Episode 365 features Jon Cativerra, the founder and songwriter of Time Spent Driving, an indie rock band whose emotive, heartfelt sound helped define the early 2000s emo and indie scene. He is also the Founder, CEO, and Creative Director of Sleepless Media, a full-service creative agency he launched in 2003. For nearly 25 years, Jon has balanced life as a working musician and agency leader. Proving that creativity and professional success don’t have to come at the expense of one another. In this episode, he shares honest insights on resilience, time management, creative burnout, and what it really takes to sustain both passions. Whether you’re a musician building a career, an entrepreneur with creative ambitions, or someone trying to balance work with passion projects, this conversation is packed with practical wisdom and inspiration. Tune in as Jon shares stories from the road, lessons from building Sleepless Media, and how he continues to stay driven in both worlds. This episode also features the track “Sleep and Matchbooks,” available wherever you listen to music. Thanks for listening and supporting local artists.