Episodes

What’s the worst that could happen? For Rob Katz and Kevin Boehm, a four-hour conversation over coffee turned that question into the beginning of Boka Restaurant Group. This week, Rachel and Jeana welcome restaurateur Rob Katz for his first podcast interview—and a candid, funny conversation about taking chances, building trust, and making people feel seen. From arriving in Chicago with $1,200 to discovering hospitality during an unexpected bartending shift, Rob shares how relationships shaped h...

A diploma doesn’t come with instructions for making friends, navigating workplace expectations, or walking into a room full of strangers. So where do we learn those things? This week, Rachel and Jeana welcome Heather Redisch, creator of Adulting 101 Masterclass, for a conversation about building confidence and connection through the everyday experiences that stretch us. Heather shares what she’s learning from coaching Gen Z, why managers should say the unwritten rules out loud, and how parents ...

What’s the difference between collecting contacts and building real relationships? Award-winning communications executive—and lifelong super-connector—Jon Harris joins us to share what more than three decades of bringing people together has taught him about curiosity, generosity and the relationships that remain long after jobs and titles change. Jon opens up about the difficult childhood that shaped his commitment to helping others, why he believes the best networkers give without keeping sco...

What does it mean to love a place deeply and know when it’s time to leave? New York Times bestselling author and Pulitzer Prize finalist Xochitl Gonzalez joins Jeana and Rachel for an expansive conversation about the places that make us, the people who remember our earlier selves, and the courage it takes to enter a new chapter. Xochitl reflects on Brooklyn as both a hometown and a living archive. She also talks about writing Last Night in Brooklyn as one final love letter to the place that sh...

People-pleasing can look like kindness—but is it actually bringing us closer to one another? In this episode, Rachel and Jeana examine how people-pleasing shows up at work, in friendships, in romantic relationships and even in hospitality. Inspired by Adam Grant’s writing on the subject, they explore the fear of disappointing others, why saying no can feel so loaded and how trying to earn someone’s approval can create an “authenticity gap” in the very relationships we’re hoping to strengthen. ...

What if the goal of a disagreement wasn’t to win, but to make the next conversation possible? Rachel and Jeana talk with Harvard professor Julia Minson, author of How to Disagree Better, about what happens when we assume we already understand the other person. Julia shares a late-night disagreement with her daughter that went sideways, why curiosity needs to be spoken aloud, and a simple “curiosity sandwich” for expressing your view while staying open to someone else’s. They also explore why p...

What happens when kids put down their phones and have the freedom to simply be kids? Rachel and Jeana sit down with Tommy Hoffman, executive director of Herzl Camp, to explore why summer camp remains one of the rare places where young people can practice the art of conversation, navigate conflict, develop independence, and form meaningful friendships through repeated, real-life experiences. Tommy shares how returning to camp after a 30-year career helped him find his “A+” calling—and what he h...

We’re back for Season 3—and after 50 episodes of talking about friendship, connection and the relationships that make life better, we’ve learned a few things. In this season opener, Rachel and Jeana look back at the conversations from Season 2 that have stayed with them, changed their behavior and even sparked new friendships in real life. They talk about why friendship can feel harder in adulthood, the invisible work of being the person who always makes the plans, the vulnerability of feeling ...