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 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 starts - QBI updates: simplified rules, new thresholds, and small business wins - SALT cap expansion (finally!) and what the five-year phase-in means f...
Jul 16, 2025•39 min
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, 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 two-entity structure every sponsor should use - What PPMs, subscription agreements, and operating agreements actually do - Why you shouldn’t rely o...
Jul 07, 2025•35 min
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 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: - Can I move my STR into an LLC if the deed and mortgage are in my name? - Why short-term rentals can’t be included in a Dash-9 grouping election ...
Jul 02, 2025•19 min
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 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 Section 179 and interest expensing rules - The fate of the SALT cap and why it’s still a moving target - Expanded QSBS exclusion and its impact on s...
Jun 25, 2025•30 min
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 rental strategies - Common AI mistakes on REPS, depreciation, and passive loss rules - A new listener question ChatGPT got both right and wrong - W...
Jun 18, 2025•31 min
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 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 - When and how to claim a PAD on your tax return - Using cost segregation studies to support PAD calculations - Real-life case studies, including one...
Jun 11, 2025•19 min
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 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 classifying repairs vs. improvements could trigger an audit or shrink your deductions - The overlooked grouping strategy that saved one client $150K+ in...
Jun 04, 2025•43 min
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 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 representing clients in an audit - How a $209K tax bill was reduced to $296—with documentation and strategy - Why being “audit-ready” matters more...
May 28, 2025•44 min
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 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 100% bonus depreciation (and who qualifies) - SALT cap drama: why it could derail the bill - Changes to Qualified Opportunity Zones and what they me...
May 21, 2025•37 min
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 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 changes to the SALT deduction cap - How to properly log hours for REPS (Real Estate Professional Status) - Using the STR loophole for boutique hotels - ...
May 14, 2025•30 min
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 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 on 100% bonus depreciation, and answer real investor questions from email and the Tax Smart Facebook group. Topics include: - Real estate investment ...
May 08, 2025•25 min
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 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 from losing millions to build a $300M multifamily portfolio. - What’s really driving investor hesitation—and how to overcome it. - How tariffs, inf...
May 07, 2025•37 min
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 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 mail (even in the age of AI). - How he adjusts his strategy based on market cycles—without overreacting to headlines. - Why he believes helping sell...
Apr 30, 2025•30 min
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 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 why panic is rarely a productive move, and shares how both real estate and equity investors can make smart, intentional decisions during periods of vol...
Apr 23, 2025•39 min
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 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 explores: - How one couple saved $285K in a single year using REPS and cost segregation. - Why timing matters when using the short-term rental loophole—...
Apr 16, 2025•36 min
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 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 Safe Harbor - STR Conversions Mid-Year - Bonus Depreciation Recapture - Home Improvement Records - The 14-Day Rule Explained Remember t...
Apr 11, 2025•21 min
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 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 financing deals, and navigate subject-to transactions with confidence. You'll also hear about: - Why 2008 changed the way Chris does business forever - H...
Apr 09, 2025•31 min
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 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 misrepresented and what the IRS has to say about it. - The truth behind inflated art donation deductions and the risks they carry. - Two high-risk st...
Apr 02, 2025•28 min
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 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 contracts with corporate clients, relocation companies, and healthcare providers, all without the constant turnover and management headaches of short-term r...
Mar 26, 2025•45 min
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 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 self-management, and avoiding costly pitfalls in today’s higher-rate environment. Tune in to learn: - Why buying where you’ve actually vacationed can gi...
Mar 19, 2025•36 min
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 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 tax planning. Tune in to learn: - Why tiny homes and unique spaces can command premium nightly rates. - How reinvesting in a property’s outdoor amenit...
Mar 12, 2025•44 min
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 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 discuss: - Tax Brackets & QBI: How rates could shift in 2025—and why that matters for your business income. - 100% Bonus Depreciation: Whether it might...
Mar 04, 2025•29 min
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 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, and why it matters for investors. - Cost Segregation & Bonus Depreciation – How to front-load tax savings and boost cash flow. - Depreciation Reca...
Feb 25, 2025•28 min
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 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 freedom. Tune in to learn: - How Michael transitioned from a high-pressure Wall Street career to full-time real estate investor. - The basics of rental a...
Feb 13, 2025•31 min
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 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 be performed in the first year. They discuss: - Flips & W-2 Incomes – Why these profits generally count as active, even if you’re not a real es...
Feb 12, 2025•22 min
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 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? - Pitfalls to Avoid—from the “due on sale” clause to S corp mix-ups. - And more! If you’re eager to make sure your LLC is set up the right way—or w...
Feb 07, 2025•24 min
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 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 rates and affordability will impact investors in 2025. - The state of commercial real estate, including potential opportunities in multifamily inve...
Jan 30, 2025•43 min
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 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 data to find winning deals. Tune in to learn: - How to use the “20% Rule” to evaluate short-term rental markets for cash flow. - The importance of re...
Jan 26, 2025•50 min
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 estate-focused financial planning. With over 13 years of experience, Austin offers valuable insights into creating financial independence through strategic investments tailored to real estate investors. Tune in to learn: - Why real estate is a powerful tool for building wealth and achieving financial independence. - How to use tools like ...
Jan 19, 2025•43 min
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 episode explores: - Why closing costs and loan costs should be included in your depreciable basis. - The most common insurance mistakes that leave money on the table. - The importance of taking depreciation (and what happens if you don’t). - And More! If maximizing your tax savings is one of your goals, now is the time to dig into these often-...
Jan 13, 2025•24 min
