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SIMON SQUIBB'S CONTENT PLAYBOOK: THE HOOK THAT BUILT A MOVEMENT
The step-by-step framework behind Simon Squibb’s viral content and how to apply it to your brand
Niall Ratcliffe
March 16, 2025
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BREAKING DOWN THE STRATEGY
In 2001, Simon Squibb was just another entrepreneur hustling to grow his agency, Fluid, out in Hong Kong.
No viral videos
No social media fame
No millions of followers
Just a guy trying to make his business work.
16 years later, his life changed forever when he sold Fluid to PwC in a multi-million pound deal. From that day on, Simon would never have to work another day in his life.
And at that point, most people would have:
Gone and bought a nice watch.
Then a car or a Spanish villa.
Then played golf and drank cocktails.
But Simon did the exact opposite.
Instead of retiring, he threw himself into helping people start businesses - for free. He started investing in startups, mentoring founders, and (more importantly) telling his story online.
At first, it was classic business content.
Talking head videos.
Lessons from his journey.
Random thoughts on business.
Today, it’s safe to say he has come a long way since then. He has:
11 million followers across platforms.
A Sunday Times best-selling book.
And he’s known around the world.
He’s one of the most famous businessmen on social media.
But this wasn’t luck. Simon engineered his virality.
And today, I’m going to reverse engineer the exact playbook he used to do it.
Let’s get into it!
Step 1: Take Stabs In The Dark
When Simon Squibb first got started on social media, he followed the classic business guru playbook.
He shared talking-head videos.
Threw on some captions.
And gave business lessons.
And honestly… it was kinda working.
He was slowly gaining followers, averaging 8,000 views per video with very little effort.
But everything changed one day when he did a TikTok Live.
During one of Simon’s TikTok Lives, viewers started donating money (you can do this on TikTok), and by the end of the session, he’d received £150 in donations.
But for Simon, his mission was simple - he wanted to help people start businesses for free. So, instead of keeping the money, he withdrew the cash, walked into Tesco, and asked the first woman he saw:
“Would you ever want to start a business of your own?”
Her eyes lit up. She shared her business idea, and right then, Simon handed her the money and told her to go and start the business.
Simon said, “It was a magical moment.” But there was just one problem: he didn’t film it.
Realising the missed opportunity, he withdrew more cash, went to Pizza Express, and did it again. This time, with a camera.
Same question.
Same concept.
But on video.
His team rushed home, edited the video and got it live on TikTok.
Boom! 60,000 views. They were onto something.
They were throwing mud at the wall and finally something had stuck. From there, it was all about testing (AKA taking more stabs in the dark):
So they tweaked the question slightly.
Then they tried different settings.
Then camera angles.
The next minute, they stumbled on the golden question:
“What’s your dream?”
They used it in a video and the video went viral. It was that hook that changed everything. The content took off, his brand exploded, all from that one question he started asking people.
Today, Simon’s entire personal brand revolves around this simple question - even his bestselling book is named, ‘What’s your dream?’
And it all started with throwing mud at the wall and seeing what sticks.
That’s what makes the on-the-street interview format so powerful. It’s an A/B test every single time. Ask different questions, see what grabs attention, and refine until you find the viral spark.
Simon’s content strategy was nothing special in the beginning. But by taking stabs in the dark, he uncovered a format that worked - and then built an entire movement around it.
Step 2: Iterate & Build Upon It
Once Simon Squibb’s team found their viral format - the initial "Would you ever start a business of your own?" - their videos began to take off.
But one of the biggest mistakes most people make when they find their golden format is they do 1 of 2 things:
Sit on their hands: repeating the same thing without evolving it.
Over-iterate: They iterate away from what worked in the first place.
But Simon’s success came from constantly iterating and refining the exact same format without losing what made it work.
His marketing team explained on a podcast that within months of hitting that golden format, they tested:
Tweaking the music - to test whether certain soundtracks increased engagement.
Different camera angles - to see what viewers would prefer.
Hook variations - small wording changes to test the impact.
Changing locations - moving from the street to restaurants, cafés, and other settings.
Introducing new twists - like asking a waiter: “Would you rather have a £1,000 tip or my book?”
Upgrading production quality - moving from simple phone recordings to using a full camera crew.
The key takeaway I took from this?
→ A viral format isn’t the endpoint - it’s the starting point.
Simon Squibb’s team has spent years optimising the same simple format - and that’s why he continues to go viral and gain millions of followers.
Step 3: Expand Out For More Reach
Simon’s first successful hook - "Would you ever start a business of your own?" -had a major limitation.
Not everyone is interested in starting a business.
For a long time, his content only resonated with a specific type of viewer - people who were already business-minded. But if they wanted to scale and reach millions, they knew they had to find a way to engage the “Typical TikTok viewer” (as they called it).
That’s when they started to think about Edutainment.
Simon’s goal was always to educate people about business, but his team realised that they essentially needed to trick people into being educated - by entertaining them first.
So, they broadened the hook from business-specific to something that anyone could relate to:
"What’s your dream?"
And it was that switch that took them from niche success to mass virality.
Step 4: Communicate The Mission
In one of his recent videos Squibb said, “The best companies don’t necessarily have the best service, but they are the best at communicating their mission.”
And this was a theme his marketing team were hammering home on that recent podcast.
They said:
“Who is the most famous entrepreneur on the planet right now? Most people would say Elon Musk. And why?
Because he has a massive mission: To take humans to Mars.”
They then explained that mission does 3 things for him:
It makes him interesting.
It gets people talking about him.
It gives people something to rally behind.
Now, apply this to Simon Squibb.
His mission: Change the education system.
And it’s that mission that allows people to get behind what he stands for, rather than just him as a person.
Not everyone likes Elon Musk. But even if you don’t like him, the idea of humans colonising Mars is fascinating. The mission itself is compelling.
The same principle applies to Simon Squibb. People might not connect with him personally, but they do connect with the idea of fixing a broken education system.
Step 5: Push More Buttons & Don’t Miss A Trick
Simon’s marketing team said that the most common thing Simon says to them is “Don’t miss a trick.”
Because if there’s an easy way to get more engagement, more reach, or more followers - he wants them to take it.
One of the best examples of this was their expansion to new platforms.
At first, Simon was only posting on TikTok. But once they saw success, they asked a simple question: where else could this work?
They started posting the same content on Instagram.
Then they repurposed it for YouTube Shorts.
Then they realised they weren’t on Snapchat.
Snapchat wasn’t a platform many business creators were focusing on. But they tested it anyway - and it took off. They gained millions of followers just by posting the same style of content on a new platform.
From there, they refined the process further. Instead of just reposting the same videos everywhere, they started adding native captions for each platform, making the content feel tailored rather than repurposed.
They hit more buttons and have never missed a trick since.
🌱 THE GREENHOUSE
Things I’ve saved this week that are worth seeing:
TL;DR
Step 1: Take Stabs in the Dark
Step 2: Iterate and Build Upon It
Step 3: Expand Out for More Reach
Step 4: Have a Mission
Step 5: Push More Buttons and Don’t Miss a Trick
If you want to be the next Simon Squibb, this playbook is exactly how you make that happen. He seems like a very nice guy, but he’s also an incredible content creator. I have a feeling we’re only seeing the start of his journey.
Hopefully you found this playbook useful. If you did, share it with a friend.
Until next Sunday.
— Niall
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