Ray Dalio & Reid Hoffman Live in NYC

On February 19th, 2026, Village Global brought together our luminary LPs Ray Dalio and Reid Hoffman for a live conversation in New York, moderated by Ben Casnocha.

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For those who couldn’t make it, Ray and Reid covered a lot of ground in just over an hour. Here are some of the themes from the discussion that we’ve been mulling over in the days since: 

Emotional fortitude is required to ride the rollercoaster of markets. Ray said we are in Stage 6 of what he’s termed the Big Cycle: “There is great disorder arising from being in a period in which there are no rules, might is right, and there is a clash of great powers.” In these times, he emphasized the importance of holding onto the handlebar as you ride the rollercoaster of markets and life – and developing the emotional fortitude to stomach unexpected dips. Is emotional fortitude the ultimate skill for humans to develop in an age of AI and great disorder? How, exactly, does one do that?

Digital twins are coming, and they may do deals together. Ray spends hours each week curating his AI twin's knowledge set. Within a few years, he predicts, your digital twin will negotiate on your behalf with other agents. Do we each need to be training our digital twin to represent us accurately in the world of agents?

AI as a thinking partner, not a decision maker. Ray described how he uses AI: "It's a really brilliant partner. But you have to argue with it. You can't let it make decisions. It thinks it's very smart – it's not as smart as it thinks it is.” Every prompt related to a decision scenario should start with, "Here are the criteria that matter to me…" Always be specifying criteria. The humans who succeed with AI will be the ones who at once are ravenous users of the endlessly intelligent chatbot, but also unafraid of pushing back. How do you develop the meta awareness to know, in real time, whether you’re applying your own human judgment on the model’s outputs?

Be wary of certainty in times of disruption. Reid made the case that in times of disruption, overly strong conviction about the state of technology is a liability. One’s edge comes from experimenting, adapting, and staying flexible as you update your mental models. Revisit your assumptions routinely. 

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Thanks to Ray Dalio and Reid Hoffman for a great conversation — and to everyone who attended virtually and on-site in NYC.

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