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Artwork for Tax Smart Real Estate Investors Podcast

Tax Smart Real Estate Investors Podcast

Hall CPA
Short-Term Rentals
Real Estate Investment
Bonus Depreciation
Real Estate Professional Status
Real Estate
Tax Strategies
Tax Strategy
Cost Segregation
1031 Exchange
Depreciation
Real Estate Investing
Cost Segregation Studies
IRS Audits
Tax Benefits
IRS
Real Estate Syndication
Investment Strategies
Tax Savings
Estate Planning
Tax Planning

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 goa... more

PublishesTwice weeklyEpisodes452Founded10 years ago
Number of ListenersCategory
Business

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Artwork for Tax Smart Real Estate Investors Podcast

Latest Episodes

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 ... more

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 ... more

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.... more

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" investor... more

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Recent Guests

John Cohen
Co-founder of Toro Real Estate Partners and JC Property Group
Toro Real Estate Partners / JC Property Group
Episode: Why This $100M+ Investor Traded Apartments for Manufactured Homes With John Cohen
Michael Pansolini
New York CPA with a background at PwC, Brookfield; founder of Archangel and MHP-related ventures
Archangel, MHP Pros
Episode: Why Mobile Home Parks Might Be the Best Tax Play in 2026 with Michael Pansolini
Matthew Rappaport
Attorney; expert on tax law and real estate structuring
FRB Law
Episode: The 1031 Exchange Holding Period Myth with Matthew Rappaport (Part 2)
Joey Linn
Clippers writer turned real estate investor and finance/real estate writer for The Street
The Street / Sports Illustrated (past)
Episode: 393. The Truth About Buying a Short-Term Rental for Tax Benefits: Joey Linn’s First Deal, a Flood & What He Learned
Jacob Orr
Senior Tax Advisor, Hall CPA
Hall CPA, PLLC
Episode: 388. Trump Accounts: What You Need to Know Now That They're Live with Jacob Orr
Mark Sinnett
Runs Capital Markets for all of Quebec at Avison Young; has prior roles at CBRE, JLL
Avison Young
Episode: What's Next for Commercial Real Estate? According to a Broker Behind $10 Billion in Deals
Gino Barbaro
Co-founder of Jake and Gino, multifamily real estate educator
Jake and Gino
Episode: 387. How a Pizza Guy Acquired 2,000 Apartment Units & $400M in Assets With Gino Barbaro
Troy Silfies
VP of Tax, Hall CPA
Hall CPA
Episode: The New Housing Bill and the Future of Institutional Investors with Troy Silfies
Khris Allen
Director of 1031s at Eckard Enterprises
Eckard Enterprises
Episode: 385. How To 1031 Exchange Into Oil & Gas (Instead of Another Rental Property) with Khris Allen

Hosts

Nathan Sosa
Host-level expert from a real estate-focused CPA firm with deep experience in real estate tax planning and strategy.
Tom Costelli
Co-host with strong background in real estate taxation and education, frequently guiding episode discussions with practical tax strategy.
Nate
Co-host who drives technical tax discussions and real estate investment analysis topics.
Justin Shore
Host of Tax Smart REI Podcast; contributes tax strategy expertise and podcasting presence.

Reviews

4.8 out of 5 stars from 527 ratings
  • RE investors best friend podcast

    OK so you might not really enjoy the tax aspect of real estate investing but you’re smart enough to know understanding the landscape is pretty important. Text smart real estate investors podcast gives you great tools, and understanding of how important proper tax planning is for our business.. They speak with authority and at a level of understanding for even new investors. This has become a Top podcast in our rotation. Looking forward to a consult as well because these guys know their stuff.

    Apple Podcasts
    5
    antnyc.com
    United States7 months ago
  • Packed with useful tips and info

    Love how these two pack every episode full of information and use examples to explain how things actually apply and play out. Great show for more experienced investors who diversify across asset classes.

    Apple Podcasts
    5
    FINE and loving it!
    United Statesa year ago
  • Excellent!

    Really practical advise for real estate investors

    Apple Podcasts
    5
    Danielle Igh
    United Statesa year ago
  • Real estate tax strategies

    Extremely helpful podcasts for new and experienced investors

    Apple Podcasts
    5
    Dochow11
    United Statesa year ago
  • Glad This Exists

    Excellent podcast for investors

    Apple Podcasts
    5
    Nick from WVU
    United Statesa year ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners praise the show for practical tax strategies and clear explanations.
The content is considered valuable for both new and experienced real estate investors, often citing case law and tax codes.
Guests are described as knowledgeable and real-world focused.

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Talking Points

Recent interactions between the hosts and their guests.

396. 60 Days Left To Buy A Short-Term Rental For 2026 Tax Savings
Q: How should travel time be treated in calculating material participation?
Travel time can count if it is clearly for work on the property and you have a home base for operations, but it is risky and often disallowed by IRS; contemporaneous evidence and a clear work purpose are essential.
396. 60 Days Left To Buy A Short-Term Rental For 2026 Tax Savings
Q: What are the biggest hurdles besides closing, and how can investors prepare?
The biggest hurdle is securing bookings and achieving the required number of stays within the year, along with proper time logging and documentation to prove material participation, not just planning.
396. 60 Days Left To Buy A Short-Term Rental For 2026 Tax Savings
Q: What is a realistic timeline to close on a short-term rental if you want to place it in service by year-end?
A realistic window often tightens to about 30 days for closing, but you should plan for extra time to get the property ready, with a strong emphasis on getting two guest stays and meeting the 100-hour material participation requirement.
Why This $100M+ Investor Traded Apartments for Manufactured Homes With John Cohen
Q: What is the biggest mistake newer investors make, and how can they avoid it?
Many assume it will always go up and underestimate the importance of stress-testing deals against higher interest rates, vacancies, and rent declines, so they over-leverage or misprice risk; the remedy is market-specific research, conservative underwriting, and scenario planning.
Why This $100M+ Investor Traded Apartments for Manufactured Homes With John Cohen
Q: What was the biggest lesson you learned throughout your investing journey?
The key takeaway is that there is no true passive real estate; ongoing effort, education, and knowing when to stay in or exit are critical, with a focus on time in the market and informed decisions rather than chasing quick gains.

Audience Metrics

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Frequently Asked Questions About Tax Smart Real Estate Investors Podcast

What is Tax Smart Real Estate Investors Podcast about and what kind of topics does it cover?

Tax-focused real estate investing sessions that break down complex tax, accounting, and structuring topics into practical, actionable guidance. Episodes routinely cover high-impact areas like estate planning, 1031 exchanges, cost segregation, depreciation, and new tax legislation, with guests that provide subject-matter depth across real estate assets and investment strategies. The show leans toward practitioners—CPAs, lawyers, and experienced operators—delivering clear frameworks and real-world examples to help listeners save money and stay compliant. A notable edge is the consistent alignment with a real estate-focused CPA firm, often weaving in firm-backed insights and upcoming tax-law events, which can be valuable for listeners who want... more

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Which podcasts are similar to Tax Smart Real Estate Investors Podcast?

These podcasts share a similar audience with Tax Smart Real Estate Investors Podcast:

1. On The Market
2. BiggerPockets Real Estate Podcast
3. Ken McElroy Show
4. Real Wealth Show: Real Estate Investing Podcast
5. The David Greene Show

How many episodes of Tax Smart Real Estate Investors Podcast are there?

Tax Smart Real Estate Investors Podcast launched 10 years ago and published 452 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Tax Smart Real Estate Investors Podcast?

Recent guests on Tax Smart Real Estate Investors Podcast include:

1. John Cohen
2. Michael Pansolini
3. Matthew Rappaport
4. Joey Linn
5. Jacob Orr
6. Mark Sinnett
7. Gino Barbaro
8. Troy Silfies

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