Brain drain is one of the primary subjects. I'm familiar with Aaron's take on outmigration. Mr. Simes seems to share the same perspective. Bottom line, Cincinnati needs to pay more attention to talent attraction.
However, I would disagree with the characterization of the Midwest as somehow uniquely obsessed with those who leave. (Mr. Simes posited this dichotomy) It's a universal concern. Aaron does a good job of highlighting how little we know about other cities. Brain drain is almost completely divorced from good data analysis. Over the past 3 years, I've read about outmigration anxiety in Portland (Oregon), Dallas, Atlanta, Boston, New York City, Chicago, Las Vegas, San Francisco, and Denver (To name a few ironic locations).
Later in the podcast, Mr. Simes looks at the differences between Cincinnati and St. Louis. The primary concern is the lack of attendance for the Reds relative to that of the Cardinals. (Two professional baseball teams) Why is there such a large discrepancy? Answering that question requires an intimate knowledge of both markets (not to mention the respective histories of the franchises). I would suggest that the brain drain story is similarly esoteric. A comparison is possible, but one should be aware of the different contexts.