In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien are joined by Justin Avey for a different kind of conversation—breaking down the good deals and the bad deals that shaped their careers.

Instead of focusing on a single project or business, the three dive into the real stories behind some of the biggest wins and toughest lessons they’ve experienced in real estate and development. From projects that turned into unexpected successes to deals that dragged on for years with setbacks, contractors, and surprises, nothing is off the table.

Keith shares the story of a South Hill project that became a long, stressful journey before finally turning around. Jordan reflects on the ups and downs of redevelopment and large-scale projects, while Justin brings his own perspective from the construction side of the business.

Good Deal / Bad Deal is an honest look at what it really takes to stay in the game. Behind every successful investor are the deals that nearly broke them—and the ones that made it all worth it.