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James S. York builds bridges between Estonia and America

It is true that if you can make it in New York, you can make it everywhere.

9 min read
© Eleri Ever

Enterprise Estonia has appointed export advisers now in a total of 14 markets – in Asia, there are offices in Singapore, India, China, Japan and the United Arab Emirates. The European offices are located in Finland, Sweden, Norway, Denmark, Germany, France, the Netherlands, and the United Kingdom. The latest addition is the USA’s James S. York who has been the Director of US Business & Innovation for Enterprise Estonia since summer 2019. 

James S. York

James S. York 

 James York is a native New Yorker, and former stockbroker turned professional entrepreneur and marketer. He has been the Head of SME Sales at, an Estonian startup that was acquired by Japanese e-commerce giant Rakuten.

Estonia is like a second home for James as he came to live here ten years ago along with his Estonian wife. Currently, he resides in Estonia as well as New York. One of his goals is to connect and build bridges between Estonia and America so that Estonian entrepreneurs would have more chances to grow and promote their businesses.

‘Life in Estonia’ asked James about his experiences with Estonia and Estonians, his goals in his new post as well as some tips on how to be successful in the USA.

Estonia is often praised for its digital society. They even say that to file an income tax return online takes about 30 seconds. Do you agree? Is there something other nations should learn from Estonia?

No. In my experience, filing your taxes online in Estonia takes three minutes. ‘30 seconds’ is pure marketing hype. But all joking aside, and in all seriousness, the country’s digital prowess is truly impressive and affords Estonia a leading position on the world stage that it has very wisely leveraged for its advantage. I often tell people here in the US that living in Estonia is like living 5 to 10 years in the future, and they are almost always surprised to hear that until I begin rattling off the long list of things that are possible, and taken as normal, in Europe’s ‘best kept secret unicorn hatchery’.

In Estonia, you can easily get spoiled by the ease with which every-thing operates. I know I did, having living there for almost four years. It wasn’t until I moved back to the US that I really understood and appreciated that even when things are ‘slow’ in Estonia, they are still moving at light speed compared to nearly anywhere else on the planet.

And yes, there are many, many things that can be learned from Estonia, and I am glad that Estonia has made itself an open and accessible environment where people can come to learn, experience and better understand what is possible. Whether it is a governmental delegation coming to learn from the e-Governance Academy, or an entrepreneur coming on a startup visa to build their business, or a multinational company setting up a shared service centre – Estonia is a welcoming place with lots to offer.

Estonians have a straightforwardness and candour about them that I really appreciate and I find valuable in business and in life. In fact, I think it’s part of what makes the startup ecosystem so successful.

The threshold for BS is quite low, and people move with a bias towards action and doing, not talking and wishing. Many people might be surprised to hear this from an American, especially a New Yorker… but I very much feel that I learned how to be an effective entrepreneur largely from my experiences living and working with Estonians. And today, working in a very public-facing role on behalf of the country, here in New York, I bring that same can-do, will-do attitude to everything I touch and am using all the country has taught me to help give back to the community and ecosystem as much as I can.

Would you advise starting a company in Estonia and become an e-resident?

The short answer is yes. The long answer is, it depends. Not every business needs a company around it. In the US you can often act as a sole-proprietor or independent contractor, purely as an individual. In other jurisdictions this isn’t the case, or your business requires more structure around it in order to make it a success.

It will also depend on where you work and live, and what sort of tax situation you find yourself in. The tax environment in Estonia is the most competitive in the world, ranked #1 by the OECD. It is also one of the least bureaucratic countries in which to operate, so I recommend it highly to everyone I speak to as an ideal place to set up shop, especially for those who want access to the EU single market in a simple, no-nonsense way.

But ultimately, every business and its needs are different, and deciding whether e-Residency and starting a company in Estonia is right for you is a decision you should make with your co-founders, your investors, and your accountant.

As the Director of US Business & Innovation for Enterprise Estonia, what is your main goal in that position?

I officially joined Enterprise Estonia in the beginning of June of this year. But I applied for the position in the first place because I’ve already been doing similar work for years, and I wanted to do more.

As a long-time mentor with Startup Wise Guys (also known as a ‘mentosaurus’, because I’ve been there for so long), I’ve also been the de facto ‘first call’ for Estonian entrepreneurs coming to explore the New York market, for years.

In my professional life, I found I was also doing more and more to connect the startup ecosystems in both my homes, and in April of 2019 I organised the largest Estonian startup showcase in New York with about 20 teams and supporting organisations participating, with SAP and Google hosting us here in New York.

Now that I am onboard with Enterprise Estonia, and officially opened for business as of late October when we had the opening ceremony for the office with the Prime Minister joining us and officiating, my focus has expanded to be of help not just to the startup community, but the business environment as a whole.

It’s a new and exciting role for me that has already given me great insights into the broader needs of Estonian companies, and afforded me the opportunity to open my network, connections and experience to many more businesses and entrepreneurs than I could have before.

My main goal remains what it has always been – to help Estonian companies reach and expand into this market, and increase the economic ties between both homes. Today, working for Enterprise Estonia from the offices of the Consulate General of Estonia in New York, that means I mainly focus on trade. But there is a large component of investment, business diplomacy, and country promotion that is also an inseparable and valuable part of the mix of my daily work, which ultimately serves to open more doors for the companies I am here to help.

Many companies, startup or not, dream to enter the US market and successfully expand there. What should they keep in mind, if they want to be successful in the US?

The most important thing to remember is that you will need help. The adage of, ‘if you want to go faster, go alone. If you want to go further, go together’, holds very true in this market. Look for trustworthy partners, rely on them, and use them to do more, faster. The USA is not a single market, there are 50 local markets here, each with their own features, rules and regulations. It’s too big of a market to do everything yourself, and you will need to find both borrowed networks that you can plug into, and more leveraged ways of working if you are going to make an impact.

James S. York EAS New York office

Opening ceremony for the Enterprise Estonia New York office with the Prime Minister Jüri Ratas  © Eleri Ever

Here in the US, and other markets, Estonian companies can rely on Enterprise Estonia and its network of foreign representatives, of which I am one. Additionally, either directly or with the assistance and cooperation of an Enterprise Estonia foreign rep, the Honorary Consuls network that is maintained by the Ministry of Foreign Affairs is also a tremendously valuable resource and asset for Estonian businesses looking to expand abroad. And last, but not least, foreign-born and expat Estonians are usually tremendously keen and happy to help Estonian entrepreneurs and individuals at home in any way they can.

It’s also important to come and experience the culture and the environment first-hand before making the jump into this market. American business culture is simultaneously similar and different to that of Estonia, and it’s very important to learn where those similarities and differences fall so that you can better navigate them and avoid some common mishaps.

In an ideal world, when looking for partners, referrals and references are absolutely the way to go. Business is about relationship-building and the ability to leverage existing trust networks is a tremendously powerful skill. You can of course do your research and go purely on the information provided to you publicly on the web, however, that is never a substitute for using real connections, from real people.

Would you name some Estonian startups that have potential in your eyes? 

There are lots of promising Estonian startups! Both in Estonia, and founded or co-founded by Estonians abroad. From those founded in Estonia, I can easily point to Zelos, Entify,, Consorto, Taddy, Modash, Mash Machine, and Lumebot just to name a few.

From those founded abroad by Estonians living here, definitely The Farmer’s Dog, Bolt Scooters and Elip Solutions are the ones to watch. Estonians have a natural knack for entrepreneurship and anytime I see an Estonian-founded or ecosystem-based company coming down the pike and heading for this market, I get excited and I know that great things are on the horizon for them.

Source: Life in Estonia magazine

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