Ari Weinstein

He grew up in Mount Airy, Philadelphia. His parents are Ken and Judy Weinstein; his father, Ken Weinstein, is a Mount Airy developer. He has two younger brothers, Evan and Noah.⁠[1][2]

The Philadelphia Inquirer wrote in 2009 that as a baby he was fascinated by light switches, and that his late grandfather, Norman, held him for hours so that he could flip them; his father said, “It wasn’t about the lights but trying to figure out how they worked.” The article said that by the age of two he had mastered the family television, stereo and VCR and was taking apart mechanical toys, and that at six he took apart an old computer, put it back together and was delighted when it still worked.⁠[2]

At 11 he got an iPod mini and, wanting more games than the four Apple had installed, taught himself some programming to add more. 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’s Matthew PanzarinoMatthew PanzarinoMatthew Panzarino is a technology journalist and content executive, a former TechCrunch editor-in-chief who announced his appointment as GrowthX chief content officer in 2025.Open the full entry wrote in 2017 that he had followed Weinstein’s work since the iPod Linux days, and called him a former iPhone jailbreaker.⁠[2][3]

In April 2007 he met Ben Feldman, who is the same age, at a bar mitzvah, and the two later became business partners. That year he received an iPod touch as a bar mitzvah present; he said, “It was natural for me to say I want this to do more than Apple has it do.”⁠[2]

On October 14, 2007, he and Ben Feldman released iJailBreak.com, which was downloaded more than a million times and drew a few thousand dollars in donations from users. The two also started a backup-server business for websites, which folded quickly; he said corporations would not trust a small business run by kids.⁠[2]

With six other teenagers whom he had never met face to face, collaborating online, he built software that lets iPhone owners install unauthorized applications. The Philadelphia Inquirer wrote that they jailbroke the iPhone 3GS within two weeks of its June 19 release and that more than 250,000 people downloaded the tools from Purplera1n.com. He said, “It’s really cool to have people using my software to do awesome things with their phones.”⁠[2]

He said, “since I paid a lot of money for this device, I should be able to put any application on it”; he consulted family friends who are lawyers and contended that providing unauthorized iPhone applications is legal under the Digital Millennium Copyright Act. Apple disagreed: an Apple spokeswoman said that the vast majority of customers do not jailbreak their iPhones, for good reason, and that such hacks violate the warranty and cause the iPhone to become unstable and not work reliably; Apple had filed documents with the U.S. Copyright Office challenging the legality of such applications, with a ruling expected that fall. If the ruling favored Apple, he said, “I will have to stop doing it.”⁠[2]

On July 10, 2009, Technical.ly wrote that he, 15 and just finished with ninth grade at Germantown Friends School, had been featured that week in a Wall Street JournalThe Wall Street JournalThe Wall Street Journal is a U.S. news publication founded in 1889, with a focus on business, finance and economics. It is published by Dow Jones, part of News Corp.Open the full entry cover story; it called him the youngest Mount Airy-based hacker it had featured, wrote that he was “getting job offers from Israel and all over the place,” and said he was due to appear on Fox 29 that Monday morning. At the time of writing he was at summer camp on the West Coast.⁠[4]

The same post said he contributed to iJailBreak.com, which it described as a blog about installing unapproved software on Apple’s iPhone and iPod touch.⁠[4]

On July 27, 2009, The Philadelphia Inquirer published a profile of him. It gave his age as 15, said he was about to begin his sophomore year at Germantown Friends School, and said that he blogged as “AriX” at Ariweinstein.com, had about 1,100 Twitter followers, and had created websites and launched business ventures. It added that his parents had been fielding requests for media interviews since The Wall Street Journal’s story on the teenagers’ software.⁠[2]

It said that he and Ben Feldman were developing DeskConnect, a subscription service that would let people reach the files and screens of their home computers from other devices through a website, and that they expected the Mac version to launch shortly after school started that fall.⁠[2]

He said, “I want to go into something computer-related when I’m older,” though he did not yet know what, and “I’d love to own a business,” adding, “I love seeing how things work.” His technology teacher, Matt Zipin, said, “Ari is unusual in that his skill set is fairly narrow but really deep.”⁠[2]

In 2013 he co-founded Workflow, an iPhone automation app. 9to5Mac wrote that he built it into a powerful iPhone automation tool despite the limits Apple placed on third-party apps. AppleInsider wrote that the company that built Workflow was DeskConnect, of which he was chief executive and co-founder.⁠[5][6]

Technical.ly wrote that Workflow began as a project at the University of MichiganUniversity of MichiganThe University of Michigan is a university founded in Detroit in 1817 that moved to Ann Arbor, Michigan, in 1837; it is governed by a statewide-elected Board of Regents and also has campuses in Dearborn and Flint.Open the full entry’s MHacks hackathon. Federico Viticci of MacStories wrote that he and his team first teased Workflow in January 2014.⁠[7][8]

On August 29, 2013, DeskConnect, made by him and Ben Feldman, launched for free on both the Mac and iOS App Stores. Engadget referred to him as Ari “AriX” Weinstein.⁠[9]

Engadget described the Mac version of DeskConnect as living in the menu bar and monitoring the clipboard and the frontmost application window: an image could be dragged onto the menu bar to send it to a chosen iOS device, and map directions could be sent from the menu and opened immediately on the device; web links opened in Safari (or Chrome), and other files could be opened with an appropriate iOS app; it also integrated with the Mac’s Contacts so that a phone number could be sent or dialed in one step. On iOS, photos, clipboard contents, documents and websites (through a Safari bookmarklet) could be sent to the Mac, and received items stayed in the app’s “tray” for 30 days. It supported iOS 6 and devices as old as the iPhone 3GS.⁠[9]

On June 5, 2014, the Thiel Foundation announced the new class of its 20 Under 20 Fellowship, and he was selected for 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. The class named 20 teenagers, each of whom received $100,000 over two years to launch a business and had to drop out of college; they were expected to be largely self-guided, with mentoring from former fellows and other entrepreneurs and investors, and were encouraged but not required to move to the San Francisco area. The list published by Entrepreneur gives him as item 20 with only his name and a video, without age, hometown or project; the same list says that Conrad Kramer was working with another Thiel Fellow on software to move websites, documents and photos between a desktop and a mobile device.⁠[10]

Technical.ly wrote on June 25, 2014, that he, 20, was a Thiel Fellow who had taken leave from the Massachusetts Institute of Technology to pursue software development, and that Conrad Kramer would move to San Francisco for the fellowship and work with him on DeskConnect, an app for transferring photos and other files between devices with one touch. It said that he had co-founded DeskConnect with Ben Feldman, also 20 and a native of Northeast Philadelphia.⁠[1]

On October 14, 2026, First Round Review, looking back on the early years of the Thiel Fellowship, cited Workflow as an example of a company founded by fellows, started by him and Conrad Kramer as 2014 fellows and later bought by Apple to become Shortcuts; it added that the two then started another company that was acquired by OpenAI in 2025.⁠[11]

Federico Viticci of MacStories wrote on the day Workflow was released that it was available on the App Store at $2.99. He and his team built ContentKit, a custom iOS framework that powers the app’s Content Graph, which he called “an important technology.”⁠[8]

On December 17, 2014, Technical.ly wrote that the app was built by a team including two current Thiel Fellows who grew up in the Philadelphia area, Conrad Kramer and him; it lets users string together multiple actions and apps to make their own app, a more versatile IFTTT. The article said 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 users and the App Store liked it, and that Workflow had reached the top of the App Store’s paid app list.⁠[7]

In 2015 Workflow won an Apple Design Award, largely for its accessibility work, especially its VoiceOver implementation.⁠[3][12]

On March 22, 2017, Matthew Panzarino of TechCrunch wrote that Apple had acquired Workflow, buying not only the app but also the team: Weinstein, Conrad Kramer, Ayaka Nonaka and Nick Frey. Apple confirmed the deal; its price was not disclosed. Unusually for Apple, Workflow stayed on the App Store and became a free download later that day.⁠[3][12][13]

In a statement he said that the team had “worked closely with Apple from the very beginning,” having started the company as students attending WWDC; Panzarino described the team members as one-time WWDC student scholarship recipients. Panzarino also wrote that Workflow had raised an unannounced seed round, which he was hearing was a couple million dollars, from Lowercase, Eniac and General CatalystGeneral CatalystGeneral Catalyst (GC) is an investment firm founded in 2000 and headquartered in San Francisco, United States, created by Joel Cutler, David Fialkow and Bill Fitzgerald, that backs companies from the seed stage through growth.Open the full entry, and judged the deal a solid payday for the team and a small upside for investors.⁠[3]

Apple’s statement confirming the deal praised Workflow’s accessibility work, pointing to its “clearly labeled items” and “thoughtful hints.”⁠[12]

The next day Technical.ly covered the deal under the headline “A crew of Philly whiz kids just sold their automation app to Apple,” noting that Conrad Kramer is from Cherry Hill, New JerseyNew JerseyNew Jersey is a state in the eastern United States on the Atlantic Ocean, bordered by New York State, Delaware, and Pennsylvania, with the Hudson River forming its northeastern boundary and the Delaware River its western boundary; its capital is Trenton and its largest city is Newark. One of the original 13 colonies, it became the third state to ratify the U.S. Constitution on December 18, 1787, and its population in the 2020 census (April 1, 2020) was 9,288,994.Open the full entry, that Ayaka Nonaka graduated from PennUniversity of PennsylvaniaThe University of Pennsylvania, commonly called Penn, is a private research university and Ivy League member in Philadelphia. It traces its origins to a 1740 charity-school project; Benjamin Franklin proposed his academy in 1749, classes began in 1751, and a 1791 merger established the institution under its present name. Penn has 12 schools, with undergraduate education concentrated in arts and sciences, engineering, nursing and Wharton. Enrollment totaled 29,384 in fall 2025, and the fiscal 2025 endowment was $24.81 billion. As of October 2026, J. Larry Jameson was president, with his term scheduled to end on June 30, 2027.Open the full entry in 2013 and had worked at Venmo, and that Nick Frey went to high school in IowaIowaIowa is a state in the Midwestern United States; its capital and largest city is Des Moines. It was admitted to the Union on December 28, 1846, as the 29th state, and its population in the 2020 census (April 1, 2020) was 3,190,369.Open the full entry.⁠[13]

After the acquisition he joined Apple as a software engineering manager, working on Shortcuts and other intelligence and “proactive” features. His LinkedInLinkedInLinkedIn is a social networking platform for professionals. It was founded in 2002 by Reid Hoffman and others, launched in 2003, and listed on the New York Stock Exchange in 2011; after Microsoft acquired it for approximately $26.2 billion in 2016, it became a wholly owned Microsoft subsidiary. Its revenue comes from membership subscriptions, advertising, and recruitment solutions.Open the full entry profile lists the role from April 2017 to June 2023.⁠[5][6][14]

At WWDC 2018 he presented the developer session “Introduction to Siri Shortcuts” (Session 211) with his colleague Willem Mattelaer, opening with: “My name is Ari Weinstein, and I’m really excited to be here along with Willem Mattelaer to tell you about Siri Shortcuts.”⁠[15]

Federico Viticci of MacStories wrote that the Shortcuts app announced at that WWDC was the new version of Workflow, offered as a separate app on the App Store, and credited the Workflow (now Shortcuts) team with reframing user automation around Siri and voice.⁠[16]

In June 2023 he announced that he had left Apple “this month after 6 years (9 including Workflow!).” He wrote that he had never imagined Workflow would be preinstalled on every iPhone and power systems like Shortcuts and App Intents, that he had loved Apple and its products since he was a kid, that working there had been a real honor and a lot of fun, and that he was “grateful for this journey and for our team.” Leaving was really tough, he said, but he was excited to take some time off and “build something new.”⁠[5][6]

9to5Mac wrote that the announcement came in a thread on MastodonMastodonMastodon is free and open-source decentralized social networking software created by Eugen Rochko in 2016; based on the ActivityPub protocol, it forms a federated network of independently run servers. Its user base grew sharply in 2022, and Rochko stepped down as CEO in November 2025.Open the full entry, while AppleInsider and MacTech wrote that he posted it on Twitter.⁠[5][6][14]

TechCrunch wrote that he and Conrad Kramer worked at Apple for several years before leaving to found Software Applications Incorporated in August 2023; the third co-founder and chief operating officer, Kim Beverett, spent nearly ten years at Apple as a senior program and product manager on products including Safari, WebKit and Messages.⁠[17]

Federico Viticci of MacStories, in a short post linking to a report by The Verge, wrote that Software Applications Incorporated, the new company of Weinstein, Conrad Kramer and Kim Beverett, aimed to bring generative AI to the desktop in a way that pushes operating systems forward, and that the three were prototyping with a variety of large language models, including OpenAI’s GPT and Meta’s Llama 2, but had no product to show yet. Weinstein said he wanted to recreate “the magic that you felt when you used computers in the ’80s and ’90s”: turning on an Apple II or an Atari gave you a BASIC console where a user could type in code and program the computer to do whatever they wanted, whereas today people use very optimized operating systems with software that is extremely easy to use but “not flexible,” so that with a schedule open in a browser window there is no way just to say “add this to my calendar.” Viticci also noted that the company’s website is a retro, emulated browser version of Mac OS 8.⁠[18]

The company’s “About Us” page says that, to scale up the team, it raised $6.5 million in seed funding from Dylan FieldDylan FieldDylan Field is the co-founder and CEO of Figma and an angel investor. He studied computer science and mathematics at Brown University, explored browser-based design tools with Evan Wallace, and founded Figma in 2012 with support from the Thiel Fellowship. His personal history also includes collecting digital art and investing in companies such as Mercury and Socket.Open the full entry (Figma), Sam AltmanSam AltmanSam Altman is an entrepreneur and investor, and the co-founder and chief executive officer of OpenAI. He previously served as president of Y Combinator and founded the location-based social service Loopt. He also helped found Tools for Humanity and Merge Labs, has invested in energy and life sciences ventures, and has driven public discussion of AI governance, employment, and wealth distribution.Open the full entry (OpenAI) and others; the team works together in person in San Francisco, and its members previously built intelligence, automation and personal-assistant products at startups and at Apple. The 12 team members the page lists include Weinstein, Conrad Kramer and Kim Beverett.⁠[19]

On May 28, 2025, he, Conrad Kramer and Kim Beverett revealed Sky, which they had developed in secret: an AI assistant that can be invoked anywhere on the Mac and controlled with natural language. David Sparks wrote on MacSparky that Sky’s “Skyshots” feature captures both what is on screen and the underlying data when the user holds both Command keys, so that on-screen items can be referred to with words like “this” or “here”; it has built-in integrations with Calendar, Messages, Notes and web browsing, and advanced users can create custom tools with Shortcuts, AppleScript and shell scripts. The website said it would launch that summer, with sign-ups for notifications.⁠[20]

Federico Viticci of MacStories wrote in his preview that Sky brings up a small floating interface with a hotkey and can answer questions and perform actions for any window and any app open on the Mac, using OpenAI’s GPT-4.1 or AnthropicAnthropicAnthropic is an artificial intelligence research and product company founded in 2021 that develops the Claude models, assistant, and tools such as Claude Code, and operates as a public benefit corporation. Dario Amodei and Daniela Amodei are its co-founders, and its research covers model safety, interpretability, and steerability.Open the full entry’s Claude; at the time, actions in system apps required the user’s manual authorization; and Sky was in closed alpha, set to launch later that year with a free tier and more features in a subscription. Weinstein described to Viticci the tension between automation tools and chatbots: “Automation tools are so powerful, but they require this meta understanding of how things work,” and said that Sky “spans that whole spectrum.”⁠[21]

On October 23, 2025, OpenAI announced that it had acquired Software Applications Incorporated, would bring Sky’s deep macOS integration and product work into ChatGPTChatGPTChatGPT is a generative AI assistant launched by OpenAI on November 30, 2022. Through websites and applications, it provides conversation, writing, coding, search, file analysis, and image and voice interaction. It evolved from a free research preview into personal, enterprise and education plans, gradually adding deep research, Study mode and cross-application task execution. Its use has prompted continuing discussions about factual accuracy, personal privacy, copyright, education and teen safety.Open the full entry, and that all members of the Sky team would join OpenAI. As the company’s co-founder and chief executive, he said the team had built Sky as an AI experience that “floats over your desktop” to help people think and create, and that the team was excited to bring that vision to hundreds of millions of people.⁠[22]

OpenAI wrote that the acquisition was led by Nick Turley and Fidji SimoFidji SimoOpenAI advisor and Nscale director.Open the full entry and approved by the independent Transaction and Audit Committees of OpenAI’s board of directors, and disclosed that an investment fund associated with Sam Altman held a passive investment in Software Applications Incorporated. TechCrunch wrote that Sky had not been released to the public, that deal terms were not revealed, and that the company’s investors also included Context Ventures and Stellation Capital.⁠[22][17]

As of November 2026 his X bio reads “Computer Use & Frontier Interfaces @OpenAI” and “Previously founded @SkyBySoftware, Shortcuts at Apple, and Workflow,” and gives his location as San Francisco, 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.⁠[23]

His GitHub profile uses the username AriX, gives his location as San Francisco, California, and his company as Software Applications Incorporated, lists Chronic-Dev among its organizations, and links to his personal website, ariweinstein.com. The site is a single tongue-in-cheek FAQ page that gives his first name as Ari and his last name as Weinstein, says that for fun he makes websites, and answers that his favorite color is purple before correcting itself to blue.⁠[24][25]

Software Applications Incorporated: Official website: https://software.inc/ (opens in a new window).⁠[26]

OpenAI: Official website: https://openai.com/ (opens in a new window).⁠[22]

Workflow: Official website: https://workflow.is/ (opens in a new window).⁠[27]

DeskConnect: Official website: https://deskconnect.com/ (opens in a new window).⁠[28]

Apple: Official website: https://www.apple.com/ (opens in a new window).⁠[29]

Thiel Fellowship: Official website: https://thielfellowship.org/ (opens in a new window).⁠[30]

Personal website: https://ariweinstein.com/ (opens in a new window).⁠[24][25][2]

X: Public account: https://x.com/AriX (opens in a new window).⁠[24][23]

LinkedIn: Public profile: https://www.linkedin.com/in/weinsteinari/ (opens in a new window).⁠[19][24]

GitHub: Public account: https://github.com/AriX (opens in a new window).⁠[24]