You may already know Simon Squibb — he’s amassed over 17 million followers across social platforms and authored What’s your dream?, a Sunday Times No.1 bestseller focused on discovering passion, enjoying your career, and creating a more meaningful life.

On Instagram, he’s known for approaching strangers with a microphone, asking them about their dreams, and then helping them take real steps toward achieving them.

He’s full of bold, ambitious ideas — from overhauling the education system to fostering a more generous society. He’s also open about his past, like being forced to leave home at a young age, an experience that became a catalyst for transforming his life.

But the reason I sat down with Simon is his latest move: launching a free AI version of himself, available on both Android and iOS, designed to extend his guidance to more people during a time when AI is disrupting jobs and livelihoods.

AI pitches

In an era where everyone curates a polished online persona, I wondered if Simon’s constant optimism was just a clever brand strategy. That’s why I jumped at the chance to test him — not with my own ideas, but with AI-generated ones.

Since I didn’t have any business concepts ready, I turned to ChatGPT to create three pitches for the real Simon (not the digital clone). I was genuinely surprised by how eager he was to engage, think on the spot, and offer thoughtful feedback.

I wanted to see the real Simon — could someone truly be this supportive and enthusiastic in person?

Pitch 1 – A hyper-local AI content studio

ChatGPT’s first idea? A hyper-local AI-powered content studio that creates tailored content for small businesses on a subscription basis.

Simon chuckled. “I love that AI is pitching AI!” Then he got serious. “Ideas themselves are worthless — it’s execution that matters. This is a solid concept, but success will depend entirely on how well it’s carried out.”

Pitch 2 – A niche subscription box

Next up: a subscription box tailored to underserved hobbyist communities — think calligraphy lovers, retro gaming fans, or new tabletop RPG players. Each box would feature handpicked tools, printed zines, guides, or collectible items.

Simon nodded in agreement. “Niche markets are powerful. If you own a niche, you know exactly who you’re speaking to. Look at Facebook — started in colleges. Instagram — built for photographers. The challenge? Growth ceilings. You’ve got to plan how to scale beyond the core audience.”

Pitch 3 – A micro SaaS tool for creatives

Final pitch: a lightweight web app solving a specific problem for freelancers or creatives — say, time tracking with automatic invoicing.

“Funny you mention that,” Simon said. “I just invested in a company called Lovable — it’s on track to become a unicorn, fastest-growing startup in Europe right now. You speak your idea, and it builds it. Tools like this are easy to develop. The issue? Market saturation. As more people build similar tools, monetizing through subscriptions gets tougher.”

He added, “The real bottleneck moving forward will be visibility. That’s where influencers come in. Trust and reach are everything. When I recommend something to my audience, they listen — because there’s a relationship. That’s why influencer impact is only beginning to take off.”

Building real impact

Honestly, I’m impressed. Simon handled the AI pitches with insight and authenticity. His energetic, people-first style doesn’t feel staged — it seems to come from a real place. I’m starting to believe in him.

As mentioned, with thousands seeking his advice daily, Simon created a free AI-powered app — a digital version of himself. You can speak to it naturally, like having a personal conversation.

So why build it? Two reasons, he says. “First, transparency. Most AI doesn’t tell you where its knowledge comes from. In this app, every response is trained directly on my content — books, talks, interviews. You know the source.”

“Second, scale. Every day, 1,000 people ask me for five minutes. I try to help two a day, but as a human, that’s my limit. It felt wrong to leave so many behind.”

To date, 97,000 people have used the app, accumulating the equivalent of 3.6 years of conversation time — with average chats lasting over 8 minutes.

“People are having deep, meaningful exchanges with AI Simon. And they’re walking away with answers they actually needed.”

After speaking with him, my view has shifted. His optimism is contagious, and his mission — using AI to help people thrive in an AI-driven world — feels both sincere and forward-thinking.

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