, Brandon joins Tom and Nate to look back at Hall CPA’s journey from answering real estate tax…
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The 1031 Exchange Holding Period Myth with Matthew Rappaport (Part 2)
In Part 2 with tax attorney Matthew Rappaport, we go deeper into the complexities of 1031 exchanges for real estate partnerships. Matt breaks down the holding-period myth behind drop-and-swaps, why transaction sequencing matters, and how the risks can differ in California and New York. We also...
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393. The Truth About Buying a Short-Term Rental for Tax Benefits: Joey Linn’s First Deal, a Flood & What He Learned
Joey Linn went from covering NBA stars for Sports Illustrated to buying and remotely managing his first short-term rental in Michigan City, Indiana. The original motivation? A growing business had created a significant tax problem, and Joey saw short-term rental real estate as an opportunity to...
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What Investors Get Wrong About 1031 Exchanges & Drop and Swaps with Matthew Rappaport (Part 1)
This week on the Major League Real Estate Podcast, we're kicking off a two-part conversation with tax attorney Matthew Rappaport, Chair of the Taxation and Private Client Groups and Vice Managing Partner at Falcon Rappaport & Berkman. In Part 1, Nate and Matthew break down what happens when real...
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392. Could Trump Index Capital Gains for Inflation and Lower Your Tax Bill?
Could capital gains taxes eventually be adjusted for inflation, and could the home sale exclusion increase from $500,000 to $1 million for married couples filing jointly? In this episode of the Tax Smart REI Podcast, Nate Sosa and Justin Shore break down the discussion around capital gains...
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Advanced Estate & Trust Tax Strategies for Real Estate Investors (And Why They Matter)
In this MLRE episode, Nate and Tom continue their estate and trust planning series by exploring more advanced strategies investors should understand. They break down grantor vs. non-grantor trusts, intentionally defective grantor trusts, the trade-off between estate tax savings and the step-up in...
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391. Can This “Disaster Relief” Tax Strategy Really Offset W-2 Income?
In this episode, Tom and Nate break down a disaster relief housing promotion involving metal container housing, special grantor trusts, material participation, and significant first-year depreciation deductions. They also examine additional red flags surrounding the financing, at-risk rules,...
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5 Real Estate Syndication Tax Questions Every LP Should Know
In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down some of the most common tax questions real estate sponsors hear from limited partners. When should LPs expect their K-1s? Can passive real estate losses offset W-2 income? Do you need an LLC to…
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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...
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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...
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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...
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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...
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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...
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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...
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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...
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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…
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386. 5 Tax Scams That Could Get You Audited in 2026
Every year, real estate investors are pitched "exclusive" tax strategies that promise massive deductions, tax-free sales, or unbelievable savings. The problem? Many of these strategies collapse under IRS scrutiny and taxpayers are left paying the price. In this episode, Nate Sosa and Justin Shore...
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Opportunity Zones 2.0: The Biggest Changes Coming in 2027
Qualified Opportunity Zones are back, and they're better than ever. With Opportunity Zones 2.0 becoming permanent under the new tax law, investors and real estate operators have a rare opportunity to reduce capital gains taxes while building long-term wealth. But the rules have changed. In this...
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385. How To 1031 Exchange Into Oil & Gas (Instead of Another Rental Property) with Khris Allen
Most investors think a 1031 exchange only means selling one property to buy another. But what if there was another option? In this episode, we're joined by Khris Allen, Director of 1031 Exchange Services at Eckard Enterprises, to discuss how investors can use a 1031 exchange to acquire oil, gas,...
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The Case for Manufactured Housing: America's Most Durable Real Estate Asset with "Ali" Nasir Ali
Today's manufactured housing communities are becoming one of the strongest-performing real estate asset classes available. In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli sit down with Ali, Managing Director and Co-Founder of Rise360 Ventures, whose family…
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384. From $2.5M to $350K in Tax Savings: The RV Park Strategy
RV parks have become one of the fastest-growing alternative real estate investments, but are the tax benefits really as good as people claim? In this episode, Thomas Castelli, CPA and Nate Sosa break down exactly how RV parks are taxed, why investors can often get significantly more bonus...
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383. The $60,000 Tax Question: Expense It or Depreciate It?
Should you expense a rental property cost immediately or capitalize and depreciate it over time? It's one of the most misunderstood areas of real estate investing and getting it wrong can cost you thousands in missed deductions or IRS headaches. In this episode, Thomas Castelli and Nate Sosa…
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Why This Airline Pilot Chose Passive Investing (Oil & Gas, Senior Living, & More) with Tait Duryea
In this episode, Nathan Sosa sits down with Tait Duryea, Founder and CEO of Turbine Capital, for part one of the active vs. passive investing debate. Tait shares how he went from airline pilot to building an investment firm and explains why many high-income professionals are turning to passive...
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382. Can Real Estate Developers Use Cost Segregation & Bonus Depreciation?
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down one of the most misunderstood areas of real estate taxation: how developers are taxed and when they can (and can't) take advantage of cost segregation and bonus depreciation. They explain the key difference...
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What Happens When an Investor Dies, Sells, or Gets Bought Out? Understanding Section 754 Elections
What happens when an investor dies, sells their partnership interest, or gets bought out of a real estate syndication? In this episode, Thomas Castelli and Nate Sosa explain Section 754 elections and how they affect real estate syndications, private equity funds, and partnership structures. They...
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381. The Top Entity Structuring Mistakes We've Seen (LLCs, S Corps, and Partnerships)
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Justin Shore break down some of the most common entity structure mistakes they see with real estate investors. They discuss when S corporations make sense (and when they don't), why rental properties generally shouldn't be held in…
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MLRE: 1031 Exchange Capital in Syndications: TICs, DSTs, and UPREITs Explained
Can investors use 1031 exchange proceeds to invest in real estate syndications? The answer is yes, but it's not nearly as simple as many sponsors hope. In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down the most common structures used to bring 1031...
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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…
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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…
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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...
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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…
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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…
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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…
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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...
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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...
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376. The Depreciation Mistake That Could Cost You at Audit (And Baby Roths)
In this Q&A episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa answer real questions from listeners, clients, and the Tax Smart community. They cover a wide range of topics, from how to properly track your time for material participation, to how short-term rentals should be...
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MLRE: Why 1031 Exchanges Break in Syndications (And How to Work Around It)
In this episode of the Major League Real Estate Podcast, we break down everything you need to know about 1031 exchanges and why they get complicated fast when syndications are involved. We cover: - Why you can’t directly 1031 into a syndication - The biggest issues GPs and LPs run into when…
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375. Why S Corporations Are a Disaster for Rental Properties (And How to Get Out)
If you’ve ever been told to put your rental properties in an S corporation…this episode could save you thousands (or more) in taxes. In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa break down one of the most common and expensive mistakes real estate investors make:...
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MLRE: K-1s, Deadlines, and Tax Extensions: How Tax Season Is Hurting Your Long Game
In this episode, we’re breaking down one of the biggest misconceptions in real estate investing: the idea that you need to rush to file your taxes by April 15. If you’ve ever felt pressure to get your K-1s out early, file on time, or keep investors happy by hitting arbitrary deadlines, this…
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374. How People Make $50K Tax-Free Renting Their Home (Augusta Rule)
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down the Augusta Rule, one of the most talked-about and misunderstood tax strategies in real estate. In this episode, we cover: - Where the Augusta Rule came from and how it ended up in the tax code - Who actually...
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MLRE: Carried Interest: What’s Really Behind the “Loophole” and Why It's Misunderstood
In this solo episode, Nate Sosa breaks down one of the most important — and most misunderstood — concepts in real estate syndication: carried interest. From its surprising origins in 16th-century shipping voyages to its modern-day use in private equity and real estate deals, Nate walks through…
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373. Insurance Mistakes Real Estate Investors Are Making (And What They’re Costing You)
Most real estate investors spend a lot of time learning how to build wealth, but far fewer know how to protect it when disaster comes. In this episode, Thomas and Nate sit down with Michael Fried, Vice President and Partner at Strategic Claim Consultants, to break down what real estate investors...
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MLRE: Why Multifamily Is Still Uninvestable (And Where Smart Money Is Going Instead) With Brian Burke
Brian Burke, CEO of Praxis Capital and author of The Hands-Off Investor, joins the show to break down the current state of real estate investing and why he believes multifamily is still too early to touch. We discuss: - Why the multifamily market looks like a “traffic collision” right now - The...
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372. How Top Investors Handle Tax Deadlines (Strategic Extensions Explained)
Tax extensions aren’t something to avoid. They’re something to understand and use strategically. In this episode, Nate Sosa and guest co-host Justin Shore break down why filing an extension is a normal (and often smart) move, even for tax professionals. They explain how extensions give you more...
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MLRE: Disguised Sales: How Refinances Can Trigger Unexpected Taxes in Syndications
In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa break down one of the most misunderstood areas of partnership tax law: disguised sales. While many investors assume distributions and refinance proceeds are tax-free, the rules change when partnerships and...
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371. Why Your Tenants Leave (And How to Fix It Fast) with Ryan Barone
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa sit down with Ryan Barone, co-founder and CEO of RentRedi, to break down how real estate investors can simplify property management, reduce tenant turnover, and increase ROI using automation and data. You’ll learn…
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MLRE: How He Built a $1B Multifamily Portfolio (Without Third-Party Managers) with Rob Beardsley
In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa sit down with Rob Beardsley, founder and CEO of LSCRE, to break down what it really takes to scale a vertically integrated multifamily business in today’s market. Rob shares how his firm grew to nearly $1…
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370. Two Major Housing Changes Investors Need to Know: Senate Housing Bill + FinCEN Reporting
Two major housing developments just hit real estate investors in a short window, and both could have a big impact on how you buy, hold, and scale residential real estate. In this episode of the TaxSmart REI Podcast, Thomas Castelli and Nate Sosa break down the Senate’s 21st Century Road to…
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ABOUT THIS 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 podca
HOSTED BY
Hall CPA
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Frequently Asked Questions
How many episodes does Tax Smart Real Estate Investors Podcast have?
Tax Smart Real Estate Investors Podcast currently has 452 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Tax Smart Real Estate Investors Podcast 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...
How often does Tax Smart Real Estate Investors Podcast release new episodes?
Tax Smart Real Estate Investors Podcast publishes regularly with 452 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Tax Smart Real Estate Investors Podcast?
You can listen to Tax Smart Real Estate Investors Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Tax Smart Real Estate Investors Podcast?
Tax Smart Real Estate Investors Podcast is created and hosted by Hall CPA.
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