If I am asked to “walk through my resume,” where (when) should I start?

It’s really up to you and whatever you think tells the best story.  Some people start with where they grew up.  Others start with college or their first job out of college while more experienced or older individuals might start with Business School or other graduate program.  Just keep in mind that your most recent experiences are going to be more relevant so don’t get bogged down with stories of your first lemonade stand or how well you invested your Bar Mitzvah money.