Startup advice

James S. York: the US market specifics for startups, tips from an insider

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James is a very special person at SWG Mafia – not only has he been with us as a mentor since the first batch, but currently he is also a connection point between Estonia and the US working as Enterprise Estonia representative in New York. Lucky for us, he still visits Estonia often, always squeezing in some mentoring hours with our startups on marketing and US market specifics. We managed to catch him during Latitude59 in Tallinn and zoomed in on what founders from this side of the World should take into account, when thinking of going to the US market.


The US should not be seen as a unified market

It is very typical for founders from our region to look at the UK and the US as first markets for scaling, and it is understandable, as these markets are big and people speak English. However, James suggests that “US as a single language market” is one of the first myths founders should bust and forget – “There are nuances in doing business in each particular State. So it’s very good not just to look at the US, but what part of the US you really want to focus on. Also what the strengths of different regions are in relation to the startup and the service they’re providing”. While everyone is kind of hyped about Silicon Valley, he points out that there’s lots happening in East Coast and especially New York.

Can you be successful in the US without being in the US?

Whichever country you are going after, it’s very important to get the lay of the land – understand how things work, what are the cultural nuances, restrictions, regulations etc. If you have that, and especially if you are selling something for a low monthly fee, you can probably get away with having a back office in Estonia and just being regularly available to the US customers. However, once selling something more expensive or complicated as a product, American presence matters, and not only that. It’s a very common stereotype that Americans don’t look beyond their borders. I don’t know if that’s necessarily true but very often if Americans are not internationally minded they are more comfortable interacting with other Americans. So having one on your team is a huge asset.

What is the main difference between an Estonian and an American?

“In Estonia and in the region in general everyone is very direct and blunt. You say what you mean and you mean what you say. In the States people will give you a smile and something that sounds like a positive answer, while in reality they are trying to brush you off. Once you get comfortable with it and you can navigate within it then you can act accordingly”, that’s the first thing a foreigner needs to understand, once starting to operate in the US market. 

Last but not least, we just couldn’t resist sharing, what James thinks about a typical Wise Guys startup, as he has seen the development from the very early days: “the thing that I love about the wise guys teams is that you guys have a knack for finding the most passionate founders. They know what they are doing, they believe in what they are doing. And nothing is going to stop them! That has been true from the beginning. I think it’s kind of like: “That’s a Wise Guys team”.”


For more tips and insights on the US market and how to setup SaaS sales strategy, tune in to “5 wise minutes” with James. 

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