Delivering Results: P2P Startup sailsquare Navigates Toward Success

Simone, what is sailsquare all about?

Sailsquare connects boat-owning skippers with travelers enthusiastic about living an experience at sea. Through a peer-to-peer platform, people can take part into sailing experiences listed by boat owners.

How did you discover the need for platform? What everyday problem are you solving?

The offer in nautical tourism mainly consists in renting leisure boats and targets experienced users able to steer a boat or, at least, to understand sailing basic skills. These users directly consult charter companies or brokers but they often have troubles in finding a minimum number of people to complete the crew in order to make the boat renting cost affordable.

Tour operators that provide sailing holidays on the other hand are often tied to a go-to market strictly related to the area they operate in, thus not really scalable. In addition, they have a rigid and scarcely varied offer due to their business model (boats allotment), able to satisfy a reduced demand portion (mainstream offer). As a consequence, more than 70% of total demand for sailing holidays is not properly fulfilled.

Tourism startups often struggle with ferocious competition. How do you make sure you don’t get lost in the shuffle?

Our luck consists in being the first one with the right insight, which is to apply peer-to-peer model to nautical tourism in a successful way. Since we started, dozens of startup companies entered the same market: the only way to still remain the leader is to go on running faster than the others, learning from past experiences, innovating and improving our service with resolution and determination.

In what ways do you measure your success? How do you manage to stay on focussed?

At sailsquare we are very careful to measure any phenomenon that may be useful to understand how the platform is being used and how we can improve our service. There are many tools to measure the success rate: in my opinion, the best is the one measuring the evolution of the recurring customers rate over time. Not only is this a very important metric helping us understand how much value a user can generate over time, but also it is the best measure of users’ satisfaction towards the service we offer.

Bootstrapped or financed: What fuels your startup now and what will in the future?

We have created sailsquare with our own savings, positive about our vision and determined to turn what was only a dream into reality. Along the way several business angels have supported us, infected by our enthusiasm and by the results we demonstrated to be able to reach with limited resources. Now we are ready for the big jump, aware of the value – not just financial – that an institutional investor can give us in our internationalization process.

What were the biggest challenges you faced building sailsquare?

The biggest problem one can encounter when setting up a startup is to convince all stakeholders – investors and team members in the first place – of the potential of what you’re doing, without having virtually anything, but an idea. I think this is the most difficult obstacle to overcome.

Certainly every stage of the development of a startup poses challenges to deal with, but if you are able to demonstrate with the results that the road you are taking is the right one, everything becomes easier.

Convincing team members of your vision is one thing – another one is how they can convince you?

In recent years I’ve put together several teams, usually where there were no groups before. Thanks to this, I’ve learned that hiring skilled people is worthwhile in short-term periods, but if you are focused outward you will soon understand that looking for a specific cultural fit and the attitude toward the job and colleague’s one is the most important factor in choosing your coworkers, as well as the only way to build up a team rather than just a group of people working together.

Being passionate about your job, being a curious and a detail-oriented person as well as having great team-working skills are the the essential traits for those who want to join our crew.

Why would talents join your crew? What’s in it for them?

We are still a small team, where everyone’s aid is extremely important. I truly believe that joining the crew in this particular phase of our development is a unique occasion for an ambitious person keen on being on the front line in order to lead our project to success.

Besides, being passionate about sea and sailing can surely be a motivational factor, as it was (and still is) for many of the members of the crew.

What was your most memorable moment so far?

Our first customers, the compliments received on the service, good earned value management, investor’s trust and every little achieved goal is a big and satisfying cause. They all represent a fundamental moment to renovate team’s motivation from the inside and not to letting go because of everyday issues.

Last July our transactions counted nearly €700k, which corresponds to the total amount of 2015: this is an important goal proving that we are following the right path and that our efforts have been rewarded.

What is your 7-year vision for sailsquare?

Our dream is making sailing holidays affordable to everyone, by giving people from all over the world the possibility to share unique experiences.

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