Khosla Ventures is a US venture capital firm founded by Vinod Khosla and an early investor in OpenAI. Recent coverage has focused on its AI deals: it led a $7.5M seed round for privacy-focused AI assistant Ollie, joined a $30M round for AI companion app Tolan, and co-led a $200M round for Arena Intelligence with Lightspeed. Vinod Khosla also told Bloomberg that slowing AI could give China a strategic advantage.
Privacy-focused AI assistant Ollie to shut down in a weekOllie, a privacy-focused AI assistant startup, will shut down on November 6. CEO Bill Lennon said it got close but couldn't stand out against Muse, Instinct and others. It had disclosed a $7.5M seed round led by Khosla Ventures in September and held SOC 2 compliance.
AI companion app Tolan raises another $30MAI companion app Tolan raised another $30M from investors including Union Square Ventures, Khosla Ventures and Homebrew, doubling its total funding. It reports double-digit-millions ARR, over 250,000 active users and 70 million-plus conversations in the past year; about 70% of users are women and 40% are parents.
Crunchbase: Q3 deal pace holds steady as funding fallsCrunchbase data shows most top VCs matched or increased their Q3 deal count even as overall funding fell, partly due to a lack of new giant AI rounds. Y Combinator led with 45 deals, while Insight Partners and Andreessen Horowitz led 18 and 16 rounds; Valor and Atreides tied at $7.7B in led deal value.
Arena Intelligence raises $200M at over $3B valuationArena Intelligence, the startup behind a popular AI model leaderboard, raised $200 million at a $3.1 billion valuation, led by Lightspeed Venture Partners and Khosla Ventures, with participation from Salesforce Ventures and Dell Technologies Capital. It plans to expand into AI safety evaluation to meet growing demand for assessing AI performance and risks.
Axiom Partners founder expects half her AI bets to failAxiom Partners founder Sandhya Venkatachalam runs a $52M fund backing AI startups in industries like construction, industrials and insurance. She seeks non-obvious founders and focuses diligence on whether a team can hit its next milestones, accepting that most bets will fail in pursuit of outliers.
Khosla: America can't slow AIOpenAI early investor and Khosla Ventures founder Vinod Khosla told Bloomberg that slowing AI could hand China a strategic advantage. He argued the U.S. should accelerate AI and energy infrastructure and protect workers displaced by automation rather than jobs, and criticized Silicon Valley for failing to communicate AI's benefits.
PrismML releases tiny reasoning LLMPrismML released Bonsai 2 27B, compressing Alibaba’s Qwen3.8 27B to 5.9GB (≈9–10x memory reduction) while retaining about 98% of benchmark performance; the Caltech-founded startup has a $22.25 million seed round and investors including Khosla Ventures.
The A.I. Daily