The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Anthropic's $10BN Fundraise: Have They Beaten Cursor Already | a16z's $15BN Fundraise: Is the Middle Dead in VC Today? | How OpenAI Could Go to Zero and ElevenLabs at $11BN: Buy or Not?
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Jan 15, 2026 
Jason Lemkin, a seasoned SaaS entrepreneur and founder of SaaStr, joins Rory O'Driscoll, a venture capitalist with a knack for enterprise investing. They dive deep into Anthropic's impressive $10B fundraising and its implications for valuation and IPO prospects. The duo debates whether Claude has outperformed Cursor in the AI API landscape and explores the existential risks facing OpenAI. They also analyze the dynamics of venture capital, pondering if the middle market is fading as boutiques and mega-funds thrive.
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When Fast Growth Justifies High Valuations
- Anthropic's rapid revenue growth makes a high valuation plausible if growth continues another year.
- Paying up is rational when a company grows ~10x year-on-year because future revenue compresses the multiple.
From API To Full Product Ownership
- Anthropic has expanded from API seller to owning coding and general knowledge work products.
- Owning both API and end-user apps captures more revenue and creates platform stickiness.
Get Comfortable Being Scared
- Founders must accept being scared and operate in high-change environments.
- If you cannot live with rapid existential risk, consider a different career.