Structuring a Productive Gap Year

Henry Shi, founder of Super.com (scaled to $200M+ annual revenue, 50 million users, profitable), joins Village Global GP Anne Dwane to discuss his unconventional path from founder to Anthropic.

Henry shares why he stepped back from his company at its peak, what he learned during his gap year building AI resources in public, the patterns he discovered tracking lean AI companies, and why he ultimately chose a frontier lab over VC or starting another company. He also gives a candid look inside Anthropic's culture and shares his predictions for what's coming in 2026. 

Mentioned in the Episode:

• Lean AI Leaderboard: https://leanaileaderboard.com/
• AI Crash Course (GitHub): https://github.com/henrythe9th/AI-Crash-Course
• AI 2027 Report: https://ai-2027.com/
• Super.com: https://www.super.com
• Anthropic: https://www.anthropic.com
• Henry on X: https://x.com/henrythe9ths
• Henry on LinkedIn: https://www.linkedin.com/in/henrythe9th/

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