Rich Conversations

Rich takes us into the soybean fields of rural Wisconsin during autumn harvest season. Recording from the combine on a beautiful October afternoon, he begins with five minutes of breathing before exploring gratitude, seasonal traditions, and the satisfaction that comes from working toward something with focus and purpose. From viewing farming as a form of agricultural art to finding clarity during...

Rich explores gratitude, personal identity, creativity, and the importance of making deliberate choices that bring greater meaning to everyday life. Beginning with five minutes of breathing, he celebrates the Milwaukee Brewers' World Series excitement before reflecting on personal aesthetics, simplifying decisions, and appreciating the small details that make life beautiful. From finding a flow st...

Rich returns to his farmhouse studio in rural Wisconsin to explore the power of clarity, intentional living, and understanding what we truly want from life. Beginning with five minutes of breathing, he reflects on gratitude, personal aesthetics, and how knowing ourselves better can simplify decisions and bring greater purpose to our everyday actions. From vintage furniture and the latest Rich Edit...

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 continuall...

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 M...

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 expe...

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 d...

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...

Recorded on New Year’s Eve, this Rich Reflections session is a deep, intentional pause between 2025 and 2026. Rich begins with five minutes of guided breathing before reflecting on an unprecedented year of creative output—48 books and 64 music albums—and what that level of execution reveals about fundamentals, clarity, and focus. Through a series of thoughtful questions, he explores energy, alignm...

Rich shares how he became the Most Prolific Music Artist of the 21st Century, releasing over 50 albums and 800+ original songs in under six months — an unprecedented achievement that unfolded almost by accident. Rich explains the frustration that sparked it: today’s artists spend more time on image and branding than on actually making music. After 15 years immersed in Chicago’s live music scene —...

In this episode, Rich reconnects with Timothy Hayden for a grounded, wide-ranging conversation about discipline, education, and the culture shaping modern America. The two discuss daily habits like journaling and meditation, how discipline creates freedom, and why overthinking is the silent struggle of our time. From reflections on “cookie cutter America” and the emptiness of profit-driven culture...

In this unfiltered episode of Rich Conversations, Rich sits down with Cousin Frank in the farm shed for a raw, late-night talk about life, purpose, and what it means to live well. The two dive into perfectionism—when it helps, when it holds us back—and how society’s obsession with comfort and convenience has dulled our sense of purpose. They explore topics like smartphones, discipline, consumer cu...

In this Rich Reflections session, Rich invites listeners into an early-morning meditation on curiosity, creativity, and energy. From candlelit writing at 3:42 a.m. to reflections on caffeine habits among history’s greatest minds, the episode explores how we fuel our bodies and minds for the work that matters most. Rich shares insights from The Hero with a Thousand Faces, The Tao Te Ching, and the...

In this Rich Reflections session, Rich explores everything from spider webs and wild hawks to the power of publishing and the politics of personal bias. Set against the rhythms of farm life and the coming harvest season, the episode invites us to examine our patterns—what we avoid, what we collect, and what we truly value. He reflects on designing books, learning tools like InDesign over the past...

In this moving and energizing episode of Rich Conversations, Rich is joined once again by co-author Timothy Hayden II as they reflect on their journey co-creating their four-book philosophy series, Two Views, One Vision. With Book Two now published, they open up about what it means to live with intention—through strict routines, evolving relationships, personal milestones, and the quiet grind behi...

In this Rich Reflections session, Rich invites us into a moment of stillness and clarity as he reflects on life, habits, and creative flow. From tidying cluttered drawers and adjusting posture, to navigating the challenges of digital growth and the beauty of September walks in the woods—this episode is about making small shifts that ripple into greater clarity and momentum. He opens up about exper...

In this episode of Rich Conversations, we sit down with novelist and children’s book author Mariana Narváez in the heart of Mexico City. We talk about what makes the city so magical—from jacaranda trees to its thriving café culture—before diving into Mariana’s creative journey. She shares how heartbreak led her from anonymous Instagram poetry posts to writing a 300-page novel in her iPhone notes a...

With curiosity as a compass, Rich invites listeners to examine the words we use (like “try” vs. “do”), the devices we hold, and the animals we observe. He reflects on treating everyday tasks—like mowing the lawn or adjusting to seasonal change—as forms of art, and ends with a call to experiment: What if the things we think are hard… are actually easy? A meditative, grounded episode on clarity, ref...

In this joyful and expansive episode of Rich Conversations, Rich sits down with Mexican photographer Alejandra Carreño in the artistic neighborhood of Coyoacán. They explore the essence of capturing human connection through photography, from weddings and portraits to personal projects with her grandmothers. Alejandra shares her philosophy on light, emotion, and waiting for the right moment—and why...

In this Rich Reflections session, Rich checks in from Chicago’s Lurie Garden on the final weekend of summer. Amid Lake Michigan air and city sounds, he explores what it means to shift seasons—mentally, emotionally, and creatively. From three espresso shots and finishing three new books for Blue Byron Books, to the importance of fundamentals, curiosity, and giving yourself the green light—this is a...

In this Rich Reflections session, we begin with intentional breathing and ease into a wide-ranging reflection on presence, momentum, and clarity. Rich shares his gratitude for creative collaborators and the evolution of relationships, celebrates the release of two new albums (Velvet & Voltage and Electric Heels), and reflects on his routine in rural Wisconsin—cutting grass, smoking a celebrato...

In this candid conversation, Timothy Hayden shares the discipline, vision, and perseverance that carried him from prison life to holding his first published book. He talks about the strict daily schedule that keeps him focused, the mental challenges of lockdowns, and the deep meaning of belonging explored in Two Views, One Vision. Timothy reflects on the power of proving doubters wrong, the lesson...

In this Rich Reflections session, Rich weaves together childhood memories, nature observations, and current creative projects to explore how inspiration sticks with us. From recalling the energy and games of playground days to noticing turkeys moving like dinosaurs on the farm, he draws connections between curiosity and creative fuel. Rich shares updates on book writing, music releases, and the ha...

In this inspiring conversation, Timothy Hayden reflects on his journey from incarceration to becoming a published author. He shares the excitement of holding his first book, the discipline and visualization practices that kept him focused, and the philosophy that drives his work today. We explore the value of time over money, the role of momentum in creative pursuits, and the mindset shift require...

In this week’s Rich Reflections, Rich invites listeners to slow down, take a breath, and recalibrate. After a whirlwind stretch of publishing 6 books and releasing 7 albums in one week, he reflects on the importance of stepping back—not to stop, but to notice. Through questions about gratitude, energy, creativity, and what you’d do with your first million, Rich explores how presence reshapes ambit...