The Rich Somers Report Why Billionaires are Quietly Moving to Florida | Jay Roberts E485
Apr 7, 2026
Jay Roberts, CEO of Prosper Group — a Miami developer of luxury waterfront condos. He discusses why billionaires and tech leaders are relocating to South Florida. He explains high-end waterfront site selection, underwriting big developments, presale funding structures, and why waterfront real estate keeps appreciating.
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Time And Location Trump Many Development Risks
- Time and location are the dominant project risks for luxury condo development.
- Jay lists macro factors (interest rates, international buyers, tariffs) and emphasizes picking premium waterfront sites to de-risk sales.
Venetian Islands Flip Showed Rapid Waterfront Gains
- Waterfront scarcity drives dramatic appreciation over short periods.
- Jay recounts a Venetian Islands house bought for $7M in 2019, flipped to $13M, then listed around $29M by 2024 after Miami demand surged.
Choose Markets With Fast Entitlement Timelines
- Prioritize markets with faster entitlement and developer-friendly zoning to shorten timelines.
- Jay contrasts Miami's ~12 month entitlement timeline with California's multi-year permitting that can kill deals.