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How I targeted the Reddit CEO with Facebook ads to get an interview at Reddit

A bit over 2 years ago I was coming off a failed startup and out looking for new opportunities. I am not a fan of looking for jobs, my style is to target interesting companies and convince them to let me join them in their quest. So I decided to target Reddit because it looked like they were making some new moves. And, because, it’s Reddit!

I hatched the hare-brained scheme to write a blog article that might catch the attention of a particular person, get them to read it somehow, and then say “hey kid, I like the cut of your jib, do you want to come help us conquer the world?”. Sure, that person is actually younger than me, but you get the point.

I wanted to work at Reddit. Well, not just work at Reddit, but develop something very cool at Reddit that I think can make a huge impact on the business. So I wrote about it. I knew that the CEO of Reddit was a technical founder, so I put quite a deal of effort into that blog entry to try to impress him. Now, how to get him to see it?

My first thought was email. I can just email him! But that’s boring. What about getting my article to the top of Hacker News? I bet the CEO (and founder) of Reddit still frequents Hacker News. It is an amazing community, built off an early version of Reddit, and run by Y-Combinator (which incubated Reddit way back when). The problem is, I didn’t think my article would be interesting enough to a large crowd to make it to the top of HN.

Then I remembered a trick a friend of mine taught me a while back. That friend (who shall remain nameless, unless he wants me to name him) was running a startup and was using a very interesting technique to increase his chances of closing deals. Who wants to buy from a company they have never heard of? Not many people. His strategy was to target prospects (as directly as possible) with Facebook ads about his product so that when he called or met with them, they would already know the name. They probably didn’t know why they knew, but they had seen the name before, and that meant a great deal when meeting or speaking for the first time.

So I decided I would target the CEO of Reddit with Facebook ads.

But how? I didn’t have a big budget so I needed to be clever.

It turns out the Reddit CEO had a public Facebook profile, so I could go there to see details about him. Where he lived. What he was interested in. I took that info to the Facebook platform to help narrow down the campaign. But I didn’t want everyone to click on it, just one person. So I custom tailored the ad to directly target the one person I wanted to read it.

“Steve: Reddit needs recommendations”

The ad reached 197 people. 4 People clicked on it. One of them was the CEO of Reddit. I spent a total of $10.62.

Steve Huffman, CEO of Reddit, saw my ad, clicked on it, read (probably skimmed) my article, and liked it well enough to send a note to Reddit HR to contact me about a position.

Mission accomplished.

Chris Seline

P.S. I am out again looking for new opportunities. Drop me a line at my first name at if you like the cut of my jib!

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