The most contrarian bet in venture capital right now is Thrive’s investment in OpenAI at an $80B valuation.

Before you bring your pitchforks against me or wonder if I’ve gone crazy, let me explain.

You can be contrarian in two ways:1

1. Having a different POV than the mainstream


2. Having 100% conviction in the mainstream POV and doubling down on it in a way

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QUOTE OF THE DAY:

"Fiction reveals truths that reality obscures.”

-Jessamyn West (American author)

The more you see, the more skeptical you become. Optimize for skepticism and curiosity. Having been a VC and invested as an angel in well over 100 companies, my inbox flows with ideas of all kinds from aspiring and repeat entrepreneurs. In the earlier days, I’d get excited by ideas especially the first time I saw them. But over time, I soon realize... See more

Like my friends, I often worry about what I can achieve, whether I’ll succeed on my own. But somewhere in the back of my mind, I can still hear that most-American of refrains, the one I thought of over and over again on the trail: I think I can, I think I can, I think I can. . .