Reddit Case Study: The Anatomy of a Massively Successful Post

Jeff Callahan knows the key to a successful Reddit post. In fact, his Reddit post became the second highest upvoted post ever on the socialskills subreddit—a large group with over 290,000 users.

Jeff Callahan Successful Reddit Post

Hey aspiring Reddit marketer, does this sound familiar?

You want to promote your content on Reddit, so you post a link on a dozen subreddit sites related to your business.

Half your posts immediately get deleted and get you banned forever from the subreddit.

The other half are severely down-voted. Now you have negative karma points and you’re worse off than you were when you started.

As Reddit veteran Jeff Callahan will tell you, if this is happening to you, you’re doing Reddit wrong.

He would know.

With more than 2,300 upvotes and almost 200 comments, his month-old post is currently the second highest upvoted post ever socialskills subreddit—a large group with over 290,000 users.

Jeff Callahan Successful Reddit Post

From this one post, Jeff estimates that he earns a dozen new subscribers (and potential new clients) a week to his site becomemorecompelling.com.

So, how did he do it?

As you’re about to read, it was no accident.

From top to bottom, Jeff’s post was carefully constructed to get exactly the response it did.

We talked to Jeff and asked him to break it down for us.

Note: Jeff uses his successful email newsletter to turn subscribers into new clients. If you want an easy way to capture more leads or emails from your current website, try Fieldboom.

The start: a non-clickbaity headline

Jeff’s headline has four pieces:

  1. Identifies Jeff as a member of the group
  2. Relates to the problems common to the community
  3. States what Jeff has to offer
  4. Demonstrates his experience

Here’s how it breaks down:  

Jeff Callahan Successful Reddit Post

Jeff explains why it’s so important to not give in to the temptation of click-baiting:

“We live in an age where there’s so much vying for information; it’s like the world wide web is really just a bunch of attention vampires. And so, it’s really important to not fool people into like, ‘Hey this one weird trick,’ but really respect them and saying, ‘Look, I struggle with what you’re struggling with. Here’s my path to getting to a better place.’ When you do that people automatically gravitate towards wanting to click on what you have to say.”

Why this works:

In that one headline, Jeff positions himself as someone worthy of attention.

It gets people to click, which is always the first step to a successful Reddit post. From there, it’s about drawing people in.

The intro: a set of questions that identifies the reader’s pain points

Successful socialskills Subreddit Post

Why this works:

Really want to pull people in? Start with their pain points.

“I knew what would resonate with folks,” Jeff explained. “And the only way you know that is if you understand the deep-seeded pains of your audience… And the best way to uncover those pains is actually to have conversations with people.”

Identifying pain points in the form of questions helps personalize a piece. By doing this, you inform the reader that you get them.

(By the way, we shamelessly stole this intro tactic for this article, in case you feel like you’ve seen it before. 🙂)

Note: Want to understand your audience’s pain points? The easiest way is just to ask! Create a survey and start collecting insights in a few minutes with Fieldboom.

Also in the Intro: a taste of his experience & a call to action

Successful socialskills Subreddit Post

Why this works:

Jeff has boiled down his experience into an alluring elevator pitch. Who is he? Why should you listen to him? Because he’s talked to over 90,000 people over 13 years! It’s these conversations that give him legitimacy to offer advice on social skills, as well as real-life examples.

Want to replicate this? Figure out what sets you apart and boil it down to its essence.

Following his experience, Jeff ingeniously places a CTA before the advice. It’s like a pep-rally before a big game.

But the trick is … that CTA has to be heartfelt. It can’t just be a gimmick.

The body: broken into meaningful, actionable sections

Part 1: Mindsets

Why this works:

Jeff creates a framework for readers to follow. Inside that framework are pieces of advice, tons of research, and personal experience.

The body of the post was adapted from a Quora post that had almost 140,000 views. He knew the material was good. He also knew he couldn’t just copy and paste his post into Reddit—because that would be disrespectful of the audience on Reddit.

He used the Quora post as a template, adding phrases and material he knew would resonate with the audience in r/socialskills.

No matter where you’re promoting, Jeff explains, you need to know what works in that particular space.

“There’s a saying “Content is king,” but my add on to that is “context is God.” If it doesn’t resonate, if it doesn’t click for people, guess what … they’re gone! And you’ve just sacrificed what could be a subscriber, potentially a client.”

How did he know what to include? He studied the group.

Jeff didn’t just join the socialskills subreddit and post the next day.

He’d been a member for three years before his viral post and had watched the group grow from under 100,000 to over 290,000 users.

He guesses that 90% of his engagement in the group is through comments rather than submitting his own posts.

This isn’t so much about being known, he explained. He’s sure there are people in the group who know him by his handle. But more importantly, he wanted to understand the group.

“The raw material has to come from the market. It has to! It can’t come from you sitting alone listening to a video of Gary Vaynerchuk,” Jeff said.

“Any advice that says you need to go internal to find the solution is missing the point when it comes to marketing,” he added. “The solution is not within you. It comes from the market, and the market will never lie to you. They’ll always be brutally honest with you and crush your dreams, and that’s fine, that’s good.”

Remember what we said about understanding pain points? We just came full circle.

At the end: another call to action

Recovering Awkward Person subreddit post

Why this works:

The link to his site is subtle, and the CTA isn’t a marketing call to action, but rather a “go do this” call to action.

This is the real secret to Jeff’s post: it reads like it came from a normal human being (i.e. not a marketer) who actually cares. Because it did.

Jeff admits he doesn’t really care about traffic or having the top post. “I’m there to learn first and get traffic second,” he told us.

Ironically, that’s exactly how to build a successful coaching business. You have to want to actually help people.

People messaged Jeff weeks later to tell him that they printed out his post, and they’ve never printed out a Reddit post before. “That says something,” he explained, “because ultimately I only care about people getting results.  You’ll even see in the comments when people say thank you,’ I say the only way to really thank me is to go out and get results.”

In the comments: engagement with every response

Jeff Callahan Successful Subreddit Post

Why it works:

Oh, you posted, and you thought you were done? Not on Reddit!

People don’t come to Reddit to read posts. They come to chat. To hang out. To engage in debate and discussion.

This is half of what makes a Reddit post trend (or not trend).

Notice how Jeff is always asking for additional comments and engagement. It’s not “thank you.” It’s “tell me more.”

Jeff Callahan Successful Reddit Post

These responses—especially the follow-up questions—create more and more comments. Which boosts the post higher and higher in the subreddit.

There’s residual impact of a successful Reddit post 

Because it’s the second highest upvoted post ever in r/socialskills, if someone clicks into the subreddit, they’ll be quick to find that post. Each day it gets a few hundred views.

Jeff has seen other benefits from both the post and his consistent engagement with the group.

You see how his website is listed next to his username? That’s a bonus he had to request from the moderators. He believes they granted him this “flare,” because they know and trust him.

Jeff Callahan Successful Reddit Post

Now, whenever he posts, he gains visibility for his site.

Just in case we missed anything, if you want to find success on Reddit, here are some suggestions.

Jeff’s What Not To Do’s on Reddit:

1) Do not—under any circumstances—post the same post to multiple subreddits with the same title.

2) Do not post a URL with a short text description like “Go here, read more!” Links should be context-dependent.

Jeff’s To Do’s on Reddit

1) Always respond to comments on your posts. The advanced level: Dig. Ask more questions and start a conversation.

2) Check a subreddit daily to gauge what’s working well. If you do that often enough, you’ll get a feel for what posts will do well.

Jeff’s Bottom Line:

“If you’re scared of marketing on Reddit, just know that if you’re a human being and you put the audience first and you last, you should do just fine,” Jeff told us.

“People are smart, Redditors are smart. Our senses when someone wants something from us or wants us to do something—they’re very sharp. We are now almost in the second decade of the 21st century,” he added. “At this point, our antennas go up when people want to market something to us. The more we can be helpful and the less we can blatantly market, the better.”

Note: Once you’ve led people to your website, use Fieldboom to capture their emails and keep in touch.

EJ left a career in UX/UI to write full-time. She believes in user-centered design and advocating for diversity in the tech field. Follow EJ on Twitter @whatiwritewith