Small Beginnings On A Big Mountain - How Choose A Challenge was born

The story of our company starts with Kilimanjaro. In fact, it starts with two Kilimanjaros: Mount Kilimanjaro, Africa’s highest mountain, and Kilimanjaro Lager, a cold, bubbly and refreshing beverage that shares the famous mountain’s moniker. And it was whilst drinking a bottle (or possibly two…) of said Kilimanjaro lager, perched on cheap plastic garden chairs in a small village on the slopes of the mountain that my Co-founder Charles Milton and I came up with the idea that was to become Choose a Challenge.

Kilimanjaro in the distance overlooking a field with trees and clouds in the sky


Like most small companies when they are forming, we didn’t know what our idea would lead to, whether it would succeed or fail. Back then, we had no idea that we would become a leading challenge event operator here in the UK. All we knew is that we both loved the Kilimanjaro region, and we wanted to bring people to share our passion for this beautiful corner of the world! As we were also part of a group of volunteers that had spent time helping in local schools in Tanzania, we had also seen the benefits that bringing people to a developing country could have, both for the visitors and for the host communities alike. That day, whilst sipping our cold Kilimanjaro lagers, we sketched out a plan for a guesthouse we would build on a small piece of farmland nearby that was for sale. Our idea was that with our own guesthouse, we could ensure that every one of the people we brought to Tanzania would get the very best service from airport-to-airport. At the time, accommodation in Moshi was not of a very good standard, and we believed that having our own accommodation for visitors would be vital. 

We wanted to bring people to share our passion for this beautiful corner of the world!.
— Dan Quille


A few weeks later, we both pooled our life-savings and maxed-out the cash withdrawals on our respective credit cards to fund the purchase of the farmland and the construction of the guesthouse. After the land sale had completed, we transferred all the cash we had available, less a couple of grand that we held back in reserve, to a local building contractor who had promised us that he would complete the guesthouse within the year. We were so excited!

Two months later the building contractor disappeared with all our cash, leaving us with some half-completed foundations that a local surveyor later confirmed would have to be destroyed and rebuilt if we were to complete the building (ironically, the building contractor’s name was Prosper. He certainly did just that from this episode…).

We were very upset and disheartened by these events and the loss of almost all our capital. However, in focussing on the positive we learnt some valuable life, and business, lessons from what happened but, truth be told, it was very tempting to simply walk away from the project after such a major disaster. Instead, we gritted our teeth and pivoted to a new plan. We decided to invest the remaining funds in training some friends who lived in a village near our farm. They were young, like us, but despite being very bright and entrepreneurial, they were unemployed and struggling to support themselves and their families. The money we had was just enough for the costs of training at the local tourism college for them and a few weeks after the builder disappeared, our friends had started their diplomas in Tour Operations.


A few months later we took our first group booking - a group of university students from the UK who wanted to climb Kilimanjaro for charity and go on safari and to Zanzibar afterwards for some ‘R & R’. It was nerve-wracking to be taking so much responsibility for the lives of such a large group for the first time (Kilimanjaro is, after all, a high altitude environment and claims the lives of several climbers each year) but every single one of the participants on this first group challenge gave us amazing feedback at the end of their trip. We knew then for sure that this was it - a challenging trek with an optional extension trip afterwards to rest and relax, raising money for charities who needed the money for their vital work. 


Within 2 years of that first group booking, we had over 500 people signing-up to climb Kilimanjaro with us! It was such a fantastic feeling to know that there were so many people wanting to experience what we had experienced, and to share in the joy of being on Kilimanjaro. We were also over the moon that our friends, and many other people from their villages and the surrounding areas, were benefiting from this large influx of challenge participants. 

Having been involved at the sharp-end of building the challenge itinerary from the ground-up, we could see the benefit all along the supply-chain that was involved (and still is!) in delivering the trips. The employment created for drivers, cooks, porters, guides and admin staff; the money going directly to the national parks service to pay for the park fees, that could be invested in schools and hospitals; the money being spent in the local farmer markets purchasing produce that the trekkers would eat during their trip; even the money being spent in local bars and restaurants by our participants as they celebrated their achievements on the highest freestanding mountain in the world! It was amazing and really reinforced just how much benefit tourism can bring to host countries if managed in the right way.

Our Kilimanjaro challenge became a template for the other challenges we added over the next few years. Charles and I travelled all over the world on recce trips, looking for destinations that would challenge and inspire our customers in equal measure and always ensuring that we found local guides and operators who shared our ethos. We wanted to ensure that the participants we brought to these new destinations had a positive experience and, just as importantly, a positive impact on local communities. When we found the right mix, we set up a challenge there: the Moroccan High Atlas mountains, Everest Base Camp in Nepal (we actually started with an Annapurna trek in the first year, but we soon realised that the demand was much stronger for Everest Base Camp), The Salkantay trek to Machu Picchu in Peru, The ‘Spires of Fire’ volcano trek in Guatemala, the Lehigh Valley cycle challenge in the Himalayas….the list goes on!

2023 marks our 15th year of operation. It’s an amazing milestone for Charles to see as founders, and we’re very proud that over the years through Choose a Challenge we’ve been able to share our passion for challenges and adventure with thousands of people and in the process, brought significant benefit to communities in our destinations. We believe that the original ethos of our first challenge: sharing an amazing challenge destination with new people and, in doing so, bring a host of benefits to both challenge participants and to the people who live and work in the area local to the challenge, is deeply embedded in the DNA of Choose a Challenge.