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 serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch. Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information. Enjoy! The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor

Episodes

357. Cost Segregation Done Right: How In-Person Engineering Maximizes ROI with Edward Griffith

December 8, 2025 • 24 mins
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 investors really need to know about cost segs—why engineering-driven, in-person studies deliver superior results, and how relying on cheap or software-only reports can quietly cost investors tens of thousands and increase audit risk. You’ll learn: - What a cost segregation study ac...
Mark as Played

356. The Missing Step in Cost Segregation Putting Real Estate Investors at Audit Risk

December 2, 2025 • 24 mins
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 audits - why certain studies get challenged, the patterns auditors are catching, and the hidden risks most investors never hear about. You’ll learn: - The #1 issue auditors are flagging in cost segregation studies (and why software reports get hit hardest) - Why missing ...
Mark as Played

355. Tax Strategies No One’s Talking About (That Save Real Estate Investors a Fortune)

November 26, 2025 • 35 mins
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 can use to cut their tax bills—plus the mistakes that quietly cost people thousands. You’ll learn: - How land banking works, who it fits best, and why it can be a powerful long-term tax play - The advanced “1031” strategies including reverse and improvement exchanges to de...
Mark as Played

354. Can Property Management Kill Your STR Loophole? (And Other Costly Mistakes)

November 18, 2025 • 34 mins
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 community, and recent client conversations to tackle the most common and most confusing year-end tax issues real estate investors are facing. You’ll learn: - Why you must take depreciation on your rental properties - When you’re stuck with 40% vs 100% bonus depreciation - How...
Mark as Played

353. The Mega Backdoor Roth 401(k): What High-Income Earners Should Know with Alex Savage

November 11, 2025 • 27 mins
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, CFP, to unpack the Mega Backdoor Roth 401(k), one of the most powerful yet underutilized tax strategies for high-income earners. They break down how the strategy works, who qualifies, and why it can be a game-changer for those looking to build long-term, tax-free retirement...
Mark as Played

352. Solar Tax Credits for Real Estate Investors: What's Legit (And What's Not) With Nathan Sosa

November 3, 2025 • 35 mins
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 credits: how they work, who qualifies, and whether they can truly offset your tax liability as a real estate investor. From residential installations to short-term rentals and syndicated solar investments, Thomas and Nathan unpack the real opportunities and limitations of this inc...
Mark as Played

351. Year-End Tax Planning 2025: What Every Investor Should Be Doing Now with Justin Shore, EA

October 28, 2025 • 32 mins
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 close out 2025 strong. As Q4 winds down, they walk through the most effective levers you can pull before December 31 to minimize taxes, maximize deductions, and set yourself up for a smoother filing season. From vehicle deductions and short-term rental timing to real estate p...
Mark as Played

350. What Every Syndicator Gets Wrong About Taxes, Funds, and Their CPA with MLRE

October 21, 2025 • 31 mins
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 and leaders at Hall CPA, to unpack the complex world of real estate syndications and funds and the tax traps that even seasoned operators overlook. Matt and Nathan work directly with large private equity clients and syndicators, managing tens to hundreds of millions in assets....
Mark as Played

349. How to Scale, Profit, and Survive in Today’s STR Market with Thanks for Visiting

October 14, 2025 • 36 mins
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 what it really takes to run a profitable short-term rental business in today’s market. Annette and Sarah have coached thousands of hosts on how to build scalable, hospitality-driven operations that actually make money. Together, they unpack the truth behind STR success, from ...
Mark as Played

348. How to Turn ANY Airbnb into a Money Machine with Taylor Jones

October 6, 2025 • 38 mins
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 ordinary Airbnbs into high-ROI “money machines”, even as the STR landscape becomes more competitive. Tune in to learn: - Why data-driven decisions outperform emotion-based investing every time. - How to identify high-demand markets with built-in traveler traffic and lower r...
Mark as Played

347. W-2 Tax Strategies in 2025: What's Actually Working

September 29, 2025 • 39 mins
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 professionals, W-2 tax strategies. Tune in to learn: - Why W-2 income is so highly taxed and the biggest obstacles to offsetting it - How Section 469 passive activity rules work and proven ways to navigate them with real estate professional status (REPS) or short-term rent...
Mark as Played

346. From Cockpit to Capital: Tax Strategies High W-2 Earners Need to Know with Tait Duryea

September 22, 2025 • 55 mins
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 episode of the Tax Smart REI Podcast, Tait shares the lessons he learned moving from single-family to multifamily to syndications and the strategies that help pilots and other professionals put their money to work more effectively. You'll learn: - How Tait’s early mistakes shaped...
Mark as Played

345. Estate Planning for Real Estate Investors (Trusts vs. Wills) with Attorney Diana Khan

September 15, 2025 • 31 mins
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 REI Podcast, we sit down with attorney, broker, and investor Diana Khan to talk about how real estate investors should approach estate planning. You'll learn: - Why every investor needs at least a will and power of attorney (even at 18) - The difference between wil...
Mark as Played

344. Is a Condo or Single-Family Home Better for Maximizing Bonus Depreciation? (And More FAQ)

September 9, 2025 • 27 mins
In this episode of the Tax Smart REI Podcast, Thomas Castelli and Ryan Carriere, CPA, answer real investor questions from the investing community, tackling some of the most pressing topics around bonus depreciation, short-term rentals, and advanced tax planning. Tune in to learn: - How cost segregation results differ between condos, single-family homes, and properties with big-ticket land improvements like pools - Why new renovat...
Mark as Played

343. 100% Bonus Is Back: Is Now the Time for a Short-Term Rental?

September 2, 2025 • 39 mins
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 passage of the “Big Beautiful Bill” and the return of 100% bonus depreciation: - Should you invest in real estate or specifically short-term rentals for tax savings? - When does it make sense to start working with a tax strategist? Tune in to learn: - Why existing landlords...
Mark as Played

342. This Mistake Could Sink You in an IRS Audit with Justin Shore, EA

August 26, 2025 • 39 mins
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 busy work, it’s the foundation of audit defense and financial success as a real estate investor. Tune in to learn: - Why sloppy bookkeeping can raise red flags and trigger IRS scrutiny - The key differences between Schedule E and Schedule C—and why they matter for your rental...
Mark as Played

341. From One Rental to $943K in Depreciation and Almost Zero Taxes with Zack Mattos

August 19, 2025 • 38 mins
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 from a 20-year career focused solely on traditional retirement accounts to leveraging real estate to nearly eliminate his tax bill, including a staggering $943K in depreciation from one luxury rental property. Tune in to learn: - How he turned his Austin dream home into a h...
Mark as Played

340. From Chickens to Cashflow: Inside a $3.5M Lending Portfolio and 100+ Door Empire

August 12, 2025 • 37 mins
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 backyard chicken operation to building a $3.5M private lending portfolio and a 100+ door real estate empire — all while dramatically reducing his tax bill by qualifying as a Real Estate Professional. Tune in to learn: - How John went from semi-retirement to scaling multiple i...
Mark as Played

339. Multiple Businesses, Major Write-Offs: Marty Geier’s Path to a $40K Taxable Income

August 5, 2025 • 49 mins
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 from $1.4 million to just $40K using a blend of business building, short-term rentals, and advanced tax strategy. Tune in to learn: - How Marty uses the 500-hour rule to make short-term rental losses non-passive and deductible - Why he starts a new business each year and how...
Mark as Played

338. The Truth About Infinite Banking: What You’re Not Being Told with Alex Savage CPA, CFP

July 29, 2025 • 46 mins
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 down with financial planner Alex Savage, CPA and CFP, to break down the infinite banking concept and whether it truly makes sense for real estate investors and high-income earners. You'll learn: - What whole life insurance and infinite banking actually are (beyond the sales...
Mark as Played

Popular Podcasts

    Stuff You Should Know

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    My Favorite Murder with Karen Kilgariff and Georgia Hardstark

    My Favorite Murder with Karen Kilgariff and Georgia Hardstark

    My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.

    Dateline NBC

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    The Breakfast Club

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

    The Joe Rogan Experience

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

Explore

iHeart

Live Radio

Podcasts

Artist Radio

Exclusives

News

Features

Events

Contests

Photos

Information

About

Advertise

Blog

Brand Guidelines

Contest Guidelines

Subscription Offers

Jobs

Get the App

Automotive

Home

Mobile

Wearables

© 2025 iHeartMedia, Inc.