Interview with Simon Shaw: Professional Sailor, Yacht Racing Consultant and Founder of fiftymedia


Amongst Simon Shaw’s sailing accolades are 2 World Match Racing Tour Championships, 7 Individual World & Euro Championship Win and acting Olympic Tactical Coach. He is a passionate competitor and has over 15 years of professional sailing experience. He is also Founder of fiftymedia, a social media agency with expertise in enabling businesses to understand and use social data to derive real value from their social followings. We sat down with Simon to discover more about his sailing experiences and fiftymedia.

You have achieved an enormous amount in your life. Did you start sailing from a very early age?

I started sailing really before I could walk or talk. Sailing was a family passion and just a way of life. My dad was a great inspiration for me on the water and dedicated a lot of time building up my passion, confidence and skills but above all my enjoyment of sailing.

You have been all over the globe sailing at a number of the most prestigious events such as the America’s Cup. What has been your best race to date and why?

There is something incredible about being asked to join an America’s Cup team and for me this event will always have a place close to my heart. Half way through my time at University, I was asked to join GBR Challenge, the British team competing for the 2001/2 America’s Cup in New Zealand. It took a lot of staying power to hold off packing my bags straight away until graduating a year and a half later. It was an interesting decision to make. In todays’ world, I would almost certainly have turned professional a year earlier.

There is no question the technical foundations that I built up prior to going into professional sport have helped me to create fiftymedia, the technology and consultancy business I founded in parallel with my life out on the water.

My favourite race was probably at the Pacific Cup racing the IACC version 5 America’s Cup boats. We were representing team China and had an incredible race, trading blows with Team New Zealand, and BMW Oracle.

What is your favourite boat to sail?

I am not sure about a favourite boat as such, but my most enjoyable sailing has always been match racing. This is where only two teams are in the race and the boats’ only objective is to beat the opponent around the course. As a style of sailing, this is generally regarded as more technical/ analytical as well as being more combative. I have been fortunate to have the opportunity to race at the highest level in this area of sailing for over a decade, as well as winning two World Championships.

Competing in an international sport at a world-class level allows you to witness firsthand how people think under pressure in a team context. In 2011, I raced with a Japanese backed team with an Australian Skipper, Peter Gilmore. Despite never having been to Japan, the level of insight into the ethos, values and precision of how we worked together was an experience that would be hard to recreate.

In the property world, Mike Slade of Helical Bar is my hero with his amazing property company, support of Land Aid and his yacht, Leopard of London. Do you have a hero yacht owner?

Mike is an incredible individual and what he has achieved on the water, as well as how he runs his sailing project is world class. Sailing does give you incredible access and it is easy to take for granted the connections to some of the most wealthy and powerful people in the world.

Sailing has certainly opened the door to a number of key business contacts and advisors. However, most important are the friendships and guidance from people who are exceptional in their field as they open your eyes to possibilities and opportunities. There are a number of key owners that have helped me establish fiftymedia into a social media technology company. We work with some of the top businesses in the world that want to interact with their clients in a variety of different ways.

Who do you think builds the best yachts?

Despite my racing background, I am a real fan of classic boats. I adore the J-Class and have been lucky enough to race on Velsheda, winning our class in the JP Morgan ‘Round the Island’ Race. Driving a boat like that is truly incredible.

Sailing is all about working as a team against all the elements. How does this team management reflect in your business?

Sailing is one of the most team-focused sports in the world and requires a huge amount of work “off the field”. Similar to

Formula 1, the technology and development is highly analytical and managing the coordination of highly skilled people with wildly differing skill sets is key to the success of the project.

Trying to build a business that genuinely finishes first in its field is the same as being world number one on the water. The first strategic decision we made was trying to keep the team small enough so that we can react, change and pivot as our technology and different social media platforms evolve. We help businesses identify and connect with new customers over social media. We are now working with some incredible brands and the future is very exciting.

You have mentioned that your day job is with fiftymedia, a leading social marketing agency with a raft of big name clients such as Abu Dhabi Ocean Race and Oyster yachts, as well as luxury with Rosewood Hotels and the best club in Morton. How does your experience of sailing relate to the big wide world of the Internet?

I think the key area is the pursuit of actual results and not just hot air. “Does it make the boat go faster?” I think this is a mantra we have tried to apply to the development of fiftymedia as well as the focus of our efforts on behalf of our clients. Social media is like any other type of sales and marketing, led by the delivery of genuine results.

I am a great believer in social media, it helps you target and understand your audiences. The fashion industry has embraced the blogger. Other industries still are very wary. How do you overcome their fears?

One of the key areas is to help our clients reach a point where they can understand the potential of how these new tools relate to them. We help them to take that step, which will change the performance of their business. It is also important that we are there as a team to support their activities along the way as well as deploying our targeting technology to drive audience growth and ultimately results. When social media really starts to work for a business, normally people’s fears subside.

You are obviously highly competitive in sailing. Are you the same in business?

Business is similar to a sailing race. You have to decide on your strategy and make sure your team is motivated and moving forward.

Identifying the key moments that will define success and failure and execute them succinctly. The difference is that the “race” plays out over a much longer period of time. I have had to learn to be more patient with progress. Seeing the opportunities around me in London from a business perspective is just as exciting as winning races.

Can you recount one of your most dangerous sailing experiences?

When we were younger, we took part in the Tour de France, a sailing equivalent of the famous cycling race. I was the helmsman of the British entry in that year, in the build up to joining the America’s Cup Team.

We were sailing in very strong downwind conditions at night in heavy seas. The Mumm 30’s we were racing are extremely fast and exciting but unstable boats in those conditions as we were pushing for all we were worth. My co-skipper and good friend was up on the front of the boat (where it is wettest).

I remember surfing down a wave and as we were pushing the boat as much as we could, we actually buried the front of the boat. It was an intense and scary experience. 

Aside from coaching through the Olympics, what has been the highlight of all your achievements?

The 2007 and 2008 World Match Racing World Championship was probably one of the most special sailing moments. The sailing was really close on both occasions and we managed to come out on top both years.

I have won all 4 classes at the International Maxi Association Championships in Sardinia(Maxi Class World Championships). The sailing in that part of the world is incredible. The combination of incredibly large boats and such a dramatic coastline makes for very exciting racing.

What is the strangest tweet you have ever been sent?

One of the amazing things that come from social media is the connections and contacts. I have managed to secure contacts that have lead to personal sailing sponsorship and all kinds of ambassador style relationships.

Who inspired you to sail?

I think you end up with different sources of inspiration. Clearly at the start of my sailing journey it was my father. A prominent sailing family friend, Tani Bassadone was incredibly supportive as well, putting time and energy into helping me raise my game to compete nationally.

I went to school with the late Andrew (Bart) Simpson. Bart’s successes in the sport of sailing need no introduction, however his impact on the start of my sailing career was huge. His friendship, skills and support gave me the platform to launch my professional sailing career.

What does the future hold?

Fiftymedia is starting to really fly. I am involved in the startup and development of one of the biggest crowdfunding platforms launched in the UK, which is also going very well.

On the sailing side I have had the opportunity to do some TV presenting. I have really enjoyed this as it is another way of moving forward that area of my sport and I hope to expand it over the next few years.

Currently I have a very exciting new carbon fibre 85-foot catamaran going through its design finalisation, which should be launched in the later part of 2017. It should be capable of breaking some world records, which is really exciting.

For more information on fiftymedia, please visit: www.