Good morning. It’s Thursday, May 29. Today we are covering:
Apple to Rebrand Its Device Operating Systems to Mark Major Overhaul
Telegram Signs $300M Deal With Elon Musk's xAI to Integrate Grok AI Into Its Messaging App
Microsoft wants Windows Update to handle all apps
Luther Lowe of Y Combinator: 'It's really important to fight for Little Tech'
Let’s dive in
By Sahil Lavingia via sahillavingia.com
Sahil Lavingia recounts his experience joining the VA as a $0-salary Senior Advisor to the Chief of Staff, grappling with restrictions like a locked-down government laptop that blocked basic developer tools.
The piece highlights structural reasons why the VA outsources much of its software, citing systemic hurdles to effective internal tech work.
It references the presidential DOGE Order, mandating each agency to form a DOGE Team of four—including an engineer and attorney—to drive tech reform in coordination with USDS.
𝕏: My experience working as a software engineer for the Department of Veterans Affairs, on behalf of DOGE. - Sahil Lavingia (@shl)
Apple to Rebrand Its Device Operating Systems to Mark Major Overhaul
By Mark Gurman via Bloomberg
Apple is rebranding its operating systems with names based on the year rather than version numbers, starting with iOS 26, macOS 26, and others.
The new naming convention will span across all platforms, including iPadOS 26, watchOS 26, tvOS 26, and visionOS 26.
This shift is part of a broader software redesign initiative aimed at unifying the user experience across all Apple devices.
𝕏: NEW: Apple will announce its biggest ever software rebrand at WWDC, tied to operating system redesigns. Apple is moving from version numbers to years (like Windows in the 90s). The new OSs: iOS 26, iPadOS 26, macOS 26, visionOS 26, tvOS 26, watchOS 26. - Mark Gurman (@markgurman)
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Telegram Signs $300M Deal With Elon Musk's xAI to Integrate Grok AI Into Its Messaging App
By Oliver Knight via CoinDesk
Telegram has signed a $300 million deal with Elon Musk's xAI to integrate the Grok AI assistant into its messaging platform, including a one-year partnership with revenue sharing on xAI subscriptions sold via Telegram.
The deal coincides with Telegram's plans to raise $1.5 billion through a bond sale backed by BlackRock, Citadel, and Mubadala to refinance its 2021 debt.
Following the announcement, the TON token—Telegram's native cryptocurrency—jumped 18.5%, climbing from $3.28 to $3.55 in less than a day.
𝕏: This summer, Telegram users will gain access to the best AI technology on the market. @elonmusk and I have agreed to a 1-year partnership to bring xAI’s @grok to our billion+ users and integrate it across all Telegram apps… - Pavel Durov (@durov)
Microsoft wants Windows Update to handle all apps
By Tom Warren via The Verge
Microsoft is previewing a new Windows Update orchestration platform that allows any app or driver to be updated via Windows Update, with a focus on business apps but open to all developers.
The platform supports scheduled updates based on user activity, battery status, and sustainability goals, and integrates with native Windows Update notifications and update history.
It aims to unify app updates for MSIX/APPX and some Win32 apps, potentially replacing proprietary updaters from developers like Adobe, while also offering automatic access to future improvements in the update system.
𝕏: Microsoft wants Windows Update to handle all apps. A new preview lets any developer update their apps through Windows Update. - Tom Warren (@tomwarren)
Luther Lowe of Y Combinator: 'It's really important to fight for Little Tech'
By Tim Bradshaw via Financial Times
Luther Lowe, a former Yelp policy chief and now Y Combinator’s first full-time lobbyist, is championing “Little Tech” in Washington and Brussels, advocating for start-ups on issues like immigration, market access, and open-source AI to counterbalance Big Tech’s outsized influence.
Under Lowe’s direction, YC has notched key lobbying wins—such as helping defeat California’s SB 1047 on AI regulation and blocking federal copyright legislation that threatened a YC-backed company—while launching initiatives like the American Innovators Network with Andreessen Horowitz to monitor state-level AI policy.
Lowe argues that Big Tech's dominance stifles innovation, citing cases like Beeper Mini’s clash with Apple and the lack of LLM integration in Siri and Alexa, and stresses the importance of safeguarding open-source AI from overregulation to maintain the U.S.'s competitive edge against China.
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