Travel is in a weird place. What better time to look back to see how we got here—and where we might go?

Each episode, travel industry veterans Brian and Kaleena discuss the big and small moments in travel history that led us to where we are today. Some moments completely rewrote the rules—like the invention of jumbo jets. But we’ll also discuss moments that reflect ongoing trends in travel, like how Disney changed Orlando.

In our discussions, we’ll explore how these examples might inform our current state of travel, and the challenges ahead. We’ll talk about ever...