In this episode of Dealmaker$, Shane sits down with David DeSantis, Chief Operating Officer and partner at TTR Sotheby’s International Realty — one of the most influential figures in DC real estate and a leader who helped grow the company from one small boutique office to 500 agents and $5B in annual sales.

David reflects on his start in public policy — from Capitol Hill to the Clinton White House and the Federal Trade Commission, where he became Chief of Staff at just 29 years old. But politics wasn’t the long-term path. The grind, the negativity, and the lack of personal autonomy pushed him toward a new frontier: real estate.

He shares his transition from:

• Commercial real estate at Charles E. Smith (now JBG Smith)

• To mixed-use development at Hoffman & Associates

• To finally joining TTR Sotheby’s in 2007, when the firm had one office, 30 agents, and $300M in yearly volume — a fraction of what it is today.

Shane and David dig into professionalism in real estate, why agents should treat it like a profession (not a hobby), and how TTR built a reputation for white-glove service across all price points — not just the ultra-luxury tier.

David breaks down:

• How ultra-high-net-worth buyers actually behave (more emotional than people think)

• Why DC luxury buyers are less flashy than NYC/Miami/LA

• The “Trump bump” and influx of high-profile buyers

• Why DC won’t ever see $100M condos

• The rise of branded residences like Four Seasons

• Why buyers today refuse renovation projects

• Why everything “starts to look the same” in modern spec homes

He shares stories from extraordinary deals — including the original Herbert Hoover Camp David retreat (ultimately purchased by The Church of Scientology) and insights into representing highly private, global buyers.

The market talk gets real and honest:

• Federal layoffs vs. federal spending

• Why Q3 and Q4 will reveal whether the region heads into recession

• The outer-ring suburbs that may feel job cuts most

• How office-to-residential conversions could reshape downtown DC

David closes with invaluable leadership wisdom:

• Create win-wins, not zero-sum negotiations

• Stay calm — emotion kills deals

• Understand the other party’s motivations

• Grow with your clients if you want to break into luxury

This episode is a masterclass in luxury strategy, regional economics, ethics, client psychology, and building a 20-year legacy in one of the nation’s most influential markets.

This is Dealmaker$ — where real deals meet real strategy.