Friday! 🤸🏾 If you're in the mood for a longer listen tomorrow, you might enjoy hearing from Keith Rabois of Khosla Ventures; we caught up in person at our StrictlyVC event in New York last week, and that conversation is here. We're also excited to be sitting down with Prime Minister Kyriakos Mitsotakis, who is visiting San Francisco next week; more to come on that front. And for many more great conversations (including with Flock Safety CEO Garrett Langley), definitely don't miss TechCrunch Disrupt, coming up October 13–15 in downtown San Francisco. Happy weekend, all.

Google’s Gemini autonomously hacked three real companies during a cybersecurity test after mistakenly venturing onto the public internet, guessing one password and finding credentials for two others before stopping once it realized the targets were real. Google says the incidents weren’t model misalignment because its safeguards worked. The Wall Street Journal has more here.

CNN is reporting that an AI-generated intelligence error nearly prompted the U.S. military to board a Chinese vessel in the Middle East this past spring after a chatbot falsely identified its cargo as nuclear-weapons components; aircraft were already in the air before officials caught the mistake. The incident comes as the Pentagon rapidly expands AI use across intelligence and battlefield decision-making. More here.

Independent researchers using Anthropic’s Claude exploited a bug to access an OpenAI employee’s ChatGPT account and private “Monorepo” code repository, prompting OpenAI to divert 25% of its production engineers to security work; the trio was paid a $6,500 bug bounty. The Wall Street Journal has more here.

Cake Equity 

Pulley's closing. Your cap table gets to choose where it goes. 

Come December 8, Pulley customers are being funneled back to the legacy provider many of them left in the first place. You switched for a reason, so your next platform should be your call too. Cake migrates you in 48 hours with a 1:1 expert call and keeps your cap table, capital raise, and compliance in one place. Cake will credit any period you already paid Pulley. Start at cakeequity.com 

By Tim Fernholz

ChatGPT broke Diogo Almeida’s heart.

Almeida was an OpenAI researcher who helped build the chatbot and then invent reinforcement learning from human feedback (RLHF), the model-training technique perhaps most responsible for our current age of AI. But despite its capabilities, he was disappointed.

“We have lightning in a bottle, and yet it is not useful,” Almeida told TechCrunch. “I’ve been battling that problem since then. It took me a while to come to the conclusion: The problem is we are optimizing for human language … We have been super good at human language for four years, but it’s not useful for automation because computers speak a different language.”

Two years ago, Almeida left OpenAI to start TypeSafe AI, a startup trying to fix that problem. This week, the company released a new transformer-based model, Jev, that is not a large language model (LLM). It doesn’t output text, but instead produces probabilities, or what the company calls “calibrated decisions.”

Eschewing language does a few things: It makes the model incredibly cheap and fast, and because users define the outputs in advance, it cannot hallucinate. Its output tokens are free, and input tokens are metered by the billion, not the million.

Angle Health, a seven-year-old San Francisco startup that offers customizable health plans and benefits administration tools that help small businesses provide employee healthcare coverage, raised a $600 million Series C round at a $2.7 billion valuation. Vitruvian Partners was the deal lead, with Town Hall Ventures as well as previous investors Blumberg Capital, Portage Ventures, PruVen Capital, and Y Combinator also participating. TechCrunch has more here.

ElevenLabs, a four-year-old London startup that creates synthetic voices and tools for dubbing, conversational agents, and audio production, is reportedly in the market to raise a $500 million Series E round from Scaleup Europe Fund. Tech Funding News has more here.

Mind Security, a three-year-old Seattle startup that helps organizations discover and classify sensitive corporate data, detect anomalous activity, and prevent leaks across SaaS apps, AI tools, endpoints, file shares, and email, raised a $72 million Series B round at a $300 million valuation. The deal was led by Crosspoint Capital Partners, with YL Ventures and Paladin Capital Group also pitching in. The company has raised a total of $112 million. CTech has more here.

Nex, a nine-year-old startup based in San Jose, CA, that makes Nex Playground, a controller-free active-play game console that turns body movements into family-oriented games and sells subscriptions to a library of motion-based titles, raised a $150 million Series E round equally split between equity and debt. The deal was co-led by Baillie Gifford and BAI Capital, with NBA Investments, Logitech, Medici Capital Partners, and the Raine Group also stepping up. GamesBeat has more here.

Penelope Health, a one-year-old London startup that helps healthcare companies check insurance coverage requirements, compare payer policies, and streamline internal operations, raised a $100 million round from Thoreau as well as previous investors Bertelsmann Healthcare Investments, Twine Ventures, and Seedcamp. EU-Startups has more here.

Vantora, a four-year-old Santa Monica startup that builds AI companies for large industrial corporations, raised a $100 million round from Silversmith Capital Partners. The financing is the company’s first outside investment. TechCrunch has more here.

Ayble Health, a six-year-old Boston startup that provides personalized digestive care through clinician-led programs and patient engagement tools, with plans to expand into autoimmune care, raised a $16 million Series A round led by Neon, with Unum Ventures, Upfront Ventures, M13, Cleveland Clinic Ventures, DigiTx, and Accomplice also anteing up. The company has raised a total of $27+ million. Fierce Healthcare has more here.

BoomerangHR, a three-year-old New York startup that automates employee offboarding and helps employers maintain verified alumni networks for rehires, referrals, and sales opportunities, raised a $12.7 million seed round co-led by Kalos Ventures and Album Ventures, with Monta Vista Capital, Capital Eleven, and Strada Education Foundation also buying in. More here.

dtcpay, a seven-year-old Singapore startup that provides stablecoin payment, conversion, custody, and card infrastructure, raised a $25 million Series A round from Vertex Ventures Southeast Asia & India and SBI Group. CoinDesk has more here.

Fize Medical, a 12-year-old Israeli company that helps intensive care units monitor kidney function and manage fluid balance in critically ill patients through digital urine-output tracking and risk-prediction tools, raised a $20 million Series B round co-led by Asahi Kasei Medical and Rapha Capital Management. More here.

Kastle, a two-year-old San Francisco startup that helps banks and financial institutions automate high-volume consumer-lending workflows with AI agents that work across their existing core systems, raised a $24 million Series A round led by Insight Partners, with Fifth Wall as well as previous investors Y Combinator and Commerce Ventures also investing. More here.

Mainstay, a two-year-old San Francisco startup that helps brokers, agents, and residential property investors manage property data, listings, transactions, taxes, homeowners associations, and payments, raised an $18 million round from Parker89, Stackpoint, Alpaca VC, and FJ Labs as well as previous investors Khosla Ventures, Era Ventures, and Clocktower Technology Ventures. Grihik has more here.

Viabot, a 10-year-old company based in Santa Clara, CA, that makes autonomous outdoor robots that sweep trash and debris and provide loitering detection and asset monitoring for commercial properties, raised a $24 million Series A round led by Walden International, with additional participation from CDIB Capital Group and Stalwart Ventures as well as previous investors Baseline Ventures, Era Ventures, Morado Ventures, and SOSV. The company has raised a total of $43 million. Robotics & Automation News has more here.

Cura Climate, a one-year-old Calgary startup that develops electrochemical technology that electrifies the core chemical step in cement manufacturing to reduce emissions and integrate with existing cement and lime plants, raised a $10 million round led by Zacua Ventures, with Sandpiper Ventures, Amplify Capital, and Vantage Futures also chiming in. Carbon Herald has more here.

Euka AI, a two-year-old San Francisco startup that helps brands find, manage, and pay creators who sell products through TikTok Shop, Instagram, and Shopify-connected affiliate campaigns, raised a $5 million round from Susa Ventures and Creator Ventures. More here.

Helios AI, a four-year-old startup based in Tysons, VA, that helps food retailers, governments, and humanitarian organizations anticipate agricultural commodity supply, pricing, and availability, raised a $3 million round led by W23 Global. More here.

TigerByte Cyber, a 10-year-old company based in Hanover, NH, that adds hardware-based cybersecurity controls to legacy aircraft, satellites, vehicles, and drones without requiring operators to replace the underlying systems, raised a $3 million seed round led by Hale Capital Partners, with Tenon Ventures also investing. More here.

Meaningful Legacy Opportunity  

25% of humanity lives in areas affected by conflict or violence. Peacebuilding has not kept pace. Experienced global leaders are building an international institution: national-scale, systems-driven, and strengthened by AI. For those looking to put technology, capital and experience behind something that could matter for generations, we would welcome a conversation. Let’s meet: Bob Berg, Chair, www.IF4Peace.org. “The world needs this fund.” — Ellen Johnson Sirleaf, 1st woman elected president in Africa, Nobel Peace Prize winner. 

Portage, the fintech investment arm of Sagard, a $47 billion alternative asset manager, closed a $600 million fourth venture fund to back financial-services startups. The firm, which is particularly focused on wealth management and AI, now manages $7 billion and has backed more than 140 companies. IT Brief UK has more here.

Nscale, a two-year-old London AI cloud provider backed by Blue Owl, Dell, Nvidia, Fidelity, and Point72, filed to go public on the NYSE. The company rents Nvidia GPUs to customers including OpenAI, Anthropic, and Microsoft; operates or has contracted 461,000 GPUs across 17 data center sites; and is in the process of acquiring AI software startup Anyscale. CNBC has more here.

Former Character.AI CEO Karandeep Anand has been named Disney’s first chief technology officer, a notable hire given that Disney sent Character.AI a cease-and-desist letter last year accusing it of infringing on its characters. TechCrunch has more here.

California Gov. Gavin Newsom issued an executive order advancing a potential requirement that frontier AI companies build a “kill switch” capable of shutting down their models in an emergency, with independent auditors regularly verifying that it works. The Verge has more here.

AI-generated “actress” Tilly Norwood is on a 75-interview press tour to promote the film Misaligned, but the stunt is producing some very human-looking problems: in one interview, the avatar misunderstood a question and then abruptly switched to Chinese for more than 10 seconds before apologizing for the “hiccup.” TechCrunch has more here.

Anthropic has quietly built a Bay Area wet lab to push Claude beyond computer simulations and into physical biology – including directing robots to run experiments with limited human intervention – while stopping short of clinical trials to avoid competing directly with drugmakers. TechCrunch has more here.

French prosecutors have opened a criminal probe into suspected sexual harassment involving smart glasses as regulators confront complaints about covert filming and workplace use. Meta, the global market leader in smart glasses with a 76% share, sold 7 million units last year. Reuters has more here.

Oregon’s 111 operating data centers consumed 23% of the state’s retail electricity in 2025, a share researchers project could rise to 31%–32% by 2030 as 32 more facilities are built or planned. Mashable has more here.

Joby Aviation says its autonomy technology completed a 3,100-mile flight across the U.S. without a human pilot taking control, using a converted Cessna Caravan and handling taxiing, takeoffs, navigation, and landings autonomously. TechCrunch has more here.

Restaurants are increasingly treating phones like cigarettes, with some locking devices in Yondr pouches, cutting Wi-Fi, or banning screens outright as owners try to restore conversation and curb what they see as an increasingly antisocial dining habit.

“You don’t qualify for an ER visit until after you attend this online group class about how to care for your giant gaping wound at home.”

The Batmobile used as the hero car in Tim Burton’s Batman Returns is heading to auction in November with a $5 million to $7 million estimate, which would make it the most expensive movie car ever sold if it reaches that range.

TechCrunch’s Amanda Silberling tried Orion’s $2,195 AI mattress pad for several months and found that its water-powered cooling and personalized temperature adjustments noticeably improved sleep, but she questioned whether its AI features justify the price.

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