Simon Armstrong

Be open to change. People, places, trends, instincts, in short – life, can all open your mind to new worlds, which in turn allow you to realise different opportunities.


Simon Armstrong was born in York, UK and grew up in the Northern English Counties of Yorkshire and Lancashire before studying at the University of Liverpool and University of Central Lancashire. Following his graduation, Simon worked as a Sports Journalist at the Press Association but at the age of 23, determined that his future lay in a foreign classroom and succumbed to his desire to teach and travel.

Working as an ESL, English Language and Literature teacher and Coordinator, he worked at international schools in Indonesia, Switzerland, Brazil and Canada before settling in Prague, Czech Republic. In the Ancient Czech capital, Simon also discovered tour guiding as a means to satisfy his thirst for history and showmanship on the weekends.
This foray into the travel and tourism industry, combined with his extensive knowledge of the International Baccalaureate program led him to establish CAS Trips in 2013.

CAS Trips is an educational tour operator, seeking to redefine the concept of educational travel by tackling the UN SDGs whilst engaging in volunteer projects inspired by the notions of Creativity, Activity and Service. Working with schools from all over the world, CAS Trips aim to make a genuine, sustainable impact on school trips.

Simon currently lives and works in New York, USA as CAS Trips look to continue their recent trend of global expansion.

Where did the idea for CAS Trips come from?

After leading one too many underwhelming school trips during my career as an international school teacher, I was moaning about the lack of meaning and depth of one particular trip to a friend when he turned to me and said ‘why don’t you just design the next one yourself?’ It all seemed so obvious and simple in that moment as it came to me in a flash: why not combine the three elements of the International Baccalaureate’s CAS components (which entails Creativity, Activity and Service) to truly discover and engage with a destination? And so the basic CAS Trips model took shape.

What does your typical day look like and how do you make it productive?

I love to make the most of the morning. Being presently based in New York, watching the city wake is truly inspirational so if the weather permits, a morning bike ride, run or gym session starts the day off right. A highly-focused morning email blitz usually gets the admin side of my work out of the way, leaving the afternoon for me to get creative. For me, old-fashioned to do lists and ineligible scrawlings pinned to notice boards keep me on track.

How do you bring ideas to life?

The creative process of defining new concepts, activities and partnerships is a highly energetic and driven process and cannot work without partnerships. Ideas we share with our partners often buck the trend and we ask them to take a leap of faith with us. Our incredible charity, NGO and service partners are vital to what we do so for us, it is equally vital to approach them with a refined, well-thought out idea and rely on our passion and commitment to persuade them to get on board. Genuine, open communication, with no ego or pretence is equally as important to ensure a level playing field.

What’s one trend that excites you?

Sustainable travel. Purely and simply. Travel is more accessible than ever and the potential to make a genuinely positive impact whilst discovering the world, is huge. People hear ‘sustainability’ and instinctively think of the environment which is of course extremely important but travel can also be sustainable and enriching by connecting with and contributing to local communities which is a win-win for everyone!

What is one habit of yours that makes you more productive as an entrepreneur?

Tea! Naturally – I am British! I used to drink bucket loads of black tea with milk. But, just like too much coffee, I soon realised what goes up, must come down and was consistently exhausted by mid-afternoon. A few years ago I discovered green tea with ginger and lemon and it has been a revelation. Two in the morning, one after lunch gives me energy and focus consistently throughout the day.

What advice would you give your younger self?

Trust your instinct. I used to always question every single decision which invariably slowed everything down to a snail’s pace. Through experience I have learned to trust that inner voice and, when in doubt, I take counsel and trust those outer voices of friends, colleagues and loved ones who I know I can trust as much as myself.

Tell us something that’s true that almost nobody agrees with you on.

Cheese. Is. Disgusting! Sorry, I know I am in the huge minority here but I was traumatised by my father’s obsession with overly-ripe blue cheese from a very young age and cannot abide it!

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Be open to change. People, places, trends, instincts, in short – life, can all open your mind to new worlds, which in turn allow you to realise different opportunities. The age we live in is rapidly changing the basic ideals and concepts that previous generations were built upon, principally through technology and the access to knowledge. In change there is opportunity. If you’re one of the first to see the change, by definition you are one of the first to see the opportunity.

What is one strategy that has helped you grow your business?

Connecting people through passion. When you explain and explore your concept or idea and you feel someone gets it, don’t leave it at that. Push the discussion further and discover just how much you align. If the alignment is something you can’t ignore, trust your instinct and start to explore ways you can work together to achieve that common goal. More often than not, you’ll find business can also be run by your heart and not just your head.

What is one failure you had as an entrepreneur, and how did you overcome it?

Whilst living in Sao Paulo, Brazil, myself as a qualified English teacher and my good friend as a qualified football coach were convinced we had found a gap in the market – teaching English through the interactive medium of football. We worked for months to develop a fantastic curriculum and took it to a market obsessed with football and with a need to learn English. What could go wrong? Well, we fundamentally misread the market. At that time, the economic situation in Brazil wasn’t quite ready for such a progressive educational shift from the norm. Lesson learned? It’s not all just about the quality and your belief in the product – it’s also about analysing the socioeconomic factors.

What is one business idea that you’re willing to give away to our readers?

See above!

What is the best $100 you recently spent? What and why?

A couple of nights on an Airbnb sailing boat! For my wedding anniversary, I surprised my wife and took her for a weekend trip off the coast of Rio and it was truly memorable.

What is one piece of software or a web service that helps you be productive? How do you use it?

Trello. Logistics and organisation are vital to what we do and Trello allows us to ensure everyone is reading from the same page. It is intuitive, comprehensive and an absolute God send.

What is the one book that you recommend our community should read and why?

100 years of solitude” by Gabriel Garcia Marquez. So often in life we can get entrenched in the dogma of day-to-day tasks and we can become blind to life’s magic which we felt so naturally when we were younger. But Garcia Marquez’s beautiful style rekindles that childhood spirit or curiosity and adventure and makes you see the world through fresh eyes.

What is your favorite quote?

My life has taken me to live in some of the most breathtaking places in the world and each has taught me something special. For this reason I can say, without cliché, my favourite quote is ‘Travel is the only thing you can buy which makes you richer’.

Key learnings:

  • Business can and should be run from the heart, just as much as the head. Trust your instinct but find the balance by taking counsel from trusted colleagues and loved ones.
  • No matter how much faith you have in your product, perform a detailed socioeconomic analysis of the market before jumping in at the deep end.
  • Drink green tea and exercise – healthy body, healthy mind!


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