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!