Rich Conversations

Rich Hebron

Rich Hebron explores self-development, society & culture, art & science

  1. 26/11/2025

    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that moment expanded into a massive creative process — building entire musical universes through characters from his unpublished novel, The Gate of Clouds, merging his philosophy, his experiences, and different musical styles.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 He describes why he believes the traditional music industry model is outdated, why artists should push boundaries fearlessly, and how his own process — built on velocity, imagination, and minimal friction — allowed him to create so much,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. Subscribe to the email newsletter for inspiration, self-development, & updates: https://richhebron.com/ Music on Spotify Music on Apple Music Music YouTube

    19 min
  2. 28/09/2025

    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. Subscribe to the email newsletter for inspiration, self-development, & updates: https://richhebron.com/ Questions from this session: What are we grateful for? What’s a relationship we have that would surprise someone? What is a goal we have? What is an obstacle to advance? How would we analyze our personality? What are our greatest skills? What music are we listening to lately? What skill surprised us? What items do we intentionally have placed in our space to frame our mindset? In our time, what is an invention we appreciate exists? What’s something we have been putting off that we could do right now? What are we energized for in the next week?

    38 min
  3. 18/09/2025

    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. Subscribe to the email newsletter for inspiration, self-development, & updates: https://richhebron.com/ 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?

    37 min

About

Rich Hebron explores self-development, society & culture, art & science