Built Between Bedtimes – Episode 33: The Malarkey Family Sold for $1.3 Billion, Rob Finally Moved the McMinnville Property, and Why the Fail Flip Became the Best System-Builder

Built Between Bedtimes · Aug 21, 2026 · 33m

In this episode, Chris recaps the Portland REI Meetup with James Malarkey — grandson of the founder of Malarkey Roofing, which sold for $1.3 billion in 2022. James went from janitor to shareholder, and now he's partnering with his celebrity chef brother to buy the real estate under their restaurants — including a new steakhouse and seafood spot opening in the Pearl District. Then Rob closes the book on McMinnville: a fail flip that became a rent-to-own deal, a $25K option fee from the most committed buyer in the funnel, and a system that's now fully built and ready to scale. The property…