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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 ...
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305. Passive or Non-Passive: What’s New for Short-Term Rentals in 2025
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In this episode, Thomas and Ryan walk you through the short-term rental loophole updates to keep an eye on this year. This episode explores:- The passive activity rules and why the short-term rental strategy is a game-changer.- Material participation tests and the most popular ways to qualify.- How to use cost segregation and bonus depreciation for…
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304. 2025 Tax Changes & The Corporate Transparency Act Update
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In this episode of the Tax Smart REI podcast, Thomas and Ryan address pivotal updates as the year draws to a close. They provide essential insights into the expected 2025 tax changes, the implications of the new administration, and the recent developments regarding the Corporate Transparency Act's enforcement status.Here's what they discuss:- The E…
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303. From Rookie to Mogul: How to Build Rental Real Estate Riches with Travis & Regan Perry
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In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with Travis and Regan Perry, real estate investors who have crafted a flourishing portfolio of short-term rental properties. With roots in Iowa, the Perrys share their journey from purchasing their first home to managing multiple properties across several states.Tune in to learn…
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302. Short-Term Rental Financing: Taxes, Loans, and Winning Strategies with Stacey Dowling
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In this episode of the Tax Smart REI Podcast, Thomas & Ryan sit down with Stacey Dowling, a seasoned mortgage lender specializing in short-term rental financing. Stacey brings over 30 years of experience to the table, offering actionable insights into obtaining loans for short-term rentals.Tune in to learn:- How to qualify for a short-term rental l…
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301. Why the Wealthy Invest differently: Timing, Trends, and Tax Benefits with Ben Fraser
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In this episode, Thomas and Ryan are joined by Ben Fraser, Chief Investment Officer of Aspen Funds and host of the Invest Like a Billionaire podcast, to explore strategies of the ultra-wealthy and how they invest differently.They cover:- The difference between ultra-high-net-worth investors and retail investors- Why private markets, including real …
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300. The 14-Day Rule & Personal Use Days: Avoiding Common Pitfalls for STR Owners
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In this episode of the Tax Smart REI podcast, Thomas and Ryan explore the critical nuances of personal use days for short-term rental properties, a topic that generates frequent questions from their community of real estate investors and tax-savvy listeners.They break down the 14-day rule, share actionable strategies to avoid common pitfalls, and p…
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299. Corporate Transparency Act Checklist: Avoid Costly Mistakes with FinCEN Filing Agents
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In this episode, Thomas and Ryan are joined by Heather and Isaac from FinCEN Filing Agents to dive deep into the 2024 Corporate Transparency Act (CTA) and what it means for real estate investors and small business owners.They cover:- An overview of the Corporate Transparency Act- Key reporting requirements for LLCs and other entities- The penalties…
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298. From Schedule E to Cost Segregation: Tackling Taxes with an Expert Q&A
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In this episode of the Tax Smart REI podcast, Thomas and Ryan dive into real estate tax strategies by addressing audience questions from their public community and Facebook group. Covering crucial topics, they guide listeners through the complexities of tax planning, especially for short-term rental owners, and how they can leverage tax rules to mi…
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297. Drilling Into Profits: A Case Study on Oil & Gas Working Interests with Troy Eckard
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In this episode, Thomas and Ryan are joined again by Troy Eckard of Eckard Enterprises to conclude our oil & gas series with a real-world case study on oil and gas working interests. They cover:- A detailed breakdown of a case study involving a working interest investment, including cost structures, potential pitfalls, and strategies for maximizing…
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296. Top Year-End Tax Strategies: Maximize Deductions Before December 31st
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In this episode, Thomas and Ryan break down year-end tax strategies tailored for real estate investors, providing valuable insights for maximizing tax savings before the year ends.Here’s what they cover:- The advantages of buying a short-term rental before year-end and how to qualify for the short-term rental loophole.- Maximizing vehicle deduction…
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295. The Future of Housing: How Interest Rates and Labor Shape Real Estate with Logan Mohtashami
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In this episode, Thomas and Ryan are joined by renowned analyst and housing expert, Logan Mohtashami, to explore the current state of the housing market, interest rates, and what might be in store for 2025.They cover:- Logan's insights into the factors driving mortgage rates, including the crucial role of labor data and the Federal Reserve's polici…
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294. IRS Red Flags: Why Foradis Failed to Prove REPS with Nathan Sosa, CPA
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In this week's Tax Smart REI episode, Ryan is joined with Nathan Sosa, a Senior Tax Advisor at Hall CPA to dive into a new court case related to real estate professional status.This continues to be a heavily audited topic and with additional IRS funding, the audits will only increase from here.If you're curious about what factors led to this taxpay…
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293. Unpacking EACH Real Estate Investment Strategy: Pros, Cons, and Tax Benefits
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In this episode of the Tax Smart REI podcast, Thomas is joined by frequent guest, Justin Shore, EA for the go-to guide to real estate investment strategies. They break down each strategy, the tax benefits, and the implications. Topics include: - The tax advantages of direct ownership and how to maximize deductions.- The differences between long-ter…
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292. Generate Massive Cash Flow By Investing in Senior Living with Isabelle Guarino
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In this episode of the Tax Smart REI Podcast, Thomas is joined by Isabelle Guarino to discuss investing in residential assisted living facilities. Isabelle shares her personal journey into the space and explains how this business model can generate significant cash flow.Listen now to learn:- The steps to owning and operating these facilities—or jus…
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291. The Power of Section 179 for Commercial Real Estate and Short-Term Rentals w/ Nathan Sosa, CPA
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In this episode of the Tax Smart REI podcast, Thomas Castelli and Nathan Sosa explore the often overlooked Section 179 deduction and its potential benefits for commercial real estate investors and short-term rental owners. As bonus depreciation phases out, Section 179 is becoming more relevant for those looking to immediately expense certain capita…
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290. How to use Equity Losses to Offset Real Estate Capital Gains with Nathan Cook
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In this episode, Thomas is joined by financial advisor Nathan Cook to discuss a powerful strategy for real estate investors: using equity losses from the stock market to offset real estate capital gains through a process called active indexing.They cover key topics such as:- The fundamentals of tax loss harvesting and how it benefits real estate in…
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289. Cutting Out the Middleman: How to Go Direct to Sellers and Boost Your Profits with Scott Morse
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In this episode, Thomas is joined by Scott Morse, founder of Lamassu Leads and host of the "Leads 2 Deals" podcast.Scott specializes in helping real estate investors find motivated sellers and acquire properties through innovative lead generation strategies. Together, Thomas and Scott dive deep into the art of dominating any market by leveraging co…
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288. Analyzing 7,000 Properties: How To Maximize Cash flow Today with Chris Lopez
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In this episode, Thomas and Ryan are joined by Chris Lopez from Property Llama. Chris and his team have analyzed over 7,000 properties using Property Llama data. Chris, Thomas, and Ryan explore trends of the current marketplace and strategies to implement.They cover: - A deep dive into cash flow by property type, with a focus on multifamily propert…
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287. Exploring Advanced 1031 Exchanges and Partnership Divisions with Matt Rappaport, Esq., LL.M.
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In this episode, Thomas and Ryan sit down with tax attorney Matthew Rappaport to dive into some of the most sophisticated tax strategies available to real estate investors.Here’s what they cover:- Partnership divisions and how they can offer a strategic advantage in 1031 exchanges.- The nuances of combining Section 121 and 1031 exchanges for optima…
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286. How the Trump & Harris Tax Plans Could Impact Real Estate Investors
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In this episode, Thomas and Ryan review the proposed tax plans of current presidential candidates and how these changes might impact real estate investors. Here’s what they cover:- Biden and Kamala Harris’s proposed tax increases and credits for affordable housing.- Trump's proposed tax cuts and extensions of existing tax laws.- Common themes of hi…
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285. Inflation & The Special Loss Allowance: Should It Be Indexed?
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In this episode, Thomas & Ryan are joined by Justin Shore, EA to dive into the impacts of indexing certain tax deductions for inflation. They cover: - The 25K Special Loss Allowance and Its Potential Impact- The Section 121 Exclusion and Other Key Deductions & Credits- The Dark Side and Bright Side of Indexing for InflationIf you're interested in t…
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284. The Triple Tax Benefits of Paying Your Children
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In this episode, Thomas & Ryan review the triple tax benefits of paying your children to work in your business and explain how to accomplish this.Not only will you reap the tax benefits, but your children will learn the value of hard work and build their resume.This is an incredibly tax-efficient strategy within an episode you won't want to miss.To…
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283. How Doctors and Professionals Buy Back Time with Real Estate Investing
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In this episode, Thomas & Ryan are joined by Dr Jeff Anzalone, the Debt-Free Doctor, to discuss how doctors and professionals can achieve financial freedom and buy back their time by investing in real estate.They cover:- Jeff's journey from a full-time dentist to achieving financial freedom through real estate investing.- What types of investments …
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282. Rinse & Repeat: Investing in Car Washes and Paying Zero Tax with Kriss Berg
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In this episode, Thomas and Ryan sit down with Kriss Berg, a seasoned entrepreneur and car wash investment guru, to delve into the lucrative world of car wash investments. Chris shares his journey from e-commerce to car washes, revealing why he chose this unique industry and how it offers significant tax benefits.Here’s what to expect:- Why Invest …
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281. How to Navigate the Short-Term Rental Loophole with Partners & Other FAQ
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In this episode, Ryan and Thomas answer the frequently asked questions about the short-term rental loophole, a popular strategy among real estate investors. They address common queries from Tax Smart insiders and clients about how to effectively use this strategy and avoid potential pitfalls.They cover: - Can you use the STR loophole if you take a …
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