Why Side Hustles Might Be the Smartest Move! | Simon Squibb

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Simon Squibb: Why Working for Yourself Isn’t Risky Anymore

In this episode of Jimmy’s Jobs of the Future, Simon Squibb – millionaire entrepreneur and education reformer – explains why the school system is outdated and failing future founders.

He shares how being kicked out of school at 15 shaped his mission to fix it. From homeschooling his son to building a global audience, Simon reveals the highs and lows of content creation, how to build personal brand influence, and why entrepreneurship isn’t as risky as you think.

You’ll also hear his thoughts on AI, politics, and the radical shift we need in how we teach young people about money, work, and life.

Timestamps:
00:00 Intro
01:45 Everything Wrong With School
04:01 The Truth About Entrepreneurship
12:36 Why Every Founder Needs a Personal Brand
14:00 AI Is Coming – Are You Ready?
15:00 Simon’s Wild Journey to Success
21:52 The Hidden Cost of Fame
26:22 Losing a Parent and Gaining Perspective
27:32 How to Actually Fix Education
29:15 Social Media Changed Everything
33:58 Content Is a Full-Time Job
35:08 Street Interviews & Real Reactions
44:35 Homeschooling Done Right
49:33 Final Thoughts on Risk, Dreams & Purpose

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Credits:
Host / Exec Producer: Jimmy McLoughlin OBE
Producer: Sunny Winter   / sunnywinter  
Junior Producer: Thuy Dong