Jessica Rappaport
School Administrator
Jessica is an award-winning former journalist turned educator. She is currently serving as a school administrator at the middle school level. She previously taught high school and middle school language arts and journalism. She was part the CNN team that won a Peabody Award for its coverage of Hurricane Katrina.
122
Aug. 10, 2026
Ironic, Human-Centered, and Very Not AI wth Dr. Jessica Rappaport - PC122
Back-to-school season gets way more interesting when Jessica Rappaport returns to join the boys for a sharp, funny, and surprisingly practical showdown over AI in education, college writing, and what kids actually need to learn now. There's also a blind ranking of school supplies and you'll also find out how much Jeff knows about Spider-Man, hear Donnie and Jesse agree on something for possibly the first time in over 100 episodes, and learn what weird Google Keep notes Jesse keeps about his wife...
Guest: Jessica Rappaport
62
Nov. 2, 2020
A Lubinsky Among Us - PC062
Jesse's family joins the show to talk remote learning through many lenses.
49
April 6, 2020
The Quarantine with Jeff 'Exotic' Heil - PC049
Former journalist turned teacher turned administrator Jessica Rappaport (Jesse's wife) joins us on the show!
Guest: Jessica Rappaport