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Jobs of the Future, Simon Squibb – millionaire entrepreneur and education reformer – explains why the school system is outdated and failing future founders.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 https://www.linkedin.com/in/sunnywinter/

Junior Producer: Thuy Dong

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