NYC Foreclosures, Development Timing, and AI Underwriting with Dylan Vaccaro
Release Date: 10/01/2025
How Deal Queue Cuts Analysis Time by 90% with Dylan Vaccaro
The Academy Presents podcast
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
The Academy Presents podcast
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
The Academy Presents podcast
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
The Academy Presents podcast
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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Building Teams and Finding Your Superpower in Real Estate with Sean Griffith
The Academy Presents podcast
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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What Every LP Should Know Before Writing That Check with Sean Griffith
The Academy Presents podcast
What does it take to go from writing your first passive investment check to becoming a general partner with 3,500 doors—and what due diligence mistakes do most new investors make? In this episode, Angel Williams sits down with Sean Griffith, who shares his 10+ year journey from passive investor to general partner. Sean Griffith reveals how his first deal in Carrollton, Texas spoiled him with 12-14% cash-on-cash returns when 10% was the minimum standard. He explains the critical importance of reading PPMs thoroughly, getting SEC attorney reviews, and asking hard questions about contingency...
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Long-Term Hold vs. Quick Flips with Diana Gipe
The Academy Presents podcast
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
The Academy Presents podcast
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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Syndication Structures and Industrial Real Estate Q&A with Daniel Holmlund
The Academy Presents podcast
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 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 bank workout situations, why rent stabilization makes NYC attractive for contrarian investors, and discusses the role of luck versus skill in generational wealth building. The conversation shifts to Angel's mobile home community development in Waco, exploring exit strategies at various completion stages, before concluding with Dylan's AI-powered solution that reduces underwriting time from 2-3 hours to 10-15 minutes.
[00:01 - 07:00] NYC Market Opportunities in Distressed Times
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How regulatory pressure drove prices down 30-50% creating buying opportunities
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Why Dylan buys most NYC deals under the debt in bank workout situations
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The contrarian thesis: when everyone zigs, you should zag
[07:01 - 12:00] Timing, Luck, and Generational Wealth
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Why "the worst developers who time the market right will seem like geniuses"
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How "the harder I work, the luckier I get" creates opportunities
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The importance of staying power through economic cycles
[12:01 - 18:00] The Crane Theory and Development Timing
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How maximum crane activity in established cities signals market tops
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Why building through recessions can position you perfectly for recovery
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The 2008 lesson: when building becomes too obvious, reassess
[18:01 - 24:00] Mobile Home Community Development
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Angel's 104-pad Waco project near Amazon facility and top school district
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Multiple exit strategies: sell at drawings, roadways, or fully developed
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Why resident-owned homes create 10+ year tenancies vs. 18-month park-owned turnover
[24:01 - 26:30] AI-Powered Underwriting Solution
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How DealQueue reduces underwriting time from 2-3 hours to 10-15 minutes
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Solving the data parsing pain point from PDFs, Excel, and handwritten notes
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Why this problem resonates "across the board" from beginners to professionals
Connect with Dylan: https://www.linkedin.com/in/dylan-vaccaro-4450b9140/
Key Quotes:
"The worst developers who time the market right and get lucky in an upscale market will seem like geniuses. But even the best developers in a downward market will seem like a fool." - Dylan Vaccaro
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