#46. Quinntessential Questions with Rai Kannu: Finding Freedom In Reinvention
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In this inspiring episode of The Quinntessential Questions Podcast, Paul Quinn speaks with Rai Kannu — PE teacher turned performing artist, Mediacorp radio DJ, entrepreneur, and restaurateur — whose journey is a masterclass in passion, resilience, and reinvention.
Rai began his career teaching and studying at Raffles Institution, before taking a leap of faith into the performing arts. That one-year sabbatical turned into a life-changing career pivot, where he transformed his love for music, storytelling, and performance into a livelihood.
Today, Rai is a familiar voice on Class 95FM, where he has worked alongside some of Singapore’s most recognised DJs, including Jean Danker and Yasminne Cheng. Beyond the mic, he has built a reputation in theatre, music, and business — opening his own restaurant, The Flying Squirrel, while balancing the demands of live radio and the creative industry.
We dive into:
His transition from teaching to the performing arts
The challenges of consistency, naysayers, and creative fatigue
The impact of Covid-19 on his career and performances
Life as a Mediacorp radio DJ & the transition to live radio
Building a personal brand, support system, and entrepreneurial journey
Memorable performances, mentorship, and the emotional power of music
If you’re curious about career reinvention, Singapore’s radio scene, or the mindset it takes to thrive in the creative industry, this episode is for you.
Guest Bio
Rai Kannu is a DJ at English Radio Station, Class95. With a multifaceted career in entertainment, he is known for being one half of music duo, Jack & Rai, performing for over two decades, gracing both local and international stages. The duo has also written songs for several English drama series, including the Apollo Award winning theme song for long running drama Tanglin.
Minutes
(02:05) Introduction
(05:32) Becoming a PE Teacher (07:04) One Year Sabbatical (08:14) Performing Arts
(10:24) Turning His Passion to a Living
(11:53) Dealing with Naysayers (14:31) Consistency & Stability (16:47) Challenges Faced
(21:10) Impact of Covid-19
(24:45) Most Memorable Performances
(25:45) Becoming a Radio DJ (30:30) Support Structure
(34:05) Transition to Live Radio (38:33) Seeking Mentorship (39:33) Learnings from Different People
(40:57) Reading Books
(45:45) Interviews as Conversations
(47:47) The Impact of Music (52:39) Music, Emotions & Nostalgia
(54:24) Becoming a Restaurateur (58:05) Personal Branding
(58:45) Key Pivotal Moments (01:01:38) Creative Fatigue (01:03:27) Advice for Young Adults & Parents
(01:07:12) Rapid Fire QuestionsBehind-The-Scenes
