Oct 6, 2026 · 28 min
Listen from 25:35
Listen at 25:35
Creative financing turns market setbacks into real estate opportunity
He Lost Everything in 2008 and Built It All Back | Chris Prefontaine
Chris Prefontaine’s recovery from the 2008 crash frames creative financing as a way to solve problems for sellers and buyers when conventional lending falls short.
- 1Free-and-clear properties can support seller-financed deals that create value for sellers, buyers, and investors.
- 2The Three Paydays model combines deposits, monthly payment spreads, and long-term principal collections.
- 3Chris and Justin argue that durable success requires focused strategy, cycle-tested mentors, and a definition of life beyond money.
Don't miss
Chris recounts moving from selling a valuable Newport property to a modest apartment, then describes the perspective that enabled his rebuild.
The brief
Chris Prefontaine and Justin Colby begin with the financial and emotional wreckage of 2008, then trace how those battle scars shaped a more creative approach to real estate.
Prefontaine explains why free-and-clear properties are central to his model: owner financing can solve a seller’s goal while opening a path for buyers conventional lenders reject.
His Three Paydays structure turns one terms deal into several potential revenue points through deposits, monthly payment spreads, and long-term principal collections.
The standout story is Prefontaine’s fall from selling a valuable Newport property to living in a modest apartment—and the perspective that helped him stop blaming himself.
The broader lesson is restraint: choose one strategy, learn from people who have survived multiple cycles, and measure success by family, purpose, and presence as well as money.