Reddit has agreed to license its data to OpenAI, and OpenAI has also agreed to become a Reddit advertising partner. The news led Reddit's stock to shoot up 11% in after-hours trading. TechCrunch's Kyle Wigger's notes an "unusual angle" to this deal is that OpenAI's CEO Sam Altman has an 8.7% stake in Reddit, making him Reddit's third-largest shareholder; asked about the apparent conflict of interest, an OpenAI spokesperson told Wiggers that Altman, who is a member of OpenAI’s board, recused himself for the decision.

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By Sarah Perez

This week, at Google’s I/O developer conference, the company made its case to developers — and to some extent, consumers — why its bets on AI are ahead of rivals. 

At the event, the company unveiled a revamped AI-powered search engine, an AI model with an expanded context window of 2 million tokens, AI helpers across its suite of Workspace apps, like Gmail, Drive and Docs, tools to integrate its AI into developers’ apps and even a future vision for AI, codenamed Project Astra, which can respond to sight, sounds, voice and text combined.

While each advance on its own was promising, the onslaught of AI news was overwhelming. Though obviously aimed at developers, these big events are also an opportunity to wow end users about the technology. 

But after the flood of news, even somewhat tech-savvy consumers may be asking themselves, wait, what’s Astra again? Is it the thing powering Gemini Live? Is Gemini Live sort of like Google Lens? How is it different from Gemini Flash? Is Google actually making AI glasses or is that vaporware? What’s Gemma, what’s LearnLM…what are Gems? When is Gemini coming to your inbox, your docs? How do I use these things?

More here.

Alkira, a six-year-old startup based in San Jose, CA, whose platform allows businesses to connect and manage their network infrastructure across multiple cloud providers, raised a $100 million Series C round led by Tiger Global Management, with additional participation from Dallas Venture Capital, Geodesic Capital, and NextEquity Partners as well as previous investors Dallas Venture Capital, Sequoia Capital, Kleiner Perkins, and Koch Disruptive Technologies. TechCrunch has more here.

Cover Genius, a 10-year-old New York company that offers embedded insurance and warranty services for various industries, including retail, travel, fintech, and logistics, raised an $80 million Series E round led by Spark Capital, with previous investors Dawn Capital, King River Capital, and G Squared also participating. PYMNTS has more here.

Cylib, a two-year-old German startup that specializes in recycling lithium-ion batteries, raised a $59.8 million Series A round co-led by World Fund and Porsche Ventures, with Bosch Ventures and DTCF NRW.Venture as well as previous investors Vsquared Ventures, Speedinvest, and 10x Founders also taking part. Electrive has more here.

PolyAI, a seven-year-old London startup that develops AI-powered voice assistants for customer service, raised a $500 million at a valuation of approximately $500 million. Hedosophia and NVentures (aka Nvidia) were the co-leads, with previous investors Khosla Ventures and Point72 Ventures also contributing. Silicon Canals has more here.

Sigma Computing, a 10-year-old company that creates data analytics tools that allow teams to explore and visualize data collaboratively, raised a $200 million Series D round at a $1.5 billion. The deal was co-led by Avenir Growth Capital and Spark Capital, with Snowflake Ventures, Sutter Hill Ventures, D1 Ventures, Xn Ventures, and Altimeter Capital also joining in. The company has raised a total of $581 million. TechCrunch has more here.

Uniquity Bio, a startup based in Malvern, PA, and San Diego that is developing drugs to inhibit the thymic stromal lymphopoietin protein involved in the inflammatory response in diseases like asthma and chronic obstructive pulmonary disease, raised a $300 million round. Blackstone Life Sciences was the lead investor. BioPharma Dive has more here.

Vercel, a nine-year-old San Francisco startup that develops the Next.js framework, raised a $250 million Series E round at a $3.25 billion valuation. Accel was the lead investor, with additional funds provided by previous investors CRV, GV, Notable Capital, Bedrock, Geodesic Capital, Tiger Global, 8VC, and SV Angel. Reuters has more here. 

Colab, a seven-year-old Canadian startup that offers a web-based collaboration tool and issue-tracking platform for engineering teams, enabling them to share and review design files and provide feedback in real-time, raised a $21 million Series B round led by Insight Partners, with Y Combinator, Killick Capital, and Pelorus VC also investing. TechCrunch has more here.

Leya, a one-year-old Stockholm startup that is developing an AI assistant for lawyers and law firms to help with tasks such as reviewing documents, performing due diligence, and drafting legal texts, raised a $10.5 million seed round led by Benchmark, with Hummingbird, SV Angel, and Y Combinator also taking stakes. Tech.eu has more here.

Nabla Bio, a four-year-old startup based in Cambridge, MA, that integrates AI with lab measurements to create high-quality drug candidates, raised a $26 million Series A round. Radical Ventures was the deal lead. Endpoints News has more here.

Steno, a six-year-old Los Angeles startup that provides court reporting and litigation services, including remote depositions and financing options, primarily for law firms, raised a $46 million round led by Left Lane Capital, with Trinity Capital and Rivonia Road Capital also pitching in. The SaaS News has more here.

Watershed Health, an 11-year-old New Orleans company whose platform enables healthcare providers to share patient information instantly, ensuring all doctors and nurses involved in a patient's care have up-to-date records, raised a $13.6 million round led by First Trust Capital Partners, with FCA Venture Partners, Create Health Ventures, Impact Engine, 450 Ventures, LDH Ventures II/Launchpad Digital Health, MassMutual Ventures, Capstar Partners, and Wanxiang Healthcare Investments also piling on. More here.

Acclinate, a four-year-old startup based in Birmingham, AL, that helps to improve the diversity of participants in medical research by connecting healthcare organizations with underrepresented communities, raised a $7 million Series A round led by Cencora Ventures, with Labcorp and Latimer Ventures also investing. More here.

Agora, a five-year-old Israeli and New York startup whose platform is designed to simplify property management for real estate investors, raised a $34 million Series B round led by Qumra Capital, with previous investors Insight Partners and Aleph also stepping up. The company has raised a total of $63 million. TechCrunch has more here.

C/side, a San Francisco startup that develops tools to enhance browser security for third-party scripts, raised a $1.7 million pre-seed round led by Scribble Ventures, with Roar Ventures also anteing up. FinTech Global has more here.

Grasp, a Stockholm startup that is building AI assistants for investment banks and management consultants, raised a $2.1 million round co-led by Yanno Capital and Philian Invest. EU-Startups has more here.

Malted AI, a one-year-old Scottish startup that is developing LLMs for bespoke purposes for clients in areas such as finance and law, raised a $7.6 million round led by Hoxton Ventures, with Creator Fund also chipping in. UKTN has more here.

Numra, a one-year-old Dublin startup that uses AI to streamline complex workflows for finance and accounting teams, raised a $1.6 million round led by Elkstone. Silicon Republic has more here.

Orange Charger, a four-year-old startup based in Menlo Park, CA, that provides affordable electric vehicle charging outlets for apartment buildings, raised a $6.5 million seed round. Munich Re Ventures and Climactic led the round and were joined by Baukunst, Lincoln Properties Ventures, Crow Holdings, and Space Cadet Ventures. TechCrunch has more here.

Phenomix Sciences, a seven-year-old startup based in St. Paul, MN, that develops personalized weight-loss interventions by using biological samples and patient assessments, raised a $5.5 million Series A round. Investors included DexCom, Labcorp, and Health2047. More here.

Recall.ai, a two-year-old San Francisco startup that provides tools that can integrate with major meeting platforms like Zoom, Google Meet, and Microsoft Teams to extract and analyze meeting data, raised a $10 million round led by Ridge Ventures, with Industry Ventures, Y Combinator, IrregEx, Bungalow Capital, and Hack VC also joining in. The company has raised a total of $12 million. TechCrunch has more here.

Spoor, an Oslo, Norway-based startup that uses AI to save birds from wind turbines, has raised $4 million seed round from investors including Futurum Ventures, Nysnø and biodiversity-focused VC Superorganism. The round also included Ørsted Ventures, the venture arm of Ørsted, one of the world’s largest offshore wind farm companies. TechCrunch has more here.

Does your startup have a solution for Responsible AI deployment in the banking sector? Ally is excited to announce the launch of the Ally Innovation Challenge – Responsible AI. Ally is seeking market-ready, US-based startups specializing in AI infrastructure that can assist in building robust, scalable platforms for responsible AI development and deployment. Selected startups will have opportunities for mentoring and potential collaboration with senior experts from the financial services company behind the nation’s largest all-digital bank. Learn more about it here and submit your application by June 17th! Terms and conditions apply - see website for full details

TrueBridge Capital Partners, a Chapel Hill, NC-based fund of funds with stakes in Founders Fund, Accel, Pear and Craft Ventures, among other venture funds, has raised $1.6 billion in commitments across five investment vehicles focusing on venture funds and technology companies: TrueBridge Capital Partners Fund VIII, TrueBridge Seed & Micro-VC II, TrueBridge Direct Fund III, TrueBridge Secondaries I, and TrueBridge Blockchain I. According to TrueBridge, the firm now manages more than $7.5 billion in assets. More here.

OneStream Software, a 14-year-old company based in Rochester, MI, that provides companies with a financial platform to handle tasks like financial consolidation, planning, reporting, and analytics, has filed confidentially to go public.  The company sold a majority stake to KKR in 2019 at a $1+ billion valuation. Other members of its cap table include Tiger Global Management and D1 Capital Partners. Bloomberg has more here. 

Noland Arbaugh, the first person to receive a Neuralink brain implant, tells Bloomberg's Ashlee Vance how the implant has changed his life.

Palmer Luckey ... Silicon Valley war king.

Is Mark Zuckerberg's makeover reflective of a midlife crisis or is it a carefully crafted rebrand?

Replit, an eight-year-old San Francisco startup that has built an AI-powered platform for building, sharing, and shipping software, just laid off 20% of its staff, some 30 employees in total. The company has raised more than $200 million from firms like Andreessen Horowitz and Coatue. The Information has more here.

GoPuff, an 11-year-old Philadelphia company that offers an instant delivery service for everyday essentials, just axed 6% of its staff or 600 people.

Figma has arranged for its employees and shareholders to sell as much as $900 million worth of shares at a $12.5 billion valuation, $7.5 billion less than the Adobe valuation offered when it tried to purchase the company. Reuters has more here.

Fortune digs into what GM can do to save its $10 billion investment in Cruise, which dragged a pedestrian on a San Francisco street last year after she was hit by a separate car driven by a person.

TikTok is testing 60-minute video uploads as it continues to take on YouTube.

In a move sure to endear itself to journalists, Gannett, publisher of USA Today and many other newspapers, has begun to place AI-generated summaries at the top of its news stories. 

Strava, the sports tracking app, is using AI to catch leaderboard cheats.

New York City just rolled out new trash cans to make the Pizza Rat's life hell. 

It's official: tacos and burritos are officially sandwiches. 

Depending on which critic you talk to, King Charles' portrait by noted artist Jonathan Yeo is either a big red "stylistic mess" or "extraordinary."

Boxer and promoter Oscar de la Hoya's 9,000-square-foot Las Vegas mansion overlooking the Strip is a sports lover's dream.

The most complicated watch in the world.