#551 - VO - Simon Squibb - Content creator - The Dreams Maker episode artwork

EPISODE · Jun 28, 2026 · 2H

#551 - VO - Simon Squibb - Content creator - The Dreams Maker

from Génération Do It Yourself · host Matthieu Stefani | Orso Media

Retrouvez l'épisode en version française ici : https://www.gdiy.fr/podcast/simon-squibb-vf/"What's your dream?"Four words that Simon Squibb has asked over 10,000 strangers on street corners, outside food banks, in airports all around the world.Most people freeze.That moment of blankness is exactly the problem he has spent the last decade trying to fix.Simon dropped out of school at 15 when his father died and his mother kicked him out.Then came eight weeks sleeping in stairwells and on the streets, which lit in him a relentless drive to build and create.So he knocked on a stranger's door, announced he was starting a gardening company, and charged £200 a month for a garden he didn't know how to tend.That business lasted eight months before the English winter killed it.After that, Simon builds, shuts down and resells several businesses, leading up to Fluid, a creative agency he grows for twenty years out of Hong Kong before handing it over to PwC.Then he retires, and despite having everything, he nearly loses himself.In 2019, he starts approaching strangers in the street to ask them about their dream.Today Simon has 15 million followers across platforms and he is the number one result on TikTok when you search "angel investor."He has given away over £426,000 to help people start businesses.His two-hour YouTube video on building a brand has been watched 17 million times.For Simon, the education system became obsolete the day Google was born, so he isn't trying to change it, he's building an alternative.In this conversation, Simon shares:Why TikTok made marketing degrees worthlessHow to wake up your entrepreneur's brainWhy he gave up on politics to try to change the education systemHow to find your dream when you're too busy surviving to think about itWhy your purpose in life comes from your painAn episode for anyone who's ever frozen when someone asked what they really wanted.You can follow Simon on Instagram and TikTok.TIMELINE:00:00:00 : They Were Promised Jobs That Don't Exist00:13:21 : TikTok Made Marketing Degrees Worthless00:19:28 : School Trains You to Fail in the Real World00:26:30 : The Muscle School Spends 10 Years Killing00:36:46 : The Salary Addiction Builds Nothing You Own00:48:45 : Giving Away a £10 Million Course for Free01:00:52 : You Can't Dream While Running From the Lion01:10:07 : The Million-Dollar Failure He's Grateful For01:16:44 : Money Won't Fix What You Already Feel01:23:06 : No One Is Self-Made01:30:17 : Brexit Was a Lie01:38:53 : Most People Don't Need Money01:45:49 : Only Dreams Can Buy Loyalty01:54:22 : Building a Hotel Booking Business Before the InternetWe referred to previous GDIY episodes : #527 - Céline Chung - Bao Family - La reine de la street food asiatique#525 - Joseph Lasserre - Groupe Doumer - Racheter des entreprises dont personne ne veut#507 - Laurent Alexandre - Vers la fin des études supérieures ?#487 - VO - Anton Osika - Lovable - Internet, Business, and AI: Nothing Will Ever Be the Same Again#487 - VF - Anton Osika - Lovable - Internet, Business et IA : rien ne sera jamais plus comme avant#327 - Laurent Alexandre - Auteur - ChatGPT & IA : "Dans 6 mois, il sera trop tard pour s'y intéresser"#165 - Laurent Alexandre - Doctissimo - La nécessité d'affirmer ses idéesA few recent episodes in English : #542 - VO - Yoni Assia - eToro - “AI Will Replace Most Traders in 18 Months”#513 - VO - Jesper Brodin - IKEA - 40 billion in revenue empire with no bank loan#500 - VO - Reid Hoffman - LinkedIn, Paypal - How to master humanity’s most powerful invention#487 - VO - Anton Osika - Lovable - Internet, Business, and AI: Nothing Will Ever Be the Same Again#475 - VO - Shane Parrish - Farnam Street - Clear Thinking: The Decision-Making Expert#473 - VO - Brian Chesky - Airbnb - « We're just getting started »#452 - VO - Reid Hoffman - LinkedIn, Paypal - L’humanité 2.0 : Homo technicus plus qu’Homo sapiens#437 - James Dyson - Dyson - “Failure is more exciting than success”#431 - Sean Rad - Tinder - How the swipe fever took over the worldWe spoke about :Harvard UniversityYC turns builders into formidable foundersAnthropic AcademyThe Survivorship bias30 Years of Business Knowledge in 2hrs 26minsThe Maka TwinsReading Recommendations :What's Your Dream?, by Simon Squibb 🇬🇧Pour Your Heart Into It, by Howard Schultz 🇬🇧Losing My Virginity, by Richard Branson 🇬🇧A huge THANK YOU to our sponsors : Squarespace : https://squarespace.com/doitQonto: https://qonto.com/r/2i7tk9 Brevo: brevo.com/doit eToro: https://bit.ly/3GTSh0k Payfit: payfit.com Club Med : clubmed.frCuure : https://cuure.com/product-onely You'll find the full list of gear we use to record our episodes on this page.Interested in sponsoring Generation Do It Yourself or proposing a partnership ? Contact my label Orso Media through this form.Hébergé par Audiomeans. Visitez audiomeans.fr/politique-de-confidentialite pour plus d'informations.

Retrouvez l'épisode en version française ici : https://www.gdiy.fr/podcast/simon-squibb-vf/ "What's your dream?" Four words that Simon Squibb has asked over 10,000 strangers on street corners, outside food banks, in airports all around the world. Most people freeze. That moment of blankness is exactly the problem he has spent the last decade trying to fix. Simon dropped out of school at 15 when his father died and his mother kicked him out. Then came eight weeks sleeping in stairwells and on the streets, which lit in him a relentless drive to build and create. So he knocked on a stranger's door, announced he was starting a gardening company, and charged £200 a month for a garden he didn't know how to tend. That business lasted eight months before the English winter killed it. After that, Simon builds, shuts down and resells several businesses, leading up to Fluid, a creative agency he grows for twenty years out of Hong Kong before handing it over to PwC. Then he retires, and despite having everything, he nearly loses himself. In 2019, he starts approaching strangers in the street to ask them about their dream. Today Simon has 15 million followers across platforms and he is the number one result on TikTok when you search "angel investor." He has given away over £426,000 to help people start businesses. His two-hour YouTube video on building a brand has been watched 17 million times. For Simon, the education system became obsolete the day Google was born, so he isn't trying to change it, he's building an alternative. In this conversation, Simon shares: - Why TikTok made marketing degrees worthless- How to wake up your entrepreneur's brain- Why he gave up on politics to try to change the education system- How to find your dream when you're too busy surviving to think about it- Why your purpose in life comes from your painAn episode for anyone who's ever frozen when someone asked what they really wanted. You can follow Simon on Instagram and TikTok. TIMELINE: - 00:00:00 : They Were Promised Jobs That Don't Exist- 00:13:21 : TikTok Made Marketing Degrees Worthless- 00:19:28 : School Trains You to Fail in the Real World- 00:26:30 : The Muscle School Spends 10 Years Killing- 00:36:46 : The Salary Addiction Builds Nothing You Own- 00:48:45 : Giving Away a £10 Million Course for Free- 01:00:52 : You Can't Dream While Running From the Lion- 01:10:07 : The Million-Dollar Failure He's Grateful For- 01:16:44 : Money Won't Fix What You Already Feel- 01:23:06 : No One Is Self-Made- 01:30:17 : Brexit Was a Lie- 01:38:53 : Most People Don't Need Money- 01:45:49 : Only Dreams Can Buy Loyalty- 01:54:22 : Building a Hotel Booking Business Before the Internet We referred to previous GDIY episodes : - #527 - Céline Chung - Bao Family - La reine de la street food asiatique- #525 - Joseph Lasserre - Groupe Doumer - Racheter des entreprises dont personne ne veut- #507 - Laurent Alexandre - Vers la fin des études supérieures ?- #487 - VO - Anton Osika - Lovable - Internet, Business, and AI: Nothing Will Ever Be the Same Again- #487 - VF - Anton Osika - Lovable - Internet, Business et IA : rien ne sera jamais plus comme avant- #327 - Laurent Alexandre - Auteur - ChatGPT & IA : "Dans 6 mois, il sera trop tard pour s'y intéresser"- #165 - Laurent Alexandre - Doctissimo - La nécessité d'affirmer ses idées A few recent episodes in English : - #542 - VO - Yoni Assia - eToro - “AI Will Replace Most Traders in 18 Months”- #513 - VO - Jesper Brodin - IKEA - 40 billion in revenue empire with no bank loan- #500 - VO - Reid Hoffman - LinkedIn, Paypal - How to master humanity’s most powerful invention- #487 - VO - Anton Osika - Lovable - Internet, Business, and AI: Nothing Will Ever Be the Same Again- #475 - VO - Shane Parrish - Farnam Street - Clear Thinking: The Decision-Making Expert- #473 - VO - Brian Chesky - Airbnb - « We're just getting started »- #452 - VO - Reid Hoffman - LinkedIn, Paypal - L’humanité 2.0 : Homo technicus plus qu’Homo sapiens- #437 - James Dyson - Dyson - “Failure is more exciting than success”- #431 - Sean Rad - Tinder - How the swipe fever took over the worldWe spoke about : - Harvard University- YC turns builders into formidable founders- Anthropic Academy- The Survivorship bias- 30 Years of Business Knowledge in 2hrs 26mins- The Maka Twins Reading Recommendations : - What's Your Dream?, by Simon Squibb 🇬🇧- Pour Your Heart Into It, by Howard Schultz 🇬🇧- Losing My Virginity, by Richard Branson 🇬🇧 A huge THANK YOU to our sponsors : Squarespace : https://squarespace.com/doit Qonto: https://qonto.com/r/2i7tk9 Brevo: brevo.com/doit eToro: https://bit.ly/3GTSh0k Payfit: payfit.com Club Med : clubmed.fr Cuure : https://cuure.com/product-onely You'll find the full list of gear we use to record our episodes on this page. Interested in sponsoring Generation Do It Yourself or proposing a partnership ? Contact my label Orso Media through this form. Hébergé par Audiomeans. Visitez audiomeans.fr/politique-de-confidentialite pour plus d'informations.

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#551 - VO - Simon Squibb - Content creator - The Dreams Maker

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This episode was published on June 28, 2026.

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Retrouvez l'épisode en version française ici : https://www.gdiy.fr/podcast/simon-squibb-vf/"What's your dream?"Four words that Simon Squibb has asked over 10,000 strangers on street corners, outside food banks, in airports all around the world.Most...

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