How to Win in Any Market Using Creative Real Estate
Chris Prefontaine recounts his early career, losing everything in the 2008 crash, and how that experience reshaped the way he approaches real estate and business. Out of that adversity came the 3 Paydays model, a creative strategy that allows investors to generate income upfront, monthly, and long-term—without relying on banks.
Derek and Chris discuss why creative financing is more important now than ever, how uncertainty in the market creates opportunity, and why ethical deal structuring matters. They also touch on the dangers of misinformation in real estate education, the importance of integrity, and how the right mindset separates long-term winners from short-term speculators.
This episode also marks a major milestone—100 episodes of Generations of Wealth—and highlights how relationships, not transactions, are the foundation of lasting success.
How to Convert Hotels into Apartments (Safely & Profitably)
Derek sits down with Ryan Sudek, CEO of Sage Investment Group, to unpack a repeatable system for converting underperforming hotels/motels into studio apartments—filling an affordability gap while targeting strong returns.
They cover market selection, underwriting, construction (sprinklers, sub-panels, kitchens), property management at 100–200 unit scale, and the capital stack behind Sage’s evergreen fund (quarterly distributions, 1031 within the fund, portfolio diversification). Expect practical detail on risk controls (change-of-use permits before closing, value engineering, local code strategy), tenant quality myths (longer average tenancy than market), and why exterior-corridor assets speed construction. The episode closes with goals (10–15 conversions/year, path to 15k units) and how deals actually reach the team (direct-to-seller, lenders, brokers, 60–70 LOIs out at any time).