Simon Squibb - Founder & Investor | From Homeless Teen to Serial Entrepreneur

Simon Squibb is a Sunday Times bestselling author whose book What’s Your Dream? distills over 30 years of business experience into a concise 2 hour 26 minute guide for aspiring entrepreneurs. As founder of HelpBnk.com, he launched his first venture at age 15 while homeless and later sold his digital agency, Fluid, to PwC in a multimillion-pound transaction. Renowned for his viral London “staircase doorbell” stunt, he’s on a mission to empower 10 million people to kickstart their own businesses through his #GiveWithoutTake street interviews. His message reaches over 14 million followers across social platforms—including 6.8 million TikTok fans with 179 million total likes—making him one of the most influential voices in modern entrepreneurship.

➡️ Talking Points

00:00 — Intro

01:37 — Simon’s Ultimate Dream

02:56 — Life-Changing Turning Point

08:24 — Give Without Expecting

16:44 — Can Education Cure Selfishness?

20:38 — Work Hard Without Losing Yourself

29:10 — Ready to Quit? Start Here

32:57 — Don’t Know Your Dream? Start Here

36:13 — Is It the Right Dream?

45:03 — Watch Who You Listen To

47:20 — Traits of Dream Achievers

50:38 — How to Feel the Struggle (Without Struggling)

52:48 — Purpose Over People Management

55:23 — Get People to Believe in You

1:04:17 — Is Property Still Worth It?

1:20:44 — Investing 101: Where to Start

1:26:48 — Simon’s Final Advice

1:27:47 — Risk That Paid Off Big

1:30:13 — Hard Lesson You Don’t Want

1:31:01 — Hack Your Luck

1:35:05 — One Lesson for His Kids