Harvard to Homeless — all because of animated GIFs

Rory O'Reilly
4 min readAug 20, 2014

“Hey — it’s Rory. Room 208. Is there anyway we could have a late checkout time — please?”

It was almost as if in this moment, our entire world was confined to our quaint hotel room. A small bed. A chair. A desk. A usable bathroom.

We would live anywhere, as long as it meant we could continue to work on GifYoutube.

Our lives revolve around GifYoutube. Yes, the animated GIFs that everyone love — they were the root that brought us here. 3 guys dropping out of Harvard, moving to San Francisco, not having housing — all for the sake of making animated GIFs.

“Yes, Mr. O’Reilly. You can have an hour extension.”

Kieran, my brother and co-founder, frantically yet purposefully typed away at his computer, simultaneously talking with Rackspace about moving our servers over. Aaron chirped gleefully, shocked at what we had woken up to. I blast out emails to investors, friends, and anyone who may be interested in what’s going on.

It had been almost like any other day in San Francisco for us; waking up in a different hotel room; skipping breakfast and lunch (ouch); checking the stats for the site. Until we realized, shit, what the heck, the site — wait — why aren’t our GIFs making? Why is the site down? A quick look at the stats one more time — ef. Where’s all this traffic coming from. After a search around google analytics — we let out a wail. Someone posted about uson imgur. We were viral.

I almost felt like I could melt. For the previous week, and consequent 3 weeks afterwards (and counting) we would move a total of 13 times. It felt as if everyday we’d wake up and move to a friends place, a hotel or an Airbnb - a new distant location. Fun, in a way; but incredibly stressful. Always refreshing pages and looking for the best deals, scouring the internet for the few places still available last minute, and eating take out every.single.meal — it had gotten kind of tough.

During this joyous moment, everything felt like it had fallen into place.

I was snapped out of my reflecting trance: “Guys. in 5 minutes we need to get out of the hotel,” Aaron reminded us. I called the front desk again and pleaded.

“We have a few more hours,” I shouted.

I got back to my emails. Friends, investors, and peers all reaching back, offering to help with the servers, and showering us with advice.

Hours tick by as Kieran, Aaron and our friend Ruiqi worked diligently. “Okay, time’s up. Everybody, grab your luggage!” Kieran and Ruiqi talking with Rackspace, me briefing the Uber driver as to why we have all these bags, and 3 guys in the back seat pounding on their laptops ensued on the 40minute ride to an AirBnb in Oakland.

Flash forward three weeks and half a dozen more moves, and that brings us to this week; the week we were ready for a serendipitous moment; the week we were ready for traffic — the week we didn’t crash (yet).

I was reading a post on twitter about someone doing 12 startups in 12 months; he had posted on HackerNews and things went crazy awesome for him. I was already into this journal entry, when a light-bulb went off: why not show HackerNews? I was scared, but I posted anyway. What happened next is only indescribable.

Within 24 hours we were #1 on HN, #1 on Product Hunt, #1 on /r/technology, and even had our very own techcrunch article.

Over the next few days, we’d be featured on other media sites: yahoo, cnet, business insider, buzzfeed and a bunch more. Google+ even promoted us:

The traffic is still maintaing — it’s absurd. All this attention has been for only the first stage of our project.

Although sometimes it’s tough moving around, and living the crazy lifestyle, this is a project we all believe in strongly. There exists no easier or faster GIF creation service. Webm is still broken. GIF discovery is broken. These are all problems that we seek to fix — a great interface for easy gif/webm creation, discovery, and beyond. It all starts with making it dead easy.

After having time to reflect and write, I can look back and say what we’re doing is crazy, but it’s worth it. Dropping out of school. Moving all the time. Sleeping little. Eating less. All for the love of GIFs? Yeah, it’s worth it.

In the coming weeks we will unveil something that we believe will change the way the internet uses animated GIFs in general.

I only have two goals now: revolutionizing the way we interact with animated GIFs…and finding a place to live for tomorrow.

Thanks to Kieran and Aaron for being amazing, of course; Ruiqi, for helping out; Conrad, who inspired this article by his own Pitch Your Life article [A+]; Eric for being a great friend and assisting with everything; Ryan, Andreas and Erik for their support, and inspiration; Victor and Kyle for holding our stuff during some tough moving periods; Amy, Mom and Dad for their love and support; and to the many founders we talked to who I did not ask permission to mention

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Rory O'Reilly

Dropout @Harvard | Founder @Expand | Founder @ gifs.com | Thiel Fellow | 30 < 30