Reboot Podcast Episode #177 – What Does It Mean To End Well? – with Randy Goodman

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

#177 // May 22, 2025

Guests

Randy Goodman

Randy Goodman

Former Chairman & CEO of Sony Music Nashville

View Bio

Episode Description

How do we navigate seismic shifts in our industries and our lives while striving to remain true to ourselves and those we care about? In this episode, Jerry sits down with Randy Goodman, recently retired Chairman and CEO of Sony Music Nashville, to reflect on a career arc that spans decades of change, challenge, and profound personal growth. Randy opens up about his time at the helm of Sony Music Nashville, leading through a rapidly transforming business landscape, the global pandemic, and the social upheaval of recent years.

Together, Jerry and Randy explore the concept of “ending well,” and what it means to finish a significant chapter of one’s life with intention, care, and grace. The conversation wades through the joys and trials of artist development in an era defined by digital disruption, the decline of traditional radio, and the emergence of platforms like TikTok. Randy shares how he shepherded his team and roster of artists through extraordinary circumstances, and how executive coaching and a sense of curiosity became his compass in uncertain times.

 

Show Highlights

Memorable Quotes:

“I always told myself if I don’t mess up too badly, hopefully I’ll get to end my career in this interesting arc, this circle. I’m going to get to end my career in one manner of speaking where I started it. And that was terribly compelling to me.” – Randy Goodman

“From the very get go, it was about having this strong team and then immediately trying to empower the people that were there to say, look, we have to tear down these silos. You’ve got to get out of your foxholes, and we’ve got to all start running as fast as we can towards these artist development goals. And we’ve got to be doing it together.” – Randy Goodman

“I think having you help me in the way that you were doing as my executive coach, but more this kind of confidant and someone to brainstorm with, that really helped me to go into this seismic, these seismic changes, I think with more open-mindedness.”- Randy Goodman

“I’ve never really thought about having an executive coach because the only people in my experience working at a record company who had executive coaches… If you had an executive coach, that meant that HR came to you and said, you’ve done something so bad, the only way you’re gonna be able to keep your job is we’re going to get you an executive coach. And it’s like going to rehab, and then you come out of rehab, and you’ve made all things right. You’ve covered a multitude of sins and you can come back into the fold.” – Randy Goodman

“You were the one that were constantly holding me accountable. You would say, What was your mission? What did you tell me? What do you wanna do? How does that fit? And so you were constantly in these moments. I guess, bringing my view up to more of a macro level.” – Randy Goodman

“You became my executive coach and then became my therapist and then you became a dear friend.” – Randy Goodman