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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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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,…
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:…
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…
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…
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…
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…
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,…
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…
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…
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…
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Tax Smart Real Estate Investors Podcast has published 420 episodes since May 2016, covering topics in Business.
Tax Smart Real Estate Investors Podcast is currently highly active with new episodes weekly. Average episode length is 32m.
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