Major League Real Estate Podcast

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 Op...

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 busines...

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 a...

What happens when an investor dies, sells their partnership interest, or gets bought out of a real estate syndication? In this episode, Thomas Castelli and Nate Sosa explain Section 754 elections and how they affect real estate syndications, private equity funds, and partnership structures. They cover when these elections make sense, when they don't, and why every syndicator should understand the...

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 T...

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. 125...

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 exi...

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 t...

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...

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) struct...

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 syndicatio...

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 structu...

Brian Burke, CEO of Praxis Capital and author of The Hands-Off Investor, joins the show to break down the current state of real estate investing and why he believes multifamily is still too early to touch. We discuss: - Why the multifamily market looks like a “traffic collision” right now - The biggest mistake investors make trying to time the bottom - Why senior housing may be the most overlooked...

In this episode of the Major League Real Estate Podcast, Thomas Castelli and Nate Sosa break down one of the most misunderstood areas of partnership tax law: disguised sales. While many investors assume distributions and refinance proceeds are tax-free, the rules change when partnerships and contributed property are involved. Get it wrong, and what you thought was a tax-free event could actually b...

In this episode, Nate and Tom break down the truth behind private jet tax write-offs: what works, what doesn’t, and where investors get into trouble. They dive into how bonus depreciation can create significant tax savings, why most jet structures default to passive losses, and how rules like material participation, business use, and grouping elections can make or break your strategy. Plus, they w...

K-1 season can be confusing for real estate investors, especially when depreciation, passive losses, and capital accounts start showing up on your tax documents. In this episode, Nate and Tom break down the fundamentals of depreciation in real estate partnerships and how it impacts both general partners (GPs) and limited partners (LPs). They walk through how cost segregation studies accelerate ded...

In this episode of the Major League Real Estate Podcast, we sit down with Victor Menasce, tech executive turned real estate developer, host of the Real Estate Espresso Podcast, and author of Magnetic Capital, to break down what’s really happening in today’s market. From leaving Silicon Valley in 2009 to building multifamily projects in uncertain cycles, Victor shares how his background in tech sha...

In this episode of the Major League Real Estate Podcast, Thomas Castelli shares the full story of his journey, from attending local RIAs and investing as an LP, to joining the GP team on an 82-unit apartment complex, navigating hurricane due diligence, raising capital under pressure, and exiting during the chaos of COVID in 2020. But that’s not all. Tom also opens up about: - The hardest lesson he...

In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Jens Nielsen of Open Doors Capital to break down how he went from a 25-year IT career to full-time real estate and scaled from buying a couple of fourplexes to investing in 2,700+ multifamily units as a GP. Jens breaks down: - How he went from 0 to 19 units in year one and built momentum from...

Nathan and Matt dive into one of the most anxiety-inducing topics in real estate tax: IRS audits—specifically what a partnership audit actually looks like and how it differs from individual audits. They break down why partnership audits are far less common than most operators assume, how the current partnership audit regime works, and what really triggers IRS scrutiny. The conversation focuses on...

Nathan and Matt shift gears for a practical, nuts-and-bolts episode focused on year-end planning and what operators should be thinking about now to set up a smooth tax filing season. They walk through the key tax, accounting, and logistical items that tend to create friction during tax season—and how addressing them proactively can save time, reduce stress, and avoid last-minute surprises. From en...

Nathan starts by unpacking the difference between deductions and credits, then walks through how the 30% Investment Tax Credit (ITC) works when you install solar on commercial properties—plus how bonus depreciation layers on top of the credit under today’s rules. He explains why the Inflation Reduction Act boosted solar, what’s changing over the next few years, and where engineering studies come i...

In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Tait Duryea of Passive Income Pilots and Turbine Capital to unpack how he’s helping airline pilots and other high-earning professionals turn strong W-2 income into real wealth through passive investing in commercial real estate, oil and gas, and other private deals. Tait shares how he grew up...

In this episode of the Major League Real Estate Podcast, Nathan and Matt sit down with Edward Griffith of Hall CPA to demystify cost segregation for large CRE operators, fund managers, and syndicators—and how to turn engineered studies into real cash flow and tax advantages. Edward shares how his engineering background and 15+ years in property analysis and cost segregation led him to run the cost...

In this episode of the Major League Real Estate Podcast, hosts Nathan Sosa and Matt Hamilton sit down with Skylar from ATW Advisors to unpack how large CRE operators and syndicators can turn insurance from a deal-killing expense line into a strategic lever for protecting NOI and keeping closings on track. Skylar shares how she spent 17 years as a commercial insurance broker serving real estate own...