Drawing on his digital expertise, Caspar co-founded Influencer.com, a global influencer marketing company with over 150 employees, where he currently serves as CVO and board director. He also co-founded MVE Management in partnership with Endeavor Group.

As a General Partner at Creator Ventures, a VC fund with $20 million under management, Caspar invests early in the technologies behind Internet culture. He also serves as Chairperson of The Prince’s Trust RISE Board, has been featured in Forbes' 30 Under 30 for his contributions to media, and is the co-owner of the fastest-growing student accommodation company in South Africa, Proper Living.

In this conversation, Caspar shares his journey from YouTube to entrepreneurship. He discusses the challenges of leadership, the importance of confidence and resilience, and what keeps him motivated as a founder. He also talks about the technologies and trends he’s excited about, including the potential of AI in education and content creation, and offers honest advice for aspiring entrepreneurs.

How have you found the entrepreneurial world?

I’ve found it very exciting. When I was younger, my parents started a chocolate factory, and I was a massive fan of Richard Branson – still am, in fact. I even used to write him letters. So, I always thought being an entrepreneur was awesome. Growing up with a chocolate factory in the family, I used to go to the market with my parents. It was a very small operation in a small town, and we would sell chocolates together. I even set up my own little stall once, selling books from our house that no one was reading – a little bookshop at the market. I always tried to find entrepreneurial ways to do things.

What have some of the biggest challenges been in your ventures and for you personally?

One of my biggest challenges personally was building confidence in my own ideas – or rather, in my ability to lead others. I used to think that leadership meant having the smartest ideas or the best solutions, but I’ve learned it’s more about listening, empowering others, and hiring great people. The real trick is building a team where people are not just capable but can also advise and build the company alongside you. If you can get that right, your own insecurities or lack of ability in certain areas becomes less of a challenge.

And then there’s always the constant battle to grow revenue. Every year, you’re trying to improve, to scale. It's never a straight line. Even when something is going really well, it just means you have to do it even better the next time. So, it feels like you’re always trying to run faster than the treadmill, and the bigger you get, the faster that treadmill moves.

What does a typical day in your life look like as a founder and creative?

A typical day in my life looks quite different depending on what’s going on. I’m usually in the office in London, working across my various businesses. There’s a fair amount of meetings, but I also spend a lot of time writing, researching, and solving problems – and of course, replying to emails. I meet a lot of people, attend events – it’s a mix, really. Every day is different, but even when I’m not at the office, I’m on my phone working. I actually love it – I enjoy working through tasks.

How do you stay motivated and focused when managing multiple ventures?

In terms of staying motivated and focused, I don’t really struggle with it. I just enjoy it. I wake up and want a challenge. Even with working out, I enjoy how it makes me feel afterwards – and the same goes for work. Even when something’s difficult, I like the feeling of accomplishment afterwards. If I spend a whole day relaxing during a workweek, I don’t feel quite right – unless it’s the weekend, when I properly switch off. But I like feeling productive, and I think that’s what keeps me going.

Looking back, is there anything you would have done differently?

Looking back, if I could do something differently, I’d have started earlier. Compounding is incredibly powerful, and the sooner you begin, the more time you have to benefit from it. That said, I’m lucky – I started fairly young and still have time ahead of me.

What has your favourite part of the journey been so far?

One of the standout moments of my journey was meeting the Queen. That was through the Queen’s Young Leaders initiative, which I worked with. It was a real pinch-me moment.

More generally, I love the feeling of having completed something difficult – coming through challenges always makes me feel proud.

You’re a partner at Creator Ventures, investing in the technology behind Internet culture. What trends or technologies are you particularly excited about right now, and why?

Right now, I’m particularly excited about what AI is doing in the education space. In the coming years, I think people all over the world will be able to access high-quality, personalised education – whether it’s learning a new language, accountancy, or law. Everyone could have access to the best tutors at a much lower cost. That kind of accessibility is huge for social mobility.

I’m also fascinated by how AI is transforming video and content. Being able to analyse content at scale – without needing a person to do the work – allows for incredible insight. Companies doing that sort of thing are really interesting. It makes marketing more effective and helps with creativity, idea generation, and engagement analysis, all of which are crucial in the spaces I work in.

Where do you see yourself and your ventures in the next five to ten years?

Looking ahead, I hope to be doing more of the same, but on a slightly bigger scale. I really enjoy working within the creator, entrepreneurial, and investment space – it’s where I feel most energised.

Finally, what advice would you like to give other entrepreneurs?

My advice to other entrepreneurs would be: don’t follow too much advice. Be inspired and learn from others, yes – but remember that everyone’s journey is unique. It’s okay to do things differently. Also, start sooner rather than later. Don’t wait for the perfect time or perfect idea – just try something. If it fails, you can start again. I know it’s easier said than done, but nothing worthwhile is easy. You miss 100% of the shots you don’t take.

This article originally appeared in the May/June 2025 issue of Startups Magazine. Click here to subscribe