Major League Real Estate Podcast

Hall CPA
  • 5.0 (7)
  • Business
  • Updated Weekly

The Major League Real Estate Podcast is the show for operators and sponsors who compete at the highest level. We dive deep into the journeys, investing frameworks, and tax strategies of elite portfolio builders, all while spotlighting these playmakers who build and scale multi-million-dollar portfolios. Whether you're syndicating deals, managing large assets, or scaling partnerships, you’ll hear firsthand how top performers get it done. We explore every strategy related to acquisitions, operations, and exits and break down the best ways to optimize your taxes for each one. Tune in for real stories, sharp insights, and proven frameworks you can use right now.

  1. 6d ago

    54. 5 Real Estate Syndication Tax Questions Every Limited Partner Should Know

    In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down some of the most common tax questions real estate sponsors hear from limited partners. When should LPs expect their K-1s? Can passive real estate losses offset W-2 income? Do you need an LLC to invest in a syndication? What happens when you invest through a retirement account? And what happens from a tax perspective when the property finally sells? Nate and Tom also unpack depreciation recapture, UBIT and UDFI, passive loss carryforwards, and why an individual LP generally can't simply initiate a 1031 exchange when a syndication sells. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    54. 5 Real Estate Syndication Tax Questions Every Limited Partner Should Know

  2. Aug 6

    53. Why A Will Isn't Enough: The Estate Planning Mistakes Investors Keep Making

    Why aren't we putting more emphasis on estate planning? In this episode, Nate Sosa and Thomas Castelli break down the essential estate planning strategies every real estate investor should understand. They cover why a simple will often isn't enough, how living trusts help avoid probate, the importance of powers of attorney and healthcare directives, and how estate planning intersects with tax planning. They also discuss estate tax exemptions, the step-up in basis, gifting strategies, and when more advanced trusts may become necessary as your portfolio grows. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    53. Why A Will Isn't Enough: The Estate Planning Mistakes Investors Keep Making

  3. Jul 30

    52. Too Big for REPS? The Tax Question Every Real Estate Operator Should Ask

    Many real estate investors assume that as their business grows, qualifying for Real Estate Professional Status becomes automatic. The reality is much more complicated. In this episode, Nate and Tom tackle the question: Can you become too big for REPS? They break down what actually qualifies as material participation, whether capital raising counts toward REPS, how delegation changes the analysis, and why large syndicators and fund managers need to understand the difference between running a real estate business and simply owning one. The discussion also covers notable tax court cases, President Trump's publicly discussed tax returns, common REPS misconceptions, and planning considerations as your portfolio grows. In this episode, you'll learn: - What Real Estate Professional Status actually requires. - Whether CEOs, fund managers, and syndicators can still qualify. - Why scaling your business may or may not affect your tax benefits. - The IRS's position on material participation. - Common REPS myths that continue circulating in the industry. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    52. Too Big for REPS? The Tax Question Every Real Estate Operator Should Ask

  4. Jul 23

    51. What's Next for Commercial Real Estate? According to a Broker Behind $10 Billion in Deals

    Commercial real estate is changing, and the smartest investors are already adapting. In this episode, Nate Sosa and Thomas Castelli sit down with Mark Sinnett, Head of Capital Markets for Quebec at Avison Young. After closing more than 800 commercial real estate transactions totaling over $10 billion, Mark shares what institutional investors are seeing before everyone else. They discuss: - Why retail may be the biggest opportunity today - Whether office buildings are making a comeback - What's really happening in multifamily housing - How sale-leaseback transactions create massive liquidity - The role AI will play in commercial real estate - Why every investor needs multiple exit strategies If you invest in commercial real estate or want to understand where institutional capital is moving, this episode is important for you. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    51. What's Next for Commercial Real Estate? According to a Broker Behind $10 Billion in Deals

  5. Jul 16

    50. The New Housing Bill and the Future of Institutional Investors with Troy Silfies

    Update: The 21st Century ROAD to Housing Act became law on July 11, 2026, after President Trump neither signed nor vetoed the bill within the constitutional deadline. In this episode, Nathan sits down with Troy Silfies, VP of Tax at Hall CPA, to discuss the new 21st Century Housing Bill and what it could mean for investors, builders, landlords, lenders, and prospective homebuyers. Together, they examine the proposed 350-home threshold for large institutional investors, the bill's key exceptions, build-to-rent developments, rent-to-own programs, manufactured housing, and other provisions that could influence housing supply and real estate investment. If you invest in real estate, this conversation will help you understand what's changing, what could happen next, and how the legislation may affect the market. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    50. The New Housing Bill and the Future of Institutional Investors with Troy Silfies

  6. Jul 9

    49. Opportunity Zones 2.0: The Biggest Changes Coming in 2027

    Qualified Opportunity Zones are back, and they're better than ever. With Opportunity Zones 2.0 becoming permanent under the new tax law, investors and real estate operators have a rare opportunity to reduce capital gains taxes while building long-term wealth. But the rules have changed. In this episode, Nate Sosa and Tom break down: - What Opportunity Zones actually are - The biggest changes in Opportunity Zones 2.0 - The new rolling 5-year tax benefit - Rural Opportunity Zones and the new 30% tax reduction - The upcoming Opportunity Zone maps - Why 2026 and 2027 are critical planning years - Opportunity Zones vs. 1031 Exchanges - Common mistakes investors make If you're selling a business, real estate, stocks, cryptocurrency, or have large capital gains, this episode could save you significant taxes. Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    49. Opportunity Zones 2.0: The Biggest Changes Coming in 2027

  7. Jul 2

    48. The Case for Manufactured Housing: America's Most Durable Real Estate Asset with "Ali" Nasir Ali

    Today's manufactured housing communities are becoming one of the strongest-performing real estate asset classes available. In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli sit down with Ali, Managing Director and Co-Founder of Rise360 Ventures, whose family has spent more than 44 years investing in manufactured housing. Ali shares how growing up in the business shaped his investing philosophy, why manufactured housing consistently outperforms many traditional real estate asset classes, and how investors can benefit from stable cash flow, lower operating costs, tenant-owned homes, and powerful tax advantages. They also discuss: - Why tenant-owned homes create a better business model - How manufactured housing compares to multifamily investing - The tax benefits of cost segregation and bonus depreciation - Building generational wealth through 1031 exchanges - Why manufactured housing may help solve America's housing shortage - How AI is changing real estate investing and operations Request a free discovery meeting: go.therealestatecpa.com/mlre Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: www.therealestatecpa.com/careers/ Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question Connect with Ali: rise360ventures.com The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    48. The Case for Manufactured Housing: America's Most Durable Real Estate Asset with "Ali" Nasir Ali

  8. Jun 18

    47. Why This Airline Pilot Chose Passive Investing (Oil & Gas, Senior Living, & More)

    In this episode, Nathan Sosa sits down with Tait Duryea, Founder and CEO of Turbine Capital, for part one of the active vs. passive investing debate. Tait shares how he went from airline pilot to building an investment firm and explains why many high-income professionals are turning to passive investing opportunities in real estate and energy. The conversation breaks down today's most attractive asset classes, including multifamily, senior living, industrial real estate, and oil & gas. Tait also explains how passive investors can benefit from depreciation, K-1 losses, and unique tax incentives available through oil and gas investments. Topics Discussed: - The biggest misconception about passive investing - How to evaluate fund managers and syndicators - Senior living and industrial real estate opportunities - Oil & gas investing and tax benefits Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Submit your questions to: go.therealestatecpa.com/question The Major League Real Estate podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, investing, financial, 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.

    47. Why This Airline Pilot Chose Passive Investing (Oil & Gas, Senior Living, & More)
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About

The Major League Real Estate Podcast is the show for operators and sponsors who compete at the highest level. We dive deep into the journeys, investing frameworks, and tax strategies of elite portfolio builders, all while spotlighting these playmakers who build and scale multi-million-dollar portfolios. Whether you're syndicating deals, managing large assets, or scaling partnerships, you’ll hear firsthand how top performers get it done. We explore every strategy related to acquisitions, operations, and exits and break down the best ways to optimize your taxes for each one. Tune in for real stories, sharp insights, and proven frameworks you can use right now.

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