I asked ChatGPT to pitch 3 business ideas to serial entrepreneur Simon Squibb and his surprising feedback changed my mind about him

You might be familiar with Simon Squibb - he boasts over 17 million followers across social media platforms and has a No.1 Sunday Times best-selling book called What’s your dream?, which is about finding your passion, loving your work and building a richer life.

His Instagram account shows him stopping people in the street with a microphone and finding out what their dream is and then helping them take a step closer to making it real.

He has a lot of ideas, which often seem larger than life. For instance, he wants to “fix the education system,” wants to make society more giving, and he’s very open about his life experiences, such as being kicked out of home when he was younger, and how that gave him the impetus to turn his life around.

The reason I'm interviewing Simon, however, is that he's recently launched an AI version of himself, which he's offering for free on Android and iOS, so that he can reach more people with his help and advice at a time when jobs are under threat from AI.

AI pitches

In an age where we all present social media fronts of ourselves to the world, I wondered if Simon's relentlessly positive persona was a bit of a marketing gimmick, which is why I jumped at the chance to fire some pitches at him myself.

Not having any business ideas to pitch him myself, I hit upon the idea of getting AI (using ChatGPT) to come up with three pitches for the real Simon (not the AI version), and I’ve got to say I was surprised by his willingness to meet the challenge head-on and think on his feet.

I wanted to know what Simon was really like - he couldn’t really be as helpful as he appears on social media in real life, could he?

Pitch 1 - the hyper-local AI content creation studio

ChatGPT’s first pitch was a simple one - a hyper-local AI content creation studio offering AI-created content for a subscription fee to local businesses.

“I love that AI recommends AI!”, laughed Simon, before going on to give some good advice. “I think ideas are valueless - execution has value, not ideas. So, that’s a good idea, but execution is key.”

Pitch 2 - the subscription box

The next idea from ChatGPT was a niche subscription box for hobbyists targeting a specific underserved niche, e.g., calligraphy enthusiasts, retro gaming fans, or tabletop RPG newcomers. Each box would include curated supplies, printed zines, guides, or collectibles.

Again, Simon had some good advice to give: “Business 101 is that if you can own a niche, then you know exactly who you’re targeting and it makes it a lot easier. Every big business today started off in a niche - Facebook was in Universities, Instagram was for photographers. The downside is that there will always be a limit to how people will subscribe to that particular thing, so you need a way to scale up”.

Pitch 3 - micro Saas tool for freelancers or creatives

The last idea from ChatGPT was to develop a simple but targeted web app that solves a specific pain point for creatives or freelancers, e.g., time tracking with auto-invoicing.

“Actually, I’ve just invested in a business like this called Lovable, which is about to hit unicorn status - the fastest growing startup in Europe”, says Simon. “You speak what you want and it creates it, so these SaaS businesses are very easy to create. What I like about this idea is that it’s very easy to do, but the downside is that because more people will be doing it, it will be harder to generate subscription revenue. “

“The biggest challenge for any of these ideas in the future is going to be reach, which is why influencers are going to become more and more important because you can’t get noticed. I think reach, connection, community, and relationship is how you connect. If I share something with my community, I’m trusted and they will use it. That’s why I think the rise of influencers has only just begun.”

Creating agency

Well, he did it - I have to say I was impressed by Simon's ability to respond to my pitches, and the engaging way he communicates seems to be coming from a genuine place. I was starting to like him.

As I mentioned, faced with an increasingly large volume of people who want his advice, Simon has recently released an AI app version of himself, which is available completely for free. You can talk to AI Simon using your voice, and it’s like having a 1-1 chat with him.

So why did he make the app? “There are two main reasons. Firstly, I think people would like to know what the source of the knowledge is in AI - we don’t really know where the knowledge is coming from”. In the What’s your dream? app’s case, the knowledge comes directly from AI being trained on Simon’s material.

Secondly, it was simply about scale, “I have 1,000 people a day saying ‘Please Simon, can I have 5 minutes?’, I always try to help two people a day, but that’s the limit as a human, so I always felt like I left people behind, and that didn’t feel right.”

Thanks to Simon’s app, he has so far had 97,000 people use the platform, who have had 3.6 years’ worth of conversations, which are on average over 8 minutes.

“People are able to have a long conversation with AI me - and the feedback I’m getting is that it’s giving them the answers they need.”

So, I have to say talking to Simon has really changed my opinion of him. His positivity is infectious, and he seems really genuine in his desire to help people navigate the new world that AI is ushering in, and he’s using AI to do it.

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