The Sounds of Island Records

4 min readJun 16, 2021


On the 6th episode of The Pathway, Fred Swaniker sat down with Chris Blackwell, the founder of Island Records credited with introducing the world to reggae music and guiding the careers of artists such as Bob Marley and U2.

When Fred asked about the secret to his success, Chris responded, “I’ve been up and down so many times. . . . Sometimes things work and sometimes they don’t.” Room columnist Mike O’Brien shares his learnings from Chris’s undulating life journey in this instalment of his series, ‘Reflections on The Pathway’.

Do Something that Lifts People

Early on, Chris Blackwell wasn’t sure what he wanted to do with his life. He happily admitted that his “educational side was hopeless.” He bounced around, working for the Governor-General of Jamaica and then at a hotel renting sports equipment. In each instance, he found some success through kindness and service to others, but neither job fulfilled him, so he kept searching and trying different things.

One day (perhaps after a few beers), he had the courage to offer to help a group of musicians make a record, even though he didn’t really know what he was doing. There was never a master plan to become a music mogul; he simply pursued his passions. In his words, he “found something that was unique and different”, and thought, “Well, if I like this, perhaps other people will too.” Much like Don Gips (Episode #2 of The Pathway), Chris dedicated his life to amplifying the voices of others. The rest, as they say, is history.

Take the First Step

One of the things I enjoyed most about this episode was the juxtaposition between the questions the audience was asking (myself included) and Chris’s laissez-faire responses. As audience members, we saw a member of the Rock and Roll Hall of Fame, who founded an iconic record label; we were searching for deep insights! How do you know when you find an artist worth betting on? How would you start Island Records today? How can a young person break into the music industry?

Yet all of his responses circled back to this simple serendipity: you put yourself out there, take a risk, and see what happens. Don’t overthink it. Too often in life, we’re afraid of failure, so we never take the first step toward pursuing a passion. We never bet on ourselves and we let our dreams fade.

Let Your Passion Breed Purpose

What is also uniquely special about the path Chris Blackwell pursued is that by following his passions, he enabled artists to follow theirs. The ramifications of this kindness will have a positive impact on future generations. Chris introduced the world to artists who pushed boundaries and helped steer culture in a healthy direction, and now these artists have inspired millions of people both collectively and individually. How can we do similarly with our missions?

A Soundtrack for The Room

Music inspires us. Music provokes us. Music helps us truly see and understand ourselves.

While these may not be the most famous Island Record songs, if I had to select a handful of tracks which speak to the ethos of The Room and the idea of transformational leadership, this would be the playlist:

U2, “I Still Haven’t Found What I’m Looking For”

Celebrates wanting and continuing to chase your dreams…

Yusuf Cat Stevens, “Father & Son”

About a younger generation struggling to do things differently than their parents’ generation…

Julian Cope, “World, Shut Your Mouth”

Follow your passion and don’t let the world tell you who you should be…

Steve Winwood, “While You See A Chance”

The lyrics speak for themselves: “While you see a chance, take it…because it’s all on you.”

Bob Marley, “Concrete Jungle”

“No chains around my feet, but I’m not free.” None of us is ever truly free while there is still poverty and oppression around the world.

Marianne Faithfull, “As Tears Go By”

On the importance of listening to youth and living your life so you don’t have any regrets…

Now let’s take it one step further. If we were to crowdsource a soundtrack for The Room, what would you add to the playlist? Which songs and artists inspire you? What lyrics and messages do you want to help amplify around the world? I’ll start.

Alicia Keys, “Underdog”

“Keep on keeping at what you love and you’ll find that someday soon enough you will rise up…”

Big Sean, “One Man Can Change the World”

“Remember one thing: that one man could change the world.”

Kid Cudi, “Surfin’”

“I ain’t riding no waves, too busy making my own waves.” To truly make an impact we need to create and build something new; we can’t simply ride someone else’s wave.

Fugees, “Ready or Not”

To be successful we must have a little bit of swagger. If we’re going to change the world, we have to believe in ourselves.

Marvin Gaye, “What’s Going On”

“I just have to ask the question…Who really cares to save a world in despair?”

Harold Melvin & The Blue Notes, “Wake Up Everybody”

“The world won’t get no better if we just let it be. The world won’t get no better. We gotta change it, just you and me.”

Maybe there isn’t a specific message, perhaps it’s just a feeling that inspires you.

The first trumpet note Miles Davis plays on Blue in Green has haunted me (in a good way) since I first heard the song back in high school. Enjoy!

Mike O’Brien is a member of The Room and Director of Research and Investment Strategy for AVR Asset Management in San Francisco. He founded a leadership consulting firm, Independence Creek Advisors, focused on organisational dynamics and human nature.




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