• Alumni
OM Rob Woodhead shares his entrepreneurial journey during Global Entrepreneurship Week

Last week marked Global Entrepreneurship Week, an initiative initiated by the Global Entrepreneurship Network in 2008. During this event, we had the opportunity to chat with OM Rob Woodhead, gaining insights into his entrepreneurial journey. The week is designed to inspire individuals, especially the youth, to embark on entrepreneurial ventures, which aligns seamlessly with the values embraced by Rob. 

Rob wears two hats: he's the visionary behind Old. St, an organisation dedicated to empowering innovators through technology, and he's also the driving force behind the Founder’s Community- a monthly gathering that provides a casual setting for founders and individuals in the tech ecosystem to come together, share experiences, and broaden their networks. It's a space where people can connect, hear about each other's journeys, and build meaningful relationships in a laid-back environment. 

We chatted with Rob about life during and after Millfield, and explored how the skills he picked up at school played a big role in building his business, and personal journey. Plus, we got some great advice from him for current students and OMs who are thinking about diving into the business world. 

Please tell us a bit about Old.St!

After a bit of a career shift, I now run a business called Old.St Labs (www.old.st), helping people build technology products. Early-stage businesses and innovating companies work with us to develop mobile apps and web apps. It's the most enjoyable job I’ve ever had as I get to meet people from all over the world that have a passion to build something that they are really excited about.  

We’ve built all sorts of things, a social platform for military veterans, a drug / disease matching engine powered by AI, a customer portal for an electric vehicle chargepoint business, and 30 other interesting products. No two days are the same. 

We are based in London, but we are an entirely virtual business, with no physical office, and the majority of my team is in the Philippines. It makes for an interesting business to manage, but I get to go out there quite a lot, which is amazing. 

There are a lot of outsourced businesses around, I think we are able to provide a much better experience to our customers as we combine the experience from the UK with the quality and competitive pricing from the Philippines. 

How was Old.St born - what was your inspiration behind it? 

After a long and fairly stressful career in finance, in 2015 I decided I wanted to try something completely different and moved into the world of startups and technology. It probably wasn’t the most obvious move as I’d never started a business before and don’t know how to write code, but I saw that as a challenge, and I learnt a lot in the process. 

My first venture was a technology business focused on the electric vehicle industry, trying to assist fleets in their transition to electric. It was incredibly interesting but one of the major headaches I went through was trying to outsource the development of the app I was trying to build. There didn’t seem to be anyone helping tech novices get their ideas off the ground without breaking the bank. Outsourcing technology meant me, a tech newbie, talking directly with a developer from a different country. Trying to communicate about something I didn’t really understand and not in the developers first language, was incredibly hard. 

So, when that business didn’t work out, I saw an opportunity to build the business I wished would have been there to help me before. One that explained all the technical jargon, guided me through the complex decisions, and helped me avoid the pitfalls when building tech. And so Old.St Labs was born.

Please tell us about your time at Millfield! 

I joined Millfield prep (Edgarley as it was then), in 1990, when I was 9 years old. I was nervous about starting as it seemed like a big scary place, but as soon as I joined, I loved it and never looked back. I was there all the way through until I was 18. Those 9 years had an immense effect on me, one that I’m aware of even now. I’d say it certainly shaped me as a person. 

The main things that I remember from school are playing a lot of sport, practically every day; hanging out with friends that I still have now and trying to keep up with homework. It's only subsequently that I’ve realised how good the opportunities were at Millfield compared to other schools. In some ways I’d have loved to take more advantage of the art / music / theatre, but then there were only so many hours in the day. 

My father was a teacher, Mr Woodhead, or Block as the Butleigh boys used to call him. This gave me and my sisters a unique perspective on school, as although we were in a boarding house, I lived at home.  In a way, the best of both worlds, but also one where everyone knows your dad, which can have its drawbacks. 

I also remember there being a lot of great teachers. Of course, there was the odd tough one, but on the whole, I always felt like they really cared about my development and helped me navigate those difficult formative years. I also remember transitioning from being told what to do a lot, to being given responsibilities and trusted to make decisions for myself, which definitely prepared me for later life. 

There were some clear highlights of my Millfield time, like being a part of the treble winning 99 hockey team, the undefeated U16 rugby 7’s team, being Head boy or getting the A Levels I needed to get into Oxford. But what I really look back on fondly are the smaller moments. Things like walking to class with a Tipp-Ex graffitied folder under my arm with very few cares in the world, trudging to games on Butleigh fields in the sideways Somerset rain, or forgetting the words to some Latin song during House Choir Competition. 

What started as a big scary place turned into a wonderful place to grow up. 

Did attending Millfield School equip you with any skills that contributed to the development of your business and personal growth? 

There are so many parts of my Millfield journey that have given me skills and abilities that I have taken into later life. 

Obviously academically it gave me a huge boost. When I started, I had real trouble reading and writing. I had extra English classes from the outset which gave me much more confidence and brought me up to everyone else's standard after a few years. I also developed a real interest in science at school which I went on to study at university. That not only gave me a great grounding in maths, but also a way of thinking about things methodically, testing ideas and using data to make decisions. All of which are helpful when building a business. 

I also gained a huge amount from all the sports I played at school. There have been many books written by far better sportsman than me about the benefits sports brings, but some of the major ones I have experienced are: understanding the crucial part training and preparation plays in the outcomes you seek; the ability to be part of a team, finding your role, however small and doing it the best you can for the benefit of the greater goal; learning about and growing into leadership and getting the best from your team; understanding and accepting how to both win and lose; the confidence gained from learning and training in something that you have put your heart and soul into, and the enduring bonds formed by being part of something that was difficult to achieve. 

On top of all these, learning sport at Millfield gave me a platform on which to build friendships across the world, and these friends were the ones that supported me in the early days of my business. My business network is underpinned by the sport I have played, and I have a few long-standing clients that are a direct result of enjoying being part of teams throughout my life. 

Beyond the academic and sporting side of Millfield, I think the school also instilled an inner confidence in many, even if unknowingly. There is definitely a sense of being different as an OM or Miffy, something that sets you apart, different to other traditional boarding schools. I wonder if it's driven more OMs to become entrepreneurs than other schools? 

What advice would you offer to others, both current students and OMs on starting up a business/focusing in school?

I think I’d say make sure you take as many opportunities as you can at school, Millfield offers so much, you have loads of things to try and see what you are passionate about. Try that musical instrument, have a go at the coding club, see if archery is your thing, give Japanese a whirl. As you get older, opportunities like these diminish and I’m so thankful that I got to do so much growing up. 

One huge opportunity I had from Millfield was to be part of the charity Students Partnership Worldwide, which took me to Nepal pretty much straight after I finished school. I had an absolutely incredible time out there, learnt a huge amount about the world but also myself, and came back a much more mature person. 

And for those looking at starting a business, I’d offer these bits of advice:  

  • Don’t be afraid to fail, but learn from your mistakes 

  • Read books around the subject, a good one I always recommended is The Lean Startup by Eric Ries 

  • Find out what you are passionate about and do something related to it. The passion will keep you going when times are hard. 

  • Find a problem to solve and then figure out everything about that problem, why it's a problem, who has the problem, what do they do to solve it at the moment. The more knowledge you have about it, the more likely you are to come up with a good solution. 

  • Talk to people about your idea, get other points of view. You don’t have to agree with them, but understanding how people see your solution is crucial to how you sell it 

  • Hopefully that's helpful as a few things to start thinking about initially. 

Please tell us more about the Founders' Community! 

As the pandemic was waning and people were starting to meet up once again, me and a few friends wanted to reinvigorate the tech community we’d known before everything had closed. So we started a small monthly gathering, in a pub in Shoreditch, East London, and called it ‘Tech Startups in the Pub’. 

The first event had 5 people attending, but it was fun, and it was nice to catch up with friends working in a similar space, hear how they were getting on and meet a few new people. The main point was to create a relaxed environment where founders and anyone working in the tech ecosystem could come and meet others in a similar position. 

We have now been running the event monthly for 18 months and it has grown organically from those 5 at the first event to now regularly getting 60-70 people coming each month. We have even expanded to a few other cities, including Madrid, Tel Aviv and Manila. 

I think being a founder can be a lonely experience and so meeting others who are going through the same journey can be incredibly helpful. We also try and act as facilitators for introductions, as normally, networking events can be a bit like finding a needle in a haystack, so we try to make sure people are introduced to others that we think could be useful. 

We now have a recurring community of people who return to give updates on their progress with their business and share their successes and issues, with a supportive set of people ready to offer help or advice if needed. 

We run the event on the third Friday of every month at the Windmill pub in Shoreditch, details of the next event are here: https://www.eventbrite.co.uk/e/tech-startups-in-the-pub-tickets-391540296567 
There’s already one regular OM, it would be good to have some more!