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

➡️ Join 321,000 people who read my free weekly newsletter: https://newsletter.scottdclary.com

➡️ Like The Podcast? Leave A Rating: https://ratethispodcast.com/successstory

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.

➡️ Show Links

https://www.instagram.com/simonsquibb/ 

https://x.com/simonsquibb/ 

https://www.linkedin.com/in/simonsquibb/ 

➡️ Podcast Sponsors

Hubspot - https://hubspot.com/  

Vanta - https://www.vanta.com/scott 

Federated Computer - https://www.federated.computer 

Lingoda - https://try.lingoda.com/success_sprint

Cornbread Hemp - https://cornbreadhemp.com/success (Code: Success)

FreshBooks - https://www.freshbooks.com/pricing-offer/ 

Quince - https://quince.com/success 

Northwest Registered Agent - https://www.northwestregisteredagent.com/success 

Prolon - https://prolonlife.com/clary 

Stash - https://get.stash.com/successstory 

NetSuite — https://netsuite.com/scottclary/ 

Indeed - https://indeed.com/clary

➡️ 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

25:18 – Sponsor Break

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

1:00:12 – Sponsor Break

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

Welcome to the Success Story Podcast, hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary (@scottdclary). On this podcast, you'll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship. Scott will discuss some of the lessons he's learned over his own career, as well as have candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights. He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between. To get more of the Success Story podcast, go to www.successstorypodcast.com.