Beyond the Hit: Cobi on Persistence, Grief, and the Long Road of Music

Taylor sits down with singer-songwriter Cobi for a raw and revealing conversation about what success really means as an artist—and as a human being. Cobi traces his journey from early days in Gentleman Hall, walking away from a record deal with Island Records, to finding his own voice as a solo artist. Along the way, he opens up about the pressure of chasing momentum, the grief of losing his parents, and the ways fatherhood has reshaped his priorities and sense of purpose.Together, Taylor and Cobi dismantle the myth of overnight success, showing instead how persistence, community, and mentorship shape creative lives. They talk about the freedom and challenges of going independent, the push-pull between ambition and meaning, and the deeper “why” that fuels art beyond ego or accolades. Whether you’re a musician, creator, or just someone navigating the messiness of life, this conversation is a reminder that failure only happens when you stop trying—and that showing up, even when it’s hard, is what really matters.You can find Cobi on socials @cobimusic and www.cobimusic.netIf you enjoyed this episode, please follow, subscribe, leave a review, and share with someone who might appreciate this conversation!Follow us on Socials @whothepodcareswww.whothepodcares.comTheme song by: Carl Thiel