Kieran O’Reilly

He was originally a member of Harvard University’s class of 2017, and his brother Rory O’Reilly of the class of 2016. He said that, from the time he was admitted, he had let his parents know that he would leave: “Since I got [into Harvard] I told my parents I would drop out.” The brothers said that their schoolwork did not engage them as much as their own projects did.⁠[1]

Boston Magazine writes that their GIF idea began while they were at Harvard University, where the original plan was an iOS app similar to Giphy, called “GIF Messaging,” in which students could browse animations by category and send them to friends; as the concept caught on, the brothers dropped out and moved to Silicon Valley. Rory O’Reilly said: “There was no risk in going out to CaliforniaCaliforniaCalifornia is a U.S. state on the Pacific coast; its capital is Sacramento and its largest city is Los Angeles. California was admitted to the Union on September 9, 1850, as the 31st state. Its population at the 2020 Census (April 1, 2020) was 39,538,223, the largest of any state.Open the full entry,” and pointed to the sheer number of venture capitalists there. The Harvard Crimson writes that they were then working on Glyphic, a GIF-messaging app, and realized after moving to the West Coast that the market for such apps was already saturated.⁠[2][1]

On when they left: the Thiel Foundation’s June 2015 announcement says the brothers dropped out of Harvard University “a year ago,” and Rory O’Reilly wrote on Product HuntProduct HuntProduct Hunt is a product-discovery and launch community founded by Ryan Hoover in 2013 and operated by Product Hunt, Inc. Makers present new products, while users vote, comment and review them and discover tools through categories, forums and AI search. AngelList announced its acquisition in 2016; as of November 2026, its official website lists Rajiv Ayyangar as CEO.Open the full entry that they had left school a little over a year before becoming fellows. The Next Web wrote in February 2015 that the team had received a small seed round and had taken time off school to work on GIFYouTube full-time.⁠[3][4][5]

Boston Magazine writes that the brothers launched GIFYouTube (GIFYT) in July 2014: any YouTube video could be turned into a GIF through their app or by typing “GIF” before “YouTube” in the video’s address. TechCrunchTechCrunchTechCrunch is an American technology news outlet founded in 2005 by Michael Arrington and Keith Teare and headquartered in San Francisco; it mainly covers technology companies, startups, and venture capital, and hosts events such as TechCrunch Disrupt. Its ownership passed successively through AOL, Verizon, and Yahoo, and in 2025 Regent announced its acquisition.Open the full entry, describing the tool on August 16, 2014, called it a side project by the team behind the GIF-messaging app Glyphic: the user adds “gif” after “www.” and before “youtube.com” in the address and then sets a start time and duration; the tool was unofficial. Tubefilter wrote on August 26, 2014 that users could also give the GIF a title, that the resulting GIF carried no watermark or logo, and that the service was not approved or supported by YouTube.⁠[2][6][7]

Boston Magazine writes that the brothers found that people liked sharing GIFs but found making them painstaking, so they shifted their focus to creation; after the launch the website crashed several times a day, which they put down to the buzz rather than to faulty engineering.⁠[2]

The Harvard Crimson wrote that the team first set up temporary work stations in hotel lobbies before settling in San Francisco and then in Berkeley, California; Paul A. Bottino, a lecturer at Harvard University, helped set them up in San Francisco. At the time of the interview the brothers were talking over Skype from Berkeley and still had “kind of a house” in San Francisco.⁠[1]

The article says that the team was working 17-hour days and often had to remind one another to leave the house; Rory O’Reilly recalled inviting Kieran O’Reilly to a friend’s party and hearing in reply: “Nope, I have to keep coding.” Speaking of the company, Kieran O’Reilly said: “I just felt like it was my child,” and “I couldn’t abandon it. I wanted to see it grow.” He also said: “I actually have nightmares that the website will break.”⁠[1]

He said that when they mentioned to people that they had dropped out, the reaction was: “oh, of course, Harvard-drop-out-start-up.” Rory O’Reilly said: “Our start-up is pretty much our life.” The article also says that Aaron Neuman, formerly of Harvard University’s class of 2017, had previously worked with the team; a correction dated February 20, 2015 notes that, while he previously worked on the project, he is no longer involved.⁠[1]

The Next Web wrote on February 10, 2015 that GIFYouTube had been founded by two brothers who were Harvard University undergraduates, and co-founder Rory O’Reilly described the company’s goal of letting people find the source video from a GIF. New features released then included a GIF type with sound that could be clicked to go to the source video (a plain GIF could still be downloaded) and a separate sharing page for each GIF created, where it could be voted up or down as on RedditRedditReddit is an online platform that organizes content and discussion around interest-based communities, founded by Steve Huffman and Alexis Ohanian in 2005. Users take part in communities by posting, commenting, and voting; its operating company, Reddit, Inc., listed on the New York Stock Exchange in 2024.Open the full entry. The article says that more than 1.2 million GIFs had been created in the first seven months and that three people ran the service.⁠[5]

On June 5, 2015, the Thiel Foundation announced its 2015 class of Thiel Fellows, 20 people chosen from a record 2,800 applications; he and Rory O’Reilly were listed in a single entry under “Animated GIFs.” The announcement gives him as 19 and Rory O’Reilly as 20, both from Elmont, New York; the two had dropped out of Harvard University a year earlier to make online communication easier and more fun, and their company, GIFTY (formerly Gifyoutube), helps people express themselves in pictures. The announcement says that Thiel Fellows receive $100,000 and mentorship from the foundation’s network of founders, investors and scientists, provided they skip or stop out of college during the two-year program.⁠[3]

Boston Magazine wrote the same day that the Thiel Foundation, started by PayPalPayPalPayPal Holdings, Inc. (Nasdaq: PYPL) is an American digital payments company that operates payment brands including PayPal, Venmo, Braintree, and Xoom, providing online and in-store payments, money transfers, and consumer credit to consumers and merchants worldwide.Open the full entry co-founder Peter ThielPeter ThielPeter Thiel is an American entrepreneur and investor, a co-founder of PayPal and Palantir Technologies, and the first outside investor in Facebook. He is a partner at the venture capital firm Founders Fund and founded the Thiel Fellowship, which funds young people to leave college and build new things; his public skepticism of higher education, his support for Trump in 2016, and his funding of litigation against Gawker Media have drawn controversy.Open the full entry, had named the brothers Thiel Fellows; Rory O’Reilly said they were already taking time off school and that he did not see himself returning to college. Rory O’Reilly wrote on Product Hunt that his brother was the company’s co-founder and chief technology officer and also a fellow.⁠[2][4]

Boston Magazine writes that Rough Draft Ventures, a student-run investment firm in the Boston area, had awarded GIFYT $25,000, and that more than two million GIFs had been created and viewed more than half a billion times. Revenue and fundraising, the article says, were not their top priorities; Rory O’Reilly said the team would eventually need to make money to support itself, that they were focused on evolving the brand, with the specifics under wraps, and that “a lot of GIF stuff is coming soon.” Kieran O’Reilly said they aimed to serve people who “want to build a GIF but might not know how.” The Thiel Foundation’s announcement gives the company’s name as GIFTY; Boston Magazine writes GIFYT.⁠[2][3]

Jamie Zoch of TheDomains wrote on August 22, 2015 that GifYT had launched a new site at gifs.com, announced in a Medium post by co-founder Rory O’Reilly; the article judged that the company “appears” to have bought the domain recently from Advertical Media LLC of Palm Coast, FloridaFloridaFlorida is a U.S. state occupying mainly the Florida peninsula, with its capital at Tallahassee; its most populous city is Jacksonville. It entered the Union on March 3, 1845, as the 27th state, and had a population of 21,538,187 in the 2020 census (April 1, 2020).Open the full entry, and noted from registration records that the domain moved to privacy protection at eNom on July 10, 2015 and changed name servers on August 4. The article says that the company appears to have renamed itself GifYT and also owns the matching GifYT.com domain, and that a whois search shows the GifYouTube.com domain to be owned by co-founder Rory O’Reilly.⁠[8]

In his launch post on Product Hunt, Rory O’Reilly wrote “Welcome to GIFs.com and The GIFs Player!” and announced funding from Biz StoneBiz StoneBiz Stone is an American entrepreneur and author best known as one of the co-founders of Twitter; he went on to co-found the online publishing platform Medium, the question-and-answer app Jelly and the social app company West Co, has been an angel investor in a number of startups, and sits on the board of Mastodon’s U.S. nonprofit.Open the full entry, Binary, Foundation CapitalFoundation CapitalFoundation Capital is an American early-stage venture capital firm founded in 1995, with offices in Palo Alto and San Francisco. It invests in enterprise software, artificial intelligence, fintech and crypto, and was an early backer of companies including Netflix, Solana and Cerebras.Open the full entry and 1517.⁠[9][8]

Jay Donovan of TechCrunch wrote on May 5, 2016 that the team behind gifyoutube.com, which had been part of gifs.com for a while, had launched a new tool that converts many video formats into GIFs and adds blur, stickers, hue changes and other effects; the article says the tool was built by “a couple of Harvard dropouts (the O’Reilly brothers who built the tool).”⁠[10]

Thiel FellowshipThiel FellowshipThe Thiel Fellowship is a two-year grant program started by investor Peter Thiel and run by the Thiel Foundation that funds young people who skip or stop out of college to build new things instead. The program has been criticized by figures in education for encouraging young people to leave college.Open the full entry: Official website: https://thielfellowship.org/ (opens in a new window).⁠[11]