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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332. Can AI Replace Your Tax Advisor?
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31:02
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31:02In 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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18:53
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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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42:34
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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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44:00
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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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328. Inside the “One Big, Beautiful Bill” & How To Prepare for it with Nathan Sosa, CPA, MST
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37:08In 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 2025 tax bill, dubbed the “One Big, Beautiful Bill”, including what’s in it, what might change, and how to prepare for the opportunities it presents.Key topics covered:- The likely return of …
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327. 2025 Tax Bill Preview: Bonus Depreciation, SALT Cap Changes, and Investor Q&A
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30:01In 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 2025 tax bill, including where it stands, what’s likely to be included, and how it could impact your bottom line.Key topics covered:- Expected return of 100% bonus depreciation- Potential chang…
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326. What to Do Now that Tax Day is Over + Answering Your Pressing Questions
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24:33
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24:33In 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 reinforce a common truth: smart investing still works in today’s market if you stay focused and play the long game.They also dive into what’s happening with the 2025 tax bill, including the outlook …
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325. Why Now Might Be Multifamily’s Biggest Opportunity Yet with Michael Blank
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37:09
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37:09In 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 best times in years to get started—or scale—in multifamily real estate.Tune in to learn:- Why today’s market conditions offer lower risk and higher long-term upside.- How Michael bounced back …
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324. Which Boring Strategy Still Wins in 2025? With Henry Washington
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29:34
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29:34In 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 chasing creative finance trends, and why his “boring” strategy continues to deliver results in 2025’s unpredictable market.Tune in to learn:- Why Henry sticks with off-market deals and direct …
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323. 2025 Market Volatility: What Real Estate Investors Need to Know with Connor Low
38:31
38:31
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38:31In 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 uncertainty, from global tariffs to interest rate swings, is impacting investors, and what real estate investors should be doing about it.Connor breaks down the current market landscape, explains wh…
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322. Real Estate Investor Case Studies: How One Client Saved $285K in One Year
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36:23
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36:23In this episode, Thomas and Ryan share real-life case studies from real estate investors who used strategic tax planning to save thousands, sometimes hundreds of thousands, on their tax bills. They also reveal the most common mistakes and missed opportunities they see from investors who waited too long or relied on the wrong advice.This episode exp…
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321. Does Travel Time Count Toward Material Participation?
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21:23
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21:23In 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 down some of the most misunderstood topics in real estate tax strategy and provide practical, real-world guidance.They discuss:- STR Losses & NOLs- Travel Time & Material Participation- QBI S…
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320. How Creative Financing Helps RE Investors Succeed in Every Market Cycle w/ Chris Prefontaine
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30:37
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30:37In 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 Estate Coach, and leader of the Wicked Smart Community.Chris brings over three decades of experience to the table and breaks down how to invest without banks, structure zero-interest seller fina…
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319. 3 Tax Scams to Watch Out for in 2025 (And 2 Risky Strategies to Avoid)
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27:33
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27:33In 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 avoid falling into these costly traps.This episode explores:- Why equipment leasing deals promising non-passive losses are almost always too good to be true.- How solar tax credits are being mi…
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318. How to 2-3X Rental Income From Midterm Rentals with Jesse Vasquez
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45:28
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45:28In 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 accidentally stumbled into midterm rentals and scaled his business into a highly profitable portfolio.Jesse shares the exact strategies he uses to 2-3X rental income by securing long-term contrac…
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317. Crush Break-Even: Pricing and Occupancy Hacks for your STR with Avery Carl
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35:47
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35:47In 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 Smarter Short-Term Rentals, about how she grew one cabin purchase into a portfolio of over 250 units.Avery shares the blueprint for choosing the right vacation markets, designing systems for sel…
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316. Tiny Homes, Huge Returns: How Rob Abasolo Built a Winning STR Portfolio
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43:53
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43:53In 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 channel—to discuss how he transformed his copywriting background into a thriving short-term rental empire. Rob reveals how he maximizes ROI through unique stays, eye-catching design, and strategic …
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315. The Future of Bonus Depreciation and SALT: 2025 Tax Updates with Nathan Sosa, CPA, MST
28:37
28:37
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28:37In 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 outline what may happen if the Tax Cuts and Jobs Act expires, how bonus depreciation could come back (or not), and what you need to do to prepare now so you’re not caught off-guard.They discus…
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314. Depreciation 101: How to Use It the Right Way to Save Thousands in Taxes
27:55
27:55
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27:55In 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 down how depreciation works, how to accelerate it, and strategies to minimize depreciation recapture when selling your properties.They discuss:- Depreciation 101 – What it is, how it works, an…
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312. From Wall Street to Short-Term Rentals: How to Build a 38-Property Empire with Michael Chang
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30:38
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30:38In 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 investment banker to building a 38-property short-term rental empire. Michael shares how he leveraged rental arbitrage, short-term rental tax strategies, and automation to achieve financial fre…
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313. Do I Need To Do A Cost Segregation Study?
22:01
22:01
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22:01In 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 when flipping property income is considered “active” (and why that matters if you have a W-2), how partial asset dispositions really work, and whether or not a cost segregation study has to b…
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311. LLC Myth-Busters: Is Your Real Estate Really Protected?
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23:41
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23:41In 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 your rental portfolio.They discuss:- Asset Protection vs. Tax Savings—understanding what LLCs really do (and don’t do).- The Right Structure—single-member, multi-member, or holding company?-…
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310. 2025 Real Estate Market Outlook with Dave Meyer from BiggerPockets
43:15
43:15
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43:15In 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 estate market outlook and what investors need to know.Tune in to learn:- Where we are in the current real estate market cycle and what’s next for home prices and sales volume.- How interest …
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309. What’s the 20% Rule and How Can It Make Your STR Profitable? with John Bianchi
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50:18
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50:18In 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 investment strategies.With a 100% track record in helping investors identify and acquire over 200 profitable short-term rental properties, John shares his insider knowledge on leveraging Airbnb …
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308. How to Leverage Insurance and Investments for Real Estate Growth with Austin Dean
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42:40
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42:40In 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 estate-focused financial planning. With over 13 years of experience, Austin offers valuable insights into creating financial independence through strategic investments tailored to real estat…
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