Rich Conversations

Rich records from a small park in New York’s West Village, beginning with five minutes of breathing before exploring gratitude, curiosity, technology, routines, and the tension between reason and feeling. While distributing books through Little Free Libraries and photographing advertisements for his Ads in New York project, Rich reflects on the unexpected things we collect, the rules we continually break, and whether every new app or technological convenience actually improves our lives. The session closes by examining morning and nighttime routines, the value of following curiosity, and what we have to look forward to in the week ahead. From unexpected books to dive-bar conversations and a Harry Styles concert at Madison Square Garden, it’s a reflection on staying open to the information, experiences, and possibilities happening around us. Questions from this session: 1. What are we grateful for? 2. What does our environment smell like right now? What smells from our past bring back memories? 3. What books are we energized to read? What is currently on our to-be-read list? 4. What personal rule or philosophy do we know is reasonable, but continually ignore or break? And relatedly, are we leaning more toward our head or our heart right now? 5. What is a recent app we downloaded, and why did we download it? What problem is it solving, what are we hoping to gain, and is it worth the additional data, information, and friction it introduces? 6. What is something in our recent use of technology that worked really well? What is something that didn’t work well? 7. What does our morning routine look like right now? Is it effective? Do we enjoy it? What would we change? 8. What does our nighttime routine look like? How well have we been executing it? 9. What are we curious about this week? 10. What are we energized for in the next week?

In this Rich Reflections session, Rich steps into the energy of New York City for an experiment in presence: can you find stillness in one of the most stimulating places in the world? Recording from a park near Hudson Yards, Rich begins with five minutes of breathing before moving through a series of questions designed to create greater clarity about our lives. Against the sounds and movement of Manhattan, he reflects on gratitude, observation, curiosity, hope, travel, and the seemingly insignificant details that can reveal something larger about ourselves and the world around us. Recorded on the 25th anniversary of September 11th, Rich remembers experiencing the attacks as a seventh grader in rural Wisconsin and considers how his perspective has changed over time. He reflects on the sense of national unity he remembers from the aftermath and asks listeners to consider their own memories—or, for younger listeners, what September 11th means to them today. From there, the session follows curiosity wherever it leads: Thomas Jefferson, the history of coffee, walking through New York, travel, and Rich’s new Ads in New York book project. He explores advertising as a cultural time capsule and considers the value of becoming a better observer—noticing the overlooked details that tell us something about the larger human story. This is an episode about getting out of our heads and back into the world. What gives us hope? When do we feel completely present? What obscure interests make us who we are? And what are we genuinely excited to experience next? Because if you can sit still, breathe, and reflect in New York City, maybe you can do it anywhere. Questions in this session: 1. What are we grateful for? 2. Where were we on September 11th, 2001? What do we think about it now? If you weren’t born or don’t remember it, what stands out to you about September 11th culturally, societally, or in relation to your family? 3. What—or who—have we been curious about learning about lately? 4. What is something most people would consider uninteresting that you find interesting? 5. What place would we like to experience next? What’s next on our travel or curiosity list—even if we experience it through film, YouTube, or learning rather than physically traveling? 6. When was the last time we felt completely present? 7. What gives us hope? 8. What is a small nuance in our life that others wouldn’t know about, but that is personally meaningful to us? 9. What are we curious about recently? 10. What are we energized for in the next week?

Rich reconnects with Timothy Hayden in Los Angeles for a wide-ranging morning conversation about work, discipline, freedom, gratitude, and what it actually means to improve yourself. Timothy shares what he’s learning from his new job delivering for FedEx—from navigating unfamiliar streets and physically demanding days to discovering how quickly repetition can turn confusion into instinct. The experience has also pushed him to think more seriously about nutrition, exercise, recovery, and taking care of his body. The conversation moves into Timothy’s life after incarceration and his desire to find the right balance between enjoying his freedom and remaining committed to the habits that helped shape his future. After nights at the beach, rock climbing, seeing friends, and simply experiencing life again, Timothy reflects on his need to recenter himself around reading, writing, learning, and building toward a larger mission. Rich and Timothy also explore the extraordinary comforts of modern life. Reading classic literature has made Rich increasingly conscious of how commonplace disease and premature death once were, while Timothy compares that history with experiences of cold showers and limited resources in prison. Together, they consider whether modern comfort has made us less resilient—and how much of everyday life we simply forget to appreciate. The episode closes with a spirited debate about David Goggins, physical endurance, excellence, and why we push ourselves in the first place. Is becoming stronger an end in itself, or should self-improvement ultimately enable us to contribute something greater to other people and society? From rock climbing one step at a time to pushing the limits of mind and body, this is a conversation about freedom, resilience, gratitude—and making sure personal growth has somewhere meaningful to go.

Rich Reflections returns around a campfire. After spending more time than he’d like in front of a computer, Rich heads outside, lights a fire, and creates space to breathe, think, and reconnect. Beginning with five minutes of intentional breathing, this session explores where we are right now—and where we might want to go next. Rich reflects on the prevalence of self-doubt and anxiety he noticed during a recent trip to New York and asks how we can better understand our own relationship with uncertainty. From there, the conversation moves into gratitude—not only for what we have today, but for the decisions and work of our former selves that made our present lives possible. Around the fire, Rich considers what history can teach us, drawing inspiration from the unusual devotion and independence of the Carthusian monks. He explores his own “full throttle or idle” approach to life, reflects on the summer that is coming to an end, and shares his excitement surrounding Blue Byron Books and the expanding Gate of Clouds universe. The episode ultimately turns outward: How can we participate more in the world? How can we be useful to the people and communities around us? And instead of waiting for some distant transformation, what is one action we can take today to make life better? A reflection on stillness and action, solitude and participation, gratitude and growth—and the value of occasionally sitting beside a fire and thinking about what it means to be alive. Questions in this session: How are we feeling right now? What is our relationship with self-doubt right now? What are we grateful for? What are we grateful our former self did for us? What source from history can we draw inspiration from right now? When are we at our very best? What kind of lifestyle and approach to living brings that out of us? How did our summer go? Was it everything we hoped it would be? What’s coming up that energizes us? What project is really energizing us right now? What are we curious about recently? What would participating more in the world and our community look like for us? How can we be of service to others? What is one action we can take today that will make our life better and move us in a positive direction?

Recored in May 2026, in this Rich Reflections session of Rich Conversations, Rich takes us into the tractor cab during planting season in rural Wisconsin for a conversation about growth, acceptance, collaboration, and living with intention. After beginning with breathing, Rich looks at how life has changed from 2025 to 2026—from a year dominated by individual creation and isolation to one centered on collaboration and collective creation. He reflects on New Year’s resolutions, the importance of having something ahead of us to look forward to, and his upcoming trip to Miami as an opportunity to step away, zoom out, and see what might reveal itself. Along the way, Rich considers a different approach to self-improvement: instead of constantly trying to eliminate our flaws, what if we better understood and accepted our individual nature? He explores finding joy through awareness, appreciating where we exist in the long continuum of human history, examining the media and creativity we consume, and asking what becomes possible when we work with other people toward something larger than ourselves. The session ultimately turns toward curiosity and letting go. Sometimes progress doesn't require adding another task, ambition, or responsibility. Sometimes we gain more by doing less. And when we don't know where to go next, there is a simple compass: follow your curiosity. Questions from this session: What has been the difference between 2025 and 2026 in your life? What has been the biggest change or takeaway you've noticed? If you made a New Year’s resolution, how are you doing with it? What is something you’re energized for coming up? What are some of your flaws, nuances, or quirks that others might see as things to change—but may simply be part of who you are? How have you found joy lately? How are you consuming creativity and media? Do you notice any patterns? What bigger things could you achieve for yourself or your community if you collaborated and worked more with others? What are you curious about recently? What is something you could let go of that would benefit you dramatically—emotionally, spiritually, or materially? What does letting go look like to you? What are you energized for in the next week?