HeyJaredTax 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.
- Indexed episodes, last 90 days
- 19
- Latest publication
- Sep 8, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
394. 10 Years of Hall CPA: From Startup to a $17M Real Estate CPA Firm with Brandon Hall (opens the original)
Read excerpt
Hall CPA is officially 10 years old, and CEO & Founder 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 questions online to building a $17 million real estate CPA firm and becoming a Top 400 CPA firm in the United States. Brandon shares the biggest lessons and challenges from the last 10 years, from rapid early gro
The 1031 Exchange Holding Period Myth with Matthew Rappaport (Part 2) (opens the original)
Read excerpt
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 explore partnership divisions under Section 708, why special allocations often don’t work, the limitations of Section 761(a) elections, and what Rev. Proc. 2002-22 actually means for tenancy-in-common arra
393. The Truth About Buying a Short-Term Rental for Tax Benefits: Joey Linn’s First Deal, a Flood & What He Learned (opens the original)
Read excerpt
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 combine potential tax benefits with an appreciating, cash-flowing asset. But his first deal quickly became a real-world education in real estate investing. In this episode, Joey joins Thomas Castelli, CPA
What Investors Get Wrong About 1031 Exchanges & Drop and Swaps with Matthew Rappaport (Part 1) (opens the original)
Read excerpt
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 estate partners want to sell the same property but have different plans for the proceeds. Matthew then goes into partnership 1031 exchanges and the strategy commonly known as a "drop and swap," including
392. Could Trump Index Capital Gains for Inflation and Lower Your Tax Bill? (opens the original)
Read excerpt
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 indexing, how an inflation adjustment to tax basis could work, and why changes to the Section 121 home sale exclusion could have a significant impact on homeowners and real estate investors. Plus, Nate and Jus
Publishing over time
Last 90 days. Choose a month to open its work.
Recurring subjects
Named in the text we hold. One piece can cover several.
Audience
No verified audience measurement yet.
About this data
Counts cover the work we have indexed. Tone needs enough text and a confident classification. Excerpts and episode notes are not full articles or transcripts.
Identity or attribution wrong? Suggest a correction.