Descriptions:
In this episode of 20VC, Harry Stebbings and his panel break down a week packed with headline AI industry moves. The biggest story: Andrej Karpathy — former Tesla AI director and OpenAI co-founder — has announced he is joining Anthropic, adding one of the field’s most recognizable research figures to the company’s roster. Simultaneously, Anthropic is reportedly in talks to raise $30 billion at a valuation approaching $900 billion, nearly tripling its February round of $380 billion, with backers including Sequoia, Altimeter, and others. The panel debates whether 18x ARR is a fair multiple for a company growing at this scale and visibility, and why sophisticated generalist allocators like GreenOaks are treating late-stage Anthropic rounds as among the best risk-adjusted bets in venture.
The episode also covers the Cerebras IPO, which broke the $300-per-share mark on its first day of trading — a strong signal for AI infrastructure public market appetite. Rounding out the week, SpaceX has set June 12 as the date for what would be the largest IPO in history, targeting a $1.75 trillion market cap and raising $75 billion.
The panel offers pointed commentary on the public software market more broadly, discussing Data Dog’s 31% pop and Figma’s 12% gain, and debating whether mature software companies like Wix — currently trading near 1x revenue — represent distressed value or managed decline in an AI-disrupted landscape. A wide-ranging episode for anyone tracking where capital is flowing in the AI ecosystem.
📺 Source: 20VC with Harry Stebbings · Published May 21, 2026
🏷️ Format: Podcast
