High School Matters

Mr. Dubin was one of my favorite teachers in high school, not because he stuck to any script, but because he had his own style. He was quirky, unpredictable, and full of spirit. His class felt fun, personal, and the kind of experience that stays with you for life.

In this episode, we look back on what made him so memorable, like the way he connected with students, his creative traditions, and his legendary "bust outs". The most surprising part? He somehow remembered stories about me from over 30 years ago — in crazy detail!

I never set out to copy him, but my classrooms today are like his used to be. The tone, the energy, and the way I try to make things feel fun and real for my students are all a result of his influence.

In a refreshing twist from my usual conversations with former students, this episode features one of my closest friends from high school, Kenny Eisenstein. Back in 1994, Kenny's dry, understated humor kept me laughing—and it still does. Like many of us, Kenny looks back on high school with a mix of nostalgia and a few regrets. But overall, he remembers it as one of the best times of his life. What's especially fascinating is hearing which parts of that teenage world he still wishes he could carry into adulthood. Kenny has always been a thinker with a deep love for the arts, particularly music. He's the one who first introduced me to my favorite band, Pearl Jam—a moment that shaped much of our early friendship. Now a film professor at Bucknell University, Kenny reflects on whether adulthood has lived up to those high school years. Did he peak in high school? What lessons from that time still guide him today?

Richie Kamen's journey is nothing short of extraordinary. Richie went from a poor, insecure, bedwetting kid to the unlikely owner of Camps Equinunk and Blue Ridge, which he somehow purchased with no money and zero entrepreneurial experience. But owning the camps was only the beginning. Richie faced fierce protests and resistance while working to modernize the camps, tackle long-standing challenges, and improve a shocking culture of bad behavior. Against "one-in-a-million odds," Richie transformed these camps into two of the most beloved sleep-away destinations in America, creating a nurturing environment for young campers while finding fulfillment beyond his wildest dreams—both financially and spiritually. Don't miss this inspiring tale of Richie Kamen.

Aaron Bours, the student who dropped out of college to become a soldier in the Israeli Defense Force, has returned to speak with me again. This time he is a wounded hero at the center of the world's most divisive war between Israel and Hamas. Hear about the conflict as he experienced it firsthand, how that experience changed him forever, and how he barely made it back alive!

Aaron Bours thrived in high school and got the most out of each day there. After graduating, he wanted to be more than just a college student, so he dropped out of college to join the Israeli Defense Force. This experience changed his life. After settling into a successful and stable career, he decided to come out of the reserves to return to the IDF to fight for his country. This conversation felt fun and lighthearted back when we had it, but has become ever relevant today.

After recording this emotional and revealing conversation, my guest asked me to protect his identity so his name will not be used. My guest entered Great Neck North High School as a 10th grader after being kicked out of a Yeshiva. His risky behavior got him kicked out of GNNHS also, this time for punching another student and sending him to the hospital. He'd always seemed like a nice kid to me, but after hearing stories about him from different people, this conversation was my mission to truly learn about him. We talk about the punch that got him expelled, his home life, taking accountability for his choices, his feelings about education, the cycle of influential behavior and so much more. This conversation is particularly enlightening because it gives insight into a truly unique person and how people develop into themselves.

Adriana Phillips went through high school on a mission: to find herself. She often felt like her personality had two sides, but she never quite understood why. She looked like she might be a popular cheerleader or prom queen, but instead she was a studious actress. Adriana was driven by this ambiguity. She always questioned and embraced why she felt certain ways. We talk about her struggle in my class, her struggle with boys, and her struggle with her own sexuality. To this day I remember my first moment with Adriana. What I didn't realize was how much that moment symbolized exactly who Adriana was back in high school.

Leila Eshaghpour and Julia Eshaghpour are identical twins. They were both in my AP Chemistry class together back in 2016. They are hilarious, self-reflective, genuine, and unique young women. We talk about what each of their lives has been like growing up with a mirror image of herself. We dive into topics that identical twins have unique insight into, like comparisons, jealousy, boy drama, separation anxiety, and so much more. Things got emotional when we spoke about when one of their friends—who was also a twin—passed away tragically, and how that impacted their outlooks ever since. The spirit of the trialogue flowed perfectly between fun and light to emotional and authentic. This conversation will teach you a lot of the nuances of what it's like to be a twin, and by the time you're done listening, you'll realize it put a huge smile on your face too!

Benny Laitman started high school as a self-described lanky, nerdy kid. He decided to run for class president in his freshman year and wound up winning. We discuss all of the events that took place because of that victory and how his life has been different ever since. We also discuss how his introduction to life as a doctor was thrown for a loop when he faced a catastrophic situation that changed everything forever. From his high school career to his medical career, he faced many small moments and some big moments that have all had a tremendous impact on his life today.