To assess a founder's learning rate and critical thinking, Khosla intentionally advocates for ideas he disagrees with. This tactic reveals if a founder will blindly accept advice or critically examine it, demonstrating their ability to filter input—a key trait he looks for.
Related Insights
The fundamental difference in mindset is the initial reaction to an idea. A founder acknowledges risks but frames them as manageable challenges in pursuit of the opportunity, while a non-founder's mind goes straight to why it won't work.
To predict the future health of a partnership, intentionally have difficult conversations before any investment is made. If you can't productively disagree or discuss serious problems before you're formally linked, it's highly unlikely you'll be able to do so when the stakes are higher post-investment.
Since startups lack infinite time and money, an investor's key diligence question is whether the team can learn and iterate fast enough to find a valuable solution before resources run out. This 'learning velocity' is more important than initial traction or a perfect starting plan.
Rather than imposing processes after investing, VCs can use frameworks like the "sales sprint" as a pre-investment litmus test. Sharing the approach and observing the founder's reaction reveals their mindset. A founder who is eager to adopt a disciplined, customer-centric process is a stronger bet than one who must be forced into it.
To identify non-consensus ideas, analyze the founder's motivation. A founder with a deep, personal reason for starting their company is more likely on a unique path. Conversely, founders who "whiteboarded" their way to an idea are often chasing mimetic, competitive trends.
Successful founders passionately defend their vision while simultaneously processing tough questions without defensiveness. This balance allows them to navigate the 'idea maze' effectively, learning and adapting as they go.
A rising tide lifts all boats. The true test of a founder partnership emerges during downturns. Diligence should focus on teasing out traits like adaptability, humility, and accountability, which predict how a founder will react when plans inevitably go awry.
To truly validate their idea, Moonshot AI's founders deliberately sought negative feedback. This approach of "trying to get the no's" ensures honest market signals, helping them avoid the trap of false positive validation from contacts who are just being polite.
A founder deep in the idea maze can articulate not just their current path, but also the alternatives they considered and why they were rejected. This demonstrates a profound understanding of their domain and problem space.
Great founders turn a pitch into a collaborative discussion by asking investors to identify business weaknesses. This signals curiosity, strength, and a desire for genuine feedback over just presenting a perfect picture. It demonstrates a coachable leader who is focused on gathering data to improve.
