Inbound In Love Game Show: Episode 2, One-Upper Oliver

In episode 2 of Inbound in Love, we check out the Valentine’s Day online behavior of a persona of young singles. Learn more about one of the fastest growing segments here.

It’s Valentine’s Day people, and I’m here to show y’all some more persona love with another installment of Inbound In Love.

In our last episode, Small Town Taylor gave us some insights into her online behavior, who and what she is shopping for. And we gave y’all tactics on how to best engage her.

I’m giving this insight away for free so I hope y’all are using it. So for those of you just now tuning in, I’m the Manager of Market Research & Analytics (and Awesomeness) at iAcquire. I have returned with some brand spanking new persona data. I’m just trying to help  the marketing world make those “love connections” (see what I did there) during Valentine’s Day.

Alright let get cray!

Contestant #2: One-Upper Oliver

Let’s welcome One-Upper Oliver to the stage.

The One-Upper Oliver persona represents a one of the fastest growing segments in America, which is predominantly made up of young singles.

This persona type typically lives in apartments in port cities, but they especially congregate in  metro cities like San Francisco, Seattle and New York City.

They rarely have deep roots, usually moving on after three years. About twenty years ago this segment would have been viewed as “rolling stones” however now we just call them hipsters.

Okay, okay so this dude does look like a hipster. I totally didn’t plan that. Oh man, I so planned that!

The adults that fall into this persona type spend a lot of time online chatting with friends via instant messaging, social networks or connecting with them by sharing music files.

They tend to head to media websites daily, to get the latest cultural news or sports scores. While many are somewhat reluctant to buy products online, they do a lot of research on the products they are interested in.

They also like to visit websites that have a heavy focus on food, style and current events. These are the elusive shoppers who use the Internet to help plan their shopping trip but while in that process they can be easily sidetracked to buy something on the spur of the moment.

Overall, the One-Upper Oliver persona type is a discriminating consumer. Okay one last sidebar, can’t you totally see him doing this on a date…


When compared to the other segments within the Valentine’s Day audience, these jaded internet surfers are not very receptive to online advertising.

So you’re probably wondering which retailers have stepped up for a little Inbound In Love. Let’s meet them:

Marc Jacobs – You cannot find a lady who does not like a MJ in their life

Gap – Khakis for everyone!

Bass Pro Shop – Wow, that’s a rather large… fish you have!

So, let’s pick Oliver’s noodle to see what he is looking for in a brand on this day of love!

Who are you shopping for? 

I don’t know, dude. Valentine’s Day is such an outdated concept. I mean, I don’t even know if I agree with the premise of Valentine’s Day. It’s like a holiday made up by corporate America to give people another reason to spend money on products we don’t need.

Do you know how many roses killed around this time of year? Like billions! Billions! Just so we can we give them to someone who may dump you after they find out you wore their skinny jeans to work.

Do you have an idea of what you’re shopping for this  Valentine’s Day?

I mean, I was planning on getting a Marc Jacobs bag for my kinda-girlfriend or whatever, cause she’s like really into that expensive designer stuff. Which I don’t understand, it’s just a bag. Its not eco-friendly.

But I don’t know, I’m trying to snag this Sega Genesis on eBay so let’s see if I have any money left over.

Dude did you just say Sega Genesis!? You know that iTunes has most of those games available to be downloaded right now? Anyway… What are you looking for in a retailer?

I’m looking for a retailer that, like, doesn’t even get me, you know. I get so sick of it when I go into a store and I feel like they already know me. You know? It’s like, get out of my brain marketing guys. Maybe I don’t want what I want.

We seem to meet a lot of contestants with that problem. Is there any way a retailer can sway you to shop with them?

All I really want from a retailer is like, nothing. I care a lot about graphic design, but I hate seeing design all over the place. I am more likely to buy from a retailer if they don’t use any graphic design at all. Plus, I hate advertisements so I really only buy from retailers that don’t have any advertising at all.

Plus, I’m like a sugar-free vegan right now, and I get a lot of headaches, so I can’t buy any loud colors. It’s just like, sets me off or whatever. I always used to envy people that got migraines but I don’t know, maybe it’s not that cool.

I’m just over it, you know. Who has the time? My internship is really ramping up my workload, so I’m just like super stressed.

One-Upper Oliver seems to be a downer! How do marketers target someone that is so jaded and negative towards advertising?

The best way to engage with this persona is with visual content. This persona’s online search is focused, so their attention has to be captured quickly. Infographics and short videos would the best way to tackle this persona.

Also keep in mind that a large majority of people that fall into this persona type are conducting their searches on a mobile device, so ensuring that your visual content is optimized for mobile devices is key.

So, which brand did One-Upper Oliver go with?

Marc Jacobs

His “female friend” kinda left him no choice.

Marc Jacobs’ simple and easy to navigate website is exactly what Oliver is looking for. And while they are currently running a Valentine’s Day campaign, it is a very minimal part of their overall website.

With this persona becoming one the fastest growing segments in America, brands should rethink how they market to this particular segment using these insights.

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