Episodes

  • 304. 2025 Tax Changes & The Corporate Transparency Act Update

    304. 2025 Tax Changes & The Corporate Transparency Act Update
    Dec 13 2024
    In this episode of the Tax Smart REI podcast, Thomas and Ryan address pivotal updates as the year draws to a close. They provide essential insights into the expected 2025 tax changes, the implications of the new administration, and the recent developments regarding the Corporate Transparency Act's enforcement status. Here's what they discuss: - The Expiration of the Tax Cuts and Jobs Act - Corporate Transparency Act Updates - Tips on Staying Proactive with Voluntary Compliance Measures - Advice for Real Estate Investors to Prepare for Year-End To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    22 mins
  • 303. From Rookie to Mogul: How to Build Rental Real Estate Riches with Travis & Regan Perry

    303. From Rookie to Mogul: How to Build Rental Real Estate Riches with Travis & Regan Perry
    Dec 6 2024
    In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with Travis and Regan Perry, real estate investors who have crafted a flourishing portfolio of short-term rental properties. With roots in Iowa, the Perrys share their journey from purchasing their first home to managing multiple properties across several states. Tune in to learn: - Steps to start investing in short-term rentals and build a substantial property portfolio. - How to leverage local events and tourism to maximize rental income. - The importance of tax strategies, including cost segregation, to enhance cash flow. - Practical tips for managing properties remotely and building a reliable team. Whether you’re a budding entrepreneur or an experienced investor, this episode is brimming with invaluable insights and inspiring stories to help you expand your real estate ventures. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Connect with Travis & Regan: https://shorttermrentaledge.com/ https://perrydisevacationrentals.com/ Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    41 mins
  • 302. Short-Term Rental Financing: Taxes, Loans, and Winning Strategies with Stacey Dowling

    302. Short-Term Rental Financing: Taxes, Loans, and Winning Strategies with Stacey Dowling
    Nov 29 2024
    In this episode of the Tax Smart REI Podcast, Thomas & Ryan sit down with Stacey Dowling, a seasoned mortgage lender specializing in short-term rental financing. Stacey brings over 30 years of experience to the table, offering actionable insights into obtaining loans for short-term rentals. Tune in to learn: - How to qualify for a short-term rental loan. - The impact of tax returns, depreciation, and cost segregation on lending decisions. - Strategies to navigate regulations and mitigate challenges from neighbors or local laws. - Creative approaches like midterm rentals to adapt to changing market dynamics. Whether you’re a seasoned investor or just getting started, this episode is packed with expert advice and real-world examples to help you achieve your real estate goals. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Connect with Stacey Dowling: Email: sdowling@dg-lending.com Visit PURE at: www.rentpure.com Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    35 mins
  • 301. Why the Wealthy Invest differently: Timing, Trends, and Tax Benefits with Ben Fraser

    301. Why the Wealthy Invest differently: Timing, Trends, and Tax Benefits with Ben Fraser
    Nov 24 2024
    In this episode, Thomas and Ryan are joined by Ben Fraser, Chief Investment Officer of Aspen Funds and host of the Invest Like a Billionaire podcast, to explore strategies of the ultra-wealthy and how they invest differently. They cover: - The difference between ultra-high-net-worth investors and retail investors - Why private markets, including real estate and private equity, are the cornerstone of billionaire investment strategies - The trade-offs between active and passive real estate investing - Key insights on evaluating sponsors and deals to avoid common pitfalls - Emerging trends in the alternative investment space - And much more! If you’re curious about how the wealthiest individuals protect and grow their capital—and how you can apply those strategies—this episode is full of actionable insights. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Visit PURE at: www.rentpure.com Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    45 mins
  • 300. The 14-Day Rule & Personal Use Days: Avoiding Common Pitfalls for STR Owners

    300. The 14-Day Rule & Personal Use Days: Avoiding Common Pitfalls for STR Owners
    Nov 17 2024
    In this episode of the Tax Smart REI podcast, Thomas and Ryan explore the critical nuances of personal use days for short-term rental properties, a topic that generates frequent questions from their community of real estate investors and tax-savvy listeners. They break down the 14-day rule, share actionable strategies to avoid common pitfalls, and provide clarity on how personal use impacts your tax benefits—especially for those leveraging the short-term rental loophole. Here’s what they discuss: - The 14-day rule and how it applies to short-term rental properties - What counts as personal use and how the IRS defines it - Travel days, family stays, and the gray areas of personal use - Best practices for keeping credible time logs & avoiding audit risks To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Visit PURE at: rentpure.com Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    36 mins
  • 299. Corporate Transparency Act Checklist: Avoid Costly Mistakes with FinCEN Filing Agents

    299. Corporate Transparency Act Checklist: Avoid Costly Mistakes with FinCEN Filing Agents
    Nov 10 2024
    In this episode, Thomas and Ryan are joined by Heather and Isaac from FinCEN Filing Agents to dive deep into the 2024 Corporate Transparency Act (CTA) and what it means for real estate investors and small business owners. They cover: - An overview of the Corporate Transparency Act - Key reporting requirements for LLCs and other entities - The penalties for non-compliance - Insights into exemptions, reporting updates, and the timeline for new and existing entities - Strategies for streamlining the filing process - Privacy concerns and how your information is safeguarded when filing under the CTA File your BOI Reports Today: https://tinyurl.com/Brandon-Hall To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Register for the Year-End Tax Impact Event: go.therealestatecpa.com/3zVWP7E Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    31 mins
  • 298. From Schedule E to Cost Segregation: Tackling Taxes with an Expert Q&A

    298. From Schedule E to Cost Segregation: Tackling Taxes with an Expert Q&A
    Nov 2 2024
    In this episode of the Tax Smart REI podcast, Thomas and Ryan dive into real estate tax strategies by addressing audience questions from their public community and Facebook group. Covering crucial topics, they guide listeners through the complexities of tax planning, especially for short-term rental owners, and how they can leverage tax rules to minimize liabilities. Here’s what they discuss: - Understanding when to use Schedule C vs. Schedule E - Short-term Rental Loopholes and Real Estate Professional Status - Travel, Meal, and Home Office Deductions - Year-End Moves & Capital Gains Strategies To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Register for the Year-End Tax Impact Event: go.therealestatecpa.com/3zVWP7E Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    41 mins
  • 297. Drilling Into Profits: A Case Study on Oil & Gas Working Interests with Troy Eckard

    297. Drilling Into Profits: A Case Study on Oil & Gas Working Interests with Troy Eckard
    Oct 29 2024
    In this episode, Thomas and Ryan are joined again by Troy Eckard of Eckard Enterprises to conclude our oil & gas series with a real-world case study on oil and gas working interests. They cover: - A detailed breakdown of a case study involving a working interest investment, including cost structures, potential pitfalls, and strategies for maximizing returns. - How to evaluate investment deals to avoid common mistakes, including understanding the true costs and potential revenue from drilling. - The impact of modern drilling technologies on reducing risk and improving success rates for working interest investors. - How to approach oil and gas as a long-term investment strategy that can generate ongoing cash flow while leveraging substantial tax benefits. - And much more! If you’re looking for ways to diversify your portfolio with alternative investments, this episode is packed with real-world oil & gas insights. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Register for the Year-End Tax Impact Event: go.therealestatecpa.com/3zVWP7E Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Checkout Thomas's new YouTube channel: www.youtube.com/@thomascastelli 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.
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    56 mins