Marketing Entrepreneur James York Is Advising What’s Hot in Social Media Marketing in 2019

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 and he currently runs his own boutique marketing agency/consulting business, Oscar Diggs Digital that’s based in New York City.
James has also other ties to Estonia, for example, he is the secret voice of Estonia etc. Pay your attention to the article and you’ll find out what he means by that, besides fantastic insights about advertising on social media.

What’s your relationship with Estonia? Why do you like Estonia? Why is Estonia unique for you?

Estonia is my second home and at this point. I like to say I’m about as Estonian as you can get without actually being Estonian. I moved to Estonia in 2011 and cut my teeth working with some amazing high growth companies there, starting with Fits.Me where I spent a year as their Head of SME Sales. I began mentoring with Startup Wise Guys from batch 2; was almost e-resident #0 and taught my first Master’s course at Tartu Ülikool this past semester.
Clearly, I’m a big fan of the country... and as an American, it might be weird to say, but in many ways, Estonia offers entrepreneurs more of the “American Dream” and an opportunity to soar than the US currently does.
Not many people realize, but I’m also the “secret voice of Estonia,” having voiced all three of the country’s digital explainer videos about Digital Identity, E-Voting, and the X-Road system, as well as countless startup explainers, several English language audio tours for museums, and many tourism videos.

Today, a lot of my free time (what little there is of it) and energy goes towards helping to foster closer ties between the Estonian and New York markets as I have a foot in each world and tend to act as a bridge between the two.

The bureaucracy in Estonia is minimal. The government is sometimes more agile and responsive than the private sector, and the people here are just great – always bright-eyed and ready to try something crazy that might just turn into the next big thing.

Put enough people like that together in one ecosystem and magic happens.

Talking about 2019 – what are the trends that every marketing professional should look into in 2019?

Geofencing and AR are definitely two of the big ones.

You’ve probably heard about geofencing, which is where you can create a virtual geographic boundary that triggers an action on a user’s device when they enter or leave an area. One of my favorite (and most recent) examples of this is how Burger King trolled McDonald's by offering up burgers for $0.01 to any app user that got within about 180 meters of a McDonalds. Once in one of these geofenced zones, the user would be prompted with an insane offer and then rerouted to the closest Burger King location. It was pure genius and demonstrates just how powerful online technology has become in the offline world.

Most businesses and marketers tend to think that geofencing is something overly complex and difficult to implement, putting it out of reach for most advertisers due to a lack of budget and/or technical resources. But I believe 2019 will see this strategy becoming more accessible to more marketers, which will help create lots of new and innovative campaigns in the wild.

In fact, if you come to my workshop during sTARTUp Day I’ll be showing people exactly how to implement geofencing directly within their Facebook campaigns, completely on-platform and without the need for any 3rd party tools.

Augmented Reality, or AR, is also set to see a boon in 2019. With more and more modern handsets in the wild and improvements to both Apple and Google’s in-built AR capabilities within iOS and Android, the market is ripe for a wave of easier to use and easier to implement tools (note “easier,” not “easy”) that creatives and marketers alike can leverage to create some fun and engaging ways to interact with their audiences.

For example, Facebook’s Camera Effects Platform, which was recently rebranded to Spark AR, is one such tool that you can already begin playing and experimenting with right now. This sort of platform and suite of tools will allow Instagram and Messenger AR filters to become actively used and widespread marketing and branding tactics, just like Profile Frames have become in recent years.
Marketing is an exercise in strategy where you need to figure out how to say the right thing to the largest group possible.

Let’s say that I haven’t ever run any FB ads, but I’d like to start somewhere. Where should I start?

Definitely NOT with the blue “boost” button. That’s Facebook’s gateway drug into their advertising ecosystem and, while you might get lucky with it, you’re much better off spending a bit of time digging into YouTube tutorials on how to make use of Facebook’s Ads Manager platform.

Of course, the technical mastery is only one aspect of what you’ll need. Really, in any form of marketing, the first thing you should always do is ask yourself what your goals and objectives are?

A marketing campaign can be or do almost anything you want it to be. But each part or component of your campaign can and should really only ever do one thing at a time.

Are you looking to build awareness? Do you want to drive sales? Figuring out what it is that you want to accomplish, and why, and then working your way back is really the best advice I can give; and something we practice with every campaign we strategize and develop at my agency, Oscar Diggs Digital. 

What is the biggest mistake that you can make while running ads on Facebook?

Not testing.

Facebook is one of the most feature rich advertising platforms that exist on the planet today. And nearly every feature is available to anyone with the patience to learn how to use them, regardless of budget, team size or existing brand value.

That also means that when a campaign goes sideways, there are a million possible reasons why. And the best way to combat the potential confusion that this can bring is to make sure you structure your Facebook campaigns so that each Ad Set only ever tests for one or two variables.

For example, how do men and women react to your campaign? What about differences in age groups? Interests? Location?

And what about your messaging, creatives or graphics? And how do each of those perform when running against each slice and segment of your potential audience…?  You get the point.

The more structured and granular you can reasonably make your campaign setup, the easier of a time you’ll have diagnosing what’s gone wrong so you can fix it faster while burning less cash.

Could you name some of the biggest misconceptions when it comes to advertising on Social media?

That branding equals brand awareness, and that brand awareness equals revenue. This is a huge misconception for a lot of advertisers and marketers.

Very often organizations will want to invest heavily in branding or brand awareness campaigns with the explicit goal of that spend translating into revenue for the company. But marketing isn’t a game of “if you build it they will come.”

Marketing is an exercise in strategy where you need to figure out how to say the right thing to the largest group possible, where that group is composed of just the right people for your particular needs and where you’ve also managed to figure out how to reach those same people consistently, in the most cost-effective and sustainable manner possible.

That means understanding that your marketing campaigns can and should only ever try to accomplish one thing at a time, for example, brand awareness or lead generation - but not both at once (within the same campaign anyway). You can run different campaigns in parallel if you have the human and financial resources for it, but you should generally try and avoid attempting to kill two birds with one stone when it comes to advertising on social media (or anywhere for that matter).

Many companies have their doubts about marketing on social media. They say that don't see the ROI and it's hard to measure business-oriented success when doing branding by crafting social media posts. Do you agree with them or not? How could you measure the ROI of social media for your business-oriented results?

They’re right, but usually, because they’re doing it wrong. Not seeing ROI from your social media and broader digital advertising efforts is usually the result of a lack of thorough testing and trying to hit too many disparate KPIs from a single campaign.

To be successful when advertising and marketing on social media (and elsewhere) you need to first ask yourself, what is the business goal you’re trying to accomplish?

Then you can begin to craft a marketing strategy that can actually help you to reach that goal. Only then will your posts, ads, videos, banners, copy, blog posts and any other content “gel” and move beyond an ad hoc implementation of marketing tactics that may or may not be leading you in the direction you want to go.
Measuring success becomes easy once you know exactly what it is that you want to accomplish, and you have a strategic plan in hand for how you’re going to try and get there.

What’s the most important marketing KPI on social media?

The KPI you define that relates most to the business or marketing goal you’re almost immediately trying to achieve.

Where do you see social media heading within the next 5-10 years and how do you see it evolving? What are the next big things in social media? 

Not surprisingly, I’m an avid fan of Black Mirror. Looking at the trends coming out of China and how addicted we’ve all become to “Likes” and view counts, I think we’re looking at a future where the attention we’re able to generate for our social media avatars (whether virtual or just on camera) will have an ever-increasing influence in our offline lives - whatever little of them still happens offline, that is.

AR filters will become the new business casual, especially for remote teams; and VR chat rooms are going to further dissolve the diminishing 9 to 5 work culture and help facilitate team bonding and communication in an increasingly distributed world.

I think gamification is also going to become increasingly prevalent in all areas, from leaderboards on social media so you can more easily understand where you fit in the emerging popularity hierarchy; to employee engagement at work, where completing a task won’t be just about meeting your boss’s expectations and any organizational goals, but will also be designed in such a way that you get a kick of endorphins from the accomplishment.

I see productivity increasing, right along with burnout; and social media and the algorithms that fuel it are becoming ever stronger mediators of our relationships, both personally and professionally – continuing the trend we’re already seeing.

I wouldn’t go so far as to say we’re in for a dystopian future when it comes to social media, but I do think that in 5 to 10 years if you care at all about winning online and in life you’ll be sure to always be smiling when there’s a device nearby...

James will give a workshop during sTARTUp Day, where he’ll be showing people how to implement geofencing for marketing purposes and many other resourceful marketing hacks and tips, so make sure to grab your sTARTUp Day tickets now, if you already haven’t!

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