Since 2014, Neil Vogel has led the transition of About.com into Dotdash. Under his stewardship, the IAC-owned company has gone from an all-things-to-all-people approach to a publisher of discrete, focused verticals including Verywell (health), the Spruce (home), Lifewire (tech), the Balance (personal finance), Tripsavvy (travel) and Thought Co. (life hacking). We discuss the challenges and opportunities of that transformation – but first he talks about the life-changing experience, early in his career, when he hit the road for a year with the sole intent of getting bored. We also dig into his time at the Webby Awards, which he had a hand in founding and making the cultural touchstone it is today.