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Venn Diagrams · Oct 18, 2025

Jake Paul is probably a better investor than you

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Anthony McGuire · Venn Diagrams

In 2021, Jake Paul launched Anti Fund with Geoffrey Woo. Since then, the fund has invested in companies like OpenAI, Polymarket, and Anduril.

Is Jake Paul himself doing technical diligence on LLM architectures or defense AI systems? Probably not, but that’s not what makes him valuable on your cap table.

Jake has social capital and cultural leverage.

He’s built one of the most recognized brands on the internet. He’s gone from viral YouTuber to global boxer to serial entrepreneur.

When Jake Paul tweets about investing in Polymarket, people roll their eyes. But they’re missing the point.

In 2025, attention is a growth engine. You don’t just want operators and MBAs around the table. You want people who can shape the narrative and move culture.

Startups grow through storytelling and creators like Jake Paul are world class storytellers. Content creators can double as strategic investors and distribution engines.

You can laugh at Jake Paul or you can realize he’s playing the modern game better than most.

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