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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353. The Mega Backdoor Roth 401(k): What High-Income Earners Should Know with Alex Savage
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27:33In 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…
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352. Solar Tax Credits for Real Estate Investors: What's Legit (And What's Not) With Nathan Sosa
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35:55In 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 inves…
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351. Year-End Tax Planning 2025: What Every Investor Should Be Doing Now with Justin Shore, EA
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32:50In 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 …
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350. What Every Syndicator Gets Wrong About Taxes, Funds, and Their CPA with MLRE
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31:36In 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 priva…
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349. How to Scale, Profit, and Survive in Today’s STR Market with Thanks for Visiting
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36:43In 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 …
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348. How to Turn ANY Airbnb into a Money Machine with Taylor Jones
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38:16In 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.…
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347. W-2 Tax Strategies in 2025: What's Actually Working
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39:08In 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…
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346. From Cockpit to Capital: Tax Strategies High W-2 Earners Need to Know with Tait Duryea
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55:42From 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 the…
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345. Estate Planning for Real Estate Investors (Trusts vs. Wills) with Attorney Diana Khan
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31:30Estate 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 need…
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344. Is a Condo or Single-Family Home Better for Maximizing Bonus Depreciation? (And More FAQ)
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27:51In 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 hom…
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343. 100% Bonus Is Back: Is Now the Time for a Short-Term Rental?
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39:26In 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…
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342. This Mistake Could Sink You in an IRS Audit with Justin Shore, EA
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39:01In 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 d…
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341. From One Rental to $943K in Depreciation and Almost Zero Taxes with Zack Mattos
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38:34In 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 luxur…
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340. From Chickens to Cashflow: Inside a $3.5M Lending Portfolio and 100+ Door Empire
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37:52In 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 Profess…
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339. Multiple Businesses, Major Write-Offs: Marty Geier’s Path to a $40K Taxable Income
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49:50In 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 l…
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338. The Truth About Infinite Banking: What You’re Not Being Told with Alex Savage CPA, CFP
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46:35Before 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 lear…
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337. Cost Segregation, REPS, and the $280K Wake-Up Call with Lauren Kraus
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34:07Before 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 sit down with investor and developer Lauren Kraus to hear how working with a specialist helped her uncover over $280K in missed tax savings—and dramatically shift her investing strategy.You'…
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336. The One Big Beautiful Bill Is Law: What You Need to Know Now
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38:45In 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 know about the now-official “Big Beautiful Bill”, the sweeping tax package that just became law.Key topics covered:- 100% bonus depreciation is back and permanent: who qualifies and when it sta…
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335. Syndication Legal 101: What Every First-Time Sponsor Must Know with Tilden Moschetti
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35:21Before 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, real estate attorney and experienced syndicator, to talk through the legal must-haves for your first capital raise. You'll learn:- When a deal becomes a syndication in the eyes of the SEC- The…
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334. Grouping Elections: Why Your STR Doesn’t Belong with Your LTRs
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18:44In 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 grouping elections to retroactive cost segregation and solo 401(k) eligibility, this Q&A session covers some of the most common (and confusing) issues investors face midyear.Key topics covered:- …
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333. The Senate’s version: Permanent 100% Bonus Depreciation
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30:25In 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 real estate investors if it becomes law.Key topics covered:- 100% bonus depreciation made permanent: what this really means- Major changes to Qualified Opportunity Zones (QOZs)- Updates to Se…
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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 of many real estate investors: Can AI actually replace your tax advisor?Key topics covered:- Where AI like ChatGPT performs well and where it fails- Real-time testing of ChatGPT on short-term …
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331. The Overlooked Tax Move that Could Save You Tens of Thousands
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18:53In 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 often overlooked tax strategy that can unlock substantial savings for real estate investors during renovations.Key topics covered:- What a partial asset disposition (PAD) is and how it works- …
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330. What Your CPA Isn't Telling You (And It's Costing You Thousands) with Justin Shore
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42:34In 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 savings real estate investors are missing because of them.Tune in to learn:- Why electing out of bonus depreciation without knowing it can cost you tens of thousands- How improperly class…
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329. What Really Happens During an IRS Audit (and How to Win One) with Troy Silfies, CPA
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44:00In 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 what happened, how they responded, and how they won.Tune in to learn:- What triggers IRS audits for short-term rentals and REPS (and how to avoid them)- The one thing most CPAs get wrong when…
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