Why Quality Matters in Cost Segregation with Diana Gipe
Release Date: 09/15/2025
How Deal Queue Cuts Analysis Time by 90% with Dylan Vaccaro
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In this episode, Dylan Vaccaro demonstrates Deal Queue, his AI-powered underwriting platform that transforms the grueling 2-3 hour underwriting process into a streamlined 10-15 minute workflow. Through a live demonstration, Dylan shows how the tool parses rent rolls, T-12s, and offering memorandums from PDFs and Excel files, automatically populating custom financial models while flagging common seller manipulations like miscategorized expenses. Angel emphasizes that underwriting should be treated as a living business plan rather than just an LOI tool, while both discuss the critical importance...
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NYC Foreclosures, Development Timing, and AI Underwriting with Dylan Vaccaro
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What happens when NYC properties drop 30-50% in value and investors can buy buildings for less than the debt—and how do you know when a construction boom signals the market top? In this continuation episode, Dylan Vaccaro reveals how regulatory pressure and investor flight have created unprecedented opportunities in New York City real estate. He explains his "crane theory" for identifying market tops—when you see maximum construction activity in an established city, it's usually time to stop building and start preparing for the downturn. Dylan shares insights about buying properties in...
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Building Generational Wealth in NYC with Dylan Vaccaro
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What happens when a building bought for $10,000 per door gets lost to foreclosure, returned by the bank for free, and eventually becomes worth $1.2 million per unit—and what does that teach us about staying power? In this episode, Angel Williams sits down with Dylan Vaccaro, a New York City multifamily investor who works alongside self-made real estate billionaire Francis Greenberger at Time Equities. Dylan shares his unconventional journey from architecture school to USC's real estate program, through lending and capital raising, to his current role managing acquisitions and operations for...
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The Hidden Risks of General Partnership Investing with Sean Griffith
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What's the fundamental difference between losing $50,000 as an LP versus potentially losing much more as a GP when deals go sideways—and how do you manage the stress that comes with higher stakes? In this final episode with Sean, Angel and Sean dive into the psychological and financial realities of real estate investing at different levels. Sean explains the "lizard brain" reactions that cause panic over non-life-threatening situations and shares wisdom from habit-formation books like Atomic Habits. They discuss the critical risk difference between limited and general partners, why higher...
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What happens when you stop trying to do everything yourself and start focusing on your superpower while building a team around your weaknesses? In this continuation episode, Sean shares how he and his wife transitioned from their kitchen table retirement crisis to successfully closing multiple general partnership deals within months. He explains the power of persistence, finding the right coaching, and building complementary partnerships where each person focuses on their strengths. Angel reveals her approach to being upfront about not doing underwriting while excelling at investor...
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Long-Term Hold vs. Quick Flips with Diana Gipe
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When does it make sense to hold real estate "until the wheels fall off" versus flipping for quick profits—and how does cost segregation factor into that decision? In this final episode with Diana Gipe from Core, Angel and Diana explore investment philosophy and timing in an uncertain economic environment. Diana reveals how recapture obligations diminish over time, making long-term holds more attractive from a tax perspective. Angel shares her residential investing background and preference for infinite returns through extended ownership, questioning the 3-5 year multifamily flip model. They...
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Recapture Analysis and Long-Term Tax Planning with Diana Gipe
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What happens when you discover there's a tax planning tool you've never heard of that could save you thousands on property sales—and it's been available all along? In this continuation episode, Diana Gipe from Core reveals advanced tax planning strategies that go far beyond basic cost segregation. She introduces recapture analysis, a service Angel had never encountered despite years in real estate investing, which helps investors understand the true cost of selling properties with accelerated depreciation. Diana explains how Core's internal CPA can project recapture scenarios 3-5 years into...
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Why Quality Matters in Cost Segregation with Diana Gipe
The Academy Presents podcast
What does it mean when a cost segregation company has zero IRS disallowances in 18 years of business—and why does that matter more than ever with the IRS forming dedicated cost seg review teams? In this episode, Angel Williams sits down with Diana, Director of Operations at Core, to discuss why quality matters more than price in cost segregation services. Diana explains Core's rigorous engineering process, including on-site property visits and detailed documentation that has resulted in zero disallowances over 18 years. She reveals how the IRS has formed specialized cost segregation review...
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What happens when you combine syndication education with a deep-dive Q&A about industrial real estate operations—and discover why "ugly buildings that cash flow are sexy"? In this final episode of the three-part series, Daniel Holmlund wraps up his industrial flex space presentation with syndication fundamentals and answers Angel's detailed operational questions. He explains the difference between 506B and 506C offerings, preferred return structures, and how LLC partnerships distribute income and depreciation benefits. Angel dives deep into practical concerns: temperature control...
info_outlineWhat does it mean when a cost segregation company has zero IRS disallowances in 18 years of business—and why does that matter more than ever with the IRS forming dedicated cost seg review teams?
In this episode, Angel Williams sits down with Diana, Director of Operations at Core, to discuss why quality matters more than price in cost segregation services. Diana explains Core's rigorous engineering process, including on-site property visits and detailed documentation that has resulted in zero disallowances over 18 years. She reveals how the IRS has formed specialized cost segregation review teams as bonus depreciation approaches its sunset, and shares practical strategies like lookback studies for older properties and piggyback studies for renovations. This conversation covers the difference between fly-by-night operators doing "virtual walkthroughs on cell phones" versus professional engineering firms, plus Core's additional services including tax credits and disposition studies.
[00:01 - 06:00] Quality vs. Price in Cost Segregation
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Why Core's 18-year track record with zero IRS disallowances matters for audit protection
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How the IRS has formed dedicated cost segregation review teams as 100% bonus depreciation sunsets
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The difference between $2,000 "trunk of the car" operators and professional engineering firms
[06:01 - 12:00] Engineering Process and On-Site Visits
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Why Core's engineers visit every property instead of relying on virtual walkthroughs
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How detailed documentation includes everything from flagpoles to flooring materials
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The value of engineers advising on CapEx spending before renovations begin
[12:01 - 17:00] Lookback and Piggyback Studies
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How 481 forms allow one-time lookback studies for properties purchased 3-5 years ago
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Why piggyback studies can accelerate depreciation on completed renovations separately
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The strategic timing of cost segregation for capital improvement projects
[17:01 - 20:40] Beyond Basic Cost Segregation Services
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Disposition studies for properties undergoing major renovations or demolition
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Additional tax credit services: 45L credits, 179D credits, and green retrofits
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How Core acts as a "business consulting firm" rather than just a cost segregation provider
Connect with Diana and Core: https://www.linkedin.com/in/dianagipe/
Key Quotes: "Out of that 18 years, we've had zero disallowances. And that's because our engineers take this serious. A lot of them have worked internally for the IRS." - Diana Gipe
"It's like winning the lottery. Do you want your money now or later? It's yours. Just take it now while it's still here." - Diana Gipe
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