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 Podcast371. Why Your Tenants Leave (And How to Fix It Fast) with Ryan Barone
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa sit down with Ryan Barone, co-founder and CEO of RentRedi, to break down how real…
Tax Smart Real Estate Investors PodcastMLRE: How He Built a $1B Multifamily Portfolio (Without Third-Party Managers) with Rob Beardsley
In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa sit down with Rob Beardsley, founder and CEO of LSCRE, to break down…
Tax Smart Real Estate Investors Podcast370. Two Major Housing Changes Investors Need to Know: Senate Housing Bill + FinCEN Reporting
Two major housing developments just hit real estate investors in a short window, and both could have a big impact on how you buy, hold, and scale residential…
Tax Smart Real Estate Investors PodcastMLRE: Flying Private: What Syndicators Should Know About Deducting a Jet
In this episode, Nate and Tom break down the truth behind private jet tax write-offs: what works, what doesn’t, and where investors get into trouble. They…
Tax Smart Real Estate Investors Podcast369. 5 Non-Negotiables for Airbnbs in 2026 with Taylor Jones
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa sit down with Taylor Jones of STR Search to break down the top five non-negotiables…
Tax Smart Real Estate Investors PodcastMLRE: K-1 Season Explained: Depreciation, Capital Accounts, and Passive Losses
K-1 season can be confusing for real estate investors, especially when depreciation, passive losses, and capital accounts start showing up on your tax…
Tax Smart Real Estate Investors Podcast368. Does Buy, Borrow, Die Still Work? Breaking Down Robuilt’s Strategy
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa react to Robuilt’s video on the buy, borrow, die strategy and the short-term rental…
Tax Smart Real Estate Investors PodcastMLRE: How to Survive the 2026 Real Estate Cycle: AI & Capital Raising Strategies
In this episode of the Major League Real Estate Podcast, we sit down with Victor Menasce, tech executive turned real estate developer, host of the Real Estate…
Tax Smart Real Estate Investors Podcast367. The Short-Term Rental ‘Loophole’ That Didn’t Work for This $25M Business
In this episode, we break down a real-life tax scenario from a $25M dealership owner who’s trying to reduce a massive annual tax bill. Here’s the situation: -…
Tax Smart Real Estate Investors PodcastMLRE: The Syndication Mistakes I'd Never Make Again (An Investor Deep Dive)
In this episode of the Major League Real Estate Podcast, Thomas Castelli shares the full story of his journey, from attending local RIAs and investing as an…
Tax Smart Real Estate Investors Podcast366. AI vs. The IRS: What Every Investor Must Learn from This Tax Court Case
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa dive into a recent Tax Court case that’s turning heads in the tax community. They…
Tax Smart Real Estate Investors Podcast365. Can You Really Write Off a Private Jet? What Actually Works with Preston Holland
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa sit down with Preston Holland, President and Founder of Prestige Aircraft…
Tax Smart Real Estate Investors Podcast364. The Tax Questions High-Income Real Estate Investors Are Asking in 2026
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa answer the most pressing questions from real estate investors and high-income…
Tax Smart Real Estate Investors Podcast363. Tax Filing Mistakes That Cost Real Estate Investors Thousands
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down the most common - and most expensive - real estate tax filing mistakes…
Tax Smart Real Estate Investors Podcast362. The Quiet Strategies High-Income Investors Use Instead of REPS or STRs
In this episode of the Tax Smart REI Podcast, Thomas Castelli breaks down how high-income earners can legally build tax-advantaged, tax-free income through…
Tax Smart Real Estate Investors Podcast361. You Don’t Need 10 Units: What One STR Can Actually Do for Your Taxes with Jason Smith
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Alex Savage are joined by Hall CPA client, Jason Smith, to discuss a real first-year…
Tax Smart Real Estate Investors Podcast360. Why Short-Term Rentals Are Still the #1 Tax Strategy for 2026 ( + New Tax Court Case)
In this episode of the Tax Smart REI Podcast, Thomas Castelli discusses the #1 tax strategy for 2026, plus a new tax court case involving the real estate…
Tax Smart Real Estate Investors Podcast359. 2026 Tax Strategies You Can’t Ignore (And What You Can Still Do for 2025)
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa discuss the top 2026 tax strategies and what moves you can still make for 2025…
Tax Smart Real Estate Investors Podcast358. 2025 Tax Strategy Buzzer Beaters & Last Minute Q&A
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa discuss last minute 2025 tax strategies and questions we receive from Tax Smart…
Tax Smart Real Estate Investors Podcast357. Cost Segregation Done Right - How In-Person Engineering Maximizes ROI with Edward Griffith
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa sit down with cost segregation expert Edward Griffith to break down what…
Tax Smart Real Estate Investors Podcast356. The Missing Step in Cost Segregation Putting Real Estate Investors at Audit Risk
In this episode of the Tax Smart REI Podcast, Thomas Castelli, Nathan Sosa, and Justin Shore unpack what’s really happening inside today’s IRS cost segregation…
Tax Smart Real Estate Investors Podcast355. Tax Strategies No One’s Talking About (That Save Real Estate Investors a Fortune)
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down under-the-radar tax strategies real estate investors and high earners…
Tax Smart Real Estate Investors Podcast354. Can Property Management Kill Your STR Loophole? (And Other Costly Mistakes)
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa field real questions from the Tax Smart Investors Facebook group, their online…
Tax Smart Real Estate Investors Podcast353. The Mega Backdoor Roth 401(k): What High-Income Earners Should Know with Alex Savage
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa, Head of the National Tax Department at Hall CPA, sit down with Alex Savage, CPA…
Tax Smart Real Estate Investors Podcast352. Solar Tax Credits for Real Estate Investors: What's Legit (And What's Not) With Nathan Sosa
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa, Head of the National Tax Department at Hall CPA, dive deep into solar tax…
Tax Smart Real Estate Investors Podcast351. Year-End Tax Planning 2025: What Every Investor Should Be Doing Now with Justin Shore, EA
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Justin Shore discuss essential year-end tax strategies for real estate investors looking to…
Tax Smart Real Estate Investors Podcast350. What Every Syndicator Gets Wrong About Taxes, Funds, and Their CPA with MLRE
In this episode of the Tax Smart REI Podcast, Thomas Castelli sits down with Matt Hamilton and Nathan Sosa, co-hosts of the Major League Real Estate Podcast…
Tax Smart Real Estate Investors Podcast349. How to Scale, Profit, and Survive in Today’s STR Market with Thanks for Visiting
In this episode of the Tax Smart REI Podcast, Thomas Castelli sits down with Annette Grant and Sarah Karakaian, co-founders of Thanks for Visiting, to reveal…
Tax Smart Real Estate Investors Podcast348. How to Turn ANY Airbnb into a Money Machine with Taylor Jones
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with short-term rental expert Taylor Jones to break down how investors are transforming…
Tax Smart Real Estate Investors Podcast347. W-2 Tax Strategies in 2025: What's Actually Working
In this episode of the Tax Smart REI Podcast, hosts Thomas Castelli and Ryan Carriere dive into one of the most-requested topics from high-income investors and…
Tax Smart Real Estate Investors Podcast346. From Cockpit to Capital: Tax Strategies High W-2 Earners Need to Know with Tait Duryea
From the cockpit to commercial real estate, Tait's story shows how a high-earning W-2 professional can build wealth outside of the stock market. In this…
Tax Smart Real Estate Investors Podcast345. Estate Planning for Real Estate Investors (Trusts vs. Wills) with Attorney Diana Khan
Estate planning is one of the most overlooked parts of real estate investing, but without it, your portfolio and family can be left exposed. This week on the…
Tax Smart Real Estate Investors Podcast344. Is a Condo or Single-Family Home Better for Maximizing Bonus Depreciation? (And More FAQ)
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, answer real investor questions from the investing community, tackling…
Tax Smart Real Estate Investors Podcast343. 100% Bonus Is Back: Is Now the Time for a Short-Term Rental?
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, break down the two most common questions investors are asking after the…
Tax Smart Real Estate Investors Podcast342. This Mistake Could Sink You in an IRS Audit with Justin Shore, EA
In this episode of the Tax Smart REI Podcast, Thomas Castelli sits down with Hall CPA Advisory Manager Justin Shore to break down why bookkeeping isn’t just…
Tax Smart Real Estate Investors Podcast341. From One Rental to $943K in Depreciation and Almost Zero Taxes with Zack Mattos
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with financial planner and short-term rental investor Zack Mattos to unpack how he went…
Tax Smart Real Estate Investors Podcast340. From Chickens to Cashflow: Inside a $3.5M Lending Portfolio and 100+ Door Empire
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with entrepreneur and investor John Paul Houston to unpack his journey from running a…
Tax Smart Real Estate Investors Podcast339. Multiple Businesses, Major Write-Offs: Marty Geier’s Path to a $40K Taxable Income
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with entrepreneur and investor Marty Geier to unpack how he reduced his taxable income…
Tax Smart Real Estate Investors Podcast338. The Truth About Infinite Banking: What You’re Not Being Told with Alex Savage CPA, CFP
Before you commit to a whole life insurance policy, you need to understand what it really is and what it isn’t. This week on the Tax Smart REI Podcast, we sit…
Tax Smart Real Estate Investors Podcast337. Cost Segregation, REPS, and the $280K Wake-Up Call with Lauren Kraus
Before you hire just any tax pro, you need to understand what a real estate-focused advisor can actually do for you. This week on the Tax Smart REI Podcast, we…
Tax Smart Real Estate Investors Podcast336. The One Big Beautiful Bill Is Law: What You Need to Know Now
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down everything real estate investors and business owners need to…
Tax Smart Real Estate Investors Podcast335. Syndication Legal 101: What Every First-Time Sponsor Must Know with Tilden Moschetti
Before you syndicate your first deal, you need to get your legal foundation right. This week on the Tax Smart REI Podcast, we sit down with Tilden Moschetti…
Tax Smart Real Estate Investors Podcast334. Grouping Elections: Why Your STR Doesn’t Belong with Your LTRs
In this week’s episode of the Tax Smart REI Podcast, Thomas and Ryan answer real estate tax questions submitted by the community. From LLC structuring and…
Tax Smart Real Estate Investors Podcast333. The Senate’s version: Permanent 100% Bonus Depreciation
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, break down the Senate’s draft tax bill and what it could mean for…
Tax Smart Real Estate Investors Podcast332. Can AI Replace Your Tax Advisor?
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, put ChatGPT to the test to answer a question that’s on the minds…
Tax Smart Real Estate Investors Podcast331. The Overlooked Tax Move that Could Save You Tens of Thousands
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, dive deep into Partial Asset Dispositions (PADs), a powerful but…
Tax Smart Real Estate Investors Podcast330. What Your CPA Isn't Telling You (And It's Costing You Thousands) with Justin Shore
In this episode of the Tax Smart REI Podcast, Thomas, Justin, and Ryan break down the most common (and costly) mistakes we see from other CPAs and the massive…
Tax Smart Real Estate Investors Podcast329. What Really Happens During an IRS Audit (and How to Win One) with Troy Silfies, CPA
In this episode of the Tax Smart REI Podcast, Thomas, Troy, and Ryan unpack real IRS audit case studies involving real estate investors and break down exactly…
Tax Smart Real Estate Investors Podcast328. Inside the “One Big, Beautiful Bill” & How To Prepare for it with Nathan Sosa, CPA, MST
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down what real estate investors need to know about the draft of the…
Tax Smart Real Estate Investors Podcast327. 2025 Tax Bill Preview: Bonus Depreciation, SALT Cap Changes, and Investor Q&A
In this week’s episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere break down what real estate investors need to know about the upcoming…
Tax Smart Real Estate Investors Podcast326. What to Do Now that Tax Day is Over + Answering Your Pressing Questions
In this post 4/15 recap, Thomas and Ryan reflect on the key themes and expert interviews from the year so far, from tiny homes to creative finance, and…
Tax Smart Real Estate Investors Podcast325. Why Now Might Be Multifamily’s Biggest Opportunity Yet with Michael Blank
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with multifamily syndication expert Michael Blank to unpack why 2025 may be one of the…
Tax Smart Real Estate Investors Podcast324. Which Boring Strategy Still Wins in 2025? With Henry Washington
In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with seasoned real estate investor and author Henry Washington to discuss why he’s not…
Tax Smart Real Estate Investors Podcast323. 2025 Market Volatility: What Real Estate Investors Need to Know with Connor Low
In this episode of the Tax Smart REI Podcast, Thomas and Ryan talk with wealth manager Connor Low, founder of Iarann Wealth, about how today’s economic…
Tax Smart Real Estate Investors Podcast322. Real Estate Investor Case Studies: How One Client Saved $285K in One Year
In this episode, Thomas and Ryan share real-life case studies from real estate investors who used strategic tax planning to save thousands, sometimes hundreds…
Tax Smart Real Estate Investors Podcast321. Does Travel Time Count Toward Material Participation?
In this Q&A episode, Ryan and Thomas answer real estate investors’ most pressing tax questions. From short-term rental loopholes to QBI deductions, they break…
Tax Smart Real Estate Investors Podcast320. How Creative Financing Helps RE Investors Succeed in Every Market Cycle w/ Chris Prefontaine
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere are joined by Chris Prefontaine, real estate veteran, founder of Smart Real…
Tax Smart Real Estate Investors Podcast319. 3 Tax Scams to Watch Out for in 2025 (And 2 Risky Strategies to Avoid)
In this episode, Thomas and Ryan break down some of the most common tax scams and questionable strategies being promoted to real estate investors—and how to…
Tax Smart Real Estate Investors Podcast318. How to 2-3X Rental Income From Midterm Rentals with Jesse Vasquez
In this episode of the Tax Smart REI Podcast, Thomas and Justin talk with midterm rental expert Jesse Vasquez, founder of AirVenture Academy, about how he…
Tax Smart Real Estate Investors Podcast317. Crush Break-Even: Pricing and Occupancy Hacks for your STR with Avery Carl
In this episode of the Tax Smart REI Podcast, Thomas and Ryan talk with short-term rental investor Avery Carl, founder of the Short Term Shop and author of…