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 Podcast316. Tiny Homes, Huge Returns: How Rob Abasolo Built a Winning STR Portfolio
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with short-term rental investor Rob Abasolo—the mind behind the “Robuilt” YouTube…
Tax Smart Real Estate Investors Podcast315. The Future of Bonus Depreciation and SALT: 2025 Tax Updates with Nathan Sosa, CPA, MST
In this episode, Thomas and Nathan Sosa take a deep dive into the potential 2025 tax changes that could reshape the landscape for real estate investors. They…
Tax Smart Real Estate Investors Podcast314. Depreciation 101: How to Use It the Right Way to Save Thousands in Taxes
In this episode, Ryan and Thomas take a deep dive into depreciation, one of the most powerful tax-saving tools available to real estate investors. They break…
Tax Smart Real Estate Investors Podcast312. From Wall Street to Short-Term Rentals: How to Build a 38-Property Empire with Michael Chang
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with short-term rental investor Michael Chang to discuss how he went from Wall Street…
Tax Smart Real Estate Investors Podcast313. Do I Need To Do A Cost Segregation Study?
In our first monthly Q&A episode, Ryan and Thomas answer the most pressing tax questions from listeners. They tackle a variety of hot-button topics, including…
Tax Smart Real Estate Investors Podcast311. LLC Myth-Busters: Is Your Real Estate Really Protected?
In this episode, Ryan and Thomas pull back the curtain on LLCs, busting the biggest myths that trip up real estate investors—and revealing how to truly protect…
Tax Smart Real Estate Investors Podcast310. 2025 Real Estate Market Outlook with Dave Meyer from BiggerPockets
In this episode of the TaxSmart REI Podcast, Thomas and Ryan sit down with Dave Meyer, Head of Real Estate Investing at BiggerPockets, to discuss the 2025 real…
Tax Smart Real Estate Investors Podcast309. What’s the 20% Rule and How Can It Make Your STR Profitable? with John Bianchi
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with John Bianchi, founder of STR Search and an expert in short-term rental data and…
Tax Smart Real Estate Investors Podcast308. How to Leverage Insurance and Investments for Real Estate Growth with Austin Dean
In this episode of the Tax Smart REI Podcast, Thomas, Ryan, and Justin sit down with Austin Dean, a financial planner at Waystone Advisors specializing in real…
Tax Smart Real Estate Investors Podcast307. 7 Overlooked Real Estate Deductions That Could Save You Thousands
In this episode, Ryan and Alex break down the top overlooked deductions real estate investors often miss—and how to ensure you’re capturing them all. This…
Tax Smart Real Estate Investors Podcast306. Can You Pull Off REPS in 2025 (And Save BIG)?
In this episode, Thomas and Ryan break down the essentials of real estate professional status (REPS) and how to qualify this year. This episode explores: -…
Tax Smart Real Estate Investors Podcast305. Passive or Non-Passive: What’s New for Short-Term Rentals in 2025
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…
Tax Smart Real Estate Investors Podcast304. 2025 Tax Changes & The Corporate Transparency Act Update
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…
Tax Smart Real Estate Investors Podcast303. From Rookie to Mogul: How to Build Rental Real Estate Riches with Travis & Regan Perry
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…
Tax Smart Real Estate Investors Podcast302. Short-Term Rental Financing: Taxes, Loans, and Winning Strategies with Stacey Dowling
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…
Tax Smart Real Estate Investors Podcast301. Why the Wealthy Invest differently: Timing, Trends, and Tax Benefits with Ben Fraser
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…
Tax Smart Real Estate Investors Podcast300. The 14-Day Rule & Personal Use Days: Avoiding Common Pitfalls for STR Owners
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…
Tax Smart Real Estate Investors Podcast299. Corporate Transparency Act Checklist: Avoid Costly Mistakes with FinCEN Filing Agents
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…
Tax Smart Real Estate Investors Podcast298. From Schedule E to Cost Segregation: Tackling Taxes with an Expert Q&A
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…
Tax Smart Real Estate Investors Podcast297. Drilling Into Profits: A Case Study on Oil & Gas Working Interests with Troy Eckard
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…
Tax Smart Real Estate Investors Podcast296. Top Year-End Tax Strategies: Maximize Deductions Before December 31st
In this episode, Thomas and Ryan break down year-end tax strategies tailored for real estate investors, providing valuable insights for maximizing tax savings…
Tax Smart Real Estate Investors Podcast295. The Future of Housing: How Interest Rates and Labor Shape Real Estate with Logan Mohtashami
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…
Tax Smart Real Estate Investors Podcast294. IRS Red Flags: Why Foradis Failed to Prove REPS with Nathan Sosa, CPA
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…
Tax Smart Real Estate Investors Podcast293. Unpacking EACH Real Estate Investment Strategy: Pros, Cons, and Tax Benefits
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…
Tax Smart Real Estate Investors Podcast292. Generate Massive Cash Flow By Investing in Senior Living with Isabelle Guarino
In this episode of the Tax Smart REI Podcast, Thomas is joined by Isabelle Guarino to discuss investing in residential assisted living facilities. Isabelle…
Tax Smart Real Estate Investors Podcast291. The Power of Section 179 for Commercial Real Estate and Short-Term Rentals w/ Nathan Sosa, CPA
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…
Tax Smart Real Estate Investors Podcast290. How to use Equity Losses to Offset Real Estate Capital Gains with Nathan Cook
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…
Tax Smart Real Estate Investors Podcast289. Cutting Out the Middleman: How to Go Direct to Sellers and Boost Your Profits with Scott Morse
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…
Tax Smart Real Estate Investors Podcast288. Analyzing 7,000 Properties: How To Maximize Cash flow Today with Chris Lopez
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…
Tax Smart Real Estate Investors Podcast287. Exploring Advanced 1031 Exchanges and Partnership Divisions with Matt Rappaport, Esq., LL.M.
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…
Tax Smart Real Estate Investors Podcast286. How the Trump & Harris Tax Plans Could Impact Real Estate Investors
In this episode, Thomas and Ryan review the proposed tax plans of current presidential candidates and how these changes might impact real estate investors…
Tax Smart Real Estate Investors Podcast285. Inflation & The Special Loss Allowance: Should It Be Indexed?
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…
Tax Smart Real Estate Investors Podcast284. The Triple Tax Benefits of Paying Your Children
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…
Tax Smart Real Estate Investors Podcast283. How Doctors and Professionals Buy Back Time with Real Estate Investing
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…
Tax Smart Real Estate Investors Podcast282. Rinse & Repeat: Investing in Car Washes and Paying Zero Tax with Kriss Berg
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…
Tax Smart Real Estate Investors Podcast281. How to Navigate the Short-Term Rental Loophole with Partners & Other FAQ
In this episode, Ryan and Thomas answer the frequently asked questions about the short-term rental loophole, a popular strategy among real estate investors…
Tax Smart Real Estate Investors Podcast280. The Zero-Tax Goal: Is It Wise To Eliminate Your Taxes Completely?
In this episode, Ryan and Thomas answer the frequently asked question, “Should I reduce my taxes to zero?”. Answering this question starts with understanding…
Tax Smart Real Estate Investors Podcast279. Leveraging BRRRR for Optimal Wealth Growth & Tax Efficiency
In this episode, Ryan and Thomas dive into the BRRRR strategy—Buy, Renovate, Rent, Refinance, Repeat. They discuss how this approach serves as a formidable…
Tax Smart Real Estate Investors Podcast278. The STR Loophole Audit Playbook: Protecting Your Profits & Countering Claims
The ever-popular STR Loophole has been used by countless investors and helped them save tens if not hundreds of thousands of dollars in taxes. In this episode…
Tax Smart Real Estate Investors Podcast277. Growing A Multi-Million Dollar Empire & Real Estate's Role with Sam Parr
In this week's episode, Ryan and Brandon are joined by Sam Parr, a serial entrepreneur who has built and sold several multimillion-dollar companies, to discuss…
Tax Smart Real Estate Investors Podcast276. Dealer Status and the IRS: What Real Estate Investors Need to Know
In this episode, Ryan is joined by Nathan Sosa, CPA to discuss what it means to have dealer status when selling a property. They cover: - Dealer Status…
Tax Smart Real Estate Investors Podcast275. The Revolutionary World of Oil & Gas Investing with Troy Eckard
In this episode, Brandon jumps in as guest host and welcomes Troy Eckard back to the Tax Smart REI podcast to dive deeper into the world of oil & gas…
Tax Smart Real Estate Investors Podcast274. Exploring the Power of Opportunity Zones: A Deep Dive with Barrett Linburg
In this week's episode, Ryan and Justin Shore, EA are joined by Barrett Linburg as he reveals the transformative potential of investing in Opportunity Zones…
Tax Smart Real Estate Investors Podcast273. The Great ROE Debate in Real Estate Investing with Chris Lopez
In this week's episode, Brandon is joined by real estate entrepreneur and investor, Chris Lopez, to explore the heavily debated topic of ROE. They cover: - An…
Tax Smart Real Estate Investors Podcast272. Home Advantage: Mastering Tax Deductions Through House Hacking
In this week's episode, Ryan is joined by Tax Advisor, Alex Savage, to break down the best practices of house hacking. They cover: - Common Misconceptions…
Tax Smart Real Estate Investors Podcast271. IRS Secrets: How Safe Harbors & BAR Tests Maximize Tax Savings & Boost Real Estate Profits
In this episode, Ryan and Thomas break down the tax treatment of repairs & maintenance expenses vs. capital improvements and how to maximize tax savings…
Tax Smart Real Estate Investors Podcast270. How Investing in Real Estate Reduces Your Effective Tax Rate — Even Without REPS or STRs
In this episode, Ryan and Thomas explain how simply investing in rental real estate reduces your effective tax rate and puts you in a favorable position even…
Tax Smart Real Estate Investors Podcast269. The Cold Hard Truth About LLCs for Real Estate Investors with Ron Rohde, Esq.
In this episode, Ryan and Thomas are joined by Ron Rohde, Esq, to discuss what real estate investors really need to know about LLCs, including: - What are…
Tax Smart Real Estate Investors Podcast268. How To Turn Rental Losses Non-Passive Without Material Participation with Justin Shore, EA
In this episode, Ryan and Thomas are joined by tax expert Justin Shore, EA, to discuss how you can turn losses non-passive without material participation or…
Tax Smart Real Estate Investors Podcast267. The Essential Do's & Don'ts of S-Corps for Real Estate Investors with Nathan Sosa, CPA
In this episode, Ryan and Thomas are joined by tax expert Nathan Sosa, CPA to discuss: - What are S-Corps? - Why you shouldn't put rentals in S-Corps - When…
Tax Smart Real Estate Investors Podcast266. 7 Exit Strategies To Destroy Capital Gains Taxes When You Sell Your Next Property
In this episode, Ryan and Thomas discuss 7 exit strategies to minimize the tax hit when you sell your next property: - The 1031 Exchange - The “Lazy 1031…
Tax Smart Real Estate Investors Podcast265. Breaking Down The Tax Benefits of Oil & Gas Investments for Real Estate Investors
In this episode, Ryan and Thomas discuss: - The Tax Implications for Oil & Gas Investments: Ryan and Thomas delve into the tax nuances of oil and gas working…
Tax Smart Real Estate Investors Podcast264. The Secrets to Investing in Parking Lots & Mobile Home Parks with Kevin Bupp
In this episode, Ryan and Thomas are joined by Kevin Bupp, an experienced commercial real estate investor, podcast host, and best-selling author of “The…
Tax Smart Real Estate Investors Podcast263. Navigating Loans: Depreciation Add Backs, Due-On-Sale, Sub-To, & Interest Rates
In this episode, Ryan and Thomas are joined by Kenny Simpson, an independent residential mortgage broker and podcast host, to discuss: - Key Elements Lenders…
Tax Smart Real Estate Investors Podcast262. A Deep Dive Into Investing In Oil & Gas for Real Estate Investors with Troy Eckard
In this episode, Ryan and Thomas are joined again by Troy Eckard from Eckard Enterprises for a deep dive into investing in oil & gas. In this episode, we…
Tax Smart Real Estate Investors Podcast261. Can Real Estate Investors & Influencers Deduct Rolexes and Lamborghinis?
Join Ryan and Thomas as they demystify common myths and misconceptions about deducting luxury items, including: - Can investors & influencers write off Rolexes…
Tax Smart Real Estate Investors Podcast260. Tax Structuring Considerations for Transferring Real Estate Wealth to the Next Generation
In this episode, Ryan and Thomas welcome Tim Wallen, CPA and CEO, along with Rick Reuter, CPA, CGMA, and Controller of MLG Capital, for a deep dive into: -…
Tax Smart Real Estate Investors Podcast259. Why Invest in Boutique Hotels Instead of STRs & The Power of Personal Branding with Rich Somers
In this week's episode, Ryan and Thomas are joined by Rich Somers, an active real estate investor and entrepreneur with a portfolio valued at $70M+, to…
Tax Smart Real Estate Investors Podcast258. 2024 REI Forecast: Key Trends You Can't Afford to Miss & Why Start with Strategy w/ Dave Meyer
In this episode, Ryan and Thomas are joined by the host of BiggerPocket's On The Market Podcast, real estate investor, and best-selling author, Dave Meyer, to…
Tax Smart Real Estate Investors Podcast257. How To Thrive in the 2024 Multifamily Investing Market & Tax Tips with Gino Barbaro
In this episode, Thomas & Ryan are joined by Gino Barbaro, multifamily investor, business owner, author and entrepreneur, to discuss: - How Gino's team avoided…