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 of human verification—AI assists but never replaces the underwriter's judgment. The conversation covers conservative underwriting assumptions, the difference between T-1, T-3, and T-12 statements, and why calculating cap rates on total invested capital matters more than purchase price alone.

[00:00 - 05:00] Introduction to Deal Queue

• How Deal Queue reduces underwriting from 2-3 hours to 10-15 minutes

• The platform extracts data and populates custom Excel models automatically

• Built-in models available for beginners learning multifamily underwriting

[05:01 - 10:00] Live Platform Demonstration Begins

• Upload process for rent rolls, T-12s, and offering memorandums

• How the system handles both PDF and Excel formats seamlessly

• Pricing structure: $30/month for preset models, $175/month for custom integration

[10:01 - 16:00] The Data Parsing Challenge

• Why manual data entry traditionally consumes hours of underwriting time

• The importance of organizing deal files in a centralized pipeline

• Angel's insight: underwriting is your business plan, not just an LOI tool

[16:01 - 20:00] Verification and Expense Analysis

• How Deal Queue flags suspicious expense categorizations that inflate NOI

• Live example: identifying CapEx items misclassified as below-the-line expenses

• Why plumbing, utilities, and appliance repairs shouldn't be one-time expenses

[20:01 - 24:00] Conservative Underwriting Principles

• Dylan's default assumptions: 5% vacancy and 2-3% annual growth rates

• Understanding T-1 vs. T-3 vs. T-12 financial statements for lending

• Why cap rates should be calculated on total invested capital, not just purchase price

[24:01 - 25:15] The Human Element in AI Underwriting

• Angel's warning: always back-check AI outputs—no tool does everything

• Regional expertise and market knowledge remain irreplaceable

• How increased deal volume (6-7 daily vs. 1-2) improves acquisition probability

Connect with Dylan: https://www.linkedin.com/in/dylan-vaccaro-4450b9140/
Deal Queue Website: dealq.ai

Key Quotes:

"Your underwriting is your business plan. It's just not always looked at that way." - Angel Williams

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention you're part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!

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 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

• How regulatory pressure drove prices down 30-50% creating buying opportunities

• Why Dylan buys most NYC deals under the debt in bank workout situations

• The contrarian thesis: when everyone zigs, you should zag

[07:01 - 12:00] Timing, Luck, and Generational Wealth

• Why "the worst developers who time the market right will seem like geniuses"

• How "the harder I work, the luckier I get" creates opportunities

• The importance of staying power through economic cycles

[12:01 - 18:00] The Crane Theory and Development Timing

• How maximum crane activity in established cities signals market tops

• Why building through recessions can position you perfectly for recovery

• The 2008 lesson: when building becomes too obvious, reassess

[18:01 - 24:00] Mobile Home Community Development

• Angel's 104-pad Waco project near Amazon facility and top school district

• Multiple exit strategies: sell at drawings, roadways, or fully developed

• Why resident-owned homes create 10+ year tenancies vs. 18-month park-owned turnover

[24:01 - 26:30] AI-Powered Underwriting Solution

• How DealQueue reduces underwriting time from 2-3 hours to 10-15 minutes

• Solving the data parsing pain point from PDFs, Excel, and handwritten notes

• 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

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!

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 a $7+ billion portfolio. He reveals the three cardinal investing principles he learned from Greenberger: control your purchase price, control who makes decisions, and maintain staying power. This conversation explores why Time Equities never sells, how neighborhood gentrification creates massive wealth, and why positive cash flow from day one has returned to the NYC market for the first time in years.

[00:01 - 08:00] From Architecture to Real Estate Operations

• Why Dylan switched from architecture after realizing "the pay of an artist" with engineering skills

• The three essential syndicator skills: finding deals, raising capital, understanding capital structure

• How working in BTR lending and private equity prepared him for operations

[08:01 - 16:00] The Three Cardinal Principles of Real Estate Investing

• Why purchase price determines everything about a deal's success potential

• How control over decision-making separates winning deals from disasters

• The Clinton Hill story: $12M building lost to foreclosure, returned for free, now worth $1.8B

[16:01 - 22:00] Why Buy and Hold Beats Value-Add Flips

• How time fixes most mistakes in real estate investing

• Why exit cap rate projections are "always gonna be wrong"

• The tax inefficiency of forced 1031 exchanges under time pressure

[22:01 - 26:25] NYC Market Opportunities and Neighborhood Intelligence

• Why every deal Dylan underwrites now cash flows from day one (first time in 2-3 years)

• How Upper East Side demographics shifted from age 65-70 to 35-40 in just two years

• The art and science of understanding neighborhood gentrification patterns

Connect with Dylan: https://www.linkedin.com/in/dylan-vaccaro-4450b9140/

Key Quotes: "The only one thing true about your proforma is it's always gonna be wrong." - Dylan Vaccaro

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!

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 returns always come with higher risks, and how Angel's transparency during crisis moments provides rare GP insights to her LP investors. This conversation covers practical stress management, the value of continuous learning, and why the LP-to-GP pathway provides essential preparation for the increased responsibilities and liabilities of active investing.

[00:01 - 07:00] The Lizard Brain and Stress Management

• How 2-million-year-old brain reactions cause unnecessary panic in modern investing

• Bobby Castro's concept of "non-refundable minutes" and choosing what deserves worry

• Using habit formation techniques to retrain automatic stress responses

[07:01 - 12:00] Learning from LP Experience as Preparation for GP Role

• How Angel draws on her passive investment experiences during active challenges

• The value of Charles Lame's meticulous record-keeping as a "serial passive investor"

• Why experienced LPs represent an underutilized resource for new GPs

[12:01 - 17:00] The Hidden Reality of GP Risk

• Why GPs can lose far more than their initial investment when deals go wrong

• The fundamental risk difference: LPs lose their investment, GPs face unlimited liability

• Why GP compensation reflects the additional risk and responsibility they assume

[17:01 - 21:00] Transparency and Community Building

• How Angel's openness about struggles provides rare GP education to LP investors

• The importance of contingency planning and realistic risk assessment

• Sean's approach to sharing both successful and challenging investment experiences

Connect with Sean: Website: twtmultifamily.com/book-a-call

Upcoming Event: AIM Denton Meetup - Monday, October 15th at Houlihan's Panel featuring experienced GP, new GP, and veteran passive investor Charles Lame

Key Quotes:

"If there's more return, there's gonna be more risk... you always have to tell yourself, if I'm getting a much bigger return, there's a much bigger risk." - Sean Griffith

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!

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 relationships, and how this honesty actually builds more trust than trying to fake expertise. This conversation explores team dynamics, the importance of great communication (highlighting standout sponsors), and practical wisdom about prioritization and managing stress in high-pressure deal situations.

[00:01 - 05:00] The Power of Persistence and Coaching

• Why daily practice and persistence are essential for mastering real estate skills

• How coaching helps you go "faster, sooner" and avoid expensive mistakes

• The kitchen table moment that led Sean from passive investor to general partner

[05:01 - 10:00] Finding Your Superpower and Being Honest About Weaknesses

• Angel's approach: "Underwriting is not my thing, but I can get you in touch with the guy who it is"

• How honesty about limitations builds more investor trust than fake expertise

• Sean's wife as the organizational backbone keeping him on track

[10:01 - 16:00] Building Complementary Teams and Extended Networks

• Why you need team members who can diplomatically handle difficult conversations

• How different roles (asset managers, underwriters, brokers) speak different "languages"

• The importance of having liquidity on the team for upfront expenses and emergencies

[16:01 - 21:00] Communication Excellence and Prioritization

• Why Elaine Viegas, Daniel Canterbury, and Don Naim excel at investor communication

• Learning prioritization by studying how great sponsors handle crises

• Sean's grandmother's wisdom: worry about what you can control, pray about what you can't

Connect with Sean Griffith: https://www.linkedin.com/in/shawn-griffith/

Key Quotes:

"We react to things like it's a life or death situation. And it's usually not... how much stuff these days is really life or death?" - Angel Williams

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!

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 planning. This conversation covers the reality of illiquid investments, the impact of events like COVID on cash flow expectations, and why vetting sponsorship teams is essential before writing large checks. Sean Griffith also discusses the transition from Wall Street retirement planning to active real estate investing and the value of mentorship in avoiding expensive mistakes.

[00:01 - 07:00] Getting Started: The First Deal and PPM Education

• How Sean Griffith's first Carrollton, Texas deal returned 3x with 12-14% cash-on-cash distributions

• Why paying an SEC attorney $500 to review your first PPM is worth the investment

• The reality that passive investments are illiquid until property sale or major capital events

[07:01 - 12:00] Due Diligence and Risk Assessment

• Why you should never be a "totally passive" passive investor

• How to use the 14-15 page risk section in PPMs to ask better questions

• The importance of vetting sponsorship teams through multiple references and channels

[12:01 - 17:30] Operational Realities and Contingency Planning

• Real examples of what can go wrong: hurricanes, fires, and tragic accidents

• Why asking about deep pockets and capital reserves is crucial before investing

• How capital calls happen and what they reveal about property performance

[17:31 - 22:15] The LP to GP Transition

• How kitchen table retirement planning revealed Wall Street's limitations

• Why taking care of tenants must be the top priority for sustainable success

• The value of mentorship and coaching to avoid expensive beginner mistakes

Connect with Sean Griffith: https://www.linkedin.com/in/shawn-griffith/

Key Quotes:

"Don't just jump in and be a totally passive, passive investor. Get off your butt, do a little homework. 'Cause this is your hard earned money." - Sean Griffith

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!

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 discuss current economic uncertainty, rising grocery costs as inflation indicators, and why few investors actually plan short-term exits despite market pressures. This conversation covers the intersection of tax strategy, investment philosophy, and market timing, plus Core's additional services including energy efficiency tax credits.

[00:01 - 04:00] Recapture Mechanics and Investment Timeline

• How recapture obligations are based on original purchase price, not sale price

• Why holding properties 3-5+ years significantly reduces or eliminates recapture fees

• The conservative approach to cost segregation that preserves ongoing straight-line depreciation benefits

[04:01 - 08:00] Investment Philosophy: Hold vs. Flip

• Angel's residential background of holding properties "until the wheels fall off"

• Why infinite returns through long-term ownership appeal more than quick flips

• Diana's observation that few investors actually plan short-term exits despite market talk

[08:01 - 11:00] Economic Uncertainty and Market Timing

• How current economic volatility makes short-term exit planning risky

• Real-world inflation examples: grocery costs rising from $1,000 to $1,250+ monthly

• Historical perspective on interest rates and the "golden era" ending

[11:01 - 13:15] Additional Tax Benefits and Services

• Energy efficiency tax credits: 179D for new construction (up to 80 cents per square foot)

• HVAC, lighting, and window replacement credits for existing properties

• Why solar is challenging in hail-prone areas but wind energy may be viable

Key Quotes:

"The longer you hold it, the smaller the recapture gets. That's why we say three to five years... by then there's not even a recapture fee to look at." - Diana Gipe

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!

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 the future, enabling better investment decisions and exit planning. This conversation explores the relationship-driven approach that sets Core apart in a saturated market, year-end tax deadlines, and how providing additional value like annual recapture projections could differentiate syndication sponsors in competitive markets.

[00:01 - 04:00] Understanding Recapture Analysis

• How recapture analysis helps investors plan for property sales 3-5 years in advance

• Why Core's internal CPA with 25+ years of cost segregation experience provides these projections

• The mathematical reality of passive investment recapture when multiple deals sell simultaneously

[04:01 - 07:30] Strategic Tax Planning Beyond Cost Segregation

• How recapture analysis becomes a competitive differentiator for syndication sponsors

• Why providing annual recapture projections with K-1s could set sponsors apart

• The concept of cost segregation as a comprehensive tax planning strategy, not just a one-time service

[07:31 - 10:00] Relationship-Driven Service Philosophy

• Diana's personal approach: knowing clients by name and understanding their long-term goals

• How Core supports investors from first property to 10+ property portfolios

• The emotional satisfaction of helping clients avoid large tax bills or receive unexpected refunds

[10:01 - 12:05] Year-End Timing and Market Realities

• How December closings can still benefit from same-year cost segregation

• Why September through year-end becomes the busiest period for tax planning

• Core's ability to handle last-minute requests while maintaining quality standards

Connect with Diana and Core: https://www.linkedin.com/in/dianagipe/

Key Quotes:

"Knowledge is power... we wanna make sure that you're equipped long term so that when you're going into buying properties, you can call me on the fly." - Diana Gipe

Visit sponsorcloud.io/contact today and unlock $2,000 of free services exclusively for REI Rocks community members! Get automated syndication and investor relationship management tools to save time and money. Mention your part of the REI Rocks community for exclusive offers. Help make affordable, low-cost education summits possible. Check out Sponsor Cloud today!