Not the best kickoff to the long weekend: markets sold off today on fears that President Trump’s plan to double tariffs on Chinese imports and restrict exports of “critical software” will extend the administration’s trade war with China into chips and enterprise software. CNBC has more here.

SoftBank CEO Masayoshi Son is negotiating a $5 billion margin loan backed by Arm shares to fund additional investments in OpenAI as he accelerates the company’s $30 billion push into AI and U.S. data infrastructure. Bloomberg has more here.

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By Connie Loizos

Chris Lehane is one of the best in the business at making bad news disappear. Al Gore’s press secretary during the Clinton years, Airbnb’s chief crisis manager through every regulatory nightmare from here to Brussels – Lehane knows how to spin. Now he’s two years into what might be his most impossible gig yet: as OpenAI’s VP of global policy, his job is to convince the world that OpenAI genuinely gives a damn about democratizing artificial intelligence while the company increasingly behaves like, well, every other tech giant that’s ever claimed to be different.

I had 20 minutes with him on stage at the Elevate conference in Toronto earlier this week – 20 minutes to get past the talking points and into the real contradictions eating away at OpenAI’s carefully constructed image. It wasn’t easy or entirely successful. Lehane is genuinely good at his job. He’s likable. He sounds reasonable. He admits uncertainty. He even talks about waking up at 3 a.m. worried about whether any of this will actually benefit humanity.

But good intentions don’t mean much when your company is subpoenaing critics, draining economically depressed towns of water and electricity, and bringing dead celebrities back to life to assert your market dominance.

The company’s Sora problem is really at the root of everything else. The video generation tool launched last week with copyrighted material seemingly baked right into it. It was a bold move for a company already getting sued by the New York Times, the Toronto Star, and half the publishing industry. From a business and marketing standpoint, it was also brilliant. The invite-only app soared to the top of the App Store as people created digital versions of themselves, OpenAI CEO Sam Altman; characters like Pikachu, Mario, and Cartman of “South Park”; and dead celebrities like Tupac Shakur.

Asked what drove OpenAI’s decision to launch this newest version of Sora with these characters, Lehane gave me the standard pitch: Sora is a "general purpose technology" like electricity or the printing press, democratizing creativity for people without talent or resources. Even he – a self-described creative zero – can make videos now, he said on stage.

What he danced around is that OpenAI initially “let” rights holders opt out of having their work used to train Sora, which is not how copyright use typically works. Then, after OpenAI noticed that people really liked using copyrighted images, it "evolved" toward an opt-in model. That's not really iterating. That's testing how much you can get away with. (And by the way, though the Motion Picture Association made some noise last week about legal threats, OpenAI appears to have gotten away with quite a lot.)

1Password, a 20-year-old Toronto startup that helps users store and manage passwords, completed a $100 million secondary transaction at a $6.8 billion valuation. Investors included The Halo Fund, which purchased $75 million in shares, and Flume Ventures. Bloomberg has more here.

Anysphere, a four-year-old San Francisco startup that develops Cursor, an AI-powered coding environment that helps software engineers write, edit, and debug code more efficiently, is reportedly considering raising a round at a $30 billion valuation. The Information has more here.

David AI, a two-year-old San Francisco startup that creates and sells audio datasets to train artificial intelligence models, raised a $50 million Series B round at a $500 million valuation. The deal was led by Meritech Capital, with additional participation from NVentures, First Round Capital, Y Combinator, Alt Capital, and Amplify Partners. More here.

Govini, a 14-year-old company based in Arlington, VA, that builds AI software to modernize the U.S. defense supply chain, raised a $150 million round from Bain Capital. CNBC has more here.

Kalshi, a six-year-old New York startup that operates an online prediction-market platform, raised a $300+ million round at a $5 billion valuation in a round co-led by Sequoia Capital and Andreessen Horowitz, with Paradigm, CapitalG, and Coinbase Ventures also investing. TechCrunch has more here.

Yendo, a five-year-old Dallas startup that offers AI-powered, vehicle-secured credit cards and other asset-backed credit products for underserved consumers, raised a $50 million Series B round. Investors included Spice Expeditions, Autotech Ventures, FPV Ventures, Pelion Venture Partners, Mark Cuban, and Clocktower Technology Ventures. More here.

Benable, a three-year-old San Francisco startup that operates a platform where people can create and share personal recommendations for products, places, and services with others online, raised an $11 million seed round led by Footwork, with Third Prime, PJC, and Jack Altman also investing. More here.

Foundation Health, a two-year-old San Francisco startup that uses AI to help pharmacies and healthcare providers automate tasks like patient communication, prescription refills, and medication approvals, raised a $20 million Series A round led by Define Ventures, with Vanderbilt University and Intermountain Ventures also contributing. The company has raised a total of $26 million. Mobi Health News has more here.

Prezent, a four-year-old startup based in Los Altos, CA, that offers an AI-powered presentation builder for enterprises, raised a $30 million round at a $400 million post-money valuation. The deal was co-led by Multiplier Capital, Greycroft, and Nomura Strategic Ventures, with Emergent Ventures, WestWave Capital, and Alumni Ventures also participating. The company has raised a total of $74+ million. TechCrunch has more here.

Routefusion, a seven-year-old Austin startup that helps financial institutions and platforms manage cross-border payments, accounts, and compliance through a single API, raised a $26.7 million Series A round led by PeakSpan Capital, with Silverton Partners, Initialized Capital, and Forum Ventures also participating. The company has raised a total of $40.7 million. Crunchbase News has more here.

Sensi.AI, a five-year-old Israeli and Austin startup that uses AI to monitor, analyze, and improve senior care through audio-based detection and automation tools, raised a $45 million Series C round led by Qumra Capital, with participation from Zeev Ventures, Insight Partners, Entrée Capital, Flint Capital, and Jibe Ventures. The company has raised a total of $98+ million. CTech has more here.

Bondu, a one-year-old San Francisco startup that makes AI-powered toys designed to provide companionship for children, raised a $5.3 million seed round led by Makers Fund, with Samsung Ventures, Boost VC, and Founders Inc also taking part. GamesBeat has more here.

Echelon, a three-year-old startup based in Washington, DC, that automates enterprise IT implementation and operations using AI agents, raised a $4.75 million seed round. Bain Capital Ventures led the investment. More here.

Focal, a one-year-old San Francisco startup that develops an AI productivity platform for financial advisors, raised a $5 million seed round. Distributed Ventures and Wischoff Ventures were the co-leads. More here.

Mentium, a three-year-old Austin startup that develops AI “digital workers” to automate back-office tasks for freight brokerages and logistics companies, raised a $3.2 million seed round led by Lerer Hippeau, with Matchstick Ventures, Tower Research Capital, Antler, and MBA Ventures also pitching in. FreightWaves has more here.

Oasiz, a San Francisco startup founded this year that lets users instantly create and share multiplayer games that blend social video and interactive play, raised a $2.5 million seed round co-led by Andreessen Horowitz and The Venture Reality Fund. Digital Music News has more here.

Parallel, a two-year-old Salt Lake City startup that offers an AI-driven finance platform combining forecasting software with fractional CFO support for early-stage companies, raised a $2.4 million seed round co-led by Night Capital and K5 Tokyo Black and including Penny Jar Capital, Background VC, Mintaka VC, and Path Ventures. More here.

Pavus AI, a one-year-old New York startup that uses artificial intelligence to help procurement teams organize internal and market data to improve margins and sourcing decisions, raised a $5.3 million seed round led by Sentinel Global. SiliconANGLE has more here.

Previvor Edge, a one-year-old New York startup that runs a clinical program for personalized cancer prevention and early detection, raised a $3.3 million pre-seed round co-led by CoFound Partners and Max Ventures, with Humbition Capital, Red Swan Ventures, and Designer Fund also stepping up. Femtech Insider has more here.

Sitehop, a five-year-old startup based in Sheffield, UK, that develops quantum-ready encryption hardware for faster, more energy-efficient data protection, raised a $10 million round led by Northern Gritstone, with Amadeus Capital Partners, Manta Ray, Mercia Ventures, and Mercia Equity Finance also anteing up. Tech Funding News has more here.

Smallest.ai, a one-year-old Indian startup that develops ultra-fast speech generation models for enterprise use, raised an $8 million seed round led by Sierra Ventures, with 3one4 Capital and Better Capital also joining in. SiliconANGLE has more here.

Unikraft, an eight-year-old German startup that develops cloud infrastructure using unikernel technology to reduce the cost and complexity of AI workloads, raised a $6 million seed round led by Heavybit, with Vercel Ventures, Mango Capital, Firestreak, Fly VC, and First Momentum Ventures also opting in. More here.

Waldo, a two-year-old New Orleans startup that builds AI software that helps marketing and creative teams quickly generate insights, briefs, and campaign ideas by automating research and strategy work, raised a $10 million Series A round led by Footwork, with Boldstart Ventures, Alt Capital, Sunflower Capital, and The New Normal Fund also digging in. More here.

Worktrace AI, a San Francisco startup founded this year that helps large companies automate repetitive tasks by observing employee workflows, is said to be raising a $5 million seed round at a $50 million valuation, with backing from OpenAI insiders including Thinking Machines Lab CEO Mira Murati. Business Insider has more here.

Turkish entrepreneurship ecosystem ranked among the top 10 in EMEA. TÜSİAD’s report highlights the ecosystem’s growth in recent years and its potential as a regional entrepreneurship hub for tech companies. Türkiye ranks in the top 10 in the EMEA across several verticals: gaming, fintech and defense. With 3,000+ startups, unicorns, tax advantages, young and digital friendly population, the ecosystem opens its doors to global entrepreneurs and investors who embody the spirit of entrepreneurship. Learn more about the Turkish entrepreneurship ecosystem.

NSO Group, a 15-year-old Israeli company known for its Pegasus spyware that has been used by governments to hack phones, was acquired by a U.S. investment group led by Hollywood producer Robert Simonds in a deal valued in the tens of millions of dollars. TechCrunch has more here.

Campus, a three-year-old New York startup that offers accredited online associate degrees and is backed by Sam Altman, Shaquille O’Neal, and Peter Thiel’s Founders Fund, acquired Los Angeles-based Sizzle AI, an educational AI company founded by former Meta AI chief Jerome Pesenti, and named Pesenti its CTO. Terms were not disclosed. CNBC has more here.

Apple is reportedly acqui-hiring Prompt AI, the two-year-old Berkeley computer vision startup behind the Seemour home security app. CNBC has more here.

Navan, a 10-year-old Palo Alto company that makes corporate travel and expense software, set its IPO price range at $24 to $26 a share for a valuation of up to $6.5 billion, roughly $3 billion below its 2022 private round backed by Andreessen Horowitz, Lightspeed, and Greenoaks. CNBC has more here.

Meta’s metaverse chief Vishal Shah is urging employees to use AI to “go 5X faster” across all workflows, underscoring Mark Zuckerberg’s push for automation even as engineers warn that AI-generated code is creating mounting technical debt. Wired has more here.

Salesforce CEO and longtime San Francisco benefactor Marc Benioff said he now fully supports President Trump and wants National Guard troops sent to the city to combat crime, marking a sharp political turn for one of tech’s most prominent philanthropists. TechCrunch has more here.

In a series of off-the-record lectures over the last month, Peter Thiel has told San Francisco audiences that Greta Thunberg and other critics of AI are “legionnaires of the Antichrist,” casting efforts to regulate technology as a spiritual threat to human progress. The Washington Post has more here.

Andreessen Horowitz has hired former VMware CEO Raghu Raghuram as a general partner for its AI infrastructure and growth teams, with Ben Horowitz naming him managing partner to help run the firm and deepen its leadership bench. More here.

A tiny nonprofit that helped shape California’s new AI safety law has accused OpenAI of using subpoenas and intimidation tactics to silence critics and weaken the legislation, sparking backlash within OpenAI and across the broader AI policy world. Fortune has more here.

Famed roboticist and iRobot founder Rodney Brooks has sounded the alarm on a humanoid robot investment bubble. He’s not the only one. TechCrunch has more here.

Chainalysis, the New York blockchain analytics company, estimated that $75 billion in crypto tied to illicit activity could be seized by governments, potentially accelerating efforts to create national digital-asset reserves as enforcement and policy converge. Cointelegraph has more here.

Atdhe Trepca, the filmmaker behind Are You Happy?, has turned his street interviews asking strangers about happiness into a TikTok-driven social franchise with more than 15 million monthly viewers, revealing a surprising global appetite for unscripted vulnerability.

Rolling Stone on the 250 greatest songs of the 21st century so far.

Italian design house Zagato just unveiled the $3.2 million Capricorn 01, a handbuilt supercar with an 888-horsepower V8, carbon fiber body, and five-speed manual transmission that can hit 60 mph in under three seconds.

An underwater jetpack.

AI isn’t just for productivity anymore. It is quickly becoming entertainment. Consumers are beginning to engage with AI in new ways, fueling the rise of AI companions that combine conversation, play, and personality. These companions are creating entirely new forms of interaction and signaling a major shift in how technology will be experienced. Have a portfolio company interested in exploring AI companions? Reach out to Genies here or learn more about their tech stack for AI companions here. 

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