Podcast
Tax Smart Real Estate Investors Podcast
Hosted by Hall CPA · EN
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 serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch.
Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information.
Enjoy!
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. 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
186episodes
Episodes
Newest firstAll episodes
378. The Truth About Paying Your Kids Legally (And Whether The IRS Cares)
2d ago00:31:45Summary readyCan you legally pay your children through your business and use it to build tax-free wealth for their future? In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa break down one of the most powerful family tax strategies available to business owners and real estate investors. You’ll learn: - How to legally pay your kids through your business - The entity structures required to avoid payroll taxes - What jobs children can reasonably perform - How much you can realistically pay them - Roth IRA strategies for children - Trump Accounts vs. 529 Plans If you're a real estate investor or business owner with kids, this episode could completely change how you think about family wealth building and tax planning. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle Register for the FREE Investing Debate: go.therealestatecpa.com/debate Submit your question for Tom & Nathan: go.therealestatecpa.com/question 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. 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.
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MLRE: How to Raise Capital Legally for Real Estate Deals with Attorney Mola Bosland
1w ago00:39:48Summary readyIn 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.
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377. You Can't Escape Depreciation Recapture (But Here's How to Defer It)
1w ago00:31:21Summary readyWhat happens when you sell a rental property after taking depreciation deductions? Many investors are shocked to learn they may owe more than just capital gains tax. In this episode, Thomas Castelli and Nate Sosa break down how depreciation recapture actually works, including the three different tax “buckets” investors need to understand: Section 1245 recapture, unrecaptured Section 1250 gain, and Section 1231 capital gains. They explain how bonus depreciation, cost segregation studies, and qualified improvement property impact your taxes when you sell and why accelerated depreciation can still make sense despite future recapture. If you own rental properties, short-term rentals, or commercial real estate, this episode will help you understand what taxes to expect when exiting a deal and how to plan ahead to minimize them. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle Submit your question for Tom & Nathan: go.therealestatecpa.com/question 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. 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.
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MLRE: S Corps, C Corps & Syndications: The Structuring Mistakes Investors Make
2w ago00:19:25Summary readyShould your real estate syndication use an S corporation, a C corporation, or an LLC taxed as a partnership? In this episode, Thomas Castelli and Nate 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.
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376. The Depreciation Mistake That Could Cost You at Audit (And Baby Roths)
2w ago00:20:12Summary readyIn this Q&A episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa answer real questions from listeners, clients, and the Tax Smart community. They cover a wide range of topics, from how to properly track your time for material participation, to how short-term rentals should be classified for tax purposes, to what really qualifies for bonus depreciation under the latest tax law changes. They also break down strategies for investing for your kids’ future, including 529 plans, Roth IRAs, and newer account options, along with the pros and cons of each. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle Submit your question for Tom & Nathan: go.therealestatecpa.com/question Time Log: https://www.therealestatecpa.com/time-log/ 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. 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.
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MLRE: Why 1031 Exchanges Break in Syndications (And How to Work Around It)
3w ago00:23:05Summary readyIn 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.
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375. Why S Corporations Are a Disaster for Rental Properties (And How to Get Out)
3w ago00:29:55Summary readyIf you’ve ever been told to put your rental properties in an S corporation…this episode could save you thousands (or more) in taxes. In this episode of the Tax Smart REI Podcast, Thomas Castelli and Nate Sosa break down one of the most common and expensive mistakes real estate investors make: holding rental properties inside an S corp. They cover: - Why S corporations don’t work for rental real estate - The hidden tax traps that can cost you big later - What happens when your property appreciates (and you want out) - Whether there’s any way to exit an S corp tax-free (spoiler: not really) - When S Corps actually do make sense in real estate Plus, they answer a common listener question: How many rental properties do you really need to qualify for Real Estate Professional Status? To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle Submit your question for Tom & Nathan: go.therealestatecpa.com/question 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. 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.
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MLRE: K-1s, Deadlines, and Tax Extensions: How Tax Season Is Hurting Your Long Game
4w ago00:22:14Summary readyIn 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.
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374. How People Make $50K Tax-Free Renting Their Home (Augusta Rule)
Apr 2100:31:01Summary readyIn this episode of the Tax Smart REI Podcast, Thomas Castelli and Nathan Sosa break down the Augusta Rule, one of the most talked-about and misunderstood tax strategies in real estate. In this episode, we cover: - Where the Augusta Rule came from and how it ended up in the tax code - Who actually qualifies (and who doesn’t) - Why this strategy is often overhyped, especially for business owners - Real examples of homeowners earning $10K–$50K tax-free during major events - How events like the World Cup, Super Bowl, and Olympics can create big opportunities - The most common mistakes that can disqualify the strategy We also answer a listener's question about getting a rental property out of an S-corp and why that can become a tricky (and expensive) situation if you’re not careful. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Get the FREE Ultimate STR Tax Strategy Bundle: go.therealestatecpa.com/strbundle Submit your question for Tom & Nathan: go.therealestatecpa.com/question 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. 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.
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MLRE: Carried Interest: What’s Really Behind the “Loophole” and Why It's Misunderstood
Apr 1600:19:16Summary readyIn 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.
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