In 2009, Alan Schaaf, an avid Redditor, grew frustrated at the amount of time he spent staring at broken, or dead, images, or waiting for animated gifs to display. He realized there wasn't a central image-hosting site Redditors--or, really, anyone on the Internet--could use and count on to continue hosting their image reliably.

From his bedroom while attending Ohio University, Schaaf created Imgur (pronounced "Image-er"), and posted a link to his nascent image-hosting site on Reddit, writing: "I created an image hosting service that doesn't suck. What do you think?"

Five years later, Imgur is one of the most highly-trafficked sites in the world. (Its Alexa rank in America is 22, and it has millions of users each day.) And Imgur the company is growing up. With a fresh infusion of $40 million in venture capital funding, it now employs more than 20 people (up from 11 a few months ago), and is still hiring. I sat down with Schaaf and asked him to lay out his strategy for asking insightful questions when interviewing candidates.

Culturally, what do you look for when hiring?
It's not always about "can you do the job?" It's about "can you fit in with the team?" Are we going to come in every day and be really excited to work with you? Are you going to be that glue that holds a team together? Or are you going to be the poison that separates the team?

How can you actually determine that?
By reading into what people say. We turn down a lot of really smart people who just say something weird in the interview. They might refuse to answer a question or seem unwilling to participate in the conversation. We watch out for the people who can only talk about themselves, and not be interested in a problem they are presented with.

What's your favorite interview question?
Oh, I have a good one. My favorite interview question is: If you could have a superpower, what would it be? I can get really into it. Because everybody says "flying," right? So: how fast are you going to fly? Are you going to fly so fast that all your clothes fly off? Are you going to fly so high that you can't breathe anymore? What are the practical limits? Can you carry someone? We try to take whatever they say and almost turn it against them so they can figure out the problem associated with that. At the same time, it's also really personal.

What's your answer?
My answer is: "I want to be able to teleport." The reason I want to be able to teleport is that I don't like waiting around. It's one of my pet peeves. I also don't like traveling; because I don't like sitting on a plane for six hours, doing nothing, essentially wasting time. You know what would be awesome? Bam, I'm in New York. Or, I'm in the mood for some dim sum. Bam, I'm in China. I don't have to wait around, and it feels like I could live twice as long by not, like, waiting in lines and traveling.

What's the weirdest answer you've ever gotten?
One of the best answers happened just last week. This guy had a normal answer, like being invisible, and his follow up was, "you know what else would be good? Having a really ordinary superpower. Like the ability to never say 'you too,' to someone when you don't mean it." Like, when the waiter says, "enjoy your meal," and you say "you too." You'd save yourself from an awkward situation, many, many times. I thought that showed something about his character. And it was funny.

Published on: Jul 3, 2014