Rob Caplan is just one of those people with a reputation you aspire to have. It’s one of those, “You know Rob Caplan? Yeah! Love Rob!!” kind of things. He’s great.Perhaps the most notable characteristics Rob possesses are his approachability and his sense of humor. He has a way of keeping things light, not making you feel like you’re an idiot all while dropping some serious knowledge.We met in person just before WindUp San Francisco when I dropped by somewhat as a Cold Call to introduce myself, say hello, and ask if he’d ever be interested in being on the show. As fate would have it, here we are. So without further ado, here’s our conversation.