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5 Important Lessons from Content Marketing Royalty

If I asked you to pick out some top examples of businesses using content marketing to supercharge their growth, there probably would be some very familiar responses – the “Usual Suspects” of content marketing, if you will.

One example that many people would leave out, when first contemplating this question, is a brand that I hold quite a lofty opinion of… In fact, I’d call it one of the greatest examples of content marketing in the history of the web.

What business could possibly serve as such an example and yet be so criminally underappreciated?

None other than OkCupid, which was the free online dating service acquired in 2011 by IAC (owners of for over $50 million.

How did they do it? More importantly, what lessons can your business take away and implement in your own content strategy?

Today, you’re going to find out the answers to both of those questions!

The Rise of OkCupid

OkCupid Logo

While reading some of the posts on the OkCupid blog (now discontinued since the acquisition), you can’t help but compare it to places like TheOatmeal: you know the writers are very in control of what they are doing, but the output is so genuine it almost looks like the success happened by accident.

That’s far from the truth, though, and as OkCupid co-founder Sam Yagan has revealed in a multitude of interviews, the team always viewed content as a significant part of their marketing strategy, even going so far as to say they didn’t care about social media:

“We don’t really look at [social media] like that… We do it from the bottom up. We want to create content that people are going to fall in love with. And the Twitter followers and the Facebook likes, that will all take care of itself.”

So, outside of building the best damn free dating software they could, the team relied heavily on “OkTrends,” which was the name of the OkCupid blog. Yagan even refers to the success of the blog as the “tipping point” for the company, when things really began to take off in 2009.

Checking out the blog itself, you regularly see posts hitting numbers like this:

content example

Surely, we can draw some important lessons from how the OkCupid team turned their blog into such a powerhouse on the web.

Below are the 5 biggest insights that any brand can take away from the OkCupid content efforts:

1. A Unique “Spin” on Content

Yagan has mentioned that the OkCupid team had the advantage of being in a really popular niche – online dating. Since dating and relationships are a general interest for everyone, the content angle had a wide appeal from the beginning.

That being said, smart marketers already know that they need their own “spin” (or unique selling proposition) to make their content stand out in the crowded place that is the web. Also note that OkCupid really took off in 2009, so they didn’t exactly have a first mover advantage.

Well, then, how did they do it?

Staying far away from generic topics like “dating tips,” the team did something that was unheard of in the dating space at the time: they wrote articles on dating that were based on mathematics!

That’s right, head over to the OkCupid blog and you’ll see posts like:

The Mathematics Of Beauty

Your Looks and Your Inbox (How They Correlate)

The 4 Big Myths of Profile Pictures

Within posts, you’ll see complex data sets from OkCupid users broken down into all sorts of charts and graphs.

When you’re reading an article about online dating, would you ever think you’d see images like this:

dating math

Or even this (!):

messages received last month vs. attractiveness

The result was content that seemed to have come out of left field. But it was interesting, really interesting.

The OkTrends blog avoided generic content and became “citable” instead, the absolute key for getting mentions and links in the online world.

Yet things didn’t stop there…

2. Sex, Drugs, and Rock ‘N’ Roll

Sub-headlines like that typically make you do a double take when they appear in articles about marketing, but there’s a point to be made here.

Eye-catching titles are powerful; but while that’s nothing new, the OkCupid team really knew how to write headlines that were an absolute tease.

With examples like:

10 Charts About Sex

The Big Lies People Tell In Online Dating

Gay Sex vs. Straight Sex

…you can see why the articles were able to take off on social media and hit “viral” status once they picked up enough steam.

Some defining characteristics seem to be that each headline “provokes” a debate, gives only a little bit away (very tantalizing), and always addresses a heated topic in the online dating space (attractiveness, age, sexuality, honesty, etc.).

Dating already lends itself to being a popular topic, but OkTrends posts always hit on the topics that could keep us up at night. And the headlines are written in such a way that we simply cannot resist checking out what the fuss is all about.

It’s almost like the team was dating their prospective customers, because the headlines aren’t written to be superficially outrageous. They come off as short, sweet, and directly aimed at something within us that strikes a nerve.

3. A Writing Style Finely Tuned for Their Audience

Going beyond calling the OkCupid content “great” and moving on, it’s important to take a look at WHY their articles resonated so well with their target audience.

First up, you’ll notice that humor is a big part of their writing style and is even incorporated in their visuals:


This isn’t by accident: the team has noted that since the dating arena is about as “fun and casual” a topic as you can get (outside of maybe an outright comedy site), they inserted plenty of humor to offset the myriad charts and data points included in their blog posts.

Does that mean your next article should include some of your stand-up material? No, because you’re using it at random: you have to craft a writing style that will resonate with what you are selling and (more importantly) to whom you are selling.

Next up, we also see that each article is broken up quite well; again, another strategy to offset the potentially intimidating prospect of looking at a bunch of data.

Look at this intro from the OkCupid post on the “Biggest Lies in Online Dating”:

todays set

The “data points” are given some actual faces via real OkCupid users, the first myth (and the reality) are emphasized with different fonts and colors, and the body content is easily browsed since it is broken up generously.

If I could use one word to identify what’s being done well here, I would describe the content as being really “approachable” in that it doesn’t appear intimidating to start reading and dive in. (Probably a very appropriate term since it’s about online dating!)

Compare their stylized blog posts to that of a typical source of data sets in academic research:


The OkTrends content was specifically built for the web, and it was done beautifully.

You’ll even find multimedia sections in certain posts, including:

Interactive charts that adjust based on an entered age

Click-and-drag graphs that respond to user input

Tables that adjust data based on ethnicity

All of these sorts of creative details made their blog posts an experience rather than just another article.

While the team never dabbled in things like videos or infographics, they certainly made up for it by creating amazing content that could not be done anywhere else but the web, playing to their medium (and their audience’s expectations) perfectly.

4. A Content Style Hand-Tailored to Convert

Beyond the writing style and it’s unique “twist,” the OkCupid content shines as a heroic example of content marketing because it pinpointed the most important aspect of all – the content was specially crafted for those most likely to use the OkCupid service.

The OkCupid team (being made up of former math majors) was notorious for doing rigorous testing on who exactly was using their service:

“According to our internal metrics, at least, OkCupid’s users are better-educated, younger, and far more progressive [than the average online dating user]…”

The team certainly embraced this “youthful, geeky, and largely liberal” user base by creating content that they KNEW would perform best with them (with the added benefit of it being part of a large enough topic to appeal to many people).

While it’s hard for any of us to take a pass on checking out posts entitled “Don’t Be Ugly by Accident!”, the information contained within that post (and all of the others) was specifically meant to pique the interest of the typical college-age, nerdy, liberal person that was most likely to sign up for OkCupid.

(As a matter of fact, in the above post, the team breaks down which cameras take the most attractive pictures. How geeky is that!)

So, in addition to choosing a unique angle for their content, crafting it perfectly for the web, and writing headlines made to capture attention, the team also took the time to make sure each piece spoke to those most likely to sign up.

This is something many content marketers miss: they try to fill up seats before figuring out which audience should be sitting there.

5. Hopping on Popular Trends

Given that their blog name is OkTrends, it’s only fitting that the OkCupid team was also fantastic at hopping on hot topics in order to generate more interest for their posts.

While they have numerous examples of this strategy, by far the article that paid off the most was their piece on The REAL “Stuff White People Like.”

Playing off of the formerly (insanely) popular Stuff White People Like blog, the team analyzed trends on what white people (and all other races) are looking for in their dating partners, based on the things they listed in their profiles.

The article mixed in all sorts of buzz (race, intrigue, dating), but the real driver of the piece was that it was a takeoff on the success of a site that was getting a TON of press at the time.

Even though they used this trend to “piggyback” their post, the content quality and styling did not change, which is a great lesson for those content creators out there who want to see an example of using something popular without dropping the heart of their message.

…Did They Do Anything Wrong?

Despite the fact that I consider the OkCupid blog an inspiration of mine (and the Mr. Miyagi to my karate kid), there are a few things they did that marketers could certainly improve upon.

One of the first things you might notice is that the blog isn’t all that great at collecting email addresses.

In addition to the fact that email is particularly amazing in the B2B space, email marketing as a whole is an insanely useful tactic. The OkCupid blog could have been a big source of incoming email addresses if that had been made a priority.

While the blog is very “hassle free,” and I commend the team for keeping things simple, I feel like a bit more could have been done to shift people over to the OkCupid site to actually sign up.

In the text description up top, for instance, no mention is made that OkCupid is actually a dating site! While there is a small banner and link up in the corner, it’s not made completely obvious what the OkCupid software can do for you and your dating life.

Despite these subtle tweaks, though, there aren’t many negative things I can say about the OkTrends blog. It just does too much right to nitpick about the details.

About the Author: Gregory Ciotti is the marketing guy at Help Scout, the invisible help desk software for small business owners who love their customers. Download our free e-book on “Converting More Customers (with Psychology)” for more research on your customers.

  1. Great analysis! I am particularly a big fan of their “Facebook and Twitter followers will take care of themselves”. It’s so simple yet so many businesses try to hoard these artificially before they develop a unique spin and really resonate with their audience.

    • Agreed, they spent so much time on their content and so *little* time on social media that it would shock most so these social media marketers, yet the growth of the OKTrends blog speaks for itself. :)

  2. Wow! They really do know what to do to achieve their goals. That line too struck me the most. A lot of entrepreneurs spend so much effort with social media. But with them, it’s like focus on the content and let those social buttons do the magic for you in exposing your posts to a larger audience. Thanks for sharing, Gregory! :)

  3. I tell u guys….this blog deserves to be visited everyday…very good information here

  4. Hey,

    Great article you posted,if you want a larger audience on your post you should use social media buttons and type unique article like this.

  5. hey Gregory Ciotti !
    Great post. I totally agree with your this point that ” choosing a unique angle for their content, crafting it perfectly for the web, and writing headlines made to capture attention, the team also took the time to make sure each piece spoke to those most likely to sign up”. i have learned a lot from this post.

  6. Was very interesting to read. I agree with all of it! Being unique and contrating on creating outstandong content that resonates is the key.

  7. Fantastic analysis and so many takeaways I can’t absorb them all but what sticks out is CONTENT, all caps necessary. Facebook, Twitter, all good tools but it’s much more important to focus your sights on what your saying to your audience over where you’re saying it.


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