Simon Squibb
Entrepreneur
19
APPEARANCES
17
PODCASTS
012
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Nov 6, 2026
Simon Squibb: Homeless at 15, Multimillionaire by 40 | The Truth About Money, Success & Chasing Your Dreams
25:19
31:13

Ellie McKayHOST
You're really looking at the social mobility aspect and making this information, knowledge, wisdom accessible to absolutely everyone because people are getting left behind.
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25:30Simon SquibbGUEST
not against that at all just to say you know like i think if people can sell a course and bring value then then great what i'm saying is that if everything is priced up in a way that it means a lot of people cannot get access to that knowledge that doesn't feel right to me and then the argument against this philosophy which is where i start to get annoyed is people say if you don't pay you don't pay attention right that is not true What I have discovered is if you bring true value to people, they will pay attention.

Ellie McKayHOST
And when the potential customer was ringing up and the hotel was doing the old-school phone, like, who actually has a phone like this now um they'd ring up and it was full that would be it just all that marketing has gone to waste so you spotted an opportunity and got them to to basically divert them to you and you then sought them alternative accommodation i think do you sometimes dumb down your own achievements a little bit because that that is a bit unusual
Simon Squibb: Why Money Won't Make You Happy, Finding Your Purpose and Building a Life You Love
27:37
Simon SquibbGUEST
I've helped myself, first of all, because I've gone through stages in life, you know, the 15-year-old me.
That Time We Had Simon Squibb Fund People's Dreams Live - 16 Oct 26
86:56
87:02
Simon SquibbGUEST
Because, because, you know, there's all sorts of different types of doctors, there's all sorts of different types of lawyers, there's all sorts of different types of entrepreneurs.
Simon SquibbGUEST
So I think sometimes it's just giving you the knowledge to- Mm-hmm ... to have, uh, the ability to start a business.
Simon Squibb Speaks to Pulse95 at Sharjah Investment Forum 2026 (15.10.2026)
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1:57Rania SaadiHOST
Um, do you have a dream? How did you come about this idea? What went through your head before you actually started this revolution? And did Help Bank, um, help you achieve what you were trying to achieve with that?
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2:11Simon SquibbGUEST
Well, I, I realized that a lot of people have a dream, but they've never been asked.
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2:16Simon SquibbGUEST
A lot of people have been asked, "What will you do when you grow up?" But no one's really been asked, "What problem would you like to solve?" And if you ask someone, young people in particular, "What will you do when you grow up?" They try to find an answer to make the adults happy.
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2:31Simon SquibbGUEST
A lot of young people, "Oh, I'm gonna be a doctor," "I'm gonna be a lawyer," which is fine.
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2:35Simon SquibbGUEST
But is it really their dream, or is it a dream embedded in them at eight years old when someone asked them, "What will you do when you grow up?" And in reality, the world is changing, and I think it's quite exciting.
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4:40Rania SaadiHOST
You going around asking someone, "Do you have a dream?" Was there a particular dream that kind of stuck with you? You were like, "This is something that I, as Simon, changed me after I chose it and invested in it." And why did you choose that? If you can give me just an example.
EP1 - Are Careers Dead? (with Simon Squibb)
1:25
Simon SquibbGUEST
And they do have a pressure from the education system to perform for the education system that is broken.
Begin Again Moments: Growing Up With A Narcissistic Parent
0:56
1:06
1:11
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0:46speaker_1ADVERTISER
Football's on all season long on ESPN and streaming on the ESPN app.
Simon SquibbGUEST
I lived in a small town called St Neots, and we went shopping one day in Bedford, which is nearby, maybe, you know, a 30-minute or so bus ride away.
Simon SquibbGUEST
And so we went there, and, um, and I remember, it's probably one of my earliest memories as, as a child.
Simon SquibbGUEST
I can remember it so clearly 'cause we were having a nice day, and we were shopping.
6 MINS LATER
Simon Squibb: From Homeless at 15 to Finding His Purpose- What's Your Dream?
24:24
24:29
24:43
24:48

Charlie MooseHOST
When I no longer had something to do every day, it was great for six months, and then I lost my mind.
Simon SquibbGUEST
mind.I was like, "Who am I? Why am I here? What is the point?" I, I was so inward-looking that I, I literally kind of went a bit crazy, and I got digestive issues.
Simon SquibbGUEST
You know, all these things of having no stress, it's not natural for humans to have no stress.
Simon SquibbGUEST
And so I didn't have a reason to get up in the morning and go out and do stuff, right? And so I lost my way, and it was, it was actually one day my wife saying to me...
6 MINS LATER
Simon Squibb: Turn Your WANT Into a NEED | Founder Classics
1:01
1:14

Alex ChisnallHOST
What was the eureka moment, the aha moment, the screw it, just do it moment that you decided to take this idea that you had and actually do something about it, rather than talk about it, which 99% of people do?
Simon SquibbGUEST
You know, I think a lot of the time people think that ideas like the Purposeful Project start as this massive idea that you just start doing.
A step-by-step guide to finding your dream life and actually making it happen with Simon Squibb
9:04
9:20
9:29

Grace BeverleyHOST
So I'd love to hear kind of from that point, how did that turn into your entrepreneurial journey? Because I can imagine at the same time that turning into anything else would've still been a leap.
Simon SquibbGUEST
Need all your listeners by asking to put up their hands and say, "Who wants to be successful?" Everyone's listening right now because they do.
Simon SquibbGUEST
The truth is, the only way you make your life better is needing it, but you can fabricate it.
37 MINS LATER
658 - SIMON SQUIBB - The Internet’s Most Controversial Dream Seller - From Homeless School Dropout, To Multi-Millionaire Giving Away His Fortune
54:23
54:33
Simon SquibbGUEST
CNN wanted to go into Asia, so they would ask us, "How would you do it?" We give them ideas, and then they pay us to do the execution of that idea.
Simon SquibbGUEST
Um, but Helen was the talent, and I was, again, the guy who just knocked on doors.
22 MINS LATER
J
76:24JaackMaateHOST
But say someone that Jack said, like, someone's broke, they wanna try and earn money quickly, how, how can you then affect anything if you've not got anywhere to cause that effect?
Simon Squibb: Dream vs. Goal
11:31
Simon SquibbGUEST
I actually see my role is to give people all the things they say they need, and now what? And I've done it many times.
26 MINS LATER
Begin Again Moments: The Reality of Homelessness
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Simon SquibbGUEST
Yeah, and I, and I, even now, when I think about it now, I feel a bit sad about it because it's, it's, um...
Simon SquibbGUEST
We're all together in a house, and then suddenly I'm on my own out in the real world.
Simon SquibbGUEST
And I think the thing that really hit me was just how unprepared I was for the real world, even though that eight-year-old experience, that wasn't my daily experience.
Full Show Podcast: 29 January 2026
70:23
Simon SquibbGUEST
And then because, you know, in the clips, we can't show every detail because it's too much.
71:49
Okay, so what do you do? What's in it for you? Do you take a stake in
Simon Squibb: entrepreneur and influencer reveals why he's committed to helping Kiwis fund their dreams
2:49
2:55
Simon SquibbGUEST
I'm staying nearby an Airbnb and I just went there for breakfast, totally random.
Simon SquibbGUEST
And then because, you know, in the clips, we can't show every detail because it's too much.
4:21
Okay, so what do you do? What's in it for you? Do you take a stake in
20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
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Simon SquibbGUEST
When I first started doing the content, I was doing, like, how to raise money, and I was talking about how to find a co-founder, and the videos were doing okay on the views.
Simon SquibbGUEST
It was doing average, and then I thought, "All right, go into the street and ask people, 'But why are they not actually doing it?'" And most of the time, they're not even giving themselves the time to think of something, you know? So that, that's why, "What's your dream now?" by the way, is pretty much like a standard saying.
Simon SquibbGUEST
People, when they meet each other, ask each other now, though, what's their dream.
14 MINS LATER
How to Build a Business That Doesn't Need You With Simon Squib
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44:08Brad SugarsHOST
Best advice you ever got on success and who gave it to you and why is it important to you?
Is the UK-US trade deal a Brexit win?
22 MINS LATER
Simon Squibb: Investing in Strangers, Building Businesses and Our Education Problem (E322)
22:29

Damian HughesHOST
Can we go through each of those seven reasons that people often put in their own way that stop them seeing work as something to enjoy? You're
13 MINS LATER






