Freedom from location, surfing optional

E-resident Simon ‘Freedom Surfer’ Vaillancourt helps location-independent entrepreneurs find freedom and fortune

Photo: Simon Vaillancourt

Simon Vaillancourt is a location-independent entrepreneur, who has travelled the world continuously and managed a global portfolio of businesses remotely since 2012.

Through his Freedom Surfer brand, Simon supports other people living or transitioning to a location-independent lifestyle, by providing them with information and support in registering the most relevant and effective business structures for their situations.

Currently in Thailand, Simon is splitting his time between taking care of his own business enterprises and scuba diving in the country’s warm waters. Between dives, Simon caught up with me to discuss his e-Residency journey.


Simon was an early adopter of e-Residency, becoming an e-resident and registering his company Freedom Surfer OÜ in 2016. At that time, there were not too many remote business management options for travelling entrepreneurs. Simon recalls:

“I was excited by the potential of e-Residency as a unique and timely solution for digital nomads like myself wanting to run our businesses on the road.”

Living the life of a travelling entrepreneur was not always in Simon’s life plans and he admits that “a decade ago I would have never been able to imagine where I would be now.” Then, Simon was a journalism and business student in Montreal making a living trading forex. His plan was to get a job, a house and live a ‘normal life’. But a chance hearing on a radio show about the concept of perpetual travel a few months before finishing school changed everything.

Simon hasn’t looked back since, hopping from continent to continent, and living and working in multiple cities each year.

Simon has travelled the world in search of the best business models to set himself and other entrepreneurs free from location. He has figuratively surfed the wave of options available, from Estonia to the US, Bulgaria to New Zealand.

In addition to his Estonian company, Simon has companies registered elsewhere, including in the US, Canada, and the UK. He has been able to pursue this nomadic lifestyle thanks to his various business enterprises. These include company registration and related services for high net worth digital nomads, trading and investing, and maintaining an exclusive, subscription membership-based community platform called The Insiders Club on the Freedom Surfer site.

Freedom Surfer is a site focused on providing resources and services to location independent individuals. It features blog posts, country-specific articles, guides and courses. It is also home to the Insiders Club, a successful community with a diverse membership and active Slack channel, where like-minded travelling entrepreneurs can network and share experiences.

Simon continues to manage membership of the Insiders Club through his Estonian OÜ. It now boasts over 1700 paid members from over a hundred countries — the most popular topics include migration, tax, banking, and how to effectively work and do business remotely.

The Freedom Surfer site will soon be re-launched and Simon is keen to grow the Insiders Club:

“I am just getting started. I have great plans for Freedom Surfer and strongly believe that location independence and what I advocate for is important.”

Simon foresees an acceleration in the growth of the location independent community, which in his view “will be driven not only by a strong desire to travel the world but also by rising tax rates and draconian health-related rules remaining in place in some countries”.

Simon sees the exponential growth in remote work, travelling entrepreneurship, and digital nomadism reflected in the increasingly diverse membership of the Insiders Club and his clients. Up until the pandemic, most were entrepreneurs, primarily in the tech / finance fields. Now, he is onboarding more and more employees working remotely, freelancers and even some retirees.

And with such diversity, Simon has also noticed an increased focus by individuals on freedom of choice — in location, business / tax structures, lifestyles, and living / working arrangements.

About what this means for e-Residency, Simon sees a huge opportunity for the programme and for Estonia to grow its service sector and influence:

“…thanks to thousands of highly creative and driven e-residents from all over the world. It’s a win-win situation that has the potential to benefit all stakeholders.”

80,000 highly creative and driven e-residents have already joined Estonia’s digital nation. Apply now to join them!

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