Conversations about leaving the expected path, redefining success, and choosing another way forward.
Taking a Fork in the Road
In this episode, I’m talking with my old friend Gene Gurkoff, founder of Charity Miles. We talk about taking the road that isn’t always straight, about purpose as something we practice rather than find, and how staying in motion can create its own kind of belonging. If you’ve ever wondered what it looks like to live a life aligned with meaning — even when you can’t see the whole map — this one’s for you.
Building a Creative Life from the Inside Out
In this episode, artists and producers, Everest Hall and Mike Russnak take us inside a shared life built, literally, from the ground up. We talk about art school, self-education, reinvention, homelessness, humor, moral courage, astrology, and the unexpected power of moving across the country with nothing but each other.
Live As You’re Going
Kahwa and I met in elementary school, at a small private school in New Jersey. On September 11, 2001, she was working at the IMF in Washington, D.C. On September 12, she bought a bed. It sounds small. It wasn’t; it was the beginning of looking at life differently. During our conversation, we talk about protecting your time. About choosing space over status as members of a generation that was trained to optimize for both. About growing up multiracial, having hair that wasn’t like our classmates. We talk about why she enjoys having Scotland as a second home, losing a parent, and what happened when she had a baby she wasn't planning for in her 40s.
I Wanted to Want It
Rory Eakin spent a summer in a suit, in an office building, knowing it wasn't right. He said no to the job, went to Cape Town to teach math, and began a series of career deviations that he says got easier with each one. In this conversation, he talks about growing up with an inherited picture of what success was supposed to look like, and what happens when you start pulling away from it. About burnout and the self-understanding it can unlock. About how hard it is to separate identity from the work you do. And about an unexpected turn: a pull toward faith and community after years of describing himself as a confident atheist.
Do the Doing
What would make you walk away from a Fortune 500 career to become an “old founder?” In this episode, I reconnect with my middle school buddy, Jon Zweifler. We talk about hitting a ceiling in your career and what happens when you realize there is no “next job” that will teach you something new. Jon shares his journey from the Fortune 500 to life as a tech founder who is building Reed AI from the ground up to turn real-world language into learnable moments for neurodivergent kids and how his personal journey inspired a platform helping children make more sense of the world around them.