Building Generational Wealth in NYC with Dylan Vaccaro

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

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