Simon Squibb: The Education System is Failing us! This is Why We Need to Rethink School

2025-08-14

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In this episode of Begin Again, Simon Squibb shares his extraordinary story of overcoming adversity, personal transformation, and resilience. From being kicked out of his home at 15 to navigating the harsh realities of homelessness, Simon reveals how these challenges shaped his path to success. Simon, best known for his social series What's Your Dream, opens up about the pivotal moments in his life, his struggles with loss, survival, and finding purpose, and how these experiences fueled his entrepreneurial...

In this episode of Begin Again, Simon Squibb shares his extraordinary story of overcoming adversity, personal transformation, and resilience. From being kicked out of his home at 15 to navigating the harsh realities of homelessness, Simon reveals how these challenges shaped his path to success.

Simon, best known for his social series What's Your Dream, opens up about the pivotal moments in his life, his struggles with loss, survival, and finding purpose, and how these experiences fueled his entrepreneurial journey. With a mission to help others and empower them to pursue their dreams, Simon talks about the power of pain in driving passion, the importance of supporting others, and how his desire to uplift those who are struggling keeps him going.

In this candid conversation, Simon reflects on his unconventional path, the lessons he’s learned about empathy, failure, and rebuilding, and how helping others is the key to finding true happiness.

This episode is a powerful reminder that no matter where you start, it’s never too late to begin again and build a life driven by purpose, resilience, and a commitment to making a difference in the lives of others.

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(00:00) Intro
(01:17) The Power of Helping Others
(03:48) Simon’s Difficult Childhood Story
(06:31) Caring for Himself at Just 8 Years Old
(09:18) Homeless at 15 After Being Kicked Out by His Mother
(11:04) Reflections on Motherhood and Narcissistic Traits
(14:44) Losing His Father at 15 and Lessons Learned
(17:22) Turning Pain Into Motivation to Help Others
(18:37) How Lack of Parental Support Impacts Dreams
(19:30) Life Lessons From Experiencing Homelessness
(23:39) Choosing Money vs. Happiness
(24:26) How to Find Your True Purpose in Life
(25:48) Starting His First Business ‘Fluid’ at Age 24
(26:56) The Life-Changing Gift of Giving
(28:00) Supporting and Encouraging Your Partner’s Dreams
(36:17) How Pain Can Drive Your Purpose
(38:02) Why the Education System Fails and How to Successfully Home-School Your Kids
(44:46) Why Failure Is the Key to Success
(48:29) Why You Only Need Your First Customer to Start
(52:48) Practicing Gratitude and Turning Pain Into Strength
(58:14) How to Manage People Who Dislike You
(1:01:53) Simon’s Biggest Dream for the Future