TIMELESS with Teddy Abrokwa
Timeless with Teddy is a podcast exploring the minds, journeys and philosophies of builders, creatives and cultural leaders.
Hosted by Teddy Abrokwa, each episode goes beyond surface-level conversation to uncover the decisions, discipline and defining moments behind success.
From music and media to business and leadership, Timeless is a space for meaningful conversations that outlive the moment.
New episodes feature founders, artists, executives and thinkers shaping culture and industry across the UK and beyond.
If you’re building something, becoming something, or searching for clarity - this is for you.
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TIMELESS with Teddy Abrokwa
OSH — Musician | Life changed with one freestyle
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Sometimes one moment changes everything.
In this episode of TIMELESS with Teddy, South London singer and rapper Osh This Side — born O’Shea McDonald — reflects on the journey that shaped both the artist and the man behind the music.
Raised in Norbury with Jamaican and Cuban roots, Osh’s musical foundation began in the church choir, where he developed his voice while learning to play the piano and violin. From there, his path took a surprising turn — leaving a graduate training role at Enterprise Rent-A-Car to pursue music fully.
His breakthrough moment came after a freestyle over Ye by Burna Boy, which quickly went viral and introduced his talent to a wider audience. But beyond the viral moment, Osh speaks about preparation, discipline and staying grounded while building a career in music.
The conversation also moves into more personal territory, as he shares the impact of losing his father during the COVID-19 pandemic and the responsibility he felt to step up and support his family.
The episode closes with a powerful, spontaneous gospel performance from Osh alongside DJ Skaps on the keys — a reminder of the roots that shaped his sound and spirit.
A conversation about faith, loss, resilience and the journey behind the music.
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