The Class of 2001... 25 Years Later. We grew up before constant connectivity. We built careers during economic instability and cultural change. Now we are navigating midlife with aging parents, growing children, and a sharper awareness that time is finite. You may know us as Gen X, Xennials, Millennials. We talk about about burnout, reinvention, parenting, ambition, and what responsibility looks like in midlife. We thought adulthood was the destination. It turns out it's only a stop along the way.
We'll bring the honest conversation. You bring the mixtape.
It’s Been Longer Than I Thought
Mayuri Chandra and I have known each other since we were kids. This year marks 25 years since we graduated from college in 2001. We talk about what that milestone actually feels like. The doctor who’s younger than you. The version of you that still feels 25, even when the mirror disagrees. The way old friends collapse time. We revisit the New York we imagined in our twenties, shaped by Rent and Sex and the City, and what it was like to arrive in New York City in 2001. That October, Mayuri started at the Public Art Fund, presenting contemporary art in public space in a city still processing 9/11. From there, we talk about nonprofit leadership, burnout in arts organizations, and the hard lesson that good work does not automatically mean good management. We end with reflecting on what it’s like to grow up before constant connectivity, the beauty of silence and longing, as well as what it takes to sustain a creative practice.
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.
The Dream Can Change
I reconnect with Sunil Ayyagari, someone I’ve known since we were kids, to talk about identity, ambition, and the unexpected turns adulthood can take. Sunil reflects on growing up queer in the late 80s and 90s, when stigma and fear shaped what was visible, and how early cultural touchstones helped him build a sense of self. He shares what it was like to build a career in theater, realize the dream had limits, and reset in his early thirties through business school, a new career path, and a new life chapter that includes marriage and a move back to North Jersey. We also talk about attention and technology, what we miss about mixtapes and appointment TV, and what it means to come of age before constant connectivity, then learn how to live with it anyway.
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.
Live As You’re Going
Kahwa Douoguih 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.
Nobody Gets a Playbook
Jeff Gurtman and I have known each other since nursery school, when we were already trying to sell “pencils” made out of sticks. This year marks 25 years since we graduated from college in 2001. We talk about what that era felt like. The pressure to land one of the “good jobs.” Consulting. Finance. Real estate. The subtle message that there was a right path, and that deviation required explanation. We revisit that moment with more distance now. The myth that adulthood comes with answers. The realization that you can hit every milestone and still feel like you are figuring it out in real time. From there, the conversation widens. Technology and boundaries. Jeff teaches me what the GS in Apple IIGS stands for. We trade notes on all things cassette tape design. He makes a convincing case for Carmen San Diego vs. Oregon Trail. Time as a luxury. Parenting. Friendship. And finally, Jeff’s line that has stayed with me: designing a life so that he can have a sidewalk that goes somewhere.