#219 - A million-dollar decision can look a lot like a random pop-up ad and a quick, messy “why not?” Alex Boylan went from being a preacher’s kid on the North Shore of Boston to winning Season 2 of The Amazing Race, and that victory didn’t just change his bank account, it rewired his definition of work, purpose, and adventure. We talk through the early travel experiences that shaped him, the real dynamics of racing with his best friend Chris, and the pressure-cooker moments where relationshi...