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WYI

Would You Invest #1

Vinay Gupta

Vinay Gupta

07 Jan 2026
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WYI

Shield AI at 8B


Anthropic at 350B

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When Taste Matters

When Taste Matters

Taste is not just prescient. It's also a lagging indicator. It shows up when engineering alone is not enough. Conventional wisdom is that taste enables you to see into the future. Tastemakers are meant to see ahead. Yet, they often don’t have the opportunity to influence tastes

13 Aug 2026
Data Exhaust

Data Exhaust

What happens when you give Claude skills

02 Jul 2026
Die With Zero

Die With Zero

A book club discussion with Brown Papas Unite

19 Jun 2026
Paying People To Get Out Of The Way

Paying People To Get Out Of The Way

Last week at dinner, the conversation shifted to Universal Basic Income (UBI): Are we building systems to help people keep up, or to pay them to get out of the way? Someone referred to it as the permanent underclass. The conversation got quiet because this outcome is plausible, and many

03 Jun 2026

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The economics of friendship: how money, relationships and culture is made.

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