Why I take founders on a 3-mile hike before writing a check

The biggest risk in venture capital isn’t losing money. It’s missing the founder who turns a contrarian belief into consensus. That kind of signal doesn’t show up in a pitch—it shows up on a hike.

[Photos: almostfuture/Adobe Stock, Dentones/Adobe Stock]

My team often jokes about the “Vulcan Mind Meld.” They say I need to share a brain with a founder before we can write a check. They aren’t wrong, but the process isn’t science fiction. It’s usually just a walk.

Specifically, it’s a walk to the Stanford Dish.

The path is a 3.5-mile loop in the foothills above the university. It’s steep, exposed, and offers little place to hide. I don’t take founders here for exercise. I take them here because the controlled environment of a boardroom practically demands rehearsed answers. The trail does not.

I don’t prepare a script for these walks. In fact, that’s the point. The pitch is already done; I know the metrics. Now I want to know the human. I want to build the trust required to hear the origin story—the raw, unpolished reason why a founder believes a worldview that everyone else thinks is misguided.

As we hike, I’m listening for that drive, but I’m also mapping their story against my mental framework.

The Map: Consensus vs. Contrarian

For me, every founder sits somewhere on a mental grid defined by two axes: Is your view consensus or contrarian? And if it’s contrarian, how and when will the world come around to your worldview? How will you be proven right?

Being in the consensus is a safe place. We can see this as we start the hike, looking down on the Valley. It looks safe, connected, and crowded.

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