Rich Conversations

448. Becoming the Most Prolific Music Artist of the 21st Century

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 — attending shows, going on tour, filming studio sessions, and watching friends grow from small gigs to world tours — he left Chicago to experience a creative retreat in rural Wisconsin.

Rich uses long planting and harvesting days on the tractor to dive into audiobooks, podcasts, and full discographies. But even with Spotify’s recommendations, nothing matched the sound he was searching for. He felt disengaged with and uninspired by music. That turning point led him to experiment with AI, resulting in a surprising breakthrough: an album that finally captured exactly what he wanted to hear.

Rich walks through how that moment expanded into a massive creative process — building entire musical universes through characters from his unpublished novel, The Gate of Clouds, merging his philosophy, his experiences, and different musical styles. Music became his space of joy, reflection, and acceptance, ultimately making him happier than he had been in years. Rich also discusses founding Blue Byron Books, developing his own publishing workflow, and how his time between rural Wisconsin and Chicago helped shape his perspective on art, culture, and innovation. He describes why he believes the traditional music industry model is outdated, why artists should push boundaries fearlessly, and how his own process — built on velocity, imagination, and minimal friction — allowed him to create so much, so quickly. This recording documents Rich’s full creative evolution: from Chicago’s music scene, to the quiet fields of Wisconsin, to becoming the most prolific music artist of the century through pure experimentation, curiosity, and unconventional thinking.

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Music on Spotify

Music on Apple Music

Music YouTube

447. Culture that Shaped Modern America, Education, and Book Talk with Timothy Hayden II

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 to the books that reshaped Timothy’s life in prison—including As a Man Thinketh and The Count of Monte Cristo—this conversation blends philosophy, practicality, and personal growth. Together, they also begin discussing their next collaborative book, Two Views, One Vision: Mind & Consciousness. It’s a reflective dialogue about awareness, purpose, and the courage to build a new way of thinking in a changing world.

Timothy on Instagram: https://www.instagram.com/__timmay3/

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446. Cousin Frank on Navigating Modern Life, Loneliness, Smartphones, and Society

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 culture, and the quiet wisdom of “old timers.” From reflections on family and legacy to the loneliness of modern life, this episode blends humor, honesty, and philosophy in equal measure. Recorded by lantern light, it’s a reminder that the best conversations don’t need polish—they just need presence.

445. Rich Reflections 80: Fueling Curiosity and Creative Energy

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 unexpected recommendations of ChatGPT—using them as jumping-off points to ask what books, habits, and thoughts expand our own perspective. With humor, grounded philosophy, and a farmer’s eye for clarity, this session encourages you to ask: what’s worth my energy, and how am I choosing to feed my mind?

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Questions from this session:

1. What are we grateful for?
2. What is a time of day or environment that makes us feel good and empowered?
3. What is something we could benefit from getting clearer on?
4. What are our observations with caffeine?
5. What is our consumption of audio like?
6. What have our dreams been lately? What’s our interpretation?
7. What are 3 books that we could read to expand our perspective most?
8. What are we energized for?
9. What thoughts or habits are we practicing lately?
10. How will we pursue our curiosity in the next week?

444. Rich Reflections 79: Clarity, Curiosity & the Nature of What We Resist

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 years, and his creative relationship with Paris—from coasters and cultural appreciation to asset-gathering for future art. Rich also discusses procrastination, the depth behind our dislikes, and the distinction between speed and velocity. With quiet observations about nature, honest self-reflection, and exciting updates on new book releases, this session is a grounded and expansive meditation on doing the work, following your curiosity, and leaning into the things we often resist.

As always, the session ends with a powerful reminder: clarity fuels velocity.

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Questions from this session:

1. What are we grateful for?

2. What’s a relationship we have that would surprise someone?

3. What is a goal we have? What is an obstacle to advance?

4. How would we analyze our personality?

5. What are our greatest skills?

6. What music are we listening to lately?

7. What skill surprised us?

8. What items do we intentionally have placed in our space to frame our mindset?

9. In our time, what is an invention we appreciate exists?

10. What’s something we have been putting off that we could do right now?

11. What are we energized for in the next week?

443. Timothy Hayden II on Discipline, Direction & Doing the Work: The Real Journey of Self-Growth

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 behind meaningful work.

Timothy shares powerful insights on post-prison growth, the discipline of writing, the cost of true ambition, and the loneliness that can come with choosing purpose over comfort. The duo also dive into ego, curiosity, inner critics, and the importance of not just dreaming—but doing. From Friday nights in the gym to Phil Jackson’s lessons on egoless leadership, this is a raw and real episode about building legacy one decision at a time.

Together, they begin shaping Book Three—inviting listeners into their creation process and revealing how deep reflection fuels deep creation.

Timothy on Instagram: https://www.instagram.com/__timmay3/

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442. Rich Reflections 78: Doing Things Differently: Posture, Purpose & the Power of Clear Direction

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 experimenting with TikTok, balancing tangible and intangible work, and the importance of social alignment—asking us to examine who we allow to influence our lives. The conversation touches on design, French jazz, personal growth, and even the philosophical roots of what we hate—and why leaning into it might lead us somewhere powerful.

A timely reminder that clarity leads to velocity—and sometimes the path forward starts by doing the opposite of what’s no longer working.

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Questions from this session:

1. What're we grateful for?

2. How's our posture?

3. What's something we acknowledge about our self that's not a strength?

4. What should we be doing differently?

5. What could we be clearer on?

6. What've we been doing for movement and exercise, helping our body?

7. Who are the five people we allow our self to be influenced by most?

8. If we were to prescribe a habit for our self over the long term, what would it be?

9. What do we hate? Explore that.

10. What're we curious about recently?

11. What're we energized for in the next week?

441. Mariana Narváez on Mexico City, Creativity, Writing from the Heart, and Living With Intention

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 app, how she crafts children’s books inspired by her nieces, and how therapy shaped her ability to embrace authenticity in her art and life. We explore the differences between being a writer and becoming an author, the value of critique, and why good stories often come from bad decisions.

It’s a thoughtful and inspiring conversation on expression, growth, and creating art that lasts.

Recorded in Mexico City 25.04.01

Mariana on Instagram

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440. Rich Reflections 77: Learning Curves, Digital Shifts & the Art of Reframing Hard Things

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, reframing resistance, and inspiring the future—one deep breath at a time.

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Questions from this session:

1. What're we grateful for?

2. What phone did we like the most?

3. What patterns have we been noticing in conversations?

4. What's a learning curve recently?

5. What's a word to remove from our vocabulary?

6. What've we observed from animals in nature recently?

7. What're we looking forward to this fall?

8. What's our least favorite season?

9. What do we consider art that others would not?

11. What was our favorite social interaction recently?

12. What's something hard we can reframe as easy?

13. What're we energized for in the next week?

439. Alejandra Carreño on Photography, Presence, and the Electric Soul of Mexico City

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 the best photos are born from presence, not perfection.

They also discuss life in Mexico City: its creative energy, street markets, food culture, community spirit, and unique rhythm of daily life. The conversation flows through travel, music (Afrohouse to French disco), digital connection, dating apps, and Alejandra’s curiosity about her own evolving future.

This is an uplifting episode about artistry, awareness, and saying yes to life.

Alejandra on Instagram