The Art of Nuanced Investment Evaluations

This week I spoke with Shaun Maguire, a Partner at Sequoia Capital. He led their investments into SpaceX, The Boring Co, and X among others. Prior to Sequoia Shaun co-founded a cybersecurity company which was acquired for $1B and worked at DARPA. I could have happily spoken with Shaun for four hours.

We covered:

(0:00) Speaking his mind in public

(13:38) Trust and the media

(24:27) Tech’s political flip

(29:27) Investing in hard tech vs. software

(45:27) Thinking with a beginner's mind

(52:30) Fulfillment in investing

(59:33) Investing in outlier people

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