James York: Is the US market right for your Startup?

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

Today, James is the Director of US Business & Innovation for Enterprise Estonia.

Estonia is like a second home for James. One of his goals is to connect and build bridges between Estonia and America, so Estonian entrepreneurs would have more chances to grow and promote their businesses. From this article, you will find out what is his main goal as the director of US Business & Innovation, what are the biggest mistakes that startups do when they expand their business operations in the US and many more.

You're not as well known (yet) in the public, so now you have a good chance to introduce yourself. Who you are and what you do?

That’s a long story, and the beginning is usually a good place to begin so let’s start there.

I’m a native New Yorker who began his career in New York following university as a licensed stockbroker, working on the 40th floor of the World Financial Center. I then moved into real estate, first working in residential brokerage selling and renting luxury properties in one of the world’s most iconic cities, and then commercial property management where I had the privilege and responsibility for managing one of the highest-profile public real estate portfolios in North America’s largest public transportation system.

Nearly a decade ago I moved from New York City to Tallinn with my wife, who is Estonian herself. And what I found there changed the direction of my professional life, and I’ve never looked back. When we arrived, I went to work for what was then my first start-up – Fits.me. From there it’s been an exciting journey working with startup and innovation companies across a myriad of sectors and exploring their strengths and challenges, and always working with an eye towards trying to bring the best of all worlds together.

While I’ve been living and working again in New York City for the past 5 years, I never truly left Estonia and am someone who will always have a foot in both markets. As a native New Yorker with an Estonian family, who’s become an adopted member of the Estonians living abroad community, my passion – both personally and professionally – has become building bridges and creating new connections and opportunities between my two homes.

Having been an independent management consultant and then running a strategic marketing agency, I have experience across a wide range of sectors. Today, in my role at Enterprise Estonia here in the States as an Export Advisor and the Director of US Business & Innovation I find myself with a platform to do more of that work in a way that allows me to make an even larger impact than I had before.

I am also an active mentor with Startup Wise Guys since their second batch and was invited to join the University of Tartu marketing department as a guest lecturer last year, with a focus on digital and growth marketing for startups.

What is your main goal as the Director of US Business & Innovation for Enterprise Estonia?

I officially joined Enterprise Estonia at 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 organized the largest Estonian startup showcase in New York with about 20 teams and supporting organizations participating, with SAP and Google hosting us here in New York.

Now that I am on board with Enterprise Estonia, and officially open 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 allowed me 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.

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, which 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.

Could you walk us through how does your average workday looks like?

There’s not really a “typical” day. In the five or six months since I started working with Enterprise Estonia, I’ve been to 7 cities on two continents; helped and have (or am currently) worked/working with more than 30 Estonian companies, and counting; have hosted the Prime Minister, the Minister of Education and Research, along with more than 10 Estonian companies across 2 cities; as well as some other cool stuff that I’m really excited about, but won’t discuss here because I work for the government.

I usually take early calls with Estonia from home given the time difference, and then make my way into the office which is at the Consulate General of Estonia in New York. I work very closely with the Consul General in my daily work, and we make a great team! It’s a fascinating experience to get insights into how a diplomat’s world works and to find all the interesting areas where our mandates overlap and to see how we are able to do more together.

There’s also a fair share of paperwork, too. But that’s to be expected and would happen anywhere. But the one thing that always holds true is that I wake up and go to bed each day loving my job and the work I’m able to do, building stronger ties and greater cooperation between both my homes.

It’s a dream for many companies, startup or not, to enter the US market and successfully expand there. What should Estonian companies do and keep in mind, if they want to be successful in the US? Any tips and tricks?

There is a lot to keep in mind when looking towards this market. More than we can reasonably cover here, for sure. But the three main things I would urge companies to keep in mind if they hope to be successful here are the following:

The US is not a single market, but rather 50+ different markets comprised of States, cities, municipalities, and economic regions that all have different legislation, taxation, and nuances to doing business. It’s important here to know where (sometimes very specifically) you want to do business here.

The US is not a DIY business environment. Given the complexity of this market, and the different legislative, tax and cultural layers you will find, don’t underestimate the need for relying on different service providers to help your entry. From lawyers and accountants who can help with corporate governance and tax issues, to customs brokers, local salespeople, and native marketers you will need people here to help you. How much of a footprint you need to maintain in the States will usually depend on how expensive and/or complicated your product is. If you have a self-service, self-sign up SaaS with a low monthly subscription, for example, you can get away with less help and possibly even avoid having to maintain a local office or team in the States (depending on your scale and size). The more expensive or complicated your product or service becomes, however, the more help you will need, and the more of it you will need to be local to the US market if you want to make it a success here. 
The more expensive or complicated your product or service becomes, however, the more help you will need, and the more of it you will need to be local to the US market if you want to make it a success here.

3. Be patient and don’t try this market casually. Everything will take longer and be more expensive here than you initially thought. So while the US is full of opportunity, it is not for the impatient or the faint of heart. It needs to be approached with an excess of strategy, time and budget. If you have those things, and a good product and a willingness to be open to how the market actually perceives you (and not just how you think it should perceive you), you can find success here.

Lots of people think that if you do business in the States, then you’ve made it to the top, you’re the emperor of the world. What is the most common misconception of the US market in your opinion?

Well, there’s two. Especially for startups. One I’ve already touched on - and that is the very real lesson that the US market is not actually one, the single market.

But the second is that the US automatically equals success. You can do “big” numbers here in the US in terms of revenue, but your costs are also going to be insanely high, especially by Estonian standards. Yes, it’s good to be here, it’s nice to be successful here, and in terms of market share for most startups, this is still the place to be. But you need to be honest with yourself and understand if the success you are having here is just a vanity metric, or if it is really pushing you and your business forward. Sometimes not being here is the wisest move. And other times, you’d be crazy not to be.

The lesson is to remember to stop and take the time to figure out which is true for you.

What are the biggest mistakes that companies do when launching their operations in the US?

Not affording themselves enough runway, and not understanding the nuances of the market they are looking to enter.
Just like everything takes longer and is more expensive than you initially think in a startup, generally speaking - the same very much holds true here about the US market.
The only difference is that your burn rate will go up exponentially. If you are coming into this market, come in with a (realistic) plan, and a means to execute it. “A dollar and a dream” might be all you need to win the lottery here, but to make a successful run with your startup will require money, the right partners, and an ability to decide very quickly and on limited information whether you should stick to your assumptions, or adjust your course based on what you find here.

How to find the right partner for your business in the US? What are some of the “dos and don'ts”?

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.

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 EAS 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. Similarly, the Estonians living abroad community, overall, is an often-untapped natural resource and extended network of the country that I would encourage every Estonian entrepreneur to get plugged into. Foreign-born and expatriate Estonians are usually tremendously keen and happy to help Estonian entrepreneurs and individuals at home in any way they can.

As far as the do’s and don’ts around this market, 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. 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. It’s also important to come and experience the culture and the environment first-hand before making the jump into this market.

“if you want to go faster, go alone. If you want to go further, go together”
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 your opinion, why should every startup who wants to be successful expand into the US?

They shouldn’t! Success does not equal being the US market. Just look at Bolt!

Rather, every startup that wants to be successful when expanding into the US should make a real commitment to this market, spend time here, and seek out trusted partners who they can leverage to help them grow!

James York will give a hands-on seminar on marketing at sTARTUp Day 2020 on the 31st of January. The full seminar program will be announced in January 2020.
Articles you might also like:

Madis Lehtmets, New Program Manager: “Design is a problem-solving methodology”

Madis Lehtmets is the new Program Manager of sTARTUp Day! We talked with him about design, startups, stand-up comedy, how to write...
Read more

President Alar Karis at sTARTUp Day — “The Future of Innovation in Estonia”

We asked for sTARTUp Day 2024 visitor feedback, with one of the questions being about the most memorable speaker. The most popular...
Read more