Major League Real Estate Podcast

Hall CPA

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. 45. 1031 Exchange Capital in Syndications: TICs, DSTs, and UPREITs Explained

    4d ago

    45. 1031 Exchange Capital in Syndications: TICs, DSTs, and UPREITs Explained

    Can investors use 1031 exchange proceeds to invest in real estate syndications? The answer is yes, but it's not nearly as simple as many sponsors hope. In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down the most common structures used to bring 1031 exchange capital into syndications, including Tenants in Common (TIC) arrangements, Delaware Statutory Trusts (DSTs), and 721 Exchange/UPREIT structures. They discuss why 1031 investors are increasingly looking for passive investment options, the challenges syndicators face when accepting exchange capital, and the operational, legal, and tax considerations that come with each strategy. 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.

    27 min
  2. 44. What Every Syndicator Gets Wrong About Depreciation Recapture

    May 28

    44. What Every Syndicator Gets Wrong About Depreciation Recapture

    What happens when a real estate syndication exits and all that bonus depreciation comes back into play? In this episode, Nate Sosa and Thomas Castelli break down depreciation recapture, cost segregation, and the tax implications GPs and LPs need to understand before selling a deal. Topics discussed include: - Bonus depreciation and cost segregation - Depreciation recapture mechanics - 1245 vs. 1250 vs. 1231 gains - 1031 exchanges in syndications - Refinancing strategies - Partial asset dispositions - LP communication and tax planning - Time value of money and tax deferral 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.

    18 min
  3. 43. The Hidden Tax Problems Inside Real Estate Syndications

    May 21

    43. The Hidden Tax Problems Inside Real Estate Syndications

    In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli break down what happens when experienced CPAs integrate directly with syndicators and fund managers. Topics Covered: - Common operating agreement tax mistakes - Entity structuring and partnership considerations - K-1 season expectations and extension strategies - 1031 exchanges, refinance considerations, and exit planning - How to choose the right CPA for your syndication business Most syndicators think their CPA’s job starts and ends with filing partnership tax returns and sending out K-1s. But in reality, the right CPA should function as a strategic partner throughout the entire lifecycle of your deal. 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.

    24 min
  4. 42. How to Raise Capital Legally for Real Estate Deals with Attorney Mola Bosland

    May 14

    42. How to Raise Capital Legally for Real Estate Deals with Attorney Mola Bosland

    In this episode of the Major League Real Estate Podcast, Nate Sosa and Thomas Castelli sit down with securities and real estate attorney Mola Bosland to break down the legal and strategic side of real estate syndications. Mola shares how successful syndicators structure their entities, when to use a 506(b) vs. 506(c), the biggest mistakes new operators make when raising capital, and why investor trust matters more than flashy projections. The conversation also dives into fund structures, private equity partnerships, preferred returns, investor relations, and the growing institutionalization of real estate investing. Whether you’re raising capital for your first deal or scaling into larger funds and family office partnerships, this episode is packed with actionable guidance to help you stay compliant, protect investors, and grow sustainably. 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.

    40 min
  5. 41. S Corps, C Corps & Syndications: The Structuring Mistakes Investors Make

    May 7

    41. S Corps, C Corps & Syndications: The Structuring Mistakes Investors Make

    Should your real estate syndication use an S corporation, a C corporation, or an LLC taxed as a partnership? In this episode, Thomas Castelli and Nathan Sosa break down the real tax implications behind entity structuring for syndicators, fund managers, and passive investors. They explain why LLCs taxed as partnerships are typically the gold standard for real estate syndications, where S corps can accidentally limit depreciation benefits, and how C corps can create double taxation problems that investors often overlook. You’ll also learn: - Why depreciation and debt allocation matter so much in syndications - The hidden limitations of S corps for real estate investors - When a C-corp blocker actually makes sense - How GP entities and management companies should be structured - The biggest mistakes syndicators make before raising capital Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber 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.

    19 min
  6. 40. Why 1031 Exchanges Break in Syndications (And How to Work Around It)

    Apr 30

    40. Why 1031 Exchanges Break in Syndications (And How to Work Around It)

    In this episode of the Major League Real Estate Podcast, we break down everything you need to know about 1031 exchanges and why they get complicated fast when syndications are involved. We cover: - Why you can’t directly 1031 into a syndication - The biggest issues GPs and LPs run into when trying to defer taxes - Workarounds like Delaware Statutory Trusts (DSTs) and Tenants-in-Common (TIC) structures - Advanced strategies like drop-and-swap and how to plan for them on the front end - Common pitfalls including boot, debt replacement, and IRS scrutiny We also cover practical advice for syndicators, like how to structure deals upfront if you want to offer 1031 optionality, and what investors should look for when trying to defer gains into their next opportunity. Whether you're an active investor, passive LP, or syndicator, this episode will help you understand how to properly navigate 1031 exchanges without blowing up your deal or your tax strategy. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber 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.

    23 min
  7. 39. K-1s, Deadlines, and Tax Extensions: How Tax Season Is Hurting Your Long Game

    Apr 23

    39. K-1s, Deadlines, and Tax Extensions: How Tax Season Is Hurting Your Long Game

    In this episode, we’re breaking down one of the biggest misconceptions in real estate investing: the idea that you need to rush to file your taxes by April 15. If you’ve ever felt pressure to get your K-1s out early, file on time, or keep investors happy by hitting arbitrary deadlines, this episode is for you. We discuss why tax extensions are not only normal in the world of real estate syndications and funds, but often the smarter move. Rushing the process can lead to costly mistakes, amended returns, and unnecessary headaches for both operators and investors. You’ll learn how to properly set expectations with your LPs, why accuracy matters more than speed, and what really happens when you file without complete information. We also cover key lessons from this tax season, including common misunderstandings around bonus depreciation, passive losses, and how income from things like high-yield accounts can create unexpected tax implications. Plus, we walk through what you should be doing right now, post tax season, to review your returns, improve your processes, and plan ahead for the rest of the year. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber 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.

    22 min
  8. 38. Carried Interest: What’s Really Behind the "Loophole" and Why It’s Misunderstood

    Apr 16

    38. Carried Interest: What’s Really Behind the "Loophole" and Why It’s Misunderstood

    In this solo episode, Nate Sosa breaks down one of the most important — and most misunderstood — concepts in real estate syndication: carried interest. From its surprising origins in 16th-century shipping voyages to its modern-day use in private equity and real estate deals, Nate walks through how carried interest actually works, why it exists, and how it’s taxed. You’ll learn: - How GP/LP structures and waterfall distributions work - The difference between promote, profits interests, and equity - Why carried interest is taxed at favorable rates - The real risks GPs take (and why the upside exists) - What Congress has tried (and failed) to change about it - Common structuring mistakes that could trigger IRS issues Whether you’re an active sponsor or passive investor, this episode will help you better understand deal economics and what to watch for when evaluating opportunities. Request a free discovery meeting: go.therealestatecpa.com/mlre Get the Ultimate Guide for Real Estate Syndications: go.therealestatecpa.com/mlreultimateguide Subscribe to the REI Daily Newsletter: go.therealestatecpa.com/mlresubscriber 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.

    19 min
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Ratings & Reviews

5
out of 5
6 Ratings

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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