From IT to Investor: Alina Trigub’s Journey in Passive Real Estate
Release Date: 08/11/2025
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_outlineHow can focusing on relationships, education, and compliance help real estate investors raise private capital with confidence?
In this episode, Alina Trigub, Head of Investor Relations at TF Management Group and founder of SAMO Financial, shares her journey from immigrating to the U.S., working in accounting and IT, to building a career in passive real estate investing. She discusses the turning points that led her to syndications, the tax benefits of real estate, and her step-by-step approach to raising private capital. Listeners will learn why understanding both the investor and operator perspectives is vital, how to build lasting trust with investors, and the importance of staying within regulatory guidelines.
[00:01 - 04:42] From Accounting to Passive Investing
- How Alina’s early career in accounting and IT shaped her financial perspective
- Why rising taxes pushed her to explore real estate
- The significance of her first syndication investment and how it led to ongoing opportunities
[04:43 - 07:39] Lessons from Early Deals
- Why initial naivety can sometimes work in an investor’s favor
- The importance of learning through each investment
- What the 1031 exchange is and why it matters for tax deferral
[07:40 - 11:03] The Power of Real Estate Over Paper Assets
- Why tangible assets often provide more stability
- The need for diversification beyond Wall Street
- How tax benefits can create a stronger financial position
[11:04 - 15:21] Raising Capital: The Three Big F’s
- Why understanding both the active and passive sides is crucial
- The three pillars: Focus, Find, Follow
- How to define and target the ideal investor avatar
[15:22 - 18:30] Practical Steps for Investor Engagement
- How to maintain trust and transparency with investors
- Why compliance is non-negotiable in capital raising
- What long-term success looks like in investor relations
Connect with Alina:
https://www.linkedin.com/in/alinatrigub/
Key Quotes:
“Sometimes there is a blessing in the naivety of not knowing.” - Alina Trigub
“Where else can you get the tax advantages, if not in real estate?” - Alina Trigub
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