From Lockdown to Liftoff The entrepreneur fueling a new wave of founders

Jack Whettingsteel's journey from supermarket night shifts to co-founding HelpBnk, a community-powered platform that's redefining how entrepreneurs access mentorship, with Simon Squibb, is a striking reminder that the path to entrepreneurship doesn't have to be conventional. Whettingsteel's entrepreneurial journey didn't begin in a boardroom or business school - it started in a Sainsbury's during lockdown, with nothing but curiosity, TikTok, and a desire to break free from the system. In this exclusive Entrepreneur UK interview, Whettingsteel reflects on investing his mum's £3,000 life savings in a marketing course, pitching Richard Branson on a flight to New York, and launching the Doorbell of Dreams to bring bold ideas to life.

You've had an unconventional entrepreneurial journey. Can you take us back to the beginning and share what first sparked your passion for helping entrepreneurs?
I've always had an intense drive to do something meaningful, but growing up, I wasn't sure what that meant. As a kid, I said I wanted to be an inventor because it seemed cool, but the education system didn't see that as a 'real job', so I quickly abandoned that dream. Throughout school, I had a real anger at the path it seemed to be pushing me down and the things it was making me do. The system felt limiting - it pushed me down a predetermined route that didn't align with who I was or what I felt capable of achieving. It wasn't until I was 19, during lockdown, whilst working at Sainsbury's as an assistant manager, that everything changed. I had more time, like everyone did, and suddenly TikTok's algorithm started showing me content around self-development. I began learning things school never taught me - how finances actually worked, what mortgages were, basic life skills that should have been fundamental education. The algorithm, which seemed to know me better than I knew myself, started serving up entrepreneurship content. I started seeing people making an entire yearly salary in a single month online, and I was absolutely hooked. For the first time in my life, after feeling somewhat confused about what the right path was for me, everything suddenly made sense. I became obsessed with the idea of entrepreneurship - not just for the money, but for the freedom and possibility it represented. That wake-up moment changed everything. Ever since, I've been motivated to help others have that same realisation - that life can be so much more than what the system tells you it should be. I wanted to help people have the same spark I did, to help them believe in themselves and take control of their own destiny. So many young people, or people of any age really, simply don't realise what's possible because they've never been shown an alternative path.

Interestingly, as soon as I started making even a small amount of money, I found I wasn't as motivated by money as I thought I would be. What really drove me was the idea of helping other people take control of their lives. This multiplied exponentially when I met Simon Squibb four years ago. He was homeless at 15 and built his entire platform specifically to give back to his younger self. Seeing how deeply he cared about the purpose, how much it motivated him despite the money he'd already made, was absolutely infectious. Since meeting Simon, this mission has been front of mind with everything we've built. It's not just about business success anymore - it's about creating a platform that can genuinely change lives and show people what's possible when they take control of their own future.

You invested your mum's £3,000 savings in a marketing course. What's the most important lesson that taught you about risk and investment?
The key difference wasn't the amount - I've spent £3,000 on many things since then with my own money and it didn't have the same effect. When it was my mum's savings, the pain of letting her down was greater than any pain required to build my business. I refused any option other than succeeding because I couldn't waste money she'd saved for me. That £3,000 represented years of my mum putting aside £20 here, £50 there - small amounts that added up over time through genuine sacrifice. When she handed it to me and said "spend it however you like," I felt the weight of every pound she'd saved. It wasn't just money anymore - it was her faith in me made tangible.

The pressure was immense. Every sales call I took for the company I was starting, every rejection I faced, I could feel that responsibility. I took 30+ sales calls before landing my first client, and each "no" stung because it wasn't just my failure - it was potentially wasting her sacrifice. But that pressure became my greatest asset. When you're using someone else's belief in you as fuel, giving up simply isn't an option. It taught me that taking risks creates the motivation to succeed, but it's less about the money itself and more about how much it really means to you and the consequences of failure. The best investments aren't just financial - they're emotional. When someone puts their faith in you, especially someone who's made real sacrifices to do so, you'll move mountains to prove them right.

The Doorbell of Dreams is a unique and creative initiative. Can you tell us more about it and how it came to life as part of your mission to empower entrepreneurs?
It started when Simon Squibb bought a staircase in Twickenham that was up for sale and in the news. His idea was to turn it into a symbol of hope - showing how success is step by step, maybe even an entrepreneur hub. Our head of production, Dudley Dodd, had the idea to put a Ring doorbell on it so people could pitch their ideas. Working alongside our creative co-founder Callum Church, we've since been able to turn these simple doorbell pitches into compelling content that's helped people find mentors, funding, and co-founders.

What makes this so powerful is the contrast with traditional platforms. Unlike Shark Tank or Dragons' Den where only a few people can get in and give up huge equity, anyone can pitch to our doorbell and the best ones are shared with millions online. There's no gatekeeping, no barriers - and anyone can pitch. You never know what connections or opportunities might emerge from that exposure.

We took the concept to the next level when I pitched Richard Branson on his plane. I'd been waiting in the flight bar for the right moment, and when I finally got my chance, he mentioned he'd always wanted people to pitch ideas in his hotel lifts. So I suggested we put doorbells there. To my surprise, he loved it, gave me his email, and after following up a few days later, he replied and looped me in with his amazing team.

Since then, we've installed doorbells in Virgin Hotels in London and New York. Now people in either city can walk up to the lift and pitch their idea directly. Thousands have done exactly that, and the content has been seen by millions across our platforms. It's given entrepreneurs from all backgrounds the chance to get their ideas in front of a global audience.

HelpBnk has really leveraged social media to change the mentorship landscape. How is the platform using digital tools to revolutionise mentorship for today's entrepreneurs?
The beauty of social media today is that it allows you to get in front of the whole world, get your business or idea in front of millions of people just by recording content or writing content and uploading it online. At HelpBnk, we encourage entrepreneurs to leverage this by creating their own content or by pitching to our doorbells, which we can then use to create content to promote their businesses and get them the exposure they need.

But beyond that, the beauty of today's technology is that you don't necessarily need to find one individual mentor to help you grow your business anymore. The traditional mentorship model was quite limiting - you'd have to find someone successful, convince them to give you their time, work around their schedule, and hope they had experience relevant to your specific situation. Now, you can access a like-minded community on a platform like HelpBnk where thousands of entrepreneurs are sharing knowledge, experiences, and advice in real-time.

We've also built tools like our "My Journey" feature, where you can simply explain a bit about yourself and what your business idea is, and it will give you a completely personalised process and guide to grow your business, acting like your own digital mentor that's available 24/7. It's not replacing human connection, but it's giving people immediate access to guidance when they need it most. What's exciting for us is really leveraging the power of community that we can build through creating social media content that people align with and engage with, whilst simultaneously using AI and today's digital tools to create technology that genuinely helps people get the specific help they need to grow their business. HelpBnk's CEO Adam Moss has been brilliant at leading the team and setting the product vision that's made tools like 'My Journey' possible, working closely with our CTO Yordi De Klein to turn these ideas into reality - driving the strategy of how we can use technology to democratise mentorship and make it accessible to entrepreneurs worldwide. The combination of community-driven support and AI-powered guidance means entrepreneurs can get help at any stage of their journey, whether they're just starting out with an idea or scaling an existing business. It's mentorship that scales, mentorship that's always available, and mentorship that evolves with your specific needs.

Reciprocal mentorship is at the heart of HelpBnk. How do you balance the act of giving and receiving mentorship in a way that drives long-term success?
The interesting thing is that as much as people need help and ask for help on a platform like HelpBnk, there are also many, many other entrepreneurs who are succeeding or have succeeded or have been helped by someone who wants to give back. We believe that humans are inherently good, and we've seen that entrepreneurs typically really want to help each other - they just need a convenient way to do so that works on their time schedule. What we've discovered is that everyone has something to teach and something to learn, regardless of where they are in their journey. A seasoned entrepreneur might know about scaling and fundraising, but a 22-year-old might know things about TikTok marketing or Gen Z consumer behaviour that the experienced entrepreneur has never encountered. So reciprocal mentorship works because it removes the traditional hierarchy that makes mentorship feel awkward or transactional.

Our head of community, Adam Smith, has found that the balance happens naturally when you create the right environment for both giving and receiving. On HelpBnk, someone might ask for help with their pitch deck in the morning and then spend their lunch break helping someone else with their social media strategy. It's not a formal system where you have to "pay it forward" - it's just that when you make it easy and convenient for people to help each other, they naturally do.

We've also found that giving help is often as valuable as receiving it. When you help someone solve a problem, you're reinforcing your own knowledge, seeing challenges from a fresh perspective, and often learning something new in the process. That's why we built HelpBnk to make it equally easy to ask for help and give help back. The platform is designed so that you can contribute when you have five minutes or when you have an hour, fitting around your existing commitments rather than requiring a formal mentoring relationship with set meetings and obligations.

Looking ahead, what's the one crucial skill entrepreneurs must develop in the coming years to stay competitive in an increasingly tech-driven world?
Purpose. The biggest thing I've learned from Simon Squibb. It might sound cheesy, but I genuinely think it's the most important thing. AI makes it easier than ever to build a business - you can create websites, write copy, design logos, and even build basic apps without needing technical skills. It's also easier than ever to market your business if you understand social media and digital tools.

So when the barriers to entry are lower than they've ever been, and when AI can help anyone create a technically competent business, what's going to make you stand out? What's going to make you last when the market becomes saturated with AI-generated businesses and cookie-cutter startups?

It's having an authentic purpose to your business that really matters to you. Not a purpose you've created because it sounds good in investor pitches, but something that genuinely drives you. Something that's going to keep you going when you face inevitable setbacks, when competitors emerge, when the market shifts, or when you're dealing with difficult customers or regulatory challenges.

Purpose is what gets you out of bed every day to ensure your business succeeds, no matter what obstacles arise. When you have a real mission behind what you're building, you'll outwork, outlast, and outthink competitors who are just chasing money or following trends. You'll make better decisions because you have a clear north star, you'll attract better team members who share that vision, and you'll build deeper connections with customers who believe in what you're doing.

In a world where anyone can build a technically solid business, the differentiator becomes why you're building it and how much you truly care about solving the problem you've identified. That authentic drive is something AI can't replicate and competitors can't easily copy.