Legendary venture capitalist Vinod Khosla on the single most important decision for startup founders

Longtime venture capitalist Vinod Khosla has simple but crucial advice for startup founders: Success is driven by the people you hire and the questions they ask.

The Silicon Valley mainstay made an appearance in Seattle on Wednesday for a fireside chat at the new AI House.

“The single most important decision by far you will make is the team you build,” Khosla told a packed room of tech entrepreneurs. “Almost certainly, what you have by 2030 will not depend on the plan you have as much as on the team you end up with.”

Khosla recommended hiring people who can learn quickly and ask lots of questions — over those who may have extensive subject matter expertise.

“I have found that the person who learns faster is way better at building businesses than the person who is a deep expert,” he said.

Khosla encouraged founders to hire a team of senior leaders that “should be capable of asking the questions that will make you examine your assumption.”

“The more questions that get asked around your conference table, the better it will go, the faster you will learn, and the faster you will accumulate advantages,” he said. “Big companies don’t do that.”

Khosla suggested a TED Talk from author and entrepreneur Margaret Heffernan about the power of good disagreement.

“If you can encourage those stupid questions … you will have a better culture,” Khosla said. “That’s the crux of entrepreneurial culture.”

Khosla co-founded Sun Microsystems in 1982 and launched Khosla Ventures in 2004. The Silicon Valley firm was an early investor in giants such as Square, Instacart, and DoorDash.

Khosla pointed to the founders of companies like Uber, Airbnb, or Instacart — they didn’t have years of industry experience in taxis, hotels, or grocery, for example.

“Thinking from first principles, being a rapid learner, asking a lot of questions, questioning your own assumptions — it’s way more important to exponential growth and learning than experience,” he said.

When he assesses a new cohort out of the Y Combinator accelerator, Khosla likes to ask how much founders have changed their thinking in the past three months as a way to assess company leaders.

“The message to all of you is don’t think about what you know,” he said. “Think about how fast you can evolve your thinking on whatever space you’re entering.”

Khosla is an investor in the AI2 Incubator, which is now based at the AI House, a sprawling new startup hub along the Seattle waterfront. His firm has backed Seattle-area startups including Loti, Mudstack, Viome, and Lexion, which was acquired by Docusign last year.