The Owners Outlook Podcast
In this powerful episode of Owners Outlook, Shaun sits down with comedian Anthony as he opens up about a life-changing year, a near-death experience in Canada, and the 10-day silent Vipassana meditation retreat that reshaped the way he views success, ego, creativity, and personal healing. Known for making people laugh, Anthony brings a deeply reflective perspective on what happens behind the performance — the pressure, the self-talk, the ambition, and the emotional cost of chasing external success. Here’s what you can expect from this episode: A Life-Changing Turning Point Anthony shares the story of nearly freezing to death in Canada after a show, the difficult season that followed, and how those events led him to Vipassana meditation. The Power of Meditation and Self-Awareness Anthony breaks down the intensity of a 10-day silent retreat, what it taught him about the mind and body, and how daily meditation has helped him build a stronger line of defense against anxiety, anger, fear, and old patterns. Comedy, Ego, and the Pursuit of Success From leaving a career in insolvency accounting to becoming a touring stand-up comedian, Anthony reflects on how ego initially drove his ambition — and why external achievements did not bring the fulfillment he expected. Using Comedy to Give Back Anthony explores how comedy can become more than entertainment. He explains how laughter can disarm people, create connection, and become a way to share deeper ideas through humour. Redefining What Success Means In one of the most honest answers to the Owners Outlook signature question, Anthony challenges the word “success” itself and offers a grounded reminder that success is not always money, awards, or recognition — sometimes it is connection, presence, and walking away from a conversation feeling like something meaningful was shared. Tune in for a raw, thoughtful, and unexpectedly moving conversation about ego, healing, laughter, discipline, and what it really means to own your own success. Chapters: 0:00 Introduction 0:09 Anthony’s near-death experience in Canada 1:02 Discovering Vipassana meditation 3:34 The 10-day silent retreat experience 5:22 Building an emotional “secretary” through meditation 8:25 From insolvency accountant to stand-up comedian 12:20 Early ambition and building a comedy career 14:20 The emptiness behind external success 18:46 Ego, achievement, and personal collapse 21:02 Why Anthony almost quit comedy 22:02 Using comedy to give to others 25:41 Comedy as a Trojan horse for deeper ideas 34:18 Daily habits, meditation, writing, and discipline 41:31 Why laughter matters 46:09 The Owners Outlook signature question 46:50 Anthony’s definition of success 57:27 The Vipassana course and final reflections 59:20 Closing remarks
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