Shows / Tax Smart Real Estate Investors Podcast
Tax Smart Real Estate Investors Podcast
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…
Episodes
Tax Smart Real Estate Investors PodcastFrom $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…
Tax Smart Real Estate Investors Podcast401. 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…
Tax Smart Real Estate Investors Podcast$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…
Tax Smart Real Estate Investors Podcast400. 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…
Tax Smart Real Estate Investors PodcastInvesting 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…
Tax Smart Real Estate Investors Podcast399. 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…
Tax Smart Real Estate Investors PodcastClaim 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…
Tax Smart Real Estate Investors Podcast398. 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…
Tax Smart Real Estate Investors PodcastInvesting 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…
Tax Smart Real Estate Investors Podcast397. 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…
Tax Smart Real Estate Investors PodcastWhy 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…
Tax Smart Real Estate Investors Podcast396. 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…
Tax Smart Real Estate Investors PodcastYour Real Estate Is Insured. But Are You Actually Covered?
Having insurance doesn’t necessarily mean your real estate investment is fully protected. In this episode of the Major League Real Estate Podcast, Tom and Nate…
Tax Smart Real Estate Investors Podcast395. 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…
Tax Smart Real Estate Investors PodcastWhy 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…
Tax Smart Real Estate Investors Podcast394. 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…
Tax Smart Real Estate Investors PodcastThe 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…
Tax Smart Real Estate Investors Podcast393. 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…
Tax Smart Real Estate Investors PodcastWhat 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…
Tax Smart Real Estate Investors Podcast392. 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…
Tax Smart Real Estate Investors PodcastAdvanced 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…
Tax Smart Real Estate Investors Podcast391. 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…
Tax Smart Real Estate Investors Podcast5 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…
Tax Smart Real Estate Investors Podcast390. 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…
Tax Smart Real Estate Investors PodcastWhy 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…
Tax Smart Real Estate Investors Podcast389. 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…
Tax Smart Real Estate Investors PodcastToo 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…
Tax Smart Real Estate Investors Podcast388. 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…
Tax Smart Real Estate Investors PodcastWhat'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…
Tax Smart Real Estate Investors Podcast387. 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…
Tax Smart Real Estate Investors PodcastThe 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…
Tax Smart Real Estate Investors Podcast386. 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?…
Tax Smart Real Estate Investors PodcastOpportunity 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…
Tax Smart Real Estate Investors Podcast385. 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…
Tax Smart Real Estate Investors PodcastThe 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…
Tax Smart Real Estate Investors Podcast384. 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…
Tax Smart Real Estate Investors Podcast383. 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…
Tax Smart Real Estate Investors PodcastWhy 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…
Tax Smart Real Estate Investors Podcast382. 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…
Tax Smart Real Estate Investors PodcastWhat 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…
Tax Smart Real Estate Investors Podcast381. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast380. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast379. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast378. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast377. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast376. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast375. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast374. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast373. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…
Tax Smart Real Estate Investors Podcast372. 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…
Tax Smart Real Estate Investors PodcastMLRE: 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…