Rory O’Reilly

He was originally a member of Harvard University’s class of 2016, and his brother Kieran O’Reilly of the class of 2017. He said: “At school our [academic] work isn’t our life, it’s something we do for classes.” The Harvard Crimson writes that the brothers started an application to the iLab’s Venture Incubation Program but never followed through.⁠[1]

Boston Magazine writes that their GIF idea began while they were at Harvard University, starting as an iOS app similar to Giphy, called “GIF Messaging,” in which students could sift animations by category and send them to a friend; after the app caught on, the brothers dropped out and moved to Silicon Valley. The Harvard Crimson writes that they were then working on Glyphic, a GIF-messaging app, and found after moving to the West Coast that the market for such apps was already crowded.⁠[2][1]

On when they left: the Thiel Foundation’s June 2015 announcement says that he and his brother Kieran O’Reilly dropped out of Harvard University “a year ago,” and he himself 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 the brothers had left school a little over a year before becoming fellows. The Next Web wrote in February 2015 that the team took time off school to work on GIFYouTube full-time after a small seed round.⁠[3][4][5]

Boston Magazine writes that the brothers launched GIFYT (GIFYouTube) 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 inserts “gif” between “www.” and “youtube.com” in the address and then sets a start time and duration, without frame-by-frame control; the article says it was not an official YouTube tool and might stop working if YouTube’s legal team objected to the use of its trademark in the domain name. 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 realized that while people enjoyed sharing GIFs, making them was a painstaking process, so they shifted their focus to creation; after they launched the website it crashed several times a day, not because of faulty engineering but because of sheer buzz, which made them confident they were on to something.⁠[2]

The Harvard Crimson wrote that the team first worked from temporary work stations in hotel lobbies before settling in San Francisco and then in Berkeley; Paul A. Bottino, a lecturer at Harvard University’s engineering and applied sciences school who teaches “Startup R&D,” helped set them up in San Francisco. At the time of the interview the brothers were talking over Skype from Berkeley, 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 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 each other to leave the house. He recalled: “Yesterday I went to a friend’s party, and I asked Kieran to come, and he was like, ‘Nope, I have to keep coding.’” He also said: “Our start-up is pretty much our life.” Kieran O’Reilly said that when they mentioned to people that they had dropped out, the reaction was: “oh, of course, Harvard-drop-out-start-up.”⁠[1]

The article says that their new project, GIFYouTube, let users upload videos and convert them into GIFs; Aaron Neuman, formerly of Harvard University’s class of 2017, had previously worked with the team, and a correction dated February 20, 2015 notes that he was 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 explained that the team wanted to help people discover videos from GIFs so that they could always find the source. New features released then included an embeddable GIF type with sound that linked back to the source video (plain GIFs remained available) and a separate sharing page for each GIF created, where others could vote it 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 a team of three 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 Kieran O’Reilly were listed in a single entry under “Animated GIFs.” The announcement gives him as 20 and Kieran O’Reilly as 19, both from Elmont, New York; the brothers had dropped out of Harvard University 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 years of the program.⁠[3]

Boston Magazine wrote the same day that the brothers had been named Thiel Fellows, and he said he did not expect to go back to school: “I don’t see myself returning.” The article says that Rough Draft Ventures, a student-run investment firm in the Boston area, had given GIFYT $25,000, and that more than two million GIFs had been created and viewed more than half a billion times. Kieran O’Reilly said the product was for 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]

Answering a question on Product Hunt about the 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, he wrote that “Being a Thiel Fellow is great,” and said that one of the best things about the fellowship was its community, with a sense of camaraderie; since the brothers were already out of school when they were selected, the program did not push them to leave, and they could compare working on gifs.com before and after becoming fellows.⁠[4]

Jamie Zoch of TheDomains wrote on August 22, 2015 that GifYT had launched a new site at gifs.com on August 18, 2015, announced in a Medium post by co-founder Rory O’Reilly: “today, we’re announcing the official launch of GIFS.com and the GIFs Player.” The post says: “Every day, GIFs are being created and used to deliver engaging content — from news, to sports, to art, to humor,” and credits the company’s backing: “With 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.”⁠[8]

The article says that the gifs.com domain had previously belonged to 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, which had also run a website on it; registration records show that the domain moved to privacy protection at eNom on July 10, 2015 and changed name servers on August 4. The article judges that the company appears to have bought the domain recently, but the sale was unconfirmed and neither party responded to requests for comment. It also says that the company had earlier renamed itself GifYT and still owned its main domain, GifYT.com, and that registration records show GifYouTube.com as owned by Rory O’Reilly; the company’s Angel.co listing gave it as founded in 2013 under the name GifYouTube.com, with $75,000 in seed funding at a $375,000 valuation; the domain appraisal site Estibot valued gifs.com at $162,000.⁠[8]

His launch post for gifs.com on Product Hunt opens with “Hey internet! Welcome to GIFs.com and The GIFs Player!”, presents The GIFs Player as a way for GIFs to link back to their source videos and related content, and names funding from Biz Stone, Binary, Foundation Capital and 1517. In replies to comments he wrote that the team was working on a set of filters such as slow motion, and that “We think one day every gif will be in the player.”⁠[9]

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)” and judges the new version “definitely easy to use.”⁠[10]

On the Product Hunt page for gifs, the in-browser GIF editing tool (“Create personalized GIFs in your browser”; the page shows no exact date), he answered users’ questions: mobile was “definitely on our mind,” slow motion was a feature the team wanted and expected within the next month, and a shortcut for choosing a clip’s start and end points was coming soon; the team was “focusing really hard on video augmenting,” channels might come later, and more search options beyond YouTube were being considered.⁠[4]

TechCrunch wrote on February 2, 2021 that MyCard, Inc., the legal entity named in the terms of the fintech startup Millions’ website, appeared on a filing with the U.S. Securities and Exchange CommissionU.S. Securities and Exchange CommissionThe U.S. Securities and Exchange Commission is the federal securities regulator of the United States. Created during the Great Depression by the Securities Exchange Act of 1934 and led by five commissioners, it has a three-part mission of protecting investors, maintaining fair, orderly and efficient markets, and facilitating capital formation.Open the full entry for a $3 million raise in December 2020, which listed two names, Kieran O’Reilly and Rory O’Reilly, the same names as the brothers behind gifs.com. Fortune wrote on February 3, 2021 that MyCard was a New York–based startup listing Rory and Kieran O’Reilly as its executive officers, and that the pair were behind the launch of gifs.com, which was then used by more than one million people.⁠[11][12]

The seed investors listed by TechCrunch include Giant Ventures, 8VC and Supernode; Twitter co-founder Biz Stone; Italic CEO Jeremy CaiJeremy CaiJeremy Cai is an entrepreneur, a co-founder of the hourly-worker hiring software company Fountain (formerly OnboardIQ) and the founder of the online retailer Italic; he was a member of the 2015 class of Thiel Fellows.Open the full entry; Allbirds co-founder and CEO Joey Zwillinger; Casper SleepCasper SleepCasper Sleep is an American mattress and sleep-products company founded in 2014 by five co-founders including Philip Krim and based in New York. It began by selling a single mattress online, shipped folded in a box, and later added pillows, bedding and furniture, its own stores and retail partners such as Target. It listed on the New York Stock Exchange in February 2020, was taken private by Durational Capital Management in January 2022 and was acquired by the foam maker Carpenter Co. in October 2024, becoming its subsidiary.Open the full entry co-founders Neil Parikh and Luke Sherwin; Daniel Greenberg of MSCHF; DeelDeelDeel is a global payroll and human resources technology company founded in 2019, whose co-founders are Alex Bouaziz and Shuo Wang. Starting from cross-border contractor contracting and payment services, the company expanded into employer of record, global payroll, HR information, immigration, and IT device management, and has built its own infrastructure by acquiring payroll technology and service teams.Open the full entry CEO Alex BouazizAlex BouazizAlex Bouaziz is co-founder and chief executive officer of Deel, the HR and global payroll software company, which he founded with Shuo Wang at Y Combinator in 2019; he graduated from the Technion – Israel Institute of Technology and the Massachusetts Institute of Technology, and previously co-founded the investment fund Sarona Ventures.Open the full entry; Hellosaurus CEO James Ruben; Beek CEO Pamela Valdes; Facebook product manager Luis Vargas; Block Renovations co-founder Koda Wang; Nebula Genomics CEO Kamal Obbad; and Dave Gilboa, Neil Blumenthal and Jeff Raider, co-founders and executives of Warby ParkerWarby ParkerWarby Parker is a U.S. eyewear and vision-care company founded in 2010 by Neil Blumenthal, Dave Gilboa, Andrew Hunt and Jeffrey Raider, and headquartered in New York. Starting with direct online sales, it expanded into stores, contact lenses and eye exams, and is developing intelligent eyewear with Google and Samsung. Its shares trade on the New York Stock Exchange under WRBY.Open the full entry and Harry’s, among others.⁠[11]

TechCrunch wrote on February 2, 2021 that Millions was giving away money roughly monthly through its Twitter account, @millions: users followed the account, visited Millions.app and entered six numbers, and matching all six won $1 million, with $10,000 as a grand prize guaranteed to one person; the company also planned a game called “are you my number neighbor?” that would award $100,000 to users whose phone number was one digit off from the number on the site. The article says that the stunts were meant to build brand awareness and acquire customers without advertising, and later to move them to the company’s planned fintech product, which would reward everyday behavior such as swiping a credit card; the co-founder interviewed asked to remain anonymous and said: “The Millions way is really giving the people the money.”⁠[11]

Fortune wrote on February 3, 2021 that Millions was keeping its founders behind a curtain; the company offered up to $1 million to anyone who won a pick-six lottery-style contest on its site and gave smaller random payouts, with $30 to $100 seeming standard, to its Twitter followers, of whom there were more than 19,000 at the time; players picked six numbers from 1 to 99, the odds of matching all six in the first drawing were 1 in 1,120,529,256, and there were 10 drawings in total. The article says that Millions had raised $3 million in seed funding to date, with investors including Biz Stone, Jeff Raider and 8VC.⁠[12]

The Knot API page on Product Hunt lists Kieran O’Reilly and Rory O’Reilly as makers and describes the product as “Cancel subscriptions, update cards/passwords, and more,” adding that “Knot API is for when there’s not an API!”, letting customers update card details, passwords and subscriptions at the merchants they use; the page shows that it launched in 2022 and was ranked fourth of the day on August 30, 2022.⁠[13]

On November 21, 2022, Descoped, the payments-security podcast of Very Good Security, published an interview with him titled “Building Fintech’s Next Account Plumbing with Rory O’Reilly.” The episode description says that Rory O’Reilly and his brother are serial entrepreneurs who founded a GIF company after dropping out of Harvard University and went on to create two fintech startups, Millions and Knot API; the topics include growing a fintech social media following, building “account plumbing” for merchants, and his founder journey.⁠[14]

On August 3, 2023, Knot announced a $10 million Series A round led by Nava VenturesNava VenturesNava Ventures is an early-stage venture capital firm founded by Freddie Martignetti. It has led Series A rounds for companies including Knot, Caden, Grifin and Plato.Open the full entry, with participation from Amex Ventures, the venture arm of American ExpressAmerican ExpressAmerican Express Company is a payments company headquartered in New York that issues credit and charge cards and operates its own payments network; founded in 1850, it is listed on the New York Stock Exchange.Open the full entry, and PlaidPlaidPlaid is a financial technology company co-founded by Zach Perret and William Hockey and headquartered in San Francisco. It provides infrastructure connecting financial accounts with applications, with products spanning account verification, payments, lending and fraud prevention, and develops AI models for financial transactions. A planned acquisition by Visa was terminated in 2021.Open the full entry; AxiosAxiosAxios is a US digital news media company founded in 2016 by former Politico executives Jim VandeHei, Mike Allen, and Roy Schwartz and launched in January 2017. It is known for short news items and industry newsletters in the “Smart Brevity” style, especially for its Washington political coverage, and publishes local news newsletters in cities across the United States through Axios Local. Since 2022 it has been owned by Cox Enterprises.Open the full entry writes that the backers also included former American Express CEO Kenneth Chenault, DraftKings CEO Jason Robins and Jason Mikula, author of Fintech Business Weekly, and Finovate writes that more than 20 CEOs and founders also took part. Finovate writes that Knot was founded in 2019, is headquartered in New York, raised a $3 million seed round in 2021 and had raised $13 million in total.⁠[15][16][17]

Axios writes that Knot API, led by CEO Rory O’Reilly, lets customers of banks and fintechs switch the payment method saved at merchants such as NetflixNetflixNetflix is a U.S. entertainment company that offers streaming series, films, games, and live programming, headquartered in Los Gatos, California. Founded in 1997, it grew from online DVD rental into an international subscription entertainment service and also runs original content, advertising, and in-person experience businesses.Open the full entry and AmazonAmazonAmazon is a publicly traded U.S. technology and retail company founded by Jeff Bezos in 1994, with its principal corporate offices in Seattle. Its businesses span e-commerce, logistics and fulfillment, digital advertising, membership and entertainment services, consumer electronics, and Amazon Web Services cloud computing.Open the full entry to a new card in one step inside the bank’s app and manage and cancel subscriptions there, and that it was exploring products to help customers negotiate bills; he said: “We come in after customers have already signed up to make sure that they don’t end up churning.” Finovate writes that Knot’s interface lets card issuers update card-on-file information across its merchant network, including WalmartWalmartWalmart is an American retailer founded by Sam Walton in 1962, with businesses spanning physical retail, membership warehouse clubs, e-commerce and related services. Its businesses include Walmart and Sam’s Club, and it has expanded into other markets through international investments; its shares trade on Nasdaq under the ticker WMT.Open the full entry, Netflix, Amazon, StarbucksStarbucksStarbucks is a publicly traded coffee company headquartered in Seattle, founded in 1971 by Jerry Baldwin, Gordon Bowker and Zev Siegl. Howard Schultz subsequently developed its coffeehouse model and international expansion. It operates company-owned and licensed coffeehouses and sells packaged coffee through partners. Its shares trade on Nasdaq under SBUX.Open the full entry and UberUberUber is a technology company headquartered in San Francisco, United States, whose legal name is Uber Technologies, Inc. Co-founded by Garrett Camp and Travis Kalanick, it uses digital platforms to connect riders with drivers, delivery consumers with merchants, and shippers with carriers, with main businesses in Mobility, Delivery, and Freight. Dara Khosrowshahi has been chief executive officer since 2017.Open the full entry, with a few lines of code, and that it offered a subscription-cancelling tool while an account-creation tool and a password updater were in development.⁠[16][17]

Axios writes that neobanks have historically struggled to become the primary account, a problem O’Reilly knows well: his last startup, a challenger bank called Millions, gathered 50,000 customers but had trouble getting users to spend repeatedly on its card. In the funding announcement he said: “Securing this Series A funding signifies the immense trust our investors have in Knot’s potential,” describing that potential as revolutionizing the way card issuers manage their customers’ payment methods, and added: “We’re grateful for the chance to further our mission of building a financially interconnected future.”⁠[16][17][15]

His brother Kieran O’Reilly has been his partner in each of his ventures: the two co-founded GIFYouTube (later gifs.com), Millions and Knot. He wrote on Product Hunt that his brother was the co-founder and chief technology officer of gifs.com and also a Thiel Fellow; the Knot API page on Product Hunt likewise lists both brothers as makers.⁠[14][4][13]

Thiel Fellowship: Official website: https://thielfellowship.org/ (opens in a new window).⁠[18]